Substituted n-phenylurea pyrimidines and salts thereof and use thereof as herbicidally active substances

Abstract

The present invention relates to substituted N-phenylurea pyrimidines of general formula (I) or salts thereof (formula I), in which the groups in general formula (I) are as defined in the description, and to the use thereof as herbicides, in particular for controlling weeds and / or grassy weeds in crops, and / or as plant growth regulators for influencing the growth of crops. # imgabs0 #

Description

[0001] The present invention relates to the technical field of crop protection products, in particular to the technical field of herbicides for selectively controlling broadleaf weeds and grass weeds in crops of useful plants.

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

[0003] Crop protection products for selectively controlling harmful plants in crops of useful plants or active ingredients for controlling unwanted plants known to date sometimes have disadvantages in their use, whether (a) they have insufficient herbicidal activity (if any) against specific harmful plants, (b) the spectrum of harmful plants that can be controlled with the active ingredients is not wide enough, (c) their selectivity for crops of useful plants is too low and / or (d) they have toxicologically unfavorable properties. In addition, some active ingredients that can be used as plant growth regulators for many useful plants cause undesirable reductions in harvest yields in other useful plants, or are compatible with crop plants only within a narrow application rate range (if any). Due to the difficulty in obtaining precursors and reagents, some known active ingredients cannot be prepared economically on an industrial scale, or they have only insufficient chemical stability. In the case of other active ingredients, the activity is too highly dependent on environmental conditions, such as weather and soil conditions.

[0004] The herbicidal action of these known compounds, in particular at low application rates, and / or their compatibility with crop plants still needs to be improved.

[0005] It is known from various documents that specifically substituted N-aryl uracils can be used as active herbicidal ingredients (see 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 aryl uracils have many activity gaps, especially against monocotyledonous weeds. Many combinations of active herbicidal ingredients based on N-aryl uracils are also known (see DE 4437197, EP 714602, WO 96 / 07323, WO 96 / 08151, JP 11189506, JP 2003 / 104808, JP 2003 / 104809, JP 2003 / 104810, JP 2003 / 160415 and JP 2003 / 160416). However, the performance of these active ingredient combinations is not completely satisfactory.

[0006] Also known are substituted uracils with N-bonded and further substituted diaryl ether groups or corresponding heteroaryl aryl ether groups (see US6333296, US6121201, WO2001 / 85907, EP1122244, EP1397958, EP1422227, WO 2002 / 098227). In addition, highly substituted N-phenyluracils with specifically substituted carbonyl alkoxy groups have been described (see WO2011 / 137088). WO2018 / 019842 describes the use of specifically substituted N-phenyluracils for controlling specific dicotyledonous weeds that are particularly resistant to established herbicides. Substituted 3-phenyl-5-alkyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (see WO2019 / 101551) is also known.

[0007] Surprisingly, it has now been found that selected N-phenyluracils or salts thereof having substituted alkyl ester side chains are suitable as herbicides and can be used particularly advantageously for controlling monocotyledonous and dicotyledonous weeds in crop plant cultivation.

[0008] Therefore, the present invention provides a substituted N-phenyluracil or a salt thereof of the general formula (I)

[0009]

[0010] in

[0011] 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,

[0012] R 2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C 1 -C 8 )-alkoxy,

[0013] R 3 is hydrogen, halogen or (C 1 -C 8 )-alkoxy,

[0014] R 4 Halogen, cyano, NO 2 、C(O)NH 2 、C(S)NH 2 , (C 1 -C 8 )-haloalkyl or (C 2 -C 8 )-alkynyl,

[0015] R 5 , R 6 and R 7 are independently hydrogen, halogen, cyano, (C 1 -C 8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 1 -C 8 )-alkoxy or (C 1 -C 8 )-haloalkoxy,

[0016] G is a straight chain or branched chain (C1 -C 8 )-alkylene,

[0017] Q is a group of the formula

[0018]

[0019] R 8 For hydrogen, (C 1 -C 8 )-alkyl or cyano,

[0020] R 9 is hydrogen or (C 1 -C 8 )-alkyl,

[0021] R 10 For (C 3 -C 8 )-cycloalkyl, which is unsubstituted or substituted independently in each case by "m" groups 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

[0022] For spiral-(C 5 -C 9 )-alkyl or dispiro-(C 7 -C 8 )-alkyl, which is unsubstituted or substituted independently in each case by "m" groups 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,

[0023] m is 0, 1, 2 or 3,

[0024] and

[0025] X and Y are independently O (oxygen) or S (sulfur).

[0026] The present invention more preferably provides a compound of general formula (I), wherein

[0027] 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,

[0028] R 2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl or (C 1 -C 6 )-alkoxy,

[0029] R 3 is hydrogen, halogen or (C 1 -C 6 )-alkoxy,

[0030] R 4 Halogen, cyano, NO 2 、C(O)NH 2 、C(S)NH 2 , (C 1 -C 6 )-haloalkyl or (C 2 -C 6 )-alkynyl,

[0031] R 5 , R 6 and R 7 are independently hydrogen, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy or (C 1 -C 6 )-haloalkoxy,

[0032] G is a straight chain or branched chain (C 1 -C 6 )-alkylene,

[0033] Q is a group of the formula

[0034]

[0035] R 8 For hydrogen, (C 1 -C 6 )-alkyl or cyano,

[0036] R 9 is hydrogen or (C 1 -C 6 )-alkyl,

[0037] R 10 For (C 3 -C 7 )-cycloalkyl, which is unsubstituted or substituted independently in each case by "m" groups 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

[0038] For spiral-(C 5 -C 7 )-alkyl or dispiro-(C 7 -C 8 )-alkyl, which is unsubstituted or substituted independently in each case by "m" groups selected from the group consisting of halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy,

[0039] m is 0, 1, 2, or 3,

[0040] and

[0041] X and Y are independently O (oxygen) or S (sulfur).

