Herbicide composition containing an azine compound

Abstract

The present invention relates to a herbicidal composition comprising at least one compound of formula (I) [wherein the variable elements are defined herein] and at least one further active compound selected from herbicides of types b1) to b15) and antidote C. 【Chemical 1】 TIFF2025522995000244.tif36170

Description

Technical Field

[0001] The present invention relates to a herbicidal composition comprising at least one compound of formula (I) and at least one further compound selected from herbicidally active compounds and antidotes.

Background Art

[0002] In principle, for crop protection compositions, it is desirable to increase the specific activity of the active compounds and the reliability of the effects. It is particularly desirable that the crop protection composition effectively controls harmful plants and is compatible with the useful plants in question at the same time. Also desirable is a broad spectrum of activity that allows for the simultaneous control of harmful plants. In many cases, this cannot be achieved using a single herbicidally active compound.

[0003] Many very effective herbicides do not necessarily have satisfactory compatibility with useful plants, especially dicotyledonous crop plants such as soybeans, sunflowers, cotton, rape, etc., and also with gramineous plants such as barley, millet, corn, rice, wheat, and sugarcane, i.e., in addition to harmful plants, crop plants are also damaged to an unacceptable extent. By reducing the application rate, useful plants can be protected; however, naturally, the range of control of harmful plants is also reduced.

[0004] In many cases, the problem is that the herbicide can only be applied within a narrow time frame to achieve the desired herbicidal effect, and that time frame can be unexpectedly affected by weather conditions.

[0005] It is known that by a special combination of specifically active different herbicides, the activity of the herbicide components is enhanced in the sense of a synergistic effect. In this way, it is possible to reduce the application rate of the herbicidally active compounds required for the control of harmful plants.

[0006] Furthermore, in some cases, it is known that the combination of a specifically acting herbicide and an organic active compound (some of which may also have herbicidal activity) improves the compatibility with crop plants. In these cases, the active compound acts as an antidote or antagonist and is also called a safener to reduce or even prevent damage to the crop plants. SUMMARY OF THE INVENTION PROBLEM TO BE SOLVED BY THE INVENTION

[0007] An object of the present invention is to provide a herbicide composition that exhibits high activity against unwanted harmful plants. At the same time, the composition must have good compatibility with useful plants. In addition, the composition according to the present invention must have a broad spectrum of activity. MEANS FOR SOLVING THE PROBLEM

[0008] This and further objects are achieved by the following herbicide composition.

[0009] Accordingly, the present invention provides: Formula (I)

Chemical formula

[0010] The present invention relates in particular to a composition in the form of a herbicidal active agrochemical composition comprising, as defined above, at least one compound of formula (I), at least one further compound selected from herbicide B and antidote C, at least one liquid and / or solid carrier and / or one or more surfactants, and, if appropriate, one or more further adjuvants customary in agrochemical compositions, in a herbicidally effective amount of a combination of active compounds.

[0011] The present invention also relates to a composition in the form of an agrochemical composition formulated as a one - component composition comprising a combination of active compounds comprising at least one compound of formula (I), at least one further active compound selected from herbicide B and antidote C, at least one solid or liquid carrier and / or one or more surfactants, and, if appropriate, one or more further adjuvants customary in agrochemical compositions.

[0012] The present invention also relates to a composition in the form of an agrochemical composition formulated as a two - component composition comprising a first component comprising at least one compound of formula (I), at least one solid or liquid carrier and / or one or more surfactants, and a second component comprising at least one further active compound selected from herbicide B and antidote C, at least one solid or liquid carrier and / or one or more surfactants, and wherein both components may further comprise further adjuvants customary in agrochemical compositions.

[0013] Surprisingly, the compositions according to the invention comprising at least one compound of formula (I) and at least one herbicide B have a herbicidal activity which is better than the herbicidal activity observed with the individual compounds or expected on the basis of a broader activity spectrum, i.e. an excellent activity against harmful plants. The herbicidal activity expected for a mixture based on the individual compounds can be calculated using Colby's formula (see below). If the observed activity exceeds the expected additive activity of the individual compounds, a synergistic effect is said to exist.

[0014] Furthermore, the time frame in which the desired herbicidal action can be achieved can be extended by the composition according to the invention comprising at least one compound of formula (I), at least one herbicide B and optionally an antidote C. This allows for more flexible timing of application of the composition according to the invention compared to the individual compounds.

[0015] The composition according to the invention comprising both at least one compound of formula (I) and at least one of the compounds listed under C also has good herbicidal activity against harmful plants and better compatibility with useful plants.

[0016] Surprisingly, the composition according to the invention comprising at least one compound of formula (I), at least one herbicide B and at least one of the compounds listed under C has a herbicidal activity better than that observed for the individual compounds, or expected based on a broader activity spectrum, i.e. better activity against harmful plants, and shows better compatibility with useful plants than a composition comprising only one compound I and herbicide B.

[0017] The invention further relates to a method for controlling unwanted vegetation, especially when crop plants are cultivated.

[0018] The invention also relates to a method for the drying or defoliation of plants.

DETAILED DESCRIPTION OF THE INVENTION

[0019] As used herein, the terms "control" and "eradication" are synonyms.

[0020] As used herein, the terms "unwanted vegetation" and "harmful plants" are synonyms.

[0021] If the compounds of formula (I), herbicidal compounds B and / or antidotes C described herein can form geometric isomers, for example E / Z isomers, it is possible to use both the pure isomers and mixtures thereof in the composition according to the invention.

[0022] If the compound of formula (I), the herbicidal compound B and / or the antidote C described in this specification have one or more centers of chirality and, as a result, exist as enantiomers or diastereomers, both pure enantiomers and diastereomers and mixtures thereof can be used in the compositions according to the invention.

[0023] Within the substituents of the compound of formula (I), the corresponding isotopic deuterium can also be used instead of hydrogen.

[0024] If the compound of formula (I), the herbicidal compound B and / or the antidote C described in this specification have ionizable functional groups, they can also be used in the form of their agriculturally acceptable salts. Generally, suitable are, respectively, salts of cations that do not adversely affect the activity of the active compound and acid addition salts of acids in which the cations and anions do not adversely affect the activity of the active compound.

[0025] Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium, alkaline earth metals, preferably calcium and magnesium ions, and transition metals, preferably manganese, copper, zinc and iron ions, further ammonium and substituted ammonium in which 1 to 4 hydrogen atoms are replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), further phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, such as trimethylsulfonium and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium, and finally salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[0026] Anions of useful acid addition salts are mainly chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicic acid, hexafluorophosphoric acid, benzoic acid and also anions of C1-C4-alkanoic acids, preferably formic acid, acetic acid, propionic acid and butyric acid.

[0027] The compounds of formula (I) described herein having a carboxyl group, herbicide A, herbicide B and / or antidote C can be in the acid form, in the form of an agriculturally suitable salt as described above, or in the form of an agriculturally acceptable derivative, for example as an amide, for example as a mono- and di-C1-C6-alkylamide or arylamide, as an ester, for example as an allyl ester, propargyl ester, C1-C 10 -alkyl ester, alkoxyalkyl ester, tefuryl ((tetrahydrofuran-2-yl)methyl) ester, and also as a thioester, for example as a C1-C 10 -alkyl thioester. Preferred mono- and di-C1-C6-alkylamides are methylamide and dimethylamide. Preferred arylamides are, for example, anilide and 2-chloroanilide. Preferred alkyl esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) ester. Preferred C1-C4-alkoxy-C1-C4-alkyl esters are straight-chain or branched C1-C4-alkoxyethyl esters, for example 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (buthyl), 2-butoxypropyl, or 3-butoxypropyl ester. Straight-chain or branched C1-C 10 An example of a C1-C4-alkyl thioester is ethyl thioester.

[0028] Further embodiments of the invention are apparent from the claims, the description and the examples. It will be understood that the features described above and further exemplified below of the subject matter of the invention can be applied not only in the combinations given in each particular example, but also in other combinations without departing from the scope of the invention.

[0029] The variable elements R 1 ~R 6 and R a ~R eThe organic moieties described in the definition are, like the term halogen, a collective term for the individual enumeration of the individual members of that group. The term halogen, in each case, refers to fluorine, chlorine, bromine or iodine. All hydrocarbon chains can be linear or branched, and the prefix C n ~C m indicates, in each case, the possible number of carbon atoms in the group.

[0030] Examples of such meanings are as follows: - C1~C3-alkyl, and also the C1~C3-alkyl moieties of di(C1~C3-alkyl)amino, C1~C3-alkoxy-C1~C3-alkyl: for example, CH3, C2H5, n-propyl and CH(CH3)2; - C1~C4-alkyl: for example, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, CH(CH3)-C2H5, CH2-CH(CH3)2 and C(CH3)3; - The C1-C6-alkyl, and also C1-C6-cyanoalkyl, C1-C6-alkyloxy-C1-C6-alkyl, C1-C6-alkyloxy-C1-C6-alkyloxy-C1-C6-alkyl, di(C1-C6-alkyloxy)C1-C6-alkyl, C1-C6-haloalkyloxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyl, C3-C6-haloalkenyloxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyloxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-alkyloxycarbonyl-C1-C6-alkyl, C1-C6-haloalkyloxycarbonyl-C1-C6-alkyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl C1-C6-alkyl moiety: the above C1-C4-alkyl, and also, for example, n-phenyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylphenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl, n-phenyl or n-hexyl; - C1-C3-haloalkyl: the above C1-C3-alkyl partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl; - C1-C4 haloalkyl: the C1-C4 alkyl partially or completely substituted by fluorine, chlorine, bromine and / or iodine, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 1,1,2,2,-tetrafluoroethyl and 1-trifluoromethyl-1,2,2,2-tetrafluoroethyl; - C1-C6 haloalkyl: the above C1-C4 haloalkyl and also, for example, 5-fluorophenyl, 5-chlorophenyl, 5-bromophenyl, 5-iodophenyl, undecafluorophenyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl; - C3-C6 alkenyl, and also the C3-C6 alkenyl moiety of C3-C6 alkenyloxy-C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkoxy-C1-C6 alkyl, C3-C6 alkenyloxycarbonyl-C1-C6 alkyl: for example, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl; - C3-C6-haloalkenyl, and also the C3-C6-haloalkenyl moiety of C3-C6-haloalkenyloxy-C1-C6-alkyl: the above C3-C6-alkenyl groups which are partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example, 2-chloroprop-2-en-1-yl, 3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1-yl or 2,3-dibromobut-2-en-1-yl; - C3-C6 alkynyl, and also the C3-C6 alkynyl moiety of C3-C6 alkynyloxycarbonyl-C1-C6 alkyl: for example, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; - C3-C6 haloalkynyl: the above C3-C6 alkynyl groups partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example, 1,1-difluoroprop-2-yn-1-yl, 3-chloroprop-2-yn-1-yl, 3-bromoprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl; - C1-C3 alkoxy, and also the C1-C3 alkoxy moiety of C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxycarbonyl: for example, methoxy, ethoxy, propoxy; - C1-C4 alkoxy: for example, methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, and 1,1-dimethylethoxy; - C1-C6 alkoxy, and also the C1-C6 alkoxy moiety of C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkoxy-C1-C6 alkyl, di(C1-C6 alkoxy)C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl: the above C1-C4 alkoxy, and also for example pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxybutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy; - C1-C3-haloalkoxy: the above C1-C3-alkoxy group partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy; - C1-C4 haloalkoxy: the C1-C4 alkoxy group partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy; - C1-C6 haloalkoxy, and also the C1-C6 haloalkoxy moiety of C1-C6 haloalkoxy-C1-C6 alkyl and C1-C6 haloalkoxycarbonyl-C1-C6 alkyl: the above C1-C4 haloalkoxy, and also for example 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy; - C1-C3 alkylthio: for example, methylthio, ethylthio, propylthio, 1-methylethylthio; - C1-C4 alkylthio: for example, methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, and 1,1-dimethylethylthio; - C1-C6-alkylthio and also the C1-C6-alkylthio moiety of C1-C6-alkylthio-C1-C6-alkyl: the above C1-C4-alkylthio and also, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio; - C1-C6-alkylsulfinyl (C1-C6-alkyl-S(=O)-), and also C1-C6-alkylsulfinyl-C1-C6-alkyl C1-C6-alkylsulfinyl moieties: for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl; - C1-C6-alkylsulfonyl (C1-C6-alkyl-S(O)2-), and also C1-C6-alkylsulfonyl-C1-C6-alkyl C1-C6-alkylsulfonyl moieties: for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl; - (C1-C3-alkyl)amino: for example, methylthio, ethylthio, propylamino, 1-methylethylamino.

[0031] It must be understood that the preferred embodiments of the invention referred to hereinafter are preferred either independently of one another or in any combination with one another.

[0032] According to a preferred embodiment of the invention, compounds of formula (I) in which the variables, independently of one another or in combination with one another, have the following meanings are preferred.

[0033] A particular group of embodiments relates to diamino triazine compounds of formula (I), in which R 1 is F.

[0034] Preferred embodiments are diaminotriazine compounds of formula I [wherein, R 2 is selected from the group consisting of H, halogen, CH3, C1-haloalkyl; in particular H, halogen, CH3; more particularly H, F, Cl, CH3].

[0035] A further specific group of embodiments relates to diaminotriazine compounds of formula I [wherein, R 3 is H or F, preferably H].

[0036] A further specific group of embodiments relates to diaminotriazine compounds of formula I [wherein, R 4 is selected from the group consisting of halogen, CH3, C1-haloalkyl; in particular consisting of halogen, CH3; more particularly selected from the group consisting of Br, Cl, CH3].

[0037] Preferred embodiments are diaminotriazine compounds of formula I [wherein, R 5 is selected from the group consisting of H, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy; in particular hydrogen, fluorine, C1-C4-alkyl, such as methyl, ethyl, n-propyl, 2-propyl, n-butyl, 2-butyl, isobutyl or tert.-butyl, C1-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl, C1-C4-alkoxy, such as methoxy or ethoxy and C1-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy].

[0038] A more specific group of embodiments relates to diaminotriazine compounds of formula I [wherein, R 6relates to a diaminotriazine compound selected from the group consisting of H, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, particularly from the group consisting of hydrogen, fluorine and C1-C4-alkyl, more particularly hydrogen, fluorine and methyl, especially fluorine and methyl.

[0039] In group (1) of embodiments, R 7 is as defined above. Preferably, R 7 is selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-cycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl.

[0040] A further specific group of embodiments is of formula (I) [wherein R 6 and R 7 together with the carbon atom to which they are attached form a moiety selected from the group consisting of carbonyl, C3-C6-cycloalkane, C3-C6-cycloalkenyl, 3- to 6-membered saturated or partially unsaturated heterocyclyl (wherein the carbocyclic and heterocyclic rings are unsubstituted, partially or fully halogenated, or carry 1 to 6 C1-C6-alkyl groups), and moiety >C=CR x R y wherein R x and R y are hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, or CR x R y forms a 3- to 6-membered cycloalkyl], relates to a diaminotriazine compound. Preferably, R 6 and R 7 together with the carbon atom to which they are attached form a C3-C6-cycloalkane.

[0041] CR 5 R 6 R7 Particularly preferred examples are those where R 2 , R 3 and R 4 are those groups given in rows 1 to 65 of Table 1a.

[0042] [Table 1]

[0043] [Table 2]

[0044] [Table 3]

[0045] R 8 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, (C1-C6-alkoxy)-C1-C6-alkyl, (C1-C6-alkoxy)-C2-C6-alkenyl, (C1-C6-alkoxy)-C2-C6-alkynyl, (C1-C6-cycloalkyl)-C2-C6-alkynyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, (C3-C6-cycloalkoxy)-C1-C4-alkyl, and the aforementioned groups are unsubstituted or partially or fully halogenated, and the alicyclic moiety of the last six mentioned groups may have 1, 2, 3, 4, 5 or 6 methyl groups; Preferably, R 8 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, (C1-C6-alkoxy)-C1-C6-alkyl.

[0046] In particular, R 8 is selected from the group consisting of CH3, CH2CCH, CH2CCCH3, CH2OCH3, CH(CH3)CCH, CH(CH3)CCCH3, and in particular from the group consisting of CH3, CH2CCH, CH2CCCH3, CH2OCH3.

[0047] Certain embodiments of Compound I are the following Compounds I-A, I-B, I-C, I-D, I-E, I-F:

Chemical formula

[0048] Table 1-1 R of each individual compound 2 , R 4 and R 8 For the combinations of, the compounds of Formula I-A, I-B, I-C, I-D, I-E, I-F (Compounds I-A.1-1.A-1 to I-A.1-1.A-48, I-B.1-1.A-1 to I-B.1-1.A-48, I-C.1-1.A-1 to I-C.1-1.A-48, I-D.1-1.A-1 to I-D.1-1.A-48, I-E.1-1.A-1 to I-E.1-1.A-48, I-F.1-1.A-1 to I-F.1-1.A-48) where the meaning corresponds to one row of Table A in each case.

[0049]

Table 4

[0050]

Table 5

[0051]

Table 6

[0052] According to another preferred embodiment of the present invention, the composition contains, as Component A, at least one compound selected from I-A.1-1.A-1 to I-A.1-1.A-48.

[0053] According to another preferred embodiment of the present invention, the composition contains, as Component A, at least one compound selected from I-B.1-1.A-1 to I-B.1-1.A-48.

[0054] According to another preferred embodiment of the present invention, the composition contains, as component A, at least one compound selected from I-C.1-1.A-1 to I-C.1-1.A-48.

[0055] According to another preferred embodiment of the present invention, the composition contains, as component A, at least one compound selected from I-D.1-1.A-1 to I-D.1-1.A-48.

[0056] According to another preferred embodiment of the present invention, the composition contains, as component A, at least one compound selected from I-E.1-1.A-1 to I-E.1-1.A-48.

[0057] According to another preferred embodiment of the present invention, the composition contains, as component A, at least one compound selected from I-F.1-1.A-1 to I-F.1-1.A-48.

[0058] According to another preferred embodiment of the present invention, the composition contains, as component A, the formula

Chemical formula

[0059] According to another preferred embodiment of the present invention, the composition contains, as component A, the formula

Chemical formula

[0060] According to another preferred embodiment of the present invention, the composition contains, as component A, the formula

Chemical formula

[0061] According to another preferred embodiment of the present invention, the composition contains, as component A, the formula

Chemical formula

[0062] The diamino triazine compounds of formula (I) according to the present invention can be prepared by standard processes of organic chemistry, for example, by the following processes.

