Substituted 2-C-azines and their salts, and their use as herbicidal active substances

Abstract

Substituted 2-C-azines of general formula (I) and their use as herbicides, in particular as plant growth regulators for controlling weeds and / or grass weeds in crops of useful plants and / or for influencing the growth of crops of useful plants are described. The invention also relates to herbicides and / or plant growth regulators comprising one or more compounds of general formula (I). [Formula 1] TIFF2025510286000096.tif52142

Description

[Technical field]

[0001] explanation The present invention relates to the technical field of crop protection products, in particular to the technical field of herbicides for the selective control of broadleaf and grass weeds in crops of useful plants. In particular, the invention relates to substituted 2-C-azines and their salts, processes for their preparation, and their use as herbicides. [Background technology]

[0002] In their application, hitherto known crop protection products or active ingredients for controlling undesirable vegetation for selectively controlling harmful plants in crops of useful plants may have the drawbacks that (a) they have insufficient herbicidal activity, if any, against certain harmful plants, (b) the spectrum of harmful plants that can be controlled with the active ingredients is not wide enough, (c) their selectivity in crops of useful plants is too low, and / or (d) they have an unfavorable toxicological profile. Moreover, some active ingredients that can be used as plant growth regulators for some useful plants cause undesirable reductions in yields in other useful plants or are compatible with crop plants only within a narrow application range, if at all. Some of the known active ingredients cannot be produced economically on an industrial scale due to difficult-to-obtain precursors and reagents or have insufficient chemical stability. In the case of other active ingredients, their activity depends too much on environmental conditions such as weather and soil conditions.

[0003] The herbicidal action of these known compounds, especially at low application rates, and / or their compatibility with crop plants still requires improvement.

[0004] AU535637, EP8192, EP61913, JP61236766, WO2016 / 196606, WO2021 / 204706, GB2594931 and WO2016 / 010731 are some of the documents that describe heteroaryloxybenzenes that are said to have herbicidal activity. WO2020 / 002089 and WO2022 / 002838 describe heteroaryloxypyridines that are said to have herbicidal activity. WO2020 / 193474 describes 2-heteroarylaminobenzenes that are said to have herbicidal activity.

[0005] In contrast, substituted 2-C-azines or their salts have not yet been described as active herbicidal ingredients. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Australian Patent No. 535637 [Patent Document 2] European Patent No. 8192 [Patent Document 3] European Patent No. 61913 [Patent Document 4] Patent No. 61236766 [Patent Document 5] International Publication No. 2016 / 196606 [Patent Document 6] International Publication No. 2021 / 204706 [Patent Document 7] UK Patent No. 2594931 [Patent Document 8] International Publication No. 2016 / 010731 [Patent Document 9] International Publication No. 2020 / 002089 [Patent Document 10] International Publication No. 2022 / 002838 [Patent Document 11] International Publication No. 2020 / 193474 Summary of the Invention [Means for solving the problem]

[0007] Surprisingly, it has now been found that certain substituted 2-C-azines or salts thereof are particularly suitable as active herbicidal ingredients.

[0008] Thus, the present invention relates to a compound of general formula (I): [ka] [During the ceremony, A is nitrogen or CR 1 and R 1 is hydrogen, CN or halogen, B is CH, CR 2 or N, Q is Y-(C2-C6)-haloalkyl, where Y is a direct bond, oxygen, S(O) n , CO or OSO2, or Q is Z-aryl or Z-heteroaryl, where aryl is R 4 and heteroaryl is substituted by 1 to 5 substituents independently selected from the group consisting of R 4 and Z is a direct bond, O, S(O) n or CH2, R 2 are independently halogen, cyano, nitro, amino, (C1-C4)-alkyl, (C1-C4)-haloalkyl, cyclopropyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy or (C1-C4)-alkyl-S(O) n - and m is 0, 1, 2 or 3; n is 0, 1 or 2; R 3is hydrogen, halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C2)-haloalkoxy or (C1-C4)-alkyl-S(O) n - and However, A is CR 1 If R 3 must not be hydrogen, R 4 is halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy, (C1-C2)-haloalkoxy, (C1-C4)-alkoxymethyl, (C1-C4)-alkyl-S(O) n - and and R 5 is hydrogen or CN. or a salt thereof.

[0009] The compounds of general formula (I) can form salts by the addition of suitable inorganic or organic acids, such as mineral acids, for example HCl, HBr, H2SO4, H3PO4 or HNO3, or organic acids, such as carboxylic acids, for example formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, for example p-toluenesulfonic acid, to basic groups, for example amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts contain the conjugate base of the acid as the anion. Suitable substituents in deprotonated form, for example sulfonic acids, especially sulfonamides or carboxylic acids, can form inner salts with groups such as amino groups that are themselves protonatable. Salts can also be formed by the action of a base on the compounds of general formula (I). Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, as well as ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and hydrogen carbonates, in particular sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate. These salts are those in which the acidic hydrogen is present in a form which is an agriculturally suitable cation, such as metal salts, in particular alkali metal or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, such as salts of the formula [NR a R b R c R d ] + A cation of a ~R d are each independently replaced with an organic group, particularly alkyl, aryl, arylalkyl, or alkylaryl. Also useful are alkylsulfonium and alkylsulfoxonium salts, such as (C1-C4)-trialkylsulfonium and (C1-C4)-trialkylsulfoxonium salts.

[0010] The substituted 2-C-azines of the present invention of general formula (I) can exist in various tautomeric structures depending on external conditions such as pH, solvent and temperature, all of which are encompassed by general formula (I).

[0011] The compounds of formula (I) used according to the present invention, and their salts, are hereinafter referred to as "compounds of general formula (I)". DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] More preferably, the present invention relates to a compound represented by the general formula (I), A is nitrogen or CR 1 and R 1 is hydrogen, CN or halogen, B is CH, CR 2 or N, Q is Y-(C3-C5)-haloalkyl, where Y is a direct bond, oxygen, S(O) n , CO or OSO2, or Q is Z-aryl or Z-heteroaryl, where aryl is R 4 and heteroaryl is substituted by 1 to 3 substituents independently selected from the group consisting of R 4 and Z is a direct bond, O, S(O) n or CH2, R 2 are independently halogen, cyano, nitro, amino, (C1-C4)-alkyl, (C1-C4)-haloalkyl, cyclopropyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy or (C1-C4)-alkyl-S(O) n - and m is 0, 1, 2 or 3; n is 0, 1 or 2; R 3 is hydrogen, halogen, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy or (C1-C2)-haloalkoxy, However, A is CR 1 If R 3 must not be hydrogen, R 4is halogen, cyano, (C1-C4)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxymethyl, and R 5 is hydrogen or CN.

[0013] The present invention particularly preferably comprises a compound represented by the general formula (I), A is nitrogen or CR 1 and R 1 is hydrogen, cyano, fluorine or chlorine, B is CH, CR 2 or N, Q is Y-(C3-C5)-haloalkyl, where Y represents a direct bond, oxygen, S, CO or OSO2, or Q is Z-aryl or Z-heteroaryl, where aryl is R 4 and the heteroaryl is substituted by 1 or 2 substituents independently selected from the group 4 and Z represents a direct bond, O, S or CH2; R 2 are independently fluorine, chlorine, bromine, cyano, methyl, CF3 or methoxy; m is 0, 1 or 2; R 3 is hydrogen, chlorine, bromine, fluorine, cyano, methyl, CF3, methoxy or CHF2O, However, A is CR 1 If R 3 must not be hydrogen, R 4 is fluorine, chlorine, methyl, CHF2, CF3 or methoxymethyl, and R 5 is hydrogen or CN.

[0014] The present invention further preferably comprises a compound represented by the general formula (I): A is nitrogen or CR 1 and R 1 is hydrogen, cyano, fluorine or chlorine, B is CH, CR 2 or N, Q is Y-(C3-C5)-haloalkyl, where Y represents a direct bond, oxygen, S, CO or OSO2, or Q is Z-aryl or Z-heteroaryl, where aryl is R 4 and the heteroaryl is substituted by 1 or 2 substituents independently selected from the group 4 and Z represents a direct bond, O, S or CH2; R 2 are independently fluorine, chlorine, bromine, cyano, methyl, CF3 or methoxy; m is 0, 1 or 2; R 3 is hydrogen, chlorine, bromine, fluorine, cyano, methyl, CF3, methoxy or CHF2O, However, A is CR 1 If R 3 must not be hydrogen, R 4 is fluorine, chlorine, methyl, CHF2, CF3 or methoxymethyl, and R 5 is hydrogen or CN.

[0015] The present invention further preferably comprises a compound represented by the general formula (I): A is nitrogen, CH, CCN or CF; B is CH; Q is (CH2)3CF3, (CH2)4CF3, S(CH2)3CF3, S(CH2)3Cl, SO(CH2)3Cl, SO(CH2)2CF3, SO(CH2)3CF3, SO2(CH2)3CF3, O(CH2)3CF3, C(O)(CH2)3CF3, OSO2(CH2)2CF3, OSO2(CH2)3CF3, OSO2(CH2)3Cl, 4-fluorobenzyl, 4-chlorophenyl, 3,4-difluorophenyl, 4-fluorophenoxy, 5-Cl-pyrimidine-2-oxy, 5-F-pyrimidine-2-oxy, 5-Cl-3-F-pyridine-2-oxy, 4-fluorophenylsulfanyl, 2,4-Cl-phenylsulfonyl, 2,4-Cl-phenylsulfan ... sulphinyl, 3-(CHF2)-isoxazol-5-yl, 5-(CHF2)-isoxazol-3-yl, 1,2,4-oxadiazol-3-yl, 5-methyl-1,2,4-oxadiazol-3-yl, 5-(CHF2)-1,2,4-oxadiazol-3-yl, 5-(CF3)-1,2,4-oxadiazol-3-yl, 5-Cl-pyrimidin-2-ylsulfanyl, 5-Cl-pyrimidin-2-ylsulfinyl, 5-Cl-pyrimidin-2-ylsulfonyl, 5-F-pyrimidin-2-ylsulfanyl, 4-(CF3)-pyrazol-1-yl, 4-Cl-pyrazol-1-ylmethyl, 4-Br-pyrazol-1-ylmethyl or 4-(CF3)-pyrazol-1-ylmethyl, R 2 are independently fluorine, chlorine, bromine, cyano, methyl, CF3 or methoxy; m is 0, 1 or 2; R 3 is chlorine, bromine or fluorine, and R 5 is hydrogen or CN.

