Substituted n-phenyluracils and salts thereof, and use thereof as herbicidal active substances

Abstract

The present invention relates to substituted N-phenyluracils of general formula (I) or salts thereof (formula I), wherein the radicals in general formula (I) correspond to the definitions given in the description, and to the use thereof as herbicides, in particular for controlling weeds and / or weed grasses in crops, and / or as plant growth regulators for influencing the growth of crops.

Description

[0001] Substituted N-phenyluracils and their salts and their use as herbicidal active ingredients. Description: The invention relates to the technical field of plant protection products, in particular to herbicides for the selective control of weeds and grass weeds in crops. Specifically, this invention relates to substituted N-phenyluracils and their salts, processes for their preparation, and their use as herbicides, in particular for controlling weeds and / or grass weeds in crops and / or as plant growth regulators for influencing the growth of crops.Previously known plant protection products for the selective control of weeds in crops or active substances for controlling undesirable plant growth sometimes have disadvantages in their use, either because they (a) have no or insufficient herbicidal activity against certain weeds, (b) have an insufficiently narrow spectrum of weeds that can be controlled with one active substance, (c) have insufficient selectivity in crops, and / or (d) have a toxicologically unfavorable profile. Furthermore, some active substances that can be used as plant growth regulators in some crops lead to undesirably reduced crop yields in others or are incompatible with the crop or only compatible within a narrow application rate range.Some of the known active ingredients cannot be produced economically on an industrial scale due to difficult-to-access precursors and reagents, or they possess insufficient chemical stability. For other active ingredients, the effect depends too strongly on environmental conditions, such as weather and soil conditions. The herbicidal activity of these known compounds, particularly at low application rates, and their tolerance to crops still require improvement. It is known from various publications that certain substituted N-linked 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 / 30661, WO96 / 35679, WO97 / 01541, WO98 / 25909, WO 2001 / 034575, WO2001 / 39597, WO2001 / 85907, However, the known aryluracils have several gaps in their activity, particularly against monocotyledonous weeds. A number of herbicidal active ingredient combinations based on N-linked aryluracils have also been disclosed (cf. DE4437197, EP714602, WO96 / 07323, WO96 / 08151, JP11189506, JP2003 / 104808, JP2003 / 104809, JP2003 / 104810, JP2003 / 160415, and JP2003 / 160416). However, the properties of these active ingredient combinations were not satisfactory in all respects.Also known are substituted uracils containing an N-linked and further substituted diaryl ether group or a corresponding heteroaryl ether residue (cf. US6333296, US6121201, WO2001 / 85907, EP1122244, EP1397958, EP1422227, WO 2002 / 098227). Furthermore, highly substituted N-phenyluracils with a specifically substituted carbonylalkyloxy group have been described (cf. WO2011 / 137088). WO2018 / 019842 describes the use of specifically substituted N-phenyluracils for controlling certain dicotyledonous weeds that exhibit specific resistance to established herbicides. Substituted 3-phenyl-5-alkyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-diones (cf. WO2019 / 101551) are also known.Surprisingly, it has now been found that selected N-phenyluracils with a substituted alkyl ester side chain or salts thereof are highly suitable as herbicides and can be used particularly advantageously as active ingredients for controlling monocotyledonous and dicotyledonous weeds in crops. The present invention thus relates to substituted N-phenyluracils of the general formula (I) or salts thereof. where R 1 represents hydrogen, halogen, cyano, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C8)alkoxy or (C1-C8)haloalkoxy, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C1-C8)-alkoxy, R 3 represents hydrogen, halogen or (C1-C8)-alkoxy, R 4 represents halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C8)-haloalkyl or (C2-C8)-alkynyl, R 5 , R 6 and R 7independently of one another represent hydrogen, halogen, cyano, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-alkoxy or (C1-C8)-haloalkoxy, G represents unbranched or branched (C1-C8)-alkylene, Q represents a radical of the formula R 8 represents hydrogen, (C1-C8)-alkyl or cyano, R 9 represents hydrogen or (C1-C8)-alkyl, R 10represents (C3-C8)-cycloalkyl, which is unsubstituted or substituted in each case independently by “m” radicals 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 represents spiro-(C5-C9)-alkanyl or dispiro-(C7-C8)-alkanyl, which are unsubstituted or substituted in each case independently by “m” radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy and cyano, m represents 0, 1, 2 or 3 and X and Y independently of one another represent O (oxygen) or S (sulfur). Particularly preferred subject matter of the invention are compounds of the general formula (I), wherein R 1 represents hydrogen, halogen, cyano, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy or (C1-C6)haloalkoxy, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C1-C6)-alkoxy, R3 represents hydrogen, halogen or (C1-C6)-alkoxy, R 4 represents halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C6)-haloalkyl or (C2-C6)-alkynyl, R 5 , R 6 and R 7 independently of one another represent hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy or (C1-C6)-haloalkoxy, G represents unbranched or branched (C1-C6)-alkylene, Q represents a radical of the formula, R 8 represents hydrogen, (C1-C6)-alkyl or cyano, R 9 represents hydrogen or (C1-C6)-alkyl, R 10represents (C3-C7)-cycloalkyl which is unsubstituted or in each case independently substituted by “m” radicals 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 represents spiro-(C5-C7)-alkanyl or dispiro-(C7-C8)-alkanyl which are unsubstituted or in each case independently substituted by “m” radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, m represents 0, 1, 2 or 3 and X and Y independently represent O (oxygen) or S (sulfur). A particularly preferred subject of the invention are compounds of the general formula (I), wherein R 1für Wasserstoff, Fluor, Chlor, Brom, lod, Cyano, Methyl, Ethyl, Prop-l-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-Di-methylbutyl, 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, l-Ethyl-2-methylpropyl, Trifluormethyl, Difluormethyl, Pentafluorethyl,

[0002] 2.2-Difluorethyl, 2,2,2-Trifluorethyl, Methoxy, Ethoxy, Prop-l-yloxy, Prop-2-yloxy, But-1- yloxy, But-2-yloxy, 2-Methylprop-l-yloxy, 1,1-Dimethyleth-l-yloxy, Difluormethoxy, Trifluormethoxy, Pentafluorethoxy, 2,2-Difluorethoxy, 2,2,2-Trifluorethoxy steht,

[0003] R 2represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, prop-l-yloxy, but-1-yloxy,

[0004] R 3 represents hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, prop-l-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-l-yloxy, 1,1-dimethyleth-l-yloxy,

[0005] R 4 represents 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-l-yl,

[0006] R 5 , R 6 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-l-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,

[0007] 2.2-Dimethylpropyl, 1 -Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1,3-Di-methylbutyl, 2,2-Dimethylbutyl,

[0008] 2.3-Dimethylbutyl, 3,3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1,1,2-Trimethylpropyl, 1,2,2- Trimethylpropyl, 1 -Ethyl- 1 -methylpropyl, l-Ethyl-2-methylpropyl, Trifluormethyl, Difluor- methyl, Pentafluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Methoxy, Ethoxy, Prop-l-yloxy, Prop-2-yloxy, But-l-yloxy, But-2-yloxy, 2-Methylprop-l-yloxy, 1,1-Dimethyleth-l-yloxy, Difluormethoxy, Trifluormethoxy, Pentafluorethoxy, 2,2-Difluorethoxy, 2,2,2-Trifluorethoxy stehen,

[0009] G für Methylen, (Methyl)methylen, (Ethyl)methylen, (Prop-l-yl)methylen, (Prop-2-yl)methylen, (But-l-yl)methylen, (But-2-yl)methylen, (Pent-l-yl)methylen, (Pent-2-yl)methylen, (Pent-3- yl)methylen, (Dimethyl)methylen, (Diethyl)methylen, Ethylen, n-Propylen, (l-Methyl)ethyl-l- en, (2-Methyl)ethyl-l-en, n-Butylen, 1 -Methylpropyl- 1 -en, 2-Methylpropyl- 1 -en, 3-Methyl- propyl-l-en, 1,1 -Dimethylethyl- 1 -en, 2,2-Dimethylethyl-l-en, 1 -Ethylethyl- 1 -en, 2-Ethylethyl- 1-en, l-(Prop-l-yl)ethyl-l-en, 2-(Prop-l-yl)ethyl-l-en, l-(Prop-2-yl)ethyl-l-en, 2-(Prop-2- yl)ethyl- 1 -en, 1 , 1 ,2-Trimethylethyl- 1 -en, 1 ,2,2-Trimethylethyl- 1 -en, 1 , 1 ,2,2-Tetramethylethyl- 1 - en, n-Pentylen, 1 -Methylbutyl- 1-en, 2-Methylbutyl-l-en, 3-Methylbutyl-l-en, 4-Methylbutyl-l- en, 1,1 -Dimethylpropyl- 1-en, 2,2-Dimethylpropyl-l-en, 3,3-Dimethylpropyl-l-en, 1,2- Dimethylpropyl- 1-en, 1,3-Dimethylpropyl-l-en, 1 -Ethylpropyl- 1 -en, n-Hexylen, 1-Methyl- pentyl-l-en, 2-Methylpentyl-l-en, 3-Methylpentyl-l-en,4-methylpentyl-l-ene, 1,1-dimethylbutyl-1-ene, 1,2-dimethylbutyl-l-ene, 1,3-dimethylbutyl-l-ene, 2,2-dimethylbutyl-l-ene, 2,3-dimethylbutyl-l-ene, 3,3-dimethylbutyl-l-ene, 1-ethylbutyl-1-ene, 2-Ethylbutyl-l-ene, 1,1,2-trimethylpropyl-l-ene, 1,2,2-trimethylpropyl-l-ene, 1-ethyl-1-methylpropyl-1-ene, l-ethyl-2-methylpropyl-1-ene,

[0010] X and Y independently represent O (oxygen) or S (sulfur) and

[0011] Q represents one of the following specifically named groups Q1 to Q-25, where in the structural formulas of the following table the arrow represents a bond of the respective group Q to the carbonyl group in the general formula (I):

[0012] 0 , 0 A 0 0 Particularly preferred subject matter of the invention are compounds of the general formula (I), wherein R 1represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, R 2 represents hydrogen, fluorine or chlorine, R 3 represents hydrogen, fluorine, chlorine, bromine or methoxy, R 4 represents fluorine, chlorine, bromine, cyano, NO2, C(O)NH2, C(S)NH2, trifluoromethyl, ethynyl or propyn-1-yl, R 5 , R 6 and R 7independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, G represents 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 independently of one another represent O (oxygen) or S (sulfur) and Q represents one of the groups Q-1 to Q-25 specifically mentioned above.The invention particularly relates to compounds of the general formula (I) in which R. 1 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, R 2 represents fluorine, R 3 represents fluorine, R 4 represents chlorine, bromine, cyano, NO2, C(O)NH2 or C(S)NH2, R 5 , R 6 and R 7independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, G represents 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 independently represent O (oxygen) or S (sulfur) and Q represents one of the groups Q-1 to Q-25 specifically mentioned above. Particularly preferred subject matter of the invention are compounds of the general formula (I), wherein R 1 represents hydrogen, fluorine, chlorine or bromine, R 2 represents fluorine, R 3 represents fluorine, R 4 represents chlorine, bromine, cyano or NO2,

[0013] R 5 represents hydrogen, fluorine, chlorine or bromine,

[0014] R 6 represents hydrogen, fluorine, chlorine, bromine or cyano,

[0015] R 7 represents hydrogen, fluorine, chlorine or bromine,

[0016] G stands for methylene, (methyl)methylene or (ethyl)methylene,

[0017] X and Y independently represent O (oxygen) or S (sulfur) and

[0018] Q stands for one of the groupings Q1 to Q-25 specifically mentioned above.

[0019] The most particularly preferred subject matter of the invention are compounds of the general formula (I) in which

[0020] R 1 stands for hydrogen,

[0021] R 2 stands for fluorine,

[0022] R 3 stands for fluorine,

[0023] R 4 represents chlorine, bromine, cyano or NO2,

[0024] R 5 stands for hydrogen,

[0025] R 6 represents hydrogen, fluorine, chlorine, bromine or cyano,

[0026] R 7 stands for hydrogen,

[0027] G stands for methylene or (methyl)methylene,

[0028] X stands for O (oxygen) or S (sulfur),

[0029] Y stands for O (oxygen) and Q stands for one of the groups Q1 to Q-25 specifically mentioned above.

[0030] The most particularly preferred subject matter of the invention are compounds of the general formula (I) in which

[0031] R 1 stands for hydrogen,

[0032] R 2 stands for fluorine,

[0033] R 3 stands for fluorine,

[0034] R 4 represents chlorine, bromine, cyano or NO2,

[0035] R 5 stands for hydrogen,

[0036] R 6 stands for hydrogen, fluorine, chlorine,

[0037] R 7 stands for hydrogen,

[0038] G stands for methylene, (methyl)methylene,

[0039] X stands for O (oxygen) or S (sulfur),

[0040] Y stands for O (oxygen) and

[0041] Q stands for one of the groupings Q1 to Q-25 specifically mentioned above.

[0042] In particular, the preferred subject matter of the invention are compounds of the general formula (I) in which

[0043] R 1 stands for hydrogen,

[0044] R 2 represents fluorine, R 3 stands for fluorine,

[0045] R 4 represents chlorine, bromine or cyano,

[0046] R 5 stands for hydrogen,

[0047] R 6 represents hydrogen or fluorine,

[0048] R 7 stands for hydrogen,

[0049] G stands for methylene,

[0050] X stands for O (oxygen),

[0051] Y stands for O (oxygen) and

[0052] Q stands for one of the above-specifically mentioned groups Q1, Q2, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q12, Q13, Q14, Q15, Q16, Q18 or Q19.

[0053] The above general or preferred radical definitions apply both to the end products of general formula (I) and, accordingly, to the starting materials or intermediates required for their preparation. These radical definitions can be combined with each other, including within the given preferred ranges.

[0054] Particularly for reasons of higher herbicidal activity, better selectivity and / or better preparability, compounds according to the invention of the general formula (I) mentioned or salts thereof or the use thereof according to the invention are of particular interest in which individual radicals have one of the preferred meanings already mentioned or mentioned below, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.

[0055] If the compounds can form tautomers through hydrogen shift that are not structurally covered by the general formula (I), these tautomers are nevertheless encompassed by the definition of the compounds of the general formula (I) according to the invention, unless a specific tautomer is considered. For example, many carbonyl compounds can exist in both the keto and enol forms, with both forms being encompassed by the definition of the compound of the general formula (I).

[0056] The compounds of general formula (I) can exist as stereoisomers depending on the nature and linkage of the substituents. The possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z- and E-isomers, are all encompassed by general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z- and E-isomers) can occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers can be obtained from the mixtures obtained during production using conventional separation methods. Chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or diastereomeric excess, and on a preparative scale to produce test samples for biological testing.Likewise, stereoisomers can be selectively prepared by employing stereoselective reactions using optically active starting materials and / or auxiliaries. The invention thus also relates to all stereoisomers encompassed by the general formula (I) but not specified with their specific stereoform, as well as mixtures thereof.

[0057] If the compounds are obtained as solids, purification can also be carried out by recrystallization or digestion. If individual compounds (I) are not satisfactorily accessible by the routes described below, they can be prepared by derivatization of other compounds (I).

[0058] Suitable methods for the isolation, purification, and stereoisomer separation of compounds of general formula (I) include methods generally known to the skilled person from analogous cases, e.g., physical processes such as crystallization, chromatography, especially column chromatography and HPEC (high-pressure liquid chromatography), distillation, optionally under reduced pressure, extraction, and other processes. Any remaining mixtures can generally be separated by chromatographic separation, e.g., on chiral solid phases. For preparative quantities or on an industrial scale, processes such as crystallization, e.g., of diastereomeric salts, which can be obtained from the diastereomer mixtures with optically active acids and, if acidic groups are present, with optically active bases, are suitable.

