EP4602036A1 - Substituted n-phenyluracils and salts thereof, and use thereof as herbicidal active substances - Google Patents

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

Substituted N-phenyluracils and their salts and their use as herbicidal active ingredients Description The invention relates to the technical field of plant protection agents, in particular that of herbicides for the selective control of weeds and grass weeds in crops of useful plants. In particular, 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 of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. Plant protection products known to date for the selective control of harmful plants in crops or active substances for controlling undesirable plant growth sometimes have disadvantages when used, either because they (a) have no or insufficient herbicidal effect against certain harmful plants, (b) have too small a spectrum of harmful plants that can be controlled with an active substance, (c) have too little selectivity in crops and/or (d) have a toxicologically unfavourable profile. Furthermore, some active substances that can be used as plant growth regulators in some crops lead to undesirably reduced crop yields in other crops or are not compatible with the crop or are only compatible within a narrow application rate range. Some of the known active substances cannot be produced economically on an industrial scale due to difficult-to-access precursors and reagents or have insufficient chemical stability. With other active substances, the effect depends too strongly on environmental conditions, such as weather and soil conditions. The herbicidal activity of these known compounds, especially at low application rates, and their tolerance to crop plants still require improvement. It is known from various documents 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, WO2002/098227, WO2002/098228, WO2003/028462, WO2003/028463, WO2003/0284647, WO2016/095768 and WO2022/043205). However, the known aryluracils have a number of gaps in their effectiveness, particularly against monocotyledonous weeds. A number of herbicidal active ingredient combinations based on N-linked aryluracils have also become known (cf. DE4437197, EP714602, WO96/07323, WO96/08151, JP11189506, JP2003/104808, JP2003/104809, JP2003/104810, JP2003/160415 and JP2003/160416). However, the properties of these active ingredient combinations were not satisfactory in all respects. Also known are substituted uracils which contain an N-linked and further substituted diaryl ether group or a corresponding heteroarylaryl ether residue (cf. US6333296, US6121201, WO2001/85907, EP1122244, EP1397958, EP1422227, WO 2002/098227). Furthermore, highly substituted N-phenyluracils with a specifically substituted carbonylalkyloxy group are described (cf. WO2011/137088). WO2018/019842 describes the use of specifically substituted N-phenyluracils for controlling certain dicotyledonous weeds which have specific resistances 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 well suited 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. wherein R ¹ is hydrogen, halogen, cyano, (C ₁ -C ₈ )-alkyl, (C ₁ -C ₈ )-haloalkyl, (C ₁ -C ₈ )-alkoxy or (C ₁ -C ₈ )-haloalkoxy, R ² is hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C ₁ -C ₈ )-alkoxy, R ³ is hydrogen, halogen or (C ₁ -C ₈ )-alkoxy, R ⁴ is halogen, cyano, NO ₂ , C(O)NH ₂ , C(S)NH ₂ , (C ₁ -C ₈ )-haloalkyl or (C ₂ -C ₈ )-alkynyl, R ⁵ , R ⁶ and R ⁷ independently of one another represent hydrogen, halogen, cyano, (C ₁ -C ₈ )-alkyl, (C ₁ -C ₈ )-haloalkyl, (C ₁ -C ₈ )-alkoxy or (C ₁ -C ₈ )-haloalkoxy, G represents unbranched or branched (C ₁ -C ₈ )-alkylene, Q represents a radical of the formula R ⁸ represents hydrogen, (C ₁ -C ₈ )-alkyl or cyano, R ⁹ represents hydrogen or (C ₁ -C ₈ )-alkyl, R ¹⁰ represents (C ₃ -C ₈ )-cycloalkyl which is unsubstituted or in each case independently substituted by “m” radicals selected from the group consisting of halogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy, cyano and nitro, or represents spiro-(C ₅ -C ₉ )-alkanyl or dispiro-(C ₇ -C ₈ )-alkanyl which is unsubstituted or in each case independently substituted by “m” radicals selected from the group consisting of halogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy and cyano, m is 0, 1, 2 or 3 and X and Y independently of one another are O (oxygen) or S (sulfur). Particularly preferred subject matter of the invention are compounds of the general formula (I) in which R ¹ is hydrogen, halogen, cyano, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )-alkoxy or (C ₁ -C ₆ )-haloalkoxy, R ² is hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C ₁ -C ₆ )-alkoxy, R ³ is hydrogen, halogen or (C ₁ -C ₆ )-alkoxy, R ⁴ represents halogen, cyano, NO ₂ , C(O)NH ₂ , C(S)NH ₂ , (C ₁ -C ₆ )-haloalkyl or (C ₂ -C ₆ )-alkynyl, R ⁵ , R ⁶ and R ⁷ independently represent hydrogen, halogen, cyano, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )-alkoxy or (C ₁ -C ₆ )-haloalkoxy, G represents unbranched or branched (C ₁ -C ₆ )-alkylene, Q represents a radical of the formula, R ⁸ represents hydrogen, (C ₁ -C ₆ )-alkyl or cyano, R ⁹ represents hydrogen or (C ₁ -C ₆ )-alkyl, R ¹⁰ represents (C ₃ -C ₇ )-cycloalkyl, which is unsubstituted or each independently substituted by "m" radicals selected from the group consisting of halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy, cyano, nitro or spiro-(C ₅ -C ₇ )-alkanyl or dispiro-(C ₇ -C ₈ )-alkanyl, which are unsubstituted or each independently substituted by "m" radicals selected from the group consisting of halogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )-alkoxy, m is 0, 1, 2 or 3 and X and Y are each independently O (oxygen) or S (sulfur). A particularly preferred subject of the invention are compounds of the general formula (I) in which R ¹ represents 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, 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, Trifluoromethyl, Difluoromethyl, Pentafluoroethyl,

2.2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-l-yloxy, prop-2-yloxy, but-1- yloxy, but-2-yloxy, 2-methylprop-l-yloxy, 1,1-dimethyleth-l-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,

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

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,

R ⁴ represents fluorine, chlorine, bromine, cyano, NO ₂ , C(O)NH ₂ , C(S)NH ₂ , trifluoromethyl, difluoromethyl, pentafluoroethyl, ethynyl, propyn- 1-yl, 1-butyn- 1-yl, pentyn- 1-yl, hexyn-l-yl,

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,

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, Trifluoromethyl, Difluoro- methyl, Pentafluoroethyl, 2,2-Difluoroethyl, 2,2,2-Trifluoroethyl, Methoxy, Ethoxy, Prop-l-yloxy, Prop-2-yloxy, But-l-yloxy, But-2-yloxy, 2-Methylprop-l-yloxy, 1,1-Dimethyleth-l-yloxy, Difluoromethoxy, Trifluoromethoxy, Pentafluoroethoxy, 2,2-Difluoroethoxy, 2,2,2-Trifluorethoxy,

G for methylene, (methyl)methylene, (ethyl)methylene, (prop-l-yl)methylene, (prop-2-yl)methylene, (but-l-yl)methylene, (but-2-yl)methylene, (pent-l-yl)methylene, (pent-2-yl)methylene, (pent-3- yl)methylene, (dimethyl)methylene, (diethyl)methylene, ethylene, n-propylene, (l-methyl)ethyl-l- ene, (2-methyl)ethyl-l-ene, n-butylene, 1-methylpropyl- 1 -ene, 2-methylpropyl- 1 -ene, 3-methylpropyl-l-ene, 1,1-dimethylethyl- 1 -ene, 2,2-dimethylethyl-l-ene, 1-ethylethyl- 1 -ene, 2-ethylethyl- 1-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- 1 -ene, 1 , 1 ,2-Trimethylethyl- 1 -ene, 1 ,2,2-Trimethylethyl- 1 -ene, 1 , 1 ,2,2-Tetramethylethyl- 1 - ene, n-Pentylene, 1 -Methylbutyl- 1-ene, 2-Methylbutyl-l-ene, 3-Methylbutyl-l-ene, 4-Methylbutyl-l- ene, 1,1 -Dimethylpropyl- 1-ene, 2,2-Dimethylpropyl-l-ene, 3,3-Dimethylpropyl-l-ene, 1,2- Dimethylpropyl- 1-ene, 1,3-dimethylpropyl-l-ene, 1-ethylpropyl-1-ene, n-hexylene, 1-methyl-pentyl-l-ene, 2-methylpentyl-l-ene, 3-methylpentyl-l-ene, 4-methylpentyl-l-ene, 1,1-di-methylbutyl-1-ene, 1,2-dimethylbutyl-l-ene, 1,3-di-methylbutyl-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,

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

Q represents one of the following specifically named groups Q1 to Q-25, whereby 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):

^{0 , 0 A} 0 0 Particularly preferred subject matter of the invention are compounds of the general formula (I), in which R ¹ is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, R ² is hydrogen, fluorine or chlorine, R ³ is hydrogen, fluorine, chlorine, bromine or methoxy, R ⁴ is fluorine, chlorine, bromine, cyano, NO ₂ , C(O)NH ₂ , C(S)NH ₂ , trifluoromethyl, ethynyl or propyn-1-yl, R ⁵ , R ⁶ and R ⁷ independently of one another are hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-Methyl)ethyl-1-ene, (2-Methyl)ethyl-1-ene, n-Butylene, 1-Methylpropyl-1-ene, 2-Methylpropyl- 1-ene, 3-Methylpropyl-1-ene, 1,1-Dimethylethyl-1-ene, 2,2-Dimethylethyl-1-ene, 1-Ethylethyl-1-ene, 2-Ethylethyl-1-ene, 1-(Prop-1-yl)ethyl-1-ene, 2-(Prop-1-yl)ethyl-1-ene, 1-(Prop-2-yl)ethyl-1-ene, 2- (Prop-2-yl)ethyl-1-ene, n-Pentylene, 1-Methylbutyl-1-ene, 2-Methylbutyl-1-ene, 3-Methylbutyl-1- en, 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 represent O (oxygen) or S (sulfur) and Q stands for one of the groupings Q-1 to Q-25 specifically mentioned above. The invention particularly relates to compounds of the general formula (I) in which R ¹ is hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, R ² is fluorine, R ³ is fluorine, R ⁴ is chlorine, bromine, cyano, NO ₂ , C(O)NH ₂ or C(S)NH ₂ , R ⁵ , R ⁶ and R ⁷ independently of one another are hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, n-pentylene or n-hexylene, X and Y 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. Particularly preferred subject matter of the invention are compounds of the general formula (I) in which R ¹ represents hydrogen, fluorine, chlorine or bromine, R ² represents fluorine, R ³ represents fluorine, R ⁴ stands for chlorine, bromine, cyano or NO ₂ ,

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 stands for methylene, (methyl)methylene or (ethyl)methylene,

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

Q stands for one of the groupings Q-1 to Q-25 specifically mentioned above.

