Substituted N-phenyluracils and their salts and their use as herbicidal active substances

Abstract

The present invention relates to substituted N-phenyluracils of general formula (I) or salts thereof (Formula I), in which the radicals in general formula (I) correspond to the definitions given herein, and to their use as herbicides, in particular as herbicides for controlling weeds and / or grass weeds in crops and / or as plant growth regulators for influencing the growth of crops. [Formula 1] TIFF2025534472000132.tif31163

Description

[Technical Field]

[0001] 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.

[0002] In particular, the present invention relates to substituted N-phenyluracils and their salts, processes for their preparation and their use as herbicides, in particular as herbicides for controlling broadleaf weeds and / or grass weeds in crops of useful plants and / or as plant growth regulators for influencing the growth of crops of useful plants. [Background technology]

[0003] The crop protection products or active ingredients for controlling undesirable vegetation known to date for selectively controlling harmful plants in useful plant crops sometimes have the following disadvantages in their application: (a) they have insufficient herbicidal activity, even if they have herbicidal activity against certain harmful plants; (b) the range of harmful plants that can be controlled using the active ingredients is not wide enough; (c) their selectivity among useful plant crops is too low; and / or (d) they have an undesirable toxicological profile. Furthermore, some active ingredients that can be used as plant growth regulators for many types of useful plants cause undesirable yield reductions in other useful plants, or are only compatible with crop plants within a narrow application range, even if they are compatible with crop plants. Some known active ingredients cannot be produced economically on an industrial scale due to difficult-to-obtain precursors and reagents, or they exhibit insufficient chemical stability. In the case of other active ingredients, their activity is excessively dependent on environmental conditions such as climatic and soil conditions.

[0004] The herbicidal activity of these known compounds (especially at low application rates) and / or their compatibility with crop plants still needs to be improved.

[0005] It is known from various documents that certain substituted N-aryluracils can be used as herbicidal active ingredients (cf. EP1106607, EP408382, EP473551, EP648749, US4943309, US5084084, US5127935, US6537948, JP2001 / 348376, JP2001 / 354661, JP2002 / 003480, JP2002 / 363010, JP2002 / 363170, WO91 / 00278, WO95 / 29168, WO95 / 3066 (WO 96 / 35679, WO 97 / 01541, WO 98 / 25909, WO 2001 / 034575, WO 2001 / 39597, WO 2001 / 85907, WO 2002 / 098227, WO 2002 / 098228, WO 2003 / 028462, WO 2003 / 028463, WO 2003 / 0284647, WO 2016 / 095768, and WO 2022 / 043205). However, the above-mentioned known aryluracils have many gaps in activity, especially in activity against monocotyledonous weeds. Similarly, many combinations of herbicidal active ingredients based on N-aryluracils have become known (cf. DE4437197, EP714602, WO96 / 07323, WO96 / 08151, JP11189506, JP2003 / 104808, JP2003 / 104809, JP2003 / 104810, JP2003 / 160415, and JP2003 / 160416). However, the properties of these combinations of active ingredients are not entirely satisfactory.

[0006] Furthermore, substituted uracils having N-linked, further substituted diaryl ether groups or corresponding heteroarylaryl ether radicals are also known (cf. US Pat. No. 6,333,296, US Pat. No. 6,121,201, WO 2001 / 85907, EP 1,122,244, EP 1,397,958, EP 1,422,227, WO 2002 / 098,227). Furthermore, highly substituted N-phenyluracils having specifically substituted carbonylalkyloxy groups have been described (cf. WO 2011 / 137088). WO 2018 / 019842 describes the use of specifically substituted N-phenyluracils to control specific dicotyledonous weeds that have specific resistance to established herbicides. Substituted 3-phenyl-5-alkyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-diones (cf. WO2019 / 101551) have likewise become known. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] EP1106607 [Patent Document 2] EP408382 [Patent Document 3] EP473551 [Patent Document 4] EP648749 [Patent Document 5] US4943309 [Patent Document 6] US5084084 [Patent Document 7] US5127935 [Patent Document 8] US6537948 [Patent Document 9] JP2001 / 348376 [Patent Document 10] JP2001 / 354661 [Patent Document 11] JP2002 / 003480 [Patent Document 12] JP2002 / 363010 [Patent Document 13] JP2002 / 363170 [Patent Document 14] WO91 / 00278 [Patent Document 15] WO95 / 29168 [Patent Document 16] WO95 / 30661 [Patent Document 17] WO96 / 35679 [Patent Document 18] WO97 / 01541 [Patent Document 19] WO98 / 25909 [Patent Document 20] WO2001 / 034575 [Patent Document 21] WO2001 / 39597 [Patent Document 22] WO2001 / 85907 [Patent Document 23] WO2002 / 098227 [Patent Document 24] WO2002 / 098228 [Patent Document 25] WO2003 / 028462 [Patent Document 26] WO2003 / 028463 [Patent Document 27] WO2003 / 0284647 [Patent Document 28] WO2016 / 095768 [Patent Document 29] WO2022 / 043205 [Patent Document 30] DE4437197 [Patent Document 31] EP714602 [Patent Document 32] WO96 / 07323 [Patent Document 33] WO96 / 08151 [Patent Document 34] JP11189506 [Patent Document 35] JP2003 / 104808 [Patent Document 36] JP2003 / 104809 [Patent Document 37] JP2003 / 104810 [Patent Document 38] JP2003 / 160415 [Patent Document 39] JP2003 / 160416 [Patent Document 40] US6333296 [Patent Document 41] US6121201 [Patent Document 42] WO2001 / 85907 [Patent Document 43] EP1122244 [Patent Document 44] EP1397958 [Patent Document 45] EP1422227 [Patent Document 46] WO2002 / 098227 [Patent Document 47] WO2011 / 137088 [Patent Document 48] WO2018 / 019842 [Patent Document 49] WO2019 / 101551 Summary of the Invention [Problem to be solved by the invention]

[0008] It has surprisingly been found that selected N-phenyluracils or salts thereof having a substituted alkyl ester side chain are suitable as herbicides and can be used with particular advantage to control monocotyledonous and dicotyledonous weeds in crop plant cultivation. [Means for solving the problem]

[0009] Therefore, the present invention provides a compound of general formula (I) [ka] [During the ceremony, R 1 is hydrogen, halogen, cyano, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-alkoxy or (C1-C8)-haloalkoxy; R 2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C1-C8)-alkoxy; R 3 is hydrogen, halogen or (C1-C8)-alkoxy; R 4 is halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C8)-haloalkyl or (C2-C8)-alkynyl; R 5 , R 6 and R 7 are independently hydrogen, halogen, cyano, (C-C)-alkyl, (C-C)-haloalkyl, (C-C)-alkoxy or (C-C)-haloalkoxy; G is unbranched or branched (C1-C8)-alkylene; Q is the formula [ka] is a radical represented by: R 8 is hydrogen, (C1-C8)-alkyl or cyano; R 9 is hydrogen or (C1-C8)-alkyl; R 10is (C3-C8)-cycloalkyl (which is unsubstituted or substituted in each case independently with an "m" radical selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, cyano and nitro), or spiro-(C5-C9)-alkanyl or dispiro-(C7-C8)-alkanyl, which is unsubstituted or substituted in each case independently by a radical "m" selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy and cyano; m is 0, 1, 2 or 3; and, X and Y are independently O (oxygen) or S (sulfur). The present invention provides a substituted N-phenyluracil represented by the following formula:

[0010] The present invention further preferably relates to a compound represented by general formula (I) R 1 is hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy or (C1-C6)-haloalkoxy; R 2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C1-C6)-alkoxy; R 3 is hydrogen, halogen or (C1-C6)-alkoxy; R 4 is halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C6)-haloalkyl or (C2-C6)-alkynyl; R 5 , R 6 and R 7are independently hydrogen, halogen, cyano, (C-C)-alkyl, (C-C)-haloalkyl, (C-C)-alkoxy or (C-C)-haloalkoxy; G is unbranched or branched (C1-C6)-alkylene; Q is the formula [ka] is a radical represented by: R 8 is hydrogen, (C1-C6)-alkyl or cyano; R 9 is hydrogen or (C1-C6)-alkyl; R 10 is (C3-C7)-cycloalkyl (which is unsubstituted or substituted in each case independently with an "m" radical selected from the group consisting of halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C6)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, cyano, nitro), or spiro-(C5-C7)-alkanyl or dispiro-(C7-C8)-alkanyl, which is unsubstituted or substituted in each case independently by an "m" radical selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy; m is 0, 1, 2 or 3; and, X and Y are independently O (oxygen) or S (sulfur). The present invention provides a compound represented by the formula:

[0011] The present invention very particularly preferably relates to compounds of the general formula (I), in which R 1is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl butyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy; R 2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, prop-1-yloxy, but-1-yloxy; R 3 is hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy; R 4 are fluorine, chlorine, bromine, cyano, NO2, C(O)NH2, C(S)NH2, trifluoromethyl, difluoromethyl, pentafluoroethyl, ethynyl, propyn-1-yl, 1-butyn-1-yl, pentyn-1-yl, hexyn-1-yl; R 5 , R 6and R 7 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1- ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy; G is methylene, (methyl)methylene, (ethyl)methylene, (prop-1-yl)methylene, (prop-2-yl)methylene, (but-1-yl)methylene, (but-2-yl)methylene, (pent-1-yl)methylene, (pent-2-yl)methylene, (pent-3-yl)methylene, (dimethyl)methylene, (diethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl propyl-1-ene, 3-methyl-propyl-1-ene, 1,1-dimethylethyl-1-ene, 2,2-dimethylethyl-1-ene, 1-ethylethyl-1-ene, 2-ethylethyl-1-ene, 1-(prop-1-yl)ethyl-1-ene, 2-(prop-1-yl)ethyl-1-ene, 1-(prop-2-yl)ethyl-1-ene, 2-(prop-2-yl)ethyl-1-ene, 1,1,2-trimethylethyl-1-ene, 1,2,2-trimethylethyl-1-ene, 1,1,2,2-tetramethylethyl-1- ene, n-pentylene, 1-methylbutyl-1-ene, 2-methylbutyl-1-ene, 3-methylbutyl-1-ene, 4-methylbutyl-1-ene, 1,1-dimethylpropyl-1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl-1-ene, 1,2-dimethylpropyl-1-ene, 1,3-dimethylpropyl-1-ene, 1-ethylpropyl-1-ene, n-hexylene, 1-methylpentyl-1-ene, 2-methylpentyl-1-ene, 3-methylpentyl-1-ene, 4-methylbutyl-1-ene ethylpentyl-1-ene, 1,1-dimethylbutyl-1-ene, 1,2-dimethylbutyl-1-ene, 1,3-dimethylbutyl-1-ene, 2,2-dimethylbutyl-1-ene, 2,3-dimethylbutyl-1-ene, 3,3-dimethylbutyl-1-ene, 1-ethylbutyl-1-ene, 2-ethylbutyl-1-ene, 1,1,2-trimethylpropyl-1-ene, 1,2,2-trimethylpropyl-1-ene, 1-ethyl-1-methylpropyl-1-ene, 1-ethyl-2-methylpropyl-1-ene; X and Y are independently O (oxygen) or S (sulfur); and, Q is a partial structure Q-1 to Q-25 specifically described below: [ka]

[0012] TIFF2025534472000006.tif68170, where the arrows in the structural formula in the table below represent the bond of each Q group to the carbonyl group in general formula (I). The present invention provides a compound represented by the formula:

[0013] The present invention particularly preferably relates to compounds of the general formula (I) R 1 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy; R 2 is hydrogen, fluorine or chlorine; R 3 is hydrogen, fluorine, chlorine, bromine or methoxy; R 4 is fluorine, chlorine, bromine, cyano, NO2, C(O)NH2, C(S)NH2, trifluoromethyl, ethynyl or propyn-1-yl; R 5 , R 6 and R 7 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, or trifluoromethoxy; G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, 1,1-dimethylethyl-1-ene, 2,2-dimethylethyl-1-ene, 1-ethylethyl-1-ene, 2-ethylethyl-1-ene, 1-(prop-1-yl)ethyl-1-ene, 2-(prop-1-yl) ethyl-1-ene, 1-(prop-2-yl)ethyl-1-ene, 2-(prop-2-yl)ethyl-1-ene, n-pentylene, 1-methylbutyl-1-ene, 2-methylbutyl-1-ene, 3-methylbutyl-1-ene, 4-methylbutyl-1-ene, 1,1-dimethylpropyl-1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl-1-ene, 1,2-dimethylpropyl-1-ene, 1,3-dimethylpropyl-1-ene, 1-ethylpropyl-1-ene or n-hexylene; X and Y are independently O (oxygen) or S (sulfur); and, Q is one of the partial structures Q-1 to Q-25 specifically described above. The present invention provides a compound represented by the formula:

[0014] The present invention very particularly preferably relates to compounds of the general formula (I), in which R 1 is hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy; R 2 is fluorine; R 3 is fluorine; R 4 is chlorine, bromine, cyano, NO2, C(O)NH2 or C(S)NH2; R 5 , R 6 and R 7 are independently hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, or trifluoromethoxy; G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, n-pentylene or n-hexylene; X and Y are independently O (oxygen) or S (sulfur); and, Q is one of the partial structures Q-1 to Q-25 specifically described above. The present invention provides a compound represented by the formula:

[0015] The present invention particularly particularly preferably relates to compounds of the general formula (I) R 1 is hydrogen, fluorine, chlorine or bromine; R 2 is fluorine; R 3 is fluorine; R 4 is chlorine, bromine, cyano or NO2; R 5 is hydrogen, fluorine, chlorine or bromine; R 6 is hydrogen, fluorine, chlorine, bromine or cyano; R 7 is hydrogen, fluorine, chlorine or bromine; G is methylene, (methyl)methylene or (ethyl)methylene; X and Y are independently O (oxygen) or S (sulfur); and, Q is one of the partial structures Q-1 to Q-25 specifically described above. The present invention provides a compound represented by the formula:

[0016] The present invention very particularly preferably relates to compounds of the general formula (I), in which R 1 is hydrogen; R 2 is fluorine; R 3 is fluorine; R 4 is chlorine, bromine, cyano or NO2; R 5 is hydrogen; R 6 is hydrogen, fluorine, chlorine, bromine or cyano; R 7 is hydrogen; G is methylene or (methyl)methylene; X is O (oxygen) or S (sulfur); Y is O (oxygen); and, Q is one of the partial structures Q-1 to Q-25 specifically described above. The present invention provides a compound represented by the formula:

[0017] The present invention very particularly preferably relates to compounds of the general formula (I), in which R 1 is hydrogen; R 2 is fluorine; R 3 is fluorine; R 4 is chlorine, bromine, cyano or NO2; R 5 is hydrogen; R 6 are hydrogen, fluorine, and chlorine; R 7 is hydrogen; G is methylene, (methyl)methylene; X is O (oxygen) or S (sulfur); Y is O (oxygen); and, Q is one of the partial structures Q-1 to Q-25 specifically described above. The present invention provides a compound represented by the formula:

[0018] The present invention very particularly preferably relates to compounds of the general formula (I), in which R 1is hydrogen; R 2 is fluorine; R 3 is fluorine; R 4 is chlorine, bromine or cyano; R 5 is hydrogen; R 6 is hydrogen or fluorine; R 7 is hydrogen; G is methylene; X is O (oxygen); Y is O (oxygen); and, Q is one of the substructures Q-1, Q-2, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-12, Q-13, Q-14, Q-15, Q-16, Q-18 or Q-19 specifically described above. The present invention provides a compound represented by the formula:

[0019] The general or preferred definitions of radicals given above apply both to the final product of general formula (I) and, correspondingly, to the starting materials or intermediates required in each case to prepare said final product. These radical definitions can be combined with one another as necessary, i.e., encompass combinations between the given preferred ranges.

[0020] Of particular interest are the compounds of the invention of the general formula (I) described above, in which the individual radicals have one of the preferred meanings specified above or below, or in particular one or more of the preferred meanings specified above or below, in combination, or their salts, or their use according to the invention, primarily because they have a higher herbicidal activity, better selectivity and / or better preparability.

