Substituted 2-c-azines and salts thereof, and use thereof as herbicidal active substances

Abstract

The invention relates to substituted 2-C-azines of general formula (I) and the use thereof as herbicides, in particular for controlling weeds and / or weed grasses in crops of useful plants and / or as plant growth regulators for influencing the growth of crops of useful plants. The present invention also relates to herbicidal and / or plant growth-regulating agents comprising one or more compounds of general formula (I).

Description

[0001] Substituted 2-C-azines and their salts and their use as herbicidal active ingredients

[0002] Description

[0003] The invention relates to the technical field of plant protection products, in particular herbicides for the selective control of weeds and grass weeds in crops.

[0004] Specifically, this invention relates to substituted 2-C-azines and their salts, processes for their preparation and their use as herbicides.

[0005] Previously known plant protection products for the selective control of weeds in crops or active substances for controlling undesirable plant growth sometimes have disadvantages in their use, either because they (a) have no or insufficient herbicidal activity against certain weeds, (b) have an insufficiently narrow spectrum of weeds that can be controlled with one active substance, (c) have insufficient selectivity in crops, and / or (d) have a toxicologically unfavorable profile. Furthermore, some active substances that can be used as plant growth regulators in some crops lead to undesirably reduced crop yields in others or are incompatible with the crop or only compatible within a narrow application rate range.Some of the known active ingredients cannot be produced economically on an industrial scale due to difficult-to-access precursors and reagents, or they have insufficient chemical stability. For other active ingredients, their effectiveness depends too heavily on environmental conditions, such as weather and soil conditions.

[0006] The herbicidal activity of these known compounds, especially at low application rates, and their tolerance to crop plants remain in need of improvement.

[0007] Heteroaryloxybenzenes, which have been attributed herbicidal activity, have been described in AU535637, EP8192, EP61913, JP61236766, WO2016 / 196606, W02021 / 204706, GB2594931, and W02016 / 010731, among others. Heteroaryloxypyridines, which have been attributed herbicidal activity, have been described in W02020 / 002089 and W02022 / 002838. 2-Heteroarylaminobenzenes, which have been attributed herbicidal activity, have been described in WO2020 / 193474.

[0008] Substituted 2-C-azines or their salts, however, have not yet been described as herbicidal active ingredients. Surprisingly, it has now been discovered that certain substituted 2-C-azines or their salts are particularly suitable as herbicidal active ingredients.

[0009] The present invention relates to substituted 2-C-azines of the general formula (I) or their salts wherein

[0010] A for nitrogen or CR 1 stands,

[0011] R 1 represents hydrogen, CN or halogen,

[0012] B for CH, CR 2 or N stands,

[0013] Q is Y-(C2-C6)-haloalkyl, where Y is a direct bond, oxygen, S(O) n , CO or OSO2, or

[0014] Q is Z-aryl or Z-heteroaryl, where aryl is substituted with 1 to 5 substituents, independently selected from the group R 4, wherein heteroaryl is substituted with up to 2 substituents, independently selected from the group R 4 , is substituted, and where Z is direct bond, O, S(O) n or CH2 means

[0015] R 2 independently of one another represent halogen, cyano, nitro, amino, (Ci-C4)-alkyl, (Ci-C-haloalkyl, cyclopropyl, (Ci-C4)-alkoxy, (Ci-CO-haloalkoxy or (Ci-C4)-alkyl-S(O) n - stands, m is equal to 0, 1, 2, or 3, n is equal to 0, 1 , or 2, R 3 for hydrogen, halogen, cyano, nitro, (C1-C4)-alkyl, (Ci-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C2) -haloalkoxy or (Ci-C4)-alkyl-S (O) n - stands, under the condition that if A for CR 1 stands, R 3 must not be hydrogen,

[0016] R 4 for halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-Cs)-haloalkyl, (C1-C4)-alkoxy, (C1-C2)-

[0017] Haloalkoxy, (C1-C4)-alkoxymethyl, (Ci-C4)-alkyl-S(O) n - stands, and

[0018] R 5 stands for hydrogen or CN.

[0019] The compounds of general formula (I) can form salts by addition of a suitable inorganic or organic acid, such as, for example, mineral acids such as HCl, HBr, H2SO4, HiPO or HNO3, or organic acids, e.g., carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids such as, for example, p-toluenesulfonic acid, to a basic group such as, for example, amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which are present in deprotonated form, such as, for example, sulfonic acids, certain sulfonic acid amides or carboxylic acids, can form internal salts with protonatable groups, such as amino groups. Salt formation can also occur through the action of a base on compounds of general formula (I).Suitable bases include, for example, organic amines, such as trialkylamines, morpholine, piperidine, and pyridine, as well as ammonium, alkali, or alkaline earth metal hydroxides, carbonates, and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate, and sodium and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines, or quaternary ammonium salts, for example with cations of the formula [NR. a R b R c R d ] + , where R a to R deach independently represents an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl. Alkylsulfonium and alkylsulfoxonium salts, such as (Ci-C) trialkylsulfonium and (Ci-C) trialkylsulfoxonium salts, are also suitable.

[0020] Depending on external conditions such as pH, solvent, and temperature, the substituted 2-C-azines of the general formula (I) according to the invention may possibly exist in various tautomeric structures, all of which are encompassed by the general formula (I). Hereinafter, the compounds of the formula (I) and their salts used according to the invention are referred to as "compounds of the general formula (I)".

[0021] Particularly preferred subject matter of the invention are compounds of the general formula (I) in which

[0022] A for nitrogen or CR 1 stands,

[0023] R 1 represents hydrogen, CN or halogen,

[0024] B for CH, CR 2 or N stands,

[0025] Q is Y-(C3-C5)-haloalkyl, where Y is a direct bond, oxygen, S(O) n , CO or OSO2, or

[0026] Q is Z-aryl or Z-heteroaryl, where aryl is substituted with 1 to 3 substituents independently selected from the group R 4 , wherein heteroaryl is substituted with up to 2 substituents, independently selected from the group R 4 , is substituted, and where Z is direct bond, O, S(O) n or CH2 means

[0027] R 2 independently for halogen, cyano, nitro, amino, (Ci-C4)-alkyl, (Ci-C -haloalkyl, cyclopropyl, (Ci-CO-alkoxy, (Ci-CO-haloalkoxy or (Ci-C4)-alkyl-S(O) n - m is equal to 0, 1, 2 or 3, n is equal to 0, 1 or 2,

[0028] R 3represents hydrogen, halogen, cyano, (Ci-C4)-alkyl, (Ci-C -haloalkyl, (C1-C4)-alkoxy or (Ci-C2)-haloalkoxy, with the proviso that when A represents CR 1 stands, R 3 must not be hydrogen,

[0029] R 4 represents halogen, cyano, (Ci-C4)-alkyl, (Ci-C5)-haloalkyl, (C1-C4)-alkoxymethyl, and

[0030] R 5 represents hydrogen or CN. A particularly preferred subject of the invention are compounds of the general formula (I) in which

[0031] A for nitrogen or CR 1 stands,

[0032] R 1 represents hydrogen, cyano, fluorine or chlorine,

[0033] B for CH, CR 2 or N stands,

[0034] Q is Y-(C3-Cs)-haloalkyl, where Y is a direct bond, oxygen, S, CO or OSO2, or

[0035] Q is Z-aryl or Z-heteroaryl, where aryl is substituted with 1 or 2 substituents independently selected from the group R 4 , wherein heteroaryl is substituted with up to 2 substituents, independently selected from the group R 4 , and where Z is a direct bond, O, S or CH2,

[0036] R 2 independently of one another represents fluorine, chlorine, bromine, cyano, methyl, CF3 or methoxy, m is 0, 1 or 2,

[0037] R 3 represents hydrogen, chlorine, bromine, fluorine, cyano, methyl, CF3, methoxy or CHF2O, with the proviso that when A represents CR 1 stands, R 3 must not be hydrogen,

[0038] R 4 represents fluorine, chlorine, methyl, CHF2, CF3 or methoxymethyl, and

[0039] R 5 stands for hydrogen or CN.

[0040] Also further preferred subject matter of the invention are compounds of the general formula (I), in which

[0041] A for nitrogen or CR 1 stands,

[0042] R 1 stands for hydrogen, cyano, fluorine or chlorine, B stands for CH, CR 2 or N stands,

[0043] Q is Y-(C3-C5)-haloalkyl, where Y is a direct bond, oxygen, S, CO or OSO2, or

[0044] Q is Z-aryl or Z-heteroaryl, where aryl is substituted with 1 or 2 substituents independently selected from the group R 4 , wherein heteroaryl is substituted with up to 2 substituents, independently selected from the group R 4 , and where Z is a direct bond, O, S or CH2,

[0045] R 2 independently of one another represents fluorine, chlorine, bromine, cyano, methyl, CF3 or methoxy, m is 0, 1 or 2,

[0046] R 3represents hydrogen, chlorine, bromine, fluorine, cyano, methyl, CF3, methoxy or CHF2O, with the proviso that when A represents CR 1 stands, R 3 must not be hydrogen,

[0047] R 4 represents fluorine, chlorine, methyl, CHF2, CF3 or methoxymethyl, and

[0048] R 5 stands for hydrogen or CN.