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

R ¹ stands for hydrogen,

R ² is fluorine,

R ³ is fluorine,

R ⁴ stands for chlorine, bromine, cyano or NO ₂ ,

R ⁵ stands for hydrogen,

R ⁶ represents hydrogen, fluorine, chlorine, bromine or cyano,

R ⁷ stands for hydrogen,

G stands for methylene or (methyl)methylene,

X stands for O (oxygen) or S (sulfur),

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

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

R ¹ stands for hydrogen,

R ² is fluorine,

R ³ is fluorine,

R ⁴ stands for chlorine, bromine, cyano or NO ₂ ,

R ⁵ stands for hydrogen,

R ⁶ stands 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 stands for one of the groupings Q-1 to Q-25 specifically mentioned above.

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

R ¹ stands for hydrogen,

R ² is fluorine, R ³ is fluorine,

R ⁴ is chlorine, bromine or cyano,

R ⁵ stands for hydrogen,

R ⁶ stands for hydrogen or fluorine,

R ⁷ stands for hydrogen,

G stands for methylene,

X stands for O (oxygen),

Y stands for O (oxygen) and

Q for one of the above specifically mentioned groupings 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.

The general or preferred ranges of radical definitions given above apply both to the end products of the general formula (I) and to the starting materials or intermediates required for their preparation. These radical definitions can be combined as desired with one another, including between the preferred ranges given.

Particularly for reasons of higher herbicidal activity, better selectivity and/or better manufacturability, compounds according to the invention of the general formula (I) mentioned or their salts or their use 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.

If the compounds can form tautomers by hydrogen shift which are not structurally covered by the general formula (I), these tautomers are nevertheless included in the definition of the compounds of the general formula (I) according to the invention, unless a specific tautomer is the subject of consideration. For example, many Carbonyl compounds exist in both the keto form and the enol form, both forms being included in the definition of the compound of the general formula (I).

The compounds of the general formula (I) can exist as stereoisomers depending on the type and linkage of the substituents. The possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all included in the 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. The chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, and on a preparative scale to produce test samples for biological testing. Stereoisomers can also be produced selectively by using stereoselective reactions using optically active starting materials and/or auxiliary materials. The invention thus also relates to all stereoisomers which are encompassed by the general formula (I) but are not indicated with their specific stereoform, as well as mixtures thereof.

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

Methods which are generally known to the person skilled in the art from analogous cases can be used as isolation, purification and stereoisomer separation processes for compounds of the general formula (I), e.g. by physical processes such as crystallization, chromatography processes, 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.

With regard to the compounds according to the invention, the terms used above and below are explained. These are familiar to the person skilled in the art and have in particular the meanings explained below: Unless defined otherwise, the general rule for the designation of chemical groups is that the connection to the skeleton or the rest of the molecule is via the last-mentioned structural element of the chemical group in question, ie, for example, in the case of (C ₂ -C ₈ )-alkenyloxy via the oxygen atom, and in the case of heterocyclyl-(C ₁ -C ₈ )-alkyl or (C ₁ -C ₆ )-alkoxy-(C ₁ -C ₆ )-alkoxy-(C ₁ -C ₆ )-alkyl 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 with 1 to 8, or with 1 to 6 carbon atoms, such as (C ₁ -C ₁₀ )-, (C ₁ -C ₆ )- or (C ₁ -C ₄ )-alkylthio, e.g. (but not limited to) (C ₁ -C ₆ )-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1,1-Dimethylbutylthio, 1,2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2,2-Dimethylbutylthio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1,1,2-Trimethylpropylthio, 1,2,2-Trimethylpropylthio, 1-Ethyl-1-methylpropylthio and 1-Ethyl-2-methylpropylthio. “Alkoxy” means an alkyl radical bonded via an oxygen atom, e.g. B. (but not limited to) (C ₁ -C ₆ )-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methyl-propoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-di-methylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methyl-pentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethyl-butoxy, 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-methyl-propoxy 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 (C ₂ -C ₁₀ )-, (C ₂ -C ₆ )- or (C ₂ -C ₄ )-alkenoxy or (C ₃ -C ₁₀ )-, (C ₃ -C ₆ )- or (C ₃ -C ₄ )-alkynoxy. “Alkylcarbonyl” (alkyl-C(=O)-), unless defined otherwise elsewhere, stands according to the invention for alkyl radicals which are bonded to the skeleton via -C(=O)-, such as (C ₁ -C ₁₀ )-, (C ₁ -C ₆ )- or (C ₁ -C ₄ )-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 which are bonded to the skeleton via -OC(=O)-, such as (C ₁ -C ₁₀ )-, (C ₁ -C ₆ )- or (C ₁ -C ₄ )-alkoxycarbonyl. The number of C atoms refers to the alkyl radical in the alkoxycarbonyl group. Analogously, “alkenyloxycarbonyl” and “alkynyloxycarbonyl”, unless defined otherwise elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -OC(=O)-, such as (C ₂ -C ₁₀ )-, (C ₂ -C ₆ )- or (C ₂ -C ₄ )-alkenyloxycarbonyl or (C ₃ -C ₁₀ )-, (C ₃ -C ₆ )- or (C ₃ -C ₄ )-alkynyloxycarbonyl. The number of C atoms refers to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group. According to the invention, the term “alkylcarbonyloxy” (alkyl-C(=O)-O-), unless defined otherwise elsewhere, stands for alkyl radicals which are bonded to the skeleton with the oxygen via a carbonyloxy group (-C(=O)-O-), such as (C ₁ -C ₁₀ )-, (C ₁ -C ₆ )- or (C ₁ -C ₄ )-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 brackets 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 brackets 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 with preferably 6 to 14, in particular 6 to 10 ring carbon 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. In systematic terms, “aryl” is generally also included in the term “optionally substituted phenyl”. Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris-[alkyl]silyl, bis-[alkyl]arylsilyl, bis-[alkyl]alkylsilyl, tris-[alkyl]silylalkynyl, arylalkynyl, heteroaryl-alkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, Alkylamino, bis-alkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, 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 N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and can be unsubstituted or substituted, where the bonding site is located on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it can be fused to other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, multicyclic systems are also included, such as, for example, 8-aza-bicyclo[3.2.1]octanyl, 8-aza-bicyclo[2.2.2]octanyl or l-aza-bicyclo[2.2.1]heptyl. In the case of optionally substituted heterocyclyl, spirocyclic systems are also included, such as, for example, 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-lH-pyrrol-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydro- pyridin-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6-tetrahydropyridin-l- or 2- or 3- or 4- or

5- or 6-yl; 1,2,3,4-tetrahydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridin-1- or 2- or 3- or 4-yl; 2,3-dihydropyridin-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydro- pyridin-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-lH-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-lH-azepin-l- 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-azepine-2- or 3- or 4- or 5- or

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

7-yl; 2,3,4,7-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydrooxepin-2- or 3- or 4-yl; 2,3-dihydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydrooxepin-2- or 3- or 4-yl; 2,5-dihydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; oxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophen-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophen-2- or 3-yl; tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-di- hydro-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-ring and 4-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 with 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-lH-pyrazol-l- or 3- or 4- or 5-yl; 2,3-dihydro-lH-pyrazol-l- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4- imidazolidinyl; 2,3-dihydro-lH-imidazol-l- or 2- or 3- or 4-yl; 2,5-dihydro-lH-imidazol-l- or 2- or 4- or 5-yl; 4,5-dihydro-lH-imidazol-l- or 2- or 4- or 5-yl; hexahydropyridazin- 1- or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazin-l- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-Tetrahydropyridazin-l- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-Tetrahydropyridazin-l- or 3- or 4- or 5- or 6-yl; 3,4,5,6-Tetrahydropyridazin-3- or 4- or 5-yl; 4,5-Dihydro- pyridazin-3- or 4-yl; 3,4-Dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-Dihydropyridazin-3- or

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-tetrahydro- pyrimidin-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-

1- or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazin-l- or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazin-l- or 2- or 3-yl; 2,3-dihydropyrazin-2- or 3- or 5- or 6-yl; 2,5-dihydro- pyrazin-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-l,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-l,2-dithiol-3- or 4- or 5-yl; l,3-dithiolan-2- or 4-yl; l,3-dithiol-2- or 4-yl; l,2-dithian-3- or 4-yl; 3,4-dihydro-l,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-l,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-di- hydroisoxazol-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-

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

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

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-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4, 5,6,7- Tetrahydro-l,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 2,3-Dihydro-l,2-oxazepine-2- or 3- or

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-

1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; l,2-oxazepine-3- or 4- or 5- or 6- or 7-yl;

1,3-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-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

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

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-

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-

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-thia- zolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-l,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; l,4,2-dioxazol-3- or 5-yl; l,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-l,4,2-dioxazin-3- or 5- or 6-yl; l,4,2-dioxazin-3- or 5- or 6-yl; l,4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-l,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-dioxazepine-3- or 5- or 6- or 7-yl. Structural examples for optionally further substituted heterocycles are also listed below:

) ) ) )( ) ) ) ( ) ) / / ₎ .

' ,P • ₀ 0 I 0 The heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, haloalkylthio, 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, Hydroxycarbonylalkyl-aminocarbonyl, Alkoxycarbonylalkyl-aminocarbonyl, 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 the simultaneous substitution by several identical and/or structurally different residues.

If it is a partially or fully saturated nitrogen heterocycle, it can be linked to the rest of the molecule via both carbon and nitrogen.

The substituents listed below are possible substituents for a substituted heterocyclic radical, as are 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 appear on the hetero ring atoms, which can exist in different oxidation states, e.g. N and S, and then form, for example, the divalent groups N(O), S(O) (also abbreviated to SO) and S(O) ₂ (also abbreviated to SO ₂ ) in the heterocyclic ring. In the case of -N(O)- and -S(O)- groups, both enantiomers are included.

According to the invention, the term “heteroaryl” stands for heteroaromatic compounds, i.e. 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; lH-pyrrol-2-yl; IH-pyrrol-

3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, IH-Imidazol-l-yl; lH-Imidazol-2-yl; IH-Imidazol-

4-yl; lH-imidazol-5-yl; IH-pyrazol-l-yl; lH-pyrazol-3-yl; lH-pyrazol-4-yl; lH-pyrazol-5-yl, 1H-1,2,3-triazol-l-yl, lH-l,2,3-triazol-4-yl, lH-l,2,3-triazol-5-yl, 2H-l,2,3-Triazol-2-yl, 2H-l,2,3-Triazol-4-yl, lH-l,2,4-Triazol-l-yl, lH-l,2,4- Triazol-3-yl, 4H-l,2,4-triazol-4-yl, l,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, l,3, 4-oxadiazol-2-yl, l,2,3-oxadiazol-4-yl, l,2,3-oxadiazol-5-yl, l,2,5-oxadiazol-3-yl, azepinyl, Pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin- 3-yl, pyridazin-4-yl, l,3,5-triazin-2-yl, l,2,4-triazin-3-yl, l,2,4-triazin-5-yl, l,2, 4-Triazin-6-yl, l,2,3-Triazin-4-yl, l,2,3-Triazin-5-yl, 1,2,4-, 1,3,2-, 1,3, 6- and 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 and 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 also be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzofused or multiply fused heteroaromatics.