[0021] If the compound can form tautomers through hydrogen shifting whose structures would not formally be encompassed by general formula (I), those tautomers are nevertheless encompassed within the definition of the compounds of the present invention represented by general formula (I), unless a specific tautomer is being considered. For example, many types of carbonyl compounds can exist in both keto and enol forms, where both forms are encompassed within the definition of the compounds of general formula (I).

[0022] Depending on the type of substituents and the way they are attached, the compounds of general formula (I) may exist as stereoisomers. All possible stereoisomers (e.g., enantiomers, diastereomers, Z and E isomers) defined by their specific three-dimensional configurations 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 determine the enantiomeric or diastereomeric excess, or on a preparative scale to prepare test samples for biological testing. It is also possible to selectively prepare stereoisomers by using stereoselective reactions with optically active starting materials and / or auxiliaries. Thus, the present invention also relates to all stereoisomers and mixtures thereof which are encompassed by general formula (I) but not shown in their specific stereoisomeric form.

[0023] If the compounds are obtained as solids, their purification can also be carried out by recrystallization or digestion. If the individual compounds (I) cannot be obtained satisfactorily by the routes described below, they can be prepared by derivatizing another compound (I).

[0024] Suitable isolation, purification and separation methods for the stereoisomers of the compounds of formula (I) are generally known to those skilled in the art from similar cases, such as physical processes, such as crystallization, chromatographic methods, in particular column chromatography and HPLC (high pressure liquid chromatography), distillation (optionally under reduced pressure), extraction and other methods, and any remaining mixtures can generally be separated by chromatographic separation, for example, chromatographic separation on chiral solid phases. Suitable for preparative or industrial scale are methods such as crystallization of diastereomeric salts, which can be obtained from the diastereomeric mixture using an optically active acid and, where appropriate, an optically active base in the presence of an acidic group.

[0025] The terms used above and below with respect to the compounds of the present invention are explained below and are well known to those skilled in the art and have the definitions, in particular, as explained below.

[0026] Unless defined otherwise, names of chemical groups are generally understood in such a way that the bond to the backbone or the rest of the molecule is via the last-mentioned structural element of the chemical group, i.e., via the oxygen atom in the case of (C-C)-alkenyloxy, and in the case of heterocyclyl-(C-C)-alkyl or (C-C)-alkoxy-(C-C)-alkoxy-(C-C)-alkyl, in each case via a carbon atom of the alkyl group.

[0027] According to the present invention, "alkylthio", alone or as part of a chemical group, denotes a straight or branched chain S-alkyl, preferably a straight or branched chain S-alkyl having 1 to 8 or 1 to 6 carbon atoms, such as (C1-C 10)-, (C1-C6)- or (C1-C4)-alkylthio, for example (but not limited to), (C1-C6)-alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexyl Examples of the methyl butylthio include butylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio.

[0028] "Alkoxy" means an alkyl radical attached through an oxygen atom, including but not limited to, (C1-C6)-alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy , hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy. Alkenyloxy means an alkenyl radical attached through an oxygen atom, and alkynyloxy means an alkynyl radical attached through an oxygen atom, such as (C-C 10 )-, (C2-C6)- or (C2-C4)-alkeneoxy, and (C3-C 10 )-, (C3-C6)- or (C3-C4)-alkynoxy.

[0029] According to the present invention, "alkylcarbonyl" (alkyl-C(=O)-), unless defined differently elsewhere, denotes an alkyl radical attached to the backbone via -C(=O)-, e.g., (C-C 10 )-, (C1-C6)- or (C1-C4)-alkylcarbonyl, where the number of carbon atoms refers to the alkyl radical in the alkylcarbonyl group.

[0030] "Alkoxycarbonyl (alkyl-OC(=O)-)" means, unless defined differently elsewhere: an alkyl radical attached to a backbone via -OC(=O)-, e.g., (C-C10 )-, (C1-C6)- or (C1-C4)-alkoxycarbonyl, where the number of carbon atoms refers to the alkyl radical in the alkoxycarbonyl group. Similarly, "alkenyloxycarbonyl" and "alkynyloxycarbonyl", unless defined differently elsewhere, are, according to the present invention, alkenyl and alkynyl radicals, respectively, attached to the backbone via -OC(=O)-, e.g., (C2-C 10 )-, (C2-C6)- or (C2-C4)-alkenyloxycarbonyl, or (C3-C 10 )-, (C3-C6)- or (C3-C4)-alkynyloxycarbonyl, where the number of carbon atoms refers to the alkenyl or alkynyl radical in the alkenyloxycarbonyl or alkynyloxycarbonyl group.

[0031] According to the present invention, the term "alkylcarbonyloxy" (alkyl-C(=O)-O-), unless defined differently elsewhere, denotes an alkyl radical attached to the backbone via the oxygen of the carbonyloxy group (-C(=O)-O-), e.g., (C-C 10 )-, (C1-C6)- or (C1-C4)-alkylcarbonyloxy, where the number of carbon atoms refers to the alkyl radical in the alkylcarbonyloxy group.

[0032] For example, C(O)R 13 , C(O)OR 13 , OC(O)NR 11 R 12 or C(O)NR 11 R 12 In the shortened forms such as, the shortened form O shown in parentheses is an oxygen atom attached to the adjacent carbon atom by a double bond.

[0033] OC(S)OR 13 ,OC(S)SR 14 , OC(S)NR 11 R 12In the abbreviations S shown in parentheses, the abbreviation S is a sulfur atom attached to the adjacent carbon atom by a double bond.

[0034] The term "aryl" means an optionally substituted monocyclic, bicyclic or polycyclic aromatic system having 6 to 14 (particularly 6 to 10) ring carbon atoms, such as phenyl, naphthyl, anthryl, phenanthrenyl, etc., preferably phenyl.

[0035] The term "optionally substituted aryl" also encompasses polycyclic ring systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, etc., where the bonding position is on the aromatic ring system. In systematic terms, "aryl" is also generally encompassed by the term "optionally substituted phenyl". Here, preferred substituents for aryl include, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bisalkylaminoalkoxy, tris[alkyl]silyl, bis[alkyl]arylsilyl, bis[alkyl]arylsilyl, bis[alkyl]aminoalkoxy, bis[alkyl]aminoalkoxy, bis[alkyl]aminosilyl ... [alkyl]alkylsilyl, tris[alkyl]silylalkynyl, arylalkynyl, heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bisalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, bisalkylaminocarbonyl, heteroarylalkoxy, arylalkoxy, and the like.

[0036] Heterocyclic radicals (heterocyclyl) contain at least one heterocyclic ring (= a carbocyclic ring in which at least one carbon atom is replaced by a heteroatom, preferably a heteroatom selected from the group N, O, S, P), which may be saturated, unsaturated, partially saturated or aromatic and may be unsubstituted or substituted, in which case the bonding point is located on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it may be fused to another carbocyclic or heterocyclic ring. In the case of optionally substituted heterocyclyl, polycyclic systems also include, for example, 8-azabicyclo[3.2.1]octanyl, 8-azabicyclo[2.2.2]octanyl or 1-azabicyclo[2.2.1]heptyl. In the case of an optionally substituted heterocyclyl, spirocyclic systems such as 1-oxa-5-azaspiro[2.3]hexyl are also encompassed. Unless otherwise defined, the heterocyclic ring preferably contains 3 to 9 ring atoms (particularly 3 to 6 ring atoms) and one or more (preferably 1 to 4, particularly 1, 2 or 3) heteroatoms (preferably heteroatoms selected from the group consisting of N, O and S) in the heterocyclic ring (wherein, however, two oxygen atoms must not be directly adjacent to each other), for example, one heteroatom selected from the group consisting of N, O and S, and is exemplified by 1-, 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or -3-yl, 2,3-dihydro-1H-pyrrol-1- or -2- or -3-yl. or -4- or -5-yl; 2,5-dihydro-1H-pyrrol-1- or -2- or -3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or -3- or -4- or -5-yl or -6-yl; 1,2,3,6-tetrahydropyridin-1- or -2- or -3- or -4- or -5- or -6-yl; 1,2,3,4-tetrahydropyridin-1- or -2- or -3- or -4- or -5- or -6-yl; 1,4-dihydropyridin-1- or -2- or -3- or -4-yl; 2,3-dihydropyridin-2- or -3- or -4- or -5- or -6-yl;2,5-Dihydropyridin-2- or -3- or -4- or -5- or -6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-1H-azepin-1- or -2- or -3- or -4-yl; 3,4,5,6-tetrahydro-2H-azepin-2- or -3- or - 4- or -5- or -6- or -7-yl; 4,5-dihydro-1H-azepin-1- or -2- or -3- or -4-yl; 2,5-dihydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,7-dihydro-1H-azepin-1- or -2- or -3- or -4-yl; 2,3-dihydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 3,4-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 3,6-di Hydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 5,6-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-3H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 3H-azepin-2- or -3- or -4- or -5- or -6- or - 7-yl; 4H-azepine-2- or -3- or -4- or -5- or -6- or -7-yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or -3- or -4- or -5-yl; 2,5-dihydrofuran-2- or -3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl;2H-pyran-2- or -3- or -4- or -5- or -6-yl; 4H-pyran-2- or -3- or -4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydrooxepin-2- or -3- or -4-yl; 2,3-dihydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydrooxepin-2- or -3- or -4-yl; 2,5-dihydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl; oxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophen-2- or -3- or -4- or -5-yl; 2,5-dihydrothiophen-2- or -3-yl; tetrahydro-2H-thiopyran-2- or -3- or -4-yl; 3,4-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 4H-thiopyran-2- or -3- or -4-yl. Preferred 3- and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1-, 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxetan-2-yl, and the like. Further examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic radicals having two heteroatoms selected from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazol-1- or 2- or 3- or 4-yl;2,5-Dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; 4,5-Dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; Hexahydropyridazin-1- or 2- or 3- or 4-yl; 1,2,3,4-Tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-Tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-Tetrahydropyridazin-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-Tetrahydropyridazin Hydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazin-3- or 4-yl; 1,6-dihydropyridazin-1- or 3- or 4- or 5- or 6-yl; hexahydropyrimidin-1- or 2- or 3- or 4-yl; 1,4,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl 1,2,3,4-tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidin-2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or 6-yl; 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-tetrahydropyrazine-1 - or 2- or 3- or 5- or 6-yl; 1,2,3,4-tetrahydropyrazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazin-1- or 2- or 3-yl; 2,3-dihydropyrazin-2- or 3- or 5- or 6-yl; 2,5-dihydropyrazin-2- or 3-yl; 1,3-dioxolan-2- or 4- or 5-yl; 1,3-dioxol-2- or 4-yl; 1,3-dioxan-2- or 4- or 5-yl;4H-1,3-dioxin-2- or 4- or 5- or 6-yl; 1,4-dioxan-2- or 3- or 5- or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; 1,4-dioxin-2- or 3-yl; 1,2-dithiolan-3- or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl; 1,3-dithiolan-2- or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3- or 4-yl; 3,4-dihydro-1,2-dithiin-3- or 4- or 5- 6-yl; 3,6-dihydro-1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl; 1,3-dithian-2- or 4- or 5-yl; 4H-1,3-dithiin-2- or 4- or 5- or 6-yl; isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisoxazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisoxazol-3- or 4- or 5-yl; 1,3-oxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 1,2-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro -2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-1,2-oxazin-3- or 4- or 5- or 6-yl; 4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 1,3-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl;3,6-Dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-oxazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-oxazin-2- or 4- or 5- or 6-yl; 2H-1,3-oxazin-2- or 4- or 5- or 6-yl; 6H-1,3-oxazin-2- or 4- or 5- or 6-yl; 4H-1,3-oxazin-2- or 4- or; 5- or 6-yl;morpholin-2- or 3- or 4-yl;3,4-dihydro-2H-1,4-oxazin-2- or 3- or 4- or 5- or 6-yl;3,6-dihydro-2H-1,4-oxazin-2- or 3- or 5- or 6-yl;2H-1,4-oxazin-2- or 3- or 5- or 6-yl;4H-1,4-oxazin-2- or 3-yl;1,2-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl;2,3,4,5-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 1,2-oxazepin-3- or 4- or 5- or 6 - or 7-yl; 1,3-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;4,5,6,7-Tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,3-Dihydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-Dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-Dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5-Dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-Dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,7-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro -1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazol-2- or 3- or 4- or 5-yl;4,5-Dihydroisothiazol-3- or 4- or 5-yl; 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-Dihydro-1,3-thiazol-2- or 3- or 4- or 5-yl; 2,5-Dihydro-1,3-thiazol-2- or 4- or 5-yl; 4,5-Dihydro-1,3-thiazol-2- or 4- or 5-yl; 1,3-Thiazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-Dihydro-2H-1,3-thiazin-2- or 3- or 4- or is 5- or 6-yl; 3,6-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-thiazin-2- or 4- or 5- or 6-yl; 2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 6H-1,3-thiazin-2- or 4- or 5- or 6-yl; 4H-1,3-thiazin-2- or 4- or 5- or 6-yl, and the like. Further examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic radicals having three heteroatoms selected from the group N, O and S, such as 1,4,2-dioxazolidin-2- or -3- or -5-yl; 1,4,2-dioxazol-3- or -5-yl; 1,4,2-dioxazinan-2- or -3- or -5- or -6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or -5- or -6-yl; 1,4,2-dioxazin-3- or -5- or -6-yl; 1,4,2-dioxazepan-2- or - 3- or -5- or -6- or -7-yl; 6,7-dihydro-5H-1,4,2-dioxazepin-3- or -5- or -6- or -7-yl; 2,3-dihydro-7H-1,4,2-dioxazepin-2- or -3- or -5- or -6- or -7-yl; 2,3-dihydro-5H-1,4,2-dioxazepin-2- or -3- or -5- or -6- or -7-yl; 5H-1,4,2-dioxazepin-3- or -5- or -6- or -7-yl; 7H-1,4,2-dioxazepin-3- or -5- or -6- or -7-yl, etc. Examples of optionally substituted heterocyclic structures are also described below: [ka]

[0037] TIFF2025534472000008.tif236159

[0038] TIFF2025534472000009.tif142159

[0039] The heterocycles mentioned above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, halo and substituted by alkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, heteroaryloxy, bisalkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, or arylalkoxycarbonylalkylaminocarbonyl.

[0040] If a substructure is substituted "with one or more radicals" selected from a list of radicals (= groups) or a generically defined group of radicals, this in each case includes simultaneous substitution with several identical and / or structurally different radicals.

[0041] If it is a partially saturated or fully saturated nitrogen heterocycle, it may be attached to the rest of the molecule through a carbon or through a nitrogen.

[0042] Suitable substituents for substituted heterocyclic radicals are those further specified below, as well as oxo and thioxo. An oxo group as a substituent on a ring carbon atom is, for example, a carbonyl group in the heterocyclic ring. As a result, lactones and lactams are also preferably included. The oxo group can also be present on a ring heteroatom, where the ring heteroatom, for example, in the case of N and S, can exist in various oxidation states, and in this case, they form, for example, divalent groups -N(O)-, -S(O)- (also abbreviated as "SO") and -S(O)2- (also abbreviated as "SO2") in the heterocyclic ring. In the case of -N(O)- and -S(O)- groups, both enantiomers are included in each case.

[0043] According to the present invention, the expression "heteroaryl" refers to heteroaromatic compounds, i.e., fully unsaturated aromatic heterocyclic compounds, preferably 5- to 7-membered rings having 1 to 4 (preferably 1 or 2) identical or different heteroatoms (preferably O, S or N). Heteroaryl according to the present invention includes, 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-triazol-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 azepinyl, 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-triazol-2-yl, pyridin ... 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, etc. Heteroaryl groups according to the present invention may also be substituted with one or more identical or different radicals. If two adjacent carbon atoms are part of a further aromatic ring, the system is a fused heteroaromatic system, for example a benzofused heteroaromatic compound or a polyannelated heteroaromatic compound. Preferred examples include quinolines (e.g., quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); isoquinolines (e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine, phthalazine, pyridopyrazines, pyridopyrimidines, pyridopyridazines, pteridines, pyrimidopyrimidines. Examples of heteroaryl 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-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-benzoxazol-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,A 5- or 6-membered benzo-fused ring selected from the group consisting of 2-benzisoxazol-5-yl, 1,2-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, and 1,2-benzisothiazol-7-yl.