[0059] With regard to the compounds according to the invention, the designations used above and below are explained. These are familiar to the person skilled in the art and have, in particular, the meanings explained below: Unless defined otherwise, the general rule for the designation of chemical groups is that the bond to the skeleton or the remainder of the molecule is via the last-mentioned structural element of the chemical group in question, e.g., in the case of (C2-C8)-alkenyloxy, via the oxygen atom, and in the case of heterocyclyl-(C1-C8)-alkyl or (C1-C6)-alkoxy-(C1-C6)-alkoxy-(C1-C6)-alkyl, in each case via the C atom of the alkyl group. According to the invention, "alkylthio" - alone or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C1-C 10)-, (C1-C6)- oder (C1-C4)-Alkylthio, z.B. (aber nicht beschränkt auf) (C1-C6)-Alkyl- thio wie Methylthio, Ethylthio, Propylthio, 1-Methylethylthio, Butylthio, 1-Methylpropylthio, 2-Methyl- propylthio, 1,1-Dimethylethylthio, Pentylthio, 1-Methylbutylthio, 2-Methylbutylthio, 3-Methylbutylthio, 1,1-Dimethylpropylthio, 1,2-Dimethylpropylthio, 2,2-Dimethylpropylthio, 1-Ethylpropylthio, Hexylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1,1-Dimethylbutyl- thio, 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-Trimethyl- propylthio, 1-Ethyl-1-methylpropylthio und 1-Ethyl-2-methylpropylthio. „Alkoxy“ bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, z. B.(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-methyl-pentoxy, 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 bonded via an oxygen atom, alkynyloxy means an alkynyl radical bonded via an oxygen atom such as (C2-C6). 10 )-, (C2-C6)- or (C2-C4)-alkenoxy or (C3-C 10)-, (C3-C6)- or (C3-C4)-alkynoxy. “Alkylcarbonyl” (alkyl-C(=O)-), unless defined otherwise elsewhere, represents alkyl radicals which are bonded to the skeleton via -C(=O)-, such as (C1-C 10 )-, (C1-C6)- or (C1-C4)- alkylcarbonyl. The number of C atoms refers to the alkyl radical in the alkylcarbonyl group. “Alkoxycarbonyl (alkyl-OC(=O)-)”, unless defined otherwise elsewhere: Alkyl radicals that are bonded to the skeleton via -OC(=O)-, such as (C1-C 10 )-, (C1-C6)- or (C1-C4)-alkoxycarbonyl. The number of C atoms refers to the alkyl radical in the alkoxycarbonyl group. Analogously, "alkenyloxycarbonyl" and "alkynyloxycarbonyl", unless defined otherwise elsewhere, represent alkenyl or alkynyl radicals, respectively, which are bonded to the skeleton via -OC(=O)-, such as (C2-C 10 )-, (C2-C6)- or (C2-C4)-alkenyloxycarbonyl or (C3-C 10)-, (C3-C6)- or (C3-C4)-alkynyloxycarbonyl. The number of C atoms refers to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group. The term "alkylcarbonyloxy" (alkyl-C(=O)-O-) stands for alkyl radicals which are bonded to the skeleton via a carbonyloxy group (-C(=O)-O-), such as (C1-C 10 )-, (C1-C6)- or (C1-C4)-alkylcarbonyloxy. The number of C atoms refers to the alkyl radical in the alkylcarbonyloxy group. In abbreviations such as C(O)R 13 , C(O)OR 13 , OC(O)NR 11 R 12 , or C(O)NR 11 R 12 The abbreviation O in parentheses stands for an oxygen atom bonded to the adjacent carbon atom via a double bond. In abbreviations such as OC(S)OR 13 , OC(S)SR 14 , OC(S)NR 11 R 12, the abbreviation S in parentheses stands for a sulfur atom bonded to the adjacent carbon atom via a double bond. The term “aryl” means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl. The term “optionally substituted aryl” also includes multicyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the bonding site is on the aromatic system. From a systematic point of view, “aryl” is generally also included in the term “optionally substituted phenyl”.Bevorzugte Aryl-Substituenten sind hier zum Beispiel Wasserstoff, Halogen, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl, Arylalkyl, Arylalkenyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy, Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy, Alkenyloxy, Bis-alkylaminoalkoxy, Tris- [alkyl]silyl, Bis-[alkyl]arylsilyl, Bis-[alkyl]alkylsilyl, Tris-[alkyl]silylalkinyl, Arylalkinyl, Heteroaryl- alkinyl, Alkylalkinyl, Cycloalkylalkinyl, Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis-alkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonyl- amino, Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Hydroxycarbonyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Bis-Alkylaminocarbonyl, Heteroarylalkoxy, Arylalkoxy.A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring (carbocyclic ring) in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group consisting of N, O, S, P), which is saturated, unsaturated, partially saturated, or heteroaromatic and may be unsubstituted or substituted, the bonding site being located on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, polycyclic systems are also included, such as, 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 optionally substituted heterocyclyl, spirocyclic systems are also included, such as l-oxa-5-aza-spiro[2.3]hexyl.Unless defined otherwise, the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, although two oxygen atoms should not be directly adjacent, such as, for example, with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3-dihydro-1H-pyrrol-1- or 2- or 3- 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.

[0060] 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-lH-azepin-l- or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-Tetrahydro-lH-azepin-l- 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-lH-azepin-l- or 2- or 3- or 4-yl; 2,5-Dihydro-lH-azepin-l- or -2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-Dihydro-lH-azepin-l- 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-Dihydro-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;

[0061] 6- or 7-yl; 3H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4H-azepin-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

[0062] 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-dihydrothiophene-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-membered and 4-membered ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxetan-2-yl. Further examples of “heterocyclyl” are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O, and S, such as, for example, 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-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;

[0063] 4-yl; 1,6-Dihydropyriazin-l- or 3- or 4- or 5- or 6-yl; Hexahydropyrimidin-1- or 2- or 3- or 4-yl; 1,4,5,6-Tetrahydropyrimidin-l- 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-l- or 2- or 3- or 4- or 5- or 6-yl; 1,6-Dihydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 1,2-Dihydropyrimidin-l- 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-l- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-Piperazinyl; 1,2,3,6-Tetrahydropyrazin-l- or 2- or 3- or 5- or 6-yl; 1,2,3,4-Tetrahydropyrazin-

[0064] 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; l,3-Dioxolan-2- or 4- or 5-yl; l,3-Dioxol-2- or 4-yl; l,3-Dioxan-2- or 4- or 5-yl; 4H-l,3-Dioxin-2- or 4- or 5- or 6-yl; l,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; l,2-Dithiolan-3- or 4-yl; 3H-1,2-Dithiol-3- or 4- or 5-yl; l,3-Dithiolan-2- or 4-yl; 1,3-Dithiol-2- or 4-yl; l,2-Dithian-3- or 4-yl; 3,4-Dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-Dihydro-1,2-dithiin-3- or 4-yl; l,2-dithiin-3- or 4-yl; l,3-Dithian-2- or 4- or 5-yl; 4H-l,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; l,3-oxazolidin-2- or 3- or 4- or 5-yl; 2,3-Dihydro-l,3-oxazol-2- or 3- or 4- or 5-yl; 2,5-Dihydro-l,3-oxazol-;

[0065] 2- or 4- or 5-yl; 4,5-dihydro-l,3-oxazol-2- or 4- or 5-yl; l,2-oxazinan-2- or 3- or 4- or

[0066] 5- or 6-yl; 3,4-dihydro-2H-l,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-l,2-oxazin-2- or 3- or 4- or 5- or

[0067] 6-yl; 5,6-dihydro-4H-l,2-oxazin-3- or 4- or 5- or 6-yl; 2H-l,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-l,2-oxazin-3- or 4- or 5- or 6-yl; 4H-l,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-l,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-Dihydro-2H-l,3-oxazin-2- or 4- or 5- or 6-yl; 5,6-Dihydro-4H-l,3-oxazin-2- or 4- or 5- or 6-yl; 2H-l,3-oxazin-2- or 4- or 5- or 6-yl; 6H-l,3-oxazin-2- or 4- or 5- or 6-yl; 4H-l,3-oxazin-2- or 4- or 5- or 6-yl; Morpholin-2- or 3- or 4-yl; 3,4-Dihydro-2H-l,4-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-Dihydro-2H-l,4-oxazin-2- or 3- or 5- or 6-yl; 2H-l,4-oxazin-2- or 3- or 5- or 6-yl; 4H-l,4-oxazin-2- or 3-yl; l,2-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-Tetra-hydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,3,4,7-Tetrahydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-Tetrahydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-Tetrahydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4, 5,6,7-Tetrahydro-l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 2,3-Dihydro-l,2-oxazepin-2- or 3- or;

[0068] 4- or 5- or 6- or 7-yl; 2,5-Dihydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-Dihydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-Dihydro-l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 4,7-Dihydro-l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 6,7-Dihydro-

[0069] 1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl;

[0070] 1,3-Oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-Tetrahydro-l,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-Tetrahydro-l,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-Tetrahydro-l,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-Tetra-hydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-Tetrahydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,3-Dihydro-l,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-Dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-Dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5-Dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-Dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-Dihydro-l,3-oxazepine-2- or 4- or 5- or 6- or

[0071] 7-yl; l,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; l,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-l,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-l,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-l,4-oxazepine-2- or 3- or

[0072] 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-tetra- -hydro-l,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,7-dihydro-

[0073] 1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5-Dihydro-l,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,7-Dihydro-l,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 6,7-Dihydro-

[0074] 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; isothiazolidin-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-thiazolidin-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-l,3-thiazol-2- or 4- or 5-yl; 4,5-Dihydro-l,3-thiazol-2- or 4- or 5-yl; l,3-Thiazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-Dihydro-2H-l,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 3,6-Dihydro-2H-l,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 5,6-Dihydro-2H-l,3-thiazin-2- or 4- or 5- or 6-yl; 5,6-Dihydro-4H-l,3-thiazin-2- or 4- or 5- or 6-yl; 2H-l,3-Thiazin-2- or 4- or 5- or 6-yl; 6H-l,3-Thiazin-2- or 4- or 5- or 6-yl; 4H-l,3-Thiazin-2- or 4- or 5- or 6-yl.Further examples of “heterocyclyl” are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as, for example, 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-l,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-Dihydro-5H-l,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 5H-l,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 7H-l,4,2-dioxazepin-3- or 5- or 6- or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below:.

[0075] ) ) ) )( ) ) ) ( ) ) / / ) .

[0076] ' ,P •00 I 0 Die oben aufgeführten Heterocyclen sind bevorzugt beispielsweise durch Wasserstoff, Halogen, Alkyl, Haloalkyl, Hydroxy, Alkoxy, Cycloalkoxy, Aryloxy, Alkoxyalkyl, Alkoxyalkoxy, Cycloalkyl, Halocyclo-alkyl, Aryl, Arylalkyl, Heteroaryl, Heterocyclyl, Alkenyl, Alkylcarbonyl, Cycloalkyl- carbonyl, Arylcarbonyl, Heteroarylcarbonyl, Alkoxycarbonyl, Hydroxycarbonyl, Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Alkoxycarbonylalkyl, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkinyl, Alkinylalkyl, Alkylalkinyl, Tris-alkylsilylalkinyl, Nitro, Amino, Cyano, Haloalkoxy, Halo- alkylthio, Alkylthio, Hydrothio, Hydroxyalkyl, Oxo, Heteroarylalkoxy, Arylalkoxy, Heterocyclylalkoxy, Heterocyclylalkylthio, Heterocyclyloxy, Heterocyclylthio, Heteroaryloxy, Bis-alkylamino, Alkylamino, Cycloalkylamino, Hydroxycarbonylalkylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonyl- alkylamino, Alkoxycarbonylalkyl(alkyl)amino, Aminocarbonyl, Alkylaminocarbonyl, Bis-alkylamino- carbonyl, Cycloalkylaminocarbonyl,Hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl. If a basic structure is substituted "by one or more residues" from a list of residues (= group) or a generically defined group of residues, this includes simultaneous substitution by several identical and / or structurally different residues.

[0077] If it is a partially or fully saturated nitrogen heterocycle, it can be linked to the rest of the molecule via either carbon or nitrogen.

[0078] Possible substituents for a substituted heterocyclic radical are the substituents listed below, as well as oxo and thioxo. The oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring. This preferably also includes lactones and lactams. The oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, e.g., N and S, and then forms, for example, the divalent groups N(O), S(O) (also abbreviated SO) and S(O)2 (also abbreviated SO2) in the heterocyclic ring. In the case of -N(O)- and -S(O)- groups, both enantiomers are included.

[0079] According to the invention, the term “heteroaryl” stands for heteroaromatic compounds, ie completely unsaturated aromatic heterocyclic compounds, preferably for 5- to 7-membered rings with 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N. Heteroaryls according to the invention are, for example, IH-pyrrol-1-yl; IH-pyrrol-2-yl; IH-pyrrol-

[0080] 3-yl; furan-2-yl; furan-3-yl; thien-2-yl; Thien-3-yl, IH-imidazol-l-yl; lH-imidazol-2-yl; IH-imidazole

[0081] 4-yl; lH-Imidazol-5-yl; IH-Pyrazol-l-yl; lH-Pyrazol-3-yl; lH-Pyrazol-4-yl; lH-Pyrazol-5-yl, 1H-1,2,3- Triazol-l-yl, lH-l,2,3-Triazol-4-yl, lH-l,2,3-Triazol-5-yl, 2H-l,2,3-Triazol-2-yl, 2H-l,2,3-Triazol-4-yl, lH-l,2,4-Triazol-l-yl, lH-l,2,4-Triazol-3-yl, 4H-l,2,4-Triazol-4-yl, l,2,4-Oxadiazol-3-yl, 1,2,4-Oxa- diazol-5-yl, l,3,4-Oxadiazol-2-yl, l,2,3-Oxadiazol-4-yl, l,2,3-Oxadiazol-5-yl, l,2,5-Oxadiazol-3-yl, Azepinyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, l,3,5-Triazin-2-yl, l,2,4-Triazin-3-yl, l,2,4-Triazin-5-yl, l,2,4-Triazin-6-yl, l,2,3-Triazin-4-yl, l,2,3-Triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- und 1,2,6-Oxazinyl, Isoxazol-3-yl, Isoxazol-4-yl, Isoxazol-5-yl, l,3-Oxazol-2-yl, l,3-Oxazol-4-yl, 1,3- Oxazol-5-yl, Isothiazol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, l,3-Thiazol-2-yl, l,3-Thiazol-4-yl, 1,3- Thiazol-5-yl, Oxepinyl, Thiepinyl, 1,2,4-Triazolonyl und 1,2,4-Diazepinyl,2H-l,2,3,4-tetrazol-5-yl, lH-l,2,3,4-tetrazol-5-yl, l,2,3,4-oxatriazol-5-yl, l,2,3,4-thiatriazol-5-yl, l,2,3,5-oxatriazol-4-yl, l,2,3,5-thiatriazol-4-yl. The heteroaryl groups according to the invention can further be substituted with one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, these are fused heteroaromatic systems, such as benzofused or multiply fused heteroaromatics.