[0016] The present invention further preferably comprises a compound represented by the general formula (I): A is nitrogen, CH or CF; B is CH; Q is (CH2)3CF3, S(CH2)3CF3, SO(CH2)3CF3, O(CH2)3CF3, OSO2(CH2)3CF3, OSO2(CH2)3Cl, 4-fluorobenzyl, 3,4-difluorophenyl, 4-fluorophenoxy, 4-fluorophenylsulfanyl, 2,4-Cl2-phenylsulfanyl, 4-(CF3)-pyrazol-1-yl, 5-Cl-pyrimidin-2-oxy, 5-F-pyrimidin-2-oxy, 5-Cl-3-F-pyridin-2-oxy, 3-(CHF2)-isoxazol-5-yl or 5-methyl-1,2,4-oxadiazol-3-yl; R 2 are independently fluorine, chlorine, bromine, cyano, methyl, CF3 or methoxy; m is 0, 1 or 2; R 3 is chlorine, bromine or fluorine, and R 5 is hydrogen or CN.

[0017] The radical definitions listed above in general terms or within the preferred ranges apply both to the final products of general formula (I) and in each case to the starting materials or intermediates required for the preparation. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.

[0018] Of particular interest, primarily for reasons of higher herbicidal activity, better selectivity and / or better preparability, are the inventive compounds of the general formula (I) as described or salts thereof, or the inventive uses thereof, in which the individual radicals have one of the preferred meanings already specified or specified below, or in particular one or more of the preferred meanings already specified or specified below appear in combination.

[0019] The terms used above and below with respect to the compounds of the present invention are explained below. They are well known to those skilled in the art and have the definitions specifically explained below:

[0020] Unless otherwise defined, names of chemical groups generally indicate that the bond to the backbone or remainder of the molecule is via the last-mentioned structural element of the relevant chemical group, i.e., via an oxygen atom in the case of (C1-C4)-alkoxy, (C1-C4)-alkyl-S(O) n - is to be understood via the sulfur atom, and in the case of (C1-C4)-alkoxymethyl via the carbon atom of the methyl group.

[0021] The term "halogen" refers, for example, to a fluorine, chlorine, bromine or iodine atom. When this term is used in a radical, "halogen" refers, for example, to a fluorine, chlorine, bromine or iodine atom.

[0022] The expression "(C1-C4)-alkyl" as illustratively referred to herein is a shorthand notation for linear or branched alkyl radicals having 1 to 4 carbon atoms according to the stated ranges for carbon atoms, i.e. including methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radicals. General alkyl radicals having a wider specific range of carbon atoms, such as "(C2-C6)-alkyl", correspondingly also include linear or branched alkyl radicals having a higher number of carbon atoms, i.e. according to the present invention, alkyl radicals having 5 and 6 carbon atoms.

[0023] "Haloalkyl" refers to alkyl that is partially or fully substituted with same or different halogen atoms, for example, monohaloalkyl, for example, CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, CH2F, CH2CH2CF3; perhaloalkyl, for example, CCl3, CClF2, CFCl2, CF2CClF2, CF2CClFCF3; polyhaloalkyl, for example, CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3; the term perhaloalkyl also encompasses the term perfluoroalkyl.

[0024] "Alkoxy" refers to an alkyl radical attached through an oxygen atom, including but not limited to (C1-C4)-alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy.

[0025] Haloalkoxy is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2Cl.

[0026] The term "aryl" denotes an optionally substituted monocyclic, bicyclic or polycyclic aromatic system preferably having 6 to 14, especially 6 to 10, ring carbon atoms, such as phenyl, naphthyl, anthryl, phenanthrenyl, etc., preferably phenyl.

[0027] If a substructure is substituted by "one or more radicals" from a list (=group) of radicals or a generally defined group of radicals, this includes in each case simultaneous substitution by several identical and / or structurally different radicals.

[0028] According to the invention, the expression "heteroaryl" denotes heteroaromatic compounds, i.e. fully unsaturated aromatic heterocyclic compounds, preferably with 5-7 membered rings and with 1-4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N. Heteroaryls according to the invention are for example 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl, 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-triphenylphosphine, 1H-pyrazole ... Azol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1, 2,3-Oxadiazol-4-yl, 1,2,3-Oxadiazol-5-yl, 1,2,5-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, 1,3,5-Triazin-2-yl, 1,2,4-Triazin-3-yl, 1,2,4-Triazin-5-yl , 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and 1,2,4-diazepinyl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3,4-thiatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl. The heteroaryl group of the present invention may also be substituted by one or more identical or different radicals. When two adjacent carbon atoms are part of an additional aromatic ring, the system is a fused heteroaromatic system, such as a benzo-fused or fused polycyclic heteroaromatic system. Preferred examples are 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,Examples of heteroaryls are also 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzofuran-5-yl, 1-benzofuran ...furan-2- 1H-indazol-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1H-indazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazol-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-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H-benzimidazol-7-yl, 1,3-benzoxazole- 2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,5- or 6-membered benzo-fused rings from the group: 2-benzisoxazol-6-yl, 1,2-benzisoxazol-7-yl, 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1,2-benzisothiazol-7-yl.

[0029] Where a compound can form, via hydrogen shift, tautomers whose structures are not formally encompassed by general formula (I), these tautomers are nevertheless encompassed by the definition of the compounds of the present invention of general formula (I), unless a specific tautomer is being considered. For example, many carbonyl compounds can exist in both keto and enol forms, and both forms are encompassed by the definition of the compounds of general formula (I).

[0030] Depending on the nature of the substituents and the manner in which they are attached, the compounds of general formula (I) may exist as stereoisomers. All possible stereoisomers defined by their specific three-dimensional form, such as enantiomers, diastereomers, Z and E isomers, are encompassed by general formula (I). For example, when one or more alkenyl groups are present, diastereomers (Z and E isomers) may occur. For example, when one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers can be obtained from the mixtures obtained in the preparation by conventional separation methods. Chromatographic separation can be carried out on an analytical scale to find the enantiomeric or diastereomeric excess, or on a preparative scale to prepare test samples for biological testing. Similarly, it is possible to selectively prepare stereoisomers by using stereoselective reactions using optically active starting materials and / or auxiliaries. Thus, the present invention also relates to all stereoisomers that are encompassed by general formula (I) but are not shown in their specific stereoisomeric form, and mixtures thereof.

[0031] If the compounds are obtained as solids, purification can also be carried out by recrystallization or digestion. If the individual compounds of general formula (I) are not obtained in a satisfactory manner by the routes described below, they can be prepared by derivatization of other compounds of general formula (I).

[0032] Suitable methods for isolating, purifying and separating stereoisomers of compounds of general formula (I) are generally known to the skilled artisan from similar cases, for example by physical methods such as crystallization, chromatographic methods, in particular column chromatography and HPLC (High Pressure Liquid Chromatography), optionally distillation under reduced pressure, extraction and other methods, any remaining mixtures can generally be separated by chromatographic separation, for example on chiral solid phases. Methods suitable for preparative or industrial scale are, for example, methods such as the crystallization of diastereomeric salts which can be obtained from diastereomeric mixtures using optically active acids and, where appropriate, when acidic groups are present, optically active bases.

[0033] The present invention also claims a process for the preparation of the compounds of the present invention of general formula (I).

[0034] The compounds of the present invention of general formula (I) can be prepared, inter alia, using known methods. The synthetic routes used and tested proceed from commercially available or easily preparable building blocks. In the following scheme, A, B, Q, R of general formula (I) 2 , R 3 and the moieties m have the meanings defined above and, unless exemplified, are given non-limiting definitions.

[0035] The compounds of the present invention can be prepared, for example, by the method specified in Scheme 1 below. Scheme 1 [ka]

[0036] The pyr(mi)idines of general formula (Ia) can be prepared by coupling the corresponding acetonitrile (EI) with the pyr(mi)idine (EII), where LG is a leaving group, for example in the presence of a base. The base required for this purpose can be, for example, an alkali metal (e.g., sodium or potassium) carbonate or an alkali metal (e.g., sodium) hydride. The reaction is generally carried out in an organic solvent, such as dioxane, dimethylsulfoxide or dimethylformamide, at a temperature between 0° C. and the boiling point of the solvent.

[0037] Pyri(mi)idines of general formula (Ib) can be prepared, for example, by decarboxylative hydrolysis of the corresponding acetonitriles (Ia). Corresponding conditions are, for example, aqueous acid (e.g. hydrochloric acid) heated to boiling.

[0038] Acetonitriles of general formula (EI) are known from the literature and can be prepared, for example, by the methods described in Helvetica Chimica Acta (2003), 86(2), 343-360, Angewandte Chemie, International Edition (2011), 50(19), 4470-4474, and analogous methods.

[0039] Selected detailed synthesis examples of the compounds of the present invention of general formula (I) are given below. 1 H NMR, 13 C NMR, and 19 F NMR spectroscopic data ( 1 400MHz for H NMR, 13 150MHz for C NMR, 19F NMR at 375 MHz, solvents CDCl3, CD3OD or d6-DMSO, internal standard: tetramethylsilane (δ = 0.00 ppm) was obtained on a Bruker instrument, and the listed signals have the meanings given below: b = broad; s = singlet, d = doublet, t = triplet, dd = doublet of doublets, ddd = doublet of doublet of doublets, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = doublet of quartets, dt = doublet of triplets. In the case of diastereomeric mixtures, either significant signals for each of the two diastereomers or the characteristic signal of the main diastereomer are reported. Abbreviations used for chemical groups have, for example, the following meanings: Me=CH3, Et=CH2CH3, t-Hex=C(CH3)2CH(CH3)2, t-Bu=C(CH3)3, n-Bu=unbranched butyl, n-Pr=unbranched propyl, i-Pr=branched propyl, c-Pr=cyclopropyl, c-Hex=cyclohexyl. EXAMPLES

[0040] Synthesis Examples: Table Example No. 1-34: (5-chloropyrimidin-2-yl) [3-fluoro-2-(4-fluorophenoxy)phenyl] acetonitrile

[0041] Synthesis Step 1: 3-Fluoro-2-(4-fluorophenoxy)benzaldehyde [ka]

[0042] A solution of 2.0 g of 2,3-difluorobenzaldehyde (14.1 mmol, 1.0 equiv.), 2.37 g of 2-fluorophenol (21.1 mmol, 1.5 equiv.) and 3.89 g of potassium carbonate (28.1 mmol, 2.0 equiv.) in 30 ml of DMF was stirred at 100° C. for 3 h. Then it was diluted with 50 ml of ether, washed with 2N sodium hydroxide solution (30 ml×2) and saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography. The yield was 2.82 g (85%). 1 H-NMR (400.0 MHz, CDCl3): 10.35 (s,1H); 7.75 (m,1H); 7.43 (m,1H); 7.32 (m,1H); 7.01 (m,2H); 6.91 (m,2H).