[0042] The present invention very particularly preferably provides compounds of the general formula (I) in which

[0043] R 1is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, propan-1-yl, 1-methylethyl, butan-1-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3 -dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,

[0044] R 2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, propan-1-yloxy, but-1-yloxy,

[0045] R 3 is hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, propan-1-yloxy, propan-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylpropan-1-yloxy, 1,1-dimethyleth-1-yloxy,

[0046] R 4 Fluorine, chlorine, bromine, cyano, NO 2 、C(O)NH 2 、C(S)NH 2 , trifluoromethyl, difluoromethyl, pentafluoroethyl, ethynyl, propyn-1-yl, 1-butyn-1-yl, pentyn-1-yl, hexyn-1-yl,

[0047] R 5 , R 6 and R 7and 1-ethylpropyl, 1-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,

[0048] G is methylene, (methyl)methylene, (ethyl)methylene, (prop-1-yl)methylene, (prop-2-yl)methylene, (but-1-yl)methylene, (but-2-yl)methylene, (pent-1-yl)methylene, (pent-2-yl)methylene, (pent-3-yl)methylene, (dimethyl)methylene, (diethyl)methylene, ethylene, n-propylene, (1-methyl)eth-1-ylidene, (2-methyl)eth-1-ylidene, n-butylene, 1-methylprop-1-ylidene, 2-methylprop-1-ylidene, -ylidene, 3-methylpropan-1-ylidene, 1,1-dimethylethane-1-ylidene, 2,2-dimethylethane-1-ylidene, 1-ethylethane-1-ylidene, 2-ethylethane-1-ylidene, 1-(propan-1-yl)ethane-1-ylidene, 2-(propan-1-yl)ethane-1-ylidene, 1-(propan-2-yl)ethane-1-ylidene, 2-(propan-2-yl)ethane-1-ylidene, 1,1,2-trimethylethane-1-ylidene, 1,2,2-trimethylethane-1-ylidene, 1,1,2,2-tetramethylethane-1-ylidene. 1-methylbutylene, 2-methylbutylene, 3-methylbutylene, 4-methylbutylene, 1,1-dimethylpropylene, 2,2-dimethylpropylene, 3,3-dimethylpropylene, 1,2-dimethylpropylene, 1,3-dimethylpropylene, 1-ethylpropylene, n-hexylene, 1-methylpentylene, 2-methylpentylene, 3-methylpentylene, 4-methylpentylene -1-ylidene, 1,1-dimethylbutan-1-ylidene, 1,2-dimethylbutan-1-ylidene, 1,3-dimethylbutan-1-ylidene, 2,2-dimethylbutan-1-ylidene, 2,3-dimethylbutan-1-ylidene, 3,3-dimethylbutan-1-ylidene, 1-ethylbutan-1-ylidene, 2-ethylbutan-1-ylidene, 1,1,2-trimethylpropan-1-ylidene, 1,2,2-trimethylpropan-1-ylidene, 1-ethyl-1-methylpropan-1-ylidene, 1-ethyl-2-methylpropan-1-ylidene,

[0049] X and Y are independently O (oxygen) or S (sulfur),

[0050] and

[0051] Q is one of the parts Q-1 to Q-25 mentioned explicitly below, wherein the structure of the following table

[0052] The arrows in the formula represent the bonds from each Q group to the carbonyl group in the general formula (I),

[0053]

[0054] The present invention particularly preferably provides compounds of the general formula (I), wherein

[0055] R1 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy,

[0056] R 2 is hydrogen, fluorine or chlorine,

[0057] R 3 is hydrogen, fluorine, chlorine, bromine or methoxy,

[0058] R 4 Fluorine, chlorine, bromine, cyano, NO 2 、C(O)NH 2 、C(S)NH 2 , trifluoromethyl, ethynyl or propyn-1-yl,

[0059] R 5 , R 6 and R 7 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy,

[0060] G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethane-1-ylidene, (2-methyl)ethane-1-ylidene, n-butylene, 1-methylprop-1-ylidene, 2-methylprop-1-ylidene, 3-methylprop-1-ylidene, 1,1-dimethylethane-1-ylidene, 2,2-dimethylethane-1-ylidene, 1-ethylethane-1-ylidene, 2-ethylethane-1-ylidene, 1-(prop-1-yl)ethane-1-ylidene, 2-(prop-1-yl)ethane-1-ylidene, -yl)ethane-1-ylidene, 1-(prop-2-yl)ethane-1-ylidene, 2-(prop-2-yl)ethane-1-ylidene, n-pentylene, 1-methylbutan-1-ylidene, 2-methylbutan-1-ylidene, 3-methylbutan-1-ylidene, 4-methylbutan-1-ylidene, 1,1-dimethylpropan-1-ylidene, 2,2-dimethylpropan-1-ylidene, 3,3-dimethylpropan-1-ylidene, 1,2-dimethylpropan-1-ylidene, 1,3-dimethylpropan-1-ylidene, 1-ethylpropan-1-ylidene or n-hexylene,

[0061] X and Y are independently O (oxygen) or S (sulfur),

[0062] and

[0063] Q is one of the moieties Q-1 to Q-25 explicitly mentioned above.

[0064] The present invention very particularly preferably provides compounds of the general formula (I) in which

[0065] R 1is hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy,

[0066] R 2 For fluorine,

[0067] R 3 For fluorine,

[0068] R 4 For chlorine, bromine, cyano, NO 2 、C(O)NH 2 or C(S)NH 2 ,

[0069] R 5 , R 6 and R 7 are independently hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy,

[0070] G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)eth-1-ylidene, (2-methyl)eth-1-ylidene, n-butylene, 1-methylprop-1-ylidene, 2-methylprop-1-ylidene, 3-methylprop-1-ylidene, n-pentylene or n-hexylene,

[0071] X and Y are independently O (oxygen) or S (sulfur),

[0072] and

[0073] Q is one of the moieties Q-1 to Q-25 explicitly mentioned above.

[0074] The present invention particularly preferably provides compounds of the general formula (I), wherein

[0075] R 1 is hydrogen, fluorine, chlorine or bromine,

[0076] R 2 For fluorine,

[0077] R 3 For fluorine,

[0078] R 4 Chloro, bromo, cyano or NO 2 ,

[0079] R 5 is hydrogen, fluorine, chlorine or bromine,

[0080] R 6 is hydrogen, fluorine, chlorine, bromine or cyano,

[0081] R 7 is hydrogen, fluorine, chlorine or bromine,

[0082] G is methylene, (methyl)methylene or (ethyl)methylene,

[0083] X and Y are independently O (oxygen) or S (sulfur),

[0084] and

[0085] Q is one of the moieties Q-1 to Q-25 explicitly mentioned above.

[0086] The present invention very particularly preferably provides compounds of the general formula (I) in which

[0087] R 1 For hydrogen,

[0088] R 2 For fluorine,

[0089] R 3 For fluorine,

[0090] R 4 Chloro, bromo, cyano or NO 2 ,

[0091] R 5 For hydrogen,

[0092] R 6 is hydrogen, fluorine, chlorine, bromine or cyano,

[0093] R 7 For hydrogen,

[0094] G is methylene or (methyl)methylene,

[0095] X is O (oxygen) or S (sulfur),

[0096] Y is O (oxygen),

[0097] and

[0098] Q is one of the moieties Q-1 to Q-25 explicitly mentioned above.

[0099] The present invention very particularly preferably provides compounds of the general formula (I) in which

[0100] R 1 For hydrogen,

[0101] R 2 For fluorine,

[0102] R 3 For fluorine,

[0103] R 4 Chloro, bromo, cyano or NO 2 ,

[0104] R5 is hydrogen,

[0105] R 6 is hydrogen, fluorine, chlorine,

[0106] R 7 is hydrogen,

[0107] G is methylene, (methyl)methylene,

[0108] X is O (oxygen) or S (sulfur),

[0109] Y is O (oxygen),

[0110] and

[0111] Q is one of the parts Q-1 to Q-25 specifically mentioned above.