[0082] Bevorzugt sind beispielsweise Chinoline (z. B. Chinolin-2-yl, Chinolin-3-yl, Chinolin-4-yl, Chinolin-5- yl, Chinolin-6-yl, Chinolin-7-yl, Chinolin- 8 -yl); Isochinoline (z. B. Isochinolin- 1-yl, Isochinolin-3-yl, Isochinolin-4-yl, Isochinolin-5-yl, Isochinolin-6-yl, Isochinolin-7-yl, Isochinolin- 8 -yl); Chinoxalin; Chinazolin; Cinnolin; 1,5-Naphthyridin; 1,6-Naphthyridin; 1,7-Naphthyridin; 1,8-Naphthyridin; 2,6- Naphthyridin; 2,7-Naphthyridin; Phthalazin; Pyridopyrazine; Pyridopyrimidine; Pyridopyridazine; Pteridine; Pyrimidopyrimidine. Beispiele für Heteroaryl sind auch 5- oder 6-gliedrige benzokondensierte Ringe aus der Gruppe 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-Benzo- thiophen-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-Iso- indol-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-Benzthiazol-2-yl, 1,3-Benzthiazol- 4-yl, 1,3-Benzthiazol-5-yl, 1,3-Benzthiazol-6-yl, 1,3-Benzthiazol-7-yl, 1,2-Benzisoxazol-3-yl, 1,2- Benzisoxazol-4-yl, 1,2-Benzisoxazol-5-yl, 1,2-Benzisoxazol-6-yl, 1,2-Benzisoxazol-7-yl, 1,2-Benziso- thiazol-3-yl, 1,2-Benzisothiazol-4-yl, 1,2-Benzisothiazol-5-yl, 1,2-Benzisothiazol-6-yl, 1,2-Benziso- thiazol-7-yl. Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor,Bromine or iodine. If the term is used for a radical, then "halogen" means, for example, a fluorine, chlorine, bromine, or iodine atom. According to the invention, "alkyl" means a straight-chain or branched, open-chain, saturated hydrocarbon radical, which is optionally mono- or polysubstituted and, in the latter case, is referred to as "substituted alkyl." Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino, or nitro groups; particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine, or iodine. The prefix "bis" also includes the combination of different alkyl radicals, e.g., methyl(ethyl) or ethyl(methyl). “Haloalkyl”, “-alkenyl” and “-alkynyl” mean alkyl, alkenyl or alkynyl which are partially or fully substituted by identical or different halogen atoms, e.g. monohaloalkyl (= monohaloalkyl) such as CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl,CH2F; Perhaloalkyl such as CCl3, CClF2, CFCl2, CF2CClF2, CF2CClFCF3; Polyhaloalkyl such as CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3; The term perhaloalkyl also includes the term perfluoroalkyl. "Haloalkoxy" is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3, and OCH2CH2Cl; The same applies to haloalkenyl and other halogen-substituted radicals. The term "(C1-C4)-alkyl" used here as an example is a shorthand notation for straight-chain or branched alkyl with one to four carbon atoms according to the range specified for C atoms, i.e., it includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl, or tert-butyl. General alkyl radicals with a larger specified range of C atoms, e.g., "(C1-C6)-alkyl," correspondingly also include straight-chain or branched alkyl radicals with a larger number of C atoms, i.e., according to the example, also the alkyl radicals with 5 and 6 C atoms. Unless specifically stated,For hydrocarbon radicals such as alkyl, alkenyl, and alkynyl radicals, even in compound radicals, lower carbon skeletons, e.g., those with 1 to 6 C atoms, or for unsaturated groups with 2 to 6 C atoms, are preferred. Alkyl radicals, even in compound radicals such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t-, or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl, and 1,3-dimethylbutyl, and heptyls, such as n-heptyl, 1-methylhexyl, and 1,4-dimethylpentyl. Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, containing at least one double bond or triple bond. Preferred are radicals with one double bond or triple bond. The term "alkenyl" includes, in particular, straight-chain or branched open-chain hydrocarbon radicals with more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl.but also allenyl or cumulenyl residues with one or more cumulated double bonds, such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl. Alkenyl means, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not limited to) (C2-C6)-alkenyl such as 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, 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. The term "alkynyl" also includes, in particular, straight-chain or branched open-chain hydrocarbon radicals with more than one triple bond or with one or more triple bonds and one or more double bonds, such as 1,3-butatrienyl or 3-penten-1-yn-1-yl. (C2-C6)-alkynyl means, 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-pentynyl, 1-Methyl-4-pentynyl, 2-Methyl-3-pentynyl, 2-Methyl-4-pentynyl, 3-Methyl-1-pentynyl, 3-Methyl-4-pentynyl, 4-Methyl-1-pentynyl, 4-Methyl-2-pentynyl, 1,1-Di-methyl-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. The term "cycloalkyl" means a carbocyclic, saturated ring system with preferably 3-8 ring carbon atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, or cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, including substituents with a double bond on the cycloalkyl radical, e.g., an alkylidene group such as methylidene. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems are also included.such as 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, 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, but also systems such as. B.1,1'-Bi(cyclopropyl)-1-yl, 1,1'-Bi(cyclopropyl)-2-yl. The term "(C3-C7)-cycloalkyl" is a shorthand for cycloalkyl with three to seven carbon atoms, corresponding to the range for C atoms. In the case of spiro-(C5-C9)-alkanyl, spirocyclic aliphatic systems are also included, 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, and spiro[3.3]heptan-2-yl. In the case of dispiro-(C7-C8)-alkanyl, dispirocyclic aliphatic systems are included, such as 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. “Cycloalkenyl” means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, which also includes substituents with a double bond on the cycloalkenyl radical, e.g. an alkylidene group such as methylidene. In the case of optionally substituted cycloalkenyl, the explanations for substituted cycloalkyl apply accordingly. The term “alkylidene”, e.g. also in the form (C1-C 10)-Alkylidene, means the residue of a straight-chain or branched open-chain hydrocarbon residue that is bonded via a double bond. Naturally, only positions on the parent structure where two H atoms can be replaced by the double bond are possible as bonding sites for alkylidene; examples of residues are, for example, =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5, or =C(C2H5)-C2H 5.Cycloalkylidene means a carbocyclic radical bonded via a double bond. The term "alkylene", e.g. also in the form (C1-C8)-alkylene, means the radical of a straight-chain or branched open-chain hydrocarbon radical bonded to other groups at two positions. "Alkoxyalkyl" stands for an alkoxy radical bonded via an alkyl group, and "alkoxyalkoxy" means an alkoxyalkyl radical bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy. "Arylalkyl" stands for an aryl radical bonded via an alkyl group, "heteroarylalkyl" means a heteroaryl radical bonded via an alkyl group, and "heterocyclylalkyl" means a heterocyclyl radical bonded via an alkyl group. "Cycloalkylalkyl" stands for a cycloalkyl radical bonded via an alkyl group, e.g.(but not limited to) Cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl. "Arylalkenyl" means an aryl radical attached via an alkenyl group, "heteroarylalkenyl" means a heteroaryl radical attached via an alkenyl group, and "heterocyclylalkenyl" means a heterocyclyl radical attached via an alkenyl group. "Arylalkynyl" means an aryl radical attached via an alkynyl group, "heteroarylalkynyl" means a heteroaryl radical attached via an alkynyl group, and "heterocyclylalkynyl" means a heterocyclyl radical attached via an alkynyl group. According to the invention, "haloalkylthio" - alone or as part of a chemical group - stands for straight-chain or branched S-haloalkyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, such as (C1-C8)-, (C1-C6)- or (C1-C4)-haloalkylthio, e.g.(but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio. “Halocycloalkyl” and “halocycloalkenyl” mean radicals substituted by the same or different halogen atoms, such as F, Cl and Br, or by haloalkyl, such as B. Trifluoromethyl or difluoromethyl partially or fully substituted cycloalkyl or cycloalkenyl, e.g. 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. Synthesis of substituted N-phenyluracils of the general formula (I). The substituted N-phenyluracils of the general formula (I) according to the invention can be prepared starting from known processes.The synthetic routes used and investigated start from commercially available or readily prepared heteroaromatic amines and appropriately substituted hydroxy esters. The groups G, Q, and R. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7, X and Y of the general formula (I) have the previously defined meanings in the following schemes, unless exemplary but non-limiting definitions are given. As the first key intermediate for the synthesis of the compounds of the general formula (Ia) according to the invention, in which X stands for sulfur (S) and Y for oxygen (O), an optionally further substituted mercaptophenyl-1H-pyrimidine-2,4-dione is prepared. By way of example but not by way of limitation, this is shown in 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, by way of example but not by way of limitation, 2-fluoro-4-chloroaniline, is reacted with a suitable reagent (e.g. triphosgene) in a suitable polar aprotic solvent (e.g.Dichloromethane) into the corresponding isocyanate, which in the next step is converted into the corresponding optionally further substituted pyrimidine-2,4-dione, by reaction with a suitable aminoacrylic acid ester using a suitable base (e.g. sodium hydride or potassium tert-butoxide) in a suitable polar aprotic solvent (e.g. N,N-dimethylformamide), by way of example but not by way of limitation, 3-(4-chloro-2-fluorophenyl)-l-methyl-6-trifluoromethyl-lH-pyrimidine-2,4-dione (Scheme 1). By subsequent sulfochlorination with a suitable reagent (e.g. chlorosulfonic acid) and subsequent reduction with a suitable reducing agent (e.g. Zn in EtOH and HCl, tin(II) chloride hydrate or triphenylphosphine), the desired mercaptophenyl-lH-pyrimidine-2,4-dione, by way of example but not by way of limitation, 3-(4-chloro-2-fluoro-5-mercaptophenyl)-l-methyl-6-trifluoromethyl-lH-pyrimidine-2,4-dione (IIa), can be prepared (cf.KR1345394; EPI 122244; EP408382; WO 2003 / 029226; W02010 / 038953; US2011 / 0224083; KR2011 / 110420). In Scheme 1 below, R. 2 and R 3 by way of example, but not by way of limitation, for fluorine, R 4 by way of example, but not limitation, of chlorine and X by way of example, but not limitation, of sulfur.

[0083] Scheme 1.

[0084] The synthesis of the key intermediate (Ila) described in Scheme 1 can also be applied to the preparation of similar intermediates. The intermediate further substituted N-methyl-5-mercaptophenyl-1H-pyrimidine-2,4-diones (II) in question can then be converted into the desired compounds of the invention of the general formula (Ia) in which X is sulfur (S) and Y is oxygen (O) in various ways (Scheme 2), after the compounds (II) have been converted in a first step with the aid of a suitable, optionally further substituted iodophenol using a suitable base 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) and a suitable base (e.g. diisopropyl(ethyl)amine) in a suitable polar aprotic solvent (e.g. dioxane) to give intermediates (III).In the following scheme 2, Q, R 2 , R 3 and R 4 the above meanings according to the invention. Furthermore, R 1 , R 5 , R 6 , R 7by way of example but not limitation for hydrogen, X by way of example but not limitation for sulfur, Y by way of example but not limitation for oxygen and G by way of example but not limitation for CH2. The corresponding intermediate (III) described by way of example but not limitation in Scheme 2 can be converted into a corresponding intermediate oxyalkanoic ester (IVa, IVb) or the desired target compounds of the general formula (Ia) by reaction with a suitable, optionally further substituted iodoalkanoic ester (in Scheme 3 by way of example but not limitation an iodoacetic ester) using a suitable base (e.g. silver(I) carbonate) in a suitable polar aprotic solvent (e.g. n-hexane or cyclohexane) at elevated temperature (e.g. under microwave conditions) (cf. Synthesis 2009, 2725). The corresponding iodoalkanoic esters can be prepared using routes known from the literature (cf. Eur. J. Org. Chem., 2006, 71, 8459; WO2012 / 037573; Organometallics, 2009, 28, 132).

[0085] Schema 2

[0086] The intermediate ethyl esters (IVa) and tert-butyl esters (IVb) can then be converted into the corresponding free acid (V) under suitable reaction conditions [use of a suitable acid such as hydrochloric acid or acetic acid in the case of (IVa) or trifluoroacetic acid (TFA) in the case of (IVb)]. By reaction of the corresponding intermediate acid (V) with a suitable compound QH mediated by suitable coupling reagents (e.g. HOBt = 1-hydroxybenzotriazole, EDC = l-ethyl-3-(3-dimethylaminopropyl)carbodiimide, HATU = O-(7-azabenzotriazol-l-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, T3P = 2,4,6-tripropyl-l,3,5,2,4,6-trioxa-triphosphorinane-2,4,6-trioxide) and suitable bases (e.g. diisopropylethylamine, triethylamine) in a suitable polar aprotic solvent (e.g. dichloromethane, chloroform), the desired substituted N-phenyluracils of the general formula (Ia) can be prepared.Alternatively, the ethyl ester (IVa) can be converted into the corresponding desired substituted N-phenyluracil of general formula (Ia) by coupling with a suitable compound QH mediated by a suitable Lewis acid (e.g. indium(III) chloride) (cf. WO2011 / 1307088).

[0087] The preparation of the compounds of general formula (I), in which X and Y are, by way of example but not limitation, oxygen (O), proceeds via the synthesis of key intermediates (VI) with a fluorine substituent at position 5, such as 3-(2,5-difluoro-4-nitro)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (Via). For this purpose, a suitable substituted aniline, by way of example but not limitation, 2,5-difluoroaniline, is converted into the corresponding isocyanate using a suitable reagent (e.g. triphosgene) in a suitable polar aprotic solvent (e.g. dichloromethane), which in the next step is prepared by reaction with a suitable aminoacrylic acid ester using a suitable base (e.g. sodium hydride or potassium tert-butoxide) in a suitable polar aprotic solvent (e.g.N,N-Dimethylformamide) into the corresponding optionally further substituted pyrimidine-2,4-dione, here by way of example but not limitation, 3-(2,5-difluorophenyl)-6-trifluoromethyl-lH-pyrimidine-2,4-dione (Scheme 3). Nitration with a suitable nitrating reagent and subsequent N-methylation with a suitable methylating reagent gives the desired intermediate, here by way of example but not limitation 3-(2,5-difluoro-4-nitro)-l-methyl-6-trifluoromethyl-lH-pyrimidine-2,4-dione (Via). In the following Scheme 3, R. 2 and R 3 exemplary, but not restrictive, for fluorine and R 4 exemplary, but not restrictive for Nitro.

[0088] Scheme 3. The intermediate (VI) obtained in the manner described above, e.g., compound (Via), can then be converted into a desired substituted N-phenyluracil (Ib, R) with a suitable substituted 2-carbonylalkyloxy-l-hydroxybenzene (VII) using a suitable base (e.g., potassium carbonate) in a suitable polar aprotic solvent (e.g., N,N-dimethylformamide (DMF)). 4= Nitro). The intermediate (VII) used for this purpose can be prepared by multi-step synthesis starting from commercially available l-chloro-2-nitrobenzene via (i) base-mediated coupling (e.g. with sodium hydride) with a suitable substituted hydroxyalkylcarbonyl reagent in a suitable polar aprotic solvent (e.g. tetrahydrofuran or dioxane) or alternatively by reaction of 2-nitrophenol with a suitable substituted chloromethylcarbonyl reagent, (ii) reduction of the nitro group with a suitable reducing agent (e.g. hydrogen, palladium on carbon in a suitable polar protic solvent), (iii) diazotization (with a suitable diazotizing reagent, e.g. tert-butyl nitrite (t-BuONO), boron trifluoride etherate (BF3-OEt2) in suitable polar aprotic solvents (e.g. dichloromethane (DCM), dimethoxyethane), (iv) reaction with acetic anhydride and (v) Release of the hydroxy group by cleavage of the acetyl protecting group (e.g.base-mediated with potassium carbonate in a polar protic solvent). The nitro group in compound (Ib) can then be converted into a halogen substituent (e.g., chlorine, bromine) by reduction and subsequent Sandmeyer reaction, thus yielding the desired substituted N-phenyluracil (Ic). In Scheme 4 below, Q and R. 2 the above meanings according to the invention. Furthermore, R 3 by way of example, but not by way of limitation, for fluorine, R 4 by way of example, but not by way of limitation, for chlorine or nitro, R 1 , R 5 , R 6 , R 7 by way of example but not limitation, hydrogen, X and Y by way of example but not limitation, oxygen and G by way of example but not limitation, CH2.

[0089] Scheme 4. The intermediate (VI) obtained in the manner described above can be converted into a desired substituted N-phenyluracil (Id, R 4 = nitro) with X=O (oxygen) and Y=S (sulfur). The intermediate (VIII) used for this purpose can be prepared by a multi-step synthesis analogous to the synthesis of intermediate (VII) described in Scheme 4 starting from commercially available l-chloro-2-nitrobenzene or 2-nitrothiophenol. The nitro group in compound (Id) can then be converted into a halogen substituent (e.g., chlorine, bromine) by reduction and subsequent Sandmeyer reaction, thus yielding the desired substituted N-phenyluracil (le). In the following Scheme 5, Q and R2 the above meanings according to the invention. Furthermore, R 3 by way of example, but not by way of limitation, for fluorine, R 4 by way of example, but not by way of limitation, for chlorine or nitro, R 1 , R 5 , R 6 , R 7 by way of example but not limitation, hydrogen, X by way of example but not limitation, oxygen, Y by way of example but not limitation, sulfur and G by way of example but not limitation, CH2.

[0090] Scheme 5.

[0091] The intermediate further substituted N-methyl-5-mercaptophenyl-1H-pyrimidine-2,4-diones (II) can also be converted into the desired compounds according to the invention of the general formula (If), in which X and Y represent sulfur (S) (Scheme 6), after the compounds (III) have been reacted in a first step with the aid of a suitable optionally further substituted iodo-thiophenol using a suitable base 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) and a suitable base (e.g. diisopropyl(ethyl)amine) in a suitable polar aprotic solvent (e.g. dioxane) to give intermediates of type (IX). If necessary, intermediate cleavage of the thiol group using a suitable protecting group is required.The intermediates (IX) can then be reacted with differently substituted haloalkanecarboxylic acids using suitable bases to give the desired compounds of general formula (If). In Scheme 6 below, Q, R. 2 , R 3 , and R 4 the above meanings according to the invention. Furthermore, R 1 , R 5 , R 6 , R 7 by way of example but not limitation, hydrogen; X and Y by way of example but not limitation, sulfur; and G by way of example but not limitation, CH2. Furthermore, for greater clarity, the reaction pathways in Scheme 6 below are described by way of example but not limitation, using iodoacetic acid esters. Comparable haloalkanecarboxylic acids (halogen = bromine or chlorine) are also suitable for coupling with intermediate (IX).