[0049] Also further preferred subject matter of the invention are compounds of the general formula (I), in which

[0050] A stands for nitrogen, CH, CCN or CF,

[0051] B stands for CH,

[0052] Q für (CH2)3CF3, (CH2)4CF3, S(CH2)3CF3, S(CH2)3C1 , SO(CH2)3C1 , SO(CH2)2CF3, SO(CH2)3CF3, SO2(CH2)3CF3, O(CH2)3CF3, C(O)(CH2)3CF3, OSO2(CH2)2CF3, OSO2(CH2)3CF3, OSO2(CH2)3C1, 4-Fluorbenzyl, 4-Chlorphenyl, 3,4-Difluorphenyl, 4-Fluorphenoxy, 5-C1- pyrimidin-2-oxy, 5-F-pyrimidin-2-oxy, 5-Cl-3-F-pyridin-2-oxy, 4-Fluorphenylsulfanyl, 2,4-Ch- phenylsulfonyl, 2,4-C12-phenylsulfanyl, 2,4-C12-phenylsulfinyl, 3-(CHF2)-isoxazol-5-yl, 5- (CHF2)-isoxazol-3-yl, l,2,4-oxadiazol-3-yl, 5-Methyl-l,2,4-oxadiazol-3-yl, 5-(CHF2)- 1,2,4- oxadiazol-3-yl, 5-(CF3)-l,2,4-oxadiazol-3-yl, 5-Cl-pyrimidin-2-yl-sulfanyl, 5-Cl-pyrimidin-2-yl- sulfinyl, 5-Cl-pyrimidin-2-yl-sulfonyl, 5-F-pyrimidin-2-yl-sulfanyl, 4-(CF3)-pyrazol-l-yl, 4-C1- pyrazol-l-ylmethyl, 4-Br-pyrazol-l-ylmethyl oder 4-(CF3)-pyrazol-l-ylmethyl steht,

[0053] R 2 unabhängig voneinander für Fluor, Chlor, Brom, Cyano, Methyl, CF3 oder Methoxy steht, m ist gleich 0, 1 oder 2,

[0054] R 3represents chlorine, bromine or fluorine and

[0055] R 5 stands for hydrogen or CN.

[0056] A particularly preferred subject of the invention are compounds of the general formula (I), in which

[0057] A stands for nitrogen, CH or CF,

[0058] B stands for CH,

[0059] Q for (CH2)3CF3, S(CH2)3CF3, SO(CH2)3CF3, O(CH2)3CF3, OSO2(CH2)3CF3, OSO2(CH2)3C1, 4-fluorobenzyl, 3,4-difluorophenyl, 4-fluorophenoxy, 4-fluorophenylsulfanyl, 2,4-Cl2-phenylsulfanyl, 4-(CF3)-pyrazol-l-yl, 5-Cl-pyrimidin-2-oxy, 5-F-pyrimidin-2-oxy, 5-C1-3-F-pyridin-2-oxy, 3-(CHF2)-isoxazol-5-yl or 5-methyl-l,2,4-oxadiazol-3-yl,

[0060] R 2 independently of one another represents fluorine, chlorine, bromine, cyano, methyl, CF3 or methoxy, m is 0, 1 or 2,

[0061] R 3 represents chlorine, bromine or fluorine and

[0062] R 5 stands for hydrogen or CN.

[0063] The above general or preferred radical definitions apply both to the end products of the general formula (I) and, accordingly, to the starting materials or intermediates required for their preparation. These radical definitions can be combined with each other, including within the given preferred ranges.

[0064] Particularly for reasons of higher herbicidal activity, better selectivity and / or better producibility, compounds according to the invention of the general formula (I) mentioned or salts thereof or the use thereof according to the invention are of particular interest in which individual radicals have one of the preferred meanings already mentioned or mentioned below, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.

[0065] With regard to the compounds according to the invention, the terms used above and below are explained. These are familiar to the person skilled in the art and have, in particular, the meanings explained below:

[0066] Unless otherwise defined, the general rule for the designation of chemical groups is that the connection to the skeleton or the rest of the molecule is made via the last-mentioned structural element of the chemical group in question, e.g. in the case of (C1-C4)-alkoxy via the oxygen atom, in the case of (Ci-C4)-alkyl-S(O) n - via the sulfur atom and in the case of (C1-C4)-alkoxymethyl via the C atom of the methyl group.

[0067] The term "halogen" means, for example, fluorine, chlorine, bromine, or iodine. When used for a radical, "halogen" means, for example, a fluorine, chlorine, bromine, or iodine atom.

[0068] The term "(C1-C4)-alkyl" used here as an example is a shorthand notation for straight-chain or branched alkyl with one to four carbon atoms, corresponding to the range specified for carbon atoms, i.e., it includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl, or tert-butyl. General alkyl radicals with a larger specified range of carbon atoms, e.g., "(C2-C6)-alkyl," correspondingly also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, i.e., according to the example, also the alkyl radicals with 5 and 6 carbon atoms.

[0069] “HaloalkyF” means alkyl which is partially or fully substituted by identical or different halogen atoms, e.g. monohaloalkyl (= monohaloalkyl) such as CH2CH2Cl, CH2CH2Br, CHC1CH3, CH2Cl, CH2F, CH2CH2CF3; perhaloalkyl such as CC13, CCIF2, CFCI2, CF2CCIF2, CF2CCIFCF3; polyhaloalkyl such as CH2CHFC1, CF2CC1FH, CF2CBrFH, CH2CF3; the term perhaloalkyl also includes the term perfluoroalkyl. “Alkoxy” means an alkyl radical bonded via an oxygen atom, e.g. B. (but not limited to) (Ci-C4)-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy.

[0070] “Haloalkoxy” is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2C1.

[0071] The term “aryl” means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.

[0072] If a basic structure is substituted "by one or more residues" from a list of residues (= group) or a generically defined group of residues, this includes the simultaneous substitution by several identical and / or structurally different residues.

[0073] According to the invention, the term “heteroaryl” stands for heteroaromatic compounds, ie completely unsaturated aromatic heterocyclic compounds, preferably for 5- to 7-membered rings with 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N. Heteroaryls according to the invention are, for example, IH-pyrrol-1-yl; IH-pyrrol-2-yl; IH-pyrrol-

[0074] 3-yl; furan-2-yl; furan-3-yl; thien-2-yl; Thien-3-yl, IH-imidazol-l-yl; lH-imidazol-2-yl; IH-imidazole

[0075] 4-yl; lH-Imidazol-5-yl; IH-Pyrazol-l-yl; lH-Pyrazol-3-yl; lH-Pyrazol-4-yl; lH-Pyrazol-5-yl, 1H-1,2,3- Triazol-l-yl, lH-l,2,3-Triazol-4-yl, lH-l,2,3-Triazol-5-yl, 2H-l,2,3-Triazol-2-yl, 2H-l,2,3-Triazol-4-yl, lH-l,2,4-Triazol-l-yl, lH-l,2,4-Triazol-3-yl, 4H-l,2,4-Triazol-4-yl, l,2,4-Oxadiazol-3-yl, 1,2,4- Oxadiazol-5-yl, l,3,4-Oxadiazol-2-yl, l,2,3-Oxadiazol-4-yl, l,2,3-Oxadiazol-5-yl, l,2,5-Oxadiazol-3-yl, Azepinyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, l,3,5-Triazin-2-yl, l,2,4-Triazin-3-yl, l,2,4-Triazin-5-yl, l,2,4-Triazin-6-yl, l,2,3-Triazin-4-yl, l,2,3-Triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- und 1,2,6-Oxazinyl, Isoxazol-3-yl, Isoxazol-4-yl, Isoxazol-5-yl, l,3-Oxazol-2-yl, l,3-Oxazol-4-yl, 1,3- Oxazol-5-yl, Isothiazol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, l,3-Thiazol-2-yl, l,3-Thiazol-4-yl, 1,3- Thiazol-5-yl, Oxepinyl, Thiepinyl, 1 ,2,4-Triazolonyl und 1 ,2,4-Diazepinyl,2H-l,2,3,4-tetrazol-5-yl, lH-l,2,3,4-tetrazol-5-yl, l,2,3,4-oxatriazol-5-yl, l,2,3,4-thiatriazol-5-yl, l,2,3,5-oxatriazol-4-yl, l,2,3,5-thiatriazol-4-yl. The heteroaryl groups according to the invention can further be substituted by one or more identical or different radicals. If two adjacent,

[0076] Carbon atoms are part of another aromatic ring, then these are fused heteroaromatic systems, such as benzofused or multiply fused heteroaromatics. Preferred are, for example, quinolines (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); isoquinolines (e.g. isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyr azine; pyridopyrimidines; pyridopyridazines; pteridines; Pyrimidopyrimidines.Examples of heteroaryl are also 5- or 6-membered benzo-fused rings from the group IH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, lH-indol-4-yl, lH-indol-5-yl, 1H-indol-6-yl, lH-indol-7-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran-5-yl, l-benzofuran-6-yl, l-benzothiophen-7-yl, l-benzothiophen-2-yl, l-benzothiophen-3-yl, 1-benzothiophen-4-yl, l-benzothiophen-5-yl, l-benzothiophen-6-yl, l-benzothiophen-7-yl, IH-indazol-.

[0077] 1-yl, lH-Indazol-3-yl, lH-Indazol-4-yl, lH-Indazol-5-yl, lH-Indazol-6-yl, lH-Indazol-7-yl, 2H-Indazol-

[0078] 2-yl, 2H-Indazol-3-yl, 2H-Indazol-4-yl, 2H-Indazol-5-yl, 2H-Indazol-6-yl, 2H-Indazol-7-yl, 2H- Isoindol-2-yl, 2H-Isoindol-l-yl, 2H-Isoindol-3-yl, 2H-Isoindol-4-yl, 2H-Isoindol-5-yl, 2H-Isoindol-6-yl; 2H-Isoindol-7-yl, IH-Benzimidazol-l-yl, lH-Benzimidazol-2-yl, lH-Benzimidazol-4-yl, 1H- Benzimidazol-5-yl, lH-Benzimidazol-6-yl, lH-Benzimidazol-7-yl, l,3-Benzoxazol-2-yl, 1,3- Benzoxazol-4-yl, l,3-Benzoxazol-5-yl, l,3-Benzoxazol-6-yl, l,3-Benzoxazol-7-yl, l,3-Benzthiazol-2-yl, l,3-Benzthiazol-4-yl, l,3-Benzthiazol-5-yl, l,3-Benzthiazol-6-yl, l,3-Benzthiazol-7-yl, 1,2- Benzisoxazol-3-yl, l,2-Benzisoxazol-4-yl, l,2-Benzisoxazol-5-yl, l,2-Benzisoxazol-6-yl, 1,2- Benzisoxazol-7-yl, l,2-Benzisothiazol-3-yl, 1 ,2-Benzisothiazol-4-yl, l,2-Benzisothiazol-5-yl, 1,2- Benzisothiazol-6-yl, 1 ,2-Benzisothiazol-7-yl.