Preferred are, for example, quinolines (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); isoquinolines (e.g. isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; Cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6- naphthyridine; 2,7-naphthyridine; phthalazine; pyridopyrazines; Pyridopyrimidines; Pyridopyridazines; pteridines; Pyrimidopyrimidines. Examples of heteroaryl are also 5- or 6-membered benzo-fused rings from the group 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-benzothiophen-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophene-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-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1,2-benzisothiazol-7-yl. The term "halogen" means, for example, fluorine, chlorine, 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 is partially or fully substituted by identical or different halogen atoms, e.g. monohaloalkyl (= monohaloalkyl) such as e.g. CH ₂ CH ₂ Cl, CH ₂ CH ₂ Br, CHClCH ₃ , CH ₂ Cl, CH ₂ F; perhaloalkyl such as e.g. CCl ₃ , CClF ₂ , CFCl ₂ , CF ₂ CClF ₂ , CF ₂ CClFCF ₃ ; Polyhaloalkyl such as CH ₂ CHFCl, CF ₂ CClFH, CF ₂ CBrFH, CH ₂ CF ₃ ; The term perhaloalkyl also includes the term perfluoroalkyl. “Haloalkoxy” is e.g. OCF ₃ , OCHF ₂ , OCH ₂ F, OCF ₂ CF ₃ , OCH ₂ CF ₃ and OCH ₂ CH ₂ Cl; The same applies to haloalkenyl and other halogen-substituted radicals. The term "(C ₁ -C ₄ )-alkyl" used here as an example means a short form for straight-chain or branched alkyl with one to 4 carbon atoms according to the range specified for C atoms, ie 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. "(C ₁ -C ₆ )-alkyl", also include straight-chain or branched alkyl radicals with a larger number of C atoms, ie according to the example also the alkyl radicals with 5 and 6 C atoms. Unless specifically stated, the lower carbon skeletons, e.g. with 1 to 6 C atoms, or with 2 to 6 C atoms in the case of unsaturated groups, are preferred for hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, including in compound radicals. Alkyl radicals, including in compound radicals such as alkoxy, haloalkyl, etc., are e.g. methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, 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” also 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 radicals with one or more cumulated double bonds, such as, for example, 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, e.g. (but not limited to) (C ₂ -C ₆ )-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, for example, 1,3-butatrienyl or 3-penten-1-yn-1-yl. (C ₂ -C ₆ )-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, cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, which also includes 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 "(C ₃ -C ₇ )-cycloalkyl" means a short form for cycloalkyl with three to seven carbon atoms corresponding to the range for C atoms. In the case of spiro-(C ₅ -C ₉ )-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, spiro[3.3]heptan-2-yl. In the case of dispiro-(C ₇ -C ₈ )-alkanyl, dispirocyclic aliphatic systems are included, such as, for example, 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. B. also in the form (C ₁ -C ₁₀ )-alkylidene, means the residue of a straight-chain or branched open-chain hydrocarbon residue which is bonded via a double bond. Naturally, the only possible bonding sites for alkylidene are positions on the base structure where two H atoms can be replaced by a double bond; residues include e.g. =CH ₂ , =CH-CH ₃ , =C(CH ₃ )-CH ₃ , =C(CH ₃ )-C ₂ H ₅ or =C(C ₂ H ₅ )-C ₂ H _5. Cycloalkylidene means a carbocyclic residue which is bonded via a double bond. The term “alkylene”, e.g. also in the form (C ₁ -C ₈ )-alkylene, means the residue of a straight-chain or branched open-chain hydrocarbon residue which is bonded to other groups at two positions. "Alkoxyalkyl" means an alkoxy radical attached through an alkyl group and "alkoxyalkoxy" means an alkoxyalkyl radical attached through an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy. "Arylalkyl" means an aryl radical attached through an alkyl group, "heteroarylalkyl" means a heteroaryl radical attached through an alkyl group and "heterocyclylalkyl" means a heterocyclyl radical attached through an alkyl group. "Cycloalkylalkyl" means a cycloalkyl radical attached through 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 through an alkenyl group, "heteroarylalkenyl" means a heteroaryl radical attached through an alkenyl group, and "heterocyclylalkenyl" means a heterocyclyl radical attached through an alkenyl group. "Arylalkynyl" means an aryl radical attached through an alkynyl group, "heteroarylalkynyl" means a heteroaryl radical attached through an alkynyl group, and "heterocyclylalkynyl" means a heterocyclyl radical attached through 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 having 1 to 8, or having 1 to 6 carbon atoms, such as (C ₁ -C ₈ )-, (C ₁ -C ₆ )- or (C ₁ -C ₄ )-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 which are substituted by identical or different halogen atoms, such as, for example, F, Cl and Br, or by haloalkyl, such as, for example, 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 using known processes. The synthesis routes used and investigated start from commercially available or easily prepared heteroaromatic amines and from correspondingly substituted hydroxy esters. The groups G, Q, 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. The first key intermediate for the synthesis of the compounds of the general formula (Ia) according to the invention, in which X is sulfur (S) and Y is oxygen (O), is an optionally further substituted mercaptophenyl-1H-pyrimidine-2,4-dione. This is shown by way of example, but not by way of limitation, 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, for example but not restrictively, 2-fluoro-4-chloroaniline, is converted 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 by reaction with a suitable Aminoacrylic acid esters are converted into the corresponding optionally further substituted pyrimidine-2,4-dione, by way of example but not by way of limitation, 3-(4-chloro-2-fluorophenyl)-l-methyl-6-trifluoromethyl-lH-pyrimidine-2,4-dione, using a suitable base (e.g. sodium hydride or potassium tert-butoxide) in a suitable polar aprotic solvent (e.g. N,N-dimethylformamide) (Scheme 1). 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 (Ila), 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 represent, but are not limited to, fluorine, R ⁴ represents, but are not limited to, chlorine, and X represents, but are not limited to, sulfur.

Scheme 1.

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 in various ways into the desired compounds according to the invention of the general formula (Ia), in which X is sulfur (S) and Y is oxygen (O) (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 intermediates (III). In the following Scheme 2, Q, R ² , R ³ and R ⁴ have the above meanings according to the invention. Furthermore, R ¹ , R ⁵ , R ⁶ , R ⁷ are by way of example but not by limitation hydrogen, X is by way of example but not by limitation sulfur, Y is by way of example but not by limitation oxygen and G is by way of example but not by limitation CH2. The corresponding intermediate (III) described by way of example but not limitation in Scheme 2 can be converted into a corresponding intermediate oxyalkanoic acid ester (IVa, IVb) or the desired target compounds of the general formula (la) by reaction with a suitable, optionally further substituted iodoalkanoic acid ester (in Scheme 3 by way of example but not limitation an iodoacetic acid 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 acid esters can be prepared by methods known from the literature (cf. Eur. J. Org. Chem., 2006, 71, 8459; WO2012/037573; Organometallics, 2009, 28, 132).

Scheme 2

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)]. The desired substituted N-phenyluracils of the general formula (la) can be prepared by reacting the corresponding intermediate acid (V) with a suitable compound QH using 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-trioxatriphosphorinane-2,4,6-trioxide) and suitable bases (e.g. diisopropylethylamine, triethylamine) in a suitable polar aprotic solvent (e.g. dichloromethane, chloroform). Alternatively, the ethyl ester (IVa) can be converted into the corresponding desired substituted N-phenyluracil of the general formula (la) by coupling with a suitable compound QH mediated by a suitable Lewis acid (e.g. indium(III) chloride) (cf. WO2011/1307088).

The preparation of the compounds of general formula (I), in which X and Y represent, by way of example but not by way of 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)-l-methyl-6-trifluoromethyl-lH-pyrimidine-2,4-dione (Via). For this purpose, a suitable substituted aniline, for example but not restrictively 2,5-difluoroaniline, is converted 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 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 for example but not restrictively 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 are by way of example but not limitation fluorine and R ⁴ is by way of example but not limitation nitro.

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 4 = nitro) 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)). 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 diazotization reagent, e.g. tert-butyl nitrite (t-BuONO), boron trifluoride etherate (BF ₃ -OEt ₂ ) in suitable polar-aprotic solvents (e.g. dichloromethane (DCM), dimethoxyethane), (iv) reaction with acetic anhydride and (v) release of the Hydroxy group can be obtained by splitting off the acetyl protective 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, so that the desired substituted N-phenyluracil (Ic) can be obtained in this way. In the following scheme 4, Q and R ² have the above meanings according to the invention. Furthermore, R ³ is by way of example but not limitation fluorine, R ⁴ is by way of example but not limitation chlorine or nitro, R ¹ , R ⁵ , R ⁶ , R ⁷ are by way of example but not limitation hydrogen, X and Y are by way of example but not limitation oxygen and G is by way of example but not limitation CH ₂ .

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) with a suitable substituted 2-carbonylalkylthio-l-hydroxybenzene (VIII) using a suitable base (e.g. potassium carbonate) in a suitable polar aprotic solvent (e.g. N,N-dimethylformamide (DMF)). The intermediate (VIII) used for this purpose can be prepared by multi-step synthesis analogous to the synthesis of the 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, so that the desired substituted N-phenyluracil (le) can be obtained in this way. In the following Scheme 5, Q and R ² have the above meanings according to the invention. Furthermore, R ³ is by way of example but not limitation fluorine, R ⁴ is by way of example but not limitation chlorine or nitro, R ¹ , R ⁵ , R ⁶ , R ⁷ are by way of example but not limitation hydrogen, X is by way of example but not limitation oxygen, Y is by way of example but not limitation sulfur and G is by way of example but not limitation CH2.

Scheme 5.

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 are 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, the intermediate cleavage of the thiol group using a suitable protective group is necessary. 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 the following scheme 6, Q, R ² , R ³ , and R ⁴ have the above meanings according to the invention. Furthermore, R ¹ , R ⁵ , R ⁶ , R ⁷ are examples but not restrictive of hydrogen, X and Y are examples but not restrictive of sulfur and G is examples but not restrictive of CH2. Furthermore, for better clarity, the reaction pathways in Scheme 6 below are described by way of example but not restrictive of iodoacetic acid esters. Comparable haloalkanecarboxylic acids (halogen = bromine or chlorine) are also suitable for coupling with intermediate (IX).