[0092] Scheme 6. Selected detailed synthesis examples for the compounds of the general formula (I) according to the invention are listed below. The example numbers given correspond to the numberings given in Tables I.1 to I.33 below. 1 H-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz at 1H-NMR (CDCl3, CD3OD, or d6-DMSO solvent, internal standard: tetramethylsilane, δ = 0.00 ppm) was obtained using a Bruker instrument. The designated signals have the following meanings: br = broad; s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of a double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. For mixtures of diastereomers, either the significant signals of both diastereomers or the characteristic signal of the major diastereomer are given. The abbreviations used for chemical groups have the following meanings: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl. Synthesis examples: Example I.7-2: 1-Cyclopropylethyl-(2-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetat. 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 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 stirred for 4 hours at room temperature. Water and dichloromethane were added to the reaction mixture, the aqueous phase was extracted several times with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed in vacuo. Purification by column chromatography on silica gel using an n-heptane / ethyl acetate gradient yielded 0.122 g (71% of theory) of a colorless solid. 1H-NMR (CDCI3δ, 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).

[0093] Bspl. I.7-10: Cyclobutylmethyl-(2-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin- 1 (2H)-yl]phenoxy}phenoxy)acetat

[0094] 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-l(2H)-yl]phenyl}sulfanyl)phenoxy]acetic acid (0.150 g, 0.292 mmol) followed by 1-hydroxy-1H-benzotriazole hydrate (0.058 g, 0.379 mmol), l-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (0.073 g, 0.379 mmol) and 4-dimethylaminopyridine (10 mol%) and stirred for 4 hours at room temperature. The reaction mixture was treated with water and dichloromethane, the aqueous phase was extracted several times with dichloromethane, the combined organic phases were dried over sodium sulfate and the solvent was removed in vacuo.

[0095] After column chromatographic purification on silica gel with an n-heptane / ethyl acetate gradient, 0.139 g (81% of theory) of a colorless solid was obtained.

[0096] ’H-NMR (CDCI3δ, 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).

[0097] Bspl. I.7-18: Spiro[2.2]pentan-l-ylmethyl-(2-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)- 3,6-dihydropyrimidin- 1 (2H)-yl]phenoxy}phenoxy)acetat

[0098] To a solution of spiro[2.2]pentan-l-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-l(2H)-yl]phenyl}sulfanyl)phenoxy]acetic acid (0.170 g, 0.330 mmol) followed by 1-hydroxy-IH-benzotriazole hydrate (0.066 g, 0.430 mmol), l-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (0.082 g, 0.043 mmol) and 4-dimethylaminopyridine (10 mol%) and stirred for 2 hours at room temperature. The reaction mixture was treated with water and dichloromethane, the aqueous phase was extracted several times with dichloromethane, the combined organic phases were dried over sodium sulfate and the solvent was removed in vacuo.

[0099] After column chromatographic purification on silica gel with an n-heptane / ethyl acetate gradient, 0.170 g (86% of theory) of a colorless solid was obtained. 1H-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).

[0100] Bspl. I.8-1 : Cyclopropylmethyl-(2-{2-brom-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6- dihydropyrimidin- 1 (2H)-yl]phenoxy}phenoxy)acetat

[0101] 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-l(2H)-yl]phenoxy}phenoxy)acetic acid (450 mg, 0.84 mmol) followed by 1-hydroxy-1H-benzotriazole hydrate (148 mg, 1.10 mmol), l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (210 mg, 1.10 mmol) and catalytic amounts of 4-dimethylaminopyridine (10 mg) and stirred for 5 hours at room temperature. The reaction mixture was allowed to stand overnight and subsequent thin-layer chromatographic reaction control showed incomplete conversion, so that 1-hydroxy-IH-benzotriazole hydrate (148 mg, 1.10 mmol), l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (210 mg, 1.10 mmol) and catalytic amounts of 4-dimethylaminopyridine (10 mg) were added again.The reaction mixture was stirred for a further 5 hours at room temperature, and almost complete conversion was determined by thin-layer chromatography. 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 column chromatography on silica gel using an n-heptane / ethyl acetate gradient yielded 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) as a colorless oil. 1 H-NMR (CDCI3δ, 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).

[0102] E.g. I.9-1: Cyclopropylmethyl-(2-{2-cyan-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate

[0103] 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) was initially charged with zinc cyanide (69 mg, 0.59 mmol) and tetrakis(triphenylphosphine)palladium (0) (65 mg, 0.06 mmol) under argon in 10 mL of N,N-dimethylacetamide and stirred for 1 hour at an oil bath temperature of 180 °C. After TLC monitoring, which indicated complete conversion, the reaction mixture was added to 10 mL of water and extracted several times with ethyl acetate. The combined organic phases were washed twice with saturated brine, dried over sodium sulfate, and, after filtration, concentrated in vacuo.

[0104] By column chromatographic purification of the crude product obtained on silica gel with an n-heptane / ethyl acetate gradient, cyclopropylmethyl (2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}phenoxy)acetate (201 mg, 64% of theory) was obtained in the form of a colorless oil. 1 H NMR (CDCI3δ, ppm): 7.49 (d, 1H), 7.20 (m, 2H), 7.04 (dt, 1H), 6.88 (dd, 1H), 6.80 (d, 1H), ), 6.26

[0105] (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).

[0106] In analogy to the preparation examples given above and recited at the appropriate point, and taking into account the general information on the preparation of substituted N-heterocyclyl- and N-heteroaryltetrahydropyrimidinones, the following compounds are obtained: Table I.1: Preferred compounds of formula (I.1) are compounds I.1-1 to I.1-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.1-1 to I.1-25 of Table I.1 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q in Table 1. Table 1: Table I.2: Preferred compounds of formula (I.2) are compounds I.2-1 to I.2-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.2-1 to I.2-25 of Table I.2 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.3: Preferred compounds of formula (I.3) are compounds I.3-1 to I.3-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.3-1 to I.3-25 of Table I.3 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.4: Preferred compounds of formula (I.4) are the compounds I.4-1 to I.4-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.4-1 to I.4-25 of Table I.4 are thus characterized by the meaning of the respective entries No. 1 to 25 for Q of the

[0107] Table 1 defined.

[0108] Table I.5: Preferred compounds of formula (I.5) are compounds I.5-1 to I.5-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.5-1 to I.5-25 of Table I.5 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1.

[0109] Table I.6: Preferred compounds of formula (I.6) are compounds I.6-1 to I.6-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.6-1 to I.6-25 of Table I.6 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1.

[0110] Table I.7: Preferred compounds of formula (I.7) are compounds I.7-1 to I.7-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.7-1 to I.7-25 of Table I.7 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1.

[0111] Table I.8: Preferred compounds of formula (I.8) are compounds I.8-1 to I.8-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.8-1 to I.8-25 of Table I.8 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1.

[0112] Table I.9: Preferred compounds of the formula (I.9) are the compounds I.9-1 to I.9-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.9-1 to I.9-25 of Table I.9 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1.

[0113] Table I.10: Preferred compounds of formula (I.10) are compounds I.10-1 to I.10-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.10-1 to I.10-25 of Table I.10 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1.

[0114] Table I.11: Preferred compounds of formula (I.11) are compounds I.11-1 to I.11-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.11-1 to I.11-25 of Table I.11 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1. Table I.12: Preferred compounds of formula (I.12) are compounds I.12-1 to I.12-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.12-1 to I.12-25 of Table I.12 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.13: Preferred compounds of formula (I.13) are compounds I.13-1 to I.13-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.13-1 to I.13-25 of Table I.13 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.14: Preferred compounds of formula (I.14) are compounds I.14-1 to I.14-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.14-1 to I.14-25 of Table I.14 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.15: Preferred compounds of formula (I.15) are compounds I.15-1 to I.15-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.15-1 to I.15-25 of Table I.15 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.16: Preferred compounds of formula (I.16) are compounds I.16-1 to I.16-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.16-1 to I.16-25 of Table I.16 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.17: Preferred compounds of formula (I.17) are compounds I.17-1 to I.17-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.17-1 to I.17-25 of Table I.17 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.18: Preferred compounds of formula (I.18) are compounds I.18-1 to I.18-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.18-1 to I.18-25 of Table I.18 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table 1.19: Preferred compounds of formula (1.19) are compounds 1.19-1 to 1.19-25, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.19-1 to 1.19-25 of Table 1.19 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1.

[0115] Table 1.20: Preferred compounds of formula (1.20) are compounds 1.20-1 to 1.20-25, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.20-1 to 1.20-25 of Table 1.20 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1.

[0116] Table 1.21: Preferred compounds of formula (1.21) are compounds 1.21-1 to 1.21-25, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.21-1 to 1.21-25 of Table 1.21 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1.

[0117] Table 1.22: Preferred compounds of formula (1.22) are compounds 1.22-1 to 1.22-25, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.22-1 to 1.22-25 of Table 1.22 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1. Table I.23: Preferred compounds of formula (I.23) are compounds I.23-1 to I.23-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.23-1 to I.23-25 ​​of Table I.23 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.24: Preferred compounds of formula (I.24) are compounds I.24-1 to I.24-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.24-1 to I.24-25 of Table I.24 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.25: Preferred compounds of formula (I.25) are the compounds I.25-1 to I.25-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.25-1 to I.25-25 of Table I.25 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table 1.26: Preferred compounds of formula (1.26) are compounds 1.26-1 to 1.26-25, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.26-1 to 1.22-25 of Table 1.26 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1.

[0118] Table 1.27: Preferred compounds of formula (1.27) are compounds 1.27-1 to 1.27-25, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.27-1 to 1.27-25 of Table 1.27 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1.

[0119] Table 1.28: Preferred compounds of formula (1.28) are compounds 1.28-1 to 1.28-25, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.28-1 to 1.28-25 of Table 1.28 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1.

[0120] Table 1.29: Preferred compounds of formula (1.29) are compounds 1.29-1 to 1.29-25, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.29-1 to 1.29-25 of Table 1.29 are thus defined by the meaning of the respective entries Nos. 1 to 25 for Q of Table 1. Table I.30: Preferred compounds of formula (I.30) are compounds I.30-1 to I.30-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.30-1 to I.30-25 of Table I.30 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.31: Preferred compounds of formula (I.31) are compounds I.31-1 to I.31-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.31-1 to I.31-25 of Table I.31 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.32: Preferred compounds of formula (I.32) are compounds I.32-1 to I.32-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.32-1 to I.32-25 of Table I.32 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. Table I.33: Preferred compounds of formula (I.33) are the compounds I.33-1 to I.33-25, wherein Q has the meanings given in the respective row of Table 1. The compounds I.33-1 to I.33-25 of Table I.33 are thus defined by the meaning of the respective entries No. 1 to 25 for Q of Table 1. NMR data of selected examples: The 1 H-NMR data for selected examples of compounds of general formula (I) are presented in two different ways: (a) classical NMR analysis and interpretation or (b) in the form of 1H-NMR peak lists according to the method described below. a) Classical NMR interpretation, Examples I.7-12: 1 H NMR (CDCl3 δ, 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). b) NMR peak list method The1 H-NMR data of selected examples are presented in the form of 1 H-NMR peak lists are recorded. For each signal peak, the δ value in ppm is listed first, followed by the signal intensity in parentheses. The δ value – signal intensity number pairs of different signal peaks are listed separated by semicolons. The peak list of an example therefore has the form: δ1(Intensity1 ) ; δ2(Intensity2);……..; δ i (Intensity i ) ;……; δ n (Intensity n ) The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown. For calibration of the chemical shift of 1For H NMR spectra, we use tetramethylsilane and / or the solvent chemical shift, especially for spectra measured in DMSO. Therefore, the tetramethylsilane peak may or may not appear in NMR peak lists.

[0121] The lists of IH NMR peaks are similar to the classical 1 H-NMR printouts and thus usually contain all peaks that are listed in a classical NMR interpretation.

[0122] In addition, they can be used like classic 1 H-NMR printouts show solvent signals, signals of stereoisomers of the target compounds which are also the subject of the invention, and / or peaks of impurities.

[0123] When specifying compound signals in the delta range of solvents and / or water, our lists of 1H-NMR peaks show the common solvent peaks, for example, peaks of DMSO in DMSO-D6 and the peak of water, which usually have high intensity on average.

[0124] The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example, with a purity of >90%).

[0125] Such stereoisomers and / or impurities may be typical for the respective manufacturing process. Their peaks can thus help identify the reproduction of our manufacturing process based on "byproduct fingerprints."

[0126] An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also empirically evaluated expected values) can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation would be similar to the peak picking in classical 1 H-NMR interpretation.

[0127] Further details on 1 H-NMR peak lists can be found in the Research Disclosure Database Number 564025.

[0128] The present invention furthermore relates to the use of one or more compounds of the general formula (I) according to the invention and / or salts thereof, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (I.1) to (I.33) and / or salts thereof, each as defined above, as herbicide and / or plant growth regulator, preferably in crops of useful and / or ornamental plants.

[0129] The present invention further relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) according to the invention and / or salts thereof, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulae (1.1) to (1.33) and / or salts thereof, in each case as defined above, or of an agent according to the invention, as defined below, is applied to the (harmful) plants, (harmful) plant seeds, the soil in or on which the (harmful) plants grow, or the area under cultivation.

[0130] The present invention also relates to a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or salts thereof, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulae (1.1) to (1.33) and / or salts thereof, in each case as defined above, or of an agent according to the invention, as defined below, is applied to unwanted plants (e.g. harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed of the unwanted plants (i.e. plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in or on which the unwanted plants grow (e.g. the soil of cultivated land or non-cultivated land) or the cultivated area (i.e.area where the unwanted plants will grow).

[0131] The present invention furthermore also relates to methods for controlling the growth of plants, preferably of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or salts thereof, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1) to (1.33) and / or salts thereof, in each case as defined above, or of an agent according to the invention, as defined below, is applied to the plant, the seed of the plant (ie plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in or on which the plants grow (e.g. the soil of cultivated land or non-cultivated land) or the area under cultivation (ie area on which the plants will grow).

[0132] The compounds of general formula (I) according to the invention or the compositions according to the invention can be applied, for example, by pre-sowing (optionally also by incorporation into the soil), pre-emergence, and / or post-emergence methods. Some representatives of the monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds according to the invention are mentioned as examples, without implying a restriction to specific species.

[0133] Preferably, in a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the general formula (I) and / or salts thereof are used for controlling harmful plants or for regulating the growth in crops of useful plants or ornamental plants, wherein the useful plants or ornamental plants are transgenic plants in a preferred embodiment.

[0134] The compounds of general formula (I) according to the invention and / or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous weeds:

[0135] Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0136] Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0137] If the compounds of general formula (I) according to the invention are applied to the soil surface before the germination of the harmful plants (grass and / or weeds) (pre-emergence method), the emergence of the weed seedlings is either completely prevented or they grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.

[0138] When the compounds of general formula (I) according to the invention are applied to the green parts of the plant by post-emergence, growth stops after the treatment and the weeds remain in the growth stage present at the time of application or die completely after a certain time, so that in this way weed competition harmful to the crop plants is eliminated very early and sustainably.

[0139] Although the compounds of the general formula (I) according to the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Uactuca, Einum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, are only insignificantly damaged or not damaged at all, depending on the structure of the respective compound according to the invention and the application rate thereof. For these reasons, the present compounds are very suitable for the selective control of unwanted plant growth in plant crops such as agricultural crops or ornamental plantings.

[0140] Furthermore, the compounds of general formula (I) according to the invention (depending on their respective structure and the applied rate) exhibit outstanding growth-regulating properties in crop plants. They regulate the plant's own metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, for example, by inducing desiccation and stunting. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, since, for example, lodging can be reduced or completely prevented.