[0043] Synthesis step 2: 3-fluoro-2-(4-fluorophenoxy)benzyl alcohol [ka]

[0044] To 2.8 g of 3-fluoro-2-(4-fluorophenoxy)benzaldehyde (12 mmol, 1.0 equiv.) in a mixture of 44 ml of THF and 22 ml of MeOH was added 0.91 g of sodium borohydride (24 mmol, 2.0 equiv.) and the mixture was stirred at room temperature for 3 h. Subsequently, water was added to the solution and it was extracted with ethyl acetate. The organic phase was concentrated under reduced pressure and the residue was dissolved in dichloromethane, dried over sodium sulfate and concentrated under reduced pressure. The product obtained was used without further purification. The yield was 2.77 g (98% crude product). 1 H-NMR (400.0 MHz, CDCl3): 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,1H)

[0045] Synthesis step 3: 3-fluoro-2-(4-fluorophenoxy)benzyl chloride [ka]

[0046] To a solution of 2.70 g of 3-fluoro-2-(4-fluorophenoxy)benzyl alcohol (11.4 mmol, 1.0 equiv.) in 18 ml of toluene, 1.0 ml of thionyl chloride was added and the mixture was stirred at room temperature for 5 hours. Then water was added and extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The product obtained was used without further purification. The yield was 3.29 g (100% crude product). 1 H-NMR (400.0 MHz, CDCl3): 7.31-7.12 (m,3H); 6.98 (m,2H); 6.87 (m,2H); 4.60 (s,2H)

[0047] Synthesis step 4: (3-fluoro-2-(4-fluorophenoxy)phenyl)acetonitrile [ka]

[0048] 3.2 g of 3-fluoro-2-(4-fluorophenoxy)benzyl chloride (12.6 mmol, 1.0 equiv.) and 982 mg of potassium cyanide (15.1 mmol, 1.2 equiv.) were heated to reflux in a mixture of 5 ml of water and 25 ml of ethanol for 6 h. The mixture was then concentrated and the residue was dissolved in dichloromethane. The organic phase was dried over sodium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography. The yield was 1.46 g (47%). 1 H-NMR (400.0 MHz, CDCl3): 7.33 (m,1H); 7.26 (m,1H); 7.18 (m,1H); 6.99 (m,2H); 6.83 (m,2H); 3.72 (s,2H)

[0049] Synthesis Step 5: (5-chloropyrimidin-2-yl)[3-fluoro-2-(4-fluorophenoxy)phenyl]acetonitrile [ka]

[0050] To 500 mg of (3-fluoro-2-(4-fluorophenoxy)phenyl)acetonitrile (2.0 mmol, 1.0 equiv.) in 15 ml of THF was added 179 mg of sodium hydride (60%) (4.49 mmol, 2.2 equiv.) and the mixture was stirred at room temperature for 30 min. Subsequently, 365 mg of 2,5-dichloropyrimidine (2.45 mmol, 1.2 equiv.) was added and the mixture was stirred at room temperature overnight. After that, the mixture was added with 2N hydrochloric acid and extracted with dichloromethane. The organic phase was dried over sodium sulfate, concentrated under reduced pressure and the residue was purified by column chromatography. The yield was 631 mg (87%).

[0051] Table Example No. 1-35: 5-chloro-2-[3-fluoro-2-(4-fluorophenoxy)benzyl]pyrimidine [ka]

[0052] 530 mg of (5-chloropyrimidin-2-yl)[3-fluoro-2-(4-fluorophenoxy)phenyl]acetonitrile (1.48 mmol) in 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%).

[0053] Analogously to the preparative examples cited above and listed at the appropriate points, compounds of the general formulae identified below and shown in Table 1 are obtained. [ka]

[0054] Table 1 [Table 1] TIFF2025510286000012.tif255131TIFF2025510286000013.tif255133TIFF2025510286000014.tif255131TIFF2025510286000015.tif252133 TIFF2025510286000016.tif255132TIFF2025510286000017.tif255132TIFF2025510286000018.tif253132TIFF2025510286000019.tif114131

[0055] Analogously to the preparative examples cited above and listed at the appropriate points, compounds of the general formulae identified below and shown in Table 2 are obtained. [ka]

[0056] Table 2 [Table 2]

[0057] The NMR data of the disclosed embodiments are listed either in the conventional format (δ value, number of hydrogen atoms, multiplet splitting) or in the so-called NMR peak list. In the NMR peak list method, the NMR data of selected embodiments are recorded in the form of an NMR peak list, where the δ value in ppm of each signal peak is listed first, followed by the signal intensity, separated by a space. The numeric pairs of δ value and signal intensity for different signal peaks are listed, separated by a semicolon.

[0058] Thus, the peak list in one embodiment has the following format: δ1 (Intensity 1); δ2 (Intensity 2);....δ i (strength i );.....;δ n (strength n )

[0059] The intensity of sharp signals correlates with the signal height (cm) in a printout of the NMR spectrum, giving the true ratio of signal intensities. In the case of broad signals, several peaks or signal centers and their relative intensities can be shown compared to the most intense signal in the spectrum.

[0060] 1 Calibration of the chemical shifts of H NMR spectra is accomplished with the chemical shifts of tetramethylsilane and / or the solvent, particularly in the case of spectra measured in DMSO. Thus, tetramethylsilane peaks may, but do not necessarily, occur in the NMR peak list.

[0061] 1 The list of H NMR peaks is the same as the conventional 1 Because it resembles a 1 H NMR printout, it usually contains all the peaks listed in a conventional NMR interpretation.

[0062] In addition, the conventional 1 Like 1 H NMR printouts, they may show signals of the solvent, signals of stereoisomers of the target compounds also provided by the present invention, and / or impurity peaks.

[0063] In reporting compound signals within the delta range of the solvent and / or water, 1 Our listing of 1 H NMR peaks shows standard solvent peaks, e.g., the DMSO peak in d6-DMSO and the water peak, which usually have high intensity.

[0064] Such stereoisomers and / or impurities may be typical for a particular preparation process and therefore their peaks, in this case referred to as "by-product fingerprints", may help to identify the reproduction of our preparation process.

[0065] The expert calculates the peaks of the target compounds by known methods (MestreC, ACD simulations, but also empirically evaluated expectations), and can optionally use additional intensity filters to isolate the peaks of the target compounds, if necessary. This isolation is similar to the associated peak picking in conventional 1H NMR interpretation.

[0066] 1 Further details of the 1 H NMR peak listing can be found in Research Disclosure Database Number 564025. [Table 3] TIFF2025510286000023.tif173170

[0067] NMR data of the final product (conventional):

[0068] The chemical examples given in the following sections are 1 H NMR spectroscopic data ( 1 For H NMR at 400 MHz, solvent CDCl3 or d6-DMSO, internal standard: tetramethylsilane δ = 0.00 ppm) were obtained on a Bruker instrument, and the listed signals have the meaning given below: b = broad; s = singlet, d = doublet, t = triplet, dd = doublet of doublets, ddd = doublet of doublet of doublets, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = doublet of quartets, dt = doublet of triplets. In the case of diastereomeric mixtures, reported are either significant signals for each of the two diastereomers or the characteristic signal of the main diastereomer. [Table 4] TIFF2025510286000025.tif255170TIFF2025510286000026.tif253170TIFF2025510286000027.tif255169TIFF2025510286000028.tif254170

[0069] The present invention further provides the use of one or more compounds of general formula (I) as defined above and / or salts thereof, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of formulae (1-1) to (1-209), (2-1) to (2-14) and / or salts thereof, each as defined above, as herbicides and / or plant growth regulators, preferably in crops and / or ornamental plants of useful plants.

[0070] The present invention further provides a method for controlling harmful plants and / or regulating plant growth comprising administering to a subject an effective amount of one or more compounds of general formula (I) and / or salts thereof as defined above, preferably in one of the embodiments specified as preferred or particularly preferred, in particular one or more compounds of formulae (1-1) to (1-209) or (2-1) to (2-14) and / or salts thereof, in each case as defined above, or a composition of the invention as defined below is applied to the (harmful) plant, to the seeds of the (harmful) plant, to the soil or to the area under cultivation in or on which the (harmful) plant grows.

[0071] The present invention also relates to a method for controlling undesirable vegetation, preferably in crops of useful plants, comprising administering to said crop an effective amount of one or more compounds of general formula (I) and / or salts thereof as defined above, preferably in one of the embodiments specified as preferred or particularly preferred, in particular one or more compounds of formulae (1-1) to (1-209) or (2-1) to (2-14) and / or salts thereof, in each case as defined above, or a composition of the invention as defined below is applied to an undesirable plant (e.g., a pest plant such as a monocotyledonous or dicotyledonous weed or an undesirable crop plant), a seed of an undesirable plant (i.e., a plant seed, e.g., a grain, a seed, or a vegetative propagation organ such as a tuber or a shoot portion having a bud), a soil in or on which an undesirable plant grows (e.g., soil of a crop growing area or a non-crop growing area), or an area under cultivation (i.e., an area on which an undesirable plant grows).