[0044] The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. When the term is used in reference to a radical, "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom.

[0045] According to the present invention, "alkyl" refers to a linear or branched open-chain saturated hydrocarbon radical which may be mono- or polysubstituted, the latter being referred to as "substituted alkyl". Preferred substituents are halogen atoms, alkoxy groups, haloalkoxy groups, cyano groups, alkylthio groups, haloalkylthio groups, amino groups or nitro groups, with methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine being particularly preferred. The prefix "bis" also includes combinations of different alkyl radicals, such as methyl (ethyl) or ethyl (methyl).

[0046] "Haloalkyl", "haloalkenyl" and "haloalkynyl" mean alkyl, alkenyl and alkynyl, respectively, that are partially or fully substituted with the same or different halogen atoms, e.g., monohaloalkyl, e.g., CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, CH2F; perhaloalkyl, e.g., CCl3, CClF2, CFCl2, CF2CClF2, CF2CClFCF3; polyhaloalkyl, e.g., CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3, etc.; the term "perhaloalkyl" also encompasses the term "perfluoroalkyl".

[0047] "Haloalkoxy" includes, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3, and OCH2CH2Cl; this applies correspondingly to haloalkenyl and other halogen-substituted radicals.

[0048] The expression "(C1-C4)-alkyl" given herein as an example is a shorthand notation for a straight-chain or branched-chain alkyl having 1 to 4 carbon atoms, with the range indicated 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 larger range of carbon atoms specified, such as "(C1-C6)-alkyl", also include correspondingly straight-chain or branched-chain alkyl radicals having a larger number of carbon atoms (i.e., following the above example, alkyl radicals having 5 and 6 carbon atoms).

[0049] Unless otherwise specified, for hydrocarbon radicals such as alkyl, alkenyl, and alkynyl radicals (including hydrocarbon radicals in complex radicals), a lower carbon skeleton, e.g., a lower carbon skeleton having 1 to 6 carbon atoms, or, in the case of unsaturated groups, a lower carbon skeleton having 2 to 6 carbon atoms, is preferred. Alkyl radicals (including alkyl radicals in complex radicals such as alkoxy and haloalkyl) are, for example, methyl, ethyl, n-propyl or i-propyl, n-butyl, i-butyl, t-butyl or 2-butyl, pentyls, hexyls (e.g., n-hexyl, i-hexyl, and 1,3-dimethylbutyl), heptyls (e.g., n-heptyl, 1-methylhexyl, and 1,4-dimethylpentyl); alkenyl and alkynyl radicals are defined as possible unsaturated radicals corresponding to the alkyl radical (wherein at least one double or triple bond is present). Radicals having one double or triple bond are preferred.

[0050] The term "alkenyl" specifically includes straight- or branched-chain open-chain hydrocarbon radicals having two or more double bonds (e.g., 1,3-butadienyl and 1,4-pentadienyl), as well as allenyl or cumulenyl radicals having one or more cumulative double bonds (e.g., allenyl (1,2-propadienyl), 1,2-butadienyl, and 1,2,3-pentatrienyl). Alkenyl includes, for example, vinyl optionally substituted with further alkyl radicals, such as (C2-C6)-alkenyl, for example (but not limited to), ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl. , 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl nyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl.

[0051] The term "alkynyl" also specifically includes straight or branched open-chain hydrocarbon radicals having two or more triple bonds or having one or more triple bonds and one or more double bonds (e.g., 1,3-butatrienyl or 3-penten-1-yn-1-yl). (C2-C6)-alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2-propynyl.

[0052] The term "cycloalkyl" refers to a carbocyclic saturated ring system, preferably one having 3 to 8 ring carbon atoms (e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl), which may be further substituted, preferably with hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, or cycloalkylaminocarbonyl. Optionally substituted cycloalkyl also encompasses ring systems having substituents, including those containing a substituent having a double bond on the cycloalkyl radical (e.g., an alkylidene group, e.g., methylidene). In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems such as, for example, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl Bicycloalkyl groups include bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl, and adamantan-2-yl, and also include systems such as 1,1'-bi(cyclopropyl)-1-yl, 1,1'-bi(cyclopropyl)-2-yl, etc. The term "(C3-C7)-cycloalkyl" is a shorthand notation for cycloalkyl having 3 to 7 carbon atoms, corresponding to the specified range for carbon atoms.

[0053] In the case of spiro-(C5-C9)-alkanyl, spirocyclic aliphatic systems such as spiro[2.2]pentan-1-yl, spiro[2.2]pentan-2-yl, spiro[2.3]hexan-1-yl, spiro[2.3]hexan-2-yl, spiro[2.3]hexan-4-yl, spiro[2.3]hexan-5-yl, spiro[3.3]heptan-1-yl, spiro[3.3]heptan-2-yl are also encompassed.

[0054] In the case of dispiro-(C7-C8)-alkanyl, dispirocycloaliphatic systems, e.g., dispiro[2.0.2 4 .1 3 ]heptan-7-yl, dispiro[2.0.2 4 .1 3 ]heptan-1-yl, dispiro[2.0.2 4 .2 3 ]octan-7-yl, dispiro[2.0.2 4 .2 3 ]octan-1-yl, dispiro[2.0.3 4 .1 3 ]octan-1-yl, dispiro[2.0.3 4 .1 3 ]octan-8-yl, dispiro[2.0.3 4 .1 3 ]octan-5-yl, dispiro[2.0.3 4 .1 3 ]octan-8-yl, dispiro[2.0.3 4 .1 3 ]octan-6-yl, dispiro[2.1.2 5 .1 3 ]octan-4-yl, dispiro[2.1.2 5 .1 3 ]octan-4-yl, dispiro[2.1.2 5 .1 3 ]octan-1-yl is also encompassed.

[0055] "Cycloalkenyl" refers to a carbocyclic non-aromatic partially unsaturated ring system, preferably a carbocyclic non-aromatic partially unsaturated ring system having 4 to 8 carbon atoms, such as 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl, or 1,4-cyclohexadienyl, and also refers to a carbocyclic non-aromatic partially unsaturated ring system containing a substituent having a double bond on the cycloalkenyl radical (e.g., an alkylidene group, e.g., methylidene). In the case of optionally substituted cycloalkenyl, the remarks regarding substituted cycloalkyl apply correspondingly.

[0056] The term "alkylidene" refers to a group such as (C-C 10 "Alkylidene," in the form )-alkylidene, refers to a radical of a straight or branched open-chain hydrocarbon radical bonded through a double bond. The possible bonding positions for an alkylidene are necessarily only those positions on the substructure where two hydrogen atoms can be replaced by a double bond; such radicals are, for example, =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5, or =C(C2H5)-C2H5. Cycloalkylidene refers to a carbocyclic radical bonded through a double bond.

[0057] The term "alkylene," e.g., in the form (C1-C8)-alkylene, refers to a radical of a straight or branched open chain hydrocarbon radical, in which the radical is attached at two positions to further groups.

[0058] "Alkoxyalkyl" refers to an alkoxy radical attached through an alkyl group, and "alkoxyalkoxy" means an alkoxyalkyl radical attached through an oxygen atom, such as (but not limited to), methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy, and the like.

[0059] "Arylalkyl" refers to an aryl radical bonded through an alkyl group, "heteroarylalkyl" means a heteroaryl radical bonded through an alkyl group, and "heterocyclylalkyl" means a heterocyclyl radical bonded through an alkyl group.

[0060] "Cycloalkylalkyl" refers to a cycloalkyl radical attached through an alkyl group, such as (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl, and the like.

[0061] "Arylalkenyl" refers to an aryl radical bonded through an alkenyl group, "heteroarylalkenyl" means a heteroaryl radical bonded through an alkenyl group, and "heterocyclylalkenyl" means a heterocyclyl radical bonded through an alkenyl group.

[0062] "Arylalkynyl" refers to an aryl radical bonded through an alkynyl group, "heteroarylalkynyl" means a heteroaryl radical bonded through an alkynyl group, and "heterocyclylalkynyl" means a heterocyclyl radical bonded through an alkynyl group.

[0063] According to the present invention, "haloalkylthio", alone or as a component of a chemical group, is a straight or branched chain S-haloalkyl, preferably a straight or branched chain S-haloalkyl having 1 to 8 or 1 to 6 carbon atoms, such as (C-C)-, (C-C)- or (C-C)-haloalkylthio, such as (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio, and the like.

[0064] "Halocycloalkyl" and "halocycloalkenyl" mean cycloalkyl or cycloalkenyl, respectively, that are partially or fully substituted with the same or different halogen atoms (e.g., F, Cl, and Br) or with haloalkyl (e.g., trifluoromethyl or difluoromethyl), such as 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclobut-1-yl, 1-trifluoromethylcycloprop-1-yl, 2-trifluoromethylcycloprop-1-yl, 1-chlorocycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl, and the like.

[0065] Synthesis of substituted N-phenyluracils represented by general formula (I) The substituted N-phenyluracils of the general formula (I) according to the present invention can be synthesized using known processes. The synthetic routes used and investigated start from commercially available or easily prepared heteroaromatic amines and the corresponding substituted hydroxyesters. In the following scheme, the partial structures G, Q, R of the general formula (I) are 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7X and Y have the above-defined meanings unless otherwise provided, which are illustrative but non-limiting. Mercaptophenyl-1H-pyrimidine-2,4-dione (which may be further substituted) is prepared as the first key intermediate for synthesizing the compounds of the present invention represented by general formula (I) (wherein X is sulfur (S) and Y is oxygen (O)). For example, but not by way of limitation, this is illustrated by the synthesis of 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (IIa) (Scheme 1). For this purpose, a suitable substituted aniline (such as, but not limited to, 2-fluoro-4-chloroaniline) is converted to the corresponding isocyanate using a suitable reagent (e.g., triphosgene) in a suitable polar aprotic solvent (e.g., dichloromethane), which in a next step is converted to the corresponding, optionally further substituted, pyrimidine-2,4-dione (such as, but not limited to, 3-(4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione) by reaction with a suitable aminoacrylate using a suitable base (e.g., sodium hydride or potassium tert-butoxide) in a suitable polar aprotic solvent (e.g., N,N-dimethylformamide) (Scheme 1). Subsequently, sulfochlorination using a suitable reagent (e.g., chlorosulfonic acid) followed by reduction using a suitable reducing agent (e.g., Zn in ethanol and HCl, tin(II) chloride hydrate, or triphenylphosphine) can be used to prepare the desired mercaptophenyl-1H-pyrimidine-2,4-dione (e.g., but not limited to, 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (IIa)) (cf. KR1345394; EP1122244; EP408382; WO 2003 / 029226; WO2010 / 038953; US2011 / 0224083; KR2011 / 110420). In Scheme 1 below, R 2 and R 3is, for example, but not limited to, fluorine, and R 4 is, for example, but not limited to, chlorine, and X is, for example, but not limited to, sulfur.

[0066] Scheme 1 [ka]

[0067] The synthesis of key intermediate (IIa) described in Scheme 1 can also be applied to the preparation of similar intermediates. Each further substituted N-methyl-5-mercaptophenyl-1H-pyrimidine-2,4-dione intermediate (II) can then be converted to the desired compound of the present invention represented by general formula (Ia) (wherein X is sulfur (S) and Y is oxygen (O)) by various routes (Scheme 2), after converting compound (II) in a first step to intermediate (III) using a suitable base in a suitable polar aprotic solvent (e.g., dioxane) or using a suitable transition metal catalyst (e.g., tris(dibenzylideneacetone)dipalladium(0)) with a suitable ligand (e.g., 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene) in conjunction with a suitable base (e.g., diisopropyl(ethyl)amine) and an appropriate optionally further substituted iodophenol (Scheme 2). In Scheme 2 below, Q, R 2 , R 3 and R 4 has the above meaning according to the present invention. 1 , R 5 , R 6 , R 7is, for example, but not limited to, hydrogen, X is, for example, but not limited to, sulfur, Y is, for example, but not limited to, oxygen, and G is, for example, but not limited to, CH. The corresponding intermediate (III) shown as a non-limiting example in Scheme 2 can be converted to the corresponding oxyalkanoate intermediate (IVa, IVb) or the desired target compound represented by general formula (Ia) by reacting it with an appropriate optionally further substituted iodoalkanoate (for example, but not limited to, iodoacetate in Scheme 3) using an appropriate base (for example, silver carbonate (I)) in a suitable polar aprotic solvent (for example, n-hexane or cyclohexane) at elevated temperature (for example, under microwave conditions) (cf. Synthesis 2009, 2725). The corresponding iodoalkanoates can be prepared by routes known from the literature (cf. Eur. J. Org. Chem., 2006, 71, 8459; WO2012 / 037573; Organometallics, 2009, 28, 132).

[0068] Scheme 2 [ka]

[0069] The ethyl ester intermediate (IVa) and the tert-butyl ester intermediate (IVb) can then be converted to the corresponding free acid (V) under appropriate reaction conditions (using an acid such as hydrochloric acid or acetic acid in the case of (IVa), or trifluoroacetic acid (TFA) in the case of (IVb)). The desired substituted N-phenyluracil represented by general formula (Ia) can be prepared by reacting the corresponding acid intermediate (V) with an appropriate compound QH in the presence of a suitable coupling agent (e.g., HOBt = 1-hydroxybenzotriazole, EDC = 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, HATU = O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, T3P = 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane 2,4,6-trioxide) and a suitable base (e.g., diisopropylethylamine, triethylamine) in a suitable polar aprotic solvent (e.g., dichloromethane, chloroform). Alternatively, the ethyl ester (IVa) can be converted to the corresponding desired substituted N-phenyluracil of general formula (Ia) by coupling with a suitable compound QH in the presence of a suitable Lewis acid (e.g., indium(III) chloride) (cf. WO2011 / 1307088).

[0070] The preparation of compounds of general formula (I) where X and Y are, for example, but not limited to, oxygen (O) proceeds via the synthesis of a key intermediate (VI) bearing a fluorine substituent at the 5-position (e.g., 3-(2,5-difluoro-4-nitro)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (VIa)). For this purpose, a suitable substituted aniline (such as, but not limited to, 2,5-difluoroaniline) is converted to the corresponding isocyanate using a suitable reagent (e.g., triphosgene) in a suitable polar aprotic solvent (e.g., dichloromethane), which is then converted in a next step to the corresponding, optionally further substituted, pyrimidine-2,4-dione (such as, but not limited to, 3-(2,5-difluorophenyl)-6-trifluoromethyl-1H-pyrimidine-2,4-dione) by reaction with a suitable aminoacrylate using a suitable base (e.g., sodium hydride or potassium tert-butoxide) in a suitable polar aprotic solvent (e.g., N,N-dimethylformamide) (Scheme 3). Nitration with an appropriate nitrating reagent followed by N-methylation with an appropriate methylating reagent provides the desired intermediate (for example, but not limited to, 3-(2,5-difluoro-4-nitro)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (VIa)). In Scheme 3 below, R 2 and R 3 is, for example, but not limited to, fluorine, and R 4 is, for example, but not limited to, nitro.

[0071] Scheme 3 [ka]

[0072] The intermediate (VI) obtained by the above method (e.g., compound (VIa)) can then be converted to the desired substituted N-phenyluracil (Ib, R 4 = nitro). The intermediate (VII) used for this purpose can be obtained by starting from commercially available 1-chloro-2-nitrobenzene and reacting it with a suitable substituted hydroxyalkylcarbonyl reagent (e.g., using sodium hydride) in a suitable polar aprotic solvent (e.g., tetrahydrofuran or dioxane) via base-mediated coupling or by reaction of 2-nitrophenol with a suitable substituted chloromethylcarbonyl reagent; (ii) reduction of the nitro group using a suitable reducing agent (e.g., hydrogen, palladium on carbon in a suitable polar protic solvent); (iii) diazotization (in a suitable polar aprotic solvent (e.g., dichloromethane (DCM), dimethoxyethane) The nitro group in compound (Ib) can then be converted to a halogen substituent (e.g., chlorine, bromine) by reduction followed by a Sandmeyer reaction, thereby affording the desired substituted N-phenyluracil (Ic). In Scheme 4 below, Q and R 2 has the above meaning according to the present invention. 3 is, for example, but not limited to, fluorine, and R 4 is, for example, but not limited to, chlorine or nitro, and R 1 , R 5 , R 6 , R 7is, for example, but not limited to, hydrogen, X and Y are, for example, but not limited to, oxygen, and G is, for example, but not limited to, CH.