[0112] The present invention extremely particularly preferably provides a compound of general formula (I), wherein

[0113] R 1 is hydrogen,

[0114] R 2 is fluorine,

[0115] R 3 is fluorine,

[0116] R 4 is chlorine, bromine or cyano,

[0117] R 5 is hydrogen,

[0118] R 6 is hydrogen or fluorine,

[0119] R 7 is hydrogen,

[0120] G is methylene,

[0121] X is O (oxygen),

[0122] Y is O (oxygen),

[0123] and

[0124] Q represents one of the parts 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 above.

[0125] The definitions of the above general or preferred groups apply both to the final products of general formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These group definitions can be combined with one another as required, i.e., including combinations between the given preferred ranges.

[0126] The compounds of the general formula (I) according to the invention or their salts or their use according to the invention are of particular importance firstly because of higher herbicidal activity, better selectivity and / or better preparability, in which the individual radicals have one of the preferred meanings specified or indicated below or in particular in which one or more preferred meanings specified or indicated below occur in combination.

[0127] If a compound can form tautomers whose structures are not formally covered by the general formula (I) by hydrogen displacement, these tautomers are still covered by the definition of the compounds of the general formula (I) according to the present invention, unless specific tautomers are considered. For example, many carbonyl compounds can exist in the keto form and in the enol form, both of which are covered by the definition of the compounds of the general formula (I).

[0128] Depending on the nature of the substituents and their connection mode, the compounds of general formula (I) can exist in the form of stereoisomers. Possible stereoisomers defined by their specific three-dimensional form, such as enantiomers, diastereomers, Z and E isomers, are all covered by general formula (I). For example, if there are one or more alkenyl groups, diastereomers (Z and E isomers) can be produced. For example, if there are one or more asymmetric carbon atoms, enantiomers and diastereomers can be produced. Stereoisomers can be obtained from the mixture obtained in the preparation process by conventional separation methods. Analytical grade chromatographic separation can be performed to find enantiomeric excess or diastereomeric excess, or preparative grade chromatographic separation can be performed to prepare test samples for biological testing. Stereoisomers can also be selectively prepared by using optically active raw materials and / or auxiliary agents to carry out stereoselective reactions. Therefore, the present invention also relates to all stereoisomers and mixtures thereof that are covered by general formula (I) but not shown in their specific stereoisomer form.

[0129] If the compounds are obtained in solid form, they can also be purified by recrystallization or leaching. If individual compounds (I) cannot be obtained in a satisfactory manner via the routes described below, they can be prepared by derivatization of other compounds (I).

[0130] Suitable separation methods, purification methods and methods for separating the stereoisomers of the compounds of the general formula (I) are the methods generally known to the person skilled in the art from analogous situations, for example by physical methods such as crystallization, chromatography (in particular column chromatography and HPLC (high pressure liquid chromatography)), distillation (optionally under reduced pressure), extraction and other methods, any residual mixtures can generally be separated by chromatography, for example on a chiral solid phase. Suitable methods for preparative quantities or on an industrial scale are, for example, crystallization methods, for example the crystallization of diastereomeric salts, which can be obtained from diastereomeric mixtures using optically active acids and, if appropriate, optically active bases (provided that acidic groups are present).

[0131] With respect to the compounds of the present invention, the terms used above and further used below will be explained. These terms are well known to those skilled in the art and have in particular the definitions explained below:

[0132] Unless defined differently, the names of chemical groups are generally to be understood so that the connection to the backbone or the remainder of the molecule is via the last-mentioned structural element of the relevant chemical group, i.e., for example in (C 1 -C 6 )-alkenyloxy is linked 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, the bond is in each case via a carbon atom of the alkyl group.

[0133] According to the present invention, "alkylthio" - alone or as part of a chemical group - refers to a linear or branched S-alkyl group preferably having 1 to 8 or 1 to 6 carbon atoms, for example (C 1 -C 10 )-alkylthio, (C 1 -C 6 )-alkylthio or (C 1 -C 4 )-alkylthio, such as (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-methylbutylthio, -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.

[0134] "Alkoxy" refers to an alkyl group bonded through an oxygen atom, for example (but not limited to) (C 1 -C 6 )-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy. Alkenyloxy represents an alkenyl group attached via an oxygen atom, and alkynyloxy represents an alkynyl group attached via an oxygen atom, for example (C 2 -C 10 )-alkenyloxy, (C 2 -C 6 )-alkenyloxy or (C 2 -C 4 )-alkenyloxy, and (C 3 -C 10 )-alkynyloxy, (C 3 -C 6 )-alkynyloxy or (C 3 -C 4 )-alkynyloxy.

[0135] According to the present invention, unless otherwise defined differently, "alkylcarbonyl" (alkyl-C(=O)-) represents an alkyl group bonded to the backbone through -C(=O)-, such as (C 1 -C 10 )-alkylcarbonyl, (C 1 -C 6 )-alkylcarbonyl or (C 1 -C 4 )-alkylcarbonyl. Here, the number of carbon atoms refers to the alkyl group in the alkylcarbonyl.

[0136] Unless otherwise defined differently, "alkoxycarbonyl (alkyl-O-C(=O)-)" represents: an alkyl group bonded to the backbone through -O-C(=O)-, such as (C 1 -C 10 )-alkoxycarbonyl, (C 1 -C 6 )-alkoxycarbonyl or (C 1 -C 4 )-alkoxycarbonyl. Here, the number of carbon atoms refers to the alkyl group in the alkoxycarbonyl. Similarly, according to the present invention, unless otherwise defined differently, "alkenyloxycarbonyl" and "alkynyloxycarbonyl" are an alkenyl group and an alkynyl group bonded to the backbone through -O-C(=O)-, respectively, such as (C 2 -C 10 )-alkenyloxycarbonyl, (C 2 -C 6 )-alkenyloxycarbonyl or (C 2 -C 4 )-alkenyloxycarbonyl, and (C 3 -C 10 )-alkynyloxycarbonyl, (C 3 -C 6 )-alkynyloxycarbonyl or (C 3 -C 4 )-alkynyloxycarbonyl. Here, the number of carbon atoms refers to the alkenyl group or alkynyl group in the alkenyloxycarbonyl or alkynyloxycarbonyl.

[0137] According to the present invention, unless otherwise defined differently, the term "alkylcarbonyloxy" (alkyl-C(=O)-O-) represents an alkyl group bonded to the backbone through the oxygen of the carbonyloxy (-C(=O)-O-), such as (C 1 -C 10 )-alkylcarbonyloxy, (C 1 -C 6 )-alkylcarbonyloxy or (C 1 -C 4 )-alkylcarbonyloxy. Here, the number of carbon atoms refers to the alkyl group in the alkylcarbonyloxy.