[0079] If the compounds can form tautomers through hydrogen shift that are not structurally covered by the general formula (I), these tautomers are nevertheless encompassed by the definition of the compounds of the general formula (I) according to the invention, unless a specific tautomer is considered. For example, many carbonyl compounds can exist in both the keto and enol forms, with both forms being encompassed by the definition of the compound of the general formula (I).

[0080] The compounds of general formula (I) can exist as stereoisomers depending on the nature and linkage of the substituents. The possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z- and E-isomers, are all encompassed by general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z- and E-isomers) can occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers can be obtained from the mixtures obtained during production using conventional separation methods. Chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or diastereomeric excess, and on a preparative scale to produce test samples for biological testing.Likewise, stereoisomers can be selectively prepared by employing stereoselective reactions using optically active starting materials and / or auxiliaries. The invention thus also relates to all stereoisomers encompassed by the general formula (I) but not specified with their specific stereoform, as well as mixtures thereof.

[0081] If the compounds are obtained as solids, purification can also be carried out by recrystallization or digestion. If individual compounds of general formula (I) cannot be satisfactorily obtained by the methods described below, they can be prepared by derivatization of other compounds of general formula (I).

[0082] Suitable methods for the isolation, purification, and stereoisomer separation of compounds of general formula (I) include methods generally known to the skilled person from analogous cases, e.g., physical processes such as crystallization, chromatography, especially column chromatography and HPEC (high-pressure liquid chromatography), distillation, optionally under reduced pressure, extraction, and other processes. Any remaining mixtures can generally be separated by chromatographic separation, e.g., on chiral solid phases. For preparative quantities or on an industrial scale, processes such as crystallization, e.g., of diastereomeric salts, which can be obtained from the diastereomer mixtures with optically active acids and, if acidic groups are present, with optically active bases, are suitable.

[0083] The present invention also claims processes for preparing the compounds of general formula (I) according to the invention.

[0084] The compounds of general formula (I) according to the invention can be prepared, inter alia, using known methods. The synthetic routes used and investigated start from commercially available or easily prepared building blocks. The groups A, B, Q, R 2 , R 3 and m of the general formula (I) have the meanings defined above in the following schemes, unless exemplary but non-limiting definitions are given.

[0085] Compounds according to the invention can be prepared, for example, by the method shown in Scheme 1 below.

[0086] Scheme 1.

[0087] The pyri(mi)dines of general formula (Ia) can be prepared by coupling the corresponding acetonitriles (EI) with the pyri(mi)dines (EIl), where LG is a leaving group, in the presence of, for example, a base. The required base can be, for example, a carbonate salt of an alkali metal (such as sodium or potassium) or a hydride of an alkali metal (such as sodium). The reactions are generally carried out in an organic solvent, such as dioxane, dimethyl sulfoxide, or dimethylformamide, at temperatures between 0°C and the boiling point of the solvent.

[0088] The pyri(mi)dines of general formula (Ib) can be prepared, for example, by decarboxylative saponification of the corresponding acetonitriles (Ia). Suitable conditions include, for example, aqueous acids (such as hydrochloric acid) and heating to the boiling point.

[0089] The acetonitriles of the general formula (EI) are known from the literature and can be prepared, for example, according to the methods described in Helvetica Chimica Acta (2003), 86(2), 343-360, in Angewandte Chemie, International Edition (2011), 50(19), 4470-4474 and similarly.

[0090] Selected detailed synthesis examples for the compounds of general formula (I) according to the invention are listed below. The 'H-NMR, 13 C-NMR and 19 F-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for 'H-NMR and 150 MHz for 13 C-NMR and 375 MHz at 19F-NMR, solvent CDCl, CD3OD or de-DMSO, internal standard: tetramethylsilane 5 = 0.00 ppm), were obtained using a Broker instrument. The designated signals have the following meanings: b = broad; s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of a double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. For mixtures of diastereomers, either the significant signals of both diastereomers or the characteristic signal of the major diastereomer are given. The abbreviations used for chemical groups have the following meanings: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl. Synthesis examples:

[0091] Table example number 1-34: (5-chloropyrimidin-2-yl)[3-fluoro-2-(4-fluorophenoxy)phenyl]acetonitrile

[0092] Synthesis step 1: 3-fluoro-2-(4-fluorophenoxy)benzaldehyde

[0093] A solution of 2.0 g of 2,3-difluorobenzaldehyde (14.1 mmol, 1.0 eq), 2.37 g of 2-fluorophenol (21.1 mmol, 1.5 eq), and 3.89 g of potassium carbonate (28.1 mmol, 2.0 eq) in 30 ml of DMF was stirred at 100 °C for 3 h. The mixture was then diluted with 50 ml of ether and washed with 2N sodium hydroxide solution (30 ml of sodium hydroxide solution) and saturated brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography. The yield was 2.82 g (85%). 'H NMR (400.0 MHz, CDCl3): 10.35 (s, 1H); 7.75 (m, 1H); 7.43 (m, 1H); 7.32 (m,lH); 7.01 (m,2H); 6.91 (m.2H).

[0094] Synthesis step 2: 3-fluoro-2-(4-fluorophenoxy)benzyl alcohol

[0095] 0.91 g of sodium borohydride (24 mmol, 2.0 eq) was added to 2.8 g of 3-fluoro-2-(4-fluorophenoxy)benzaldehyde (12 mmol, 1.0 eq) in a mixture of 44 mL of THF and 22 mL of MeOH, and the mixture was stirred at room temperature for 3 h. Water was then added to the solution and the mixture was extracted with ethyl acetate. The organic phase was concentrated in vacuo, and the residue was taken up in dichloromethane, dried over sodium sulfate, and concentrated in vacuo. The resulting product was used without further purification. The yield was 2.77 g (98% crude). 'H NMR (400.0 MHz, CDCl): 7.30 (m, 1H); 7.23 (m, 1H); 7.13 (m, 1H); 6.97 (m, 2H); 6.84 (m, 2H); 4.69 (s,2H); 1.79 (bs,lH) Synthesis step 3: 3-fluoro-2-(4-fluorophenoxy)benzyl chloride

[0096] A solution of 2.70 g of 3-fluoro-2-(4-fluorophenoxy)benzyl alcohol (11.4 mmol, 1.0 eq) in 18 mL of toluene was treated with 1.0 mL of thionyl chloride and stirred at room temperature for 5 h. The mixture was then added to water and extracted with dichloromethane. The organic phase was dried with sodium sulfate and concentrated in vacuo. The resulting product was used without further purification. The yield was 3.29 g (100% crude). 'H NMR (400.0 MHz, CDCl): 7.31-7.12 (m, 3H); 6.98 (m, 2H); 6.87 (m, 2H); 4.60 (s, 2H)

[0097] Synthesis step 4: (3-fluoro-2-(4-fluorophenoxy)phenyl)acetonitrile

[0098] 3.2 g of 3-fluor-2-(4-fluorophenoxy)benzyl chloride (12.6 mmol, 1.0 eq) and 982 mg of potassium cyanide (15.1 mmol, 1.2 eq) were heated under reflux for 6 h in a mixture of 5 ml of water and 25 ml of ethanol. The mixture was then concentrated, and the residue was taken up in dichloromethane. The organic phase was dried with sodium sulfate, concentrated in vacuo, and the residue was purified by column chromatography. The yield was 1.46 g (47%). 'H NMR (400.0 MHz, CDCl): 7.33 (m, 1H); 7.26 (m, 1H); 7.18 (m, 1H); 6.99 (m, 2H); 6.83 (m, 2H); 3.72 (s, 2H); Synthesis step 5: (5-chloropyrimidin-2-yl)[3-fluoro-2-(4-fluorophenoxy)phenyl]acetonitrile

[0099] 179 mg of sodium hydride (60%) (4.49 mmol, 2.2 eq) was added to 500 mg of (3-fluoro-2-(4-fluorophenoxy)phenyl)acetonitrile (2.0 mmol, 1.0 eq) in 15 mL of THF, and the mixture was stirred at room temperature for 30 min. Subsequently, 365 mg of 2,5-dichloropyrimidine (2.45 mmol, 1.2 eq) were added and the mixture was stirred overnight at room temperature. The mixture was then treated with 2N hydrochloric acid and extracted with dichloromethane. The organic phase was dried with sodium sulfate, concentrated in vacuo, and the residue was purified by column chromatography. The yield was 631 mg (87%). Table Example 1-35: 5-Chloro-2-[3-fluoro-2-(4-fluorophenoxy)benzyl]pyrimidine

[0100] 530 mg (5-chloropyrimidin-2-yl)[3-fluoro-2-(4-fluorophenoxy)phenyl]acetonitrile (1.48 mmol) in one

[0101] A mixture of 6 ml of glacial acetic acid and 2 ml of concentrated hydrochloric acid was stirred at 100°C for 8 h. The mixture was then concentrated, and the residue was purified by column chromatography. The yield was 200 mg (41%).

[0102] In analogy to the preparation examples given above and recited at the appropriate point, the compounds of the general formula listed below and shown in Table 1 are obtained

[0103] Table 1

[0104] In analogy to the preparation examples given above and recited at the appropriate point, the compounds of the general formula listed below and shown in Table 2 are obtained

[0105] Table 2 The NMR data of disclosed examples are listed either in classical form (3-value, number of H atoms, multiplet splitting) or as so-called NMR peak lists. In the NMR peak list method, the NMR data of selected examples are recorded in the form of NMR peak lists, with each signal peak listed first with the 3-value in ppm and then with the signal intensity separated by a space. The 8-value signal intensity pairs of different signal peaks are listed separated by semicolons.