[0073] Scheme 4 [ka]

[0074] The intermediate (VI) obtained by the above method can be converted to the desired substituted N-phenyluracil (Id, R 4 = nitro) (where X = O (oxygen) and Y = S (sulfur)). The intermediate (VIII) used for this purpose can be prepared by a multi-step synthesis similar to the synthesis of intermediate (VII) described in Scheme 4, starting from commercially available 1-chloro-2-nitrobenzene or 2-nitrothiophenol. The nitro group in compound (Id) can then be converted to a halogen substituent (e.g., chlorine, bromine) by reduction followed by a Sandmeyer reaction, thereby providing the desired substituted N-phenyluracil (Ie). In Scheme 5 below, Q and R 2 has the above meaning according to the present invention. 3 is, for example, but not limited to, fluorine, and R 4 is, for example, but not limited to, chlorine or nitro, and R 1 , R 5 , R 6 , R 7 is, for example, but not limited to, hydrogen; X is, for example, but not limited to, oxygen; Y is, for example, but not limited to, sulfur; and G is, for example, but not limited to, CH.

[0075] Scheme 5 [ka]

[0076] Further substituted N-methyl-5-mercaptophenyl-1H-pyrimidine-2,4-dione intermediate (II) can also be converted to the desired compound of the present invention represented by general formula (If) (wherein X and Y are sulfur (S)) by first converting compound (III) into an intermediate of type (IX) in a suitable polar aprotic solvent (e.g., dioxane) using a suitable base, or by using a suitable transition metal catalyst (e.g., tris(dibenzylideneacetone)dipalladium(0)) with a suitable ligand (e.g., 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene) and a suitable base (e.g., diisopropyl(ethyl)amine) in conjunction with an appropriate optionally further substituted iodothiophenol (Scheme 6). In some cases, intermediate protection of the thiol group using a suitable protecting group may be necessary. Subsequently, intermediate (IX) can be reacted with a haloalkanecarboxylic acid having various substituents using a suitable base to give the desired compound of general formula (If). In the following Scheme 6, Q and R 2 , R 3 and R 4 has the above meaning according to the present invention. 1 , R 5 , R 6 , R 7 is, for example, but not limited to, hydrogen, X and Y are, for example, but not limited to, sulfur, and G is, for example, but not limited to, CH. Further, for clarity, the reaction pathway is depicted below in Scheme 6 using, for example, but not limited to, iodoacetate. Also suitable for coupling with intermediate (IX) are analogous haloalkanecarboxylic acids (halogen = bromine or chlorine).

[0077] Scheme 6 [ka]

[0078] Selected detailed synthetic examples for compounds of the present invention represented by general formula (I) are presented below. The example numbers listed correspond to the numbering system in Tables I.1 to I.33 below. The chemical examples reported in the following sections are: 1 H NMR spectroscopic data ( 1 For H-NMR, 400 MHz; solvent: CDCl3, CD3OD, or d6-DMSO; internal standard: tetramethylsilane (δ = 0.00 ppm) was obtained on a Bruker instrument, and the signals listed have the meanings given below: br = broad line; 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, only the significant signals for each of the two diastereomers or the characteristic signal of the major 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. [Example]

[0079] Synthesis Examples: Example I.7-2: 1-Cyclopropylethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate [ka]

[0080] To a solution of 1-cyclopropylethanol (0.035 g, 0.408 mmol) in 5 mL of dichloromethane was added [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy]acetic acid (0.150 g, 0.292 mmol), followed by successive addition of 1-hydroxy-1H-benzotriazole hydrate (0.058 g, 0.379 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.073 g, 0.379 mmol) and 4-dimethylaminopyridine (10 mol%), and the mixture was stirred at room temperature for 4 hours. Water and dichloromethane were added to the reaction mixture, the aqueous phase was repeatedly extracted with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by silica gel column chromatography using an n-heptane / ethyl acetate gradient, 0.122 g (71% of theory) of a colorless solid was obtained.

[0081] 1 H-NMR (CDCl3δ, ppm) 7.36 (d, 1H), 7.13-7.10 (m, 1H), 7.09-7.06 (m, 1H), 7.00-6.98 (m, 1H), 6.92-6.90 (m, 1H), 6.78 (d, 1H), 6.27 (s, 1H), 4.64 (m, 2H), 4.37 (q, 1H), 3.50 (s, 3H), 1.29 (d, 3H), 1.04-0.92 (m, 1H), 0.58-0.43 (m, 2H), 0.40-0.32 (m, 1H), 0.27-0.20 (m, 1H).

[0082] Example I.7-10: Cyclobutylmethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate [ka]

[0083] To a solution of 1-cyclobutylmethanol (0.035 g, 0.408 mmol) in 5 mL of dichloromethane was added [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy]acetic acid (0.150 g, 0.292 mmol), followed by successive addition of 1-hydroxy-1H-benzotriazole hydrate (0.058 g, 0.379 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.073 g, 0.379 mmol) and 4-dimethylaminopyridine (10 mol%), and the mixture was stirred at room temperature for 4 hours. Water and dichloromethane were added to the reaction mixture, the aqueous phase was repeatedly extracted with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by silica gel column chromatography using an n-heptane / ethyl acetate gradient, 0.139 g (81% of theory) of a colorless solid was obtained.

[0084] 1 H-NMR (CDCl3δ, ppm) 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.06-7.04 (m, 1H), 7.01-6.97 (m, 1H), 6.92-6.89 (m, 1H), 6.77 (d, 1H), 6.28 (s, 1H), 4.66 (s, 2H), 4.10 (d, 2H), 3.50 (s, 3H), 2.59 (sept, 1H), 2.06-1.97 (m, 2H), 1.91-1.80 (m, 2H), 1.75-1.71 (m, 2H).

[0085] Example I.7-18: Spiro[2.2]pentan-1-ylmethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate [ka]

[0086] To a solution of spiro[2.2]pentan-1-ylmethanol (0.045 g, 0.463 mmol) in 5 mL of dichloromethane was added [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy]acetic acid (0.170 g, 0.330 mmol), followed by successive addition of 1-hydroxy-1H-benzotriazole hydrate (0.066 g, 0.430 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.082 g, 0.043 mmol) and 4-dimethylaminopyridine (10 mol%), and the mixture was stirred at room temperature for 2 hours. Water and dichloromethane were added to the reaction mixture, the aqueous phase was repeatedly extracted with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by silica gel column chromatography using an n-heptane / ethyl acetate gradient, 0.170 g (86% of theory) of a colorless solid was obtained.

[0087] 1 H-NMR (CDCl3δ, ppm) 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.04 (m, 1H), 7.01-6.97 (m, 1H), 6.91-6.89 (m, 1H), 6.78 (d, 1H), 6.28 (s, 1H), 4.65 (s, 2H), 4.16-4.02 (m, 2H), 3.50 (s, 3H), 1.50-1.43 (m, 1H), 1.04-1.01 (m, 1H), 0.79-0.68 (m, 5H).

[0088] Example I.8-1: Cyclopropylmethyl (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate [ka]

[0089] To a solution of 1-cyclopropylmethanol (98%, 81 mg, 1.09 mmol) in 10 mL of dichloromethane was added (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (450 mg, 0.84 mmol), followed by 1-hydroxy-1H-benzotriazole hydrate (148 mg, 1.10 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (210 mg, 1.10 mmol), and a catalytic amount of 4-dimethylaminopyridine (10 mg), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was left overnight, and subsequent reaction monitoring by thin-layer chromatography showed incomplete conversion. Therefore, 1-hydroxy-1H-benzotriazole hydrate (148 mg, 1.10 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (210 mg, 1.10 mmol), and a catalytic amount of 4-dimethylaminopyridine (10 mg) were again added. The mixture was stirred at room temperature for another 5 hours, and reaction monitoring by thin-layer chromatography confirmed essentially complete conversion. Water was added to the reaction mixture, the phases were separated using a separator cartridge, and the solvent was removed under reduced pressure. Purification by silica gel column chromatography using an n-heptane / ethyl acetate gradient gave cyclopropylmethyl (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (477 mg, 95% of theory) in the form of a colorless oil.

[0090] 1 H-NMR (CDCl3δ, ppm): 7.52 (d, 1H), 7.14-6.92 (m, 4H), 6.74 (d, 1H), 6.27 (s, 1H), 4.67 (s, 2H), 3.96 (d, 2H), 3.50 (s, 3H), 1.11 (m, 1H), 0.56 (m, 2H), 0.26 (m, 2H).

[0091] Example I.9-1: Cyclopropylmethyl (2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate [ka]

[0092] Under argon, the initial charge of cyclopropylmethyl (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (327 mg, 0.56 mmol) together with zinc cyanide (69 mg, 0.59 mmol) and tetrakis(triphenylphosphine)palladium(0) (65 mg, 0.06 mmol) in 10 mL of N,N-dimethylacetamide was stirred at an oil bath temperature of 180 °C for 1 h. After TLC monitoring, which indicated complete conversion, the reaction mixture was added to 10 mL of water and repeatedly extracted with ethyl acetate. The combined organic phases were washed twice with saturated sodium chloride solution, then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product obtained was purified by silica gel column chromatography using an n-heptane / ethyl acetate gradient to give cyclopropylmethyl (2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (201 mg, 64% of theory) in the form of a colorless oil.

[0093] 1 H-NMR (CDCl3δ, ppm): 7.49 (d, 1H), 7.20 (m, 2H), 7.04 (dt, 1H), 6.88 (dd, 1H), 6.80 (d, 1H), ), 6.26 (s, 1H), 4.64 (s, 2H), 3.94 (d, 2H), 3.49 (s, 3H), 1.10 (m, 1H), 0.56 (m, 2H), 0.25 (m, 2H).

[0094] Analogously to the preparative examples cited above and described where appropriate, and taking into account the general details for the preparation of substituted N-heterocyclyltetrahydropyrimidinones and N-heteroaryltetrahydropyrimidinones, the compounds described below are obtained. [ka]

[0095] Table I.1: Preferred compounds represented by formula (I.1) are compounds I.1-1 to I.1-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.1-1 to I.1-25 in Table I.1 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [Table 1]

[0096] [ka]

[0097] Table I.2: Preferred compounds represented by formula (I.2) are compounds I.2-1 to I.2-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.2-1 to I.2-25 in Table I.2 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0098] Table I.3: Preferred compounds of formula (I.3) are compounds I.3-1 to I.3-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.3-1 to I.3-25 in Table I.3 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0099] Table I.4: Preferred compounds of formula (I.4) are compounds I.4-1 to I.4-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.4-1 to I.4-25 in Table I.4 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0100] Table I.5: Preferred compounds represented by formula (I.5) are compounds I.5-1 to I.5-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.5-1 to I.5-25 in Table I.5 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0101] Table I.6: Preferred compounds of formula (I.6) are compounds I.6-1 to I.6-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.6-1 to I.6-25 in Table I.6 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0102] Table I.7: Preferred compounds of formula (I.7) are compounds I.7-1 to I.7-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.7-1 to I.7-25 in Table I.7 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0103] Table I.8: Preferred compounds of formula (I.8) are compounds I.8-1 to I.8-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.8-1 to I.8-25 in Table I.8 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0104] Table I.9: Preferred compounds of formula (I.9) are compounds I.9-1 to I.9-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.9-1 to I.9-25 in Table I.9 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0105] Table I.10: Preferred compounds of formula (I.10) are compounds I.10-1 to I.10-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.10-1 to I.10-25 in Table I.10 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0106] Table I.11: Preferred compounds of formula (I.11) are compounds I.11-1 to I.11-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.11-1 to I.11-25 in Table I.11 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0107] Table I.12: Preferred compounds of formula (I.12) are compounds I.12-1 to I.12-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.12-1 to I.12-25 in Table I.12 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0108] Table I.13: Preferred compounds of formula (I.13) are compounds I.13-1 to I.13-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.13-1 to I.13-25 in Table I.13 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0109] Table I.14: Preferred compounds of formula (I.14) are compounds I.14-1 to I.14-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.14-1 to I.14-25 in Table I.14 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0110] Table I.15: Preferred compounds of formula (I.15) are compounds I.15-1 to I.15-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.15-1 to I.15-25 in Table I.15 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0111] Table I.16: Preferred compounds of formula (I.16) are compounds I.16-1 to I.16-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.16-1 to I.16-25 in Table I.16 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0112] Table I.17: Preferred compounds of formula (I.17) are compounds I.17-1 to I.17-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.17-1 to I.17-25 in Table I.17 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0113] Table I.18: Preferred compounds of formula (I.18) are compounds I.18-1 to I.18-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.18-1 to I.18-25 in Table I.18 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0114] Table I.19: Preferred compounds of formula (I.19) are compounds I.19-1 to I.19-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.19-1 to I.19-25 in Table I.19 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0115] Table I.20: Preferred compounds of formula (I.20) are compounds I.20-1 to I.20-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.20-1 to I.20-25 in Table I.20 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0116] Table I.21: Preferred compounds of formula (I.21) are compounds I.21-1 to I.21-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.21-1 to I.21-25 in Table I.21 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0117] Table I.22: Preferred compounds of formula (I.22) are compounds I.22-1 to I.22-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.22-1 to I.22-25 in Table I.22 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0118] Table I.23: Preferred compounds of formula (I.23) are compounds I.23-1 to I.23-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.23-1 to I.23-25 ​​in Table I.23 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0119] Table I.24: Preferred compounds of formula (I.24) are compounds I.24-1 to I.24-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.24-1 to I.24-25 in Table I.24 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0120] Table I.25: Preferred compounds of formula (I.25) are compounds I.25-1 to I.25-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.25-1 to I.25-25 in Table I.25 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0121] Table I.26: Preferred compounds of formula (I.26) are compounds I.26-1 to I.26-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.26-1 to I.22-25 in Table I.26 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0122] Table I.27: Preferred compounds of formula (I.27) are compounds I.27-1 to I.27-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.27-1 to I.27-25 in Table I.27 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0123] Table I.28: Preferred compounds of formula (I.28) are compounds I.28-1 to I.28-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.28-1 to I.28-25 in Table I.28 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0124] Table I.29: Preferred compounds of formula (I.29) are compounds I.29-1 to I.29-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.29-1 to I.29-25 in Table I.29 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0125] Table I.30: Preferred compounds of formula (I.30) are compounds I.30-1 to I.30-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.30-1 to I.30-25 in Table I.30 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0126] Table I.31: Preferred compounds of formula (I.31) are compounds I.31-1 to I.31-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.31-1 to I.31-25 in Table I.31 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0127] Table I.32: Preferred compounds of formula (I.32) are compounds I.32-1 to I.32-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.32-1 to I.32-25 in Table I.32 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively. [ka]

[0128] Table I.33: Preferred compounds of formula (I.33) are compounds I.33-1 to I.33-25, where Q has the meaning shown in each row of Table 1. Accordingly, compounds I.33-1 to I.33-25 in Table I.33 are defined by the meanings of entry numbers 1 to 25 for Q in Table 1, respectively.

[0129] NMR data of selected examples: 1 1 H NMR data can be analyzed in two different ways: (a) by conventional interpretation of NMR; or (b) by the method described below. 1 1 H NMR peak list;

[0130] (a) Conventional interpretation of NMR Example I.7-12: 1 H-NMR (CDCl3δ, ppm) 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.04 (m, 1H), 7.01-6.97 (m, 1H), 6.92-6.90 (m, 1H), 6.77 (d, 1H), 6.28 (s, 1H), 4.66 (s, 2H), 4.02 (d, 2H), 3.50 (s, 3H), 2.17 (sept, 1H), 1.73-1.65 (m, 2H), 1.61-1.50 (m, 4H), 1.23-1.16 (m, 2H).