[0138] In the simplified form such as C(O)R 13 、C(O)OR 13 、OC(O)NR 11 R 12 or C(O)NR 11 R 12 In the formula, for example, O shown in brackets is an oxygen atom bonded to an adjacent carbon atom via a double bond.

[0139] In the simplified form such as OC(S)OR 13 、OC(S)SR 14 、OC(S)NR 11 R 12 In the simplified formula S shown in brackets, it is a sulfur atom bonded to the adjacent carbon atom through a double bond.

[0140] The term "aryl" denotes an optionally substituted monocyclic, bicyclic or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10, ring carbon atoms, for example phenyl, naphthyl, anthracenyl, phenanthryl, etc., preferably phenyl.

[0141] The term "optionally substituted aryl" also includes polycyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenyl, wherein the bonding site is located on the aromatic system. In systematic terms, "aryl" is also generally encompassed by the term "optionally substituted phenyl". Preferred aryl substituents herein 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, cycloalkyloxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, dialkylaminoalkoxy, tri[alkyl]silyl, di[alkyl]arylsilyl, di[alkyl] [alkyl] silyl, tri[alkyl] silylalkynyl, arylalkynyl, heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, dialkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, dialkylaminocarbonyl, heteroarylalkoxy, arylalkoxy.

[0142] Heterocyclic groups (heterocyclyl) contain at least one heterocycle (= carbocycle in which at least one carbon atom is replaced by a heteroatom, preferably by a heteroatom selected from N, O, S, P), which is saturated, unsaturated, partially saturated or heteroaromatic, and may be unsubstituted or substituted, in which case the bonding site is located on a ring atom. If a heterocyclyl group or a heterocycle is optionally substituted, it may be fused to other carbocycles or heterocycles. In the case of optionally substituted heterocyclyls, polycyclic systems are also included, such as 8-azabicyclo [3.2.1] octyl, 8-azabicyclo [2.2.2] octyl or 1-azabicyclo [2.2.1] heptyl. In the case of optionally substituted heterocyclyls, spirocyclic systems are also included, such as 1-oxa-5-azaspiro [2.3] hexyl. Unless defined differently, the heterocycle preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and contains one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocycle, which are preferably selected from N, O and S, but two oxygen atoms should not be directly adjacent, for example with one heteroatom selected from N, O and S: 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3-dihydro-1H-pyrrol-1- or 2- or 3- or 4- or 5-yl, 2, 5-dihydro-1H-pyrrol-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl, 2,3,4,5-tetrahydropyridine-2- or 3- or 4- or 5- or 6-yl, 1,2,3,6-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,2,3,4-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,4-dihydropyridine-1- or 2- or 3- or 4-yl, 2,3-dihydropyridine-2- or 3- or 4- or 5- or 6-yl, 2,5 -dihydropyridine-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl, 2,3,4,5-tetrahydro-1H-azepin-1- or 2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydro-1H-azepin-1- or 2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-tetrahydro-1H-azepin-1- or 2- or 3- or 4- 4,5,6-tetrahydro-2H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl, 4,5-dihydro-1H-azepine-1- or 2- or 3- or 4-yl, 2,5-dihydro-1H-azepine-1- or -2- or 3- or 4- or 5- or 6- or 7-yl, 2,7-dihydro-1H-azepine-1- or -2- or 3- or 4-yl, 2,3-dihydro-1H-azepine-1- or -2- or 3- or 4- or 5- or 6- or 7-yl, 3,4-dihydro-2H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl, 3,6-dihydro-2H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl, 5,6-dihydro-2H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl, 4,5-dihydro-3H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl, 1H-azepine-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-azepine-2- or 3- or 4- or 5- or 6- or 7-yl, 4H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2- or 3-oxolanyl (=2- or 3-tetrahydrofuranyl), 2,3-dihydrofuran-2- or 3- or 4- or 5-yl, 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (=2- or 3- or 4-tetrahydropyranyl), 3,4-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl, 3,6- dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl, 2H-pyran-2- or 3- or 4- or 5- or 6-yl, 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl, 2,3,4,5-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-tetrahydrooxepin-2- or 3- or 4-yl, 2,3-dihydrooxepin cycloheptatrien-2- or 3- or 4- or 5- or 6- or 7-yl, 4,5-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-tetrahydrothiophene, 2,3-dihydrothiophene-2- or 3- or 4- or 5-yl, 2,5-dihydrothiophene-2- or 3-yl, tetrahydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl, 2H-thiopyran-2- or 3- or 4- or 5- or 6-yl, 4H-thiopyran-2- or 3- or 4-yl. Preferred 3- and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxetane-2-yl. Other examples of “heterocyclyl” are partially or fully hydrogenated heterocyclic groups having two heteroatoms selected from N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl, 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl, 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl, 2,3-dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl, 1- or 2- or 3- or 4-imidazolidinyl, 2,3-dihydro-1H-imidazole-1- or 2- or 3- or 4-imidazole, 2,5-dihydro-1H-imidazole-1- or 2- or 3- or 4-imidazole 1- or 2- or 4- or 5-yl, 4,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl, hexahydropyridazine-1- or 2- or 3- or 4-yl, 1,2,3,4-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,2,3,6-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl, 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl, 