[0106] The peak list of an example therefore has the form:

[0107] 3i (Intensity ; 82 (Intensity2); ; 8i (Intensity?; ; 8 n (Intensity)

[0108] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.

[0109] To calibrate the chemical shift of 'H NMR spectra, tetramethylsilane and / or the chemical shift of the solvent are used, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may or may not appear in NMR peak lists.

[0110] The lists of 'H-NMR peaks are similar to the classical 'H-NMR printouts and thus usually contain all peaks that are listed in a classical NMR interpretation.

[0111] In addition, like classical 'H-NMR printouts, they can show solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities.

[0112] When reporting compound signals in the delta region of solvents and / or water, our lists of 'H-NMR peaks show the common solvent peaks, for example, peaks of DMSO in de-DMSO and the peak of water, which usually have high intensity on average.

[0113] Such stereoisomers and / or impurities may be typical for the respective manufacturing process. Their peaks can thus help identify the reproduction of our manufacturing process based on "byproduct fingerprints."

[0114] An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also empirically evaluated expected values) can isolate the peaks of the target compounds as needed, applying additional intensity filters if necessary. This isolation would be similar to the peak picking involved in classical 1H NMR interpretation. Further details on 1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

[0115] NMR data of the final products (classical form):

[0116] The 'H NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for 'H NMR, solvent CDCl or de-DMSO, internal standard: tetramethylsilane 5 = 0.00 ppm) were obtained using a Broker instrument. The designated signals have the following meanings: b = broad; s = singlet, d = doublet, t = triplet, dd = doublet, ddd = doublet of a double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. For mixtures of diastereomers, either the significant signals of both diastereomers or the characteristic signal of the major diastereomer are given.

[0117] The present invention further relates to the use of one or more

[0118] Compounds of the general formula (I) and / or salts thereof, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1-1) to (1-209), (2-1) to (2-14) and / or salts thereof, each as defined above, as herbicide and / or plant growth regulator, preferably in

[0119] Crops of useful and / or ornamental plants.

[0120] The present invention further relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or salts thereof, as defined above, is preferably applied in one of the mixtures identified as preferred or particularly preferred.

[0121] Embodiment, in particular one or more compounds of the formulas (1-1) to (1-209), or (2-1) to (2-14) and / or salts thereof, in each case as defined above, or of an agent according to the invention, as defined below, to the (harmful) plants, (harmful) plant seeds, the soil in or on which the

[0122] (Harmful) plants grow, or the cultivated area is applied.

[0123] The present invention also relates to a method for controlling unwanted

[0124] Plants, preferably in crops, characterized in that an effective amount of one or more compounds of the general formula (I) and / or salts thereof, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulae (I-1) to (I-209), or (2-1) to (2-14) and / or salts thereof, in each case as defined above, or of an agent according to the invention, as defined below, is applied to undesired plants (e.g. harmful plants such as mono- or dicotyledonous weeds or undesired crop plants), the seed of the undesired plants (ie plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in or on which the undesired plants grow (e.g. the soil of cultivated land or non-cultivated land) or the cultivated area (iearea where the unwanted plants will grow).

[0125] The present invention furthermore also relates to a method for controlling the growth of plants, preferably of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-1) to (I-209), or (2-1) to (2-14) and / or salts thereof, in each case as defined above, or of an agent according to the invention, as defined below, is applied to the plant, the seed of the plant (ie plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in or on which the plants grow (e.g. the soil of cultivated land or non-cultivated land) or the cultivation area (ie area on which the plants will grow).

[0126] The compounds or compositions according to the invention can be applied, for example, by pre-sowing (optionally also by incorporation into the soil), pre-emergence, and / or post-emergence methods. Some representatives of the monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds according to the invention are mentioned as examples, without implying a restriction to specific species.

[0127] Preferably, in a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the general formula (I) and / or salts thereof are used for controlling harmful plants or for regulating the growth in crops of useful plants or ornamental plants, wherein the useful plants or ornamental plants are transgenic plants in a preferred embodiment.

[0128] The compounds of the general formula (I) according to the invention and / or salts thereof are suitable for controlling the following genera of monocotyledonous and dicotyledonous weeds: Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0129] Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0130] If the compounds of general formula (I) according to the invention are applied to the soil surface before the germination of the harmful plants (grass and / or weeds) (pre-emergence method), the emergence of the weed seedlings is either completely prevented or they grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.

[0131] When the active ingredients of the general formula (I) are applied to the green parts of the plant by post-emergence, growth stops after treatment and the weeds remain in the growth stage present at the time of application or die completely after a certain time, so that in this way weed competition that is harmful to the crop plants is eliminated very early and sustainably.

[0132] Although the compounds of the general formula (I) according to the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, are only insignificantly damaged or not damaged at all, depending on the structure of the respective compound according to the invention and the application rate thereof. For these reasons, the present compounds are very suitable for the selective control of unwanted plant growth in plant crops such as agricultural crops or ornamental plantings.Furthermore, the compounds of general formula (I) according to the invention (depending on their respective structure and the applied rate) exhibit outstanding growth-regulating properties in crop plants. They regulate the plant's own metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, for example, by inducing desiccation and stunting. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, since, for example, lodging can be reduced or completely prevented.

[0133] Due to their herbicidal and plant growth-regulating properties, the compounds of general formula (I) can also be used to control weeds in crops of plants modified genetically or by conventional mutagenesis. Transgenic plants are generally characterized by particularly advantageous properties, for example, resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria, or viruses. Other special properties affect, for example, the harvested product in terms of quantity, quality, storability, composition, and specific constituents. Thus, transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvested product, are known.

[0134] With regard to transgenic crops, preference is given to using the compounds of the general formula (I) according to the invention and / or their salts in economically important transgenic crops of useful and ornamental plants, e.g. cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.

[0135] Preferably, the compounds of general formula (I) according to the invention can also be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.

[0136] Due to their herbicidal and plant growth-regulating properties, the compounds of general formula (I) according to the invention can also be used to combat weeds in crops of known or yet-to-be-developed genetically modified plants. The transgenic plants are generally characterized by particularly advantageous properties, for example, resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria, or viruses. Other special properties relate, for example, to the harvested product in terms of quantity, quality, storability, composition, and specific constituents. Thus, transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvested product, are known.Other special properties may include tolerance or resistance to abiotic stressors such as heat, cold, drought, salt and ultraviolet radiation.

[0137] The use of the compounds of the general formula (I) according to the invention or their salts is preferred in economically important transgenic crops of useful and ornamental plants, e.g. cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.

[0138] Preferably, the compounds of general formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.

[0139] Conventional methods for producing new plants with modified traits compared to existing plants include classical breeding methods and the creation of mutants. Alternatively, new plants with modified traits can be created using genetic engineering techniques.

[0140] Numerous molecular biological techniques for producing new transgenic plants with modified traits are known to those skilled in the art. For such genetic manipulations, nucleic acid molecules can be introduced into plasmids, allowing mutagenesis or sequence modification through recombination of DNA sequences. Using standard methods, base substitutions can be performed, partial sequences can be removed, or natural or synthetic sequences can be added. Adapters or linkers can be attached to the DNA fragments to connect them to one another.

[0141] The production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme that specifically cleaves transcripts of the above-mentioned gene product.

[0142] For this purpose, DNA molecules can be used that contain the entire coding sequence of a gene product, including any flanking sequences present, or DNA molecules that contain only parts of the coding sequence. These parts must be long enough to produce an antisense effect in the cells. It is also possible to use DNA sequences that exhibit a high degree of homology to the coding sequences of a gene product, but are not completely identical.

[0143] When nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any compartment of the plant cell. However, to achieve localization in a specific compartment, the coding region can be linked to DNA sequences that ensure localization in a specific compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). Expression of nucleic acid molecules can also occur in the organelles of plant cells.

[0144] The transgenic plant cells can be regenerated into whole plants using known techniques. The transgenic plants can, in principle, be plants of any plant species, i.e., both monocotyledonous and dicotyledonous plants.

[0145] Transgenic plants are available that exhibit altered properties through overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

[0146] Preferably, the compounds of the general formula (I) according to the invention can be used in transgenic crops which are resistant to growth promoters, such as dicamba, or to herbicides which inhibit essential plant enzymes, e.g. acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoyl lisoxazoles and analogous active substances.

[0147] When the compounds of general formula (I) according to the invention are used in transgenic crops, in addition to the effects against weeds observed in other crops, effects often occur which are specific to the application in the respective transgenic crop, for example a modified or specifically expanded weed spectrum that can be controlled, modified application rates that can be used for application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing the growth and yield of the transgenic crops. The invention therefore also relates to the use of the compounds of general formula (I) according to the invention and / or salts thereof as herbicides for controlling weeds in crops of useful or ornamental plants, optionally in transgenic crops.

[0148] Preference is given to the use of compounds of the general formula (I) in cereals, preferably maize, wheat, barley, rye, oats, millet or rice, in pre- or post-emergence.

[0149] The use of compounds of general formula (I) in soybeans in pre- or post-emergence is also preferred.

[0150] The use of compounds of formula (I) according to the invention for controlling harmful plants or for regulating the growth of plants also includes the case in which a compound of general formula (I) or its salt is formed from a precursor substance ("prodrug") only after application to the plant, in the plant or in the soil.

[0151] The invention also relates to the use of one or more compounds of the general formula (I) or salts thereof or of an agent according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) or salts thereof is applied to the plants (harmful plants, optionally together with the useful plants), plant seeds, the soil in or on which the plants grow, or the area under cultivation.