[0063] Process A) The diamino triazine of formula (I) can be synthesized by adding the corresponding 2 - alkoxyaniline of formula (II) to the halotriazine of formula (III) in an inert organic solvent under basic or acidic conditions, as shown in the following scheme:

Chemical formula

[0064] Variable R 1 、R 2 、R 3 and R 4 、R 6 、R 7 and R 8 have the meanings as in formula (I) described above, in particular, the preferred meanings, Hal is halogen; preferably Cl or Br; particularly preferably Cl.

[0065] The reaction between the halotriazine of formula (III) and the amine compound of formula (II) is usually carried out in an inert organic solvent at a temperature from 50 °C to the boiling point of the reaction mixture.

[0066] The halotriazines of formula (III) and the compounds of formula (II) are used in equimolar amounts or the compounds of formula (II) are used in an excess amount relative to the halotriazine of formula (III). Preferably, the molar ratio of the compound of formula (II) to the halotriazine of formula (III) is in the range of 2:1 to 1:1, preferably 1.5:1 to 1:1, particularly preferably 1:1.

[0067] The reaction of the halotriazine of formula (III) with the compound of formula (II) is carried out in an organic solvent. Suitable solvents are those that can at least partially, preferably completely dissolve the halotriazine of formula (III) and the aniline of formula (II) under the reaction conditions. Examples of suitable solvents include aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresol, o-, m- and p-xylene; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF); esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile; and dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, Ν,Ν-dimethylformamide (DMF), Ν,Ν-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), Ν,Ν’-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP). Preferred solvents are the ethers as defined above. The term "solvent" as used herein also includes mixtures of two or more of the above compounds.

[0068] The reaction of the halotriazine of formula (III) with the compound of formula (II) is carried out in the presence of a base or an acid. Examples of suitable bases include metal-containing bases and nitrogen-containing bases.

[0069] Examples of suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; alkali metal and alkaline earth metal oxides, and other metal oxides such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal formates, acetates and other metal salts of carboxylic acids, such as sodium formate, sodium benzoate, lithium acetate, sodium acetate, potassium acetate, magnesium acetate, and calcium acetate; alkali metal and alkaline earth metal carbonates, such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, and calcium carbonate, and alkali metal hydrogen carbonates (bicarbonates), such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates, such as sodium phosphate, potassium phosphate and calcium phosphate; alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide.

[0070] Preferred bases are the alkoxides of alkali metals and alkaline earth metals as defined above. The term base as used herein also includes mixtures of two or more, preferably two, of the above compounds.

[0071] The base can be used in equimolar concentration or in excess, preferably 1 to 10, particularly preferably 2 to 4 equivalents, based on the halotriazine of formula (III), and these can also be used as a solvent.

[0072] Examples of suitable acids are inorganic salts such as hydrofluoric acid, hydrochloric acid, Inorganic acids such as hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, p-toluenesulfonic acid; Lewis acids such as boron trifluoride, aluminum chloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid can be used.

[0073] Preferred acids are inorganic acids.

[0074] The acid is generally used in an excess amount or, where appropriate, can also be used as a solvent.

[0075] The end of the reaction can be easily determined by a skilled person in a routine manner.

[0076] The reaction mixture is worked up by conventional methods, for example by mixing with water, separating the phases and, where appropriate, purifying the crude product.

[0077] The aniline of formula (II) required for the preparation of the compound of formula (I) is commercially available or can be prepared by standard processes of organic chemistry, for example the nitration of commercially available phenol and subsequent reduction of the nitro group.

[0078] The halotriazine of formula (III) required for the preparation of the diaminotriazine of formula (I) is known from the literature, commercially available and / or can be prepared analogously (for example J.K. Chakrabarti et al., Tetrahedron 1975, 31, 1879 - 1882) by reacting a thiotriazine of formula (IV) with a halogen source (for example, Cl) or other suitable halogenating agent (for example, SOCl2).

[0079] Process B) The diamino triazine of formula (I) can be synthesized by alkylating the corresponding phenol diamino triazine of formula (IV) under basic conditions in an inert organic solvent as shown in the following scheme:

Chemical formula

[0080] The variable R 1 、R 2 、R 3 and R 4 、R 6 、R 7 and R 8 have the meanings as in formula (I) described above, in particular, the preferred meanings, Hal is halogen; Preferably, it is I or Br or Cl.

[0081] The alkylation reaction of the phenol diamino triazine of formula (IV) can be carried out from room temperature to the boiling point of the reaction mixture in the organic solvent.

[0082] The alkylating reagent of formula (V) and the compound of formula (IV) are used in equimolar amounts, or the compound of formula (V) is used in an excess amount relative to the phenol diamino triazine of formula (IV). Preferably, the molar ratio of the compound of formula (V) to the phenol diamino triazine of formula (IV) is in the range of 1.5:1 to 1:1, preferably in the range of 1.2:1.

[0083] The reaction of the halotriazine of formula (III) with the compound of formula (II) is carried out in the presence of a base or an acid. Examples of suitable bases include metal-containing bases and nitrogen-containing bases.

[0084] Examples of suitable metal-containing bases are hydrides of alkali metals and alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, carbonates of alkali metals and alkaline earth metals, such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate and calcium carbonate, and alkali metal hydrogen carbonates (bicarbonates), such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; phosphates of alkali metals and alkaline earth metals, such as sodium phosphate, potassium phosphate and calcium phosphate; alkoxides of alkali metals and alkaline earth metals, such as potassium tert-butoxide, potassium tert-pentoxide.

[0085] Process C)

Chemical formula

[0086] The reaction of the biguanidine of formula (VI) with the carbonyl compound of formula (VII) is usually carried out at a temperature from 50 °C to the boiling point of the reaction mixture, preferably at 50 °C to 200 °C (for example, R. Sathunuru et al., J. Heterocycl. Chem. 2008, 45, 1673-1678).

[0087] The reaction can be carried out continuously or batchwise under atmospheric pressure or elevated pressure, and, where appropriate, under an inert gas.

[0088] In one embodiment of the process according to the invention, the biguanidine of formula (VI) and the carbonyl compound of formula (VII) are used in equimolar amounts.

[0089] In another embodiment of the process according to the invention, the carbonyl compound of formula (VII) is used in an excess with respect to the biguanidine of formula (VI).

[0090] Preferably, the molar ratio of the carbonyl compound of formula (VII) to the biguanidine of formula (VI) is in the range from 1.5:1 to 1:1, preferably from 1.2:1 to 1:1, particularly preferably 1.2:1, and very particularly preferably 1:1.

[0091] The reaction of the biguanidine of formula (VI) with the carbonyl compound of formula (VII) is carried out in an organic solvent.

[0092] Suitable solvents are, in principle, all solvents which are capable of dissolving the biguanidines of formula (VI) and the carbonyl compounds of formula (VII) at least partially, preferably completely, under the reaction conditions.

[0093] Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and C s ~C s- mixtures of alkanes; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresol, ο-, m- and p-xylene; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile and dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, Ν,Ν-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), Ν,Ν’-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP).

[0094] Preferred solvents are the ethers and dipolar aprotic solvents defined above. More preferred solvents are the ethers defined above.

[0095] The term solvent as used herein also includes mixtures of two or more of the above compounds.

[0096] The reaction of the biguanide of formula (VI) with the carbonyl compound of formula (VII) is carried out in the presence of a base.

[0097] Examples of suitable bases include metal-containing bases and nitrogen-containing bases. Examples of suitable metal-containing bases are inorganic compounds such as oxides of alkali metals and alkaline earth metals and other metal oxides such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; hydrides of alkali metals and alkaline earth metals such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, amides of alkali metals such as lithium amide, sodium amide and potassium amide, carbonates of alkali metals and alkaline earth metals such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate and calcium carbonate, alkali metal hydrogen carbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; phosphates of alkali metals and alkaline earth metals such as sodium phosphate, potassium phosphate and calcium phosphate; and also organic bases such as tertiary amines, stannous teeth, tri-Ci-C6-alkylamines such as triethylamine, trimethylamine, N-ethyldiisopropylamine and N-methyl-piperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine and 4-dimethylaminopyridine (DMAP) and also bicyclic amines such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN).

[0098] Preferred bases are the tri-C1-C6-alkylamines as defined above. The term base as used herein also includes mixtures of two or more, preferably two, of the above compounds. It is particularly preferred to use one base. The base is generally used in excess, but can be used in equimolar amounts or, where appropriate, as a solvent. Based on the biguanidine of formula (VII), preferably 1 to 5 base equivalents, particularly preferably 3 base equivalents of base are used. The end of the reaction can be readily determined by a person skilled in the art in a conventional manner.

[0099] The reaction mixture is worked up in a conventional manner, for example by mixing with water, phase separation and, if necessary, chromatographic purification of the crude product. Some of the intermediates and final products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at a moderately elevated temperature.

[0100] If the intermediates and final products are obtained as solids, purification can also be carried out by recrystallization or digestion.

[0101] The carbonyl compounds of formula (VII) required for the preparation of the azines of formula (I) are known from the literature and / or are available commercially.

[0102] The biguanidines of formula (VI) required for the preparation of the azines of formula (I) can be prepared by reacting cyanoguanidine of formula (VIII) with an amine of formula (II) in the presence of an acid:

Chemical formula

[0103] The reaction of the guanidine of formula (VII) with the amine of formula (II) is usually carried out at 50 °C to 150 °C, preferably 80 °C to 130 °C. Microwave technology can be used if necessary (for example, C.O. Kappe, A. Stadler, Microwaves in Organic and Medicinal Chemistry, Weinheim 2012).

[0104] The reaction can be carried out in a flow reactor or batchwise under atmospheric pressure or elevated pressure, and if appropriate, under an inert gas.

[0105] In one embodiment of the process according to the invention, the guanidine of formula (VII) and the amine of formula (II) are used in equimolar amounts.

[0106] In another embodiment of the process according to the invention, the amine of formula (II) is used in an excess with respect to the guanidine of formula (VII).

[0107] Preferably, the molar ratio of the amine of formula (II) to the guanidine of formula (VII) is in the range of 2:1 to 1:1, preferably 1.5:1 to 1:1, particularly preferably 1:1.

[0108] The reaction of the guanidine of formula (VII) with the amine of formula (II) is carried out in an organic solvent. The term solvent as used herein also includes mixtures of two or more solvents.

[0109] All solvents that can at least partially, preferably completely dissolve the guanidine of formula (VII) and the amine of formula (II) under the reaction conditions are in principle suitable. Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8-alkanes; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresol, o-, m- and p-xylene; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and propionitrile and dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, Ν,Ν-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), Ν,Ν’-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP).

[0110] Preferred solvents are the ethers, nitriles and dipolar aprotic solvents as defined above.

[0111] More preferred solvents are the nitriles as defined above.

[0112] The reaction of the guanidine of formula (VII) with the amine of formula (II) is carried out in the presence of an acid.

[0113] Examples of suitable acids are inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, p-toluenesulfonic acid; Lewis acids such as boron trifluoride, aluminum chloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid, and these can be used. The acid is generally used in an excess amount or, where appropriate, can be used as a solvent.

[0114] The guanidine of formula (VII) required for the preparation of the biguanide of formula (VII) is commercially available or can be prepared according to literature procedures (e.g., J.L. LaMattina et al., J. Med. Chem. 1990, 33, 543 - 552; A. Perez-Medrano et al., J. Med. Chem. 2009, 52, 3366 - 3376).

[0115] The aniline of formula (II) required for the preparation of the biguanide of formula (VII) is commercially available, already described in the literature, or can be prepared according to known literature procedures.

[0116] In one embodiment of the invention, the composition according to the invention comprises at least one compound of formula (I) and at least one further active compound B (herbicide B).

[0117] According to a first embodiment of the invention, the composition contains at least one inhibitor of lipid biosynthesis (herbicide b1). These are compounds that inhibit the biosynthesis of lipids. The inhibition of lipid biosynthesis can be affected by either inhibition of acetyl-CoA carboxylase (hereinafter referred to as ACC herbicide) or a different mechanism of action (hereinafter referred to as non-ACC herbicide). ACC herbicides belong to group A (or group 1) of the HRAC classification system, while non-ACC herbicides belong to group N (or now group 15) of the HRAC classification.

[0118] According to a second embodiment of the present invention, the composition contains at least one ALS inhibitor (herbicide b2). The herbicidal activity of these compounds is based on the inhibition of acetolactate synthase and thus on the inhibition of branched-chain amino acid biosynthesis. These inhibitors belong to group B (or 2) of the HRAC classification system.

[0119] According to a third embodiment of the present invention, the composition contains at least one photosynthesis inhibitor (herbicide b3). The herbicidal activity of these compounds is based on the inhibition of the plant's photosystem II (so-called PSII inhibitors, groups C1 (or group 5), C2 (group 5), and C3 (group 6) of the HRAC classification), or on the bypass of electron transport in the plant's photosystem I (so-called PSI inhibitors, group D (or group 22) of the HRAC classification), and thus on the inhibition of photosynthesis. Among these, PSII inhibitors are preferred.

[0120] According to a fourth embodiment of the present invention, the composition contains at least one protoporphyrinogen-IX-oxidase inhibitor (herbicide b4). The herbicidal activity of these compounds is based on the inhibition of protoporphyrinogen-IX-oxidase. These inhibitors belong to group E of the HRAC classification system.

[0121] According to a fifth embodiment of the present invention, the composition contains at least one albinotic herbicide (herbicide b5). The herbicidal activity of these compounds is based on the inhibition of carotenoid biosynthesis. These include compounds that inhibit carotenoid biosynthesis by inhibiting phytoene desaturase (so-called PDS inhibitors, group F1 (group 12) of the HRAC classification), compounds that inhibit 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 (group 27) of the HRAC classification), compounds that inhibit DOX synthase (group F4 (group 13) of the HRAC classification), and compounds that inhibit carotenoid biosynthesis by an unknown mechanism of action (albinotic agents - those with unknown sites of action (unknown target), group F3 (groups 32 + 33) of the HRAC classification).

[0122] According to a sixth embodiment of the present invention, the composition contains at least one EPSP synthase inhibitor (herbicide b6). The herbicidal activity of these compounds is based on the inhibition of enolpyruvylshikimate 3-phosphate synthase, and thus the inhibition of amino acid biosynthesis in plants. These inhibitors belong to group G (9) of the HRAC classification system.

[0123] According to a seventh embodiment of the present invention, the composition contains at least one glutamine synthetase inhibitor (herbicide b7). The herbicidal activity of these compounds is based on the inhibition of glutamine synthetase, and thus the inhibition of amino acid biosynthesis in plants. These inhibitors belong to group H (10) of the HRAC classification system.

[0124] According to an eighth embodiment of the present invention, the composition contains at least one DHP synthase inhibitor (herbicide b8). The herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthase. These inhibitors belong to group I (18) of the HRAC classification system.

[0125] According to the ninth embodiment of the present invention, the composition contains at least one mitotic inhibitor (herbicide b9). The herbicidal activity of these compounds is based on the inhibition of microtubule formation or tissue disruption or inhibition, and thus the inhibition of mitosis. These inhibitors belong to groups K1(3) and K2(23) of the HRAC classification system. Among these, compounds of group K1, particularly dinitroaniline and andicafolin, are preferred.

[0126] According to the tenth embodiment of the present invention, the composition contains at least one VLCFA inhibitor (herbicide b10). The herbicidal activity of these compounds is based on the inhibition of the synthesis of very long chain fatty acids, and thus the disruption or inhibition of cell division in plants. These inhibitors belong to group K3(15) of the HRAC classification system.

[0127] According to the eleventh embodiment of the present invention, the composition contains at least one cellulose biosynthesis inhibitor (herbicide b11). The herbicidal activity of these compounds is based on the inhibition of cellulose biosynthesis, and thus the inhibition of cell wall synthesis in plants. These inhibitors belong to group L(29) of the HRAC classification system.

[0128] According to the twelfth embodiment of the present invention, the composition contains at least one uncoupling herbicide (herbicide b12). The herbicidal activity of these compounds is based on the disruption of cell membranes. These inhibitors belong to group M(24) of the HRAC classification system.

[0129] According to the thirteenth embodiment of the present invention, the composition contains at least one auxin herbicide (herbicide b13). These include compounds that mimic auxin, i.e., plant hormones, and affect plant growth. These compounds belong to group O(4) of the HRAC classification system.

[0130] According to the 14th embodiment of the present invention, the composition contains at least one auxin transport inhibitor (herbicide b14). The herbicidal activity of these compounds is based on the inhibition of auxin transport in plants. These compounds belong to group P(19) of the HRAC classification system.

[0131] For the classification of a given mode of action and active substances, see, for example, "HRAC, Classification of Herbicides According to Mode of Action", http: / / www.plantprotection.org / hrac / MOA.html).

[0132] Preferred compositions according to the invention comprise at least one herbicide B selected from herbicides of classes b1, b2, b3, b4, b5, b6, b7, b9, b10, b13, and b14.

[0133] Particularly preferred compositions according to the invention comprise at least one herbicide B selected from herbicides of classes b1, b4, b5, b6, b7, b10, and b13.

[0134] Particularly preferred compositions according to the invention comprise at least one herbicide B selected from herbicides of classes b4 and b10.