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. The ¹ H-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz at ¹ H-NMR, solvent CDCl ₃ , CD ₃ OD or d ₆ -DMSO, internal standard: tetramethylsilane δ = 0.00 ppm) were obtained using an instrument from Bruker, and the designated signals have the meanings listed below: br = broad(es); 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 diastereomer mixtures, either the significant signals of both diastereomers or the characteristic signal of the main diastereomer are given. The abbreviations used for chemical groups have, for example, the following meanings: Me = CH ₃ , Et = CH ₂ CH ₃ , t-Hex = C(CH ₃ ) ₂ CH(CH ₃ ) ₂ , t-Bu = C(CH ₃ ) 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-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate 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-ethyl-carbodiimide 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. After column chromatography on silica gel with an n-heptane/ethyl acetate gradient, 0.122 g (71% of theory) of a colorless solid was obtained. ¹ H-NMR (CDCl ₃ δ, 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).

e.g. I.7-10: Cyclobutylmethyl-(2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6- dihydropyrimidine- 1 (2H)- yl]phenoxy }phenoxy)acetat

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) and then successively 1-hydroxy- IH-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.

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

'H-NMR (CDCl ₃ δ, 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).

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

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.

After column chromatography on silica gel with an n-heptane/ethyl acetate gradient, 0.170 g (86% of theory) of a colorless solid was obtained. ¹ H-NMR (CDCl ₃ δ, ppm) 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.04 (m, 1H), 7.01-6.97 (m, 1H), 6.91- 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).

e.g. I.8-1 : Cyclopropylmethyl-(2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6- dihydropyrimidine- 1 (2H)- yl]phenoxy }phenoxy)acetat

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) and then successively 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 left to stand overnight and the subsequent thin-layer chromatographic reaction control showed incomplete conversion, so 1-hydroxy-1H-benzotriazole hydrate (148 mg, 1.10 mmol), l-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (210 mg, 1.10 mmol) and catalytic amounts of 4-dimethylaminopyridine (10 mg) were added again. The mixture was stirred for a further 5 hours at room temperature and almost complete conversion was found by thin-layer chromatographic reaction control. Water was added to the reaction mixture, the phases were separated using a separator cartridge and the solvent was removed in vacuo. After column chromatography on silica gel with an n-heptane/ethyl acetate gradient, cyclopropylmethyl (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}phenoxy)acetate (477 mg, 95% of theory) was obtained as a colorless oil. ¹ H NMR (CDCl ₃ δ, 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).

e.g. I.9-1 : Cyclopropylmethyl-(2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6- dihydropyrimidine- 1 (2H)- yl]phenoxy }phenoxy)acetat

Cyclopropylmethyl-(2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(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 N,N-dimethylacetamide and stirred for 1 hour at an oil bath temperature of 180 degrees Celsius. After TLC control, which indicated complete conversion, the reaction mixture was poured into 10 mL water and extracted several times with ethyl acetate. The combined organic phases were washed twice with saturated brine, then dried over sodium sulfate and, after filtration, concentrated in vacuo.

Purification of the crude product obtained by column chromatography on silica gel with an n-heptane/ethyl acetate gradient gave 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) in the form of a colorless oil. ¹ H-NMR (CDCI ₃ δ, ppm): 7.49 (d, 1H), 7.20 (m, 2H), 7.04 (dt, 1H), 6.88 (dd, 1H), 6.80 (d, 1H), ), 6.26

(s, 1H), 4.64 (s, 2H), 3.94 (d, 2H), 3.49 (s, 3H), 1.10 (m, 1H), 0.56 (m, 2H), 0.25 (m, 2H).

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 the formula (I.1) are the compounds I.1-1 to I.1-25, in which 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 No. 1 to 25 for Q of Table 1. Table 1: Table I.2: Preferred compounds of the formula (I.2) are the compounds I.2-1 to I.2-25, in which 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 the formula (I.3) are the compounds I.3-1 to I.3-25, in which 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 the formula (I.4) are the compounds I.4-1 to I.4-25, in which 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 defined by the meaning of the respective entries No. 1 to 25 for Q of the

Table 1 defined.

Table I.5: Preferred compounds of the formula (I.5) are the compounds I.5-1 to I.5-25, in which 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 No. 1 to 25 for Q of Table 1.

Table I.6: Preferred compounds of the formula (I.6) are the compounds I.6-1 to I.6-25, in which 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 No. 1 to 25 for Q of Table 1.

Table I.7: Preferred compounds of the formula (I.7) are the compounds I.7-1 to I.7-25, in which 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 No. 1 to 25 for Q of Table 1.

Table I.8: Preferred compounds of the formula (I.8) are the compounds I.8-1 to I.8-25, in which 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 No. 1 to 25 for Q of the Table 1 defined.

Table I.9: Preferred compounds of the formula (I.9) are the compounds I.9-1 to I.9-25, in which 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.

Table I.10: Preferred compounds of the formula (I.10) are the compounds I.10-1 to I.10-25, in which 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 No. 1 to 25 for Q of Table 1.

Table I.11: Preferred compounds of the formula (I.11) are the compounds I.11-1 to I.11-25, in which 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 No. 1 to 25 for Q of Table 1. Table I.12: Preferred compounds of the formula (I.12) are the compounds I.12-1 to I.12-25, in which 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 the formula (I.13) are the compounds I.13-1 to I.13-25, in which 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 the formula (I.14) are the compounds I.14-1 to I.14-25, in which 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 the formula (I.15) are the compounds I.15-1 to I.15-25, in which 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 the formula (I.16) are the compounds I.16-1 to I.16-25, in which 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 the formula (I.17) are the compounds I.17-1 to I.17-25, in which 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 the formula (I.18) are the compounds I.18-1 to I.18-25, in which 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 the formula (1.19) are the compounds 1.19-1 to 1.19-25, in which 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 No. 1 to 25 for Q of Table 1.

Table 1.20: Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-25, in which 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 No. 1 to 25 for Q of Table 1.

Table 1.21: Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-25, in which 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 No. 1 to 25 for Q of Table 1.

Table 1.22: Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-25, in which 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 No. 1 to 25 for Q of Table 1. Table I.23: Preferred compounds of the formula (I.23) are the compounds I.23-1 to I.23-25, in which 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 the formula (I.24) are the compounds I.24-1 to I.24-25, in which 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 the formula (I.25) are the compounds I.25-1 to I.25-25, in which 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 the formula (1.26) are the compounds 1.26-1 to 1.26-25, in which 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 No. 1 to 25 for Q of Table 1.

Table 1.27: Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-25, in which 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 No. 1 to 25 for Q of Table 1.

Table 1.28: Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-25, in which 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 No. 1 to 25 for Q of Table 1.

Table 1.29: Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-25, in which 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 No. 1 to 25 for Q of Table 1. Table I.30: Preferred compounds of the formula (I.30) are the compounds I.30-1 to I.30-25, in which 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 the formula (I.31) are the compounds I.31-1 to I.31-25, in which 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 the formula (I.32) are the compounds I.32-1 to I.32-25, in which 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 the formula (I.33) are the compounds I.33-1 to I.33-25, in which 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 of selected examples of compounds of the general formula (I) are given in two different ways, namely (a) classical NMR evaluation and interpretation or (b) in the form of 1H-NMR peak lists according to the method described below. a) classical NMR interpretation Ex. 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 The ¹ H NMR data of selected examples are recorded in the form of ¹ H NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity are listed 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: δ ₁ (intensity ₁ ⁾ ; δ ₂ (intensity ₂ );……..; 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, several peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown. To calibrate the chemical shift of ¹ H NMR spectra, we use tetramethylsilane and/or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may or may not appear in NMR peak lists.

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

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

When reporting compound signals in the delta region of solvents and/or water, our lists of ¹ H NMR peaks show the common solvent peaks, for example peaks of DMSO in DMSO-D ₆ and the peak of water, which usually have high intensity on average.

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%).

Such stereoisomers and/or impurities may be typical for the respective manufacturing process. Their peaks can thus help to identify the reproduction of our manufacturing process based on “by-product fingerprints”.

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

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

The present invention further 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 identified 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 a herbicide and/or plant growth regulator, preferably in crops of useful and/or ornamental plants.

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 formulas (1.1) to (1.33) and/or salts thereof, each 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 cultivation area.

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 formulas (1.1) to (1.33) and/or salts thereof, each 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 monocotyledonous 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 cultivation area (i.e. area on which the unwanted plants will grow).

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

The compounds of the general formula (I) according to the invention or the agents according to the invention can be applied, for example, in the pre-sowing (if necessary also by incorporation into the soil), pre-emergence and/or post-emergence method. Some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention may be mentioned as examples, without the mention being intended to be a restriction to certain species.

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 growth in crops of useful plants or ornamental plants, wherein the useful plants or ornamental plants are transgenic plants in a preferred embodiment.

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

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

Dicotyledonous weeds 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.

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

When the compounds of the general formula (I) according to the invention are applied to the green parts of the plant by the post-emergence method, 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 that is harmful to the crop plants is eliminated very early and sustainably.

Although the compounds of the general formula (I) according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, e.g. 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 amount applied. For these reasons, the present compounds are very suitable for the selective control of undesirable plant growth in plant crops such as agricultural crops or ornamental plants.

In addition, the compounds of general formula (I) according to the invention (depending on their respective structure and the amount applied) have excellent growth-regulating properties in cultivated plants. They have a regulating effect on the plant's own metabolism and can therefore be used to specifically influence plant constituents and to facilitate harvesting, for example by triggering desiccation and stunting. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as this can reduce or completely prevent lodging, for example.

Due to their herbicidal and plant growth regulating properties, the compounds of the general formula (I) according to the invention can also be used to control harmful plants in Cultures of plants modified genetically or through conventional mutagenesis are used. 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 affect the harvested product in terms of quantity, quality, storability, composition and special ingredients. Transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition of the harvested product are known.

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. of 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.

Preferably, the compounds of the 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.

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 harmful plants 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 special ingredients. For example, 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 can be tolerance or resistance to abiotic stressors, e.g. heat, cold, drought, salt and ultraviolet radiation.

Preference is given to using the compounds of the general formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, e.g. cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables. Preferably, the compounds of the general formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.

Conventional ways of producing new plants that have modified properties compared to existing plants include classical breeding methods and the creation of mutants. Alternatively, new plants with modified properties can be created using genetic engineering techniques.

Numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known to the person skilled in the art. For such genetic manipulations, nucleic acid molecules can be introduced into plasmids that allow mutagenesis or a sequence change through recombination of DNA sequences. Using standard methods, for example, base exchanges can be carried out, partial sequences can be removed or natural or synthetic sequences can be added. Adapters or linkers can be attached to the fragments to connect the DNA fragments to one another.