[0131] (b) NMR peak list method Selected Examples 1 H-NMR data is 1 The data are presented in the form of a H-NMR peak list. For each signal peak, the δ value (ppm) is listed first, followed by the signal intensity in parentheses. Pairs of δ value / signal intensity number for different signal peaks are listed, separated from each other by semicolons.

[0132] Thus, the peak list for one example takes the form: δ1(Intensity 1);δ2(Intensity 2);...;δ i (strength i );...;δ n (strength n ).

[0133] The intensity of the sharp signal correlates with the signal height (cm) in the printed example of the NMR spectrum, showing the true ratio of signal intensities. In the case of a broad signal, several peaks or the center of the signal and their relative intensities can be shown compared to the most intense signal in the spectrum.

[0134] 1To calibrate the chemical shifts of H NMR spectra, tetramethylsilane and / or, especially if the spectrum is measured in DMSO, the chemical shifts of the solvent are used, and therefore, the tetramethylsilane peak may, but need not, be present in the NMR peak list.

[0135] 1 The list of H NMR peaks is given in the conventional 1 It resembles a 1 H NMR printout and therefore contains all the peaks that would normally be described in conventional NMR interpretations.

[0136] Furthermore, they are 1 Like the 1 H NMR printout, the signals of the solvent, the signals of the stereoisomers of the target compound (which are likewise provided by the present invention) and / or the signals of impurity peaks may also be shown.

[0137] In recording compound signals within the delta range of solvent and / or water, 1 Our list of H NMR peaks shows the peaks of standard solvents, e.g., the DMSO peak in DMSO-D6, and the water peak, which usually have high intensity on average.

[0138] The peaks of stereoisomers of the target compound and / or the peaks of impurities typically have, on average, lower intensities than the peaks of the target compound (eg, a target compound having a purity of greater than 90%).

[0139] Such stereoisomers and / or impurities may be unique to a particular preparation method, and therefore their peaks may help to confirm the reproducibility of our preparation method in terms of "by-product fingerprints."

[0140] The expert calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, and also using empirically evaluated expected values), and can optionally use additional intensity filters to separate the peaks of the target compounds, if necessary. This separation can be achieved by: 1 This would be similar to picking the peaks in conventional interpretation of H NMR.

[0141] 1 Further details regarding the 1 H NMR peak list can be found in Research Disclosure Database Number 564025. [Table 2]

[0142] TIFF2025534472000056.tif252165

[0143] TIFF2025534472000057.tif252166

[0144] TIFF2025534472000058.tif252165

[0145] TIFF2025534472000059.tif251165

[0146] TIFF2025534472000060.tif68165

[0147] The present invention further provides the use of one or more compounds of the invention of general formula (I) as defined above and / or their salts, preferably the use of one or more compounds of the invention of general formula (I) as defined in one of the embodiments identified as preferred or particularly preferred and / or their salts, as herbicides and / or plant growth regulators, preferably in crops of useful plants and / or ornamental plants, in particular the use of one or more compounds of formula (1.1) to formula (1.33) and / or their salts, in each case as defined above.

[0148] The present invention further provides a method for controlling harmful plants and / or regulating plant growth, which method comprises administering an effective amount of one or more compounds of the invention of general formula (I) as defined above and / or salts thereof, preferably one or more compounds of the invention of general formula (I) as defined in one of the embodiments identified as preferred or particularly preferred and / or salts thereof, in particular one or more compounds of formulae (1.1) to (1.33) and / or salts thereof, in each case as defined above; or a composition of the invention as defined below; to the (harmful) plants, to the seeds of the (harmful) plants, to the soil in or on which the (harmful) plants grow, or to cultivated areas.

[0149] The present invention further provides a method for controlling undesirable plants, preferably in crops of useful plants, which method comprises administering an effective amount of one or more compounds of general formula (I) and / or salts thereof as defined above, preferably one or more compounds of general formula (I) and / or salts thereof as defined in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of formulae (1.1) to (1.33) and / or salts thereof, in each case as defined above; or a composition of the invention as defined below; to undesirable plants (e.g., harmful plants, e.g., monocotyledonous or dicotyledonous weeds or undesirable crop plants), seeds of the undesirable plants (i.e., seeds of plants, e.g., grains, seeds, or vegetative propagation organs, e.g., shoot parts having tubers or buds), soil in or on which undesirable plants grow (e.g., soil of crop-growing land or non-crop land), or cultivated areas (i.e., areas where undesirable plants will grow).

[0150] The present invention further provides a method for controlling the growth of plants, preferably useful plants, comprising administering an effective amount of one or more compounds of general formula (I) and / or salts thereof as defined above, preferably one or more compounds of general formula (I) and / or salts thereof as defined in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of formulae (1.1) to (1.33) and / or salts thereof, in each case as defined above; or a composition of the invention as defined below; to the plant, the seed of the plant (i.e., the seed of the plant, such as grain, seed, or vegetative propagation organs, such as tubers or shoot parts bearing sprouts), the soil in or on which the plant is growing (e.g., soil of arable or non-arable land), or the cultivated area (i.e., the area where the plant will be growing).

[0151] In this regard, the compounds of the present invention represented by general formula (I) or the compositions of the present invention can be applied, for example, by the pre-sowing method (and, if appropriate, by incorporation into the soil), by the pre-emergence method, and / or by the post-emergence method. Specific examples of some representative monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds of the present invention are as follows, but it is not intended that such listings be limited to any particular species.

[0152] In the method of the present invention for controlling harmful plants or regulating plant growth, one or more compounds of general formula (I) and / or their salts are preferably used to control harmful plants in crops of useful plants or ornamental plants or to regulate the growth of crops of useful plants or ornamental plants, wherein in a preferred configuration said useful plants or ornamental plants are transgenic plants.

[0153] The compounds of the invention of general formula (I) and / or their salts are suitable for controlling the following genera of harmful monocotyledonous and dicotyledonous plants: Monocotyledonous harmful plants of the following genera:: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, The genera Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum.

[0154] Dicotyledonous harmful plants of the following genera:: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirrus sium), Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium dium), Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, and Rumex Rotala), Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica,Viola, Xanthium.

[0155] When the compound of the present invention represented by general formula (I) is applied to the soil surface before the germination of harmful plants (grass weeds and / or broadleaf weeds) (pre-emergence method), the emergence of seedlings of grass weeds or broadleaf weeds is completely prevented, or the weeds grow until they reach the cotyledon stage, then stop growing, and finally, after a lapse of 3 to 4 weeks, they completely die.

[0156] When the compounds of the present invention of general formula (I) are applied post-emergence to the green parts of the plants, growth stops after the treatment and the harmful plants remain in the growth stage at the time of application or die completely after a certain period of time, so that competition with weeds harmful to the crop plants is eliminated very early and lastingly.

[0157] The compounds of the present invention represented by the general formula (I) exhibit excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, but are not effective against economically important crop plants such as Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus vulgaris, and the like. Depending on the structure of the particular compound of the invention and its application rate, only minor or no damage is caused to dicotyledonous crop plants of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, and Zea, or monocotyledonous crop plants of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, and Zea. For this reason, the compounds of the invention are highly suitable for selectively controlling undesired plant growth in crop plants, such as agriculturally useful plants, or ornamental plants.

[0158] Furthermore, the compounds of the present invention represented by general formula (I) (depending on their individual structure and the application rate used) have excellent growth-regulating properties in crop plants. They can be used to intervene in the metabolism of the plant itself with a regulating effect, thus exerting a controlled influence on plant components and facilitating harvesting, for example, by inducing drought and growth inhibition. Furthermore, they are also suitable for the overall control and inhibition of undesirable plant growth without killing the plant in the process. Inhibiting plant growth plays an important role in many types of monocotyledonous and dicotyledonous crop plants, for example, because it can reduce or completely prevent lodging.

[0159] The compounds of the present invention represented by general formula (I) can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis due to their herbicidal and plant growth-regulating properties. Generally, transgenic plants are characterized by specific advantageous properties, such as resistance to specific pesticides (especially specific herbicides), resistance to plant diseases or pathogens of plant diseases (e.g., specific insects or microorganisms, such as fungi, bacteria, or viruses). Other special properties relate, for example, to the quantity, quality, storability, composition, and specific components of the harvested product. For example, transgenic plants with increased starch content or modified starch quality, or transgenic plants with harvested products having different fatty acid compositions, are known.

[0160] For the purpose of transgenic crops, the compounds of the present invention represented by general formula (I) and / or salts thereof are preferably used in economically important transgenic crops of useful plants and ornamental plants (e.g., cereals such as wheat, barley, rye, oats, millet, rice and maize, or crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables).

[0161] The compounds of the invention of general formula (I) are also preferably used as herbicides in crops of useful plants which are resistant or made resistant by recombinant means to the phytotoxic effects of the herbicides in question.

[0162] The compounds of the present invention represented by general formula (I) can also be used to control harmful plants in crops of known or yet to be developed transgenic plants due to their herbicidal and plant growth-regulating properties. Generally, transgenic plants are characterized by specific advantageous properties, such as resistance to specific pesticides (especially specific herbicides), resistance to plant diseases or plant disease pathogens (e.g., specific insects or microorganisms, such as fungi, bacteria, or viruses). Other special properties relate, for example, to the quantity, quality, storability, composition, and specific components of the harvest. For example, transgenic plants with increased starch content or modified starch quality, or transgenic plants with harvests having a different fatty acid composition, are known. Another special property can be tolerance or resistance to abiotic stresses (e.g., heat, cold, drought, salinity, and UV radiation).

[0163] The compounds of the present invention of general formula (I) or their salts are preferably used in economically important transgenic crops of useful and ornamental plants (e.g. cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize, or crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables).

[0164] The compounds of general formula (I) are preferably used as herbicides in crops of useful plants which are resistant or made resistant by recombinant means to the phytotoxic effects of the herbicides in question.

[0165] Conventional methods for generating novel plants with modified properties compared to existing plants include, for example, conventional cultivation methods and the generation of mutants. Alternatively, novel plants with modified properties can be generated using recombinant methods.

[0166] Many molecular biology techniques are known to those skilled in the art that allow the production of novel transgenic plants with modified properties. For such genetic manipulation, nucleic acid molecules that allow sequence changes by mutagenesis or recombination of DNA sequences can be introduced into plasmids. Using standard methods, for example, base exchanges can be performed, partial sequences can be removed, or natural or synthetic sequences can be added. Adapters or linkers can be attached to DNA fragments to link them to each other.

[0167] For example, the generation of plant cells with reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, or by expressing a sense RNA to achieve a co-suppression effect, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of said gene product.

[0168] For this purpose, it is possible to use, firstly, DNA molecules containing the entire coding sequence of the gene product, including all possible flanking sequences, and also DNA molecules containing only a portion of the coding sequence (in this case, these portions must be long enough to exert an antisense effect in cells), and also DNA sequences that are highly homologous to the coding sequence of the gene product, but not completely identical thereto, can also be used.

[0169] When expressing a nucleic acid molecule in a plant body, the synthesized protein can be localized in any desired compartment of the plant cell. However, to localize it in a specific compartment, for example, the coding region can be linked 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). Furthermore, such nucleic acid molecules can also be expressed in organelles of plant cells.

[0170] The transgenic plant cells can be regenerated by known techniques to give rise to whole plants. In principle, the transgenic plants can be of any desired plant species, i.e., not only monocotyledonous plants but also dicotyledonous plants.

[0171] In this way, transgenic plants can be obtained which have properties altered by overexpression, suppression or inhibition of a homologous (= natural) gene or gene sequence or by expression of a heterologous (= foreign) gene or gene sequence.

[0172] The compounds of the present invention of general formula (I) are preferably used in transgenic crops which are resistant to growth regulators (e.g. dicamba) or to herbicides which inhibit essential plant enzymes (e.g. acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD)), or in transgenic crops which are resistant to herbicides selected from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and similar active ingredients.

[0173] The use of the compounds of the present invention of general formula (I) in transgenic crops not only results in the effects against harmful plants observed in other crops, but also in many cases in effects specific to the application in the particular transgenic crop, such as a modified or especially expanded spectrum of weeds that can be controlled, modified application rates that can be used for said application, preferably better compatibility with herbicides to which the transgenic crop is resistant, as well as effects on the growth and yield of the transgenic crop plants.

[0174] The present invention therefore also relates to the use of the compounds of the invention 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.

[0175] Preferred is the use in cereals, here preferably maize, wheat, barley, rye, oats, millet or rice, by the pre-emergence or post-emergence method.

[0176] Preference is also given to the use in soybeans by the pre-emergence or post-emergence method.

[0177] Uses according to the present invention for controlling harmful plants or regulating plant growth also include cases where the compound of general formula (I) or a salt thereof is not formed from a precursor ("prodrug") until after application onto or within the plant or in the soil.

[0178] The present invention also provides the use of one or more compounds of general formula (I) or their salts or the composition of the invention (defined below) for controlling harmful plants or regulating plant growth (in a method for controlling harmful plants or in a method for regulating plant growth), wherein the use comprises applying an effective amount of one or more compounds of general formula (I) or their salts to the surface of the plant (harmful plants, where appropriate harmful plants present together with useful plants), to the seeds of the plant, to the soil in or on which the plants grow, or to the cultivated area.

[0179] The present invention also provides a herbicide composition and / or a plant growth regulator composition, wherein the composition comprises: (a) one or more compounds of general formula (I) as defined above and / or salts thereof, preferably one or more compounds of general formula (I) as defined in one of the embodiments identified as preferred or particularly preferred and / or salts thereof, in particular one or more compounds of formulae (1.1) to (1.33) and / or salts thereof, in each case as defined above; and, (b) one or more further substances selected from group (i) and / or group (ii): (i) one or more further pesticidal active substances, preferably one or more further pesticidal active substances selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. herbicides not conforming to general formula (I) as defined above), fungicides, phytotoxicants, fertilizers and / or further growth regulators; (ii) one or more formulation adjuvants customary in crop protection; The present invention is characterized by comprising:

[0180] The further pesticide active substance of component (i) of the composition of the present invention is preferably selected from the group of substances described in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Society of Chemistry, 2012.

[0181] The herbicidal or plant growth regulator compositions of the invention preferably comprise one, two 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 that 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 that are miscible with water in any proportion at 25°C and 1013 mbar).

[0182] The compounds of the present invention represented by general formula (I) can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in conventional formulations. Therefore, the present invention also provides herbicidal compositions and plant growth regulator compositions containing the compounds of general formula (I) and / or their salts.

[0183] The compounds of the present invention of general formula (I) and / or their salts can be formulated in various ways depending on the biological and / or physicochemical parameters specified. Possible formulations include, for example, wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water emulsions and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or aqueous dispersions, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, broadcast granules and soil-applied granules, granules in the form of fine particles (GR), spray granules, absorption granules and impregnated granules. granules, water dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, and waxes.

[0184] These individual formulation types and formulation auxiliaries (e.g., inert substances, surfactants, solvents and further additives) are 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; Hv Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, NY; C. Marsden, "Solvents Guide", 2nd ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Interface-active ethylene oxide]. 1986.

[0185] Wettable powders are preparations that can be homogeneously dispersed in water and contain, in addition to the active ingredient, apart from diluents or inert substances, further surfactants of the ionic and / or nonionic type (wetting agents, dispersants), such as polyoxyethylated alkylphenols, polyoxyethylated aliphatic alcohols, polyoxyethylated aliphatic amines, aliphatic 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 herbicidal active ingredient is pulverized in conventional equipment, such as a hammer mill, blower mill, or air jet mill, and simultaneously or subsequently mixed with formulation adjuvants.

[0186] 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 relatively high boiling points) or a mixture of such organic solvents, and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used include calcium salts of alkylarylsulfonic acid, such as calcium dodecylbenzenesulfonate, or nonionic 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.

[0187] Dusting products are obtained by grinding the active ingredient with finely distributed solids (for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth).

[0188] Suspension formulations can be aqueous or oil-based. They can be prepared, for example, by wet-milling using a standard commercial bead mill, optionally with the addition of a surfactant (e.g., a surfactant already mentioned above for the other formulation types).