[0135] Examples of herbicide B that can be used in combination with the compound of formula (I) according to the invention are as follows: b1) Those selected from the group of lipid biosynthesis inhibitors: ACC herbicides, such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); Methyl 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate (CAS 1312337-51-1); Methyl 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate; Methyl 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate (CAS 1312340-83-2); Methyl 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate (CAS 1033760-58-5); and non-ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, thiocarbazil, triallate and vernolate; b2) Those selected from the group of ALS inhibitors: Sulfonylureas, for example, amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cycloxysulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl,nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl, and tritosulfuron, Imidazolinones, for example, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazakinin, and imazethapyr, triazolopyrimidine herbicides, and sulfonanilides, for example, chloransulam, chloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan, and pyroxasulam, Pyrimidinylbenzoic acids, such as bispyribac, bispyribac sodium, pyribenzoxim, pyriftalid, pyriflubenzoxin, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid 1-methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8), Sulfonylaminocarbonyltriazolinone herbicides, such as flucarbazone, flucarbazone sodium, propoxycarbazone, propoxycarbazone sodium, thiencarbazone and thiencarbazone methyl; and triafamone. Among these, a preferred embodiment of the present invention relates to a composition containing at least one imidazolinone herbicide. b3) Those selected from the group of photosynthesis inhibitors: Amicarbazone, an inhibitor of photosystem II, such as 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-Dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1), triazine herbicides including chlorotriazine, triazinone, triazinedione, methylthiotriazine and pyridazinone, such as ametryn, atrazine, chloridazon, cyanazine, desmetryn, dimetamethryn, hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryn and trietazine, aryl ureas, such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metiamuron, metabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiaziduron, phenylcarbamates, such as desmedipham, carbutilate, fenmedipham, fenmedipham-ethyl, nitrile herbicides, such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uracils, such as bromacil, lenacil and terbacil, and bentazone and bentazone-sodium, pyridate, pyridafol, pentachlorol and propanil and inhibitors of photosystem I, such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimethylsulfate. Among these, preferred embodiments of the present invention relate to compositions containing at least one aryl urea herbicide. Among these, also preferred embodiments of the present invention relate to compositions containing at least one triazine herbicide. Among these, also preferred embodiments of the present invention relate to compositions containing at least one nitrile herbicide., b4) Those selected from the group of protoporphyrinogen-IX oxidase inhibitors: Acefyllorfen, acefyllorfen-sodium, azafenidin, bencarbazone, benzfendizone, biphenox, butaphenacil, carfentrazone, carfentrazone-ethyl, chromomethoxyphen, chlorophthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenoxymasyl, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluroglycofen, fluroglycofen-ethyl, fluthiacet, fluthiacet-methyl, homomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, propiconazole, pyraclonil, pyraflufen, pyraflufen-ethyl, safufenacil, sulfentrazone, thidiazimin, thiafenacil, triflumizoxazin, epirifene, N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4),, Methyl 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-acetate (CAS 1970221-16-9), methyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetate (CAS 2158274-96-3), ethyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetate (CAS 2158274-50-9), methyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenoxy]-2-pyridyl]oxy]acetate (CAS 2271389-22-9), ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4), methyl 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridyl]oxy]acetate (CAS 2158275-73-9), ethyl 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridyl]oxy]acetate (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-Dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS 2158276-22-1);, Ethyl 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazolecarboxylate (CAS 1949837-17-5); b5) Those selected from the group of albinotic herbicides: PDS inhibitors: Beflubutamid, Diflufenican, Fluridone, Flurochloridone, Flurtamon, Norflurazon, Picolinafen, 4-(3-Trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), Limisoxafen, HPPD inhibitors: Benzobicyclon, Benzofenap, Bicyclopyrone, Chromazone, Fenquinotrione, Isoxaziflutole, Mesotrione, Oxotrione (CAS 1486617-21-3), Pyrazosulfuron, Pyrazolate, Pyrazoxyfen, Sulcotrione, Tefuryltrione, Tembotrione, Topramezone, Bipyrazone, Fenpyrazone, Siprafuorone, Tripyrasulfone, Benquitrione, Dioxopyritrione; Albifying agents, those with unknown site of action (unknown target): Acifluorfen, Amitrole, Fluometuron, 2-Chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), Bixlozone, and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7), Brochlorozone, Flusulfinam, Iptacoprid, Pyraquinate b6) Those derived from the group of EPSP synthase inhibitors: Glyphosate, Glyphosate-isopropylammonium, Glyphosate-potassium and Glyphosate-trimesium (Sulphosate); b7) Derived from the group of glutamine synthetase inhibitors: bilanafos (bialaphos), bilanafos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium, and glufosinate-P-ammonium. b8) Derived from the group of DHP synthase inhibitors: asulam; b9) Selected from the group of mitotic inhibitors: Compounds of group K1: dinitroanilines, such as benfluralin, butralin, dinotramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, and trifluralin, phosphoramidates, such as amiprophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides, such as chlorothal, chlorothal-dimethyl, pyridines, such as dithiopyr and thiazopyr, benzamides, such as propyzamide and tebutam; Compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, and propham, among which the compounds of group K1, particularly dinitroanilines and isocarbophos, are preferred. b10) Selected from the group of VLCFA inhibitors: Chloroacetamides, such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor, and tenilchlor, oxyacetanilides, such as flufenacet and mefenacet, acetanilides, such as diphenamid, napropanilide, napropamide, and napropamide-M, tetrazolinones, such as fentrazamide, and other herbicides, such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, dimethsulfazet, and isoxazoline compounds of formulas II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8, and II.9

Chemical formula

[0136] Preferred herbicide B that can be used in combination with the compound of formula (I) according to the present invention is as follows: b1) Derived from the group of lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, sethoxydim, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, traloxydim, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2);Methyl 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate (CAS 1312337-51-1); Methyl 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate; Methyl 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate (CAS 1312340-83-2); Methyl 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate (CAS 1033760-58-5); Esprocarb, prosulfocarb, thiobencarb, and triallate; b2) Those derived from the group of ALS inhibitors: Bensulfuron-methyl, bispyribac-sodium, cyclosulfamuron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazakine, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron,nicosulfuron, penoxsulam, propoxycarbazone-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxasulfone, rimsulfuron, sulfosulfuron, thiencarbazone-methyl, tritosulfuron and triafamone; b3) Derived from the group of photosynthesis inhibitors: ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat-dichloride, propanil, terbutryn, terbutylamine, 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1); b4) Derived from the group of protoporphyrinogen-IX oxidase inhibitors: cyclopyranyl, flumioxazin, oxyfluorfen, pyraflufen, pyraflufen-ethyl, safufenacil, sulfentrazone, triflumidoxazin, epirifene, 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isindole-1,3-dione (CAS 1300118-96-0), and 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-acetate (CAS 1970221-16-9), methyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetate (CAS 2158274-96-3), ethyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetate (CAS 158274-50-9), methyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenoxy]-2-pyridyl]oxy]acetate (CAS 2271389-22-9), ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-[1,2,4-Triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4), methyl 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetate (CAS 2158275-73-9), ethyl 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]acetate (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS 2158276-22-1);, Ethyl 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazolecarboxylate (CAS 1949837-17-5); b5) Derived from the group of albinizing herbicides: Amitrole, Bicyclopyrone, Chromazone, Diflufenican, Fenquinotrione, Flumetsulam, Flurochloridone, Isoxaziflutole, Mesotrione, Oxotrione (CAS1486617-21-3), Picolinafen, Sulcotrione, Tefuryltrione, Tebuthiuron, Topramezone, 2-Chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS1361139-71-0), Bixlozone, 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS81778-66-7), Limisoxafen, Bromoxynil, Fluthiacet-methyl, Iptacoprid, and Pyraclonil; b6) Derived from the group of EPSP synthase inhibitors: Glyphosate, Glyphosate-isopropylammonium, and Glyphosate-trimesium (Sulphosate); b7) Derived from the group of glutamine synthetase inhibitors: Glufosinate, Glufosinate-P, and Glufosinate-ammonium; b9) Derived from the group of mitosis inhibitors: Pendimethalin, Trifluralin, and Iprodione b10) Derived from the group of VLCFA inhibitors: Acetochlor, Cafestrol, Dimethenamid-P, Fentrazamide, Flufenacet, Mefenacet, Metazachlor, Metolachlor, S-Metolachlor, Phenoxysulfone, Ipfencarbazone, and Pyroxasulfone; Similarly, the isoxazoline compounds of the above formulas II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8, and II.9 are preferred; b11) Derived from the group of cellulose biosynthesis inhibitors: Indaziflam, Isoxaben, and Triaziflam; b13) Derived from the group of auxin herbicides: 2,4-D and its salts and esters, such as clacyfos, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and esters, clopyralid and its salts and esters, dicamba and its salts and esters, flupirauxifene, fluroxypyr-meptyl, halauxifen, halauxifen-methyl, cinchonaclor, cinmethylin, florpyrauxifene, florpyrauxifene-benzyl (CAS 1390661-72-9), 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6), and flucraminopyril; b14) Derived from the group of auxin transport inhibitors: flucraminopyril, diflufenzoppil, and diflufenzoppil-sodium; b15) Derived from the group of other herbicides: simetryn, dymon (= dimefuron), indanofan, oxadiargyl, tetflupyrolimet, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS 2414510-21-5).

[0137] According to another preferred embodiment of the present invention, the composition, in addition to the compound of formula (I), particularly contains at least one, especially exactly one, herbicidally active compound selected from the group consisting of clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, metamifop, pinoxaden, profoxydim, Sethoxydim, tepraloxydim, traloxydim, esprocarb, ethofumesate, molinate, prosulfocarb, thiobencarb, and triallate, derived from group b1).

[0138] According to another preferred embodiment of the present invention, in addition to the compound of formula (I), the composition comprises, in particular, at least one, especially exactly one, herbicidally active compound selected from the group consisting of bensulfuron-methyl, bispyribac-sodium, chloransulam-methyl, chlorosulfuron, chlormuron, cyclosulfamuron, diclosulam, florasulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapic-isopropylammonium, imazapyr, imazapyr-ammonium, imazethapyr-isopropylammonium, imazakine, imazakine-ammonium, imazethapyr, imazethapyr-ammonium, imazethapyr-isopropylammonium, imazosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, metosulam,nicosulfuron, penoxsulam, propoxycarbazone-sodium, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyroxasulfone, propyrisulfuron, rimsulfuron, sulfosulfuron, thifensulfuron-methyl, tribenuron-methyl, tritosulfuron and triafamone.

[0139] According to another preferred embodiment of the present invention, in addition to the compound of formula (I), the composition comprises, in particular, at least one, especially exactly one, herbicidally active compound selected from the group consisting of ametryn, atrazine, bentazone, bromoxynil, bromoxynil octanoate, bromoxynil heptanoate, bromoxynil potassium, diuron, fluometuron, hexazinone, isoproturon, linuron, metamitron, metribuzin, paraquat dichloride, propanil, simazine, terbutryn, and terbutylazine.

[0140] According to another preferred embodiment of the present invention, in addition to the compound of formula (I), the composition comprises at least one, particularly exactly one, active compound from the group consisting of herbicidally active compounds selected from the group consisting of acifluorfen, butaphenacil, carfentrazone-ethyl, flumioxazin, homosafen, oxadiargyl, oxyfluorfen, pyraflufen, pyraflufen-ethyl, sulfufenacil, sulfentrazone, trifludimoxazin, epirifene, 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazolecarboxylic acid ethyl ester (CAS 1949837-17-5), and flufenoxymasyl, particularly from group b4).

[0141] According to another preferred embodiment of the present invention, in addition to the compound of formula (I), the composition comprises at least one, particularly exactly one, active compound from the group consisting of herbicidally active compounds selected from the group consisting of amitrole, benzobicyclon, bicyclopyrone, chromazone, diflufenican, fenquinotrione, fluometuron, flurochloridone, isoxaflutole, mesotrione, norflurazon, oxotrione (CAS 1486617-21-3), picolinafen, sulcotrione, tefuryltrione, tembotrione, topramezone, topramezone-sodium, 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), bixlozone, 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7) rimsulfuron, and broxazon, flusulfinam, iptriazopyrid, pyraquinate, particularly from group b5).

[0142] According to another preferred embodiment of the present invention, the composition, in addition to the compound of formula (I), comprises at least one, in particular exactly one, herbicidally active compound selected from the group consisting of glyphosate, glyphosate-ammonium, glyphosate-dimethylammonium, glyphosate-isopropylammonium, and glyphosate-trimesium (sulfosate) and glyphosate-potassium, which is derived from group b6).

[0143] According to another preferred embodiment of the present invention, the composition, in addition to the compound of formula (I), comprises at least one, in particular exactly one, herbicidally active compound selected from the group consisting of glufosinate, glufosinate-ammonium, glufosinate-P, and glufosinate-P-ammonium, which is derived from group b7).

[0144] According to another preferred embodiment of the present invention, the composition, in addition to the compound of formula (I), comprises at least one, in particular exactly one, herbicidally active compound selected from the group consisting of pendimethalin and trifluralin, which is derived from group b9).

[0145] According to another preferred embodiment of the present invention, the composition, in addition to the compound of formula (I), comprises at least one, in particular exactly one, herbicidally active compound selected from the group consisting of acetochlor, butachlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, phenoxysulfone, ipfencarbazone, and pyroxasulfone, which is derived from group b10).

[0146] According to another preferred embodiment of the present invention, the composition, in addition to the compound of formula (I), comprises at least one, in particular exactly one, herbicidally active compound, in particular indaziflam, isoxaben, and triaziflam, which is derived from group b11).

[0147] According to another preferred embodiment of the present invention, in addition to the compound of formula (I), the composition comprises, in particular, at least one, especially exactly one, herbicidally active compound selected from the group consisting of 2,4-D, 2,4-D-isobutyl, 2,4-D-dimethylammonium, 2,4-D-N,N,N-trimethylethanolammonium, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid-methyl, aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium, clopyralid, clopyralid-methyl, clopyralid-olamine, dicamba, dicamba-butyl, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium, dicamba-trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine, dicamba-diethylenetriamine, flopyrauxifen, fluroxypyr, fluroxypyr-meptyl, halauxifen, halauxifen-methyl, MCPA, MCPA-2-ethylhexyl, MCPA-dimethylammonium, cinchonacrine, cinchonacrine-dimethylammonium, cinmeracrine, cinmeracrine-dimethylammonium, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9), 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6), and flucraminopyr.

[0148] According to another preferred embodiment of the present invention, in addition to the compound of formula (I), the composition comprises at least one, especially exactly one, herbicidally active compound selected from the group consisting of diflufenzoppil, diflufenzoppil-sodium, dimefuron, indanofan, and diflufenzoppil-sodium, which is derived from group b14).

[0149] According to another preferred embodiment of the present invention, in addition to the compound of formula (I), the composition comprises at least one, in particular exactly one, herbicidally active compound selected from the group consisting of, inter alia, simetryn, dymron (= daimuron), indanofan, oxadiargyl, tetflupyrolimet, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS 2414510-21-5) of group b15).

[0150] According to another preferred embodiment of the present invention, in addition to the compound of formula (I), the composition comprises at least one, in particular exactly one, antidote C selected from the group consisting of, inter alia, benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4).

[0151] According to another preferred embodiment of the present invention, in addition to the compound of formula (I), the composition comprises at least one, in particular exactly one, herbicidally active compound selected from the following: b1): clethodim, clodinafop-propargyl, cyhalofop-butyl, metamifop, profoxydim, quizalofop-ethyl, sethoxydim, prosulfocarb, triallate; b2): mesosulfuron, pyrazosulfuron-ethyl, imazamox, imazethapyr, diclosulam, penoxsulam, pyroxasulfone, bispyribac-sodium, thifensulfuron-methyl; and triafamone; b3): atrazine, metribuzin, terbuthylazine, bromoxynil and its salts and esters, bentazone and bentazone-sodium, propanil. b4): Flumioxazin, S-ethyl 2-(2-((3-chloro-6-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-5-fluoro-2-pyridinyl)oxy)phenoxy)acetate (CAS 2158274-50-9), and flufenoxymasyl. b5): Diflumetican, picolinafen, chromazone, isoxaflutole, mesotrione, topramezone, acifluorfen, bixlozone. b6) and b7): Glyphosate, glufosinate, glufosinate-P, glufosinate-ammonium, and glufosinate-P-ammonium. b9): Trifluralin, propyzamide: b10): Butachlor, dimethenamid-P, metolachlor, pretilachlor, flufenacet, pyroxasulfone. b11): Indaziflam, isoxaben. b13): 2,4-D and its salts and esters, dicamba and its salts and esters. b15): Simetryn, cyclopyrimorate, tetflupyrolimet, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS 2414510-21-5).

[0152] Particularly preferred herbicide B is the herbicide B defined above; in particular, herbicides B.1 to B.215 listed in Table B below:

[0153]

Table 7

[0154]

Table 8

[0155]

Table 9

[0156]

Table 10

[0157]

Table 11

[0158] In another embodiment of the present invention, the composition according to the present invention comprises at least one compound of formula (I) and at least one antidote C.

[0159] The antidote is a compound that prevents or reduces damage to useful plants without significantly affecting the herbicidal action of the herbicidal active ingredient of the composition against unwanted plants. They can be applied either before sowing (e.g., to seeds, buds or seedlings) or either pre-emergence or post-emergence application to useful plants. The antidote, and the compound of formula (I), and / or herbicide B can be applied simultaneously or sequentially.

[0160] Suitable antidotes are, for example, (quinolin-8-oxy)acetic acid, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, 4,5-dihydro-5,5-diallyl-3-isoxazolecarboxylic acid, dichloroacetamide, α-oximinophenylacetonitrile, acetophenoxime, 4,6-dihalo-2-phenylpyrimidine, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamide, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acid, phosphorothiolate and N-alkyl-O-phenylcarbamate and their agriculturally acceptable salts and their agriculturally acceptable derivatives such as amides, esters and thioesters, provided that they have an acid group.

[0161] Examples of preferred antidote C include benoxacol, cloctol, cimetrinil, cyprosulfamide, dichloramide, diclomezine, dietholate, fenchlorazole, fenchlorim, flurazole, flucxyphenim, furilazole, isoxadifen, mefenpyr, mefenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4), metcamifene, and BPCMS (CAS 54091-06-4).

[0162] Particularly preferred antidote C includes benoxacol, cloctol, cyprosulfamide, dichloramide, fenchlorazole, fenchlorim, flurazole, flucxyphenim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4), and metcamifene.

[0163] Particularly preferred antidote C includes cloctol, cyprosulfamide, fenclori, furilazole, isoxadifen-ethyl, mefenpyr-diethyl.

[0164] As component C, a particularly preferred antidote C which is a constituent of the composition according to the present invention is the antidote C defined above; in particular, antidote C.1 to C.17 listed in Table C below:

[0165]

Table 12

[0166] b1) to b15) The active compounds B and C of the group are known herbicides and antidotes. For example, refer to The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CAS No. 52836-31-4] is also called R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also called AD-67 and MON4660.

[0167] The assignment of each active compound to its mode of action is based on current knowledge. If several modes of action apply to one active compound, this substance is assigned to only one mode of action.

[0168] The active compounds B and C having a carboxyl group can be used in the compositions according to the invention in acid form, in the form of an agriculturally suitable salt as described above, or otherwise in the form of an agriculturally acceptable derivative.

[0169] In the case of dicamba, suitable salts include those in which the counterion is an agriculturally acceptable cation. For example, suitable salts of dicamba are dicamba-sodium, dicamba-potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of suitable esters are dicamba-methyl and dicamba-butyl.

[0170] Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4-D-sodium, and 2,4-D-N,N,N-trimethylethanolammonium (2,4-D choline). Examples of suitable esters of 2,4-D are 2,4-D-butyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clathrifos.

[0171] Suitable salts of 2,4-DB are, for example, 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dimethylammonium. Suitable esters of 2,4-DB are, for example, 2,4-DB-butyl and 2,4-DB-isooctyl.

[0172] Suitable salts of dichlorprop are, for example, dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop-butyl and dichlorprop-isooctyl.

[0173] Suitable salts and esters of MCPA include MCPA-butyl, MCPA-butyl, MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isooctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, and MCPA-trolamine.