[0141] Due to their herbicidal and plant growth-regulating properties, the compounds of general formula (I) according to the invention can also be used to combat weeds in crops of plants modified by genetic engineering or conventional mutagenesis. The transgenic plants are generally characterized by particularly advantageous properties, for example, resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria, or viruses. Other special properties relate, for example, to the harvested product in terms of quantity, quality, storability, composition, and specific constituents. Thus, transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvested product, are known.

[0142] With regard to transgenic crops, preference is given to using the compounds of the general formula (I) according to the invention and / or their salts in economically important transgenic crops of useful and ornamental plants, e.g. cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.

[0143] Preferably, the compounds of general formula (I) according to the invention can also be used as herbicides in crops of useful plants which are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.

[0144] Due to their herbicidal and plant growth-regulating properties, the compounds of general formula (I) according to the invention can also be used to control weeds in crops of known or yet-to-be-developed genetically modified plants. The transgenic plants are generally characterized by particularly advantageous properties, for example, resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria, or viruses. Other special properties relate, for example, to the harvested product in terms of quantity, quality, storability, composition, and specific constituents. Thus, transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvested product, are known.Other special properties may include tolerance or resistance to abiotic stressors such as heat, cold, drought, salt and ultraviolet radiation.

[0145] The compounds of general formula (I) according to the invention or their salts are preferably used in economically important transgenic crops of crops and ornamental plants, e.g., cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava, and maize, or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas, and other vegetables. The compounds of general formula (I) can preferably be used as herbicides in crops that are resistant to the phytotoxic effects of the herbicides or have been genetically engineered to be resistant.

[0146] Conventional methods for producing new plants with modified traits compared to existing plants include classical breeding methods and the creation of mutants. Alternatively, new plants with modified traits can be created using genetic engineering techniques.

[0147] Numerous molecular biological techniques for producing new transgenic plants with modified traits are known to those skilled in the art. For such genetic manipulations, nucleic acid molecules can be introduced into plasmids, allowing mutagenesis or sequence modification through recombination of DNA sequences. Using standard methods, base substitutions can be performed, partial sequences can be removed, or natural or synthetic sequences can be added. Adapters or linkers can be attached to the DNA fragments to connect them to one another.

[0148] The production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme that specifically cleaves transcripts of the above-mentioned gene product.

[0149] For this purpose, DNA molecules can be used that contain the entire coding sequence of a gene product, including any flanking sequences present, or DNA molecules that contain only parts of the coding sequence. These parts must be long enough to produce an antisense effect in the cells. It is also possible to use DNA sequences that exhibit a high degree of homology to the coding sequences of a gene product, but are not completely identical.

[0150] When nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any compartment of the plant cell. However, to achieve localization in a specific compartment, the coding region can, for example, be linked to DNA sequences that ensure localization in a specific compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). Expression of the nucleic acid molecules can also take place in the organelles of the plant cells. The transgenic plant cells can be regenerated into whole plants using known techniques. In principle, the transgenic plants can be plants of any plant species, i.e., both monocotyledonous and dicotyledonous plants.

[0151] Transgenic plants are available that exhibit altered properties through overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

[0152] Preferably, the compounds of the general formula (I) according to the invention can be used in transgenic crops which are resistant to growth promoters, such as dicamba, or to herbicides which inhibit essential plant enzymes, e.g. acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoyl lisoxazoles and analogous active substances.

[0153] When the compounds of the general formula (I) according to the invention are used in transgenic crops, in addition to the effects on weeds observed in other crops, effects often occur which are specific for the application in the respective transgenic crop, for example a modified or specifically expanded weed spectrum which can be controlled, modified application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influence on the growth and yield of the transgenic crops.

[0154] The invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or salts thereof as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crops.

[0155] The preferred use is in cereals, preferably maize, wheat, barley, rye, oats, millet or rice, in pre- or post-emergence.

[0156] It is also preferred for use in soybeans in pre- or post-emergence.

[0157] The use according to the invention for controlling weeds or for regulating plant growth also includes the case in which a compound of general formula (I) or a salt thereof is formed from a precursor substance ("prodrug") only after application to the plant, in the plant, or in the soil. The invention also relates to the use of one or more compounds of general formula (I) or salts thereof or of an agent according to the invention (as defined below) (in a method) for controlling weeds or for regulating plant growth, characterized in that an effective amount of one or more compounds of general formula (I) or salts thereof is applied to the plants (weeds, optionally together with the useful plants), plant seeds, the soil in or on which the plants grow, or the cultivated area.

[0158] The invention also relates to a herbicidal and / or plant growth regulating agent, characterized in that the agent

[0159] (a) contains one or more compounds of the general formula (I) and / or salts thereof as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1) to (1.33) and / or salts thereof, each as defined above, and

[0160] (b) one or more further substances selected from groups (i) and / or (ii):

[0161] (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, other herbicides (ie those which do not correspond to the general formula (I) defined above), fungicides, safeners, fertilizers and / or other growth regulators,

[0162] (ii) one or more formulation aids commonly used in crop protection.

[0163] The further agrochemically active substances of component (i) of a composition according to the invention are preferably selected from the group of substances listed in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0164] A herbicidal or plant growth regulator according to the invention preferably comprises one, two, three, or more formulation auxiliaries (ii) customary in crop protection, selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, carriers that are solid at 25°C and 1013 mbar, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably organic solvents that are miscible with water in any ratio at 25°C and 1013 mbar. The compounds of the general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts, or granules in the customary preparations.The invention therefore also relates to herbicidal and plant growth-regulating compositions containing compounds of general formula (I) and / or salts thereof. The compounds of general formula (I) according to the invention and / or salts thereof can be formulated in various ways, depending on the biological and / or chemical-physical parameters specified.Possible formulation options include: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting agents (DP), seed dressings, granules for broadcast and soil application, granules (GR) in the form of micro-, spray-, lift- and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types and the formulation aids such as inert materials, surfactants, solvents and other additives are known to the person skilled in the art and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ, HvOlphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, NY; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, NY, 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood, NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY, 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart, 1976; Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag, Munich, 4th Ed., 1986. Wettable powders are preparations that are uniformly dispersible in water and contain, in addition to the active ingredient, a diluent or inert substance, ionic and / or non-ionic surfactants (wetting agents, dispersants), e.g.polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyltaurine. To produce the wettable powders, the herbicidal active ingredients are finely ground in conventional equipment such as hammer mills, fan mills, and air jet mills and mixed simultaneously or subsequently with the formulation auxiliaries. Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, xylene, or higher-boiling aromatics or hydrocarbons, or mixtures of the organic solvents, with the addition of one or more ionic and / or non-ionic surfactants (emulsifiers).Examples of emulsifiers that can be used are: alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.

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

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

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

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

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

[0170] For the production of disc, fluidized bed, extruder and spray granules see, for example, the procedures in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook", 5th ed., McGraw-Hill, New York 1973, pp. 8-57. For further details on the formulation of crop protection products see, for example, GC Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0171] The agrochemical preparations, preferably herbicidal or plant growth regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferably 2 to 80% by weight, of active ingredients of the general formula (I) and salts thereof.

[0172] In wettable powders, for example, the active ingredient concentration is about 10 to 90 wt.%, the remainder to 100 wt.% consists of conventional formulation components. In emulsifiable concentrates, the active ingredient concentration can be about 1 to 90, preferably 5 to 80 wt.% Dust-like formulations contain 1 to 30 wt.% active ingredient, preferably 5 to 20 wt.% active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt.% active ingredient. In water-dispersible granules, the active ingredient content depends partly on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used. In water-dispersible granules, the active ingredient content is, for example, between 1 and 95 wt.%, preferably between 10 and 80 wt.%.

[0173] In addition, the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, and solvents, fillers, carriers, and colorants, defoamers, evaporation inhibitors, and pH and viscosity adjusters. Examples of formulation aids are described, among others, in "Chemistry and Technology of Agrochemical Formulations," ed. DA Knowles, Kluwer Academic Publishers (1998).

[0174] The compounds of general formula (I) according to the invention or their salts can be used as such or in the form of their preparations (formulations) in combination with other pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and / or growth regulators, e.g., as a ready-to-use formulation or as tank mixes. The combination formulations can be prepared based on the above-mentioned formulations, taking into account the physical properties and stability of the active ingredients to be combined.

[0175] As combination partners for the compounds of general formula (I) according to the invention in mixture formulations or in tank mixes, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.

[0176] Of particular interest is the selective control of weeds in crops of useful and ornamental plants. Although the compounds of the general formula (I) according to the invention already exhibit very good to sufficient selectivity in many crops, phytotoxicity can in principle occur in some crops, and especially in the case of mixtures with other herbicides that are less selective. In this regard, combinations of compounds of the general formula (I) according to the invention that comprise the compounds (I) or their combinations with other herbicides or pesticides and safeners are of particular interest. The safeners, which are used in an antidote-effective concentration, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g.in economically important crops such as cereals (wheat, barley, rye, maize, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.

[0177] The weight ratios of herbicide (mixture) to safener generally depend on the application rate of herbicide and the efficacy of the respective safener and can vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. The safeners can be formulated analogously to the compounds of general formula (I) or mixtures thereof with other herbicides / pesticides and can be provided and applied as a ready-to-use formulation or tank mix with the herbicides.

[0178] For application, the herbicide or herbicide-safener formulations in commercial form are diluted in the usual way, e.g., with water in the case of wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Dust-like preparations, soil or broadcast granules, and sprayable solutions are not usually diluted with other inert substances before use.

[0179] External conditions such as temperature, humidity, etc. influence to a certain extent the application rate of the compounds of the general formula (I) according to the invention and / or their salts. The application rate can vary within wide limits. For use as a herbicide for controlling weeds, the total amount of compounds of the general formula (I) according to the invention and their salts is preferably in the range from 0.001 to 10.0 kg / ha, more preferably in the range from 0.005 to 5 kg / ha, more preferably in the range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence application.

[0180] When using compounds of the general formula (I) according to the invention and / or salts thereof as plant growth regulators, for example as stalk shorteners in crop plants as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or maize, the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / ha. This applies both to pre-emergence and post-emergence application.

[0181] Application as a stem shortener can be carried out at various stages of plant growth. For example, application after tillering, at the beginning of longitudinal growth, is preferred.

[0182] Alternatively, when used as a plant growth regulator, seed treatment is also an option, which includes various seed dressing and coating techniques. The application rate depends on the individual technique and can be determined in preliminary trials.

[0183] As combination partners for the compounds of general formula (I) in mixture formulations or in tank mixes, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase or which act as plant growth regulators can be used, as described, for example, in 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 literature cited therein.