[0072] The present invention also relates to a method for controlling harmful plants or for regulating plant growth, preferably useful plant growth, comprising administering an effective amount of one or more compounds of general formula (I) and / or salts thereof as defined above, preferably in one of the embodiments specified as preferred or particularly preferred, in particular one or more compounds of formulae (1-1) to (1-209) or (2-1) to (2-14) and / or salts thereof, in each case as defined above, or a composition of the invention as defined below is applied to a plant, a plant seed (i.e., a seed of a plant, e.g., a grain, a seed, or a vegetative propagation organ such as a tuber or a shoot portion having a bud), to the soil in or on which the plant is growing (e.g., agricultural or non-agricultural soil) or to an area under cultivation (i.e., an area on which the plant is growing).

[0073] In this context, the compounds of the invention or the compositions of the invention can be applied, for example, by pre-sowing (if appropriate also by incorporation into the soil), pre-emergence and / or post-emergence methods.Specific examples of some representatives of monocotyledonous and dicotyledonous weed species that can be controlled by the compounds of the invention are given below, without the intention of limiting the list to specific species.

[0074] In the method according to the invention for controlling harmful plants or regulating plant growth, it is preferred to use one or more compounds of general formula (I) and / or their salts for controlling harmful plants or regulating the growth in crops of useful plants or ornamental plants, where the useful plants or ornamental plants in a preferred configuration are transgenic plants.

[0075] The compounds according to the invention of general formula (I) and / or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants:

[0076] Genera of harmful monocotyledonous plants:Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Narco The genera Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum.

[0077] Dicotyledonous harmful plant genera:Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Birch 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, R. otala), Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica,Viola, Xanthium.

[0078] When the compounds of the present invention represented by general formula (I) are applied to the soil surface before the emergence of harmful plants (grass weeds and / or broadleaf weeds) (pre-emergence method), the emergence of seedlings of the grass weeds or broadleaf weeds is completely prevented, or they grow until they reach the cotyledon stage, after which they stop growing and finally die completely after a lapse of 3 to 4 weeks.

[0079] If the active ingredients of general formula (I) are applied to the green parts of the plants after emergence, growth stops after treatment and the harmful plants either remain in the growth stage at the time of application or they die completely after a certain time, so that in this way competition by harmful weeds for the crop plants is very quickly and persistently eliminated.

[0080] The compounds of the present invention of general formula (I) have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, but also against crop plants of economically important crops, such as, for example, Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Scutellaria ... Dicotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum and Zea are only slightly or not at all damaged depending on the structure of the respective active compound according to the invention and its application rate.For these reasons, the compounds of the invention are highly suitable for selectively controlling undesirable plant growth in plant crops, such as agriculturally useful plants or ornamental plants.

[0081] Moreover, the compounds of the invention of general formula (I) (depending on their specific structure and the applied dose) have remarkable growth-regulating properties in crop plants. They intervene with a regulating effect in the plant's own metabolism and can therefore be used for controlled influence of plant constituents and for example to facilitate harvesting by inducing desiccation and stunting. Moreover, they are also suitable for general suppression and inhibition of undesirable vegetative growth, without killing the plant in the process. Inhibition of vegetative growth plays a major role for many monocotyledonous and dicotyledonous crops, since it can reduce or completely prevent lodging.

[0082] Due to their herbicidal and plant growth regulating properties, the compounds of general formula (I) can also be used to control harmful plants in genetically modified plants or plant crops modified by conventional mutagenesis. In general, transgenic plants are characterized by particularly advantageous properties, such as 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 specific properties relate, for example, to the harvested material in terms of quantity, quality, storability, composition and specific components. For example, transgenic plants with high starch content or altered starch quality, or transgenic plants with different fatty acid composition in the harvested material are known.

[0083] The use of the inventive compounds of general formula (I) and / or their salts in cereals such as wheat, barley, rye, oats, millet, rice and maize, or other useful plants and ornamental economically important transgenic crops such as sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables, is preferred in the context of transgenic crops.

[0084] The compounds of the invention of general formula (I) are also preferably used as herbicides in crops of useful plants which are resistant or have been made resistant by recombinant means to the phytotoxic effects of herbicides.

[0085] The compounds of the present invention of general formula (I) can also be used to control harmful plants in crops of known or yet to be developed genetically modified plants thanks to their herbicidal and plant growth regulating properties. In general, transgenic plants are characterized by certain advantageous properties, such as 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 specific properties relate, for example, to the harvested material in terms of quantity, quality, storability, composition and specific components. For example, transgenic plants with high starch content or altered starch quality, or transgenic plants with different fatty acid compositions in the harvested material are known. Further specific properties can be tolerance or resistance to abiotic stress factors, such as heat, cold, drought, salinity and UV light.

[0086] The use of the compounds of the invention of general formula (I) or their salts in economically important transgenic crops of cereals, such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize, or useful and ornamental plants, such as sugar beet, cotton, soybean, rapeseed, potato, tomato, pea crops and other vegetables, is preferred.

[0087] The compounds of general formula (I) are preferably used as herbicides in crops of useful plants which are tolerant or have been made tolerant by recombinant means to the phytotoxic effects of herbicides.

[0088] Conventional methods for producing new plants with modified properties compared to existing plants consist, for example, in conventional cultivation methods and in the generation of mutants. Alternatively, new plants with modified properties can be produced with the aid of recombinant methods.

[0089] Numerous molecular biology techniques by which new transgenic plants with modified properties can be produced are known to those skilled in the art.For such genetic manipulation, nucleic acid molecules that allow recombination mutagenesis or sequence modification of DNA sequences can be introduced into plasmids.Using standard methods, it is possible to, for example, perform base exchanges, remove partial sequences, or add natural or synthetic sequences.In order to link DNA fragments to each other, adapters or linkers can be added to the fragments.

[0090] For example, the generation of plant cells with reduced activity of a gene product can be achieved by expressing at least one corresponding sense RNA, antisense RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of said gene product.

[0091] For this purpose, it is possible to use DNA molecules that contain the entire coding sequence of the gene product, including any adjacent sequences that may exist, and DNA molecules that contain only parts of the coding sequence, in which case these parts must be long enough to have an antisense effect in cells.It is also possible to use DNA sequences that are highly homologous to the coding sequence of the gene product, but are not completely identical.

[0092] When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired compartment of plant cells.However, to achieve localization in a specific compartment, it is possible, for example, to link the coding region to a DNA sequence that ensures localization in a specific compartment.This type of sequence is known to those skilled in the art (see, for example, Braun et al., EMBO J.11 (1992), 3219-3227).Nucleic acid molecules can also be expressed in organelles of plant cells.

[0093] The transgenic plant cells can be regenerated by known techniques to give whole plants. In principle, the transgenic plants can be plants of any desired plant species, i.e., monocotyledonous as well as dicotyledonous plants.

[0094] In this way it is possible to obtain transgenic plants with altered properties due to the overexpression, suppression or inhibition of a homologous (= natural) gene or gene sequence, or the expression of a heterologous (= foreign) gene or gene sequence.

[0095] The inventive compounds of general formula (I) are preferably used in transgenic crops which are tolerant to growth regulators, such as dicamba, or herbicides which inhibit essential plant enzymes, such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD), or herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and similar active ingredients.

[0096] When the inventive compounds of general formula (I) are used in transgenic crops, not only do they produce effects against harmful plants observed in other crops, but also frequently produce effects specific to their application in the particular transgenic crop, such as modified or specifically broadened spectrum of weeds that can be controlled, modified application rates that can be used for application, preferably good combinability with herbicides to which the transgenic crop is tolerant, and effects influencing the growth and yield of the transgenic crop plants.

[0097] The present invention therefore also relates to the use of the inventive compounds of general formula (I) and / or their salts as herbicides for controlling harmful plants in crops of useful plants or ornamental plants, optionally in transgenic crop plants.

[0098] The use of the compounds of general formula (I) by the pre- or post-emergence method in cereals, here preferably in maize, wheat, barley, rye, oats, millet or rice, is preferred.

[0099] The use of compounds of general formula (I) in soybeans by the pre-emergence or post-emergence method is also preferred.

[0100] The use of the compounds of the invention of formula (I) for controlling harmful plants or regulating plant growth also includes cases where the compound of general formula (I) or a salt thereof is not formed from a precursor substance (a "prodrug") until after application onto or in the plant or in the soil.

[0101] The present invention also provides the use of one or more compounds of general formula (I) or a salt thereof according to the invention, or a composition (defined below) (in a method) for controlling harmful plants or regulating the growth of plants, which comprises applying an effective amount of one or more compounds of general formula (I) or a salt thereof to the plant (harmful plants, together with useful plants, if appropriate), to the plant seed, to the soil in or on which the plant grows, or to the area under cultivation.

[0102] The present invention also relates to a herbicidal and / or plant growth regulating composition comprising: (a) one or more compounds of 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 formulae (1-1) to (1-209) or (2-1) to (2-14) and / or salts thereof, in each case as defined above, and (b) one or more further substances selected from group (i) and / or (ii): (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. not according to general formula (I) as defined above), fungicides, safeners, fertilizers and / or further growth regulators, (ii) one or more formulation adjuvants customary in crop protection; The present invention provides a composition comprising:

[0103] The further pesticide active substances of component (i) of the composition of the present invention are preferably selected from the group of substances described in “The Pesticide Manual”, 16th Edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0104] The herbicidal or plant growth regulating composition according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film-forming agents, thickeners, inorganic salts, dusting agents, carriers which are solid at 25° C. and 1013 mbar, preferably adsorbent granular inert substances, wetting agents, antioxidants, stabilizers, buffer substances, antifoaming agents, water, organic solvents, preferably organic solvents which are miscible with water in any proportion at 25° C. and 1013 mbar.

[0105] The compounds of the present invention of general formula (I) can be applied in the form of wettable powders (dusts), emulsifiable concentrates, sprayable solutions, dusts or granules in the usual formulations.Accordingly, the present invention also provides herbicidal and plant growth regulating compositions comprising the compounds of the present invention of general formula (I) and / or their salts.