[0189] Emulsions, for example oil-in-water 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 a stirrer, a colloid mill and / or a static mixer.

[0190] 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) using 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) using conventional methods for producing fertilizer granules.

[0191] Water dispersible granules are generally prepared by conventional methods such as spray drying, fluidized bed granulation, pan granulation, mixing using high speed mixers, and extrusion without solid inert materials.

[0192] For the preparation of pan granules, fluidized bed granules, extruded granules and spray granules, reference is made, for example, to the methods described in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; "Agglomeration" by J.E. Browning, Chemical and Engineering 1967, pages 147 ff.; and "Perry's Chemical Engineer's Handbook", 5th ed., McGraw-Hill, New York 1973, pp. 8-57.

[0193] 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.

[0194] The pesticide preparation of the present invention, preferably a herbicide composition or a plant growth regulator composition, preferably contains a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, and particularly preferably 2 to 80% by weight of the active ingredient represented by general formula (I) and / or a salt thereof.

[0195] In wettable powders, the concentration of the active ingredient is, for example, about 10% to 90% by weight, with the remainder to 100% by weight consisting 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 powder form contain 1% to 30% by weight of the 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 the active ingredient. In water dispersible granules, the content of the active ingredient depends in part on whether the active ingredient is in liquid or solid form and in part on what granulation aids, fillers, etc. are used. In water dispersible granules, the content of the active ingredient is, for example, 1% to 95% by weight, preferably 10% to 80% by weight.

[0196] Furthermore, the formulation of the active ingredient may optionally contain customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, extenders, carriers, dyes, antifoaming agents, evaporation retardants, and agents for influencing pH and viscosity. Examples of formulation auxiliaries are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998)".

[0197] The compound of the present invention represented by general formula (I) or a salt thereof can be used alone or in the form of a preparation (formulation) in which it is combined with another pesticidal active substance (e.g., insecticide, acaricide, nematicide, herbicide, fungicide), safener, fertilizer and / or growth regulator, for example, in the form of a finished formulation or tank mix. Such a combined formulation can be prepared based on the above formulation, taking into consideration the physical properties and stability of the active ingredients to be combined.

[0198] Combination partners that can be used in the mixed formulation or tank mix with the compound of the present invention represented by general formula (I) are, for example, known active ingredients based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, etc., as described, for example, in "Weed Research 26 (1986) 441-445" or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012" and the literature cited therein.

[0199] Of particular interest is the selective control of harmful plants among useful plant crops and ornamental plants. Although the compounds of the present invention represented by general formula (I) have already demonstrated very good to sufficient selectivity in many types of crops, in principle, phytotoxicity to crop plants may occur in some crops, especially in mixtures with other herbicides with less selectivity. In this regard, a particularly interesting combination of the compounds of the present invention represented by general formula (I) is the combination of compound (I) with another herbicide or pesticide and a safener. The safener is used in an effective amount to exhibit a detoxifying effect, and such a safener reduces the secondary phytotoxic effects of the herbicide / pesticide used, for example, in economically important crops, such as cereals (wheat, barley, rye, corn, rice, foxtail millet), sugar beet, sugarcane, rapeseed, cotton, and soybean, preferably cereals.

[0200] The weight ratio of herbicide (mixture) to safener generally depends on the rate of application of the herbicide and the efficacy of the safener 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. Like the compounds of general formula (I) or mixtures thereof, the safeners can also be formulated together with further herbicides / pesticides and can be supplied and used as finished formulations or tank mixes containing the herbicide.

[0201] For application, herbicide or herbicide-safener formulations in the form in which they are marketed are, where appropriate, diluted in the customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water dispersible granules. Preparations in the form of dusts, granules for soil application or broadcast and sprayable solutions are usually not further diluted with other inert substances before application.

[0202] The application rate of the compounds of the present invention represented by general formula (I) and / or their salts is influenced to some extent by external conditions (e.g., temperature, humidity, etc.). The application rate can vary within a wide range. When applied as a herbicide to control harmful plants, the total amount of the compounds of the present invention represented by general formula (I) and their salts 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, and particularly preferably in the range of 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence applications.

[0203] When the compounds of the present invention of general formula (I) and / or their salts are used as plant growth regulators, for example as culm stabilizers for crop plants (preferably cereal plants such as wheat, barley, rye, triticale, millet, rice or corn) as described above, 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 to both pre-emergence and post-emergence application.

[0204] Application as a culm stabilizer can be carried out at various stages of plant development, preference being given to application at the beginning of vertical growth, for example after the tillering phase.

[0205] Alternatively, application as a plant growth regulator can be by seed treatment, which includes various techniques for dressing and coating seeds. The application rate depends on the particular technique and can be determined by preliminary tests.

[0206] Combination partners that can be used in the mixed formulation or tank mix with the compound of general formula (I) are, for example, known active ingredients that are based on inhibiting, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, or protoporphyrinogen oxidase, or that act as plant growth regulators, as known, for example, from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006, and the references cited therein.

[0207] Examples of known herbicides or plant growth regulators that can be combined with the compounds of general formula (I) include the following active ingredients (wherein the compounds are designated by their "common names" according to the International Organization for Standardization (ISO), or by their chemical names, or by their code numbers), and always include all use forms (e.g., acids, salts, esters) and all isomers (e.g., stereoisomers and optical isomers). These include, for example, single use forms, but in some cases, multiple use forms: Acetochlor, acifluorfen, acifluorfen-methyl, 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, aminocyclopyrachloro-potassium, aminocyclopyrachloro-methyl, aminopyralid, aminopyralid-dimethylammonium, Aminopyralid-trypromine, amitrole, ammonium sulfamate, anilofos, asulam, asulam-potassium, asulam-sodium, atrazine, azafenidine, azimsulfuron, beflubutamid, (S)-(-)-beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, benazolin-dimethylammonium, benazolin-potassium, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, bentazone-sodium, benzobicyclon, benzofenap, bicyclo Ropirone, Bifenox, Biranaphos, Biranaphos-sodium, Bipyrazone, Bispyribac, Bispyribac-sodium, Bixlozone, Bromacil, Bromacil-lithium, Bromacil-sodium, Bromobutide, Bromofenoxime, Bromoxynil, Bromoxynil-butyrate, Bromoxynil-potassium, Bromoxynil-heptanoate and Bromoxynil-octanoate, Busoxinon, Butachlor, Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butyrate, Caffeine dextrol, cambendichlor, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium, chloramben-sodium, chlorbromuron, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim,Chlorotoluron, chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, cinidon, cinidon-ethyl, symmetryn, exo-(+)-symmetryn, i.e., (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, exo-(-)-symmetryn, i.e., (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo [2.2.1]Heptane, cinosulfuron, clasifos, clethodim, clodinafop, clodinafop-ethyl, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-methyl, clopyralid-olamine, clopyralid-potassium, clopyralid-trypomine, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranyl, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyha bromophenone-butyl, ciprazine, 2,4-D (and their ammonium salts, butotyl salt, butyl salt, choline salt, diethylammonium salt, dimethylammonium salt, diolamine salt, doboxyl salt, dodecylammonium salt, etexyl salt, ethyl salt, 2-ethylhexyl salt, heptylammonium salt, isobutyl salt, isooctyl salt, isopropyl salt, isopropylammonium salt, lithium salt, meptyl salt, methyl salt, potassium salt, tetradecylammonium salt, triethylammonium salt, triisopropylammonium salt, isopropanol ammonium salt, trypromine salt and trolamine salt), 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl, 2,4-DB-potassium and 2,4-DB-sodium, daimuron (dymron), dalapon, dalapon-calcium, dalapon-magnesium, dalapon-sodium, dazomet, dazomet-sodium, n-decanol, 7-deoxy-D-sedoheptulose, desmedipham, detosyl pyrazolate (DTP), dicamba and its salts (e.g., dicamba biproamine, dicamba N,N-bis(3-aminopropyl)methylamine, dicamba butotyl, dicamba choline,Dicamba-diglycolamine, Dicamba-dimethylammonium, Dicamba-diethanolamine ammonium, Dicamba-diethylammonium, Dicamba-isopropylammonium, Dicamba-methyl, Dicamba-monoethanolamine, Dicamba-olamine, Dicamba-potassium, Dicamba-sodium, Dicamba-triethanolamine), Dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-di Methyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-ethexyl, dichlorprop-ethylammonium, dichlorprop-isooctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-ethexyl, dichlorprop-P-potassium, dichlorprop- Sodium, Diclofop, Diclofop-methyl, Diclofop-P, Diclofop-P-methyl, Diclosulam, Difenzoquat, Difenzoquat-methyl sulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr-sodium, Dimefurone, Dimepiperate, Dimethasulfazate, Dimethachlor, Dimethametrin, Dimethenamid, Dimethenamid-P, Dimetrasulfuron, Dinitramine, Dinoterb, Dinoterb-acetate, Diphenamide, Diquat, Diquat-dibromide, Diquat Dichloride, dithiopyr, diuron, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, endothall, endothall-diammonium, endothall-dipotassium, endothall-disodium, epirifenacil (S-3100), EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyphene, ethoxyphene-ethyl, ethoxysulfuron, etobenzanide, F-5231, i.e.,N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1yl]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, fenpyrazone, Fenquinotrione, fentrazamide, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpi Flu-ethyl, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Fluometuron, Flurenol, Flurenol-butyl, -dimethylammonium and -methyl, Fluoroglycofen, Fluoroglycofen-ethyl, Flupropanate, Flupropanate-sodium, Flupyrsulfuron, Flupyrsulfuron-methyl, Flupyrsulfuron-methyl-sodium, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr-butomethyl, Fluroxypyr-meptyl, Flurtamone, Fluthiacet, Flu Luciaset-methyl, fomesafen, fomesafen-sodium, foramsulfuron, foramsulfuron-sodium, fosamine, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium,Glyphosate-potassium, glyphosate-sodium, glyphosate-sesquisodium and glyphosate-trimesium, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl)O-ethyl isopropylphosphoramidothioate, haloxifen, haloxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, haloxyfop-sodium, hexazinone, HNPC-A8169, i.e., prop-2-yn-1-yl(2S)-2-{3-[(5-tert-butylpyridine-2- 1-(2,4-dichlorophenoxy)-1-yl)oxy]phenoxy}propanoate, HW-02, i.e., 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, hydantocidin, icafolin, icafolin-methyl, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium methyl, imazaquin-methyl, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, indolauxipyr, iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl-sodium, ioxynil, ioxynil-lithium, -octanoate, -potassium and -sodium, ipfencarbazone, iptriazopyrid, i.e., 3-[(isopropylsulfonyl)methyl]methyl] ethyl]-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo-[4,3-a]pyridine-8-carboxamide, isoproturon, isouron, isoxaben, isoxaflutole, carbutilate, 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, ketospiradox-potassium, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -butyl, -dimethylammonium, -diolamine, -2-ethylhexyl, -ethyl, -isobutyl, isooctyl, -isopropyl, -isopropylammonium, -methyl, -olamine, -potassium, -sodium and -trolamine, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop, -butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethexyl, mecoprop-ethadyl, mecoprop-isooctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mefluidide-diolamine, mefluidide-potassium, mesosulfuron, mesosulfuron-methyl, mesosulfuron-na Thorium, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metoslam, metoxuron, metoproxybicyclon, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-methyl, MT-5950, i.e., N-[3-chloroisothiazolinone] -4-(1-methylethyl)-phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, nevron, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat-dichloride, paraquat-dimethyl sulfate, Pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, petoxamide, petroleum, phenmedipham, phenmedipham-ethyl, picloram, picloram-dimethylammonium, picloram-etexyl, picloram-isooctyl, picloram-methyl, picloram-olamine, picloram-potassium, picloram-triethylammonium, picloram-tryplomine, picloram-trolamine, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl,Prodiamines, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazines, propham, propisochlor, propoxycarbazones, propoxycarbazone sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyraquinate, pyrasulfotole, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxifen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-nat sodium, pyroxasulfone, pyroxsulam, quinclorac, quinclorac-dimethylammonium, quinclorac-methyl, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM201, i.e., 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, 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 (trichloroacetic acid) and its salts, such as TCA-ammonium, TCA-calcium, TCA-ethyl, TCA-magnesium, TCA-sodium, tebuthiuron, tefuryltriones, tembotrione, tepraloxydim, terbacil, terbucarb,Terbumeton, terbuthylazines, terbutryn, tetflupyrrolimet, taxomin, thenylchlor, thiazopyr, thiencarbazones, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-choline, triclopyr-ethyl, triclopyr-triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate sulfate), vernolate, XDE-848, ZJ-0862, i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl- ethyl 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid, [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]ethyl acetate, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl 5-chloropyrimidin-2-yl ether,2-(3,4-Dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazin-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophen-5-yl)methanone, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-yl Propane-1-sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazol-5-yl 1,3-dimethyl-1H-pyrazole-4-carboxylate; 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate cyanomethyl; 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate prop-2-yn-1-yl; 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate methyl; 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate benzyl indyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate ethyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indol-6-yl)pyridine-2-carboxylate methyl, 6-(1-acetyl-7-fluoro-1H-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate methyl, 4-amino-3-chloro-6-[1-(2,2-dimethylpropanoyl)-7-fluoro-1H-indol-6-yl]-5-fluoropyridine-2-carboxylate methyl,4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl]pyridine-2-carboxylate methyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate potassium, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate sodium, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine- Butyl 2-carboxylate, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 6- [(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2- 1-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin-1-ium salts (salts with appropriate anions (e.g., chloride, acetate, or trifluoroacetate)), 1-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-1-ium salts (salts with appropriate anions (e.g., chloride, acetate, or trifluoroacetate)), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazin-1-ium salts (salts with appropriate anions (e.g., chloride, acetate, or trifluoroacetate)),4-(pyridazin-3-yl)-1-(2-sulfoethyl)pyridazin-1-ium salts (salts with appropriate anions (e.g., chloride, acetate, or trifluoroacetate)), 1-(2-carboxyethyl)-4-(1,3-thiazol-2-yl)pyridazin-1-ium salts (salts with appropriate anions (e.g., chloride, acetate, or trifluoroacetate)), 1-(2-carboxyethyl)-4-(1,3,4-thiadiazol-2-yl)pyridazin-1-ium salts (salts with appropriate anions (e.g., chloride, acetate, or trifluoroacetate)), methyl (2R)-2-{[(E)-({2-chloro, 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, methyl (2S)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, methyl (2R / S)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, (E)-2-(trifluoromethyl)benzaldehyde O-{2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoyl}oxime, 2-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, (2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanecarboxylic acid, 2-ethoxy-2-oxoethyl 1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropanecarboxylate, 2-methoxy-2-oxoethyl 1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropanecarboxylate, {[(1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}acetic acid, 2-(2-bromo-4-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]Methyl oxazole-6a-carboxylate, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylate.