[0184] Known herbicides or plant growth regulators that can be combined with compounds of the general formula (I) include, for example, the following active ingredients (the compounds are designated either by the "common name" according to the International Organization for Standardization (ISO) or by the chemical name or by the code number) and always include all application forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. One and sometimes several application forms are mentioned as examples: Acetochlor, Acifluorfen, Acifluorfen-methyl, Acifluorfen-sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazon, Amidochlor, Amidosulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, Aminocyclopyrachlor, Aminocyclopyrachlor-potassium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid-dimethylammonium, Aminopyralid-tripromine, Amitrol, Ammonium sulfamates,Anilofos, Asulam, Asulam-Kalium, Asulam-Natrium, Atrazin, Azafenidin, Azimsulfuron, Beflubutamid, (S)-(-)- Beflubutamid, Beflubutamid-M, Benazolin, Benazolin-ethyl, Benazolin-dimethylammonium, Benazolin-Klaium, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Bensulid, Bentazon, Bentazon-Natrium, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-Natium, Bipyrazone, Bispyribac, Bispyribac-Natium, Bixlozon, Bromacil, Bromacil-lithium, Bromacil-Natrium, Bromobutid, Bromofenoxim, Bromoxynil, Bromoxynilbutyrat, Bromoxynil-Kalium, Bromoxynil- heptanoat und Bromoxynil-octanoat, Busoxinon, Butachlor, Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylat, Cafenstrol, Cambendichlor, Carbetamide, Carfentrazon, Carfentrazon- Ethyl, Chloramben, Chloramben-ammonium, Chloramben-diolamin, Chlroamben-methyl, Chlorambenmethylammonium, Chlor amben-Natium, Chlorbromuron, Chlorfenac, Chlorfenac-ammonium, Chlorfenac-Natium, Chlorfenprop, Chlorfenprop-methyl,Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chlorophthalim, Chlorotoluron, Chlorsulfuron, Chlorthal, Chlorthal-dimethyl, Chlorthal-monomethyl, Cinidon, Cinidon-ethyl, Cinmethylin, exo-(+)- Cinmethylin, d.h. (lR,2S,4S)-4-isopropyl-l-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptan, exo-(-)-Cinmethylin, d.h. (lR,2S,4S)-4-isopropyl-l-methyl-2-[(2-methylbenzyl)oxy]-7- oxabicyclo[2.2.1]heptan, Cinosulfuron, Clacyfos, Clethodim, Clodinafop, Clodinafop-ethyl, Clodinafop- propargyl, Clomazon, Clomeprop, Clopyralid, Clopyralid-methyl, Clopyralid-olamin, Clopyralid- Kalium, Clopyralid-tripomin, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cycloat, Cyclopyranil, Cyclopyrimorat, Cyclosulfamuron, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Cyprazin, 2,4-D (sowie die Ammonium, Butotyl, Butyl, Cholin, Diethylammonium, Dimethylammonium, Diolamin, Doboxyl, Dodecylammonium, Etexyl, Ethyl, 2-Ethylhexyl, Heptylammonium, Isobutyl, Isooctyl,Isopropyl, Isopropylammonium, Lithium, Meptyl, Methyl, Kalium, Tetradecylammonium, Triethylammonium, Triisopropanolammonium, Tripromin and Trolamin Salze davon), 2,4-DB, 2,4-DB-butyl, 2,4-DB-Dimethylammonium, 2,4-DB-isooctyl, 2,4-DB-Kalium und 2,4-DB-Natrium, Daimuron (Dymron), Dalapon, Dalapon-Calcium, Dalapon-Magnesium, Dalapon- Natium, Dazomet, Dazomet-Natrium, n-Decanol, 7-Deoxy-D-sedoheptulose, Desmedipham, Detosyl- pyrazolat (DTP), Dicamba und seine Salze (z.B. Dicamba-biproamin, Dicamba-N,N-Bis(3- aminopropyl)methylamin, Dicamba-butotyl, Dicamba-cholin, Dicamba-Diglycolamin, Dicamba- Dimethylammonium, Dicamba-Diethanolaminemmonium, Dicamba-Diethylammonium, Dicamba- isopropylammonium, Dicamba-methyl, Dicamba-monoethanolamin, Dicamba-olamin, Dicamba- Kalium, Dicamba-Natium, Dicamba-Triethanolamin), Dichlobenil, 2-(2,4-Dichlorbenzyl)-4,4-dimethyl- l,2-oxazolidin-3-on, 2-(2,5-Dichlorbenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, Dichlorprop, Dichlorprop-butotyl,Dichlorprop-Dimethylammonium, Dichhlorprop-etexyl, Dichlorpropethylammonium, Dichlorprop-isoctyl, Dichlorprop-methyl, Dichlorprop-Kalium, Dichlorprop-Natrium, Dichlorprop-P, Dichlorprop-P-Dimethylammonium, Dichlorprop-P-etexyl, Dichlorprop-P-Kalium, Dichlorprop-Natrium, Diclofop, Diclofop-methyl, Diclofop-P, Diclofop-P-methyl, Diclosulam, Difenzoquat, Difenzoquat-metilsulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr-Natrium, Dimefuron, Dimepiperate, Dimesulfazet, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimetrasulfuron, Dinitramine, Dinoterb, Dinoterb-Acetate, Diphenamid, Diquat, Diquat-Dibromid, Diquat-Dichloride, Dithiopyr, Diuron, DNOC, DNOC-Ammonium, DNOC-Kalium, DNOC-Natrium, Endothal, Endothal-Diammonium, Endothal-Dikalium, Endothal-Dinatrium, Epyrifenacil (S-3100), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethametsulfuron-Methyl, Ethiozin, Ethofumesate, Ethoxyfen, Ethoxyfen-Ethyl, Ethoxysulfuron, Etobenzanid, F-5231,d.h. N-[2- Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-lH-tetrazol-l-yl]-phenyl]-ethansulfonamid, F- 7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-lH-benzimidazol-4-yl]-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion, Fenoxaprop, Fenoxaprop-P, Fenoxaprop-Ethyl, Fenoxaprop-P-Ethyl, Fenoxasulfone, Fenpyrazone, Fenquinotrione, Fentrazamid, Flamprop, Flamprop- Isoproyl, 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-Natrium, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenpyr, Flufenpyr-Ethyl, Flumetsulam, Flumiclorac, Flumiclorac-Pentyl, Flumioxazin, Fluometuron, Flurenol, Flurenol-Butyl, -Dimethylammonium und -Methyl, Fluoroglycofen, Fluoroglycofen-Ethyl, Flupropanat, Flupropanat-Natrium, Flupyrsulfuron, Flupyrsulfuron-Methyl, Flupyrsulfuron-Methyl- Natrium, Fluridon, Flurochloridon,Fluroxypyr, Fluroxypyr-Butometyl, Fluroxypyr-Meptyl, Flurtamon, Fluthiacet, Fluthiacet-Methyl, Fomesafen, Fomesafen-Natrium, Foramsulfuron, Foramsulfuron-Natrium, Fosamine, Fosamine-Ammonium, Glufosinat, Glufosinat-Ammonium, Glufosinat-Natrium, L- Glufosinat-Ammonium, L-Glufosinat-Natrium, Glufosinat-P-Natrium, Glufosinat-P-Ammonium, Glyphosat, Glyphosat-Ammonium, Glyphosat-Isopropylammonium, Glyphosat-Diammonium, Glyphosat-Dimethylammonium, Glyphosat-Kalium, Glyphosat-Natrium, Glyphosat-Sesquinatrium und Glyphosat-Trimesium, H-9201, d.h. O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl- isopropylphosphoramidothioat, Halauxifen, Halauxifen-methyl, Halosafen, Halosulfuron, Halosulfuron- Methyl, Haloxyfop, Haloxyfop-P, Haloxyfop-Ethoxyethyl, Haloxyfop-P-Ethoxyethyl, Haloxyfop- Methyl, Haloxyfop-P-Methyl, Haloxif op-Natrium, Hexazinon, HNPC-A8169, i.e. Prop-2-yn-l-yl (2S)- 2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propanoat, HW-02, d.h. l-(Dimethoxyphosphoryl)-ethyl- (2,4-dichlorphenoxy)acetat,Hydantocidin, Icafolin, Icafolin-Methyl, Imazamethabenz, Imazamethabenz-Methyl, Imazamox, Imazamox-Ammonium, Imazapic, Imazapic-Ammonium, Imazapyr, Imazapyr-Isopropylammonium, Imazaquin, Imazaquin-Ammonium, Imazaquin-Methyl, Imazethapyr, Imazethapyr-Ammonium, Imazosulfuron, Indanofan, Indaziflam, Indolauxipyr, lodosulfuron, lodosulfuron-Methyl, lodosulfuron-Methyl-Natrium, Ioxynil, loxynil-Lithium, -Octanoat, -Kalium und Natrium, Ipfencarbazon, Iptriazopyrid, i.e. 3-[(Isopropylsulfonyl)methyl]-N-(5-methyl- l,3,4-oxadiazol-2-yl)-5-(trifluormethyl)[l,2,4]triazolo-[4,3-a]pyridin-8-carboxamid, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Karbutilat, KUH-043, d.h. 3-({[5-(Difluormethyl)-l-methyl-3- (trifluormethyl)-lH-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-l,2-oxazol, Ketospiradox, Ketospiradox-Kalium, Lactofen, Lenacil, Linuron, MCPA, MCPA-Butotyl, -Butyl, -Dimethylammonium, -Diolamin, -2-Ethylhexyl, -Ethyl, -Isobutyl, Isoctyl, -Isopropyl, -Isopropylammonium, - Methyl,Olamin, -Kalium, -Natrium und -Trolamin, MCPB, MCPB-Methyl, -Ethyl und -Natrium, Mecoprop, Mecoprop-Butotyl, Mecoprop- dimethylammonium, Mecoprop-Diolamin, Mecoprop-Etexyl, Mecoprop-Ethadyl, Mecoprop-Isoctyl, Mecoprop-Methyl, Mecoprop-Kalium, Mecoprop-Natrium, und Mecoprop-Trolamin, Mecoprop-P, Mecoprop-P-Butotyl, -Dimethylammonium, -2-Ethylhexyl und - Kalium, Mefenacet, Mefluidid, Mefluidid-Diolamin, Mefluidid-Kalium, Mesosulfuron, Mesosulfuron- Methyl, Mesosulfuron-Natrium, Mesotrion, Methabenzthiazuron, Metam, Metamifop, Metamitron, Metazachlor, Metazosulfuron, Methabenzthiazuron, Methiopyrsulfuron, Methiozolin, Methyl isothiocyanat, Metobromuron, Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metproxybicyclon, Metribuzin, Metsulfuron, Metsulfuron-Methyl, Molinat, Monolinuron, Monosulfuron, Monosulfuron- Methyl, MT-5950, d.h. N-[3-Chlor-4-(l-methylethyl)-phenyl]-2-methylpentanamid, NGGC-011, Napropamid, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-l-methyl-5-benzyloxypyrazol, Neburon,Nicosulfuron, Nonansäure (Pelargonsäure), Norflurazon, Ölsäure (Fettsäuren), Orbencarb, Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Paraquat-dichlorid, Paraquat-Dimethylsulfat, Pebulat, Pendimethalin, Penoxsulam, Pentachlorphenol, Pentoxazon, Pethoxamid, Petroleumöl, Phenmedipham, Phenmedipham-Ethyl, Picloram, Picloram-dimethylammonium, Picloram-Etexyl, Picloram-Isoctyl, Picloram-Methyl, Picloram-Olamin, Picloram-Kalium, Picloram-Triethylammonium, Picloram-Tripromin, Picloram- Trolamin, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron, Primisulfuron-Methyl, Prodiamine, Profoxydim, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone-Natrium, Propyrisulfuron, Propyzamid, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen-Ethyl, Pyraquinat, Pyrasulfotol, Pyrazolynat (Pyrazolat), Pyrazosulfuron, Pyrazosulfuron-Ethyl, Pyrazoxyfen,Pyribambenz, Pyribambenz-Isopropyl, Pyribambenz-Propyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridat, Pyriftalid, Pyriminobac, Pyriminobac -Methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac-Natrium, Pyroxasulfon, Pyroxsulam, Quinclorac, Quinclorac-Dimethylammonium, Quinclorac-Methyl, Quinmerac, Quinoclamin, Quizalofop, Quizalofop-Ethyl, Quizalofop-P, Quizalofop-P-Ethyl, Quizalofop-P-Tefuryl, QYM201 , i.e. 1 - { 2-Chlor-3- [(3-cyclopropyl-5-hydroxy- 1 -methyl- 1 H-pyrazol-4-yl)carbonyl] -6- (trifluormethyl)phe-nyl}piperidin-2-on, Rimsulfuron, Saflufenacil, Sethoxydim, Siduron, Simazine, Simetryn, SL-261, Sulcotrione, Sulfentrazone, Sulfometuron, Sulfometuron-Methyl, Sulfosulfuron, , SYP-249, d.h. l-Ethoxy-3-methyl-l-oxobut-3-en-2-yl-5-[2-chlor-4-(trifluormethyl)phenoxy]-2- nitrobenzoat, SYP-300, i.e. l-[7-Fluor-3-oxo-4-(prop-2-in-l-yl)-3,4-dihydro-2H-l,4-benzoxazin-6-yl]- 3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (Trichloressigsäure) und seine Salze, z.B. TCA-ammonium,TCA-Calcium, TCA-Ethyl, TCA-Magnesium, TCA-Natrium, Tebuthiuron, Tefuryltrione, Tembotrion, Tepraloxydim, Terbacil, Terbucarb, Terbumeton, Terbuthylazine, Terbutryn, Tetflupyrolimet, Thaxtomin, Thenylchlor, Thiazopyr, Thiencarbazone, Thiencarbazon-Methyl, Thifensulfuron, Thifensulfuron-Methyl, Thiobencarb, Tiafenacil, Tolpyralat, Topramezon, Tralkoxydim, Triafamon, Tri-allat, Triasulfuron, Triaziflam, Tribenuron, Tribenuron-Methyl, Triclopyr, Triclopyr-Butotyl, Triclopyr-Cholin, Triclopyr-Ethyl, Triclopyr-Triethylammonium, Trietazine, Trifloxysulfuron, Trifloxysulfuron-Natrium, Trifludimoxazin, Trifluralin, Triflusulfuron, Triflusulfuron- Methyl, Tritosulfuron, Harnstoffsulfat, Vernolat, XDE-848, ZJ-0862, d.h. 3,4-Dichlor-N-{2-[(4,6- dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, 3-(2-Chlor-4-fluor-5-(3-methyl-2,6-dioxo-4- trifluormethyl-3,6-dihydropyrimidin-l(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazol-5- carbonsäuremethylester, 3-(2-Chlor-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6- dihydropyrimidin-l(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazol-5-carbonsäureethylester, 3-(2-Chlor-,

[0185] 4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydropyrimidin-l(2H)-yl)phenyl)-5-methyl-4,5- dihydroisoxazol-5-carbonsäure, Ethyl-[(3-{2-chlor-4-fhror-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)- 3,6-dihydropyrimidin- 1 (2H)-yl]phenoxy}pyridin-2-yl)oxy] acetat, 3-Chlor-2-[3- (difluormethyl)isoxazolyl-5-yl]phenyl-5-chlorpyrimidin-2-ylether, 2-(3,4-Dimethoxyphenyl)-4-[(2- hydroxy-6-oxocyclohex- 1 -en- 1 -yl)carbonyl] -6-mcthyl py l idazi n-3(2H)-on, 2-({2-[(2- Methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-l,3-dion, (5-Hydroxy-l-methyl- lH-pyrazol-4-yl)(3,3,4-trimethyl- 1 , 1 -dioxido-2, 3 -dihydro- 1 -benzothiophen-5-yl)methanon, 1 -Methyl-4- [(3,3,4-trimethyl- 1 , 1 -dioxido-2, 3 -dihydro- 1 -benzothiophen-5-yl)carbonyl]- lH-pyrazol-5-yl propan- 1 - sulfonat, 4- { 2-Chlor-3-[(3,5-dimethyl- IH-pyrazol- 1 -yl)methyl] -4-(methylsulfonyl)benzoyl} - 1 -methyl- lH-pyrazol-5-yl-l,3-dimethyl-lH-pyrazol-4-carboxylat; Cyanomethyl-4-amino-3-chlor-5-fluor-6-(7- fluor-lH-indol-6-yl)pyridin-2-carboxylat, Prop-2-yn-l-yl 4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol- 6-yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2- carboxylat, Benzyl-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Ethyl-4- amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor- 6-(7 -fluor- 1 -isobutyryl- 1 H-indol-6-yl)pyridin-2-carboxylat, Methyl 6-( 1 -acetyl-7 -fluor- 1 H-indol-6-yl)- 4-amino-3-chlor-5-fluorpyridin-2-carboxylat, Methyl-4-amino-3-chlor-6-[l-(2,2-dimethylpropanoyl)-7- fluor-lH-indol-6-yl]-5-fluorpyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-[7-fluor-l- (methoxyacetyl)-lH-indol-6-yl]pyridin-2-carboxylat, Kalium 4-amino-3-chlor-5-fluor-6-(7-fluor-lH- indol-6-yl)pyridin-2-carboxylat, Natrium-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2- carboxylat,Butyl-4-amino-3-chlor-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridin-2-carboxylat, 4-Hydroxy- l-methyl-3-[4-(tifluoromethyl)pyridin-2-yl]imidazolidin-2-on, 3-(5-tert-butyl-l,2-oxazol-3-yl)-4- hydroxy-l-methylimidazolidin-2-on, 3-[5-Chlor-4-(trifluormethyl)pyridin-2-yl]-4-hydroxy-l- methylimidazolidin-2-on, 4-Hydroxy-l-methoxy-5-methyl-3-[4-(trifluormethyl)pyridin-2- yl]imidazolidin-2-on, 6-[(2-Hydroxy-6-oxocyclohex-l-en-l-yl)carbonyl]-l,5-dimethyl-3-(2- methylphenyl)chinazolin-2,4(lH,3H)-dion, 3-(2,6-Dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-l-en- l-yl)carbonyl]-l-methylchinazolin-2,4(lH,3H)-dion, 2-[2-chlor-4-(methylsulfonyl)-3-(morpholin-4- ylmethyl)benzoyl] -3-hydroxycyclohex-2-en- 1 -on, 1 -(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin- 1 - iumsalz (mit passenden Anionen wie z.B Chlorid, Acetat oder Trifluoracetat), l-(2-Carboxyethyl)-4- (pyridazin-3-yl)pyridazin-l-iumsalz (mit passenden Anionen wie z.B. Chlorid, Acetat oder Trifluoracetat),4-(Pyrimidin-2-yl)-l-(2-sulfoethyl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(Pyridazin-3-yl)-l-(2-sulfoethyl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-Carboxyethyl)-4-(l,3-thiazol-2-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-Carboxyethyl)-4-(l,3,4-thiadiazol-2-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), Methyl (2R)-2-{[(E)-({2-chloro-4-fluoro-5-[3- methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(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-l(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, methyl (2R / S)-2-{[(E)-({2-chloro-4-fhror-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6- dihydropyrimidin-l(2H)-yl]phenyl}methylidene)amino]oxy}propanoate,(E)-2- (Trifluormethyl)benzaldehyd-O-{2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoyl}oxim, 2-Fluor-N- (5-methyl-l,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluormethyl)benzamid, (2R)-2-[(4-Amino- 3,5-dichlor-6-fluor-2-pyridyl)oxy]propancarbonsäure, 2-Ethoxy-2-oxoethyl-l-{2-chlor-4-fluor-5-[3- methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}cyclopropancarboxylat, 2- Methoxy-2-oxoethyl-l-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin- 1 (2H)-yl]phenoxy Jcyclopropancarboxylat, { [(1 - { 2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}essigsäure, 2-(2- Brom-4-chlorbenzyl)-4,4-dimethyl-l,2-oxazolidin-3-on, Methyl 3-{2-chlor-4-fluor-5-[3-methyl-2,6- dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin- 1 (2H)-yl]phenyl} -3a,4,5,6-tetrahydro-6aH- cyclopenta[d][l,2]oxazol-6a-carboxylat, Ethyl 3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluoromethyl)-3,6-dihydropyrimidin- 1 (2H)-yl]phenyl} -3a,4,5,6-tetrahydro-6aH- cyclopentafd] [1 ,2]oxazol-6a-carboxylat,

[0186] Examples of plant growth regulators as possible mixing partners are: Abscisic acid and related analogues [e.g. (2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoic acid, methyl-(2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(l-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-l-yl)penta-2,4-dienoic acid, (2E,4E)-5-(l-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-dienoate, methyl (2E,4E)-5-(l-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-dienoate, (2Z,4E)-5-(2-hydroxy-l,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-carboxylic acid amide, substituted 1-aminocyclopropyl-1-carboxylic acid derivatives as described in DE3335514, EP30287, DE2906507 or US5123951, 1-aminocyclopropyl-1-hydroxamic acid, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl, L-canalin, catechin and catechins (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 chain characteristic of LCOs. COs, sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units, but have side chains that distinguish them from chitin molecules [(CSHBNOS)^ CAS NO. 1398-61-4] and chitosan molecules [(C5HnNO4)n, CAS No. 9012-76-4]),Chitin-like compounds, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-l-enyl)propionic acid, l-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, l-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozide, dazomet, dazomet sodium, n-decanol, dikegulac, dikegulac sodium, endothal, endothal-di-potassium, -di-sodium, and mono(N,N-dimethylalkylammonium), ethephon, l-ethylcyclopropene, flumetralin, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfid, indole-3-acetic acid (IAA), 4-Indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid esters or other derivatives (e.g. jasmonic acid methyl ester, jasmonic acid ethyl ester), lipochitooligosaccharides (LCO, in some cases also called symbiotic nodulation signals (Nod or Nod factors) or Myc factors, consist of an oligosaccharide backbone of ß-l,4-linked / V-Acctyl-D-glucosamine residues (“GlcNAc”) with an N-linked fatty acid side chain fused to the non-reducing end. As can be seen from the structure, LCOs differ in the number of GlcNAc units in the backbone structure, in the length and degree of saturation of the fatty acid chain as well as in the substitution of the reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, l-(4-methylphenyl)-N-(2-oxo-l-propyl-l,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[l,2-b]furan-2-one and related lactones as described in EP2248421, 2-(l-naphthyl)acetamide,1-Naphthylacetic acid, 2-Naphthyloxyacetic acid, nitrophenolate mixture, 4-Oxo-4[(2-phenylethyl)amino]butyric acid, Paclobutrazol, 4-Phenylbutyric acid and its salts (e.g. sodium 4-phenylbutanoate, potassium 4-phenylbutanoate), Phenylalanine, N-Phenylphthalamic acid, Prohexadione, Prohexadione calcium, 1-n-Propylcyclopropene, Putrescine, Prohydrojasmone, Rhizobitoxin, Salicylic acid and salicyclic acid methyl ester, Sarcosine, Sodium cycloprop-l-en-l-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, Spermine, Strigolactone, Tecnazene, Thidiazuron, Triacontanol, Trinexapac, Trinexapac-ethyl, Tryptophan, Tsitodef, Uniconazole, Uniconazole-P, 2-Fluoro-N-(3-methoxyphenyl)-9H - purine-6-amine, 2-Chloro-N-(3-methoxyphenyl)-9H-purine-6-amine.,