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 which specifically cleaves transcripts of the above-mentioned gene product.

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

When nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any compartment of the plant cell. However, in order to achieve localization in a specific compartment, the coding region can be linked to DNA sequences that ensure localization in a specific compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The 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. The transgenic plants can in principle be plants of any plant species, ie both monocotyledonous and dicotyledonous plants.

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.

Preferably, the compounds of the general formula (I) according to the invention can be used in transgenic cultures which are resistant to growth factors, 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.

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 to the application in the respective transgenic crop, for example a modified or specifically expanded spectrum of weeds 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.

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.

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

It is also preferred for use in soya before or after emergence.

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

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

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

(b) one or more other substances selected from groups (i) and/or (ii):

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

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

The other agrochemically active substances of component (i) of an agent according to the invention are preferably selected from the group of substances mentioned in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

A herbicidal or plant growth regulating agent according to the invention preferably comprises one, two, three or more formulation aids (ii) customary in plant protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers which are solid at 25 °C and 1013 mbar, preferably adsorbent, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoaming agents, water, organic solvents, preferably organic solvents which 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 usual preparations. The invention therefore also relates to herbicidal and plant growth regulating agents which contain compounds of the general formula (I) and/or salts thereof. The compounds of the general formula (I) according to the invention and/or salts thereof can be formulated in various ways, depending on which biological and/or chemical-physical parameters are 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), dressing agents, granules for broadcast and soil application, granules (GR) in the form of micro-, spray, lifting 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, Hv Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, NY; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, NY1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY1964; Schönfeldt, "Grenzflächenaktive Äthylenoxid-addukte", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th edition 1986. Wettable powders are preparations that can be evenly dispersed in water and which, in addition to the active ingredient and a diluent or inert substance, also contain surfactants of an ionic and/or non-ionic nature (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, blower mills and air jet mills and mixed simultaneously or subsequently with the formulation aids. Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and/or non-ionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: 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.

Dusting agents 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.

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, adding surfactants, such as those listed above for the other formulation types.

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.

Granules can be produced either by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates using adhesives, e.g. polyvinyl alcohol, polyacrylic acid sodium or mineral oils, to the surface of carrier materials such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the usual way for the production of fertilizer granules - if desired in a mixture with fertilizers.

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

For the production of disc, fluidized bed, extruder and spray granules, see for example the process 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.

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.

In wettable powders, for example, the active ingredient concentration is about 10 to 90% by weight, the rest 100% by weight consists of usual formulation components. In emulsifiable concentrates, the active ingredient concentration can be about 1 to 90, preferably 5 to 80% by weight. Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient. In water-dispersible granules, the active ingredient content depends in part 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% by weight, preferably between 10 and 80% by weight.

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 agents which influence the pH value and viscosity. Examples of formulation aids are described in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998).

The compounds of the 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-made formulation or as tank mixes. The combination formulations can be prepared on the basis of the abovementioned formulations, taking into account the physical properties and stabilities of the active ingredients to be combined.

Suitable combination partners for the compounds of general formula (I) according to the invention in mixture formulations or in tank mixes are, for example, known active substances which are based on a 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, 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.

Of particular interest is the selective control of harmful plants in crops of useful and ornamental plants. Although the compounds of the general formula (I) according to the invention already have very good to sufficient selectivity in many crops, phytotoxicities can in principle occur in some crops and especially in the case of mixtures with other herbicides which are less selective. In this regard, combinations of compounds of the general formula (I) according to the invention which contain 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 content, reduce the phytotoxic side effects of the herbicides/pesticides used, e.g. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soy, preferably cereals.

The weight ratio of herbicide (mixture) to safener generally depends on the amount of herbicide applied and the effectiveness 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 the general formula (I) or mixtures thereof with other herbicides/pesticides and can be provided and applied as a ready-made formulation or tank mix with the herbicides.

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

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 harmful plants, 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, 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 both to pre-emergence and post-emergence applications.

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.

The application as a stalk shortener can be carried out at different stages of plant growth. For example, application after tillering at the beginning of longitudinal growth is preferred.

Alternatively, when used as a plant growth regulator, seed treatment can also be considered, which includes various seed dressing and coating techniques. The application rate depends on the individual techniques and can be determined in preliminary tests.

Known active ingredients which are based on the 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 combination partners for the compounds of the general formula (I) in mixture formulations or in the tank mix, 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 the literature cited therein.

Known herbicides or plant growth regulators that can be combined with compounds of the general formula (I) include 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, Amicarbazone, Amidochlor, Amidosulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, Aminocyclopyrachlor, Aminocyclopyrachlor-potassium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid-dimethylammonium, Aminopyralid-tripromine, Amitrol, Ammoniumsulfamates, Anilofos, Asulam, Asulam-potassium, Asulam-sodium, Atrazine, Azafenidine, Azimsulfuron, Beflubutamide, (S)-(-)- Beflubutamide, Beflubutamide-M, Benazolin, Benazolin-ethyl, Benazolin-dimethylammonium, Benazolin-Klaium, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Bensulide, Bentazon, Bentazon-sodium, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-sodium, Bipyrazone, Bispyribac, Bispyribac-sodium, Bixlozon, Bromacil, Bromacil-lithium, Bromacil-sodium, Bromobutide, Bromofenoxime, Bromoxynil, Bromoxynil butyrate, Bromoxynil potassium, Bromoxynil heptanoate and Bromoxynil octanoate, Busoxinon, Butachlor, Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylate, Cafenstrol, Cambendichlor, Carbetamide, Carfentrazone, Carfentrazone- Ethyl, chloramben, chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chlorambenmethylammonium, chlor amben-sodium, chlorbromuron, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, cinidon, cinidon-ethyl, cinmethylin, exo-(+)- cinmethylin, dh (lR,2S,4S)-4-isopropyl-l-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, exo-(-)-cinmethylin, dh (lR,2S,4S)-4-isopropyl-l-methyl-2-[(2-methylbenzyl)oxy]-7- oxabicyclo[2.2.1]heptane, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-ethyl, clodinafop- propargyl, clomazone, clomeprop, clopyralid, clopyralid-methyl, clopyralid-olamine, clopyralid- potassium, clopyralid-tripomin, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D (as well as the ammonium, butotyl, butyl, choline, diethylammonium, dimethylammonium, diolamine, doboxyl, dodecylammonium, Etexyl, Ethyl, 2-Ethylhexyl, Heptylammonium, Isobutyl, Isooctyl, Isopropyl, Isopropylammonium, Lithium, Meptyl, Methyl, Potassium, Tetradecylammonium, Triethylammonium, Triisopropanolammonium, Tripromin and Trolamine salts thereof), 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl, 2,4-DB-potassium and 2,4-DB-sodium, Daimuron (Dymron), Dalapon, Dalapon Calcium, Dalapon Magnesium, Dalapon Sodium, Dazomet, Dazomet Sodium, n-Decanol, 7-Deoxy-D-sedoheptulose, Desmedipham, Detosyl-pyrazolate (DTP), Dicamba and its salts (eg Dicamba-biproamine, Dicamba-N,N-Bis(3- aminopropyl)methylamine, dicamba-butotyl, dicamba-choline, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolaminemmonium, dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl, dicamba-monoethanolamine, dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine), dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl- l,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, Dichlorprop-butotyl, Dichlorprop-dimethylammonium, Dichlorprop-etexyl, Dichlorpropethylammonium, Dichlorprop-isoctyl, Dichlorprop-methyl, Dichlorprop-potassium, Dichlorprop-sodium, Dichlorprop-P, Dichlorprop-P-dimethylammonium, Dichlorprop-P-etexyl, Dichlorprop-P-potassium, Dichlorprop-sodium, Diclofop, Diclofop-methyl, Diclofop-P, Diclofop-P-methyl, Diclosulam, Difenzoquat, Difenzoquat-metilsulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr-sodium, Dimefuron, Dimepiperate, Dimesulfazet, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimetrasulfuron, Dinitramine, Dinoterb, Dinoterb-Acetate, Diphenamid, Diquat, Diquat Dibromide, Diquat Dichloride, Dithiopyr, Diuron, DNOC, DNOC Ammonium, DNOC Potassium, DNOC Sodium, Endothal, Endothal Diammonium, Endothal Dipotassium, Endothal Disodium, Epyrifenacil (S-3100), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethametsulfuron Methyl, Ethiozine, Ethofumesate, Ethoxyfen, Ethoxyfen Ethyl, Ethoxysulfuron, Etobenzanide, F-5231, ie N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-lH-tetrazol-l-yl]-phenyl]-ethanesulfonamide, F-7967, ie 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-lH-benzimidazol-4-yl]-l-methyl-6-(trifluoromethyl)pyrimidine-2,4(lH,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrion, fentrazamide, 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 sodium, Flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupropanate sodium, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen sodium, foramsulfuron, foramsulfuron sodium, fosamine, fosamine ammonium, glufosinate, Glufosinate Ammonium, Glufosinate Sodium, L- Glufosinate Ammonium, L- Glufosinate Sodium, Glufosinate P Sodium, Glufosinate P Ammonium, Glyphosate, Glyphosate Ammonium, Glyphosate Isopropylammonium, Glyphosate Diammonium, Glyphosate Dimethylammonium, Glyphosate Potassium, Glyphosate Sodium, Glyphosate Sesquinodium and Glyphosate Trimesium, H-9201, i.e. O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl-isopropylphosphoramidothioate, Halauxifen, Halauxifen-methyl, Halosafen, Halosulfuron, Halosulfuron-Methyl, Haloxyfop, Haloxyfop-P, Haloxyfop-Ethoxyethyl, Haloxyfop-P-Ethoxyethyl, Haloxyfop-Methyl, Haloxyfop-P-Methyl, Haloxif op-Sodium, Hexazinone, HNPC-A8169, ie Prop-2-yn-l-yl (2S)- 2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propanoate, HW-02, ie l-(Dimethoxyphosphoryl)-ethyl-(2,4-dichlorophenoxy)acetate, Hydantocidin, Icafolin, Icafolin-Methyl, Imazamethabenz, Imazamethabenz-Methyl, Imazamox, Imazamox-Ammonium, Imazapic, Imazapic-Ammonium, Imazapyr, Imazapyr-Isopropylammonium, Imazaquin, Imazaquin-Ammonium, Imazaquin-Methyl, Imazethapyr, Imazethapyr-Ammonium, Imazosulfuron, Indanofan, Indaziflam, Indolauxipyr, lodosulfuron, lodosulfuron-methyl, lodosulfuron-methyl sodium, Ioxynil, loxynil lithium, -octanoate, -potassium and sodium, Ipfencarbazone, Iptriazopyride, ie 3-[(Isopropylsulfonyl)methyl]-N-(5-methyl- l,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)[l,2,4]triazolo-[4,3-a]pyridine-8-carboxamide, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Carbutilate, KUH-043, ie 3-({[5-(Difluoromethyl)-l-methyl-3-(trifluoromethyl)-lH-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-l,2-oxazole, Ketospiradox, Ketospiradox potassium, Lactofen, Lenacil, Linuron, MCPA, MCPA-Butotyl, -Butyl, -Dimethylammonium, -Diolamine, -2-Ethylhexyl, -Ethyl, -Isobutyl, Isoctyl, -Isopropyl, -Isopropylammonium, -Methyl, Olamine, -Potassium, -Sodium and -Trolamine, MCPB, MCPB-Methyl, -Ethyl and -Sodium, Mecoprop, Mecoprop-Butotyl, Mecoprop-dimethylammonium, Mecoprop-Diolamine, Mecoprop-Etexyl, Mecoprop-Ethadyl, Mecoprop-Isoctyl, Mecoprop-Methyl, Mecoprop-Potassium, Mecoprop-Sodium, and Mecoprop-Trolamine, Mecoprop-P, Mecoprop-P-Butotyl, -Dimethylammonium, -2-Ethylhexyl and - Potassium, Mefenacet, Mefluidid, Mefluidid-Diolamine, Mefluidid-Potassium, Mesosulfuron, Mesosulfuron-Methyl, Mesosulfuron-Sodium, Mesotrione, Methabenzthiazuron, Metam, Metamifop, Metamitron, Metazachlor, Metazosulfuron, Methabenzthiazuron, Methiopyrsulfuron, Methiozolin, Methyl isothiocyanate, Metobromuron, Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metproxybicyclon, Metribuzin, Metsulfuron, Metsulfuron-Methyl, Molinate, Monolinuron, Monosulfuron, Monosulfuron-Methyl, MT-5950, ie N-[3-Chloro-4-(l-methylethyl)-phenyl]-2-methylpentanamide, NGGC-011, Napropamide, NC-310, ie 4-(2,4-Dichlorobenzoyl)-l-methyl-5-benzyloxypyrazole, Neburon, Nicosulfuron, Nonanoic Acid (Pelargonic Acid), Norflurazon, Oleic Acid (Fatty Acids), Orbencarb, Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Paraquat Dichloride, Paraquat Dimethyl Sulfate, Pebulate, Pendimethalin, Penoxsulam, Pentachlorophenol, Pentoxazone, Pethoxamide, Petroleum Oil, Phenmedipham, Phenmedipham Ethyl, Picloram, Picloram Dimethylammonium, Picloram Etexyl, Picloram Isoctyl, Picloram Methyl, Picloram Olamine, Picloram Potassium, Picloram Triethylammonium, Picloram Tripromin, Picloram Trolamine, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron, Primisulfuron Methyl, Prodiamine, Profoxydim, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone Sodium, Propyrisulfuron, Propyzamide, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen Ethyl, Pyraquinate, Pyrasulfotol, Pyrazolynate (Pyrazolate), Pyrazosulfuron, Pyrazosulfuron Ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz Isopropyl, Pyribambenz Propyl, Pyribenzoxime, Pyributicarb, Pyridafol, Pyridate, Pyriftalide, Pyriminobac, Pyriminobac -Methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac Sodium, Pyroxasulfone, Pyroxsulam, Quinclorac, Quinclorac Dimethylammonium, Quinclorac Methyl, Quinmerac, Quinoclamin, Quizalofop, Quizalofop Ethyl, Quizalofop-P, Quizalofop-P-Ethyl, Quizalofop-P-Tefuryl, QYM201 , ie 1 - { 2-chloro-3- [(3-cyclopropyl-5-hydroxy- 1 -methyl- 1 H-pyrazol-4-yl)carbonyl] -6- (trifluoromethyl)phe-nyl}piperidin-2-one, Rimsulfuron, Saflufenacil, Sethoxydim, Siduron, Simazine, Simetryn, SL-261, Sulcotrione, Sulfentrazone, Sulfometuron, Sulfometuron-Methyl, Sulfosulfuron, , SYP-249, ie l-Ethoxy-3-methyl-l-oxobut-3-en-2-yl-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, ie l-[7-Fluoro-3-oxo-4-(prop-2-yn-l-yl)-3,4-dihydro-2H-l,4-benzoxazin-6-yl]- 3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts, e.g. TCA-ammonium, TCA-calcium, TCA-ethyl, TCA-magnesium, TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumetone, terbuthylazine, terbutryn, tetflupyrolimet, thaxtomin, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamon, triallate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, Triclopyr, Triclopyr-Butotyl, Triclopyr-Choline, Triclopyr-Ethyl, Triclopyr-Triethylammonium, Trietazine, Trifloxysulfuron, Trifloxysulfuron-Sodium, Trifludimoxazine, Trifluralin, Triflusulfuron, Triflusulfuron-Methyl, Tritosulfuron, Urea Sulfate, Vernolate, XDE-848, ZJ-0862, i.e. 3,4-Dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, 3-(2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-l(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid methyl ester, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-l(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester, 3-(2-chloro-