4,5-dihydropyridazine-3- or 4-yl, 3, 4-dihydropyridazine-3- or 4- or 5- or 6-yl, 3,6-dihydropyridazine-3- or 4- or 5- or 6-yl, hexahydropyrimidin-1- or 2- or 3- or 4-yl, 1,4,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl, 1,2,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl, 1,2,3,4-tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl, 1,6-dihydropyrimidin-1- or 2- or 4- or 5- or 6 -yl, 1,2-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl, 2,5-dihydropyrimidin-2- or 4- or 5-yl, 4,5-dihydropyrimidin-4- or 5- or 6-yl, 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl, 1- or 2- or 3-piperazinyl, 1,2,3,6-tetrahydropyrazine-1- or 2- or 3- or 5- or 6-yl, 1,2,3,4-tetrahydropyrazine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,2-dihydropyrazine-1- or 2- or 3- or 5- or 6-yl, 1,4-dihydropyrazine-1- or 2- or 3-yl, 2,3-dihydropyrazine-2- or 3- or 5- or 6-yl, 2,5-dihydropyrazine-2- or 3-yl, 1,3-dioxol-2- or 4-yl, 1,3-dioxan-2- or 4- or 5-yl, 4H-1,3-dioxin-2- or 4- or 5- or 6-yl, 1,4-dioxin-2- or 3- or 5- or 6-yl, 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl, 1,4-dioxin-2- or 3- or 1,2- dithiolan-3- or 4-yl, 3H-1,2-dithiolan-3- or 4- or 5-yl, 1,3-dithiolan-2- or 4-yl, 1,3-dithiolan-2- or 4-yl, 1,2-dithian-3- or 4-yl, 3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl, 3,6-dihydro-1,2-dithiin-3- or 4-yl, 1,2-dithiin-3- or 4-yl, 1,3-dithiol-2- or 4- or 5-yl, 4H-1,3-dithiin-2- or 4 1,3-oxazolidin-2- or 3- or 4- or 5-yl, 2,3-dihydroisoxazol-2- or 3- or 4- or 5-yl, 2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl, 4,5-dihydroisoxazol-3- or 4- or 5-yl, 1,3-oxazolidin-2- or 3- or 4- or 5-yl, 2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl, 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl, 4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl, 1,2-oxazinan-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5-yl. 4- or 5- or 6-yl, 3,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl, 2H-1,2-oxazine-2- or 3- or 4 - or 5- or 6-yl, 6H-1,2-oxazine-3- or 4- or 5- or 6-yl, 4H-1,2-oxazine-3- or 4- or 5- or 6-yl, 1,3-oxazinane-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,3-oxazine-2- or 4- or 5- or 6-yl, 5,6-dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl, 2H-1,3-oxazine-2- or 4- or 5- or 6-yl, 6H-1,3-oxazine-2- or 4- or 5- or 6-yl, 4H-1,3-oxazine-2- or 4- or 5- or 6-yl, morpholin-2- or 3- or 4-yl, 3,4-dihydro-2H-1,4-oxazine-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,4-oxazine-2- or 3- or 5- or 6-yl, 2H-1,4-oxazine-2- or 3- or 5- or 6-yl, 4H-1,4-oxazin-2- or 3-yl, 1,2-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,5-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5,6,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl, 4,5,6 ,7-tetrahydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl, 2,3-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2,7-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl, 4,5-dihydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-1,2-oxazepine-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, 1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl, 1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,5-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5,6,7-tetrahydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl, 4,5,6,7-tetrahydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl, 2,3-dihydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl, 2,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl, 4,5-dihydro-1,3-oxazacyclopine-2- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-1,3-oxazacyclopine-2- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-1,3-oxazacyclopine-2- or 4- or 5- or 6- or 7-yl, 1,3-oxazacyclopine 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl, 2,3,4,5-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl 6- or 7-yl, 2,3,6,7-tetrahydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl, 2,5,6,7-tetrahydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl, 4,5,6,7-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl -yl, 2,3-dihydro-1,4-oxazacyclopine-2- or 3- or 5- or 6- or 7-yl, 2,5-dihydro-1,4-oxazacyclopine-2- or 3- or 5- or 6- or 7-yl, 2,7-dihydro-1,4-oxazacyclopine-2- or 3- or 5- or 6- or 7-yl, 4,5-dihydro-1,4-oxazacyclopine-2- or 3- or 5- or 6- or 7-yl, 4,7-dihydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl, 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl, isothiazolidine-2- or 3- or 4- or 5-yl, 2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl, 2,5-dihydroisothiazol-2- or 3- or 4- or 5-yl, 4,5-dihydroisothiazol-3- or 4- or 5-yl, 1,3-thiazolidine-2- or 3- or 4- or 5-yl, 2,3-dihydro-1,3-thiazol-2- or 3- or 4- or 5-yl, 2,5-dihydro-1,3-thiazol-2- or 4- or 5-yl, 4,5-dihydro-1,3-thiazol-2- or 4- or 5-yl, 1,3-thiazinane-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,3-thiazin-2- or 4- or 5- or 6-yl, 5,6-dihydro-4H-1,3-thiazin-2- or 4- or 5- or 6-yl, 2H-1,3-thiazin-2- or 4- or 5- or 6-yl, 6H-1,3-thiazin-2- or 4- or 5- or 6-yl, 4H-1,3-thiazin-2- or 4- or 5- or 6-yl. Other examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic groups having 3 heteroatoms selected from N, O and S, for example 1,4,2-dioxazolidine 2- or 3- or 5-yl, 1,4,2-dioxazol-3- or 5-yl, 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl, 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl, 1,4,2-dioxazin-3- or 5- or 6-yl, 1,4,2-dioxazepane-2- or 3- or 5- or 6-yl, 6,7-dihydro-5H-1,4,2-dioxaazepine-3- or 5- or 6- or 7-yl, 2,3-dihydro-7H-1,4,2-dioxaazepine-2- or 3- or 5- or 6- or 7-yl, 2,3-dihydro-5H-1,4,2-dioxaazepine-2- or 3- or 5- or 6- or 7-yl, 5H-1,4,2-dioxaazepine-3- or 5- or 6- or 7-yl, 7H-1,4,2-dioxaazepine-3- or 5- or 6- or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below:,