[0152] The invention also relates to a herbicidal and / or plant growth regulating agent, characterized in that the agent

[0153] (a) contains one or more compounds of the general formula (I) and / or salts thereof as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulae (1-1) to (1-209) or (2-1) to (2-14) and / or salts thereof, each as defined above, and

[0154] (b) one or more further substances selected from groups (i) and / or (ii):

[0155] (i) one or more further agrochemically active substances, preferably selected from the

[0156] Group consisting of insecticides, acaricides, nematicides, other herbicides (i.e. those which do not correspond to the general formula (I) defined above), fungicides, safeners, fertilizers and / or other growth regulators,

[0157] (ii) one or more formulation aids commonly used in crop protection.

[0158] The further agrochemically active substances of component (i) of a composition according to the invention are preferably selected from the group of substances listed in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0159] A herbicidal or plant growth regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) customary in plant protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers which are solid at 25 °C and 1013 mbar, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably organic solvents which are miscible with water in any ratio at 25 °C and 1013 mbar.

[0160] The compounds of general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts, or granules in the usual preparations. The invention therefore also relates to herbicidal and plant growth-regulating compositions containing compounds of general formula (I) and / or salts thereof.

[0161] The compounds of general formula (I) according to the invention and / or their salts can be formulated in various ways, depending on the biological and / or chemical-physical parameters specified. Possible formulation options include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), seed dressings, granules for broadcast and soil application, granules (GR) in the form of microgranules, spray granules, coating granules, and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, and waxes.

[0162] These individual formulation types and the formulation aids such as inert materials, surfactants, solvents and other additives are known to the person skilled in the art and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ; Hv Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, NY; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0163] Wettable powders are preparations that are evenly dispersible in water. In addition to the active ingredient, they contain a diluent or inert substance as well as ionic and / or non-ionic surfactants (wetting agents, dispersants), e.g., polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyltaurine. To produce the wettable powders, the herbicidal active ingredients are finely ground in conventional equipment such as hammer mills, fan mills, and air jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.

[0164] Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g., butanol, cyclohexanone, dimethylformamide, xylene, or higher-boiling aromatics or hydrocarbons, or mixtures of organic solvents, with the addition of one or more ionic and / or non-ionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium salts of alkylarylsulfonic acid, such as calcium dodecylbenzenesulfonate, or non-ionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.

[0165] Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0166] Suspension concentrates can be water- or oil-based. They can be produced, for example, by wet grinding using commercially available bead mills and, if necessary, with the addition of surfactants, such as those listed above for the other formulation types.

[0167] Emulsions, e.g. oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and, if appropriate, surfactants, such as those already listed above for the other formulation types.

[0168] Granules can be produced either by spraying the active ingredient onto adsorbent, granulated inert material or by applying active ingredient concentrates to the surface of carrier materials such as sand, kaolinite, or granulated inert material using adhesives such as polyvinyl alcohol, sodium polyacrylate, or mineral oils. Suitable active ingredients can also be granulated in the usual way for the production of fertilizer granules—if desired, mixed with fertilizers.

[0169] Water-dispersible granules are usually produced by conventional processes such as spray drying, fluidized bed granulation, disc granulation, mixing with high-speed mixers and extrusion without solid inert material.

[0170] For the production of disc, fluidized bed, extruder, and spray granules, see, for example, the procedures in "Spray-Drying Handbook," 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration," Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook," 5th ed., McGraw-Hill, New York 1973, pp. 8-57.

[0171] For further details on the formulation of pesticides see, for example, GC Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0172] The agrochemical preparations, preferably herbicidal or plant growth regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferably 2 to 80% by weight, of active ingredients of the general formula (I) and salts thereof.

[0173] In wettable powders, for example, the active ingredient concentration is about 10 to 90 wt.%, the remainder to 100 wt.% consists of conventional formulation components. In emulsifiable concentrates, the active ingredient concentration can be about 1 to 90, preferably 5 to 80 wt.% Dust-like formulations contain 1 to 30 wt.% active ingredient, preferably 5 to 20 wt.% active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt.% active ingredient. In water-dispersible granules, the active ingredient content depends partly on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used. In water-dispersible granules, the active ingredient content is, for example, between 1 and 95 wt.%, preferably between 10 and 80 wt.%.

[0174] In addition, the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, dyes, defoamers, evaporation inhibitors, and pH and viscosity adjusters. Examples of formulation aids are described, among others, in "Chemistry and Technology of Agrochemical Formulations," ed. DA Knowles, Kluwer Academic Publishers (1998).

[0175] The compounds of general formula (I) according to the invention or their salts can be used as such or in the form of their preparations (formulations) in combination with other pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and / or growth regulators, e.g., as a ready-to-use formulation or as tank mixes. The combination formulations can be prepared based on the above-mentioned formulations, taking into account the physical properties and stability of the active ingredients to be combined.

[0176] As combination partners for the compounds of general formula (I) according to the invention in mixture formulations or in tank mixes, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the reference cited therein.

[0177] Of particular interest is the selective control of weeds in crops of useful and ornamental plants. Although the compounds of the general formula (I) according to the invention already exhibit very good to sufficient selectivity in many crops, phytotoxicity can in principle occur in some crops, and especially in the case of mixtures with other herbicides that are less selective. In this regard, combinations of compounds of the general formula (I) according to the invention that comprise the compounds of the general formula (I) or combinations thereof with other herbicides or pesticides and safeners are of particular interest. The safeners, which are used in an antidote-effective concentration, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g.in economically important crops such as cereals (wheat, barley, rye, maize, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.

[0178] The weight ratios of herbicide (mixture) to safener generally depend on the application rate of herbicide and the efficacy of the respective safener and can vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. The safeners can be formulated analogously to the compounds of general formula (I) or mixtures thereof with other herbicides / pesticides and can be provided and applied as a ready-to-use formulation or tank mix with the herbicides.

[0179] For application, the herbicide or herbicide-safener formulations in commercial form are diluted in the usual way, e.g., with water in the case of wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Dust-like preparations, soil or broadcast granules, and sprayable solutions are not usually diluted with other inert substances before use.

[0180] External conditions such as temperature, humidity, etc. influence to a certain extent the application rate of the compounds of the general formula (I) and / or their salts. The application rate can vary within wide limits. For use as a herbicide for controlling weeds, the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg / ha, more preferably in the range from 0.005 to 5 kg / ha, more preferably in the range from 0.01 to 1.5 kg / ha, especially preferably in the range from 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence application.

[0181] When using compounds of the general formula (I) according to the invention and / or salts thereof as plant growth regulators, for example as stalk shorteners in crop plants as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or maize, the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / ha. This applies both to pre-emergence and post-emergence application.

[0182] Application as a stem shortener can occur at various stages of plant growth. For example, application after tillering, at the beginning of longitudinal growth, is preferred. Alternatively, application as a plant growth regulator can also be applied to the seeds, which includes various seed dressing and coating techniques. The application rate depends on the individual technique and can be determined in preliminary trials.

[0183] As combination partners for the compounds of the general formula (I) according to the invention in agents according to the invention (e.g. mixture formulations or in the tank mix), known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and literature cited therein.The following are examples of known herbicides or plant growth regulators that can be combined with the compounds of the invention. These active ingredients are designated either by their common name in the English version according to the International Organization for Standardization (ISO) or by their chemical name or code number. This always includes all application forms, such as acids, salts, esters, as well as all isomeric forms such as stereoisomers and optical isomers, even if these are not explicitly mentioned.

[0184] Examples of such herbicidal mixture partners are:

[0185] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim- sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor- potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate und -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac- sodium, chlorfenprop,chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, - dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, - potassium, -triisopropanolammonium und -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium und -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3- one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl,diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr- sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2- Chlor-4-fluor-5 - [ 4 - ( 3 -fluorpropyl) -4,5 -dihydro-5 -oxo- 1 H-tetrazol- 1 -yl] -phenyl] -ethansulfonamid, F- 7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-lH-benzimidazol-4-yl]-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P- ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M- methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium,flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac -pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, - dimethylammonium und -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, fhipyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium und -trimesium, H-9201, i.e. O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl- isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron- methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02,i.e. l-(Dimethoxyphosphoryl)-ethyl-(2,4- dichlorphenoxy)acetat, imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin- ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium und sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(Difluormethyl)-l- methyl-3-(trifluormethyl)-lH-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-l,2-oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, - isopropylammonium, -potassium und -sodium, MCPB, MCPB -methyl, -ethyl und -sodium, mecoprop, mecoprop-sodium, und -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl und -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron,metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chlor-4-(l-methylethyl)- phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-l-methyl- 5-benzyloxypyrazol, neburon, nicosulfuron, nonanoic acid (Pelargonsäure), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham,propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron- ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz -propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, , SYN-523, SYP-249, i.e. l-Ethoxy-3-methyl-l-oxobut-3-en-2-yl- 5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e. l-[7-Fluor-3-oxo-4-(prop-2-in-l- yl)-3,4-dihydro-2H-l,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (Trifluoressigsäure), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone- methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-Dichlor-N-{2- [(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen:, Examples of plant growth regulators as possible mixing partners are: Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-l-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, Jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1 -methylcyclopropene, 2-(l-naphthyl)acetamide, 1 -naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol,trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.,

[0186] The following safeners, for example, are also suitable as combination partners for the compounds of general formula (I) according to the invention:

[0187] Sl) Compounds from the group of heterocyclic carboxylic acid derivatives:

[0188] Sl a ) Compounds of the type dichlorophenylpyrazolin-3-carboxylic acid (Sl a ), preferably compounds such as l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid ethyl ester (S 1 - 1) ("Mefenpyr-diethyl"), and related compounds as described in WO-A-91 / 07874;

[0189] Sl b ) Derivatives of dichlorophenylpyrazolecarboxylic acid (Sl b), preferably compounds such as ethyl l-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (Sl-2), ethyl l-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (Sl-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (Sl-4) and related compounds as described in EP-A-333131 and EP-A-269806;

[0190] Sl c ) Derivatives of l,5-diphenylpyrazole-3-carboxylic acid (Sl c ), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S 1 -5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S 1 -6) and related compounds as described, for example, in EP-A-268554;

[0191] Sl d ) Compounds of the triazolecarboxylic acid type (Sl d), preferably compounds such as fenchlorazole(ethyl ester), ie l-(2,4-dichlorophenyl)-5-trichloromethyl-(lH)-l,2,4-triazole-3-carboxylic acid ethyl ester (Sl-7), and related compounds as described in EP-A-174562 and EP-A-346620;

[0192] Sl e ) Compounds of the type 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (SI-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (SI-9) and related compounds as described in WO-A-91 / 08202, or ethyl 5,5-diphenyl-2-isoxazolinecarboxylic acid (SI-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (SI-11) ("Isoxadifen-ethyl") or -n-propyl ester (SI-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (SI-13), as described in patent application WO-A-95 / 07897.