[0208] Examples of plant growth regulators as possible mixing partners are: Abscisic acid and related analogues [e.g., (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid, methyl (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoic acid, methyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoic acid, methyl (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate, (2Z,4E)-5-(2-hydroxy-1,3-dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-dienoic acid], acibenzolar, acibenzolar-S-methyl, S-adenosylhomocysteine, allantoin, 2-aminoethoxyvinylglycine (AVG), aminooxyacetic acid and related esters [e.g., (isopropylidene)aminooxyacetic acid 2-(methoxy)-2-oxoethyl ester, (isopropylidene)aminooxyacetic acid 2-(hexyloxy)-2-oxoethyl ester, (cyclohexylidene)aminooxyacetic acid-2-(isopropyloxy)-2-oxoethyl ester], 1-aminocycloprop-1-ylcarboxylic acid N-methyl-1-aminocyclopropyl-1-carboxylic acid, 1-aminocyclopropyl-1-carboxamide, substituted 1-aminocyclopropyl-1-carboxylic acid derivatives (described in DE 3335514, EP 30287, DE 2906507 or US Pat. No. 5,123,951), 1-aminocyclopropyl-1-hydroxamic acid, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl , L-canaline, catechol and catechols (e.g., (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol), chitooligosaccharides (CO; COs differ from LCOs in that they lack the fatty acid side chains characteristic of LCOs. COs, sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units, but do not themselves form chitin molecules [(CH. 13 NO5) n , CAS No. 1398-61-4] and chitosan molecule [(CH 11 NO4) n, CAS-No. 9012-76-4]), chitin-like compounds, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozide, dazomet, dazomet sodium, n-decanol, dikegulac, dikegulac sodium, endothall, endothall dipotassium (dipo tassum), -disodium and mono(N,N-dimethylalkylammonium), ethephon, 1-ethylcyclopropene, flumetralin, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonate esters or other derivatives (e.g., jasmonate methyl ester, jasmonate ethyl ester), lipochitooligosaccharides (LCOs), optionally, symbiotic nodulation signals LCOs, also called Nod or Nod factor or Myc factor, are composed of an oligosaccharide backbone consisting of β-1,4-linked N-acetyl-D-glucosamine residues ("GlcNAc") with condensed N-linked fatty acid side chains at the non-reducing end. As can be inferred from the literature, LCOs differ in the number of GlcNAc units in their backbone structure, in the length and degree of saturation of the fatty acid chains, and in the substitution of reducing and non-reducing sugar units), linoleic acid or derivatives thereof, linolenic acid or derivatives thereof, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one and related lactones (described in EP 2248421), 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenoxide mixtures, 4-oxo-4-[(2- (phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid and its salts (e.g., sodium 4-phenylbutanoate, potassium 4-phenylbutanoate), phenylalanines, N-phenylphthalamic acid, prohexadiones, prohexadione-calcium, 1-n-propylcyclopropene, putrescine, prohydrojasmone, rhizobitoxine, salicylic acid and methyl salicylate, sarcosine, sodium Cycloprop-1-en-1-yl acetate, sodium cycloprop-2-en-1-yl acetate, sodium 3-(cycloprop-2-en-1-yl)propanoate, sodium 3-(cycloprop-1-en-1-yl)propanoate, sidefungin, spermidine, spermines, strigolactones, tecnazenes, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tryptophan, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine, 2-chloro-N-(3-methoxyphenyl)-9H-purin-6-amine.

[0209] Further examples of useful combination partners for the compounds of the present invention represented by general formula (I) include the following safeners.

[0210] (S1) Equation (S1) [ka] wherein the symbols and indices are defined as follows: n Ais a natural number from 0 to 5, preferably a natural number from 0 to 3; R A 1 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl; W A is an unsubstituted or substituted divalent heterocyclic radical selected from the group of partially unsaturated or aromatic 5-membered heterocycles having 1 to 3 ring heteroatoms selected from the group of N and O, wherein at least one nitrogen atom and at most one oxygen atom is present in the ring, and preferably (W A 1 )~(W A 5 ) [ka] is a radical selected from the group m A is 0 or 1; R A 2 is OR A 3 , S.R. A 3 Or NR A 3 R A 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and up to three heteroatoms (preferably heteroatoms selected from the group consisting of O and S), wherein the heterocycle is linked to the carbonyl group in (S1) via a nitrogen atom and the heterocycle is unsubstituted or substituted with a radical selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenyl, preferably of the formula OR A 3 , formula NHR A 4 or a radical of formula N(CH3)2, in particular of formula OR A 3 is a radical represented by: RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical (preferably having a total of 1 to 18 carbon atoms); R A 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy or substituted or unsubstituted phenyl; R A 5 is H, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, cyano or COOR A 9 (where R A 9 is hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-hydroxyalkyl, (C3-C 12 )-cycloalkyl or tri-(C1-C4)-alkylsilyl); R A 6 , R A 7 , R A 8 are the same or different and are selected from hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C 12 )-cycloalkyl or substituted or unsubstituted phenyl; R A 10 is H, (C3-C 12 )-cycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted heteroaryl. A compound represented by the formula:

[0211] Preferably: (a) Compounds of the type dichlorophenylpyrazoline-3-carboxylic acid (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); (b) Derivatives of dichlorophenylpyrazolecarboxylic 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); (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); (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); (e) Compounds of the type 5-benzyl-2-isoxazoline-3-carboxylic acid or 5-phenyl-2-isoxazoline-3-carboxylic acid or of the type 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (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-carboxylic acid (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; (f) Compounds of the type triazolyloxyacetic acid derivatives (S1 f ), preferably compounds such as: {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}methyl acetate (S1-14), or {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (S1-15), or {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}methyl acetate (S1-16), or {[5-(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}methyl acetate (S1-17), {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (S1-17), or methyl {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-18), or {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (S1-19) (these are described in patent application WO2021105101).

[0212] (S2) Formula (S2) [ka] wherein the symbols and indices are defined as follows: R B 1 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl; n B is a natural number from 0 to 5, preferably a natural number from 0 to 3; R B 2 is OR B 3 , S.R. B 3 Or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and up to three heteroatoms (preferably heteroatoms selected from the group O and S), which heterocycle is linked to the carbonyl group in (S2) via a nitrogen atom and which heterocycle is unsubstituted or substituted with a radical selected from the group (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenyl, preferably of the formula OR B 3 , formula NHR B 4 or a radical of formula N(CH3)2, in particular of formula OR B 3 is a radical represented by: R B 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical (preferably having a total of 1 to 18 carbon atoms); R B 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy or substituted or unsubstituted phenyl; T Bis a (C1 or C2)-alkanediyl chain, which is unsubstituted or substituted by one or two (C1-C4)-alkyl radicals or by [(C1-C3)-alkoxy]carbonyl; Quinoline derivatives represented by the formula:

[0213] Preferably: (a) 8-Quinolineoxyacetic acid type compounds (S2 a ), preferably 1-methylhexyl (5-chloro-8-quinolinoxy)acetate ("cloquintocet-mexyl") (S2-1), (1,3-dimethyl-but-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), methyl (5-chloro-8-quinolinoxy)acetate (S2-6), allyl (5-chloro-8-quinolinoxy)acetate (S2-7), 2-(2-)-(5-chloro-8-quinolinoxy)acetate (5-chloro-8-quinolinoxy)acetic acid (S2-10), its hydrates and salts, such as its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, which are described in WO-A-2002 / 34048; (b) (5-chloro-8-quinolinoxy)malonic acid type compounds (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.

[0214] (S3) Equation (S3) [ka] wherein the symbols and indices are defined as follows: R C 1 is (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C3-C7)-cycloalkyl, preferably dichloromethyl; R C 2 , R C 3 are identical or different and are hydrogen, (C-C)-alkyl, (C-C)-alkenyl, (C-C)-alkynyl, (C-C)-haloalkyl, (C-C)-haloalkenyl, (C-C)-alkylcarbamoyl-(C-C)-alkyl, (C-C)-alkenylcarbamoyl-(C-C)-alkyl, (C-C)-alkoxy-(C-C)-alkyl, dioxolanyl-(C-C)-alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, or substituted or unsubstituted phenyl, or R C 2 and R C 3 together form a substituted or unsubstituted heterocyclic ring (preferably an oxazolidine ring, a thiazolidine ring, a piperidine ring, a morpholine ring, a hexahydropyrimidine ring or a benzoxazine ring). A compound represented by the formula: Preferably: Active ingredients of the dichloroacetamide type, 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) [supplied by Stauffer] (S3-2), "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) [supplied by 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) [supplied by PPG Industries] (S3-5), "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) [Supplier: Sagro-Chem] (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) [Supplier: Nitrokemia or Monsanto] (S3-7), "TI-35" (1-dichloroacetylazepane) [Supplier: TRI-Chemical RT] (S3-8), "diclonon" (Dicyclonone) or "BAS 145138" or "LAB 145138" (S3-9), ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) [Supplier: BASF], "Furilazol" or "MON" 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10) and its (R)-isomer (S3-11).

[0215] (S4) Equation (S4) [ka] wherein the symbols and indices are defined as follows: X D is CH or N; RD 1 is CO-NR D 5 R D 6 or NHCO-R D 7 and; R D 2 is halogen, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl; R D 3 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl; R D 4 is halogen, nitro, (C-C)-alkyl, (C-C)-haloalkyl, (C-C)-haloalkoxy, (C-C)-cycloalkyl, phenyl, (C-C)-alkoxy, cyano, (C-C)-alkylthio, (C-C)-alkylsulfinyl, (C-C)-alkylsulfonyl, (C-C)-alkoxycarbonyl or (C-C)-alkylcarbonyl; R D 5 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl, wherein the heterocyclyl is selected from the group consisting of nitrogen, oxygen and sulfur. Dcontaining 10 heteroatoms), wherein the last seven radicals mentioned are selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C2)-alkylsulfinyl, (C1-C2)-alkylsulfonyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl and phenyl, and in the case of cyclic radicals are additionally selected from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl, D substituted with a substituent of R D 6 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, where the last three mentioned radicals are selected from the group consisting of halogen, hydroxyl, (C1-C4)-alkyl, (C1-C4)-alkoxy and (C1-C4)-alkylthio. D or R D 5 and R D 6 together with the nitrogen atom bearing them form a pyrrolidinyl radical or a piperidinyl radical; R D 7 is hydrogen, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (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 in the case of cyclic radicals are additionally selected from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl, v D substituted with a substituent of n D is 0, 1 or 2; m D is 1 or 2; v Dis 0, 1, 2 or 3. N-acylsulfonamides represented by the formula: and salts thereof;

[0216] Among these, for example, those known from WO-A-97 / 45016, such as those of the following formula (S4 a ) [ka] [During the ceremony, R D 7 is (C1-C6)-alkyl or (C3-C6)-cycloalkyl, where the last two radicals are selected from the group consisting of halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio, and in the case of cyclic radicals are additionally selected from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl, v D substituted with a substituent of R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy or CF3; m D is 1 or 2; v D is 0, 1, 2 or 3. Preferred are compounds of the N-acylsulfonamide type represented by and, further, For example, compounds of the formula (S4 b )

[0217] [ka] For example, acylsulfamoylbenzamides represented by the formula: R D 5 = cyclopropyl, and (R D 4 ) = 2-OMe ("cyprosulfamide", S4-1); R D 5 = cyclopropyl, and (R D 4 ) = 5-Cl-2-OMe(S4-2); R D 5 = ethyl, and (R D 4 )=2-OMe(S4-3); R D 5 = isopropyl, and (R D 4 ) = 5-Cl-2-OMe (S4-4); and R D 5 = isopropyl, and (R D 4 )=2-OMe(S4-5); Also preferred are those and,

[0218] For example, the compound of formula (S4 c ) [ka] [During the ceremony, R D 8 and R D 9 are independently hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl or (C3-C6)-alkynyl; R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3; m D is 1 or 2] N-acylsulfamoylphenylurea type compounds represented by the formula: 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; Also preferred are:

[0219] (S5) Active ingredients (S5) selected from the class of hydroxyaromatic compounds and aromatic-aliphatic carboxylic acid derivatives, such as ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid (which are described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001).

[0220] (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-dihydroquinoxaline-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).

[0221] (S7) Formula (S7) (which is described in WO-A-1998 / 38856) [ka] wherein the symbols and indices are defined as follows: R E 1 , R E 2 are independently halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, nitro; A ECOOR E 3 or COSR E 4 and; R E 3 , R E 4 are independently hydrogen, (C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C4)-alkynyl, cyanoalkyl, (C1-C4)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium; n E 1 is 0 or 1; n E 2 , n E 3 are independently 0, 1 or 2. A compound represented by the formula: Preferably, diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1).

[0222] (S8) Formula (S8) (which is described in WO-A-98 / 27049) [ka] [During the ceremony, X F is CH or N; n F is X F =N, it is an integer from 0 to 4; and n F is X F When =CH, it is an integer from 0 to 5; R F 1is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, nitro, (C1-C4)-alkylthio, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy; R F 2 is hydrogen or (C1-C4)-alkyl; R F 3 is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, each of which carbon-containing radicals is unsubstituted or substituted with one or more (preferably up to three) identical or different radicals selected from the group consisting of halogen and alkoxy. A compound represented by the formula (I) or a salt thereof; Preferably, in the above formula: X F but CH; n F is an integer between 0 and 2; R F 1 is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy; R F 2 is hydrogen or (C1-C4)-alkyl; R F 3 is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, in which each of the carbon-containing radicals is unsubstituted or substituted with one or more (preferably up to three) identical or different radicals selected from the group consisting of halogen and alkoxy; A compound or a salt thereof.

[0223] (S9) An active ingredient (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.

[0224] (S10) Formula (S10 a ) or formula (S10 b ) (these are described in WO-A-2007 / 0237190 and WO-A-2007 / 023764) [ka] [During the ceremony, R G 1 is halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3; Y G , Z G represent, independently of one another, O or S; n G is an integer between 0 and 4; R G 2 is (C1-C 16 )-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl, benzyl, halobenzyl; R G 3 is hydrogen or (C1-C6)-alkyl] A compound represented by the formula:

[0225] (S11) Active ingredients of the oxyimino compound type (S11) (these are known as seed dressing compositions), such as "oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1) (which is known as a seed dressing safener for foxtail millet / sorghum against damage caused 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 foxtail millet against damage caused by metolachlor); and "siometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3) (which is known as a seed dressing safener for foxtail millet / sorghum against damage caused by metolachlor).

[0226] (S12) Active ingredients (S12) selected from the class of isothiochromanones, for example, 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).

[0227] (S13) One or more compounds selected from the following group: "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for corn against injury from thiocarbamate herbicides; "fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a seed dressing safener for pretilachlor in sown rice; "flurazole" (2-chloro-4-trifluoromethyl-1,3-thiazole-5-benzyl carboxylate) (S13-3), which is known as a seed dressing safener for foxtail millet against injury from alachlor and metolachlor; "CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) [Supplier: American Cyanamid] (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) (supplied by Nitrokemia) (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) (supplied by 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).

[0228] (S14) Active ingredients that have a herbicidal effect against harmful plants and also 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 rice safener for damage caused by the herbicide molinate); "Dymron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolyl urea) (known as a rice safener for damage caused by the herbicide imazosulfuron); "Cumylron" = "JC 940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl) urea; see JP-A-60087254) (known as a rice safener for damage caused by some herbicides); "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone) (known as a rice safener for damage caused by some herbicides); "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) [Supplier: Kumiai] (CAS Reg. No. 54091-06-4), which is known as a safener for some herbicide injury in rice.

[0229] (S15) Formula (S15) (which is described in WO-A-2008 / 131861 and WO-A-2008 / 131860) [ka] [During the ceremony, R H 1 is a (C1-C6)-haloalkyl radical; and R H 2 is hydrogen or halogen; and R H 3 , R H 4 are independently hydrogen, (C1-C 16 )-alkyl, (C2-C 16 )-alkenyl or (C2-C 16)-alkynyl, in which the last three radicals are each unsubstituted or substituted by one or more radicals selected from the group halogen, hydroxy, 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, in which the cycloalkyl is fused on one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring. or (C4-C6)-cycloalkenyl, which is fused at one ring edge to a 4- to 6-membered saturated or unsaturated carbocyclic ring, in which the last four radicals are each unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxy, 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 heterocyclic ring 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. A compound represented by the formula: or a tautomer thereof.

[0230] (S16) Active ingredients that are primarily used as herbicides but also have a phytotoxicity-reducing 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), 3,6-dichloro-2-methoxybenzoate 1-(ethoxycarbonyl)ethyl (lactidichlor-ethyl).

[0231] Biological Examples A. Post-emergence herbicidal activity and crop compatibility of selected compounds of general formula (I) Seeds of monocotyledonous and dicotyledonous weed and crop plants were placed in sandy loam in plastic or wood fiber pots, covered with soil, and cultivated under controlled growing conditions in a greenhouse. Two to three weeks after sowing, test plants were treated at the one-leaf stage. The green parts of the plants were sprayed with a compound of the present invention, formulated as a wettable powder (WP) or emulsifiable concentrate (EC), as an aqueous suspension or emulsion containing 0.5% additives, at a spray volume of 600 L / ha (conversion). After maintaining the test plants under optimal growing conditions in the greenhouse for approximately three weeks, the activity of the preparations was visually assessed compared with untreated controls. For example, 100% activity = plant death; 0% activity = similar to control plants.