[0106] The compounds of the present invention of general formula (I) and / or their salts can be formulated in various ways, according to the biological and / or physicochemical parameters. Possible formulations include, for example, wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as aqueous and oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-mixture solutions, capsule suspensions (CS), dusts (DP), dressings, granules for spraying and soil application, granules in the form of microgranules (GR), spray granules, absorbent granules and adsorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

[0107] The individual formulation types and formulation auxiliaries, such as inert materials, surfactants, solvents and further additives, are also known to those skilled in the art and are described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ, HvOlphen, "Introduction to Clay Colloid Chemistry"; 2nd ed., J. Wiley & Sons, NY, 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, Schoenfeldt, "Grenzflaechenaktive Aethylenoxidaddukte" [Interface-active Ethylene oxide adducts], Wiss. Verlagsgesellschaft., Stuttgart 1976, Winnacker-Kuechler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0108] Wettable powders are preparations which can be homogeneously dispersed in water and which, in addition to the active ingredient, also contain, apart from diluents or inert substances, further surfactants of ionic and / or non-ionic type (wetting agents, dispersants), such as, for example, polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoyl methyl taurate. To prepare wettable powders, the active herbicidal ingredient is comminuted in customary equipment, such as, for example, hammer mills, blower mills and air jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.

[0109] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent (e.g. butanol, cyclohexanone, dimethylformamide, xylene or aromatic substances or hydrocarbons with a relatively high boiling point) or a mixture of such organic solvents and adding one or more surfactants (emulsifiers), ionic and / or non-ionic. Examples of emulsifiers which may be used are: calcium alkylarylsulfonates, 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 condensates, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.

[0110] Dusting products are obtained by grinding the active ingredient with finely distributed solid matter, such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0111] Suspension concentrates can be aqueous or oil-based. They can be prepared, for example, by wet-milling using a standard commercial bead mill, and optionally with the addition of a surfactant (such as those already mentioned above for the other types of formulations).

[0112] Emulsions, e.g., aqueous emulsions (EW), can be prepared, for example, using aqueous organic solvents and, optionally, surfactants (e.g., those already mentioned above for the other formulation types), using stirrers, colloid mills and / or static mixers.

[0113] Granules can be prepared by spraying the active ingredient onto the surface of an adsorbent granular inert material, or by applying an active ingredient concentrate onto the surface of a carrier material (e.g. sand, kaolinite or granular inert material) with an adhesive (e.g. polyvinyl alcohol, sodium polyacrylate or mineral oil). It is also possible to granulate suitable active ingredients (as a mixture with fertilizer, if necessary) in a conventional manner for preparing fertilizer granules.

[0114] Water-dispersible granules are generally prepared by conventional methods such as spray drying, fluid bed granulation, pan granulation, mixing with high speed mixers, and extrusion without solid inert materials.

[0115] For the preparation of bread, fluid bed, extrusion and spray granules, see, for example, the methods described in "Spray-Drying Handbook", 3rd Edition, 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, p. 147 ff.; "Perry's Chemical Engineer's Handbook", 5th Edition, McGraw Hill, New York 1973, p. 8-57.

[0116] For further details regarding the formulation of crop protection agents, see, for example, G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0117] The pesticide preparation, preferably the herbicidal composition or plant growth regulating composition, of the present invention preferably contains 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 the active ingredient of general formula (I) and salts thereof of the total amount.

[0118] In wettable powders (powders), the concentration of the active ingredient is, for example, about 10% to 90% by weight, the remainder to 100% by weight being made up of conventional formulation ingredients. In emulsifiable concentrates, the concentration of the active ingredient can be about 1% to 90% by weight, preferably 5% to 80% by weight. Formulations in the form of powders contain 1% to 30% by weight of active ingredient, preferably usually 5% to 20% by weight; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active ingredient. In wettable granules, the content of the active ingredient depends in part on whether the active ingredient is present in liquid or solid form and on what granulation aids, fillers, etc. are used. In wettable granules, the content of the active ingredient is, for example, 1% to 95% by weight, preferably 10% to 80% by weight.

[0119] In addition, the above formulations of active ingredients may optionally contain the respective customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, as well as solvents, extenders, carriers, as well as dyes, antifoaming agents, evaporation retardants, and agents influencing pH and viscosity. Examples of formulation adjuvants are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).

[0120] The compounds of the present invention of general formula (I) or their salts can be used as they are or in the form of their preparations (formulations) in combination with other pesticide active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators, for example in the form of finished formulations or 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.

[0121] Combination partners which can be used with the compounds of the invention of general formula (I) in mixed formulations or tank mixes are known active ingredients based, for example, on the inhibition of acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th Edition, The British Crop Protection Council and Royal Soc. of Chemistry, 2012 and the documents cited therein.

[0122] Of particular interest is the selective control of harmful plants in crops of useful plants and ornamental plants. The compounds of the present invention of general formula (I) have already shown very good to sufficient selectivity in many crops, but in principle, in some crops, phytotoxicity to crop plants may occur, especially in the case of mixtures with other less selective herbicides. In this context, the combinations of the compounds of the present invention of general formula (I) that are particularly interesting are those that contain the compounds of general formula (I) or their combinations with other herbicides or pesticides and safeners. The safeners used in an effective amount for detoxification reduce the phytotoxic side effects of herbicides / pesticides used in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugarcane, rapeseed, cotton and soybean, preferably cereals.

[0123] The weight ratio of herbicide (mixture) to safener generally depends on the application rate of the herbicide and the efficacy of the safener in question and can vary within wide limits, for example from 200:1 to 1:200, preferably from 100:1 to 1:100, in particular from 20:1 to 1:20. Analogous to the compounds of general formula (I) or mixtures thereof, the safener can be formulated with further herbicides / pesticides and provided and used as a final formulation or tank mix with the herbicide.

[0124] For application, the herbicide or herbicide-safener formulations in commercially available form are, if appropriate, diluted in the usual manner, for example with water in the case of wettable powders (dusts), emulsifiable concentrates, dispersions and water dispersible granules. Dust-type preparations, granules for soil application or granules for scattering and sprayable solutions are usually not further diluted with other inert substances before application.

[0125] The application rate of the compound of general formula (I) and / or its salt is influenced to some extent by external conditions such as temperature, humidity, etc. The application rate can vary within a wide range. For application as a herbicide to control harmful plants, the total amount of the compound of general formula (I) and its salt is preferably in the range of 0.001 to 10.0 kg / ha, preferably in the range of 0.005 to 5 kg / ha, more preferably in the range of 0.01 to 1.5 kg / ha, particularly preferably in the range of 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence application.

[0126] When the compounds of the invention of general formula (I) and / or their salts are used as plant growth regulators, for example as culm stabilizers for crop plants as mentioned above, preferably cereal plants such as wheat, barley, rye, triticale, millet, rice or maize, the total application rate is preferably in the range of 0.001 to 2 kg / ha, preferably in the range of 0.005 to 1 kg / ha, in particular in the range of 10 to 500 g / ha, very particularly preferably in the range of 20 to 250 g / ha. This applies both to pre-emergence and post-emergence application.

[0127] Application as a culm stabilizer can be carried out at various stages of plant development, preference being given to application at the start of vertical growth, for example after the tillering stage.

[0128] Alternatively, application as a plant growth regulator is also possible by treating the seeds, which includes various techniques for dressing and coating the seeds. The application rate depends on the particular technique and can be determined in preliminary tests.

[0129] The combination partners that can be used with the compound of the present invention of general formula (I) in the composition of the present invention (for example, in mixed formulations or in tank mixes) are known active ingredients, for example, based on the inhibition of 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, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and Royal Soc.of Chemistry, 2012 and the documents cited therein.Known herbicides or plant growth regulators that can be combined with the compound of the present invention are, for example, the following active compounds, where the active ingredients are referred to either by their "common name" or chemical name or code number according to the International Organization for Standardization (ISO). They always include all use forms, e.g. acids, salts, esters and, even if not explicitly mentioned, all isomeric forms, such as stereoisomers and optical isomers.

[0130] Examples of such herbicidal mixing partners are: 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, Sulfa Ammonium fluoride, Anilofos, Asulam, Atrazine, Azafenidine, Azimsulfuron, Beflubutamid, Benazolin, Benazolin-ethyl, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Benzulide, Bentazon, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Biranaphos, Biranaphos-sodium, Bispyribac, Bispyribac-sodium, Bromacil, Bromobutide, Bromofenoxime, Bromoxynil, Bromoxynil -Butyrate, -Potassium, -Heptanoate and -Octanoate, Busoxinone, Butachlor, Butafenacil, Butamiphos, Butenachlor, Butralin, Butroxydim, Butyrate, 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, Clacifos, Clethodim, Clodinafop, Clodinafop-propargyl, Clomazone, Clomeprop, Clopyralid, Cloransulam, Cloransulam-methyl, Cumiluron, Cyanamide, Cyanazine, Cycloate, Cyclopirimorate, Cyclosulfamuron, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, -isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedicine FAM, Detosyl-pyrazolate (DTP), Dicamba, Dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, Dichlorprop, Dichlorprop-P, Diclofop, Diclofop-methyl, Diclofop-P-methyl, Diclosulam, Difenzoquat, Diflufenican, Diflufenzopyr, Diflufe Dimethapyr-sodium, Dimefuron, Dimepiperate, Dimethachlor, Dimethamethrin, Dimethenamid, Dimethenamid-P, Dimetrasulfuron, Dinitramine, Dinoterb, Diphenamide, Diquat, Diquat-dibromide, Dithiopyr, Diuron, DNOC, Endothal, EPTC, Esprocarb, Ethalfluralin, Ethametosulfuron, Ethametosulfuron-methyl, Ethiozine, Ethofumesate, Ethoxyphene, Ethoxyphene-ethyl, Etho Xysulfuron, etobenzanide, F-9600, F-5231, i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]-ethanesulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, 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, flucetos Flufuron, Fluchloralin, Flufenacet, Flufenpyr, Flufenpyr-ethyl, Flumetsulam, Flumicrac, Flumicrac-pentyl, Flumioxazin, Fluometuron, Flurenol, Flurenol-butyl, -dimethylammonium and -methyl, Fluoroglycofen, Fluoroglycofen-ethyl, Flupropanate, Flupyrsulfuron, Flupyrsulfuron-methyl-sodium, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr-meptyl, Flurtamone, Fluthiacet, Fluthiacet-methyl, Fomesafen, Fomesafen-sodium, Foramsulfuron, Fosamine, Glufosinate, Glufosinate-P-sodium, Glufosinate-P-ammonium, Glufosinate-P-sodium, Glyphosate, Glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, namely, O-(2,4-dimethyl-6-nitrophenyl) O-ethyl-isopropyl phosphoramidothioate, haloxifen, haloxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e., 1-(dimethoxyphosphoryl)ethyl (2,4-Dichlorophenoxy)acetate, hydantocidin, 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-octa noate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, carbutyrate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butyric acid, -dimethylammonium, -2-ethylhexyl, -Isopropylammonium, -Potassium and -Sodium, MCPB, MCPB-Methyl, -Ethyl and Sodium, Mecoprop, Mecoprop-Sodium and Mecoprop-Butotyl, Mecoprop-P, Mecoprop-P-Butotyl, -Dimethylammonium, -2-Ethylhexyl and -Potassium, Mefenacet, Mefluidide, Mesosulfuron, Mesosulfuron-Methyl, Mesotrione, Metabenzthiazuron, Metam, Metamifop, Metamitron, Metazachlor, Metazosulfuron, Metabenzthia Zuron, methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metoslam, methoxron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e., N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., 4-(2,4-Dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, nebulon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat-dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, petroxamide, petroleum, phenmedipham, picloram, picolinafen, picolinafen Noxaden, 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, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron -ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, piroxisulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rim Sulfuron, Saflufenacil, Sethoxydim, Siduron, Simazine, Simetryn, SL-261, Sulcotrione, Sulfentrazone, Sulfometuron, Sulfometuron-methyl, Sulfosulfuron, SYN-523, SYP-249, i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-Benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiaphenacyl, tolpyralate, topramezone, tralkoxy Dim, triafamone, triallate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, as well as the following compounds: [ka]