[0193] 52) Compounds from the group of 8-quinolinoxy derivatives (S2):

[0194] S2 a ) Compounds of the 8-quinolinoxyacetic acid type (S2 a), preferably (5-chloro-8-quinolinoxy)acetic acid (l-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy)acetic acid (l,3-dimethyl-but-l-yl) ester (S2-2), (5-chloro-8-quinolinoxy)acetic acid 4-allyl-oxy-butyl ester (S2-3), (5-chloro-8-quinolinoxy)acetic acid l-allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinolinoxy)acetate ethyl ester (S2-5), (5-chloro-8-quinolinoxy)acetate methyl ester (S2-6), (5-chloro-8-quinolinoxy)acetate allyl ester (S2-7), (5-chloro-8-quinolinoxy)acetic acid 2-(2-propylidene-iminoxy)-1-ethyl ester (S2-8), (5-chloro-8-quinolinoxy)acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366, and (5-chloro-8-quinolinoxy)acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts as described in WO-A-2002 / 34048;

[0195] S2 b ) Compounds of the type (5-chloro-8-quinolinoxy)malonic acid (S2 b ), preferably compounds such as (5-chloro-8-quinolinoxy)malonic acid diethyl ester, (5-chloro-8-quinolinoxy)malonic acid diallyl ester, (5-chloro-8-quinolinoxy)malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198.

[0196] 53) Active substances of the dichloroacetamide (S3) type, which are often used as pre-emergence safeners (soil-acting safeners), such as

[0197] "Dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), "R-28725" (3-dichloroacetyl-2, 2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(l,3-dioxolan-2-yl)-methyl]-dichloroacetamide) from PPG Industries (S3-5), "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]-dichloroacetamide) from Sagro-Chem (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-l-oxa-3-aza-spiro[4,5]decane) from Nitrokemia or Monsanto (S3-7),

[0198] "TI-35" (1-Dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), "Diclonon" (Dicyclonone) or "BAS145138" or "LAB145138" (S3-9) ((RS)-l-Dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[l,2-a]pyrimidin-6-one) from BASF, "Furilazol" or "MON 13900" ((RS)-3-Dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), as well as its (R)-isomer (S3-11).

[0199] S4) Compounds from the class of acylsulfonamides (S4):

[0200] S4 a ) N-acylsulfonamides of the formula (S4 a ) and their salts as described in WO-A-97 / 45016, wherein

[0201] RA 1 (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, where the last two radicals are substituted by VA substituents from the group halogen, (Ci-C4)-alkoxy, (Ci-Ce)-haloalkoxy and (Ci-C4)-alkylthio and in the case of cyclic radicals also by (Ci-C4)-alkyl and (C1-C4)-haloalkyl;

[0202] RA 2 Halogen, (C1-C4)-alkyl, (Ci-C4)-alkoxy, CF3; mA 1 or 2;

[0203] VA is 0, 1, 2 or 3;

[0204] S4 b ) Compounds of the type 4-(benzoylsulfamoyl)benzamides of the formula (S4 b ) and their salts as described in WO-A-99 / 16744, wherein

[0205] RB 1 , RB 2independently hydrogen, (Ci-C6)-alkyl, (C3-Ce)-cycloalkyl, (Cs-Ce)-alkenyl, (C3-C6)-alkynyl,

[0206] RB 3 halogen, (C1-C4)-alkyl, (Ci-C4)-haloalkyl or (C1-C4)-alkoxy and ms is 1 or 2, for example those in which

[0207] RB 1 = Cyclopropyl, RB 2 = hydrogen and (RB 3 ) = 2-OMe ("Cyprosulfamide", S4-1),

[0208] RB 1 = Cyclopropyl, RB 2 = hydrogen and (RB 3 ) = 5-Cl-2-OMe is (S4-2), RB 1 = Ethyl, RB 2 = hydrogen and (RB 3 ) = 2-OMe is (S4-3),

[0209] RB 1 = Isopropyl, RB 2 = hydrogen and (RB 3 ) = 5-Cl-2-OMe is (S4-4) and

[0210] RB 1 = Isopropyl, RB 2 = hydrogen and (RB 3 ) = 2-OMe is (S4-5);

[0211] S4 C) Compounds from the class of benzoylsulfamoylphenylureas of the formula (S4 C ) as described in EP-A-365484, wherein

[0212] Rc 1 , Rc 2 independently of one another hydrogen, (Ci-Cs)-alkyl, (C3-Cs)-cycloalkyl, (C3-Ce)-alkenyl, (C3-C6)alkynyl,

[0213] Rc 3 halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF3 and me is 1 or 2; for example l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,

[0214] 1 - [4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3, 3-dimethylurea, l-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea;

[0215] S4 d ) Compounds of the N-phenylsulfonylterephthalamide type of formula (S4 d ) and their salts, which are known for example from CN 101838227, wherein

[0216] RD 4 Halogen, (C1-C4)-alkyl, (Ci-C4)-alkoxy, CF 3; mo 1 or 2;

[0217] RD 5 Hydrogen, (Ci-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl,

[0218] (C5-Ce)-cycloalkenyl.

[0219] S5) Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g.

[0220] 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-

[0221] Dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001. S6) Active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g.

[0222] 1-Methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-Methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-Aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, l-(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-l,2-dihydroquinoxalin-2-one, as described in WO-A-2005 / 112630.

[0223] 57) Compounds from the class of diphenylmethoxyacetic acid derivatives (S7), e.g.

[0224] Diphenylmethoxyacetic acid methyl ester (CAS Reg. No. 41858-19-9) (S7-1), diphenylmethoxyacetic acid ethyl ester or diphenylmethoxyacetic acid as described in WO-A-98 / 38856.

[0225] 58) Compounds of formula (S8) as described in WO-A-98 / 27049, where the symbols and indices have the following meanings:

[0226] RD 1 is halogen, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy,

[0227] RD 2is hydrogen or (C1-C4)-alkyl,

[0228] RD 3 is hydrogen, (Ci-Cs)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy; or their salts, no is an integer from 0 to 2.

[0229] S9) Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), e.g. l,2-dihydro-4-hydroxy-l-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 219479-18-2), l,2-dihydro-4-hydroxy-l-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999 / 000020.

[0230] S10) Compounds of the formulas (S10 a ) or (S10 b ), as described in WO-A-2007 / 023719 and WO-A-2007 / 023764,

[0231] RE 1Halogen, (Ci-C j-Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3

[0232] YE, ZE independently of each other O or S, IIE an integer from 0 to 4,

[0233] RE 2 (Ci-Cie)-alkyl, (C2-Ce)-alkenyl, (C3-Ce)-cycloalkyl, aryl; Benzyl, halobenzyl, RE 3 hydrogen or (Ci-Ce)-alkyl.

[0234] 511) Active substances of the oxyimino compound type (Sil), which are known as seed dressings, such as

[0235] "Oxabetrinil" ((Z)-l,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (Sl l-1), which is known as a seed dressing safener for millet against metolachlor damage,

[0236] "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (Sl l-2), known as a seed dressing safener for millet against metolachlor damage, and "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (Sl l-3), known as a seed dressing safener for millet against metolachlor damage.

[0237] 512) Active ingredients from the class of isothiochromanones (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998 / 13361.

[0238] 513) One or more compounds from group (S13):

[0239] "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides,

[0240] "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice,

[0241] "Flurazole" (benzyl 2-chloro-4-trifluoromethyl-l,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for millet against damage from alachlor and metolachlor, "CF 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-l-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage from imidazolinones, "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-l,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn, "MG 838" (CAS Reg. No. 133993-74-5)

[0242] (2-propenyl l-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia "Disulfoton" (O,O-diethyl S-2-ethylthioethyl phosphorus dithioate) (S13-7), "Dietholate" (O,O-diethyl-O-phenylphosphorothioate) (S13-8), "Mephenate" (4-Chlorophenyl methyl carbamate) (S13-9).

[0243] 514) Active substances which, in addition to a herbicidal effect against harmful plants, also have a safener effect on crops such as rice, such as

[0244] "Dimepiperate" or "MY-93" GS'- 1 -methyl- 1-phenylethyl-piperidine-l-carbothioate), which is known as a safener for rice against damage from the herbicide Molinate,

[0245] "Daimuron" or "SK 23" (l-(l-methyl-l-phenylethyl)-3-p-tolylurea), known as a safener for rice against damage from the herbicide imazosulfuron, "Cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-l-(l-methyl-l-phenylethyl)urea, see JP-A-60087270), known as a safener for rice against damage from some herbicides, "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), known as a safener for rice against damage from some herbicides,

[0246] "CSB" (l-bromo-4-(chloromethylsulfonyl) benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage from some herbicides in rice.