[0174] A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB is MCPB-ethyl.

[0175] Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2-hydroxypropyl)ammonium. An example of a suitable ester of clopyralid is clopyralid-methyl.

[0176] Examples of suitable esters of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1-methylethyl, where fluroxypyr-meptyl is preferred.

[0177] Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable ester of picloram is picloram-isooctyl.

[0178] A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are, for example, triclopyr-ethyl and triclopyr-butotyl.

[0179] Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium and 2,3,6-TBA-sodium.

[0180] Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid-dimethylammonium and aminopyralid-tris(2-hydroxypropyl)ammonium.

[0181] Suitable salts of glyphosate are, for example, glyphosate-ammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium as well as ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate).

[0182] A suitable salt of glufosinate is, for example, glufosinate-ammonium.

[0183] Suitable salts of glufosinate-P are, for example, glufosinate-P-ammonium.

[0184] Suitable salts and esters of bromoxynil are, for example, bromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.

[0185] Suitable salts and esters of ioxynil are, for example, ioxynil-octanoate, ioxynil-potassium and ioxynil-sodium.

[0186] Suitable salts and esters of mecoprop include mecoprop-butyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethazil, mecoprop-2-ethylhexyl, mecoprop-isooctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.

[0187] Suitable salts of mecoprop-P are, for example, mecoprop-P-butyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.

[0188] Suitable salts of diflufenzo pyr are, for example, diflufenzo pyr-sodium.

[0189] Suitable salts of naphthal am are, for example, naphthal am-sodium.

[0190] Suitable salts and esters of aminocyclopyrachlor are, for example, aminocyclopyrachlor-dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor-triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium.

[0191] A suitable salt of cinchlorac is, for example, cinchlorac-dimethylammonium.

[0192] A suitable salt of cinmethylin is, for example, cinmethylin-dimethylammonium.

[0193] A suitable salt of imazamox is, for example, imazamox-ammonium.

[0194] A suitable salt of imazapic is, for example, imazapic-ammonium and imazapic-isopropylammonium.

[0195] A suitable salt of imazapyr is, for example, imazapyr-ammonium and imazapyr-isopropylammonium.

[0196] A suitable salt of imazaquin is, for example, imazaquin-ammonium.

[0197] A suitable salt of imazethapyr is, for example, imazethapyr-ammonium and imazethapyr-isopropylammonium.

[0198] A suitable salt of topramezone is, for example, topramezone-sodium.

[0199] According to a preferred embodiment of the present invention, the composition comprises, as the herbicidally active compound B or component B, at least one, preferably exactly one, herbicide B.

[0200] According to another preferred embodiment of the present invention, the composition comprises, as the herbicidally active compound B or component B, at least two, preferably exactly two, different herbicides B.

[0201] According to another preferred embodiment of the present invention, the composition comprises, as the herbicidally active compound B or component B, at least three, preferably exactly three, different herbicides B.

[0202] According to another preferred embodiment of the present invention, the composition contains at least one, preferably exactly one, antidote C as the detoxifying component C or component C.

[0203] According to another preferred embodiment of the present invention, the composition contains at least one, preferably exactly one, herbicide B as component B and at least one, preferably exactly one, antidote C as component C.

[0204] According to another preferred embodiment of the present invention, the composition contains at least two, preferably exactly two, different herbicides B from each other and at least one, preferably exactly one, antidote C as component C.

[0205] According to another preferred embodiment of the present invention, the composition contains at least three, preferably exactly three, different herbicides B from each other and at least one, preferably exactly one, antidote C as component C.

[0206] In this case and hereinafter, the term "binary composition" includes a composition containing one or more (e.g., one, two, or three) active compounds of formula (I) and either one or more (e.g., one, two, or three) herbicides B or one or more (e.g., one, two, or three) antidotes C.

[0207] Correspondingly, the term "ternary composition" includes a composition containing one or more (e.g., one, two, or three) active compounds of formula (I), one or more (e.g., one, two, or three) herbicides B, and one or more (e.g., one, two, or three) antidotes C.

[0208] In a binary composition containing at least one compound of formula (I) as component A and at least one herbicide B, the weight ratio of the active compound A:B is generally in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1, and particularly preferably in the range of 1:75 to 75:1.

[0209] In a binary composition comprising at least one compound of formula (I) as component A and at least one antidote C, the weight ratio of the active compound A:C is generally in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1, and particularly preferably in the range of 1:75 to 75:1.

[0210] In a ternary composition comprising at least one compound of formula (I) as component A, at least one herbicide B, and at least one antidote C, the relative weight ratio of component A:B is generally in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1, and particularly preferably in the range of 1:75 to 75:1; the weight ratio of component A:C is generally in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1, and particularly preferably in the range of 1:75 to 75:1; and the weight ratio of component B:C is generally in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1, and particularly preferably in the range of 1:75 to 75:1. The weight ratio of component A + B to component C is preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1, and particularly preferably in the range of 1:75 to 75:1.

[0211] The weight ratios of the individual components in the preferred mixtures described below are within the above ranges, particularly within the particularly preferred ranges.

[0212] Particularly preferred are the following compositions comprising the compounds of defined formula (I) and the substances defined in each row of Table 1: Especially preferred are those comprising the compounds of formula (I) defined as the herbicidal active compound only and the substances defined in each row of Table 1. Most preferred are those comprising the compounds of formula (I) defined as the active compound only and the substances defined in each row of Table 1.

[0213] Particularly preferred is the formula

Chemical formula

[0214]

Table 13

[0215]

Table 14

[0216]

Table 15

[0217]

Table 16

[0218]

Table 17

[0219]

Table 18

[0220]

Table 19

[0221]

Table 20

[0222]

Table 21

[0223]

Table 22

[0224]

Table 23

[0225]

Table 24

[0226]

Table 25

[0227]

Table 26

[0228]

Table 27

[0229]

Table 28

[0230]

Table 29

[0231]

Table 30

[0232]

Table 31

[0233]

Table 32

[0234]

Table 33

[0235]

Table 34

[0236]

Table 35

[0237]

Table 36

[0238]

Table 37

[0239]

Table 38

[0240]

Table 39

[0241]

Table 40

[0242]

Table 41

[0243]

Table 42

[0244]

Table 43

[0245]

Table 44

[0246]

Table 45

[0247]

Table 46

[0248]

Table 47

[0249]

Table 48

[0250]

Table 49

[0251]

Table 50

[0252]

Table 51

[0253]

Table 52

[0254]

Table 53

[0255]

Table 54

[0256]

Table 55

[0257]

Table 56

[0258]

Table 57

[0259]

Table 58

[0260] The specific numerical values for each single composition can be estimated as follows: Composition 1.200 contains, for example, compound (I.a.20) and symetrylin (B.200) (see Table 1, entry 1.200; and Table B, entry B.200). Composition 2.200 contains, for example, compound (I.a.19) (see the definitions of Compositions 2.1 to 2.3887 below) and symetrylin (B.200) (see Table 1, entry 1.200; and Table B, entry B.200). Composition 7.200 contains, for example, imazapyr (B.35) (see the definitions of Compositions 7.1 to 7.3887 below), compound (I.a.20), and symetrylin (B.200) (see Table 1, entry 1.200; and Table B, entry B.200).

[0261] Also, particularly preferred is the formula

Chemical formula

[0262] Also particularly preferred are compositions 3.1 to 3.3887 comprising the compound of the formula

Chemical formula

[0263] Also particularly preferred are compositions 4.1 to 4.3887 comprising the compound of the formula

Chemical formula

[0264] The present invention also relates to pesticidal compositions comprising an adjuvant and at least one compound according to the present invention.

[0265] The pesticidal composition comprises at least one composition according to the present invention in a pest-killing effective amount. The term "effective amount" refers to the amount of the active ingredient that is sufficient for controlling unwanted plants, particularly for controlling unwanted plants in crops (i.e., cultivated plants) and does not cause substantial damage to the plants being treated. Such an amount can vary widely and depends on various factors, such as the plant to be controlled, the crop or material being treated, the climatic conditions, and the specific composition used according to the present invention.

[0266] Compound A and optionally B and / or C, their N-oxides, salts, or derivatives can be converted into conventional types of pesticidal compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples of types of pesticidal compositions are suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, troches, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), pressings (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations (e.g., GF) for the treatment of plant seedlings such as seeds. These and further types of pesticidal compositions are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No.2,6 th Ed.May 2008, CropLife International.

[0267] The pesticidal compositions are prepared by known methods, for example, as described in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0268] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration promoters, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreezing agents, defoamers, colorants, tackifiers, and binders.

[0269] Suitable solvents and liquid carriers are water and organic solvents such as medium to high boiling mineral oil fractions such as kerosene, diesel oil; oils derived from plants or animals; aliphatic, cyclic and aromatic hydrocarbons such as toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones such as cyclohexanone; esters such as lactate, carbonate, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides such as N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

[0270] Suitable solid carriers or fillers are mineral earths such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides such as cellulose, starch; fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products derived from plants such as cereal bran, bark meal, wood meal, nut meal and mixtures thereof.

[0271] Suitable surfactants are surface active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration promoters, protective colloids or adjuvants. Examples of surfactants are described in McCutcheon’s, Vol. 1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[0272] Suitable anionic surfactants are the alkali salts, alkaline earth salts or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalene and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohols or alkylphenol ethoxylates.

[0273] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters alkoxylated with 1 to 50 equivalents of ethylene oxide and / or propylene oxide, preferably ethylene oxide, for alkoxylation. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinyl pyrrolidone, vinyl alcohol, or vinyl acetate.

[0274] Suitable cationic surfactants are quaternary surfactants, for example, quaternary ammonium compounds having one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are A-B or A-B-A type block polymers containing blocks of polyethylene oxide and polypropylene oxide, or A-B-C type block polymers containing alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are polyacrylic acid or alkali salts of comb-shaped polymers of polyacids. Examples of polybases are polyvinylamine or polyethyleneamine.

[0275] Suitable adjuvants are compounds that enhance the biological performance of Compound I on the target, although their pesticidal activity per se may be negligible or even non-existent. Examples include surfactants, mineral oils or vegetable oils, and other auxiliaries. Further examples are described in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[0276] Suitable thickeners are polysaccharides (e.g., xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0277] Suitable bactericides are bronopol and isothiazolinone derivatives, for example, alkyl isothiazolinone and benzisothiazolinone.

[0278] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

[0279] Suitable defoamers are silicones, long-chain alcohols and salts of fatty acids.

[0280] Suitable colorants (e.g., red, blue, or green) are low water-soluble pigments and water-soluble dyes. Examples include inorganic colorants (e.g., iron oxide, titanium oxide, hexacyanoferrate), and organic colorants (e.g., alizarin, azo, and phthalocyanine colorants).

[0281] Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biological or synthetic waxes, and cellulose ethers.

[0282] Examples of the types of pesticide compositions and their preparation methods are as follows: i) Water-soluble concentrates (SL, LS) Dissolve 10 - 60 wt% of the composition according to the present invention and 5 - 15 wt% of a wetting agent (e.g., alcohol alkoxylate) in the remaining amount of water and / or water-soluble solvent (e.g., alcohol) up to 100 wt%. The active substance dissolves when diluted with water. ii) Dispersible concentrates (DC) Dissolve 5 - 25 wt% of the composition according to the present invention and 1 - 10 wt% of a dispersant (e.g., polyvinylpyrrolidone) in the remaining amount of organic solvent (e.g., cyclohexanone) up to 100 wt%. A dispersion is obtained when diluted with water. iii) Emulsifiable concentrates (EC) Dissolve 15 - 70 wt% of the composition according to the present invention and 5 - 10 wt% of an emulsifier (e.g., calcium dodecylbenzenesulfonate, castor oil ethoxylate) in the remaining amount of water-insoluble organic solvent (e.g., aromatic hydrocarbon) up to 100 wt%. An emulsion is obtained when diluted with water. iv) Emulsions (EW, EO, ES) Dissolve 5 - 40 wt% of the composition according to the present invention and 1 - 10 wt% of an emulsifier (e.g., calcium dodecylbenzenesulfonate, castor oil ethoxylate) in 20 - 40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbon). Introduce this mixture into the remaining amount of water up to 100 wt% by an emulsifier to obtain a homogeneous emulsion. An emulsion is obtained when diluted with water. v) Suspension (SC, OD, FS) In a stirred ball mill, 20 - 60% by weight of the composition according to the invention is added with 2 - 10% by weight of a dispersant and a wetting agent (for example, sodium lignosulfonate and alcohol ethoxylate), 0.1 - 2% by weight of a thickener (for example, xanthan gum) and up to 100% by weight of the balance of water and pulverized to obtain a fine active substance suspension. When diluted with water, a stable suspension of the active substance is obtained. In the case of the FS type, a binder (for example, polyvinyl alcohol) of 40% by weight or less is added. vi) Water - dispersible granules and water - soluble granules (WG, SG) 50 - 80% by weight of the composition according to the invention is added with up to 100% by weight of the balance of a dispersant and a wetting agent (for example, sodium lignosulfonate and alcohol ethoxylate) and finely pulverized, and is prepared as water - dispersible or water - soluble granules by technical equipment (for example, extrusion, spray tower, fluidized bed). When diluted with water, a stable dispersion or solution of the active substance is obtained. vii) Wettable powder (powder) and water - soluble powder (WP, SP, WS) 50 - 80% by weight of the composition according to the invention is added with 1 - 5% by weight of a dispersant (for example, sodium lignosulfonate), 1 - 3% by weight of a wetting agent (for example, alcohol ethoxylate) and 100% by weight of a solid carrier (for example, silica gel) and pulverized in a rotor - stator mill. When diluted with water, a stable dispersion or solution of the active substance is obtained. viii) Gel preparation (GW, GF) In a stirred ball mill, 5 - 25% by weight of the composition according to the invention is added with 3 - 10% by weight of a dispersant (for example, sodium lignosulfonate), 1 - 5% by weight of a thickener (for example, carboxymethyl cellulose) and up to 100% by weight of the balance of water and pulverized to obtain a fine suspension of the active substance. When diluted with water, a stable suspension of the active substance is obtained. iv) Microemulsion (ME) 5 to 20% by weight of the composition according to the invention is added to 5 to 30% by weight of an organic solvent blend (for example, fatty acid dimethylamide and cyclohexanone), 10 to 25% by weight of a surfactant blend (for example, alcohol ethoxylate and arylphenol ethoxylate) and up to 100% of the balance of water. This mixture is stirred for 1 hour to spontaneously form a thermodynamically stable microemulsion. iv) Microcapsule agent (CS) An oil phase containing 5 to 50% by weight of the composition according to the invention, 0 to 40% by weight of a water-insoluble organic solvent (for example, aromatic hydrocarbon), 2 to 15% by weight of an acrylic monomer (for example, methyl methacrylate, methacrylic acid and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (for example, polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5 to 50% by weight of Compound I according to the invention, 0 to 40% by weight of a water-insoluble organic solvent (for example, aromatic hydrocarbon), and an isocyanate monomer (for example, diphenylmethane-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (for example, polyvinyl alcohol). The addition of a polyamine (for example, hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer reaches 1 to 10% by weight. % by weight relates to the entire CS composition. ix) Dustable powder (DP, DS) 1 to 10% by weight of the composition according to the invention is finely pulverized and intimately mixed with up to 100% of the balance of a solid carrier (for example, finely pulverized kaolin). x) Granules (GR, FG) 0.5 to 30% by weight of the composition according to the invention is finely pulverized and associated with up to 100% of the balance of a solid carrier (for example, silicate). Granulation is achieved by extrusion, spray drying, or fluidized bed. xi) Ultra-trace liquid (UL) 1 to 50% by weight of the composition according to the invention is dissolved in up to 100% of the balance of an organic solvent (for example, aromatic hydrocarbon).

[0283] The types i) - xi) of the pesticide compositions may optionally further contain adjuvants such as 0.1 - 1% by weight of a bactericide, 5 - 15% by weight of an antifreeze, 0.1 - 1% by weight of an antifoaming agent, and 0.1 - 1% by weight of a colorant.

[0284] The pesticide composition generally contains 0.01 - 95% by weight, preferably 0.1 - 90% by weight, particularly 0.5 - 75% by weight of an active substance. The active substance is used at a purity of 90% - 100%, preferably 95% - 100% (based on the NMR spectrum).

[0285] Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), wettable powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gel formulations (GF) are usually used for the treatment of plant propagation materials, especially seeds. After diluting the said compositions 2 - 10 times, they provide an active substance concentration of 0.01 - 60% by weight, preferably 0.1 - 40% by weight in the ready-to-use preparations. Application can be carried out before sowing or during sowing.

[0286] The methods of applying the compound of formula (I) and its composition to plant propagation materials, especially seeds, include the methods of film coating, coating, pelleting, dusting, dipping and inter-row application of the propagation materials. Preferably, the compound I or its composition is applied onto the plant propagation materials by a method that does not induce germination, such as seed dressing, pelleting, coating, and dusting.

[0287] Various types of oils, wetting agents, adjuvants, fertilizers, or micronutrients, and further pest control agents (e.g., herbicides, insecticides, fungicides, growth regulators, antidotes) may be added as a premix to the active substance or the composition containing it, or may not be added until immediately before use (tank mixing) where appropriate. These agents can be admixed with the composition according to the invention at a weight ratio of 1:100 - 100:1, preferably 1:10 - 10:1.

[0288] The user usually applies the pesticide composition according to the invention from a predosage device, a knapsack sprayer, a spray tank, a crop spraying aircraft or an irrigation system. Usually, the pesticide composition is formulated with water, a buffer and / or further adjuvants to the desired application concentration, thereby obtaining a ready-to-use spray liquor or pesticide composition according to the invention. Usually, the ready-to-use spray liquor is applied at 20 to 2000 liters, preferably 50 to 400 liters per hectare of agriculturally useful area.

[0289] According to one embodiment, either the individual components of the pesticide composition according to the invention or partially premixed components, for example the compound of formula (I) and / or a pesticidal component comprising an active substance from group B and / or C, are mixed by the user in the spray tank and, if appropriate, further adjuvants and additives may be added.

[0290] In a further embodiment, the individual components of the pesticide composition according to the invention, such as part of a kit or part of a two-component or three-component mixture, are mixed by the user himself in the spray tank and, where appropriate, further adjuvants may be added.

[0291] In a further embodiment, either the individual components of the formulation according to the invention or partially premixed components, for example the compound of formula (I) and a component comprising an active substance from group B and / or C, can be applied together or continuously (for example, after tank mixing).