[0187] The following safeners, for example, are also suitable as combination partners for the compounds of the general formula (I) according to the invention: S1) Compounds of the formula (S1), where the symbols and indices have the following meanings: n A is a natural number from 0 to 5, preferably 0 to 3;

[0188] RA 1 is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl;

[0189] W A is an unsubstituted or substituted divalent heterocyclic radical from the group of saturated or aromatic five-membered ring heterocycles having 1 to 3 hetero ring atoms from the group N and O, wherein at least one N atom and at most one O atom is contained in the ring, preferably a radical from the group (W A 1 ) to (W A 5 ), m A is 0 or 1 ; RA 2 is ORA 3 , SRA 3 or NRA 3 RA4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is bonded via the N atom to the carbonyl group in (S1) and is unsubstituted or substituted by radicals from the group (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenyl, preferably a radical of the formula OR A 3 , NHRA 4 or N(CH3)2, in particular of the formula ORA 3 ; RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C 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 9Hydrogen, (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 identical or different and are hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C12)-cycloalkyl or substituted or unsubstituted phenyl; RA 10 is H, (C3-C12)-cycloalkyl, substituted or unsubstituted phenyl or substituted or unsubstituted heteroaryl; preferably: a) compounds of the dichlorophenylpyrazolin-3-carboxylic acid type (S1 a ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazole-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazole-3-carboxylic acid ethyl ester (S1-1) ("Mefenpyr-diethyl"), and related compounds as described in WO-A-91 / 07874; b) derivatives of dichlorophenylpyrazolecarboxylic acid (S1 b), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methyl-pyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropyl-pyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethyl-ethyl)pyrazole-3-carboxylate (S1-4) and related compounds as 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 as described, for example, in EP-A-268554; d) compounds of the triazolecarboxylic acid type (S1 d), preferably compounds such as fenchlorazole (ethyl ester), ie l-(2,4-dichlorophenyl)-5-trichloromethyl-(lH)-l,2,4-triazole-3-carboxylic acid ethyl ester (S 1-7), and related compounds as described in EP-A-174 562 and EP-A-346 620; e) compounds of the type 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 e ), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S 1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S 1-9) and related compounds as described in WO-A-91 / 08202, or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S 1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S 1-11) ("isoxadifen-ethyl") or -n-propyl ester (S 1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S 1-13) as described in patent application WO-A-95 / 07897. f) Compounds of the triazolyloxyacetic acid derivative type (S1f ), preferably compounds such as methyl-{[l,5-bis(4-chloro-2-fluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (S1-14) or {[1,5-bis(4-chloro-2-fluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (S1-15) or methyl-{[5-(4-chloro-2-fluorophenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (S1-16) or {[5-(4-chloro-2-fluorophenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (S 1 - 17) or methyl-{[1 -(4- chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (S 1 - 18) or {[l-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (S 1-19), as described in patent application W02021105101

[0190] S2) quinoline derivatives of the formula (S2), where the symbols and indices have the following meanings:

[0191] R B 1 is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl; n Bis a natural number from 0 to 5, preferably 0 to 3;

[0192] R B 2 is OR B 3 , SR B 3 or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is bonded via the N atom to the carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenyl, preferably a radical of the formula ORB 3 , NHRB 4 or N(CH3), in particular of the formula OR B 3 ;

[0193] RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 C atoms;

[0194] RB 4is hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy or substituted or unsubstituted phenyl;

[0195] TB is a (C1 or C2)-alkanediyl chain that is unsubstituted or with one or two

[0196] (C1-C4) alkyl radicals or with [(C1-C3) alkoxy] carbonyl; preferably: a) compounds of the 8-quinolinoxyacetic acid type (S2 a), preferably (5-chloro-8-quinolinoxy)acetic acid (l-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy)acetic acid (l,3-dimethyl-but-l-yl) ester (S2-2), (5-chloro-8-quinolinoxy)acetic acid 4-allyloxy-butyl ester (S2-3), (5-chloro-8-quinolinoxy)acetic acid l-allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinolinoxy)acetic acid ethyl ester (S2-5), (5-chloro-8-quinolinoxy)acetic acid methyl ester (S2-6), (5-chloro-8-quinolinoxy)acetic acid allyl ester (S2-7), (5-chloro-8-quinolinoxy)acetic acid 2-(2-propylidene- iminoxy)-l-ethyl ester (S2-8), (5-chloro-8-quinolinoxy)acetate 2-oxo-prop-l-yl ester (S2-9) and related compounds as described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366, and (5-chloro-8-quinolinoxy)acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium,or phosphonium salts as described in WO-A-2002 / 34048; b) compounds of the type (5-chloro-8-quinolinoxy)malonic acid (S2, b ), preferably compounds such as (5-chloro-8-quinolinoxy)malonic acid diethyl ester, (5-chloro-8-quinolinoxy)malonic acid diallyl ester, (5-chloro-8-quinolinoxy)malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198. S3) Compounds of formula (S3) where the symbols and indices have the following meanings:

[0197] R c 1 is (C1-C4)alkyl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C3-C7)cycloalkyl, preferably dichloromethyl;

[0198] R c 2 , R c 3are the same or different hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)alkynyl, (C1-C4)haloalkyl, (C2-C4)haloalkenyl, (C1-C4)alkylcarbamoyl-(C1-C4)alkyl, (C2-C4)alkenyl- carbamoyl-(C1-C4)alkyl, (C1-C4)alkoxy-(C1-C4)alkyl, dioxolanyl-(C1-C4)alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R c 2 and R c 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; preferably: active ingredients of the dichloroacetamide type, which are frequently used as pre-emergence safeners (soil-active safeners), such as

[0199] “Dichlormid” (N,N-diallyl-2,2-dichloroacetamide) (S3-1), “R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), “R-28725” (3-dichloroacetyl-2,2,-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(l,3-dioxolan-2-yl)-methyl]-dichloroacetamide) from PPG Industries (S3-5), "DKA-24" (N-allyl-N- [(allylaminocarbonyl)methyl]-dichloroacetamide) from Sagro-Chem (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-l-oxa-3-aza-spiro[4,5]decane) from Nitrokemia or Monsanto (S3-7), "TI-35" (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), "Diclonon" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9) ((RS)-l-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[l,2-a]pyrimidin-6-one) from BASF, "Furilazol" or "MON 13900" ((RS)-3-Dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10); and its (R)-isomer (S3-11).S4) N- Acylsulfonamide der Formel (S4) und ihre Salze,. worin die Symbole und Indizes folgende Bedeutungen haben:

[0200] XD ist CH oder N;

[0201] R D 1 ist CO-NR D 5 RD 6 oder NHCO-RD 7 ;

[0202] R D 2 ist Halogen, (C1-C4)-Haloalkyl, (C1-C4)-Haloalkoxy, Nitro, (C1-C4)-Alkyl, (C1-C4)-Alkoxy, (C1- C4)-Alkylsulfonyl, (C1-C4)-Alkoxycarbonyl oder (C1-C4)-Alkylcarbonyl;

[0203] R D 3 ist Wasserstoff, (C1-C4)-Alkyl, (C2-C4) -Alkenyl oder (C2-C4)-Alkinyl;

[0204] R D 4 ist Halogen, Nitro, (C1-C4)-Alkyl, (C1-C4)-Haloalkyl, (C1-C4)-Haloalkoxy, (C3-C6)-Cycloalkyl, Phenyl, (C1-C4)-Alkoxy, Cyano, (C1-C4)-Alkylthio, (C1-C4)-Alkylsulfinyl, (C1-C4)- Alkylsulfonyl, (C1-C4)-Alkoxycarbonyl oder (C1-C4)-Alkylcarbonyl;

[0205] R D 5is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing VD heteroatoms from the group nitrogen, oxygen and sulfur, where the last seven radicals are substituted by VD substituents from the group 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 also (C1-C4-alkyl and (C1-C4)-haloalkyl are substituted;

[0206] R D 6 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, where the last three radicals are substituted by VD radicals from the group halogen, hydroxy, (C1-C4)-alkyl, (C1-C4)-alkoxy and (C1-C4)-alkylthio, or

[0207] R D 5 and R D 6together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;

[0208] R D 7 is hydrogen, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, where the last two radicals are substituted by VD substituents from the group halogen, (C1-C4)-alkyl and (C1-C4)-haloalkyl; n D is 0, 1 or 2; m D is 1 or 2; v D is 0, 1, 2 or 3; of these, preference is given to compounds of the N-acylsulfonamide type, e.g. of the following formula (S4 a ), which are known, for example, from WO-A-97 / 45016 where R D 7 (C1-C6)-alkyl, (C3-C6)-cycloalkyl, where the last two radicals are substituted by vD substituents from the group halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio and, in the case of cyclic radicals, also (C1-C4)-alkyl and (C1-C4)-haloalkyl; R D 4Halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3; m D 1 or 2; v D is 0, 1, 2 or 3; and acylsulfamoylbenzoic acid amides, e.g. of the following formula (S4 b ), which are known for example from WO-A-99 / 16744, e.g. those where R D 5 = Cyclopropyl and (R D 4 ) = 2-OMe is ("Cyprosulfamide", S4-1), RD 5 = Cyclopropyl and (R D 4 ) = 5-C1-2-OMe is (S4-2), RD 5 = Ethyl and ( R D 4 ) = 2-OMe is (S4-3), R D 5 = Isopropyl and (R D 4 ) = 2-OMe (S4-5). as well as compounds of the N-acylsulfamoylphenylurea type of the formula (S4 c ), which are known for example from EP-A-365484, where R D 8 and R D 9 independently of one another hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, R D 4Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, CF3m D1 or 2; for example 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea. S5) Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001. S6) Active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g. 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005 / 112630.S7) Compounds of formula (S7) as described in WO-A-1998 / 38856. where the symbols and indices have the following meanings:

[0209] RE 1 , RE 2 are independently halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, nitro;

[0210] AE is COOR E 3 or COSR E 4

[0211] 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 3are independently 0, 1 or 2, preferably diphenylmethoxyacetic acid, diphenylmethoxyacetate ethyl ester, diphenylmethoxyacetate methyl ester (CAS Reg. No. 41858-19-9) (S7-1). S8) Compounds of formula (S8) as described in WO-A-98 / 27049 wherein

[0212] X F CH or N, n F in case X F =N is an integer from 0 to 4 and RF 1 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 hydrogen or (C1-C4)-alkyl, RF 3hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof, preferably compounds wherein X F CH, n F an integer from 0 to 2, R F 1 Halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, R F 2 hydrogen or (C1-C4)-alkyl, R F 3Hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy, or salts thereof. S9) Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), e.g. 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), as described in WO-A-1999 / 000020. S10) Compounds of the formulas (S10 a ) or (S10 b ) as described in WO-A-2007 / 023719 and WO-A-2007 / 023764 where R G 1 Halogen, (C1-C4)-Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3Y G , Z G independently O or S, n G an integer from 0 to 4, R G2 (C1-C 16 )-Alkyl, (C2-C6)-Alkenyl, (C3-C6)-Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, R G 3hydrogen or (C1-C6)-alkyl. S11) Active ingredients of the oxyimino compound type (S11), which are known as seed dressings, such as E.g., "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), known as a seed dressing safener for millet against metolachlor damage, "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2), known as a seed dressing safener for millet against metolachlor damage, and "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), known as a seed dressing safener for millet against metolachlor damage. S12) Active ingredients from the class of isothiochromanones (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998 / 13361.S13) One or more compounds from group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed dressing safener for maize against damage from thiocarbamate herbicides, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as a safener for pretilachlor in sown rice, "Flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), known as a seed dressing safener for millet against damage from alachlor and metolachlor, "CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-l-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage from imidazolinones, "MG 191" (CAS Reg. No. 96420-72-3) (2-Dichloromethyl-2-methyl-l,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn, "MG-838" (CAS Reg. No. 133993-74-5) (2-propenyl l-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia, "Disulfoton" (O,O-diethyl S-2-ethylthioethyl phosphorus dithioate) (S13-7), "Dietholate" (O,O-diethyl-O-phenylphosphorothioate) (S13-8), "Mephenate" (4-chlorophenyl methyl carbamate) (S13-9).

[0213] S14) Active substances which, in addition to a herbicidal effect against weeds, also have a safener effect on crops such as rice, such as

[0214] "Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethyl-piperidine-l-carbothioate), known as a safener for rice against damage from the herbicide Molinate, "Daimuron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), known as a safener for rice against damage from the herbicide Imazosulfuron, "Cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-l-(l-methyl-l-phenylethyl)urea, see JP-A-60087254), known as a safener for rice against damage from some herbicides, "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), known as a safener for rice against damage from some herbicides, "CSB" (l-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage from some herbicides in rice.

[0215] S15) Compounds of formula (S15) or their tautomers as described in WO-A-2008 / 131861 and WO-A-2008 / 131860 wherein

[0216] R H1 a (C1-C6)-haloalkyl radical and

[0217] R H 2 hydrogen or halogen and R H 3 , H 4 independently of each other hydrogen, (C1-C 16 )-alkyl, (C2-C 16 )-alkenyl or (C2-C 16)-Alkynyl, where each of the last three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (Ci-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)cycloalkenyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, wherein each of the latter 4 radicals is unsubstituted or substituted by one or more radicals from the group 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, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, is substituted, or,

[0218] R H 3 (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy means and

[0219] R H 4 hydrogen or (C1-C4)-alkyl, or

[0220] R H 3 and R H 4together with the directly bonded N atom forms a four- to eight-membered heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (Ci-C4-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio.

[0221] S16) Active ingredients that are primarily used as herbicides but also have a safener effect on crops, 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), l-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloroethyl). Biological examples:

[0222] A. Herbicidal activity and crop compatibility of selected compounds of general formula (I) in post-emergence

[0223] Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants were sown in plastic or wood fiber pots in sandy loam soil, covered with soil, and grown in a greenhouse under controlled growth conditions. Two to three weeks after sowing, the test plants were treated at the single-leaf stage. The compounds of the invention, formulated as wettable powders (WP) or emulsion concentrates (EC), were then sprayed onto the green plant parts as an aqueous suspension or emulsion with the addition of 0.5% additive at a water application rate equivalent to 600 l / ha. After the test plants had been in the greenhouse for approximately three weeks under optimal growth conditions, the effect of the preparations was visually assessed in comparison to untreated controls. For example, 100% effect means plants have died, 0% effect means the same as the control plants.

[0224] The following Tables A1 to A13 show the effects of selected compounds of general formula (I) according to Tables 1.1 to 1.33 on various weeds and at an application rate corresponding to 20 g / ha and lower, obtained according to the test procedure mentioned above.

[0225] The appendices “a”, “b” and “c” differentiate according to the dosages used for otherwise identically tested weeds.