[0143]

[0144]

[0145]

[0146] The heterocycles listed above are preferably substituted by, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkyloxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trialkylsilylalkynyl, nitro, amino, cyano, halo The invention also includes but is not limited to the following: alkylamino, alkylamino, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio, alkylthio

[0147] When the base structure is substituted with "one or more radicals" from a list of radicals (=radicals) or a group of radicals defined generically, this includes in each case simultaneous substitution with a plurality of identical and / or structurally different radicals.

[0148] In the case of a partially or fully saturated nitrogen heterocycle, it may be attached to the remainder of the molecule via the carbon or via the nitrogen.

[0149] Suitable substituents for substituted heterocyclic groups are the substituents further specified below, as well as oxo and thio. Then, oxo groups as substituents on ring carbon atoms are, for example, carbonyl groups in heterocycles. Therefore, lactones and lactams are preferably also included. Oxo groups may also occur on ring heteroatoms, which may exist in different oxidation states, for example in the case of N and S, and in this case, in heterocycles, for example, divalent -N(O)-, -S(O)- (also referred to as SO) and S(O) are formed. 2 (Also referred to as SO 2 In the case of -N(O)- and -S(O)- groups, both enantiomers are included in each case.

[0150] According to the invention, the expression "heteroaryl" denotes heteroaromatic compounds, ie fully unsaturated aromatic heterocyclic compounds, preferably 5- to 7-membered rings having 1 to 4, preferably 1 or 2, identical or different heteroatoms, preferably O, S or N. The heteroaryl group of the present invention is, for example, 1H-pyrrol-1-yl, 1H-pyrrol-2-yl, 1H-pyrrol-3-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, 1H-imidazol-1-yl, 1H-imidazol-2-yl, 1H-imidazol-4-yl, 1H-imidazol-5-yl, 1H-pyrazol-1-yl, 1H-pyrazol-3-yl, 1H-pyrazol-4-yl, 1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-6-yl, 2H-1,2,3-triazol-7-yl, 2H-1,2,3-triazol-8-yl, 2H-1,2,3-triazol-9-yl, 2H-1,2,3-triazol-10-yl, 2H-1,2,3-triazol-20-yl, 2H-1,2,3-triazol-30-yl, 2H-1,2,3-triazol-40-yl, 2H-1,2,3-triazol-50-yl, 2H-1,2,3-triazol-60-yl, 2H-1,2,3-triazol-70-yl, 2H-1,2,3-triazol-80-yl, 2H-1,2,3-triazol-90-yl, 2H-1,2,3-triazol-10-yl, 2H-1 3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, azepine, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidine- 2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-oxazinyl, 1,3,2-oxazinyl, 1,3,6-oxazinyl and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol- The heteroaryl groups of the present invention may also be substituted by one or more identical or different groups. If two adjacent carbon atoms are part of another aromatic ring, the system is a fused heteroaromatic system, for example a benzo-fused or polyannelated heteroaromatic compound.Preferred examples are quinoline (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl), isoquinoline (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, pyridopyrazine, pyridopyrimidine, pyridopyridazine, pteridine, pyrimidopyrimidine. Examples of heteroaryl are also 5- or 6-membered benzo-fused rings selected from 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophene-2-yl, 1-benzothiophene-3-yl, 1-benzothiophene-4-yl , 1-benzothiophene-5-yl, 1-benzothiophene-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-7-yl indol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl, 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H-benzimidazol-7-yl, 1,3-benzooxazol-2-yl, 1,3-benzooxazol-4-yl, 1,3-benzooxazol-5-yl, 1,3-benzooxazol-6-yl, 1,3-benzoxazol-7-yl, 1,3-benzothiazol-2-yl, 1 ,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,2-benzisoxazol-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,

[0151] The term "halogen" denotes, for example, fluorine, chlorine, bromine or iodine. If the term is applied to a radical, "halogen" denotes, for example, a fluorine, chlorine, bromine or iodine atom.

[0152] According to the invention, "alkyl" means a linear or branched open-chain saturated hydrocarbon radical, which is optionally monosubstituted or polysubstituted, and in the case of monosubstituted or polysubstituted is referred to as "substituted alkyl". Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro, particularly preferably methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine. The prefix "di" also includes combinations of different alkyl groups, such as methyl (ethyl) or ethyl (methyl).

[0153] "Haloalkyl", "haloalkenyl" and "haloalkynyl" refer to alkyl, alkenyl and alkynyl groups, respectively, which are partially or fully substituted with the same or different halogen atoms, such as monohaloalkyl, such as CH 2 CH 2 Cl, CH 2 CH 2 Br, CHClCH 3 , CH 2 Cl, CH 2 F; perhaloalkyl, such as 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.

[0154] "Haloalkoxy" is, for example, OCF 3 , OCHF 2 、OCH 2 F. OCF 2 CF 3 、OCH 2 CF 3 and OCH 2 CH 2 Cl; this applies correspondingly to haloalkenyl and other halogen-substituted groups.

[0155] The expression "(C 1 -C 4"(C-alkyl" is a shorthand term for a straight or branched alkyl group having 1 to 4 carbon atoms, depending on the carbon atom range, i.e., including methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl groups. General alkyl groups with a larger specified carbon atom range, such as "(C 1 -C 6 )-alkyl", correspondingly also includes straight-chain or branched alkyl groups with a larger number of carbon atoms, that is, according to the example, also includes alkyl groups with 5 and 6 carbon atoms.

[0156] Unless otherwise specified, in the case of hydrocarbon groups such as alkyl, alkenyl and alkynyl groups, including hydrocarbon groups in composite groups, preferably lower carbon skeletons, for example, have 1 to 6 carbon atoms, or have 2 to 6 carbon atoms in the case of unsaturated groups. Alkyl groups, including alkyl groups in composite groups such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, tert-butyl or 2-butyl, pentyl, hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl, heptyl such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl groups are defined as possible unsaturated groups corresponding to alkyl groups, in which there is at least one double bond or triple bond. Groups with one double bond or triple bond are preferred.

[0157] The term "alkenyl" also specifically includes straight or branched open chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, and allenyl or cumulenyl radicals having one or more cumulative double bonds, such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl. Alkenyl means, for example, vinyl which may be optionally substituted with other alkyl radicals, such as (but not limited to) (C 2 -C 6)-alkenyl, such as vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 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. 1-methyl-3-pentenyl, 1-methyl-2-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 ... 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 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.

[0158] The term "alkynyl" also particularly includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1-yl. (C 2 -C 6)-Alkynyl represents, 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-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.

[0159] The term "cycloalkyl" refers to a carbocyclic saturated ring system having preferably 3 to 8 ring carbon atoms, for example 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, dialkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, this includes ring systems with substituents, and also includes substituents with double bonds on the cycloalkyl group, for example alkylidene groups, such as methylidene. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems are also included, for example bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptan-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, as well as systems such as 1,1′-di(cyclopropyl)-1-yl, 1,1′-di(cyclopropyl)-2-yl. The term “(C 3 -C 7 )-cycloalkyl" is an abbreviation for a cycloalkyl group having three to seven carbon atoms corresponding to the specified carbon atom range.

[0160] In the spiral-(C 5 -C9 )-alkyl, also included are spirocycloaliphatic systems such as spiro[2.2]pent-1-yl, spiro[2.2]pent-2-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex-2-yl, spiro[2.3]hex-4-yl, spiro[2.3]hex-5-yl, spiro[3.3]hept-1-yl, spiro[3.3]hept-2-yl.

[0161] In the two-spiro-(C 7 -C 8 )-alkyl, also includes dispirocycloaliphatic systems, such as dispiro[2.0.2 4 .1 3 ]hept-7-yl, dispiro[2.0.2 4 .1 3 ]hept-1-yl, dispiro[2.0.2 4 .2 3 ]Oct-7-yl, dispiro[2.0.2 4 .2 3 ]Oct-1-yl, dispiro[2.0.3 4 .1 3 ]Oct-1-yl, dispiro[2.0.3 4 .1 3 ]Oct-8-yl, dispiro[2.0.3 4 .1 3 ]Oct-5-yl, dispiro[2.0.3 4 .1 3 ]Oct-8-yl, dispiro[2.0.3 4 .1 3 ]Oct-6-yl, dispiro[2.1.2 5 .1 3 ]Oct-4-yl, dispiro[2.1.2 5 .1 3 ]Oct-4-yl, dispiro[2.1.2 5 .1 3 ]Oct-1-yl.

[0162] "Cycloalkenyl" means a carbocyclic, nonaromatic, partially unsaturated ring system having preferably 4 to 8 carbon atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, also including substituents having double bonds on the cycloalkenyl radical, for example alkylene radicals, such as methylene. In the case of optionally substituted cycloalkenyl, the statements for substituted cycloalkyl apply accordingly.

[0163] The term "alkylidene", for example (C 1 -C10 )-alkylene groups, and also represent straight-chain or branched open-chain hydrocarbon groups connected by double bonds. The possible bonding sites of alkylene groups are naturally only the positions where two hydrogen atoms in the basic structure can be replaced by double bonds; the group is, for example, =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 Cycloalkylene represents a carbocyclic group bonded via a double bond.