[0247] S15) Compounds of formula (S15) or their tautomers, as described in WO-A-2008 / 131861 and WO-A-2008 / 131860, wherein

[0248] RH 1 a (Ci-C6)-haloalkyl radical and RH 2 hydrogen or halogen and RH 3 , RH 4independently of one another hydrogen, (Ci-Ci8)-alkyl, (C2-Ci8)-alkenyl or (C2-Ci6)-alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (Ci-Ci8)-alkoxy, (Ci-Ci8)-haloalkoxy, (Ci-Ci8)-alkylthio, (Ci-Ci8)-alkylamino, di[(Ci-Ci4)-alkyl]amino, [(Ci-Ci4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, (Cs-Ce8)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, or (Cs-Cej-cycloalkyl, (Cr-Cej-cycloalkenyl, (Cs-Cej-cycloalkyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (Cr-Gj-cycloalkenyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring,where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (Ci-Crj-alkyl, (Ci-Ct-haloalkyl, (C1-C4)-alkoxy, (Ci-Ct-haloalkoxy, (Ci-CO-alkylthio, (Ci-C^-alkylamino, di[(Ci-C4)alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(Ci-Ct-haloalkoxy]carbonyl, (Cs-Cej-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, or,

[0249] RH 3 (Ci-C -alkoxy, (C2-C4)-alkenyloxy, (C2-Ce)-alkynyloxy or (C2-C4)-haloalkoxy and RH 4 hydrogen or (C1-C4)-alkyl or

[0250] RH 3 and RH 4together with the directly bonded N atom forms a four- to eight-membered heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy and (Ci-C4)-alkylthio.

[0251] S16) Active substances that are primarily used as herbicides but also have a safener effect on crops, e.g.

[0252] (2,4-Dichlorophenoxy)acetic acid (2,4-D), (4-Chlorophenoxy)acetic acid, (R,S)-2-(4-Chloro-o-tolyloxy)propionic acid (Mecoprop), 4-(2,4-Dichlorophenoxy)butyric acid (2,4-DB), (4-Chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-Chloro-o-tolyloxy)butyric acid, 4-(4-Chlorophenoxy)butyric acid, 3,6-Dichloro-2-methoxybenzoic acid (Dicamba), l-(Ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (Lactidichloro-ethyl).

[0253] Preferred safeners in combination with the compounds of the general formula (I) according to the invention and / or their salts, in particular with the compounds of the formulas (1-1) to (1-209) or (2-1) to (2-14) and / or their salts, are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen ethyl, mefenpyr diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen ethyl and mefenpyr diethyl.

[0254] Biological examples

[0255] In the following examples and tables the following abbreviations are used: Unwanted plants / Weeds ABUTH: Abutilon theophrasti

[0256] AFOMY: Alopecurus myosuroides

[0257] AM ARE: Amaranthus retroflexus

[0258] DIGSA: Digitaria sanguinalis

[0259] ECHCG: Echinochloa crus-galli

[0260] KCHSC: Kochia scoparia

[0261] LOLRI: Lolium rigidum

[0262] MATIN: Matricaria inodora POAAN: Poa annua

[0263] SET VI: Setaria viridis

[0264] STEME: Stellaria media

[0265] VERPE: Veronica persica

[0266] VIOTR: Viola tricolor

[0267] A. Post-emergence herbicidal activity at 1280 g / ha

[0268] Seeds of monocotyledonous and dicotyledonous weeds were sown in plastic pots in sandy loam soil (double sowings with one species of monocotyledonous and dicotyledonous weed per pot), covered with soil, and grown in a greenhouse under controlled growth conditions. Two to three weeks after sowing, the test plants were treated at the single-leaf stage. The compounds of the invention, formulated as wettable powders (WP) or emulsion concentrates (EC), were applied to the green plant parts as an aqueous suspension or emulsion, with the addition of 0.5% additive, at a water application rate equivalent to 600 liters per hectare. After the test plants had been in the greenhouse for approximately three weeks under optimal growth conditions, the effect of the preparations was visually assessed in comparison to untreated controls.

[0269] For example, 100% effect means plants are dead, 0% effect means like control plants.

[0270] The following Tables A1 to A12 show the effects of selected compounds of general formula (I) according to Table 1 on various weeds and an application rate corresponding to 1280 g / ha, which were obtained according to the test procedure mentioned above.

[0271] Table Al: Post-emergence effect at 1280g / ha against ABUTH in % Table A2: Post-emergence effect at 1280g / ha against ALOMY in %

[0272] Table A3: Post-emergence effect at 1280g / ha against AMARE in %

[0273] Table A4: Post-emergence effect at 1280g / ha against DIGSA in %

[0274] Table A5: Post-emergence effect at 1280g / ha against ECHCG in %

[0275] Table A6: Post-emergence effect at 1280g / ha against KCHSC in % Table A7: Post-emergence effect at 1280g / ha against LOLRI in %

[0276] Table A8: Post-emergence effect at 1280g / ha against MATIN in %

[0277] Table A9: Post-emergence effect at 1280g / ha against POAAN in %

[0278] Table A10: Post-emergence effect at 1280g / ha against SETVI in %

[0279] Table Al l: Post-emergence effect at 1280g / ha against STEME in %

[0280] Table A12: Post-emergence effect at 1280g / ha against VERPE in % The test results demonstrate that compounds of the general formula (I) according to the invention, when applied post-emergence, have good herbicidal activity against selected weeds such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Lolium rigidum, Matricaria inodora, Poa annua, Setaria viridis, Stellaria media and Veronica persica at a respective application rate of 1280 g of active substance per hectare.

[0281] B. Post-emergence herbicidal effect at 80 g / ha

[0282] Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants were sown in plastic or organic plant pots in sandy loam soil, covered with soil, and grown in a greenhouse under controlled growth conditions. Two to three weeks after sowing, the test plants were treated at the single-leaf stage. The compounds of the invention, formulated as wettable powders (WP) or emulsion concentrates (EC), were then sprayed onto the green plant parts as an aqueous suspension or emulsion with the addition of 0.5% additive at a water application rate equivalent to 600 l / ha. After the test plants had been in the greenhouse for approximately three weeks under optimal growth conditions, the effect of the preparations was visually assessed in comparison to untreated controls. For example, 100% effect means plants have died, 0% effect means the same as the control plants.

[0283] The following Tables B1 to B10 show the effects of selected compounds of general formula (I) according to Table 1 on various weeds and an application rate corresponding to 80 g / ha, which were obtained according to the above-mentioned test procedure.

[0284] Table Bl: Post-emergence effect at 80g / ha against ABUTH in %

[0285] Table B2: Post-emergence effect at 80g / ha against ALOMY in % Table B3: Post-emergence effect at 80g / ha against AMARE in %

[0286] Table B4: Post-emergence effect at 80g / ha against DIGSA in % Table B5: Post-emergence effect at 80g / ha against ECHCG in %

[0287] Table B6: Post-emergence effect at 80g / ha against KCHSC in %

[0288] Table B7: Post-emergence effect at 80g / ha against POLCO in %

[0289] Table B8: Post-emergence effect at 80g / ha against SETVI in %

[0290] Table B9: Post-emergence effect at 80g / ha against VERPE in %

[0291] Table BIO: Post-emergence effect at 80g / ha against VIOTR in %

[0292] The test results demonstrate that compounds of the general formula (I) according to the invention, when applied post-emergence, have good herbicidal activity against selected weeds such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Polygonum convolvulus, Setaria viridis, Veronica persica and Viola tricolor at a respective application rate of 80 g of active substance per hectare.

[0293] C. Herbicidal activity in pre-emergence at 1280 g / ha

[0294] Seeds of monocotyledonous and dicotyledonous weeds were sown in plastic pots in sandy loam soil (double sowings with one species of monocotyledonous or dicotyledonous weed per pot) and covered with soil. The compounds of the invention, formulated as wettable powders (WP) or emulsion concentrates (EC), were then applied to the surface of the covering soil as an aqueous suspension or emulsion, with the addition of 0.5% additive, at a water application rate equivalent to 600 liters per hectare. After treatment, the pots were placed in a greenhouse and maintained under favorable growth conditions for the test plants. After approximately 3 weeks, the effectiveness of the preparations was visually assessed in percentages compared to untreated controls.

[0295] For example, 100% effect means plants are dead, 0% effect means like control plants.

[0296] Tables C1 to C12 below show the effects of selected compounds of general formula (I) according to Table 1 on various weeds and an application rate corresponding to 1280 g / ha, obtained according to the aforementioned test procedure. Table C1: Pre-emergence effect at 1280 g / ha against ABUTH in %

[0297] Table C2: Pre-emergence effect at 1280g / ha against ALOMY in %

[0298] Table C3: Pre-emergence effect at 1280g / ha against AMARE in %

[0299] Table C4: Pre-emergence effect at 1280g / ha against DIGSA in %

[0300] Table C5: Pre-emergence efficacy at 1280g / ha against ECHCG in % Table C6: Pre-emergence effect at 1280g / ha against KCHSC in %

[0301] Table C7: Pre-emergence efficacy at 1280g / ha against LOLRI in %

[0302] Table C8: Pre-emergence effect at 1280g / ha against MATIN in % Table C9: Pre-emergence effect at 1280g / ha against POAAN in %

[0303] Table CIO: Pre-emergence effect at 1280g / ha against SETVI in %

[0304] Table Cl l: Pre-emergence effect at 1280g / ha against STEME in % Table C12: Pre-emergence effect at 1280g / ha against VERPE in % The test results demonstrate that compounds of the general formula (I) according to the invention, when applied pre-emergence, have good herbicidal activity against selected weeds such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Lolium rigidum, Matricaria inodora, Poa annua, Setaria viridis, Stellaria media and Veronica persica at a respective application rate of 1280 g of active substance per hectare.

[0305] D. Herbicidal activity in pre-emergence at 80 g / ha

[0306] Seeds of monocotyledonous and dicotyledonous weeds and cultivated plants were sown in plastic or organic plant pots and covered with soil. The compounds of the invention, formulated as wettable powders (WP) or as emulsion concentrates (EC), were then applied to the surface of the covering soil as an aqueous suspension or emulsion with the addition of 0.5% additive at a water application rate equivalent to 600 l / ha. After treatment, the pots were placed in the greenhouse and maintained under favorable growth conditions for the test plants. After approximately 3 weeks, the effectiveness of the preparations was visually assessed in percentages compared to untreated controls. For example, 100% effectiveness = plants have died, 0% effectiveness = same as control plants.