4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-l(2H)-yl)phenyl)-5-methyl-4,5- dihydroisoxazole-5-carboxylic acid, Ethyl [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)- 3,6-dihydropyrimidin- 1 (2H)-yl]phenoxy }pyridin-2-yl)oxy] acetate, 3-chloro-2-[3- (difluoromethyl)isoxazolyl-5-yl]phenyl-5-chloropyrimidin-2-yl ether, 2-(3,4-Dimethoxyphenyl)-4-[(2- hydroxy-6-oxocyclohex- 1 -en- 1 -yl)carbonyl] -6-mcthyl py l idazi n-3(2H)-one, 2-({2-[(2- Methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-l,3-dione, (5-Hydroxy-l-methyl- lH-pyrazol-4-yl)(3,3,4-trimethyl- 1 , 1 -dioxido-2, 3 -dihydro- 1 -benzothiophen-5-yl)methanone, 1 -Methyl-4- [(3,3,4-trimethyl- 1 , 1 -dioxido-2, 3 -dihydro- 1 -benzothiophen-5-yl)carbonyl]- lH-pyrazol-5-yl propane- 1 - sulfonate, 4- { 2-Chloro-3-[(3,5-dimethyl- IH-pyrazol- 1 -yl)methyl] -4-(methylsulfonyl)benzoyl } - 1 -methyl- lH-pyrazol-5-yl-l,3-dimethyl-lH-pyrazol-4-carboxylate; Cyanomethyl 4-amino-3-chloro-5-fluoro-6-(7- fluor-lH-indol-6-yl)pyridine-2-carboxylate, Prop-2-yn-l-yl 4-amino-3-chloro-5-fluoro-6-(7-fluor-lH-indol- 6-yl)pyridine-2-carboxylate, Methyl 4-amino-3-chloro-5-fluoro-6-(7-fluor-lH-indol-6-yl)pyridine-2-carboxylate, Benzyl 4-amino-3-chloro-5-fluoro-6-(7-fluor-lH-indol-6-yl)pyridine-2-carboxylate, Ethyl 4-amino-3-chloro-5-fluoro-6-(7-fluor-lH-indol-6-yl)pyridine-2-carboxylate, Methyl 4-amino-3-chloro-5-fluoro- 6-(7 -fluor- 1 -isobutyryl- 1 H-indol-6-yl)pyridine-2-carboxylate, Methyl 6-( 1 -acetyl-7 -fluor- 1 H-indol-6-yl)- 4-amino-3-chloro-5-fluoropyridine-2-carboxylate, Methyl 4-amino-3-chloro-6-[l-(2,2-dimethylpropanoyl)-7- fluor-lH-indol-6-yl]-5-fluoropyridine-2-carboxylate, Methyl 4-amino-3-chloro-5-fluoro-6-[7-fluor-l- (methoxyacetyl)-lH-indol-6-yl]pyridine-2-carboxylate, Potassium 4-amino-3-chloro-5-fluoro-6-(7-fluor-lH- indol-6-yl)pyridine-2-carboxylate, Sodium 4-amino-3-chloro-5-fluoro-6-(7-fluor-lH-indol-6-yl)pyridine-2- carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridine-2-carboxylate, 4-hydroxy- l-methyl-3-[4-(tifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 3-(5-tert-butyl-l,2-oxazol-3-yl)-4- hydroxy-l-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-l- methylimidazolidin-2-one, 4-hydroxy-l-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-l-en-l-yl)carbonyl]-l,5-dimethyl-3-(2- methylphenyl)quinazolin-2,4(lH,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-l-en- l-yl)carbonyl]-l-methylquinazolin-2,4(lH,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4- ylmethyl)benzoyl] -3-hydroxycyclohex-2-en- 1 -one, 1 -(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin- 1 - ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-carboxyethyl)-4- (pyridazin-3-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(Pyrimidin-2-yl)-l-(2-sulfoethyl)pyridazin-l-ium salt 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-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6- dihydropyrimidin-l(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, (E)-2- (Trifluoromethyl)benzaldehyde-O-{2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoyl}oxime, 2-fluoro-N- (5-methyl-l,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, (2R)-2-[(4-amino- 3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanecarboxylic acid, 2-ethoxy-2-oxoethyl-l-{2-chloro-4-fluoro-5-[3- methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}cyclopropanecarboxylate, 2- Methoxy-2-oxoethyl-l-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin- 1 (2H)-yl]phenoxy Jcyclopropanecarboxylate, { [(1 - { 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4- (trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}acetic acid, 2-(2- bromo-4-chlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, Methyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6- dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin- 1 (2H)-yl]phenyl } -3a,4,5,6-tetrahydro-6aH- cyclopenta[d][l,2]oxazole-6a-carboxylate, Ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4- (trifluoromethyl)-3,6-dihydropyrimidin- 1 (2H)-yl]phenyl } -3a,4,5,6-tetrahydro-6aH- cyclopentafd] [1 ,2]oxazole-6a-carboxylate

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-dienoic acid, 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 [(C ₅ HnNO ₄ )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 referred to as symbiotic nodulation signals (Nod or Nod factors) or as Myc factors), consist of an oligosaccharide backbone of ß-l,4-linked /V-acetyl-D-glucosamine residues (“GlcNAc”) with an N-linked fatty acid side chain fused to the non-reducing end. As can be seen from the literature, LCOs differ in the number of GlcNAc units in the backbone structure, in the length and degree of saturation of the fatty acid chain and 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 - purin-6-amine, 2-chloro-N-(3-methoxyphenyl)-9H-purin-6-amine.