[0131] Examples of plant growth regulators as possible mixing partners are: Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-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, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isopropyl alcohol, ethyl ... Prothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 1-methylcyclopropene, 2-(1-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.

[0132] Useful combination partners of the compounds of the invention of general formula (I) also include, for example, the following safeners: S1) Compounds from the group of heterocyclic carboxylic acid derivatives: S1 a ) Dichlorophenylpyrazoline-3-carboxylic acid type compounds (S1 a ), preferably compounds such as: 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) ("mefenpyr-diethyl") and related compounds (which are described in WO-A-91 / 07874); S1 b ) Derivatives of dichlorophenylpyrazole carboxylic acid (S1 b ), preferably compounds such as: ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4) and related compounds, which are described in EP-A-333131 and EP-A-269806; S1 c ) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c ), preferably compounds such as: Ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds (which are described, for example, in EP-A-268554); S1 d ) Triazole carboxylic acid type compounds (S1 d ), preferably compounds such as: Fenchlorazole (-ethyl ester), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate (S1-7) and related compounds (which are described in EP-A-174562 and EP-A-346620); S1 e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (S1 e ), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds, which are described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) ("isoxadifen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13), which are described in patent application WO-A-95 / 07897.

[0133] S2) Compounds from the group of 8-quinolinoxy derivatives (S2): S2 a ) 8-Quinolineoxyacetic acid type compound (S2 a), preferably 1-methylhexyl (5-chloro-8-quinolinoxy)acetate ("cloquintocet-mexyl") (S2-1), 1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), 5), methyl (5-chloro-8-quinolinoxy)acetate (S2-6), allyl (5-chloro-8-quinolinoxy)acetate (S2-7), 2-(2-propylideneiminooxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9) and related compounds (these are described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366), and furthermore (5-chloro-8-quinolinoxy)acetic acid (S2-10), its hydrates and salts, such as its lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, which are described in WO-A-2002 / 34048; S2 b ) (5-chloro-8-quinolinoxy)malonic acid type compound (S2 b ), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methylethyl (5-chloro-8-quinolinoxy)malonate and related compounds, which are described in EP-A-0 582 198.

[0134] S3) Active ingredients of the dichloroacetamide type (S3), which are often used as pre-emergence safeners (soil-acting safeners), e.g. "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-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(1,3-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-1-oxa-3-azaspiro[4.5]decane) [from Nitrokemia or Monsanto] (S3-7), "TI-35" (1-dichloroacetylazepane) [from TRI-Chemical RT] (S3-8), "Diclonon" (Dicyclonon) or "BAS145138" or "LAB145138" (S3-9), ((RS)-1-Dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) [from BASF], "Furilazol" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10) and its (R)-isomer (S3-11).

[0135] S4) Compounds from the group of acylsulfonamides (S4): S4 a ) Equation (S4 a ) and their salts, which are described in WO-A-97 / 45016. [ka] [During the ceremony, R A 1 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, where the last two mentioned radicals are selected from the group consisting of halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio, and further, in the case of cyclic radicals, from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl. A is substituted with a substituent of R A 2 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3; m A is 1 or 2; v A is 0, 1, 2 or 3; S4 b ) The following formula (S4 b ) compounds of the 4-(benzoylsulfamoyl)benzamide type and their salts, which are described in WO-A-99 / 16744. [ka] [During the ceremony, R B 1 , R B 2 are independently hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, R B 3 is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl or (C1-C4)-alkoxy, and m B is either 1 or 2, For example, in the formula: R B 1 = cyclopropyl, R B 2= hydrogen and (R B 3 ) = 2-OMe ("cyprosulfamide", S4-1), R B 1 = cyclopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe (S4-2), R B 1 = ethyl, R B 2 = hydrogen and (R B 3 )=2-OMe(S4-3), R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe (S4-4) and R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 )=2-OMe(S4-5)〕; S4 c ) Equation (S4 c ) from the class of benzoylsulfamoylphenylureas, which are described in EP-A-365484, [ka] [During the ceremony, R C 1 , R C 2 are independently hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, R C 3 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3, and m C is 1 or 2. for example, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea; 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea; 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea]; S4 d ) Equation (S4 d ) and salts thereof (which are known, for example, from CN 101838227), [ka] [During the ceremony, R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3; m D is 1 or 2; R D 5 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl or (C5-C6)-cycloalkenyl.

[0136] S5) Active ingredients (S5) selected from the class of the hydroxyaromatic compounds and aromatic-aliphatic carboxylic acid derivatives, such as, for example, ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid (these are described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001).

[0137] S6) Active ingredients (S6) selected from the class of the 1,2-dihydroquinoxalin-2-ones, such as 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, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one (which are described in WO-A-2005 / 112630).

[0138] S7) Compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), such as, for example, methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid (which are described in WO-A-98 / 38856).

[0139] S8) Compounds of formula (S8), which are described in WO-A-98 / 27049, [ka] where the symbols and indices are defined as follows: R D 1 is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, R D 2 is hydrogen or (C1-C4)-alkyl, R D 3 is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, in which each of said carbon-containing groups is unsubstituted or substituted with one or more, preferably up to three, identical or different groups selected from the group consisting of halogen and alkoxy, or a salt thereof, n D is an integer from 0 to 2.

[0140] S9) Active ingredients (S9) selected from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones, such as 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8) (which are described in WO-A-1999 / 000020).

[0141] S10) Formula (S10 a ) or formula (S10 b ) which are described in WO-A-2007 / 023719 and WO-A-2007 / 023764, [ka] [During the ceremony, R E 1 is halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3, Y E , Z E are independently O or S; n E is an integer from 0 to 4, R E 2 is (C1-C 16 )-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl, benzyl, halobenzyl; R E 3 is hydrogen or (C1-C6)-alkyl.

[0142] S11) Active ingredients of the oxyimino compound type (S11), which are known as seed dressing agents, e.g. "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet / sorghum against injury by metolachlor; "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a seed dressing safener for millet / sorghum against damage by metolachlor, and "Siometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is a known seed dressing safener for millet / sorghum against injury by metolachlor.

[0143] S12) Active ingredients (S12) selected from the class of isothiochromanones, such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds (WO-A-1998 / 13361).

[0144] S13) One or more compounds selected from the following group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for corn against injury caused by thiocarbamate herbicides; "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice; "Flurazole" (2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate benzyl) (S13-3), which is known as a seed dressing safener for millet / sorghum against injury by alachlor and metolachlor; "CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against injury by imidazolinones; "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn; "MG 838" (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) [from Nitrokemia]; "Disulfoton" (O,O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7); "Dietholate" (O,O-diethyl O-phenylphosphorothioate) (S13-8); “Mephenate” (4-chlorophenyl methylcarbamate) (S13-9).

[0145] S14) Active ingredients that have a herbicidal effect against harmful plants as well as a phytotoxicity reducing effect against crop plants such as rice, e.g. "Dimepyrate" or "MY 93" (S-1-methyl 1-phenylethylpiperidine-1-carbothioate), known as a safener for rice against injury caused by the herbicide molinate; "Dymron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolyl urea), which is known as a safener for rice against injury caused by the herbicide imazosulfuron; "Cumyluron" = "JC 940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, (see JP-A-60087270), which is known as a safener for rice against injury by some herbicides; "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against injury caused by some herbicides; "CSB" (1-Bromo-4-(chloromethylsulfonyl)benzene) from Kumiai (CAS Reg. No. 54091-06-4), which is known as a safener against injury by some herbicides in rice.

[0146] S15) Compounds of formula (S15) or tautomers thereof (which are described in WO-A-2008 / 131861 and WO-A-2008 / 131860) [ka] [During the ceremony, R H 1 is a (C1-C6)-haloalkyl group, and R H 2 is hydrogen or a halogen, and R H 3 , R H 4 are each independently hydrogen, (C1-C 16 )-Alkyl, (C2-C 16 )-alkenyl or (C2-C 16 )-alkynyl, wherein each of the last three radicals is unsubstituted or substituted by one or more radicals selected from the group: halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)-cycloalkyl, unsubstituted or substituted phenyl and unsubstituted or substituted heterocyclyl, or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl (wherein the ring is fused at one side of the ring to a 4-6-membered saturated or unsaturated carbocyclic ring) or (C4-C6)-cycloalkenyl (wherein the ring is fused at one side of the ring to a 4-6-membered saturated or unsaturated carbocyclic ring), wherein each of the last four groups is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)cycloalkyl, unsubstituted or substituted phenyl and unsubstituted or substituted heterocyclyl; or R H 3 is (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy; and R H 4is hydrogen or (C1-C4)-alkyl, or R H 3 and R H 4 together with the nitrogen atom to which it is directly attached, is a 4-8 membered heterocyclic ring which, in addition to the nitrogen atom, can also contain further ring heteroatoms (preferably up to two further ring heteroatoms selected from the group N, O and S) and which is unsubstituted or substituted with one or more radicals selected from the group halogen, cyano, nitro, (C-C)-alkyl, (C-C)-haloalkyl, (C-C)-alkoxy, (C-C)-haloalkoxy and (C-C)-alkylthio.