[0164] The term "alkylene", for example (C 1 -C 8 )-alkylene forms represent straight or branched open-chain hydrocarbon groups connected to other groups at two positions.

[0165] "Alkoxyalkyl" refers to an alkoxy group bonded through an alkyl group, and "alkoxyalkoxy" refers to an alkoxyalkyl group bonded through an oxygen atom, for example, but not limited to, methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propoxy.

[0166] "Arylalkyl" means an aryl group bonded through an alkyl group, "heteroarylalkyl" means a heteroaryl group bonded through an alkyl group, and "heterocyclylalkyl" means a heterocyclyl group bonded through an alkyl group.

[0167] "Cycloalkylalkyl" means a cycloalkyl group bonded through an alkyl group, for example, but not limited to, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl.

[0168] "Arylalkenyl" refers to an aryl group bonded through an alkenyl group, "heteroarylalkenyl" refers to a heteroaryl group bonded through an alkenyl group, and "heterocyclylalkenyl" refers to a heterocyclyl group bonded through an alkenyl group.

[0169] "Arylalkynyl" means an aryl group bonded through an alkynyl group, "heteroarylalkynyl" means a heteroaryl group bonded through an alkynyl group, and "heterocyclylalkynyl" means a heterocyclyl group bonded through an alkynyl group.

[0170] According to the invention, "haloalkylthio" - itself or as a component of a chemical group - is a linear or branched S-haloalkyl group preferably having 1 to 8 or 1 to 6 carbon atoms, for example (C 1 -C 8 )-halogenated alkylthio, (C 1 -C 6 )-halogenated alkylthio or (C 1 -C 4 )-haloalkylthio, such as (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.

[0171] “Halocycloalkyl” and “halocycloalkenyl” respectively refer to cycloalkyl or cycloalkenyl groups which are partially or fully substituted by the same or different halogen atoms (such as F, Cl and Br) or by haloalkyl groups (such as trifluoromethyl or difluoromethyl), for example 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, and 3,3-difluorocyclobutyl.

[0172] Synthesis of substituted N-phenyluracils of general formula (I).

[0173] The substituted N-phenyluracils of the general formula (I) of the present invention can be prepared using known methods. The synthetic routes used and studied start from commercially available or easily prepared heteroaromatic amines and correspondingly substituted hydroxy esters. In the following schemes, unless illustrative and non-limiting definitions are given, the moieties G, Q, R in the general formula (I) are 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7, X and Y have the meanings defined above. As the first key intermediate for synthesizing the compound of the general formula (I) of the present invention (wherein X is sulfur (S) and Y is oxygen (O)), an optionally further substituted mercaptophenyl-1H-pyrimidine-2,4-dione is prepared. This is shown, for example but not limited to, by the synthesis of 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (IIa) (Scheme 1). To this end, a suitable substituted aniline, such as but not limited to 2-fluoro-4-chloroaniline, is converted into the corresponding isocyanate with a suitable reagent, such as triphosgene, in a suitable polar aprotic solvent, such as dichloromethane, which is in a next step converted into the corresponding pyrimidine-2,4-dione, optionally further substituted, such as but not limited to 3-(4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione, by reaction with a suitable aminoacrylate using a suitable base, such as sodium hydride or potassium tert-butoxide, in a suitable polar aprotic solvent, such as N,N-dimethylformamide (Scheme 1). Subsequent sulfonation and chlorination with a suitable reagent (e.g., chlorosulfonic acid) followed by reduction with a suitable reducing agent (e.g., zinc in EtOH and HCl, tin (II) chloride hydrate or triphenylphosphine) can prepare the desired mercaptophenyl-1H-pyrimidine-2,4-dione, such as, but not limited to, 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (IIa) (see KR1345394, EP1122244, EP408382, WO 2003 / 029226, WO2010 / 038953, US2011 / 0224083, KR2011 / 110420). In the following scheme 1, R 2 and R 3 For example but not limited to fluorine, R 4 For example but not limited to, it is chlorine, and X is for example but not limited to, it is sulfur.

[0174]

[0175] The synthesis of the key intermediate (IIa) described in Scheme 1 is also applicable to the preparation of similar intermediates. After compound (II) is converted into intermediate (III) in the 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)) and in the presence of a suitable ligand (e.g. 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene) and a suitable base (e.g. diisopropyl(ethyl)amine) in a suitable polar aprotic solvent (e.g. dioxane), the corresponding further substituted N-methyl-5-mercaptophenyl-1H-pyrimidine-2,4-dione intermediate (II) can be converted into the desired compound of the general formula (Ia) of the present invention, wherein X is sulfur (S) and Y is oxygen (O) (Scheme 2). In the following Scheme 2, Q, R 2 , R 3 and R 4 has the meaning of the present invention as described above. In addition, R 1 , R 5 , R 6 , R 7 For example, but not limited to, hydrogen, X for example, but not limited to, sulfur, Y for example, but not limited to, oxygen, and G for example, but not limited to, CH 2 . The corresponding intermediate (III) described exemplarily but not limiting in Scheme 2 can be converted into the corresponding oxoalkanoate intermediate (IVa, IVb) or the desired target compound of general formula (Ia) by reacting with a suitable optionally further substituted iodoalkanoate (in Scheme 3, for example but not limited to iodoacetate) using a suitable base (e.g., silver (I) carbonate) in a suitable polar aprotic solvent (e.g., n-hexane or cyclohexane) at high temperature (e.g., under microwave conditions) (see Synthesis 2009, 2725). The corresponding iodoalkanoate can be prepared by known routes in the literature (see Eur. J. Org. Chem., 2006, 71, 8459; WO 2012 / 037573; Organometallics, 2009, 28, 132).

[0176]

[0177] The ethyl ester (IVa) and tert-butyl ester (IVb) intermediates can then be converted to the corresponding free acid (V) under appropriate reaction conditions [using an acid such as hydrochloric acid or acetic acid in the case of (IVa) or trifluoroacetic acid (TFA) in the case of (IVb)]. The desired substituted N-phenyluracil of general formula (Ia) can be prepared by reacting the corresponding acid intermediate (V) with a suitable compound QH under the mediation of a suitable coupling agent (e.g., HOBt = 1-hydroxybenzotriazole, EDC = 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, HATU = O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, T3P = 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphine 2,4,6-trioxide) and a suitable base (e.g., diisopropylethylamine, triethylamine) in a suitable polar aprotic solvent (e.g., dichloromethane, chloroform). Alternatively, the ethyl ester (IVa) can be converted to the corresponding desired substituted N-phenyluracil of general formula (Ia) by coupling with a suitable compound QH under the mediation of a suitable Lewis acid (eg indium(III) chloride) (see WO2011 / 1307088).