[0292] Accordingly, a first embodiment of the invention relates to a composition in the form of a pesticide composition which is formulated as a one-part composition comprising at least one active compound of formula (I) or at least one active compound of formula (I) (active compound A) and at least one further active compound selected from herbicide B and antidote C, and also a solid or liquid carrier and, if appropriate, one or more surfactants.

[0293] Accordingly, the second embodiment of the present invention relates to a composition in the form of a pesticidal composition formulated as a two-component composition comprising a first formulation (component) comprising at least one active compound A, a solid or liquid carrier, and, if appropriate, one or more surfactants, and a second component comprising at least one further active compound selected from herbicide B and antidote C, a solid or liquid carrier, and, if appropriate, one or more surfactants.

[0294] Active compound A and at least one further active compound B and / or C can be formulated and applied together or separately, simultaneously or successively, before, during or after emergence of the plants. When applying separately, the order of application of active compounds A, B and / or C is not very important. The only important thing is that at least one active compound A and at least one further active compound B and / or C are present simultaneously at the site of action, i.e. contact or are taken up simultaneously by the plants to be controlled / detoxified.

[0295] The compositions according to the invention are suitable as herbicides. They are suitable per se or as appropriately formulated compositions (pesticidal compositions).

[0296] The compositions according to the invention control the vegetation of non-crop areas very effectively, especially at high application rates. They act against broad-leaved and grass weeds in crops such as wheat, rice, maize, soybean, sugarcane, sunflower and cotton without causing significant damage to the crop plants. This effect is mainly observed at low application rates.

[0297] The compositions according to the invention have excellent herbicidal activity against unwanted vegetation, i.e. against a wide range of economically important harmful monocotyledonous and dicotyledonous weeds. Furthermore, the compositions according to the invention have excellent herbicidal activity against unwanted vegetation which is resistant to compounds of the mode of action comprising, but not limited to, the compounds of classes b1) to b15) as defined above.

[0298] The following are representative examples of monocotyledonous and dicotyledonous weeds that can be controlled by the composition according to the present invention, but the listing is not limited to specific species.

[0299] Preferably, the composition according to the present invention is used for controlling monocotyledonous weeds.

[0300] Examples of monocotyledonous weeds on which the composition according to the present invention acts effectively are selected from Hordeum spp., Echinochloa spp., Poa spp., Bromus spp., Digitaria spp., Eriochloa spp., Setaria spp., Pennisetum spp., Eleusine spp., Eragrostis spp., Panicum spp., Lolium spp., Brachiaria spp., Leptochloa spp., Avena spp., Cyperus spp., Axonopris spp., Sorghum spp., and Melinus spp.

[0301] Preferred examples of monocotyledonous weeds on which the composition according to the present invention acts effectively are selected from the seeds of Hordeum murinum, Echinochloa crus-galli, Poa annua, Bromus rubens L., Bromus rigidus, Bromus secalinus L., Digitaria sanguinalis, Digitaria insularis, Eriochloa gracilis, Setaria faberi, Setaria viridis, Pennisetum glaucum, Eleusine indica, Eragrostis pectinacea, Panicum miliaceum, Lolium multiflorum, Brachiaria platyphylla, Leptochloa fusca, Avena fatua, Cyperus compressus, Cyperus esculentes, Axonopris offinis, Sorghum halapense, and Melinus repens.

[0302] Particularly preferred examples of monocotyledonous weeds on which the composition according to the present invention acts effectively are selected from Echinochloa spp., Digitaria spp., Setaria spp., Eleusine spp., and Brachiarium spp.

[0303] Also preferably, the composition according to the present invention is used for controlling dicotyledonous weeds.

[0304] Examples of dicotyledonous weeds on which the composition according to the invention acts effectively are species of the genus Amaranthus, species of the genus Erigeron, species of the genus Conyza, species of the genus Polygonum, species of the genus Medicago, species of the genus Mollugo, species of the genus Cyclospermum, species of the genus Stellaria, species of the genus Gnaphalium, species of the genus Taraxacum, species of the genus Oenothera, species of the genus Amsinckia, species of the genus Erodium, species of the genus Erigeron, species of the genus Senecio, species of the genus Lamium, species of the genus Kochia, species of the genus Chenopodium, species of the genus Lactuca, species of the genus Malva, species of the genus Ipomoea, species of the genus Brassica, species of the genus Sinapis, species of the genus Urtica, species of the genus Sida, species of the genus Portulaca, species of the genus Richardia, species of the genus Ambrosia, species of the genus Calandrinia, species of the genus Sisymbrium, species of the genus Sesbania, species of the genus Capsella, species of the genus Sonchus, species of the genus Euphorbia, species of the genus Helianthus, species of the genus Coronopus, species of the genus Salsola, species of the genus Abutilon, species of the genus Vicia, species of the genus Epilobium, species of the genus Cardamine, species of the genus Picris) It is selected from the genera of Trifolium spp., Galinsoga spp., Epimedium spp., Marchantia spp., Solanum spp., Oxalis spp., Metricaria spp., Plantago spp., Tribulus spp., Cenchrus spp., Bidens spp., Veronica spp., and Hypochaeris spp.

[0305] Preferred examples of dicotyledonous weeds on which the composition according to the present invention acts effectively are Amaranthus spinosus, Polygonum convolvulus, Medicago polymorpha, Mollugo verticillata, Cyclospermum leptophyllum, Stellaria media, Gnaphalium purpureum, Taraxacum officinale, Oenothera laciniata, Amsinckia intermedia, Erodium cicutarium, Erodium moschatum, Erigeron bonariensis (Conyza bonariensis), Senecio vulgaris, Lamium amplexicaule, Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoea hederacea, Ipomoea lacunose, Brassica nigra, Sinapis arvensis, Urtica dioica, Amaranthus blitoides, Amaranthus retroflexus, Amaranthus hybridus, Amaranthus lividus, Amaranthus palmeri, Amaranthus tuberculatus, Sidaselected from the seeds of Spinacia oleracea, Portulaca oleracea, Richardia scabra, Ambrosia artemisiifolia, Calandrinia caulescens, Sisymbrium irio, Sesbania exaltata, Capsella bursa-pastoris, Sonchus oleraceus, Euphorbia maculate, Euphorbia heterophylla, Helianthus annuus, Coronopus didymus, Salsola tragus, Abutilon theophrasti, Vicia benghalensis L., Epilobium paniculatum, Cardamine spp, Picris echioides, Trifolium spp., Galinsoga spp., Epimedium spp., Marchantia spp., Solanum spp., Oxalis spp., Metricaria matriccarioides, Plantago spp., Tribulus terrestris, Salsola kali, Cenchrus spp., Bidens bipinnata, Veronica spp., and Hypochaeris radicata.

[0306] Particularly preferred examples of dicotyledonous weeds on which the composition according to the invention acts effectively are selected from the species of Amaranthus spp., Erigeron spp., Conyza spp., Kochia spp., and Abutilon spp.

[0307] The composition according to the invention is mainly applied by spraying on the leaf surface of plants. As used herein, the application can be carried out, for example, using conventional spraying techniques with a spray liquid volume in an amount of about 100 to 1000 l / ha (for example, 300 to 400 l / ha), using water as a carrier. The herbicidal composition can also be applied in the form of low-volume spraying, ultra-low-volume spraying, or granules.

[0308] The application of the herbicidal composition according to the invention can be carried out before, during, and / or after the emergence of unwanted plants, preferably during and / or after.

[0309] The herbicidal composition according to the invention can be applied before or after emergence, or together with the seeds of crop plants. By applying the seeds of crop plants pretreated with the composition of the invention, it is also possible to apply the compounds and compositions. If the active compounds A and B, and optionally C, are not sufficiently tolerated by a particular crop plant, the herbicidal composition can be sprayed using an application technique such that the active compounds reach the leaves of unwanted plants growing under the crop or the soil surface of the field but contact the leaves of the sensitive crop as little as possible (post-directed, lay-by).

[0310] In a further embodiment, the composition according to the invention can be applied by treating the seeds. The treatment of the seeds is based on the compound of formula (I) according to the invention or the composition prepared therefrom and includes essentially all procedures well known to those skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multi-layer coating, seed encapsulation, seed dripping and seed pelleting). Herein, the herbicidal composition can be applied diluted or undiluted.

[0311] The term "seed" includes all types of seeds, such as grains, seeds, fruits, tubers, seedlings and the like. Herein, preferably, the term "seed" represents grains and seeds. The seeds used can be the seeds of the above useful plants, but can also be the seeds of transgenic plants or plants obtained by conventional breeding methods.

[0312] Furthermore, the composition of the invention can advantageously be applied alone or in combination with other crop protection agents, such as agents for controlling pests, phytopathogenic fungi or bacteria, or a group of active compounds for regulating growth. Miscibility with inorganic salt solutions used for treating nutrient and trace element deficiencies is also of interest. Phytotoxic oils and oil concentrates can also be added.

[0313] When used in plant protection, the application rates of the active substances without formulation adjuvants, i.e., A and B and, if appropriate, C, are 0.001 to 3 kg per ha, preferably 0.005 to 2.5 kg, more preferably 0.01 to 2 kg, particularly 0.025 to 1.5 kg, depending on the type of desired effect.

[0314] In another preferred embodiment of the invention, the application rate (total amount of the compound of formula (I)) of the compound of formula (I) according to the invention is 0.1 g / ha to 3000 g / ha, preferably 1 g / ha to 1000 g / ha, more preferably 5 g / ha to 1000 g / ha, depending on the control target, season, target plant, and growth stage.

[0315] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) ranges from 0.1 g / ha to 5000 g / ha, preferably from 1 g / ha to 2500 g / ha or from 5 g / ha to 2000 g / ha.

[0316] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) is 0.1 to 1000 g / ha, preferably 1 to 750 g / ha, more preferably 5 to 500 g / ha.

[0317] The required application rate of herbicidal compound B generally ranges from 0.0005 kg / ha to 2.5 kg / ha, preferably from 0.005 kg / ha to 2 kg / ha or from 0.01 kg / ha to 1.5 kg / h in terms of a.s.

[0318] The required application rate of antidote C generally ranges from 0.0005 kg / ha to 2.5 kg / ha, preferably from 0.005 kg / ha to 2 kg / ha or from 0.01 kg / ha to 1.5 kg / h in terms of a.s.

[0319] In the treatment of plant seedlings such as seeds, for example, in the treatment of dusting, coating or perfusion on seeds, generally, the amount of the active substance per 100 kilograms of plant seedlings (preferably seeds) is required to be 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g, and most preferably 5 to 100 g.

[0320] In another embodiment of the present invention, for treating seeds, the amount of the active substances applied, namely A and B and C if appropriate, is generally used in an amount of 0.001 to 10 kg per 100 kg of seeds.

[0321] When used for protecting materials or storage products, the application rate of the active substance depends on the type of the application area and the desired effect. The amount customarily applied for protecting materials is 0.001 g to 2 kg, preferably 0.005 g to 1 kg of the active substance per cubic meter of the treated material.

[0322] In the method of the present invention, it is not important whether the herbicidal compound of formula (I) is formulated and applied together with a further herbicidal component B and / or a herbicide antidote compound C or applied separately.

[0323] When applied separately, the order of application is not critical. It is only necessary to apply the herbicidal compound A and the herbicidal compound B and / or the herbicide antidote component C within a period during which the active ingredients can act on the plants simultaneously, preferably within a period of at most 35 days, in particular within a period of at most 14 days.

[0324] Depending on the applicable method of application, the composition according to the invention can furthermore be used in even more crop plants for removing unwanted plants.

[0325] According to the present invention, all crop plants (cultivated plants) described herein are understood to include all species, subspecies, varieties, cultivars and / or hybrids belonging to the respective cultivated plants, in particular cereals such as wheat and barley, and winter and spring varieties in rapeseed, such as winter wheat, spring wheat, winter barley, etc., but are not limited thereto.

[0326] For example, corn, also known as Indian corn or maize (Zea mays), includes all kinds such as feed corn and sweet corn. According to the present invention, all maize or maize subspecies and / or varieties are included, particularly flour corn (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent corn (Zea mays var. indentata), flint corn (Zea mays var. indurata), sweet corn (Zea mays var. saccharata and Zea mays var. rugosa), waxy corn (Zea mays var. ceratina), amylomaize (high amylose maize varieties), pod corn or wild maize (Zea mays var. tunicata) and striped maize (Zea mays var. japonica).

[0327] Furthermore, most soybean varieties are classified into indeterminate and determinate growth habits, while the wild ancestor of soybeans, Glycine soja, is indeterminate (PNAS 2010, 107(19) 8563 - 856). Indeterminate growth habit (maturity group, MG 00 - MG 4.9) is characterized by continuous plant growth after flowering begins, while determinate soybean varieties (maturity group, (MG) 5 - MG 8) are characterized by most of the plant growth being completed at the time flowering begins. According to the present invention, all soybean cultivars or varieties are included, particularly indeterminate and determinate cultivars or varieties.

[0328] Examples of suitable crops are shown below: Onion (Allium cepa), pineapple (Ananas comosus), peanut (Arachis hypogaea), asparagus (Asparagus officinalis), oat (Avena sativa), sugar beet (Beta vulgaris spec.altissima), turnip (Beta vulgaris spec.rapa), rapeseed (Brassica napus var.napus), rutabaga (Brassica napus var.napobrassica), wild turnip (Brassica rapa var.silvestris), Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec.) Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

[0329] Preferred crops include peanut (Arachis hypogaea), sugar beet (Beta vulgaris spec. altissima), rapeseed (Brassica napus var. napus), kale (Brassica oleracea), lemon (Citrus limon), orange (Citrus sinensis), coffee tree (Coffea arabica), robusta coffee tree (Coffea canephora), liberica coffee tree (Coffea liberica), bermudagrass (Cynodon dactylon), soybean (Glycine max), upland cotton (Gossypium hirsutum), tree cotton (Gossypium arboreum), levant cotton (Gossypium herbaceum), gossypium vitifolium, sunflower (Helianthus annuus), barley (Hordeum vulgare), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple species (Malus spec.), alfalfa (Medicago sativa), tobacco (Nicotiana tabacum) (wild tobacco (N. rustica)), olive (Olea europaea), rice (Oryza sativa), lima bean (Phaseolus lunatus), common bean (Phaseolus vulgaris), pistachio (Pistacia vera), pea (Pisum sativum), almond (Prunus dulcis), sugarcane (Saccharum officinarum), rye (Secale cereale), potato (Solanum tuberosum), sorghum (Sorghum bicolor (millet (S.barley (Hordeum vulgare), rye, bread wheat (Triticum aestivum), durum wheat (Triticum durum), broad bean (Vicia faba), European grape (Vitis vinifera), and maize (Zea mays).

[0330] Particularly preferred crops include cereals, maize, soybean, rice, rapeseed, sugarcane, sunflower, cotton, pea, lentil, chickpea, or permanent crops.

[0331] The compositions according to the invention can also be used in crops that have been modified by mutagenesis or genetic engineering in order to confer new traits to plants or to modify existing traits.

[0332] As used herein, the term "crop" also includes (crop) plants that have been modified by mutagenesis or genetic engineering in order to provide new traits to plants or to modify existing traits.

[0333] Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis for generating mutations at specific loci of the plant genome. In targeted mutagenesis techniques, oligonucleotides, or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs or meganucleases are often used to achieve a targeted effect.

[0334] Genetic engineering typically uses recombinant DNA technology to create modifications to the plant genome that are not easily obtainable by mating, mutagenesis, or natural recombination in the natural environment. Typically, one or more genes are incorporated into the plant genome to add or improve traits. These incorporated genes are also referred to as transgenes in the art, and plants containing such transgenes are called transgenic plants. In the process of plant transformation, several transformation events usually occur where the genomic loci into which the transgenes are incorporated are different. A plant containing a specific transgene at a specific genomic locus is usually described as containing a specific "event", which is referred to by a specific event name. Traits introduced into or modified in plants include, in particular, herbicide tolerance, insect resistance, increased yield, and tolerance to biotic conditions such as drought.

[0335] Herbicide tolerance has been created using mutagenesis as well as genetic recombination. By conventional mutagenesis and breeding methods, plants that have become tolerant to acetolactate synthase (ALS)-inhibiting herbicides include plant varieties marketed under the name Clearfield®. However, most of the herbicide tolerance traits have been created using transgenes.

[0336] Herbicide tolerance is conferred against glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides (such as bromoxynil and ioxynil), sulfonylurea herbicides, ALS inhibitor herbicides, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors (such as isoxaflutole and mesotrione), against microtubule assembly inhibitors such as ikarforin, and against PPO inhibitors such as sarpfenacil, thiafentanil, trifludimoxazin, epirifentanil, CAS 2158274-56-5, CAS 1970221-16-9, CAS 2158274-50-9. The introduced genes used to provide the herbicide tolerance trait include the following: tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, and goxv247; tolerance to glufosinate: pat and bar; tolerance to 2,4-D: aad-1 and aad-12; tolerance to dicamba: dmo; tolerance to oxynil herbicides: bxn; tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA; tolerance to ALS inhibitor herbicides: csr1-2; tolerance to HPPD inhibitors: hppdPF, W336, and avhppd-03; and tolerance to PPO herbicides as described, for example, in WO 2019106568 pamphlet, WO 2023031161 pamphlet, WO 2018022777 pamphlet, WO 2017039969 pamphlet.

[0337] Transgenic corn events containing herbicide-tolerant genes include, for example, but are not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO-φ1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507, and TC6275.

[0338] Transgenic soybean events containing herbicide-tolerant genes include, for example, but are not limited to, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTφH2, W62, W98, FG72, and CV127.

[0339] Transgenic cotton events containing herbicide-tolerant genes include, for example, but are not limited to, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3, and T304-40.

[0340] Transgenic canola events containing herbicide-tolerant genes include, for example, but are not limited to, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3.

[0341] Insect resistance has mainly been created by introducing bacterial genes for insecticidal proteins into plants. The most frequently used transgenes are toxin genes from Bacillus spec. and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, genes from plants have also been introduced into other plants. In particular, genes encoding protease inhibitors such as CpTI and pinII. Furthermore, there is an approach that uses transgenes for producing double-stranded RNA in plants in order to down-regulate targeting insect genes. An example of such a transgene is dvsnf7.

[0342] Transgenic corn events containing genes for insecticidal proteins or double-stranded RNA are, for example, but not excluding others, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418, and MZIR098.

[0343] Transgenic soybean events containing genes for insecticidal proteins are, for example, but not excluding others, MON87701, MON87751, and DAS-81419.

[0344] Transgenic cotton events containing genes for insecticidal proteins include, for example, but are not limited to, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119, and SGK321.