[0147] S16) Active ingredients used primarily as herbicides but also having a phytotoxicity-safening effect on crop plants, e.g. (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), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl).

[0148] Preferred safeners to be combined with the compounds of general formula (I) and / or salts thereof according to the present invention, in particular with the compounds of formulae (1-1) to (1-209) or (2-1) to (2-14) and / or salts thereof, are cloquintocet-mexyl, cyprosulfamide, fentirolazole-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.

[0149] Biological Examples:

[0150] The following abbreviations are used in the examples and tables that follow: Unwanted plants / weeds: ABUTH:Abutilon theophrasti ALOMY: Black-legged foxtail (Alopecurus myosuroides) AMARE: Amaranthus retroflexus DIGSA: Digitaria sanguinalis ECHCG: Golden millet (Echinochloa crus-galli) KCHSC: Kochia scoparia LOLRI:Lolium rigidum MATIN: Matricaria inodora POAAN: Annual grass (Poa annua) SETVI: Green foxtail (Setaria viridis) STEME:Kochakobe (Stellaria media) VERPE: Veronica persica VIOTR: Viola tricolor

[0151] A. Post-emergence herbicidal efficacy at 1280 g / ha

[0152] Seeds of monocotyledonous and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (in each case one monocotyledonous or dicotyledonous weed plant was double-sown per pot), covered with soil and cultivated in a greenhouse under controlled growth conditions. 2-3 weeks after sowing, the test plants were treated at the one-leaf stage. The compounds of the invention formulated in the form of wettable powders (WP) or emulsifiable concentrates (EC) were applied to the green parts of the plants as aqueous suspensions or emulsions, with the addition of 0.5% additive in a water application rate equivalent to 600 liters per hectare. After maintaining the test plants in the greenhouse for about 3 weeks under optimal growth conditions, the activity of the preparations was visually evaluated in comparison with untreated controls. For example, 100% activity = plant died, 0% activity = same as control plants.

[0153] The following Tables A1 to A12 show the efficacy of selected compounds of general formula (I) according to Table 1 on various harmful plants and at application rates corresponding to 1280 g / ha, obtained by the test procedures specified above.

[0154] Table A1: Post-emergence efficacy (%) at 1280g / ha against ABUTH [Table 5] TIFF2025510286000038.tif54118

[0155] Table A2: Post-emergence efficacy (%) at 1280 g / ha against ALOMY [Table 6]

[0156] Table A3: Post-emergence efficacy (%) at 1280 g / ha against AMARE [Table 7] TIFF2025510286000041.tif162119

[0157] Table A4: Post-emergence efficacy (%) at 1280g / ha against DIGSA [Table 8]

[0158] Table A5: Post-emergence efficacy (%) at 1280 g / ha against ECHCG [Table 9]

[0159] Table A6: Post-emergence efficacy (%) at 1280 g / ha against KCHSC [Table 10] TIFF2025510286000045.tif90119

[0160] Table A7: Postemergence efficacy (%) at 1280 g / ha against LOLRI [Table 11]

[0161] Table A8: Post-emergence efficacy (%) at 1280 g / ha against MATIN [Table 12]

[0162] Table A9: Post-emergence efficacy (%) at 1280 g / ha against POAAN [Table 13] TIFF2025510286000049.tif108120

[0163] Table A10: Post-emergence efficacy (%) against SETVI at 1280 g / ha [Table 14]

[0164] Table A11: Post-emergence efficacy (%) at 1280 g / ha against STEME [Table 15] TIFF2025510286000052.tif84121

[0165] Table A12: Post-emergence efficacy (%) at 1280 g / ha against VERPE [Table 16] TIFF2025510286000054.tif172121

[0166] The test results show that the compounds of the present invention of general formula (I) in post-emergence treatment show good herbicidal activity against selected harmful plants 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 respective application rates of 1280 g of active ingredient per hectare.

[0167] B. Post-emergence herbicidal efficacy at 80 g / ha

[0168] Seeds of monocotyledonous and dicotyledonous weed and crop plants were placed in sandy loam in plastic or organic growing pots, covered with soil and cultivated in a greenhouse under controlled growth conditions. 2-3 weeks after sowing, the test plants were treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or emulsifiable concentrates (EC), were then sprayed onto the green parts of the plants as aqueous suspensions or emulsions with 0.5% additives at a water application rate of 600 l / ha (equivalent). After maintaining the test plants in the greenhouse for about 3 weeks under optimal growth conditions, the activity of the preparations was visually evaluated in comparison with untreated controls. For example, 100% activity = plant died, 0% activity = similar to control plants.

[0169] The following tables B1 to B10 show the effect of selected compounds of general formula (I) according to table 1 on various harmful plants and at an application rate corresponding to 80 g / ha, obtained by the above test procedure.

[0170] Table B1: Post-emergence efficacy (%) at 80g / ha against ABUTH [Table 17]

[0171] Table B2: Post-emergence efficacy (%) at 80 g / ha against ALOMY [Table 18]

[0172] Table B3: Post-emergence efficacy (%) at 80 g / ha against AMARE [Table 19]

[0173] Table B4: Post-emergence efficacy (%) at 80 g / ha against DIGSA [Table 20]

[0174] Table B5: Post-emergence efficacy (%) at 80 g / ha against ECHCG [Table 21]

[0175] Table B6: Post-emergence efficacy (%) at 80 g / ha against KCHSC [Table 22]

[0176] Table B7: Post-emergence efficacy (%) at 80 g / ha against POLCO [Table 23]

[0177] Table B8: Post-emergence efficacy (%) at 80 g / ha against SETVI [Table 24]

[0178] Table B9: Post-emergence efficacy (%) at 80 g / ha against VERPE [Table 25]

[0179] Table B10: Post-emergence efficacy (%) at 80 g / ha against VIOTR [Table 26]

[0180] The test results show that the compounds of the present invention of general formula (I) in post-emergence treatments show good herbicidal efficacy against selected harmful plants, such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Polygonum convolvulus, Setaria viridis, Veronica persica and Viola tricolor, respectively, at application rates of 80 g of active substance per hectare.

[0181] C. Pre-emergence herbicide efficacy at 1280 g / ha

[0182] The seeds of monocotyledonous and dicotyledonous weed plants are placed in sandy loam soil in plastic pots (in each case, one monocotyledonous or dicotyledonous weed plant is double-seeded per pot) and covered with soil.The compounds of the present invention formulated in the form of wettable powder (WP) or emulsifiable concentrate (EC) are then applied to the surface of the covered soil with a water application rate of 600 liters per hectare (equivalent) as an aqueous suspension or emulsion with 0.5% additive.After treatment, the pots are placed in a greenhouse and maintained under good growth conditions for the test plants.After about 3 weeks, the efficacy of the preparation is visually scored as a percentage, compared to untreated control. For example, 100% activity = plant died, 0% activity = same as control plants.

[0183] The following Tables C1 to C12 show the effect of selected compounds of general formula (I) according to Table 1 on various harmful plants and at application rates corresponding to 1280 g / ha, obtained by the test procedures specified above.

[0184] Table C1: Pre-emergence efficacy (%) at 1280g / ha against ABUTH [Table 27] TIFF2025510286000066.tif42119

[0185] Table C2: Pre-emergence efficacy (%) at 1280 g / ha against ALOMY [Table 28]

[0186] Table C3: Pre-emergence efficacy (%) at 1280 g / ha against AMARE [Table 29] TIFF2025510286000069.tif141119

[0187] Table C4: Pre-emergence efficacy (%) at 1280 g / ha against DIGSA [Table 30] TIFF2025510286000071.tif41119

[0188] Table C5: Pre-emergence efficacy (%) at 1280 g / ha against ECHCG [Table 31]

[0189] Table C6: Pre-emergence efficacy (%) at 1280 g / ha against KCHSC [Table 32]

[0190] Table C7: Pre-emergence efficacy (%) at 1280 g / ha against LOLRI [Table 33]

[0191] Table C8: Pre-emergence efficacy (%) at 1280 g / ha against MATIN [Table 34]

[0192] Table C9: Pre-emergence efficacy (%) at 1280 g / ha against POAAN [Table 35] TIFF2025510286000077.tif97119

[0193] Table C10: Pre-emergence efficacy (%) at 1280 g / ha against SETVI [Table 36] TIFF2025510286000079.tif34119

[0194] Table C11: Pre-emergence efficacy (%) at 1280 g / ha against STEME [Table 37] TIFF2025510286000081.tif57121

[0195] Table C12: Pre-emergence efficacy (%) at 1280 g / ha against VERPE [Table 38]

[0196] The test results show that the compounds of the present invention of general formula (I) in pre-emergence treatment show good herbicidal activity against selected harmful plants 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 respective application rates of 1280 g of active ingredient per hectare.

[0197] D. Efficacy of pre-emergence herbicides at 80 g / ha

[0198] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are placed in plastic or organic planting pots and covered with soil.The compound of the present invention formulated in the form of wettable powder (WP) or emulsifiable concentrate (EC) is then applied to the surface of the covered soil as an aqueous suspension or emulsion with 0.5% additive, with a water application rate equivalent to 600 l / ha.After treatment, the pot is placed in a greenhouse and maintained under good growth conditions for the test plants.After about 3 weeks, the efficacy of the preparation is visually scored as a percentage, compared to untreated control.For example, 100% activity=plant is dead, 0% activity=similar to control plant.

[0199] The following Tables D1 to D12 show the effect of selected compounds of general formula (I) according to Table 1 on various harmful plants and at application rates corresponding to 80 g / ha, obtained by the test procedures specified above.