[0226] Table A1a: Post-emergence effect at 1.25g / ha against ABUTH in % Table A1b: Post-emergence effect at 5g / ha against ABUTH in % Table A1c: Post-emergence effect at 20g / ha against ABUTH in %

[0227] Table A2a: Post-emergence effect at 1.25g / ha against ALOMY in % Table A2b: Post-emergence effect at 5g / ha against ALOMY in % Table A2c: Post-emergence effect at 20g / ha against ALOMY in % Table A3b: Post-emergence effect at 5g / ha against AMARE in %

[0228] Table A3c: Post-emergence effect at 20g / ha against AMARE in % Table A4a: Post-emergence efficacy at 1.25g / ha against ECHCG in % Table A4b: Post-emergence effect at 5g / ha against ECHCG in % Table A4c: Post-emergence effect at 20g / ha against ECHCG in % Table A5a: Post-emergence effect at 20g / ha against LOLRI in % Table A6b: Post-emergence effect at 5g / ha against MATIN in % Table A6c: Post-emergence effect at 20g / ha against MATIN in % Table A7a: Post-emergence effect at 1.25g / ha against PHBPU in %

[0229] Table A7b: Post-emergence effect at 5g / ha against PHBPU in % Table A7c: Post-emergence effect at 20g / ha against PHBPU in %

[0230] Table 8a: Post-emergence effect at 1.25g / ha against POLCO in % Table A8b: Post-emergence effect at 5g / ha against POLCO in %

[0231] Table A9a: Post-emergence effect at 1.25g / ha against SETVI in % Table A9b: Post-emergence effect at 5g / ha against SETVI in % Table A9c: Post-emergence effect at 20g / ha against SETVI in % Table A10a: Post-emergence effect at 1.25g / ha against VERPE in % Table A10b: Post-emergence effect at 5g / ha against VERPE in % Table A10c: Post-emergence effect at 20g / ha against VERPE in % Table A11a: Post-emergence effect at 1.25g / ha against VIOTR in %

[0232] Table A11b: Post-emergence effect at 5g / ha against VIOTR in % Table A11c: Post-emergence effect at 20g / ha against VIOTR in %

[0233] Table A12a: Post-emergence effect at 1.25g / ha against DIGSA in % Table A12b: Post-emergence effect at 5g / ha against DIGSA in %

[0234] Table A12c: Post-emergence effect at 20g / ha against DIGSA in % Table A13a: Post-emergence effect at 1.25g / ha against KCHSC in % Table A13b: Post-emergence effect at 5g / ha against KCHSC in % Table A13c: Post-emergence effect at 20g / ha against KCHSC in % Tables A14 to A17 below show the crop tolerances of selected compounds of general formula (I) according to Tables I.1 to I.33 at an application rate corresponding to 20 g / ha or lower, as observed in trials conducted according to the aforementioned test procedure. The observed effects on selected crops are given in comparison to the untreated controls (values ​​in %). The appendices "a", "b", and "c" differentiate according to the dosages used on otherwise identically tested crops. Table A14a: Post-emergence effect at 1.25 g / ha against ZEAMX in % Table A14b: Post-emergence effect at 5g / ha against ZEAMX in % Table A15a: Post-emergence effect at 1.25g / ha against TRZAS in %

[0235] Table A15b: Post-emergence effect at 20g / ha against TRZAS in % Table A16a: Post-emergence effect at 1.25g / ha against ORYSA in %

[0236] Table A16c: Post-emergence effect at 20g / ha against ORYSA in % Table A17a: Post-emergence effect at 1.25g / ha against GLXMA in % As these results show, compounds of the general formula (I) according to the invention have good herbicidal activity against harmful plants such as, for example, e.g. B. Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Bassia scoparia (KCHSC), Lolium rigidum (LOLRI), Tripleurospermum inodorum (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Veronica persica (VERPE) and Viola tricolor (VIOTR) at an application rate of 0.02 kg active ingredient or less per hectare, and (b) good crop tolerance in organisms such as Oryza sativa (ORYSA), Zea mays (ZEAMX), Glycine max (GLXMA) and Triticum aestivum (TRZAS) at an application rate of 0.02 kg and less per hectare. B. Comparative herbicidal activity and crop plant tolerance of exemplary compounds according to the 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") postemergence. Tables B1-B5 below show the effects of compounds according to the invention (I.7-12, I.7-14, I.7-16), obtained according to the aforementioned test procedure, on various weeds at an application rate corresponding to 20 g / ha and lower, in comparison with structurally similar compounds known from the literature ("a-27", "a-29", disclosed in WO2002 / 098227).

[0237] The tested compounds according to the invention (1.7-12, 1.7-14, 1.7-16) differ from the known compounds in the literature by variance of a significant structural feature with respect to the ester unit while maintaining the “cycloalkyl group” by incorporating a methylene bridge (-CH2-).

[0238] Table Bl

[0239] Table B2

[0240] Table B3 Table B4

[0241] Table B5 As the results presented in Tables B1 to B5 show, the compounds 1.7-12, 1.7-14, 1.7-16 according to the invention have a significantly improved herbicidal activity against weeds such as Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Avena fatura (AVEFA) and Veronica persica (VERPE) at an application rate of 20 g and lower per hectare, compared to the structurally similar compounds known from the literature “a-27”, “a-29”, (WO2002 / 098227), or a structure generically encompassed therein. In the following tables B6 to BIO, the effects of compounds according to the invention (1.7-12, 1.7-14, 1.7-16), which were obtained according to the above-mentioned test procedure, on the crop plants Oryza sativa (ORYSA), Ze a mays (ZEAMX) and Triticum aestivum (TRZAS) at an application rate corresponding to 5 g / ha and lower are shown in comparison to structurally similar compounds known from the literature ("a-27", "a-29", disclosed in W02002 / 098227).

[0242] Table B6

[0243] Table B7

[0244] Table B8

[0245] Table B9

[0246] Table BIO

[0247] As the results presented in Tables B6 to BIO show, compounds according to the invention (1.7-12, 1.7-14, 1.7-16) in direct comparison with structurally similar compounds known from the literature "a-27", "a-29", (W02002 / 098227), or a structure generically encompassed therein, show significantly improved tolerance with regard to the crop plants Oryza sativa (ORYSA), Zea mays (ZEAMX) and Triticum aestivum (TRZAS) at an application rate of 5 g and lower per hectare.

Claims

Claims:

1. Substituted N-phenyluracils of the general formula (I) or their salts where R 1 represents hydrogen, halogen, cyano, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C8)alkoxy or (C1-C8)haloalkoxy, R 2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C1-C8)-alkoxy, R 3 represents hydrogen, halogen or (C1-C8)-alkoxy, R 4 represents halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C8)-haloalkyl or (C2-C8)-alkynyl, R 5 , R 6 and R 7 independently of one another represent hydrogen, halogen, cyano, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-alkoxy or (C1-C8)-haloalkoxy, G represents unbranched or branched (C1-C8)-alkylene, Q represents a radical of the formula, R 8 represents hydrogen, (C1-C8)-alkyl or cyano, R 9 represents hydrogen or (C1-C8)-alkyl, R 10represents (C3-C8)-cycloalkyl which is unsubstituted or each independently of one another by “m” radicals 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 represents spiro-(C5-C9)-alkanyl or dispiro-(C7-C8)-alkanyl, which are unsubstituted or each independently substituted by "m" radicals 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).

2. Compounds of the general formula (I) according to claim 1 and / or a salt thereof, characterized in that R 1 represents hydrogen, halogen, cyano, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy or (C1-C6)haloalkoxy, R 2represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C1-C6)-alkoxy, R 3 represents hydrogen, halogen or (C1-C6)-alkoxy, R 4 represents halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C6)-haloalkyl or (C2-C6)-alkynyl, R 5 , R 6 and R 7 independently of one another represent hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy or (C1-C6)-haloalkoxy, G represents unbranched or branched (C1-C6)-alkylene, Q represents a radical of the formula, R 8 represents hydrogen, (C1-C6)-alkyl or cyano, R 9 represents hydrogen or (C1-C6)-alkyl, R 10represents (C3-C7)-cycloalkyl, which is unsubstituted or each independently substituted by "m" radicals 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 represents spiro-(C5-C7)-alkanyl or dispiro-(C7-C8)-alkanyl, which are unsubstituted or each independently substituted by "m" radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, m represents 0, 1, 2 or 3 and X and Y independently represent O (oxygen) or S (sulfur) 3. Compounds of the general formula (I) according to claim 1 and / or a salt thereof, characterized in that R 1für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, Prop-1-yl, 1-Methyl- ethyl, 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-Di- methylbutyl, 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, Trifluormethyl, Difluormethyl, Pentafluorethyl, 2,2-Difluor- ethyl, 2,2,2-Trifluorethyl, Methoxy, Ethoxy, Prop-1-yloxy, Prop-2-yloxy, But-1-yloxy, But-2-yloxy, 2-Methylprop-1-yloxy, 1,1-Dimethyleth-1-yloxy, Difluormethoxy, Trifluormethoxy, Pentafluorethoxy, 2,2-Difluorethoxy, 2,2,2-Trifluorethoxy steht, R 2für Wasserstoff, Fluor, Chlor, Brom, Trifluormethyl, Methoxy, Ethoxy, Prop-1-yloxy, But-1-yloxy steht, R 3 für Wasserstoff, Fluor, Chlor, Brom, Methoxy, Ethoxy, Prop-1-yloxy, Prop-2-yloxy, But-1-yloxy, But-2-yloxy, 2-Methylprop-1-yloxy, 1,1-Dimethyleth-1-yloxy steht, R 4 für Fluor, Chlor, Brom, Cyano, NO2, C(O)NH2, C(S)NH2, Trifluormethyl, Difluormethyl, Pentafluorethyl, Ethinyl, Propin- 1-yl, 1 -Butin- 1-yl, Pentin- 1-yl, Hexin-l-yl steht, R 5 , R 6 und R 7 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, 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-Di-methylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3.3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1 , 1 ,2-Trimethylpropyl, 1,2,2-Tri- methylpropyl, 1 -Ethyl- 1 -methylpropyl, l-Ethyl-2-methylpropyl, Trifluormethyl, Difluormethyl, Pentafluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Methoxy, Ethoxy, Prop-l-yloxy, Prop-2-yloxy, But-l-yloxy, But-2-yloxy, 2-Methylprop-l-yloxy, 1.1-Dimethyleth-l-yloxy, Difluormethoxy, Trifluormethoxy, Pentafluorethoxy, 2.2-Difluorethoxy, 2,2,2-Trifluorethoxy stehen, G für Methylen, (Methyl)methylen, (Ethyl)methylen, (Prop-l-yl)methylen, (Prop-2- yl)methylen, (But-l-yl)methylen, (But-2-yl)methylen, (Pent-l-yl)methylen, (Pent-2- yl)methylen, (Pent-3-yl)methylen, (Dimethyl)methylen, (Diethyl)methylen, Ethylen, n- Propylen, (l-Methyl)ethyl-l-en, (2-Methyl)ethyl-l-en, n-Butylen, 1 -Methylpropyl- 1 -en, 2-Methylpropyl- 1 -en, 3-Methylpropyl-l-en, 1,1 -Dimethylethyl- 1 -en, 2,2-Dimethylethyl- 1-en, 1 -Ethylethyl- 1 -en, 2-Ethylethyl-l-en, l-(Prop-l-yl)ethyl-l-en, 2-(Prop-l-yl)ethyl- 1-en, l-(Prop-2-yl)ethyl-l-en, 2-(Prop-2-yl)ethyl-l-en, 1,1,2-Trimethylethyl-l-en, 1.2.2-Trimethylethyl-l-en, 1,1,2,2-Tetramethylethyl-l-en, n-Pentylen, 1 -Methylbutyl- 1- en, 2-Methylbutyl- 1 -en, 3-Methylbutyl- 1 -en, 4-Methylbutyl-l-en, 1,1-Dimethylpropyl- 1-en, 2,2-Dimethylpropyl- 1 -en, 3,3-Dimethylpropyl-l-en, 1,2-Dimethylpropyl-l-en, 1.3-Dimethylpropyl-l-en, 1 -Ethylpropyl- 1 -en, n-Hexylen, 1 -Methylpentyl- 1 -en, 2-Methylpentyl- 1 -en, 3-Methylpentyl- 1 -en, 4-Methylpentyl- 1 -en, 1,1 -Dimethylbutyl- 1- en, 1,2-Dimethylbutyl-l-en, 1,3-Di-methylbutyl-l-en, 2,2-Dimethylbutyl- 1 -en, 2.3-Dimethylbutyl- 1 -en, 3,3-Dimethylbutyl-l-en, 1 -Ethylbutyl- 1 -en, 2-Ethylbutyl- 1 -en, 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 independently represent O (oxygen) or S (sulfur) and Q represents one of the following specifically named groups Q1 to Q-25, where in the structural formulas of the following table the arrow represents a bond of the respective group Q to the carbonyl group in the general formula (I): Compounds of general formula (I) according to claim 1 and / or their salt, characterized in that R 1 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, R 2 represents hydrogen, fluorine or chlorine, R 3represents hydrogen, fluorine, chlorine, bromine or methoxy, R 4 represents fluorine, chlorine, bromine, cyano, NO2, C(O)NH2, C(S)NH2, trifluoromethyl, ethynyl or propyn-1-yl, R 5 , R 6 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, G for methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (l-methyl)ethyl-l-ene, (2-methyl)ethyl-l-ene, n-butylene, 1-methylpropyl-l-ene, 2-methylpropyl-l-ene, 3-methylpropyl-l-ene, 1,1-dimethylethyl-l-ene, 2,2-dimethylethyl-l-ene, 1-ethylethyl-l-ene, 2-ethylethyl-l-ene, l-(prop-l-yl)ethyl-l-ene, 2-(prop-l-yl)ethyl-l-ene, l-(prop-2-yl)ethyl-l-ene, 2-(prop-2-yl)ethyl-l-ene, n-pentylene, 1-methylbutyl-l-ene, or n-hexylene stands, X and Y independently represent O (oxygen) or S (sulfur) and Q represents one of the groups Q1 to Q-25 specifically mentioned in claim 3. Compounds of the general formula (I) according to claim 1 and / or their salt, characterized in that R 1represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, R 2 represents fluorine, R 3 represents fluorine, R 4 represents chlorine, bromine, cyano, NO2, C(O)NH2 or C(S)NH2, R 5 , R 6 and R 7 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, G represents 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 independently of one another represent O (oxygen) or S (sulfur), and Q represents one of the groups Q-1 to Q-25 specifically mentioned in claim 3.

6. Compounds of the general formula (I) according to claim 1 and / or a salt thereof, characterized in that R 1represents hydrogen, fluorine, chlorine or bromine, R 2 represents fluorine, R 3 represents fluorine, R 4 represents chlorine, bromine, cyano or NO2, R 5 represents hydrogen, fluorine, chlorine or bromine, R 6 represents hydrogen, fluorine, chlorine, bromine or cyano, R 7 represents hydrogen, fluorine, chlorine or bromine, G represents methylene, (methyl)methylene or (ethyl)methylene, X and Y independently represent O (oxygen) or S (sulfur) and Q represents one of the groups Q-1 to Q-25 specifically mentioned in claim 3. Compounds of the general formula (I) according to claim 1 and / or their salt, characterized in that R 1 stands for hydrogen, R 2 stands for fluorine, R 3 stands for fluorine, R 4 represents chlorine, bromine, cyano or NO2, R 5 stands for hydrogen, R 6stands for hydrogen, fluorine, chlorine, R 7 stands for hydrogen, G stands for methylene, (methyl)methylene, X stands for O (oxygen) or S (sulfur), Y stands for O (oxygen) and Q represents one of the groups Q-1 to Q-25 specifically mentioned in claim 3. Compounds of the general formula (I) according to claim 1 and / or their salt, characterized in that R 1 stands for hydrogen,# R 2 stands for fluorine, R 3 represents fluorine, R 4 represents chlorine, bromine or cyano, R 5 stands for hydrogen, R 6 represents hydrogen or fluorine, R 7stands for hydrogen, G stands for methylene, X stands for O (oxygen), Y stands for O (oxygen) and Q stands for one of the groups 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 mentioned in claim 3.

9. Use of one or more compounds of the general formula (I) as defined in any one of claims 1 to 8 and / or salts thereof as a herbicide and / or plant growth regulator, preferably in crops of useful and / or ornamental plants. 10.Herbicidal and / or plant growth regulating agent, characterized in that the agent contains one or more compounds of the general formula (I) as defined in any one of claims 1 to 8 and / or salts thereof, and further one or more substances selected from groups (i) and / or (ii), with (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides, fungicides, safeners, fertilizers and / or further growth regulators, (ii) one or more formulation auxiliaries customary in plant protection. Method for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) as described in one of the Claims 1 to 8 and / or salts thereof, or - an agent according to claim 10 is applied to the plants, plant seeds, the soil in or on which the plants grow, or the cultivation area.

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