[0345] Yield increases are achieved by increasing ear biomass using the transgene athb17 present in the corn event MON87403 or by improving photosynthesis using the transgene bbx32 present in the soybean event MON87712.

[0346] Crops with improved oil content have been created using the transgenes gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A. Soybean events containing at least one of these genes are: 260-05, MON87705, and MON87769.

[0347] Tolerance to abiotic conditions, particularly waterlogging tolerance, is conferred by using the transgene cspB contained in the corn event MON87460 and by using the transgene Hahb-4 contained in the soybean event IND-φφ41φ-5.

[0348] Combinations of traits are often achieved by combining the genes contained in transformation events or by combining different events during the breeding process. Preferred combinations of traits are herbicide tolerance to various groups of herbicides, insect tolerance to various types of insects, specifically tolerance to Lepidoptera and Coleoptera insects, combinations of herbicide tolerance and one or more types of insect resistance, combinations of herbicide tolerance and increased yield, and combinations of herbicide tolerance and tolerance to abiotic conditions.

[0349] Plants containing single or stacked traits, as well as the genes and events conferring these traits, are known in the art. For example, detailed information regarding mutagenized or incorporated genes and their respective events can be obtained from the websites of the organizations "International Service for the Acquisition of Agri-biotech Applications (ISAAA)" (http: / / www.isaaa.org / gmapprovaldatabase) and "Center for Environmental Risk Assessment (CERA)" (http: / / cera-gmc.org / GMCropDatabase), in addition to patent applications such as European Patent No. 3028573 and International Publication No. 2017 / 011288 pamphlet.

[0350] By using the compositions of the present invention in crops, effects specific to crops containing specific genes or events can be obtained. These effects can include changes in growth behavior, or changes in resistance to biological or abiotic stress factors. Such effects can particularly include an increase in yield, improvement in resistance or tolerance to insect, nematode, fungal, bacterial, mycoplasma, viral or viroid pathogens, and changes in early growth, early or delayed maturity, low or high temperature tolerance, and amino acid or fatty acid spectrum or content.

[0351] Furthermore, particularly for improving the production of raw materials, plants in which the content of components has been adjusted or new components have been incorporated by using recombinant DNA techniques are also included, for example, potatoes with an increased production amount of amylopectin (e.g., Amflora® potato, BASF SE, Germany).

[0352] Furthermore, the composition according to the invention has also been found to be suitable for drying leaves and / or parts of the plant body, and suitable crop plants for this purpose are, for example, cotton, potato, oilseed rape, sunflower, soybean or broad bean, and in particular cotton is preferred. In this context, compositions for drying and / or defoliating the plant body, processes for preparing these compositions and methods for drying and / or defoliating the plant body using the compositions according to the invention have been found.

[0353] The composition according to the invention as a desiccant is particularly suitable for drying the aerial parts of crop plants such as cereals in addition to potato, oilseed rape, sunflower and soybean. By doing so, complete mechanical harvesting of these important crop plants becomes possible.

[0354] Also of economic interest is the acceleration of harvesting, which is made possible by concentrating within a certain time the reduction of the splitting or joining to the tree of citrus fruits, olive fruits and other pear-shaped fruits, stone fruits and nuts, seeds and varieties. The same mechanism, i.e. the promotion of the development of abscission tissue between the fruit or leaf part and the shoot part of the plant, is also essential for the regulation of defoliation of useful plants, in particular cotton.

[0355] Furthermore, by shortening the period until individual cotton plants mature, the quality of the fibres after harvesting is improved.

[0356] The following examples serve to illustrate the invention.

Example

[0357] A Preparation Example Example 1: N4-(5-chloro-2,3,4-trifluoro-6-methoxy-phenyl)-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine. Step 1. 2-chloro-3,4,5-trifluoro-phenol

Chemical formula

[0358] Step 2. 6-Chloro-3,4,5-trifluoro-2-nitro-phenol

Chemical formula

[0359] Step 3. 1-Chloro-4,5,6-trifluoro-2-methoxy-3-nitro-benzene

Chemical formula

[0360] Step 4. 5-Chloro-2,3,4-trifluoro-6-methoxy-aniline

Chemical Structure

[0361] Step 5. N4-(5-Bromo-2,3,4-trifluoro-6-methoxy-phenyl)-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine

Chemical Structure

[0362] Compounds I-1 to I-4 can be synthesized appropriately.

[0363] B Usage Example The herbicidal effects of the compounds and compositions according to the present invention were demonstrated by the following greenhouse experiments.

[0364] The culture containers used were plastic pots containing approximately 3.0% humus-containing loam sand as the substrate. Seeds of the test plants were sown separately for each variety.

[0365] For pre-emergence treatment, the active compound, suspended or emulsified in water, was applied immediately after sowing using a fine distribution nozzle. To promote germination and growth, the containers were gently watered and then covered with a transparent plastic hood until the plants had rooted. Due to this cover, the test plants germinated uniformly unless affected adversely by the active compound.

[0366] For post-emergence treatment, the test plants were grown to a weed height of 3 - 15 cm depending on the weediness and then treated with the active compound suspended or emulsified in water. For this purpose, the test plants were either directly sown and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before treatment.

[0367] Depending on the variety, the plants were kept at 10 - 25°C and 20 - 35°C, respectively.

[0368] The test period ranged from 2 to 4 weeks. During this time, the plants were cared for and the reaction to each treatment was evaluated.

[0369] The evaluation was carried out using a scale from 0 to 100. 100 means no germination of the plants or at least complete destruction of the above-ground part, and 0 means no damage or a normal growth process. Good herbicidal activity is indicated by a value of at least 70, and very good herbicidal activity is indicated by a value of at least 85.

[0370] Unless otherwise stated, each of the components A and B, and, where appropriate, C, was formulated as an emulsion concentrate with a strength of 5% by weight, and an amount of solvent system was added and introduced into the spray liquor used for applying the active compound.

[0371] In the following examples, the method of S.R.Colby (1967) "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, p.22ff. was used to calculate the value E expected if the activity of the individual active compounds were merely additive. E = X + Y - (X.Y / 100) In the formula, X = percentage activity using active compound A at application rate a; Y = percentage activity using active compound B at application rate b; E = expected activity (%) of A + B at application rate a + b.

[0372] If the effect seen in the experiment is higher than the value E calculated according to Colby, a synergistic effect exists.

[0373] The following active compounds were tested: Compound I - 1: [Chemistry] Compound I-2: [Chemistry] Compound I-3: [Chemistry] Compound I-4: [Chemistry]

[0374] Compounds I-1 to I-4 were used as 5% EC formulations.

[0375] Compound B was used as disclosed below in each example. The plants used in the greenhouse experiments were of the following species:

[0376] [Table 59]

[0377] The results of these tests are shown in the following usage examples, demonstrating the synergistic effect of a mixture comprising at least one phenyluracil of formula (I) and at least one herbicide B.

[0378] In this context, a.i. means the active ingredient based on 100% active ingredient.

[0379] As shown, the application was either post-emergence (POST) (BBCH code) or pre-emergence (PRE) at each growth stage (GS) of the weeds.

[0380] Evaluation was carried out 20 days after treatment (DAT).

[0381] Example 1: Synergistic herbicidal action (PRE) of a composition of Compound I-1 and pyroxasulfone Pyrasulfotole was used as a SC formulation with an active ingredient concentration of 500 g / L.

[0382]

Table 60

[0383] Example 2: Synergistic herbicidal effect of the composition of Compound I-2 and pyrasulfotole (POST) Pyrasulfotole was used as a SC formulation with an active ingredient concentration of 500 g / L.

[0384]

Table 61

[0385] Example 3: Synergistic herbicidal effect of the composition of Compound I-1 and sulfufenacil (POST) Sulfufenacil was used as a SC formulation with an active ingredient concentration of 342 g / L.

[0386]

Table 62

[0387] Example 4: Synergistic herbicidal effect of the composition of Compound I-3 and sulfufenacil (PRE) Sulfufenacil was used as a SC formulation with an active ingredient concentration of 342 g / L.

[0388]

Table 63

[0389] Example 5: Synergistic herbicidal effect of the composition of Compound I-1 and simetryn (PRE) Simetryn was used as an EC formulation with an active ingredient concentration of 750 g / L.

[0390]

Table 64

[0391] Example 6: Synergistic Herbicidal Activity (POST) of the Composition of Compound I-3 and Simetryn Simetryn was used as an EC formulation with an active ingredient concentration of 750 g / L.

[0392]

Table 65

[0393] Example 7: Synergistic Herbicidal Activity (PRE) of the Composition of Compound I-1 and Picolinafen Picolinafen was used as a 75% WG formulation.

[0394]

Table 66

[0395] Example 8: Synergistic Herbicidal Activity (PRE) of the Composition of Compound I-2 and Picolinafen Picolinafen was used as a 75% WG formulation.

[0396]

Table 67

[0397] Example 9: Synergistic Herbicidal Activity (POST) of the Composition of Compound I-1 and Atrazine Atrazine was used as an SC formulation with an active ingredient concentration of 480 g / L.

[0398]

Table 68

[0399] Example 10: Synergistic Herbicidal Activity (PRE) of the Composition of Compound I-3 and Atrazine Atrazine was used as a SC formulation with an active ingredient concentration of 480 g / L.

[0400]

Table 69

[0401] Example 11: Synergistic herbicidal effect of the composition of compound I-1 and difluorfenican (POST) Difluorfenican was used as a SC formulation with an active ingredient concentration of 500 g / L.

[0402]

Table 70

[0403] Example 12: Synergistic herbicidal effect of the composition of compound I-2 and difluorfenican (POST) Difluorfenican was used as a SC formulation with an active ingredient concentration of 500 g / L.

[0404]

Table 71

[0405] Example 13: Synergistic herbicidal effect of the composition of compound I-1 and glufosinate-ammonium (POST) Glufosinate-ammonium was used as a SL formulation with an active ingredient concentration of 281.8 g / L.

[0406]

Table 72

[0407] Example 14: Synergistic herbicidal effect of the composition of compound I-3 and glufosinate-ammonium (POST) Glufosinate-ammonium was used as a SL formulation with an active ingredient concentration of 281.8 g / L.

[0408]

Table 73

[0409] Example 15: Synergistic Herbicidal Effect (POST) of the Composition of Compound I-3 and L-Glyphosate-P-Ammonium L-Glyphosate-P-Ammonium was used as a 5% EC formulation.

[0410]

Table 74

[0411] Example 16: Synergistic Herbicidal Effect (PRE) of the Composition of Compound I-1 and Topramezone Topramezone was used as an SC formulation with an active ingredient concentration of 336 g / L.

[0412]

Table 75

[0413] Example 17: Synergistic Herbicidal Effect (POST) of the Composition of Compound I-2 and Topramezone Topramezone was used as an SC formulation with an active ingredient concentration of 336 g / L.

[0414]

Table 76

[0415] Example 18: Synergistic Herbicidal Effect (PRE) of the Composition of Compound I-1 and Sethoxydim Sethoxydim was used as an EC formulation with an active ingredient concentration of 460 g / L.

[0416]

Table 77

[0417] Example 19: Synergistic Herbicidal Effect of the Composition of Compound I-2 and Sethoxydim (PRE) Sethoxydim was used as an EC formulation with an active ingredient concentration of 460 g / L.

[0418] [Table 78]

[0419] Example 20: Synergistic Herbicidal Effect of the Composition of Compound I-1 and Dicamba (POST) Dicamba was used as an SL formulation with an active ingredient concentration of 480 g / L.

[0420] [Table 79]

[0421] Example 21: Synergistic Herbicidal Effect of the Composition of Compound I-3 and Dicamba (POST) Dicamba was used as an SL formulation with an active ingredient concentration of 480 g / L.

[0422] [Table 80]

[0423] Example 22: Synergistic Herbicidal Effect of the Composition of Compound I-2 and Imazethapyr (PRE) Imazethapyr was used as an SL formulation with an active ingredient concentration of 240 g / L.

[0424] [Table 81]

[0425] Example 23: Synergistic Herbicidal Effect of the Composition of Compound I-3 and Imazethapyr (PRE) Imazetapyr was used as an SL formulation with an active ingredient concentration of 240 g / L.

[0426]

Table 82

[0427] Example 24: Synergistic herbicidal effect of the composition of Compound I-1 and trifludimoxazin (POST) Trifludimoxazin was used as an SC formulation with an active ingredient concentration of 500 g / L.

[0428]

Table 83

[0429] Example 25: Synergistic herbicidal effect of the composition of Compound I-3 and trifludimoxazin (PRE)

[0430]

Table 84

[0431] Example 26: Synergistic herbicidal effect of the composition of Compound I-1 and glyphosate (POST) Glyphosate was used as an SL formulation with an active ingredient concentration of 575 g / L.

[0432]

Table 85

[0433] Example 27: Synergistic herbicidal effect of the composition of Compound I-2 and glyphosate (POST) Glyphosate was used as an SL formulation with an active ingredient concentration of 575 g / L.

[0434]

Table 86

[0435] Example 28: Synergistic Herbicidal Effect of the Composition of Compound I-3 and Glyphosate (POST) Glyphosate was used as an SL formulation having an active ingredient concentration of 575 g / L.

[0436] [Table 87]

[0437] Example 29: Synergistic Herbicidal Effect of the Composition of Compound I-1 and Pendimethalin (PRE) Pendimethalin was used as an SC formulation having an active ingredient concentration of 400 g / L.

[0438] [Table 88]

[0439] Example 30: Synergistic Herbicidal Effect of the Composition of Compound I-3 and Pendimethalin (PRE) Pendimethalin was used as an SC formulation having an active ingredient concentration of 400 g / L.

[0440] [Table 89]

[0441] Example 31: Synergistic Herbicidal Effect of the Composition of Compound I-1 and Pretilachlor (PRE) Pretilachlor was used as an SC formulation having an active ingredient concentration of 500 g / L.

[0442] [Table 90]

[0443] Example 32: Synergistic Herbicidal Effect of the Composition of Compound I-2 and Pretilachlor (PRE) Pretilachlor was used as a SC formulation with an active ingredient concentration of 500 g / L.

[0444]

Table 91

[0445] Example 33: Synergistic herbicidal effect of the composition of Compound I-1 and bicyclopyrone (PRE) Bicyclopyrone was used as a SC formulation with an active ingredient concentration of 400 g / L.

[0446]

Table 92

[0447] Example 34: Synergistic herbicidal effect of the composition of Compound I-3 and bicyclopyrone (PRE) Bicyclopyrone was used as a SC formulation with an active ingredient concentration of 400 g / L.

[0448]

Table 93

[0449] Example 35: Synergistic herbicidal effect of the composition of Compound I-1 and acronifen (PRE) Acronifen was used as a SC formulation with an active ingredient concentration of 600 g / L.

[0450]

Table 94

[0451] Example 36: Synergistic herbicidal effect of the composition of Compound I-3 and acronifen (PRE) Acronifen was used as a SC formulation with an active ingredient concentration of 600 g / L.

[0452]

Table 95

[0453] Example 37: Synergistic Herbicidal Effect (PRE) of the Composition of Compound I-1 and Butachlor Butachlor was used as an EW formulation with an active ingredient concentration of 50%.

[0454] [Table 96]

[0455] Example 38: Synergistic Herbicidal Effect (PRE) of the Composition of Compound I-2 and Butachlor Butachlor was used as an EW formulation with an active ingredient concentration of 50%.

[0456] [Table 97]

[0457] Example 39: Synergistic Herbicidal Effect (PRE) of the Composition of Compound I-1 and Isoxaben Isoxaben was used as an SC formulation with an active ingredient concentration of 500 g / L.

[0458] [Table 98]

[0459] Example 40: Synergistic Herbicidal Effect (PRE) of the Composition of Compound I-3 and Isoxaben Isoxaben was used as an SC formulation with an active ingredient concentration of 500 g / L.

[0460] [Table 99]

[0461] Example 41: Synergistic Herbicidal Action of the Composition of Compound I-1 and Mesotrione (PRE) Mesotrione was used as an SC formulation with an active ingredient concentration of 100 g / L.

[0462]

Table 100

[0463] Example 42: Synergistic Herbicidal Action of the Composition of Compound I-3 and Mesotrione (PRE) Mesotrione was used as an SC formulation with an active ingredient concentration of 100 g / L.

[0464]

Table 101

[0465] Example 43: Synergistic Herbicidal Action of the Composition of Compound I-1 and Isoxaflutole (PRE) Isoxaflutole was used as a WG formulation with an active ingredient concentration of 75%.

[0466]

Table 102

[0467] Example 44: Synergistic Herbicidal Action of the Composition of Compound I-2 and Isoxaflutole (PRE) Isoxaflutole was used as a WG formulation with an active ingredient concentration of 75%.

[0468]

Table 103

[0469] Example 45: Synergistic Herbicidal Action of the Composition of Compound I-1 and Profoxydim (POST) Profoxydim was used as an EC formulation with an active ingredient concentration of 200 g / L.

[0470]

Table 104

[0471] Example 46: Synergistic Herbicidal Activity (POST) of the Composition of Compound I-3 and Profoxydim Profoxydim was used as an EC formulation with an active ingredient concentration of 200 g / L.

[0472]

Table 105

[0473] Example 47: Synergistic Herbicidal Activity (POST) of the Composition of Compound I-1 and Dimethenamid-P Dimethenamid-P was used as an EC formulation with an active ingredient concentration of 720 g / L.

[0474]

Table 106

[0475] Example 48: Synergistic Herbicidal Activity (POST) of the Composition of Compound I-4 and Cyclopyrimorate Cyclopyrimorate was used as an SC formulation with an active ingredient concentration of 20%.

[0476]

Table 107

[0477] Example 49: Synergistic Herbicidal Activity (POST) of the Composition of Compound I-3 and Tetflupyrolimet Tetflupyrolimet was used as a 5% EC formulation.

[0478]

Table 108

[0479] Example 50: Synergistic Herbicidal Action of the Composition of Compound I-3 and Diflufenican (PRE) Diflufenican was used as an SP formulation with an active ingredient concentration of 86%.

[0480] [Table 109]

[0481] Example 51: Synergistic Herbicidal Action of the Composition of Compound I-4 and Epilifenzynal (POST) Epilifenzynal was used as an EC formulation with an active ingredient concentration of 5%.

[0482] [Table 110]

[0483] Example 52: Synergistic Herbicidal Action of the Composition of Compound I-3 and 2,4-D (POST) 2,4-D was used as an EC formulation with an active ingredient concentration of 600 g / L.

[0484] [Table 111]

[0485] Example 53: Synergistic Herbicidal Action of the Composition of Compound I-3 and Metribuzin (POST) Metribuzin was used as a WG formulation with an active ingredient concentration of 70%.