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;

RA ¹ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, nitro or (C ₁ -C ₄ )-haloalkyl;

W _A is an unsubstituted or substituted divalent heterocyclic radical from the group of partially 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 RA 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 linked to the carbonyl group in (S1) via the N atom and is unsubstituted or substituted by radicals from the group (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-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, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkoxy or substituted or unsubstituted phenyl; R _A ⁵ is H, (C ₁ -C ₈ )alkyl, (C ₁ -C ₈ )haloalkyl, (C ₁ -C ₄ )alkoxy(C ₁ -C ₈ )alkyl, cyano or COOR _A ⁹ , wherein R _A ⁹ is hydrogen, (C ₁ -C ₈ )alkyl, (C ₁ -C ₈ )haloalkyl, (C ₁ -C ₄ )alkoxy(C ₁ -C ₄ )alkyl, (C ₁ -C ₆ )hydroxyalkyl, (C ₃ -C ₁₂ )cycloalkyl or tri(C ₁ -C ₄ )alkylsilyl; R _A ⁶ , R _A ⁷ , R _A ⁸ are identical or different and are hydrogen, (C ₁ -C ₈ )-alkyl, (C ₁ -C ₈ )-haloalkyl, (C 3 -C 12)-cycloalkyl or substituted or unsubstituted phenyl; RA ¹⁰ is H, (C 3 -C 12)-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-pyrazolin-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-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-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4) and related compounds 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 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S1-5), 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylic acid methyl ester (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 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylic acid ethyl ester (S 1-8) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S 1 - 10) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-11) ("Isoxadifen-ethyl") or -n-propyl ester (S1-12) or the 5-(4-Fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-13) as described in patent application WO-A-95/07897. f) Compounds of the triazolyloxyacetic acid derivative type (S1 ^f ), 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

S2) Quinoline derivatives of the formula (S2), where the symbols and indices have the following meanings:

R _B ¹ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, nitro or (C ₁ -C ₄ )-haloalkyl; n _B is a natural number from 0 to 5, preferably 0 to 3;

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 linked to the carbonyl group in (S2) via the N atom and is unsubstituted or substituted by radicals from the group (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy or optionally substituted phenyl, preferably a radical of the formula ORB ³ , NHRB ⁴ or N(CH ₃ ), in particular of the formula OR _B ³ ;

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

RB ⁴ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkoxy or substituted or unsubstituted phenyl;

TB is a (C ₁ or C ₂ )-alkanediyl chain which is unsubstituted or substituted with one or two

(C ₁ -C ₄ ) -alkyl radicals or with [(C ₁ -C ₃ )-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)-1-ethyl ester (S2-8), (5-chloro-8-quinolinoxy)acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds as described in EP-A-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 (5-chloro-8-quinolinoxy)malonic acid type (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:

R _c ¹ is (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₂ -C ₄ )-haloalkenyl, (C ₃ -C ₇ )-cycloalkyl, preferably dichloromethyl;

R _c ² , R _c ³ are identical or different and are hydrogen, (C ₁ -C ₄ )alkyl, (C ₂ -C ₄ )alkenyl, (C ₂ -C ₄ )alkynyl, (C ₁ - C ₄ )haloalkyl, (C ₂ -C ₄ )haloalkenyl, (C ₁ -C ₄ )alkylcarbamoyl-(C ₁ -C ₄ )alkyl, (C ₂ -C ₄ )alkenylcarbamoyl-(C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )alkoxy-(C ₁ -C ₄ )alkyl, dioxolanyl-(C ₁ -C ₄ )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 substances of the dichloroacetamide type, which are frequently used as pre-emergence safeners (soil-effective safeners), such as

"Dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-l,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-acylsulfonamides of formula (S4) and their salts, where the symbols and indices have the following meanings:

XD is CH or N;

R _D ¹ is CO-NR _D ⁵ RD ⁶ or NHCO-RD ⁷ ;

R _D ² is halogen, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-haloalkoxy, nitro, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ )-alkoxycarbonyl or (C ₁ -C ₄ )-alkylcarbonyl;

R _D ³ is hydrogen, (C ₁ -C ₄ )-alkyl, (C ₂ -C ₄ )-alkenyl or (C ₂ -C ₄ )-alkynyl;

R _D ⁴ is halogen, nitro, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-haloalkoxy, (C ₃ -C ₆ )-cycloalkyl, phenyl, (C ₁ -C ₄ )-alkoxy, cyano, (C ₁ -C ₄ )-alkylthio, (C ₁ -C ₄ )-alkylsulfinyl, (C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ )-alkoxycarbonyl or (C ₁ -C ₄ )-alkylcarbonyl;

R _D ⁵ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₅ -C ₆ )-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, (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy, (C ₁ -C ₂ )-alkylsulfinyl, (C ₁ -C ₂ )-alkylsulfonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₄ -alkoxycarbonyl, (C ₁ -C ₄ )-alkylcarbonyl and Phenyl and in the case of cyclic radicals also (C ₁ -C _{4 )} -alkyl and (C ₁ -C ₄ )-haloalkyl;

R _D ⁶ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl or (C ₂ -C ₆ )-alkynyl, where the last three radicals are substituted by VD radicals from the group halogen, hydroxy, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy and (C ₁ -C ₄ )-alkylthio, or

R _D ⁵ and R _D ⁶ together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;

R _D ⁷ is hydrogen, (C ₁ -C ₄ )-alkylamino, di-(C ₁ -C ₄ )-alkylamino, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, where the last 2 radicals are substituted by VD substituents from the group halogen, (C ₁ -C ₄ )- Alkyl and (C ₁ -C ₄ )-haloalkyl are substituted; 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, eg of the following formula (S4 ^a ), which are known, for example, from WO-A-97/45016 wherein R _D ⁷ is (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, the last 2 radicals being substituted by vD substituents from the group halogen, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy and (C ₁ -C ₄ )-alkylthio and in the case of cyclic radicals also (C ₁ -C ₄ )-alkyl and (C ₁ -C ₄ )-haloalkyl; R _D ⁴ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, CF ₃ ; m _D is 1 or 2; v _D is 0, 1, 2 or 3; and acylsulfamoylbenzoic acid amides, eg of the following formula (S4 ^b ), which are known eg from WO-A-99/16744, e.g. those in which R _D ⁵ = cyclopropyl and (R _D ⁴ ) = 2-OMe ("Cyprosulfamide", S4-1), RD ⁵ = cyclopropyl and (R _D ⁴ ) = 5-C1-2-OMe (S4-2), RD ⁵ = ethyl and ( _R D ⁴ ) = 2-OMe (S4-3), R _D ⁵ = isopropyl and (R _D ⁴ ) = 2-OMe is (S4-5). as well as compounds of the N-acylsulfamoylphenylurea type of formula (S4 ^c ), which are known, for example, from EP-A-365484, wherein R _D ⁸ and R _D ⁹ independently of one another are hydrogen, (C ₁ -C ₈ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₃ -C ₆ )-alkenyl, (C ₃ -C ₆ )-alkynyl, R _D ⁴ is halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )alkoxy, CF ₃ m _D 1 or 2; for example 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea. 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:

RE ¹ , RE ² are independently halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkylamino, di-(C ₁ -C ₄ )-alkylamino, nitro;

AE is COOR _E ³ or COSR _E ⁴

R _E ³ , R _E ⁴ are each independently hydrogen, (C ₁ -C ₄ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₄ )-alkynyl, cyanoalkyl, (C ₁ -C ₄ )-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium, n _E ¹ is 0 or 1 n _E ² , n _E ³ are each independently 0, 1 or 2, preferably diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1). S8) Compounds of the formula (S8) as described in WO-A-98/27049 wherein

X _F CH or N, n _F in case X _F =N, an integer from 0 to 4 and RF ¹ halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy, nitro, (C ₁ - C ₄ )-alkylthio, (C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ )-alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, R _F ² hydrogen or (C ₁ -C ₄ )-alkyl, RF ³ hydrogen, (C ₁ -C ₈ )-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy; or their salts, preferably compounds in which X _{is F} CH, n _F is an integer from 0 to 2, R _F ¹ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy, R _F ² is hydrogen or (C ₁ -C ₄ )-alkyl, R _F ³ is hydrogen, (C ₁ -C ₈ )-alkyl, (C ₂ -C ₄ )-alkenyl, (C ₂ -C ₄ )-alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy, or their salts. 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 in which R _G ¹ is halogen, (C ₁ -C ₄ )-alkyl, methoxy, nitro, cyano, CF ₃ , OCF ₃ Y _G , Z _G are independently O or S, n _{G is} an integer from 0 to 4, R _G ² is (C ₁ -C ₁₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₃ -C ₆ )-cycloalkyl, aryl; benzyl, halobenzyl, R _G ³ is hydrogen or (C ₁ -C ₆ )-alkyl. S11) Active ingredients of the oxyimino compound type (S11), which are known as seed dressers, such as. E.g., "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is 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), which is known as a seed dressing safener for millet against metolachlor damage, and "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is 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), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice, "Flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is 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 phosphorodithioate) (S13-7), "Dietholate" (O,O-Diethyl-O-phenylphosphorothioate) (S13-8), "Mephenate" (4-chlorophenyl methylcarbamate) (S13-9).

S14) Active substances which, in addition to a herbicidal effect against harmful plants, also have a safener effect on cultivated plants such as rice, such as

"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-methoxy-benzophenone), 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.

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

R _H ¹ represents a (C ₁ -C ₆ )-haloalkyl radical and

R _H ² is hydrogen or halogen and R _H ³ , _H ⁴ independently of one another are hydrogen, (C ₁ -C ₁₆ )-alkyl, (C ₂ -C ₁₆ )-alkenyl or (C ₂ -C ₁₆ )-alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy, (C ₁ -C ₄ )-alkylthio, (Ci-C4)-alkylamino, di[(C ₁ -C ₄ )-alkyl]-amino, [(C ₁ -C ₄ )-alkoxy]-carbonyl, [(C ₁ -C ₄ )haloalkoxy]-carbonyl, (C ₃ -C ₆ )-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or (C ₃ - C ₆ )-cycloalkyl, (C ₄ -C ₆ )-cycloalkenyl, (C ₃ -C ₆ )-cycloalkyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C ₄ -C ₆ )-cycloalkenyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy, (C ₁ -C ₄ )-alkylthio, (C ₁ -C ₄ )-alkylamino, di[(C ₁ -C ₄ )-alkyl]-amino, [(C ₁ -C ₄ )-alkoxy]-carbonyl, [(C ₁ -C ₄ )-haloalkoxy]-carbonyl, (C ₃ -C ₆ )-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, is substituted, or

R _H ³ is (C ₁ -C ₄ )-alkoxy, (C ₂ -C ₄ )-alkenyloxy, (C ₂ -C ₆ )-alkynyloxy or (C ₂ -C ₄ )-haloalkoxy and

R _H ⁴ is hydrogen or (C ₁ -C ₄ )-alkyl, or

R _H ³ and R _H ⁴ together with the directly bonded N atom form 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-C ₄ alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy and (C ₁ -C ₄ )-alkylthio.