[0200] Table D1: Pre-emergence efficacy (%) at 80g / ha against ABUTH [Table 39]

[0201] Table D2: Pre-emergence efficacy (%) at 80g / ha against ALOMY [Table 40]

[0202] Table D3: Pre-emergence efficacy (%) at 80g / ha against AMARE [Table 41]

[0203] Table D4: Pre-emergence efficacy (%) at 80g / ha against DIGSA [Table 42]

[0204] Table D5: Pre-emergence efficacy (%) at 80g / ha against ECHCG [Table 43]

[0205] Table D6: Pre-emergence efficacy (%) at 80g / ha against KCHSC [Table 44]

[0206] Table D7: Pre-emergence efficacy (%) at 80 g / ha against LOLRI [Table 45]

[0207] Table D8: Pre-emergence efficacy (%) at 80g / ha against MATIN [Table 46]

[0208] Table D9: Pre-emergence efficacy (%) at 80 g / ha against POLCO [Table 47]

[0209] Table D10: Pre-emergence efficacy (%) at 80g / ha against SETVI [Table 48]

[0210] Table D11: Pre-emergence efficacy (%) at 80g / ha against VERPE [Table 49]

[0211] Table D12: Pre-emergence efficacy (%) at 80g / ha against VIOTR [Table 50]

[0212] The test results show that the compounds of the present invention of general formula (I) in pre-emergence treatment show good herbicidal efficacy against selected harmful plants 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 respective application rates of 80 g of active ingredient per hectare.

Claims

1. General formula (I): 【Chemistry 1】 [During the ceremony, A is nitrogen or CR １ And, R １ These are hydrogen, CN, or halogens. B is CH, CR ２ or N, Q is Y - (C ２ -C ６ ) - Haloalkyl, where Y is directly bonded, oxygen, S(O) ｎ CO or OSO ２ Represents, or Q is Z-aryl or Z-heteroaryl, where aryl is substituted with 1 to 5 substituents independently selected from the group of R ４ and heteroaryl is substituted with up to 2 substituents independently selected from the group of R ４ and Z represents a direct bond, O, S(O) ｎ or CH ２ and R ２ These are, independently, halogen, cyano, nitro, amino, (C １ -C ４ )-alkyl, (C １ -C ４ )-Haloalkyl, cyclopropyl, (C １ -C ４ )-alkoxy, (C １ -C ４ )- Haloalkoxy or (C １ -C ４ )-alkyl-S(O) ｎ - and m is 0, 1, 2, or 3. n is 0, 1, or 2. R ３ (C) １ -C ４ )-alkyl, (C １ -C ４ )-Haloalkyl, (C １ -C ４ )-alkoxy, (C １ -C ２ )- Haloalkoxy or (C １ -C ４ )-alkyl-S(O) ｎ - and However, A is CR １ If R ３ It must not be hydrogen. R ４ (C) １ -C ４ )-alkyl, (C １ -C ８ )-Haloalkyl, (C １ -C ４ )-alkoxy, (C １ -C ２ )-haloalkoxy, (C １ -C ４ )-alkoxymethyl or (C １ -C ４ )-alkyl-S(O) ｎ - and and R ５ [It is hydrogen or CN.] Substituting 2-C-azine or a salt thereof.

2. During the ceremony, A is nitrogen or CR １ And, R １ However, it is hydrogen, CN, or halogen, B is CH, CR ２ or N, Q is Y - (C ３ -C ５ ) - Haloalkyl, where Y is directly bonded, oxygen, S(O) ｎ CO or OSO ２ Represents, or Q is a Z-aryl or Z-heteroaryl, where aryl is R ４ It is substituted with 1 to 3 substituents independently selected from the group, and the heteroaryl is R ４ It is substituted with up to two substituents independently selected from the group, and Z is directly bonded, O, S(O) ｎ or CH ２ This represents, R ２ However, independently, halogen, cyano, amino, (C １ -C ４ )-alkyl, (C １ -C ４ )-Haloalkyl, cyclopropyl, (C １ -C ４ )-alkoxy, (C １ -C ４ )- Haloalkoxy or (C １ -C ４ )-alkyl-S(O) ｎ - and m is 0, 1, 2, or 3, n is 0, 1, or 2, R ３ However, hydrogen, halogen, cyano, (C １ -C ４ )-alkyl, (C １ -C ４ )-Haloalkyl, (C １ -C ４ )-alkoxy or (C １ -C ２ ) - It is a haloalkoxy, However, A is CR １ If R ３ It must not be hydrogen. R ４ is halogen, cyano, (C １ -C ４ )-alkyl, (C １ -C ８ )-haloalkyl or (C １ -C ４ )-alkoxymethyl, and R ５ However, it is hydrogen or CN. A compound of general formula (I) or a salt thereof as described in claim 1.

3. During the ceremony, A is nitrogen or CR １ And, R １ However, these are hydrogen, cyano, fluorine, or chlorine. B is CH, CR ２ or N, and Q is Y - (C ３ -C ５ ) - Haloalkyl, where Y is a direct bond, oxygen, S, CO, or OSO ２ Represents, or Q is a Z-aryl or Z-heteroaryl, where aryl is R ４ It is substituted with one or two substituents independently selected from the group, and the heteroaryl is R ４ It is substituted by up to two substituents independently selected from the group, and Z is a direct bond, O, S, or CH ２ This represents, R ２ However, independently, fluorine, chlorine, bromine, cyano, methyl, CF ３ or methoxy, m is 0, 1, or 2, R ３ However, hydrogen, chlorine, bromine, fluorine, cyano, methyl, CF ３ , methoxy or CHF ２ It is O, However, A is CR １ If R ３ It must not be hydrogen. R ４ However, fluorine, chlorine, methyl, CHF ２ CF ３ , methoxymethyl, and R ５ However, it is hydrogen or CN. A compound of general formula (I) or a salt thereof as described in claim 1.

4. During the ceremony, A is nitrogen or CR １ And, R １ However, these are hydrogen, cyano, fluorine, or chlorine. B is CH, CR ２ or N, Q is Y - (C ３ -C ５ ) - Haloalkyl, where Y is a direct bond, oxygen, S, CO, or OSO ２ Represents, or Q is a Z-aryl or Z-heteroaryl, where aryl is R ４ It is substituted with one or two substituents independently selected from the group, and the heteroaryl is R ４ It is substituted by up to two substituents independently selected from the group, and Z is a direct bond, O, S, or CH ２ This represents, R ２ However, independently, fluorine, chlorine, bromine, cyano, methyl, CF ３ or methoxy, m is 0, 1, or 2, R ３ However, hydrogen, chlorine, bromine, fluorine, cyano, methyl, CF ３ , methoxy or CHF ２ It is O, However, A is CR １ If R ３ It must not be hydrogen. R ４ However, fluorine, chlorine, methyl, CHF ２ CF ３ or methoxymethyl, and R ５ However, it is hydrogen or CN. A compound of general formula (I) or a salt thereof as described in claim 1.

5. During the ceremony, A is nitrogen, CH, CCN, or CF. B is CH, Q is (CH ２ ) ３ CF ３ , (CH ２ ) ４ CF ３ , S (CH ２ ) ３ CF ３ , S (CH ２ ) ３ Cl, SO(CH ２ ) ３ Cl, SO(CH ２ ) ２ CF ３ , SO (CH ２ ) ３ CF ３ SO ２ (CH ２ ) ３ CF ３ , O(CH ２ ) ３ CF ３ , C(O)(CH ２ ) ３ CF ３ OSO ２ (CH ２ ) ３ CF ３ OSO ２ (CH ２ ) ２ CF ３ OSO ２ (CH ２ ) ３ Cl, 4-fluorobenzyl, 4-chlorophenyl, 3,4-difluorophenyl, 4-fluorophenoxy, 4-fluorophenylsulfanyl, 2,4-Cl ２ -Phenylsulfonyl, 2,4-Cl ２ - Phenylsulfanyl, 2,4-Cl ２ -Phenyl sulfinyl, 4-(CF ３ )-pyrazole-1-yl, 5-Cl-pyrimidine-2-oxy, 5-F-pyrimidine-2-oxy, 5-Cl-3-F-pyridine-2-oxy, 3-(CHF ２ )-Isoxazole-5-yl, 5-(CHF ２ )-Isoxazole-3-yl, 1,2,4-Oxadiazole-3-yl, 5-Methyl-1,2,4-Oxadiazole-3-yl, 5-(CHF ２ )-1,2,4-oxadiazole-3-yl,5-(CF ３ )-1,2,4-oxadiazole-3-yl, 5-F-pyrimidine-2-ylsulfanil, 5-Cl-pyrimidine-2-ylsulfanil, 5-Cl-pyrimidine-2-ylsulfinyl, 5-Cl-pyrimidine-2-ylsulfonyl, 4-Cl-pyrazole-1-ylmethyl, 4-Br-pyrazole-1-ylmethyl or 4-(CF ３ )-pyrazole-1-ylmethyl, R ２ However, independently, fluorine, chlorine, bromine, cyano, methyl, CF ３ or methoxy, m is 0, 1, or 2, R ３ However, these are chlorine, bromine, or fluorine. and R ５ However, it is hydrogen or CN. A compound of general formula (I) or a salt thereof as described in claim 1.

6. A herbicidal composition characterized by a herbicidal activity amount of at least one compound of general formula (I) as described in any one of claims 1 to 5.

7. The herbicidal composition according to claim 6, which is a mixture with a formulation aid.

8. The herbicidal composition according to claim 6, comprising at least one further pesticide-active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, phytotoxicity reducers, and growth regulators.

9. The herbicidal composition according to claim 8, comprising a phytotoxicity-reducing agent.

10. The herbicidal composition according to claim 9, comprising cyprosulfamide, croquintoset-mexyl, mefenpyr-diethyl, or isoxadifen-ethyl.

11. The herbicidal composition according to claim 6, comprising an additional herbicide.

12. A method for controlling undesirable plants, characterized by applying an effective amount of a herbicidal composition characterized by at least one compound of general formula (I) as described in any of claims 1 to 5, or an active amount of at least one compound of general formula (I) as described in any of claims 1 to 5, to a location of plants or undesirable vegetation.

13. Use of a herbicidal composition characterized by a herbicidal active amount of a compound of general formula (I) according to any one of claims 1 to 5, or at least one compound of general formula (I) according to any one of claims 1 to 5, for controlling undesirable plants.

14. The use according to claim 13, characterized in that the compound of general formula (I) is used to control undesirable plants in a crop of useful plants.

15. The use according to claim 14, characterized in that the useful plant is a transgenic useful plant.

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