[0486] [Table 112]

[0487] Example 54: Synergistic Herbicidal Action of the Composition of Compound I-4 and Metribuzin (PRE) Metribuzin was used as a WG formulation with an active ingredient concentration of 70%.

[0488]

Table 113

[0489] Example 55: Synergistic herbicidal effect of the composition of Compound I-3 and Sihalofop-butyl (POST) Sihalofop-butyl was used as an EC formulation with an active ingredient concentration of 200 g / L.

[0490]

Table 114

[0491] Example 56: Synergistic herbicidal effect of the composition of Compound I-4 and Penoxsulam (POST) Penoxsulam was used as an OD formulation with an active ingredient concentration of 20.4 g / L.

[0492]

Table 115

[0493] Example 57: Synergistic herbicidal effect of the composition of Compound I-4 and Florpyrauxifen-benzyl (PRE) Florpyrauxifen-benzyl was used as an EC formulation with an active ingredient concentration of 25 g / L.

[0494]

Table 116

[0495] Example 58: Synergistic herbicidal effect of the composition of Compound I-3 and Metamifop (POST) Metamifop was used as a 5% EC formulation.

[0496]

Table 117

[0497] Example 59: Synergistic Herbicidal Activity (PRE and POST) of the Composition of Compound I-3 and Flufenacet Flufenacet was used as an SC formulation with an active ingredient concentration of 508.8 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0498]

Table 118

[0499] POST

[0500]

Table 119

[0501] Example 60: Synergistic Herbicidal Activity (PRE and POST) of the Composition of Compound I-2 and Flufenacet Flufenacet was used as an SC formulation with an active ingredient concentration of 508.8 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0502]

Table 120

[0503] POST

[0504]

Table 121

[0505] Example 61: Synergistic Herbicidal Activity (PRE and POST) of a Composition of Compound I-3 and Ethyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetate Ethyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetate was used as a 5% EC formulation. Evaluation was carried out 20 days after treatment (DAT). PRE

[0506] [Table 122]

[0507] POST

[0508] [Table 123]

[0509] Example 62: Synergistic Herbicidal Activity (PRE and POST) of a Composition of Compound I-2 and Ethyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetate Ethyl 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetate was used as a 5% EC formulation. Evaluation was carried out 20 days after treatment (DAT). PRE

[0510] [Table 124]

[0511] POST

[0512]

Table 125

[0513] Example 63: Synergistic herbicidal effect of the composition of compound I-3 and triarate (PRE and POST) Triarate was used as a CS formulation with an active ingredient concentration of 450 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0514]

Table 126

[0515] POST

[0516]

Table 127

[0517] Example 64: Synergistic herbicidal effect of the composition of compound I-2 and triarate (PRE and POST) Triarate was used as a CS formulation with an active ingredient concentration of 450 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0518]

Table 128

[0519] POST

[0520]

Table 129

[0521] Example 65: Synergistic Herbicidal Effects of the Composition of Compound I-3 and Imazamox (PRE and POST) Imazamox was used as an SL formulation with an active ingredient concentration of 120 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0522] [Table 130]

[0523] POST

[0524] [Table 131]

[0525] Example 65: Synergistic Herbicidal Effects of the Composition of Compound I-2 and Imazamox (PRE and POST) Imazamox was used as an SL formulation with an active ingredient concentration of 120 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0526] [Table 132]

[0527] POST

[0528] [Table 133]

[0529] Example 66: Synergistic Herbicidal Effects of the Composition of Compound I-3 and Quizalofop-ethyl (PRE and POST) Quizalofop-ethyl was used as a 5% EC formulation. Evaluation was carried out 20 days after treatment (DAT). PRE

[0530]

Table 134

[0531] POST

[0532]

Table 135

[0533] Example 67: Synergistic herbicidal effect of the composition of compound I-2 and quizalofop-ethyl (PRE and POST) Quizalofop-ethyl was used as a 5% EC formulation. Evaluation was carried out 20 days after treatment (DAT). PRE

[0534]

Table 136

[0535] POST

[0536]

Table 137

[0537] Example 68: Synergistic herbicidal effect of the composition of compound I-3 and terbuthylazine (PRE and POST) Terbuthylazine was used as an SC formulation with an active ingredient concentration of 500 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0538]

Table 138

[0539] POST

[0540]

Table 139

[0541] Example 69: Synergistic Herbicidal Activity of the Composition of Compound I-2 and Terbuthylazine (PRE and POST) Terbuthylazine was used as an SC formulation with an active ingredient concentration of 500 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0542] [Table 140]

[0543] POST

[0544] [Table 141]

[0545] Example 70: Synergistic Herbicidal Activity of the Composition of Compound I-3, Thienecarbazone-methyl, and the Safener (Mefenpyr-diethyl) (PRE and POST) Thienecarbazone-methyl and the safener mefenpyr-diethyl were used as an EC formulation with an active ingredient concentration of 10 g / L (herbicide) and 60 g / L (safener). Evaluation was carried out 20 days after treatment (DAT). PRE

[0546] [Table 142]

[0547] POST

[0548] [Table 143]

[0549] Example 71: Synergistic Herbicidal Activity of the Composition of Compound I-2, Thienecarbazone-methyl, and the Safener (Mefenpyr-diethyl) (PRE and POST) Thienecarbazon-methyl and the antidote mefenpyr-diethyl were used as an EC formulation having an active ingredient concentration of 10 g / L (herbicide) and 60 g / L (antidote). Evaluation was carried out 20 days after treatment (DAT). PRE

[0550]

Table 144

[0551] POST

[0552]

Table 145

[0553] Example 72: Synergistic herbicidal effect of the composition of compound I-3 and cyclohexydim (PRE and POST) Cyclohexydim was used as an EC formulation having an active ingredient concentration of 100 g / L and evaluation was carried out 20 days after treatment (DAT). PRE

[0554]

Table 146

[0555] POST

[0556]

Table 147

[0557] Example 73: Synergistic herbicidal effect of the composition of compound I-4 and cyclohexydim (PRE and POST) Cyclohexydim was used as an EC formulation having an active ingredient concentration of 100 g / L and evaluation was carried out 20 days after treatment (DAT). PRE

[0558]

Table 148

[0559] POST

[0560]

Table 149

[0561] Example 74: Synergistic Herbicidal Activity of the Composition of Compound I-3 and Clethodim (PRE and POST) Clethodim was used as an EC formulation with an active ingredient concentration of 240 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0562]

Table 150

[0563] POST

[0564]

Table 151

[0565] Example 75: Synergistic Herbicidal Activity of the Composition of Compound I-4 and Clethodim (PRE and POST) Clethodim was used as an EC formulation with an active ingredient concentration of 240 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0566]

Table 152

[0567] POST

[0568]

Table 153

[0569] Example 76: Synergistic Herbicidal Activity of the Composition of Compound I-3 and Bentazone (PRE and POST) Bentazone was used as an SL formulation with an active ingredient concentration of 480 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0570] [Table 154]

[0571] POST

[0572] [Table 155]

[0573] Example 77: Synergistic Herbicidal Activity of the Composition of Compound I-4 and Bentazone (PRE and POST) Bentazone was used as an SL formulation with an active ingredient concentration of 480 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0574] [Table 156]

[0575] POST

[0576] [Table 157]

[0577] Example 78: Synergistic Herbicidal Activity of the Composition of Compound I-3 and Flumioxazin (PRE and POST) Flumioxazin was used as a WG formulation with an active ingredient concentration of 500 g / kg. Evaluation was carried out 20 days after treatment (DAT). PRE

[0578]

Table 158

[0579] POST

[0580]

Table 159

[0581] Example 79: Synergistic herbicidal effect of the composition of compound I-4 and flumioxazin (PRE and POST) Flumioxazin was used as a WG formulation with an active ingredient concentration of 500 g / kg. Evaluation was carried out 20 days after treatment (DAT). PRE

[0582]

Table 160

[0583] POST

[0584]

Table 161

[0585] Example 80: Synergistic herbicidal effect of the composition of compound I-3 and mesosafen (PRE and POST) Mesosafen was used as an SL formulation with an active ingredient concentration of 250 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0586]

Table 162

[0587] POST

[0588]

Table 163

[0589] Example 81: Synergistic Herbicidal Activity (PRE and POST) of the Composition of Compound I-2 and Homethiofen Homethiofen was used as an SL formulation with an active ingredient concentration of 250 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0590] [Table 164]

[0591] POST

[0592] [Table 165]

[0593] Example 82: Synergistic Herbicidal Activity (PRE and POST) of the Composition of Compound I-3 and S-Metolachlor S-Metolachlor was used as an EC formulation with an active ingredient concentration of 960 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0594] [Table 166]

[0595] POST

[0596] [Table 167]

[0597] Example 83: Synergistic Herbicidal Activity (PRE and POST) of the Composition of Compound I-2 and S-Metolachlor S-Metolachlor was used as an EC formulation with an active ingredient concentration of 960 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0598]

Table 168

[0599] POST

[0600]

Table 169

[0601] Example 84: Synergistic herbicidal effect of the composition of Compound I-3 and sulfufenacil (PRE and POST) Sulfufenacil was used as a CS formulation with an active ingredient concentration of 130 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0602]

Table 170

[0603] POST

[0604]

Table 171

[0605] Example 85: Synergistic herbicidal effect of the composition of Compound I-2 and sulfufenacil (PRE and POST) Sulfufenacil was used as a CS formulation with an active ingredient concentration of 130 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0606]

Table 172

[0607] POST

[0608]

Table 173

[0609] Example 86: Synergistic Herbicidal Activity (PRE and POST) of the Composition of Compound I-3 and Rimisoxafen Rimisoxafen was used as a 5% EC formulation. Evaluation was carried out 20 days after treatment (DAT). PRE

[0610]

Table 174

[0611] POST

[0612]

Table 175

[0613] Example 87: Synergistic Herbicidal Activity (PRE and POST) of the Composition of Compound I-2 and Rimisoxafen Rimisoxafen was used as a 5% EC formulation. Evaluation was carried out 20 days after treatment (DAT). PRE

[0614]

Table 176

[0615] POST

[0616]

Table 177

[0617] Example 88: Synergistic Herbicidal Activity (PRE and POST) of the Composition of Compound I-3 and Propanyl Propanyl was used as an EC formulation with an active ingredient concentration of 480 g / L. It was evaluated 18 days after treatment (DAT). PRE

[0618]

Table 178

[0619] POST

[0620]

Table 179

[0621] Example 89: Synergistic herbicidal effect of the composition of Compound I-2 and propanyl (PRE and POST) Propanyl was used as an EC formulation with an active ingredient concentration of 480 g / L. It was evaluated 18 days after treatment (DAT). PRE

[0622]

Table 180

[0623] POST

[0624]

Table 181

[0625] Example 90: Synergistic herbicidal effect of the composition of Compound I-3 and bromoxynil (PRE and POST) Bromoxynil was used as an EC formulation with an active ingredient concentration of 225 g / L. It was evaluated 18 days after treatment (DAT). PRE

[0626]

Table 182

[0627] POST

[0628]

Table 183

[0629] Example 91: Synergistic herbicidal effect of the composition of compound I-2 and bromoxynil (PRE and POST) Bromoxynil was used as an EC formulation with an active ingredient concentration of 225 g / L. Evaluation was carried out 18 days after treatment (DAT). PRE

[0630]

Table 184

[0631] POST

[0632]

Table 185

[0633] Example 92: Synergistic herbicidal effect of the composition of compound I-3 and propyzamide (PRE and POST) Propyzamide was used as an SC formulation with an active ingredient concentration of 400 g / L. Evaluation was carried out 18 days after treatment (DAT). PRE

[0634]

Table 186

[0635] POST

[0636]

Table 187

[0637] Example 93: Synergistic Herbicidal Effect of the Composition of Compound I-2 and Propyzamide (PRE and POST) Propyzamide was used as an SC formulation with an active ingredient concentration of 400 g / L. Evaluation was carried out 18 days after treatment (DAT). PRE

[0638] [Table 188]

[0639] POST

[0640] [Table 189]

[0641] Example 94: Synergistic Herbicidal Effect of the Composition of Compound I-3 and Indaziflam (PRE and POST) Indaziflam was used as an SC formulation with an active ingredient concentration of 200 g / L. Evaluation was carried out 18 days after treatment (DAT). PRE

[0642] [Table 190]

[0643] POST

[0644] [Table 191]

[0645] Example 94: Synergistic Herbicidal Effect of the Composition of Compound I-2 and Indaziflam (PRE and POST) Indaziflam was used as an SC formulation with an active ingredient concentration of 200 g / L. Evaluation was carried out 18 days after treatment (DAT). PRE

[0646] [Table 192]

[0647] POST

[0648]

Table 193

[0649] Example 96: Synergistic herbicidal effect of the composition of compound I-3 and prosulfocarb (PRE and POST) Prosulfocarb was used as an EC formulation with an active ingredient concentration of 800 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0650]

Table 194

[0651] POST

[0652]

Table 195

[0653] Example 97: Synergistic herbicidal effect of the composition of compound I-4 and prosulfocarb (PRE) Prosulfocarb was used as an EC formulation with an active ingredient concentration of 800 g / L. Evaluation was carried out 20 days after treatment (DAT). PRE

[0654]

Table 196

[0655] Example 98: Synergistic herbicidal effect of the composition of compound I-3 and trifluralin (PRE and POST) Trifluralin was used as a 5% EC formulation. Evaluation was carried out 20 days after treatment (DAT). PRE

[0656]

Table 197

[0657] POST

[0658]

Table 198

[0659] Example 99: Synergistic Herbicidal Activity of the Composition of Compound I-4 and Trifluralin (PRE and POST) Trifluralin was used as a 5% EC formulation. Evaluation was carried out 20 days after treatment (DAT). PRE

[0660]

Table 199

[0661] POST

[0662]

Table 200

[0663] Example 100: Synergistic Herbicidal Activity of the Composition of Compound I-3 and Pyroxasulfone (PRE) Pyroxasulfone was used as a WG formulation with an active ingredient concentration of 215 g / kg. Evaluation was carried out 20 days after treatment (DAT). PRE

[0664]

Table 201

[0665] Example 101: Synergistic Herbicidal Activity of the Composition of Compound I-4 and Pyroxasulfone (PRE) Pyroxasulfone was used as a WG formulation with an active ingredient concentration of 215 g / kg. It was evaluated 20 days after treatment (DAT). PRE

[0666]

Table 202

[0667] Example 100: Synergistic herbicidal effect of the composition of Compound I-3 and bispyribac-sodium (PRE) Bispyribac-sodium was used as an SC formulation with an active ingredient concentration of 100 g / L. It was evaluated 20 days after treatment (DAT). PRE

[0668]

Table 203

[0669] Example 102: Synergistic herbicidal effect of the composition of Compound I-3 and bispyribac-sodium (PRE) Bispyribac-sodium was used as an SC formulation with an active ingredient concentration of 100 g / L. It was evaluated 20 days after treatment (DAT). PRE

[0670]

Table 204

[0671] Example 103: Synergistic herbicidal effect of the composition of Compound I-3 and mesosulfuron-methyl (PRE) Mesosulfuron-methyl was used as a WG formulation with an active ingredient concentration of 45 g / kg. It was evaluated 20 days after treatment (DAT). PRE

[0672]

Table 205

[0673] Example 104: Synergistic Herbicidal Activity of the Composition of Compound I-2 and Mesosulfuron-methyl (PRE) Mesosulfuron-methyl was used as a WG formulation with an active ingredient concentration of 45 g / kg. Evaluation was carried out 20 days after treatment (DAT). PRE

[0674] [Table 206]

[0675] Example 105: Synergistic Herbicidal Activity of the Composition of Compound I-3 and Pyraclonil (PRE) Pyraclonil was used as a 5% EC formulation. Evaluation was carried out 20 days after treatment (DAT). PRE

[0676] [Table 207]

[0677] Example 106: Synergistic Herbicidal Activity of the Composition of Compound I-2 and Pyraclonil (PRE and POST) Pyraclonil was used as a 5% EC formulation. Evaluation was carried out 20 days after treatment (DAT). PRE

[0678] [Table 208]

[0679] POST

[0680] [Table 209]

[0681] Example 107: Synergistic Herbicidal Activity of the Composition of Compound I-2 and Ethofumesate (PRE) Ethofenamate was used as an SC formulation with an active ingredient concentration of 500 g / L. It was evaluated 20 days after treatment (DAT). PRE

[0682]

Table 210

[0683] Example 108: Synergistic herbicidal effect of the composition of Compound I-3 and cinchonazine (PRE) Cinchonazine was used as an SC formulation with an active ingredient concentration of 250 g / L. It was evaluated 20 days after treatment (DAT). PRE

[0684]

Table 211

[0685] Example 109: Synergistic herbicidal effect of the composition of Compound I-2 and cinchonazine (PRE) Cinchonazine was used as an SC formulation with an active ingredient concentration of 250 g / L. It was evaluated 20 days after treatment (DAT). PRE

[0686]

Table 212

[0687] POST

[0688]

Table 213

[0689] Example 110: Synergistic herbicidal effect of the composition of Compound I-3 and ioxynil (PRE) Ioxynil was used as a 5% EC formulation. It was evaluated 10 days after treatment (DAT). PRE

[0690]

Table 214

[0691] Example 111: Synergistic Herbicidal Effect (PRE) of the Composition of Compound I-2 and Icafollin Icafollin was used as a 5% EC formulation. Evaluation was carried out 10 days after treatment (DAT). PRE

[0692]

Table 215

[0693] Example 112: Synergistic Herbicidal Effect (PRE) of the Composition of Compound I-4 and Icafollin Icafollin was used as a 5% EC formulation. Evaluation was carried out 10 days after treatment (DAT). PRE

[0694]