S16) Active substances which are primarily used as herbicides, but also have a safener effect on cultivated plants, e.g. (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), l-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl). Biological examples:

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

Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants were placed in plastic or wood fiber pots in sandy loam soil, covered with soil and grown in the greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated in the single leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then sprayed onto the green parts of the plant as an aqueous suspension or emulsion with the addition of 0.5% additive at a water application rate of the equivalent of 600 l/ha. After the test plants had been in the greenhouse for around 3 weeks under optimal growth conditions, the effect of the preparations was visually assessed in comparison with untreated controls. For example, 100% effect = plants have died, 0% effect = like control plants.

Tables A1 to A13 below 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.

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

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 %

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 %

Table A3c: Post-emergence effect at 20g/ha against AMARE in % Table A4a: Post-emergence effect 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 %

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

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

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 %

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

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

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 % The following tables A14 to A17 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, which were observed in tests according to the test procedure mentioned above. 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 %

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

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 weeds such as, for example, sedum, sedum, sedum, thrush ... 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 or less of active substance per hectare, and (b) good crop tolerance with organisms such as Oryza sativa (ORYSA), Zea mays (ZEAMX), Glycine max (GLXMA) and Triticum aestivum (TRZAS) at an application rate of 0.02 kg or 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”) after post-emergence. Tables B1-B5 below show the effects of compounds according to the invention (I.7-12, I.7-14, I.7-16), which were obtained according to the above-mentioned test procedure, on various weeds at an application rate corresponding to 20 g/ha and lower in comparison to known from the literature and structurally similar to the compound (“a-27”, “a-29”, disclosed in W02002/098227).

The tested compounds according to the invention (1.7-12, 1.7-14, 1.7-16) differ from the compounds known from the literature by variance of a significant structural feature with regard to the ester unit while the “cycloalkyl group” remains the same through the incorporation of a methylene bridge (-CH2-).

Table Bl

Table B2

Table B3 Table B4

Table B5 As the results shown in Tables Bl 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 harmful plants such as Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Avena fatura (AVEFA) and Veronica persica (VERPE) at an application rate of 20 g and less per hectare, compared with the structurally similar compounds known from the literature “a-27”, “a-29”, (WO2002/098227), or a structure generically included in the same. 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 with structurally similar compounds known from the literature ("a-27", "a-29", disclosed in W02002/098227).

Table B6

Table B7

Table B8

Table B9

Table BIO

As the results shown 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 included in the same, 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

Patent claims: 1. Substituted N-phenyluracils of the general formula (I) or salts thereof in which R1 is hydrogen, halogen, cyano, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-alkoxy or (C1-C8)-haloalkoxy, R2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C1-C8)-alkoxy, R3 is hydrogen, halogen or (C1-C8)-alkoxy, R4 is halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C8)-haloalkyl or (C2-C8)-alkynyl, R5, R6 and R7 independently of one another are hydrogen, halogen, cyano, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-alkoxy or (C1-C8)-haloalkoxy, G is unbranched or branched (C1-C8)-alkylene, Q is a radical of the formula, R8 is hydrogen, (C1-C8)-alkyl or cyano, R9 is hydrogen or (C1-C8)-alkyl, R10 is (C3-C8)-cycloalkyl, which is unsubstituted or each independently substituted 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 is spiro-(C5-C9)-alkanyl or dispiro-(C7-C8)-alkanyl, which is 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 independently of one another are O (oxygen) or S (sulfur). 2. Compounds of the general formula (I) according to claim 1 and/or their salt, characterized in that R1 is hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy or (C1-C6)-haloalkoxy, R2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C1-C6)-alkoxy, R3 is hydrogen, halogen or (C1-C6)-alkoxy, R4 is halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C6)-haloalkyl or (C2-C6)-alkynyl, R5, R6 and R7 independently of one another are hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy or (C1-C6)-haloalkoxy G is unbranched or branched (C1-C6)-alkylene, Q is a radical of the formula, R8 is hydrogen, (C1-C6)-alkyl or cyano, R9 is hydrogen or (C1-C6)-alkyl, R10 is (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 is 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 is 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 their salt, characterized in that R1 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1,1,2-Trimethylpropyl, 1,2,2-Trimethylpropyl, 1-Ethyl-1-methylpropyl, 1-Ethyl-2-methylpropyl, Trifluoromethyl, Difluoromethyl, Pentafluoroethyl, 2,2-Difluoro- ethyl, 2,2,2-Trifluoroethyl, Methoxy, Ethoxy, Prop-1-yloxy, Prop-2-yloxy, But-1-yloxy, But-2-yloxy, 2-Methylprop-1-yloxy, 1,1-Dimethyleth-1-yloxy, Difluoromethoxy, Trifluoromethoxy, Pentafluoroethoxy, 2,2-Difluoroethoxy, 2,2,2-Trifluoroethoxy, R2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, prop-1-yloxy, but-1-yloxy, R3 is hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, prop-1-yloxy, Prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, R4 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, R5, R6 and R7 independently represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop- 1-yl, 1-methylethyl, but- 1-yl, 1-methylpropyl, 2-methylpropyl, 1.1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1.1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1.2-Dimethylbutyl, 1,3-Dimethylbutyl, 2,2-Dimethylbutyl, 2,3-dimethylbutyl, 3.3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1,1,2-Trimethylpropyl, 1,2,2-Tri- methylpropyl, 1 -Ethyl- 1 -methylpropyl, l-Ethyl-2-methylpropyl, Trifluoromethyl, Difluoromethyl, Pentafluoroethyl, 2,2-Difluoroethyl, 2,2,2-Trifluoroethyl, Methoxy, Ethoxy, Prop-l-yloxy, Prop-2-yloxy, But-l-yloxy, But-2-yloxy, 2-Methylprop-l-yloxy, 1.1-Dimethyleth-l-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2.2-difluoroethoxy, 2,2,2-trifluoroethoxy, G for methylene, (methyl)methylene, (ethyl)methylene, (prop-l-yl)methylene, (prop-2- yl)methylene, (but-l-yl)methylene, (but-2-yl)methylene, (pent-l-yl)methylene, (pent-2- yl)methylene, (pent-3-yl)methylene, (dimethyl)methylene, (diethyl)methylene, ethylene, n-propylene, (l-methyl)ethyl-l-ene, (2-methyl)ethyl-l-ene, n-butylene, 1-methylpropyl- 1 -ene, 2-Methylpropyl- 1 -ene, 3-Methylpropyl-l-ene, 1,1 -Dimethylethyl- 1 -ene, 2,2-Dimethylethyl- 1-ene, 1 -Ethylethyl- 1 -ene, 2-Ethylethyl-l-ene, l-(Prop-l-yl)ethyl-l-ene, 2-(Prop-l-yl)ethyl- 1-ene, l-(Prop-2-yl)ethyl-l-ene, 2-(Prop-2-yl)ethyl-l-ene, 1,1,2-Trimethylethyl-l-ene, 1.2.2-Trimethylethyl-l-ene, 1,1,2,2-Tetramethylethyl-l-ene, n-Pentylene, 1-Methylbutyl-1-ene, 2-Methylbutyl-1-ene, 3-Methylbutyl-1-ene, 4-Methylbutyl-l-ene, 1,1-Dimethylpropyl- 1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl-l-ene, 1,2-dimethylpropyl-l-ene, 1.3-Dimethylpropyl-l-ene, 1-Ethylpropyl- 1 -ene, n-Hexylene, 1-Methylpentyl- 1 -ene, 2-Methylpentyl- 1 -ene, 3-Methylpentyl- 1 -ene, 4-Methylpentyl- 1 -ene, 1,1 -Dimethylbutyl- 1- ene, 1,2-Dimethylbutyl-l-ene, 1,3-Di-methylbutyl-l-ene, 2,2-Dimethylbutyl- 1 -ene, 2,3-Dimethylbutyl- 1 -ene, 3,3-Dimethylbutyl-l-ene, 1 -Ethylbutyl- 1 -ene, 2-Ethylbutyl- 1 -ene, 1.1.2-Trimethylpropyl- 1 -ene, 1 ,2,2-Trimethylpropyl- 1 -ene, 1 -Ethyl- 1 -methylpropyl- 1 -ene, 1 -Ethyl-2-methylpropyl- 1 -ene, X and Y independently represent O (oxygen) or S (sulfur) and Q represents one of the following specifically named groups Q1 to Q-25, whereby 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 the 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 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 ⁷ independently 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-1-ene, 2-methylpropyl-l-ene, 3-methylpropyl-l-ene, 1,1-dimethylethyl-1-ene, 2,2-dimethylethyl-l-ene, 1-ethylethyl-1-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, 2-methylbutyl-l-ene, 3-methylbutyl-l-ene, 4-methylbutyl-l-ene, 1,1-dimethylpropyl-l-ene, 2,2-dimethylpropyl-l-ene, 3,3-dimethylpropyl-l-ene, 1,2-dimethylpropyl-l-ene, 1,3-dimethylpropyl-l-ene, 1-ethylpropyl-1-ene 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 in claim 3. Compounds of the general formula (I) according to claim 1 and/or their salt, characterized in that R ¹ represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, R ² is fluorine, R ³ is fluorine, R ⁴ is chlorine, bromine, cyano, NO ₂ , C(O)NH ₂ or C(S)NH ₂ , R ⁵ , R ⁶ and R ⁷ independently of one another are hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, n-pentylene or n-hexylene, X and Y independently of one another are O (oxygen) or S (sulfur) and Q is one of the groups Q-1 to Q-2 specifically mentioned in claim 3. Q-25. 6. Compounds of the general formula (I) according to claim 1 and/or their salt, characterized in that R ¹ is hydrogen, fluorine, chlorine or bromine, R ² is fluorine, R ³ is fluorine, R ⁴ is chlorine, bromine, cyano or NO ₂ , R ⁵ is hydrogen, fluorine, chlorine or bromine, R ⁶ is hydrogen, fluorine, chlorine, bromine or cyano, R ⁷ is hydrogen, fluorine, chlorine or bromine, G is methylene, (methyl)methylene or (ethyl)methylene, X and Y independently of one another are 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 is fluorine, R ³ is fluorine, R ⁴ stands for chlorine, bromine, cyano or NO ₂ , R ⁵ stands for hydrogen, R ⁶ stands 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 is fluorine, R ³ stands for fluorine, R ⁴ stands for chlorine, bromine or cyano, R ⁵ stands for hydrogen, R ⁶ stands for hydrogen or fluorine, R ⁷ stands 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 also 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 aids 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 defined in one of the Claims 1 to 8 defined and/or their salts, 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.