[0307] The following Tables D1 to D12 show the effects of selected compounds of general formula (I) according to Table 1 on various weeds and an application rate corresponding to 80 g / ha, which were obtained according to the above-mentioned test procedure.

[0308] Table Dl: Pre-emergence effect at 80g / ha against ABUTH in % Table D2: Pre-emergence effect at 80g / ha against ALOMY in %

[0309] Table D3: Pre-emergence effect at 80g / ha against AMARE in % Table D4: Pre-emergence effect at 80g / ha against DIGSA in %

[0310] Table D5: Pre-emergence efficacy at 80g / ha against ECHCG in %

[0311] Table D6: Pre-emergence effect at 80g / ha against KCHSC in %

[0312] Table D7: Pre-emergence effect at 80g / ha against LOLRI in % Table D8: Pre-emergence effect at 80g / ha against MATIN in %

[0313] Table D9: Pre-emergence effect at 80g / ha against POLCO in %

[0314] Table DIO: Pre-emergence effect at 80g / ha against SETVI in % Table Dl l: Pre-emergence effect at 80g / ha against VERPE in % Table D12: Pre-emergence effect at 80g / ha against VIOTR in %

[0315] The test results demonstrate that compounds of general formula (I) according to the invention, when applied pre-emergence, have good herbicidal activity against selected weeds such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Lolium rigidum, Matricaria inodora, Polygonum convolvulus, Setaria viridis, Veronica persica and Viola tricolor at a respective application rate of 80 g of active substance per hectare.

Claims

Patent claims 1. Substituted 2-C azines of general formula (I) or their salts A for nitrogen or CR 1 stands, R 1 stands for hydrogen, CN or halogen, B for CH, CR 2 or N stands Q stands for Υ-(C2-Ce)-haloalkyl, where Y is direct bond, oxygen, S(O) n , CO or OSO2 means, or Q stands for Z-aryl or Z-heteroaryl, where aryl has 1 to 5 substituents, independently selected from group R 4 , is substituted, wherein heteroaryl with up to 2 substituents, independently selected from group R 4 , is substituted, and where Z is direct bond, O, S(O) n or CH2 means R 2 independently for halogen, cyano, nitro, amino, (Ci-C4)-alkyl, (C1-C4)-haloalkyl, cyclopropyl, (Ci-CO-alkoxy, (Ci-CO-haloalkoxy or (Ci-C4)-alkyl-S(O) n- stands, m is equal to 0, 1, 2 or 3, n is equal to 0, 1 or 2, R 3 for hydrogen, halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-CO-haloalkyl, (C1-C4)-alkoxy, (Ci-C2)-haloalkoxy or (Ci-C4)-alkyl-S (O) n - stands, provided that, if A for CR 1 stands, R 3 It must not be hydrogen. R 4 for halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-Cs)-haloalkyl, (C1-C4)-alkoxy, (C1-C2)- Haloalkoxy, (C1-C4)-alkoxymethyl or (Ci-C4)-alkyl-S(O) n - stands, and R 5 for hydrogen or CN. Compound of general formula (I) according to claim 1 or its salts, wherein A for nitrogen or CR 1 stands, R 1 stands for hydrogen, CN or halogen, B for CH, CR 2 or N stands Q stands for Y-(C3-Cs)-haloalkyl, where Y is direct bond, oxygen, S(O) n, CO or OSO2 means, or Q stands for Z-aryl or Z-heteroaryl, where aryl has 1 to 3 substituents, independently selected from group R 4 , is substituted, wherein heteroaryl with up to 2 substituents, independently selected from group R 4 , is substituted, and where Z is direct bond, O, S(O) n or CH2 means R 2 independently for halogen, cyano, nitro, amino, (Ci-C4)-alkyl, (C1-C4)-haloalkyl, cyclopropyl, (Ci-CO-alkoxy, (Ci-CO-haloalkoxy or (Ci-C4)-alkyl-S(O) n - stands, m is equal to 0, 1, 2 or 3, n is equal to 0, 1 or 2, R 3 for hydrogen, halogen, cyano, (C1-C4)-alkyl, (Ci-CO-haloalkyl, (C1-C4)-alkoxy or (Ci-C2)-haloalkoxy, provided that if A is for CR 1 stands, R 3 It must not be hydrogen. R 4stands for halogen, cyano, (C1-C4)-alkyl, (Ci-Cs)-haloalkyl or (C1-C4)-alkoxymethyl, and R 5 for hydrogen or CN. Compound of general formula (I) according to claim 1 or its salts, wherein A for nitrogen or CR 1 stands, R 1 stands for hydrogen, cyano, fluorine or chlorine, B for CH, CR 2 or N stands Q stands for Y-(C3-Cs)-haloalkyl, where Y means direct bond, oxygen, S, CO or OSO2, or Q stands for Z-aryl or Z-heteroaryl, where aryl has 1 or 2 substituents, independently selected from group R. 4 , is substituted, wherein heteroaryl with up to 2 substituents, independently selected from group R 4 , is substituted, and where Z means direct bond, O, S or CH2, R 2independently of each other, m stands for fluorine, chlorine, bromine, cyano, methyl, CF3 or methoxy, where m is equal to 0, 1 or 2. R 3 for hydrogen, chlorine, bromine, fluorine, cyano, methyl, CF3, methoxy or CHF2O, provided that if A is for CR 1 stands, R 3 It must not be hydrogen. R 4 stands for fluorine, chlorine, methyl, CHF2, CF3, methoxymethyl, and R 5 stands for hydrogen or CN. Compound of general formula (I) according to claim 1 or salts thereof, wherein A for nitrogen or CR 1 stands, R 1 stands for hydrogen, cyano, fluorine or chlorine, B for CH, CR 2 or N stands Q stands for Y-(C3-Cs)-haloalkyl, where Y means direct bond, oxygen, S, CO or OSO2, or Q stands for Z-aryl or Z-heteroaryl, where aryl has 1 or 2 substituents, independently selected from group R.4 , is substituted, wherein heteroaryl with up to 2 substituents, independently selected from group R 4 , is substituted, and where Z means direct bond, O, S or CH2, R 2 independently of each other, m stands for fluorine, chlorine, bromine, cyano, methyl, CF3 or methoxy, where m is equal to 0, 1 or 2. R 3 for hydrogen, chlorine, bromine, fluorine, cyano, methyl, CF3, methoxy or CHF2O, provided that if A is for CR 1 stands, R 3 It must not be hydrogen. R 4 stands for fluorine, chlorine, methyl, CHF2, CF3 or methoxymethyl, and R 5 stands for hydrogen or CN. Compound of general formula (I) according to claim 1 or salts thereof, wherein A stands for nitrogen, CH, CCN or CF, B stands for CH, Q für (CH2)3CF3, (CH2)4CF3, S(CH2)3CF3, S(CH2)3C1 , SO(CH2)3C1 , SO(CH2)2CF3, SO(CH2)3CF3, SO2(CH2)3CF3, O(CH2)3CF3, C(O)(CH2)3CF3, OSO2(CH2)3CF3, OSO2(CH2)2CF3, OSO2(CH2)3C1 , 4-Fluorbenzyl, 4-Chlorphenyl, 3,4-Difluorphenyl, 4- Fluorphenoxy, 4-Fluorphenylsulfanyl, 2,4-Cl2-phenylsulfonyl, 2,4-Cl2-phenylsulfanyl, 2.4-Cl2-phenylsulfinyl, 4-(CF3)-pyrazol-l-yl, 5-Cl-pyrimidin-2-oxy, 5-F-pyrimidin-2- oxy, 5-Cl-3-F-pyridin-2-oxy, 3-(CHF2)-isoxazol-5-yl, 5-(CHF2)-isoxazol-3-yl, 1,2,4- oxadiazol-3-yl, 5-Methyl-l,2,4-oxadiazol-3-yl, 5-(CHF2)-l,2,4-oxadiazol-3-yl, 5-(CF3)- 1.2.4-oxadiazol-3-yl, 5-F-pyrimidin-2-yl-sulfanyl, 5-Cl-pyrimidin-2-yl-sulfanyl, 5-C1- pyrimidin-2-yl-sulfinyl, 5-Cl-pyrimidin-2-yl-sulfonyl, 4-Cl-pyrazol-l-ylmethyl, 4-Br- pyrazol-l-ylmethyl oder 4-(CF3)-pyrazol-l-ylmethyl steht, R 2 unabhängig voneinander für Fluor, Chlor, Brom, Cyano, Methyl, CF3oder Methoxy steht, m ist gleich 0, 1 oder 2, R 3stands for chlorine, bromine or fluorine and R 5 for hydrogen or CN. Herbicidal compositions characterized by a herbicidally active content of at least one compound of general formula (I) according to any one of claims 1 to 5. Herbicidal compositions according to claim 6 in a mixture with formulation aids. Herbicidal compositions according to claim 6 or 7 containing at least one further pesticidal active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators. Herbicide compositions according to claim 8, comprising a safener. Herbicide compositions according to claim 9, comprising cyprosulfamide, cloquintocet-mexyl, mefenpyrdiethyl, or isoxadifen-ethyl. Herbicide compositions according to any one of claims 6 to 10, comprising a further herbicide. A method for controlling unwanted plants, characterized in that an effective amount of at least one compound of general formula (I) according to any one of claims 1 to 5 or of a herbicidal composition according to any one of claims 6 to 10 is applied to the plants or to the site of unwanted plant growth. Use of compounds of general formula (I) according to any one of claims 1 to 5 or of herbicidal compositions according to any one of claims 6 to 10 for controlling unwanted plants. Use according to claim 13, characterized in that the compounds of general formula (I) are used for controlling unwanted plants in crops of cultivated plants.Use according to claim 14, characterized in that the crop plants are transgenic crop plants.

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