Table 216

Claims

1. Equation (I) 【Chemistry 1】 [In the formula, R １ is F; R ２ H, halogen, CR ２Ａ Selected from the group consisting of; Here R ２Ａ is H or a halogen; R ３ H and F are; R ４ F, Cl, Br, I, CR ４Ａ Selected from the group consisting of; Here R ４Ａ is H or a halogen; R ５ is selected from the group consisting of H, halogen, CN, C １ ~C ６ -alkyl, (C １ ~C ６ -alkoxy)-C １ ~C ６ -alkyl, C ３ ~C ６ -cycloalkyl, (C ３ ~C ６ -cycloalkyl)-C １ ~C ４ -alkyl, C １ ~C ６ ２ ~C ６ -alkenyloxy, C ２ ~C ６ -alkynyloxy, C ３ ~C ６ -cycloalkoxy, (C ３ ~C ６ -cycloalkyl)-C １ ~C ４ -alkoxy, and the aliphatic and alicyclic moieties of said groups are unsubstituted or partially or fully halogenated;​ R ６ H, halogen, CN, C １ ~C ６ - Alkyl, C １ ~C ６ - Haloalkyl, C １ ~C ６ - Alkoxy and C １ ~C ６ - Selected from the group consisting of haloalkoxys; R ７ is halogen, CN, C １ ~C ６ - Alkyl, C ２ ~C ６ - Alkenil, C ３ ~C ６ - Alkinyl, C ３ ~C ６ -Cycloalkyl, (C ３ ~C ６ -Cycloalkyl)-C １ ~C ４ - Alkyl, C ３ ~C ６ -Cycloalkenyl and C １ ~C ６ -Alkoxy-C １ ~C ６ - Selected from the group consisting of alkyl groups, wherein the aliphatic and alicyclic moieties of the group are unsubstituted, partially, or completely halogenated; R ６ and R ７ together with the carbon atom to which they are attached form a carbonyl, C ３ to C ６ -cycloalkyl, C ３ to C ６ -cycloalkenyl, a 3- to 6-membered saturated or partially unsaturated heterocyclyl and a partial >C=CR ｘ R ｙ (where R ｘ and R ｙ are hydrogen, C １ to C ４ -alkyl, C １ to C ４ -haloalkyl, C ３ to C ６ -cycloalkyl, or CR ｘ R ｙ forms a 3- to 6-membered cycloalkyl) selected from the group consisting of; R ８ is C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, (C １ to C ６ -alkoxy)-C １ to C ６ -alkyl, (C １ to C ６ -alkoxy)-C ２ to C ６ -alkenyl, (C １ to C ６ -alkoxy)-C ２ to C ６ -alkynyl, (C １ to C ６ -cycloalkyl)-C ２ to C ６ -alkynyl, (C ３ to C ６ -cycloalkyl)-C １ to C ４ -alkyl, (C ３ to C ６ -cycloalkoxy)-C １ to C ４ - Selected from the group consisting of alkyl groups, the aforementioned groups are unsubstituted, partially or completely halogenated, and the alicyclic moieties of the last six mentioned groups may have 1, 2, 3, 4, 5, or 6 methyl groups] and at least one compound A), A combination of herbicides comprising herbicide compound b) and antidote c) and at least one further compound selected from mixtures thereof, The further herbicidal active compound b) is one of the following classes b1) to b15): b1) Lipid biosynthesis inhibitors; b2) Acetolactate synthase inhibitors; b3) Photosynthesis inhibitors; b4) Protoporphyrinogen-IX oxidase inhibitors, b5) Whitening herbicides; b6) Enolpyruvir ciquimate 3-phosphate synthase inhibitor; b7) Glutamine synthetase inhibitors; b8) 7,8-dihydropteroate synthase inhibitors; b9) Mitotic inhibitors; b10) Inhibitors of the synthesis of very long-chain fatty acids; b11) Cellulose biosynthesis inhibitors; b12) Decoupler herbicides; b13) Auxin herbicides; b14) Auxin transport inhibitors; and b15) Bromobutide, Chlorfrenol, Chlorfrenol-methyl, Symmethilin, Cumilon, Darapon, Dazomet, Diphenzocort, Diphenzocort-methyl sulfate, Dimethipine, DSMA, Daimuron, Endotar and its salts, Etobenzanide, Flamprop, Flamprop-isopropyl, Flamprop-methyl, Flamprop-M-isopropyl, Flamprop-M-methyl, Flurenol, Flurenol-butyl, Fluprimidol, Fosamine, Fosamine-ammonium, In Other herbicides selected from the group comprising danofan, indadiflame, hydrazide maleate, mefluzide, metam, methiozoline, methylazide, methylbromide, methyl-dimylon, methyliodide, MSMA, oleic acid, oxadiclomefone, pelargonic acid, pyributicarb, quinoclamin, tetoflupyrrolimet, triaziflame, tridiphan, 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol and agronomically acceptable salts or derivatives thereof, including salts and esters thereof; Selected from the compounds; A combination in which compound C) is selected from the group consisting of benoxacol, croquintoset, siomethrinyl, cyprosulfamide, dichlormid, dicyclonone, diethrate, fenchlorazole, fenchlorim, flurazole, fluxofenim, flirazole, isoxadifen, mefenpyr, mefenate, anhydrous naphthalic acid, oxavethrinyl, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane, 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine, and N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide.

2. The further herbicidal active compound b) is one of the following classes b1) to b15): b1) Selected from the group of lipid biosynthesis inhibitors: ACC-herbicides, e.g., alloxidim, alloxidim-sodium, butroxidim, crethodym, clodinahop, clodinahop-propargyl, cycloxidim, cyhalofop, cyhalofop-butyl, diclohop, diclohop-methyl, phenoxaprop, phenoxaprop-ethyl, phenoxaprop-P, phenoxaprop-P-ethyl, fluadifop, fluadifop-butyl, flua Dihop-P, fluadifop-P-butyl, haloxyhop, haloxyhop-methyl, haloxyhop-P, haloxyhop-P-methyl, metamihop, pinoxadene, propoxydime, propaxifop, quizalohop, quizalohop-ethyl, quizalohop-tefuryl, quizalohop-P, quizalohop-P-ethyl, quizalohop-P-tefuryl, cethoxydime, tepraloxidime, tralcoxidime, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'- [Biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2 ,2,6,6-tetramethyl-2H-pyran-3-one (CAS1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS13 12340-82-1); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl methyl carbonate (CAS1312337-51-1);4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl methyl carbonate; 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl methyl carbonate (CAS1312340-83-2); 4-(2',4'-dichloro-4-ethyl[1, 1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl methyl carbonate (CAS1033760-58-5); and non-ACC herbicides, such as benfresate, butyrate, cycloate, darapon, dimepiperate, EPTC, esprocarb, etofmesate, flupropanate, molinate, olbencarb, pevlate, prosulfocarb, TCA, thiobencarb, thiocarbasil, triallate and vernolate; b2) Select from the group of ALS inhibitors: Sulfonylureas, for example, amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cykosulfuron, cyclosulfamuron, etametsulfuron, etametsulfuron-methyl, ethoxysulfuron, fluzasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, horamsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iophensulfuron, iophensulfuron-na Thorium, mesosulfuron, metazosulfuron, metusulfuron, metusulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propirisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, limsulfuron, sulfometsuron, sulfometsuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenulon, tribenulon-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl, and tritosulfuron Imidazolinones, such as imazametabenz, imazametabenz-methyl, imazamox, imazapic, imazapyr, imazakine, and imazetapyr, triazolopyrimidine herbicides, and sulfonanilides, such as chloransrum, chloransrum-methyl, diclosrum, flumetulam, florasrum, methosrum, penoxulam, pyrimisulfan, and pyroxulam. Pyrimidinyl benzoate derivatives, for example, bispyribac, bispyribac sodium, pyribenzoxime, pyriflubenzoxin, pyriftalide, pyriminobac, pyriminobac methyl, pyrithiobac, pyrithiobac sodium, 4-[[[2-[(4,-6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoate-1-methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoate propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethaneamine (CAS 420138-01-8), Sulfonylaminocarbonyltriazolinone herbicides, such as flucarbazone, flucarbazone sodium, propoxycarbazone, propoxycarbazone sodium, thiencarbazone and thiencarbazone methyl; and triafamone; Among these, a preferred embodiment of the present invention relates to a composition comprising at least one imidazolinone herbicide; b3) Selected from the group of photosynthesis inhibitors: Amicarbazones, inhibitors of photosystem II, for example, 1-(6-tert-butylpyrimidine-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrole-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazole-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrole-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazole-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrole-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methylpyrazole-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrole-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methylpyrazole-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrole-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidine-2-one; (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidine-2-one (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidine-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidined-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazole-3-yl]imidazolidine-2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazole-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidine-2-one (CAS 1844836-64-1), triazine herbicides including chlorotriazine, triazinon, triazinedione, methylthiotriazine and pyridazinon, e.g., ametrin, atrazine, chloridazone, cyanazine, desmethrin, dimethametrin, hexazinone, metrivudine, prometon, promethrin, propazine, simazine, simetrin, terbumeton, terbutyrazine, terbutrin and trietadine, arylureas, e.g., chlorobromurone, chlorotolurone, chloroxurone, dimeflon, diurone, fluomethurone, isoproturone, isouron, linurone, metamitron, metabenzuthiazuron, metobenzuron, metoxurone, monolinurone, nevron, sidurone, tebuthiurone and thiadiazuron, phenylcarbamates, e.g., desmedifam, carburate, fenmedifam, fen Medifam-ethyl, nitrile herbicides, such as bromophenoxime, bromoxynil and their salts and esters, ioxynil and its salts and esters, uracil, such as bromacil, renacil and terbacil, and bentazone and bentazone-sodium, pyridate, pyridafor, pentanocrol and propanil, and photosystem I inhibitors, such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimethyl sulfate (of these, preferred embodiments of the present invention relate to compositions comprising at least one arylurea herbicide. Of these, equally preferred embodiments of the present invention relate to compositions comprising at least one triazine herbicide. Of these, equally preferred embodiments of the present invention relate to compositions comprising at least one nitrile herbicide); b4) Select from the group of protoporphyrinogen-IX oxidase inhibitors: Acifluorphen, Acifluorphen-sodium, Azaphenidine, Bencarbazone, Benzufenzizone, Bifenox, Butaphenacil, Carfentrazone, Carfentrazone-ethyl, Clomethoxyfen, Chlorphthalim, Synidone-ethyl, Cyclopyranil, Fluazolate, Fluphenoximacil, Flufenpyr, Flufenpyr-ethyl, Flumicrolac, Flumicrolac-pentyl, Flumioxazine, Fluroglycopene, Fluroglycopene-ethyl, Fluthia Set, Fluthiaset-methyl, Homesaphen, Halosaphen, Lactofen, Oxaziargyl, Oxadiazone, Oxyfluorphen, Pentoxazone, Profluazole, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Saflufenacil, Sulfentrazone, Thidiadimine, Thiafenacil, Trifludimoxazine, Epirifenacil, N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS) 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(propa-2-inyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-propa-2-inyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-Trifluoro-3-oxo-4-propa-2-inyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl(E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazole-3-yl]-4-fluorophenoxy]-3-methoxy-buta-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazole-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4), 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-methyl acetate (CAS 1970221-16-9), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]methyl acetate (CAS 2158274-96-3), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]ethyl acetate (CAS 2158274-50-9), 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazole-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]methyl acetate (CAS 2271389-22-9), 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazole-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]ethyl acetate (CAS 2230679-62-4), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyrimidinyl]oxy]-2-pyrimidinyl]oxy]methyl acetate (CAS 2158275-73-9), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyrimidinyl]oxy]-2-pyrimidinyl]oxy]ethyl acetate (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyrimidinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-Dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyrimidinyl]oxy]-2-pyrimidinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS 2158276-22-1), 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazole carboxylate ethyl ester (CAS 1949837-17-5); b5) Select from the group of whitening herbicides: PDS inhibitors: beflubutamide, diflufenican, fluridone, flurochloridone, flurutamon, norflurazon, picolinafene, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), limisoxafene, HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, chromazon, fenquinotrione, isoxaflutol, mesotrione, oxotrione (CAS 180608-33-7) 1486617-21-3), pyrasulfolol, pyrazolinate, pyrazoxyfen, sulcotrione, tefuryltrione, tenbotrione, tolpyralate, topramezon, bipirazon, fenpyrazon, cypirafluone, tripyrasulfone, benkitrion, dioxopyritrion; whitening agents, unknown target: acroniphen, amitorolflumezulone, 2-chloro-3-methylsulfanyl-N-(1-methyltetrazole-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), bixlozone, and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7), brocorozone, fursulfinum, iptriazopyride, and pyraquinate, b6) From the group of EPSP synthase inhibitors: Glyphosate, glyphosate-isopropylammonium, glyphosate-potassium, and glyphosate-trimethium (sulfosate); b7) From the group of glutamine synthetase inhibitors: Viranafos (biaraphos), viranafos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium, and glufosinate-P-ammonium. b8) DHP synthase inhibitors: Ashram; b9) Selected from the group of mitotic inhibitors: Compounds of group K1: dinitroanilines, e.g., benfluralin, butralin, dinitramine, ethalfluralin, fluroralin, oryzarin, pendimethalin, prodiamine and trifluralin; phosphoramidates, e.g., amiprofos, amiprofos-methyl and butamiphos; benzoic acid herbicides, e.g., chlortal, chlortal-dimethyl, pyridine, e.g., dithiopyr and thiazopyr; benzamides, e.g., propizamide and tebutam; compounds of group K2: carbetamide, chlorprofam, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and profam; and icaforin; among these, compounds of group K1, particularly dinitroanilines, are preferred; b10) Select from the group of VLCFA inhibitors: Chloroacetamides, e.g., acetochlor, alacrol, amidochlor, butachlor, dimetachlor, dimethenamid, dimethenamid-P, metazachlor, metrachlor, metrachlor-S, petoxamide, pretilachlor, propachlor, propisochlor, and tenylchlor, oxyacetanilides, e.g., flufenacet and mefenacet, acetanilides, e.g., difenamide, naproanilide, napropamide, and napropamide-M, tetrazolinones, e.g., fentrazamide, and other herbicides, e.g., anirofos, cafenstrol, phenoxasulfone, ibufencarbazone, piperofos, pyroxasulfone, dimesulfazet, and formulas II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.

8. and II.

9. Isoxazoline compounds 【Chemistry 2】 The isoxazoline compounds of formula (II) are known in the art, for example, from International Publication No. 2006 / 024820, International Publication No. 2006 / 037945, International Publication No. 2007 / 071900, and International Publication No. 2007 / 096576; Among VLCFA inhibitors, chloroacetamide, isoxazoline, and oxyacetamide are preferred; b11) Select from the group of cellulose biosynthesis inhibitors: Chlorthiamide, diclobenyl, flupoxam, indadiflame, isoxaben, triaziflame, and 1-cyclohexyl-5-pentafluorophenyloxy-1 ４ -[1,2,4,6]thiatriazine-3-ylamine (CAS 175899-01-1); b12) Derived from the group of deconjugating herbicides: Dinoseb, dinoterb, and DNOC, and their salts; b13) Select from the group of auxin herbicides: 2,4-D and its salts and esters, e.g., crasiphos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralide and its salts, e.g., aminopyralide-dimethylammonium, aminopyralide-tris(2-hydroxypropyl)ammonium and its esters, benzoline, benzoline-ethyl, chloramben and its salts and esters, clomeprop, clopyralide and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxiphene, fluroxypyr, fluroxypyr-butomethyl, fluroxypyr-meptyl, harauxifene and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinchlorac, kinmelac, TBA(2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)picolinic acid (CAS 1629965-65-6), and fluchloraminopyr; b14) Derived from the group of auxin transport inhibitors: fluchloraminopil, diflufenzopil, diflufenzopil sodium, naptaram, and naptaram sodium; b15) Selected from the group of other herbicides: bromobutide, chlorflurenol, chlorflurenol methyl, scinmethiline, cumylon, cyclopyrimolate, and their salts and esters, darapon, dazomet, diphenzocoat, diphenzocoat-methylsulfate, dimethipine, DSMA, dimuron, endotal and its salts, etobenzanide, flurenol, flurenol-butyl, flu Luprimidol, fosamine, fosamine-ammonium, indanophan, maleate hydrazide, mefluidide, metam, methiozoline, methylazide, methylbromide, methyldimuron, methyliodide, MSMA, oleic acid, oxadiclomefone, pelargonic acid, pyributicarb, quinoclamin, tetoflupyrrolimet, tridiphan, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methylpyridazin-3-one (CAS 2414510-21-5) The combination according to claim 1, selected from the compounds.

3. The combination according to claim 1 or 2, wherein the active compound b) comprises at least one compound (II) selected from the compounds of group b1): cretodyme, clodinahop-propargyl, cyhalofop-butyl, metamihop, propoxydime, quizalohop-ethyl, cethoxydime, prosulfocarb, and triarate.

4. The combination according to claim 1 or 2, wherein the active compound b) comprises at least one compound (II) selected from the compounds of group b2): mesosulfuron, pyrazosulfuron-ethyl, imazamox, imazetapyr, dicloslam, penoxulam, pyroxulam, bispyribac-sodium, thiencarbazone-methyl; and triafamone.

5. The combination according to claim 1 or 2, wherein the active compound b) comprises at least one compound (II) selected from the compounds of group b3): atrazine, metrivudine, terbutyrazine, bromoxynil and its salts and esters, bentazone and bentazone-sodium, and propanil.

6. The combination according to claim 1 or 2, wherein the active compound b) comprises at least one compound (II) selected from the compounds of group b4): flumioxazine, saflufenacyl, trifludimoxazine, epiriphenacyl, and 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyrimidinyl]oxy]phenoxy]ethyl acetate (CAS 2158274-50-9).

7. The combination according to claim 1 or 2, wherein the active compound b) comprises at least one compound (II) selected from the compounds of group b5): diflufenican, picolinaphene, chromazon, isoxaflutol, mesotrione, topramezone, acroniphene, and bixrozone.

8. The combination according to claim 1 or 2, wherein the active compound b) comprises at least one compound (II) selected from the compounds of group b6) and group b7): glyphosate, glyphosate-isopropylammonium, glyphosate-potassium, and glyphosate-trimethium(sulfosate) glufosinate, glufosinate-P, glufosinate-ammonium, and glufosinate-P-ammonium.

9. The combination according to claim 1 or 2, wherein the active compound b) comprises at least one compound (II) selected from the compounds of group b9: pendimethaline, trifluraline; propizamide.

10. The active compound b) is a compound from group b10): The combination according to claim 1 or 2, comprising at least one compound (II) selected from acetochlor, butachlor, dimethenamide-P, metazachlor, metrachlor, metrachlor-S, pretilachlor, and fluphenacetpyroxasulfone.

11. The combination according to claim 1 or 2, wherein the active compound b) comprises at least one compound (II) selected from the compounds of group b11): indadiphram and isoxaben.

12. The active compound b) is a compound from group b13): The combination according to claim 1 or 2, comprising at least one compound (II) selected from 2,4-D and its salts and esters, and dicamba and its salts and esters.

13. The active compound b) is a compound from group b15): The combination according to claim 1 or 2, comprising at least one compound (II) selected from scinmethiline, oxadiclomefone, cyclopyrimolate, tetoflupyrrolimet, and 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methylpyridazin-3-one (CAS 2414510-21-5).

14. Use of the combination according to claim 1 or 2 for controlling undesirable vegetation.

15. The use according to claim 14 for controlling undesirable vegetation in crop plants.

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