[0232] The following Tables A1 to A13 show the effects of selected compounds of general formula (I) listed in Tables I.1 to I.33 against various harmful plants at application rates of 20 g / ha or less, obtained by the experimental methods described above.

[0233] The symbols "a," "b," and "c" indicate dose-dependent differences in the pests tested, all of which were identical except for the dose used. [Table 3]

[0234] [Table 4]

[0235] [Table 5]

[0236] [Table 6]

[0237] [Table 7]

[0238]

Table 8

[0239]

Table 9

[0240]

Table 10

[0241]

Table 11

[0242]

Table 12

[0243]

Table 13

[0244]

Table 14

[0245]

Table 15

[0246] Table 16

[0247]

Table 17

[0248] Table 18

[0249] Table 19

[0250] Table 20

[0251] Table 21

[0252] Table 22

[0253] Table 23

[0254] Table 24

[0255] Table 25

[0256] Table 26

[0257] Table 27

[0258] Table 28

[0259] Table 29

[0260] Table 30 Table 31

[0261] Table 32

[0262]

Table 33

[0263] Table 34

[0264] Table 35

[0265] Table 36

[0266] Table 37

[0267] Table 38

[0268] [Table 39]

[0269] Tables A14 to A17 below show the crop plant compatibility of selected compounds of general formula (I) listed in Tables I.1 to I.33 at application rates equivalent to 20 g / ha or less, obtained by the experimental procedures described above.

[0270] Here, the observed effects on selected crop plants are reported relative to untreated controls (values ​​in %).

[0271] The symbols "a," "b," and "c" indicate dose-dependent differences in test crop plants that were otherwise identical. [Table 40]

[0272] [Table 41]

[0273] [Table 42]

[0274] [Table 43]

[0275] [Table 44]

[0276] [Table 45]

[0277] [Table 46]

[0278] [Table 47]

[0279] As these results show, in the case of post-emergence treatment, the compounds of the present invention represented by the general formula (I) (a) have an effective control effect on harmful plants such as velvetleaf (Abutilon theophrasti) (ABUTH), black foxglove (Alopecurus myosuroides) (ALOMY), redroot pigweed (Amaranthus retroflexus) (AMARE), large crabgrass (Digitaria sanguinalis) (DIGSA), barnyardgrass (Echinochloa crus-galli) (ECHCG), komatsuna (Bassia scoparia) (KCHSC), burdock (Lolium rigidum) (LOLRI), chamomile (Tripleurospermum inodorum) (MATIN), common morning glory (Pharbitis (b) exhibits good herbicidal activity against organisms such as rice (Oryza sativa) (ORYSA), corn (Zea mays) (ZEAMX), soybean (Glycine max) (GLXMA), and wheat (Triticum aestivum) (TRZAS) at application rates of 0.02 kg per hectare or less.

[0280] B. Comparison of the post-emergence herbicidal activity and crop plant compatibility of selected exemplary compounds of the present invention (I.7-12, I.7-14, I.7-16) with structurally similar compounds known from the literature (WO2002 / 098227, structures "a-27" and "a-29"). Tables B1 to B5 below show the effects of the compounds of the present invention (I.7-12, I.7-14, I.7-16) obtained by the test method described above against various harmful plants at application rates equivalent to 20 g / ha or less, compared to structurally similar compounds known from the literature ("a-27" and "a-29" disclosed in WO2002 / 098227).

[0281] In this case, the tested compounds of the invention (I.7-12, I.7-14, I.7-16) each differ from the compounds known from the literature by an important structural feature, that is, by the incorporation of a methylene bridge (-CH2-) for the ester unit having the same "cycloalkyl group". [Table 48]

[0282] [Table 49]

[0283] [Table 50]

[0284] [Table 51]

[0285] [Table 52]

[0286] As shown in Tables B1 to B5, the compounds I.7-12, I.7-14 and I.7-16 of the present invention exhibit significantly improved herbicidal activity against harmful plants such as black foxtail (Alopecurus myosuroides) (ALOMY), barnyardgrass (Echinochloa crus-galli) (ECHCG), wild oat (Avena fatura) (AVEFA) and persica persica (VERPE) at application rates of 20 g per hectare or less, compared to the structurally similar compounds "a-27", "a-29" or structures generally encompassed therein known from the literature (WO 2002 / 098227).

[0287] Tables B6 to B10 below show the effects of the compounds of the present invention (I.7-12, I.7-14, I.7-16) obtained by the test methods described above, compared with structurally similar compounds known from the literature ("a-27" and "a-29" disclosed in WO2002 / 098227), on the crop plants rice (Oryza sativa) (ORYSA), corn (Zea mays) (ZEAMX) and wheat (Triticum aestivum) (TRZAS) at application rates equivalent to 5 g / ha or less. [Table 53]

[0288] [Table 54]

[0289] [Table 55]

[0290] [Table 56]

[0291] [Table 57]

[0292] As shown in Tables B6 to B10, the compounds of the present invention (I.7-12, I.7-14, I.7-16) show significantly improved compatibility with the crop plants rice (Oryza sativa) (ORYSA), corn (Zea mays) (ZEAMX) and wheat (Triticum aestivum) (TRZAS) at application rates of 5 g per hectare or less, in direct comparison with the structurally similar compounds "a-27", "a-29" or structures generally encompassed therein, known from the literature (WO2002 / 098227).

Claims

1. General formula (I) 【Chemical 1】 [During the ceremony, R １ is hydrogen, halogen, cyano, (C １ -C ８ )-alkyl, (C １ -C ８ )-haloalkyl, (C １ -C ８ )-alkoxy or (C １ -C ８ )-haloalkoxy; R ２ is hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C １ -C ８ )-alkoxy; R ３ is hydrogen, halogen or (C １ -C ８ )-alkoxy; R ４ is halogen, cyano, NO ２ , C(O)NH ２ , C(S)NH ２ , (C １ -C ８ )-haloalkyl or (C ２ -C ８ )-alkynyl; R ５ , R ６ and R ７ are independently hydrogen, halogen, cyano, (C １ -C ８ )-alkyl, (C １ -C ８ )-haloalkyl, (C １ -C ８ )-alkoxy or (C １ -C ８ )-haloalkoxy; G is an unbranched or branched (C １ -C ８ )-alkylene; Q is the formula 【Chemistry 2】 is a radical represented by R ８ is hydrogen, (C １ -C ８ )-alkyl or cyano; R ９ is hydrogen or (C １ -C ８ )-alkyl; R １０ is (C ３ -C ８ )-cycloalkyl (which is unsubstituted or in each case halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C ３ -C ６ )-cycloalkyl, (C １６ )-alkoxy, (C １６ )-substituted independently with "m" radicals selected from the group consisting of haloalkoxy, cyano, and nitro; or Spiro (C ５ -C ９ )-alkanyl or dispiro-(C ７ -C ８ )-alkanyl (which is unsubstituted or in any case halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C １ -C ６ )-alkoxy, (C １ -C ６ )-substituted independently with "m" radicals selected from the group consisting of haloalkoxy and cyano; m is 0, 1, 2 or 3; and, X and Y are independently O (oxygen) or S (sulfur). A substituted N-phenyluracil represented by the following formula: or a salt thereof.

2. R １ is hydrogen, halogen, cyano, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C １ -C ６ )-alkoxy or (C １ -C ６ )-haloalkoxy; R ２ is hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C １ -C ６ )-alkoxy; R ３ is hydrogen, halogen or (C １ -C ６ )-alkoxy; R ４ is halogen, cyano, NO ２ , C(O)NH ２ , C(S)NH ２ , (C １ -C ６ )-haloalkyl or (C ２ -C ６ )-alkynyl; R ５ , R ６ and R ７ are independently hydrogen, halogen, cyano, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C １ -C ６ )-alkoxy or (C １ -C ６ )-haloalkoxy; G is an unbranched or branched (C １ -C ６ )-alkylene; Q is the formula 【Chemistry 3】 is a radical represented by R ８ is hydrogen, (C １ -C ６ )-alkyl or cyano; R ９ is hydrogen or (C １ -C ６ )-alkyl; R １０ is (C ３ -C ７ )-cycloalkyl (which is unsubstituted or in each case halogen, (C １ -C ３ )-alkyl, (C １ -C ３ )-haloalkyl, (C ３ -C ６ )-cycloalkyl, (C １ -C ３ )-alkoxy, (C １ -C ３ )-substituted independently with "m" radicals selected from the group consisting of haloalkoxy, cyano, nitro; or Spiro (C ５ -C ７ )-alkanyl or dispiro-(C ７ -C ８ )-alkanyl (which is unsubstituted or in any case halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C １ -C ６ )-alkoxy; m is 0, 1, 2 or 3; and, X and Y are independently O (oxygen) or S (sulfur); The compound represented by the general formula (I) according to claim 1 and / or a salt thereof.

3. R １ is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl butyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy; R ２ is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, prop-1-yloxy, but-1-yloxy; R ３ is hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy; R ４ are fluorine, chlorine, bromine, cyano, NO ２ , C(O)NH ２ , C(S)NH ２ , trifluoromethyl, difluoromethyl, pentafluoroethyl, ethynyl, propyn-1-yl, 1-butyn-1-yl, pentyn-1-yl, hexyn-1-yl; R ５ , R ６ and R ７ are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1- ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy; G is methylene, (methyl)methylene, (ethyl)methylene, (prop-1-yl)methylene, (prop-2-yl)methylene, (but-1-yl)methylene, (but-2-yl)methylene, (pent-1-yl)methylene, (pent-2-yl)methylene, (pent-3-yl)methylene, (dimethyl)methylene, (diethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl propyl-1-ene, 3-methylpropyl-1-ene, 1,1-dimethylethyl-1-ene, 2,2-dimethylethyl-1-ene, 1-ethylethyl-1-ene, 2-ethylethyl-1-ene, 1-(prop-1-yl)ethyl-1-ene, 2-(prop-1-yl)ethyl-1-ene, 1-(prop-2-yl)ethyl-1-ene, 2-(prop-2-yl)ethyl-1-ene, 1,1,2-trimethylethyl-1-ene, 1,2,2-trimethylethyl-1-ene, 1,1,2,2-tetramethylethyl-1-ene ene, n-pentylene, 1-methylbutyl-1-ene, 2-methylbutyl-1-ene, 3-methylbutyl-1-ene, 4-methylbutyl-1-ene, 1,1-dimethylpropyl-1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl-1-ene, 1,2-dimethylpropyl-1-ene, 1,3-dimethylpropyl-1-ene, 1-ethylpropyl-1-ene, n-hexylene, 1-methylpentyl-1-ene, 2-methylpentyl-1-ene, 3-methylpentyl ... ethylpentyl-1-ene, 1,1-dimethylbutyl-1-ene, 1,2-dimethylbutyl-1-ene, 1,3-dimethylbutyl-1-ene, 2,2-dimethylbutyl-1-ene, 2,3-dimethylbutyl-1-ene, 3,3-dimethylbutyl-1-ene, 1-ethylbutyl-1-ene, 2-ethylbutyl-1-ene, 1,1,2-trimethylpropyl-1-ene, 1,2,2-trimethylpropyl-1-ene, 1-ethyl-1-methylpropyl-1-ene, 1-ethyl-2-methylpropyl-1-ene; X and Y are independently O (oxygen) or S (sulfur); and, Q is a partial structure Q-1 to Q-25 specifically described below: 【Chemistry 4】 where the arrows in the structural formulae in the table below represent the attachment of the respective Q group to the carbonyl group in general formula (I); The compound represented by the general formula (I) according to claim 1 and / or a salt thereof.

4. R １ is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy; R ２ is hydrogen, fluorine or chlorine; R ３ is hydrogen, fluorine, chlorine, bromine or methoxy; R ４ is fluorine, chlorine, bromine, cyano, NO ２ , C(O)NH ２ , C(S)NH ２ , trifluoromethyl, ethynyl or propyn-1-yl; R ５ , R ６ and R ７ are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, or trifluoromethoxy; G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, 1,1-dimethylethyl-1-ene, 2,2-dimethylethyl-1-ene, 1-ethylethyl-1-ene, 2-ethylethyl-1-ene, 1-(prop-1-yl)ethyl-1-ene, 2-(prop-1-yl) ethyl-1-ene, 1-(prop-2-yl)ethyl-1-ene, 2-(prop-2-yl)ethyl-1-ene, n-pentylene, 1-methylbutyl-1-ene, 2-methylbutyl-1-ene, 3-methylbutyl-1-ene, 4-methylbutyl-1-ene, 1,1-dimethylpropyl-1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl-1-ene, 1,2-dimethylpropyl-1-ene, 1,3-dimethylpropyl-1-ene, 1-ethylpropyl-1-ene or n-hexylene; X and Y are independently O (oxygen) or S (sulfur); and, Q is one of the partial structures Q-1 to Q-25 specifically described in claim 3; The compound represented by the general formula (I) according to claim 1 and / or a salt thereof.

5. R １ is hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy; R ２ is fluorine; R ３ is fluorine; R ４ are chlorine, bromine, cyano, NO ２ , C(O)NH ２ or C(S)NH ２ and R ５ , R ６ and R ７ are independently hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, or trifluoromethoxy; G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, n-pentylene or n-hexylene; X and Y are independently O (oxygen) or S (sulfur); and, Q is one of the partial structures Q-1 to Q-25 specifically described in claim 3; The compound represented by the general formula (I) according to claim 1 and / or a salt thereof.

6. R １ is hydrogen, fluorine, chlorine or bromine; R ２ is fluorine; R ３ is fluorine; R ４ is chlorine, bromine, cyano or NO ２ and R ５ is hydrogen, fluorine, chlorine or bromine; R ６ is hydrogen, fluorine, chlorine, bromine or cyano; R ７ is hydrogen, fluorine, chlorine or bromine; G is methylene, (methyl)methylene or (ethyl)methylene; X and Y are independently O (oxygen) or S (sulfur); and, Q is one of the partial structures Q-1 to Q-25 specifically described in claim 3; The compound represented by the general formula (I) according to claim 1 and / or a salt thereof.

7. R １ is hydrogen; R ２ is fluorine; R ３ is fluorine; R ４ is chlorine, bromine, cyano or NO ２ and R ５ is hydrogen; R ６ is hydrogen, fluorine, chlorine; R ７ is hydrogen; G is methylene, (methyl)methylene; X is O (oxygen) or S (sulfur); Y is O (oxygen); and, Q is one of the partial structures Q-1 to Q-25 specifically described in claim 3; The compound represented by the general formula (I) according to claim 1 and / or a salt thereof.

8. R １ is hydrogen; R ２ is fluorine; R ３ is fluorine; R ４ is chlorine, bromine or cyano; R ５ is hydrogen; R ６ is hydrogen or fluorine; R ７ is hydrogen; G is methylene; X is O (oxygen); Y is O (oxygen); and, Q is one of the substructures Q-1, Q-2, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-12, Q-13, Q-14, Q-15, Q-16, Q-18 or Q-19 specifically described in claim 3; The compound represented by the general formula (I) according to claim 1 and / or a salt thereof.

9. 10. Use of one or more compounds of general formula (I) and / or their salts as defined in any of claims 1 to 8 as herbicides and / or plant growth regulators, preferably in crops of useful plants and / or ornamental plants.

10. A herbicidal and / or plant growth regulating composition comprising one or more compounds of general formula (I) and / or salts thereof as defined in any one of claims 1 to 8; and (i) one or more further pesticidal active substances, preferably one or more further pesticidal active substances selected from the group consisting of insecticides, acaricides, nematicides, further herbicides, fungicides, safeners, fertilizers and / or further growth regulators; (ii) one or more formulation adjuvants customary in crop protection; comprising one or more further substances selected from group (i) and / or group (ii), including: The composition, characterized by:

11. 1. A method for controlling harmful plants or regulating plant growth, comprising: to the plant, the seed of the plant, the soil in or on which the plant is growing, or the cultivated area, an effective amount of * one or more compounds of general formula (I) as defined in any one of claims 1 to 8 and / or salts thereof; or * the composition according to claim 10; The method, characterized by applying

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