[0178] The preparation of compounds of the general formula (I) in which X and Y are, for example but not limited to, oxygen (O) begins with the synthesis of a key intermediate (VI) having a fluorine substituent in the 5-position, such as 3-(2,5-difluoro-4-nitro)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (VIa). To this end, a suitable substituted aniline, such as but not limited to 2,5-difluoroaniline, is converted into the corresponding isocyanate with a suitable reagent, such as triphosgene, in a suitable polar aprotic solvent, such as dichloromethane, which is in a next step converted into the corresponding pyrimidine-2,4-dione, which is optionally further substituted, here, for example but not limited to 3-(2,5-difluorophenyl)-6-trifluoromethyl-1H-pyrimidine-2,4-dione (Scheme 3), by reaction with a suitable aminoacrylate using a suitable base, such as sodium hydride or potassium tert-butoxide, in a suitable polar aprotic solvent, such as N,N-dimethylformamide. Nitration with a suitable nitrating agent and subsequent N-methylation with a suitable methylating agent provides the desired intermediate, here, for example but not limited to 3-(2,5-difluoro-4-nitro)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (VIa). In the following Scheme 3, R 2 and R 3 For example but not limited to fluorine, and R 4 For example but not limited to, nitro.

[0179]

[0180] Then, the intermediate (VI) obtained in the above manner, such as compound (VIa), can be converted into the desired substituted N-phenyluracil (Ib, R 4 = nitro) using a suitable base (such as potassium carbonate) and a suitable substituted 2-oxoalkoxy-1-hydroxybenzene (VII) in a suitable polar aprotic solvent (such as N,N-dimethylformamide (DMF)). The intermediate (VII) for this purpose can be obtained by a multi-step synthesis starting from commercially available 1-chloro-2-nitrobenzene, through (i) base-mediated coupling (such as with sodium hydride) with a suitable substituted hydroxyalkyl carbonyl reagent in a suitable polar aprotic solvent (such as tetrahydrofuran or dioxane), or by reacting 2-nitrophenol with a suitable substituted chloromethyl carbonyl reagent, (ii) reducing the nitro group with a suitable reducing agent (such as hydrogen, palladium on carbon in a suitable polar protic solvent), (iii) diazotization (with a suitable diazotizing reagent, such as tert-butyl nitrite (t-BuONO), boron trifluoride diethyl etherate (BF 3 -OEt 2 )) in a suitable polar aprotic solvent (such as dichloromethane (DCM), dimethoxyethane), (iv) reacting with acetic anhydride, and (v) releasing the hydroxy group by removing the acetyl protecting group (such as base-mediated with potassium carbonate in a polar protic solvent). Then, the nitro group in compound (Ib) can be converted into a halogen substituent (such as chlorine, bromine) by reduction and subsequent Sandmeyer reaction, and thus the desired substituted N-phenyluracil (Ic) can be obtained in this way. In Scheme 4 below, Q and R 2 have the meanings as defined in the present invention above. In addition, R 3 is, for example but not limited to, fluorine, R 4 is, for example but not limited to, chlorine or nitro, R 1 , R 5 , R 6 , R 7 are, for example but not limited to, hydrogen, X and Y are, for example but not limited to, oxygen, and G is, for example but not limited to, CH 2 .

[0181]

[0182] Thus, the intermediate (VI) obtained in the above manner can be converted into the desired substituted N-phenyluracil (Id, R 4= nitro), wherein X = O (oxygen) and Y = S (sulfur). The intermediate (VIII) used for this purpose can be prepared by a multistep synthesis analogous to the synthesis of intermediate (VII) described in Scheme 4, starting from commercially available 1-chloro-2-nitrobenzene or 2-nitrothiophenol. The nitro group in compound (Id) can then be converted into a halogen substituent (e.g. chlorine, bromine) by reduction and subsequent Sandmeyer reaction, so that the desired substituted N-phenyluracil (Ie) can be obtained in this way. In the following Scheme 5, Q and R 2 has the meaning of the present invention as described above. In addition, R 3 For example but not limited to fluorine, R 4 For example, but not limited to, chlorine or nitro, R 1 , R 5 , R 6 , R 7 For example, but not limited to, hydrogen, X for example, but not limited to, oxygen, Y for example, but not limited to, sulfur, and G for example, but not limited to, CH 2 .

[0183]

[0184] After compound (III) is converted into an intermediate of the type (IX) in a first step with the aid of a suitable optionally further substituted iodothiophenol using a suitable base or using a suitable transition metal catalyst (e.g. tris(dibenzylideneacetone)dipalladium(0)) and in the presence of a suitable ligand (e.g. 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene) and a suitable base (e.g. diisopropyl(ethyl)amine) in a suitable polar aprotic solvent (e.g. dioxane), the further substituted N-methyl-5-mercaptophenyl-1H-pyrimidine-2,4-dione intermediate (II) can also be converted into the desired compound of the general formula (If) of the present invention, wherein X and Y are sulfur (S) (Scheme 6). Depending on the circumstances, it may be necessary to perform intermediate protection of the mercapto group using a suitable protecting group. The intermediate (IX) can then be reacted with a haloalkanecarboxylic acid having various substituents using a suitable base to obtain the desired compound of the general formula (If). In the following Scheme 6, Q, R 2 , R 3 and R 4 has the meaning of the present invention as described above. In addition, R 1 , R 5 , R 6 , R 7 For example, but not limited to, hydrogen, X and Y for example, but not limited to, sulfur, and G for example, but not limited to, CH 2 Again, for greater clarity, the reaction scheme is described in Scheme 6 below, for example but not limited to the use of iodoacetate. Also suitable for coupling with intermediate (IX) are analogous haloalkanecarboxylic acids (halogen = bromine or chlorine).

[0185]

[0186] Selected detailed synthesis examples of compounds of the general formula (I) according to the invention are shown below. The example numbers mentioned correspond to the numbering scheme in Tables I.1 to I.33 below. The chemical examples recorded in the subsequent sections are 1 H NMR spectral data ( 1 H-NMR: 400 MHz, solvent: CDCl 3 , CD 3 OD or d 6 =-DMSO, internal standard: tetramethylsilane δ=0.00 ppm) were obtained on a Bruker instrument and the signals listed have the meanings given below: br=broad, s=singlet, d=doublet, t=triplet, dd=doublet of doublet, ddd=doublet of doublet of doublet, m=multiplet, q=quartet, quint=quintet, sext=sextet, sept=septet, dq=doublet of quartet, dt=doublet of triplet. In the case of diastereomeric mixtures, either the distinct signal of each of the two diastereomers is recorded or the characteristic signal of the major diastereomer is recorded. 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.

[0187] Synthesis Example:

[0188] 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

[0189]

[0190] [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) was added to a solution of 1-cyclopropylethanol (0.035 g, 0.408 mmol) in 5 ml of dichloromethane, followed by the addition of 1-hydroxy-1H-benzotriazole hydrate (0.058 g, 0.379 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.073 g, 0.379 mmol) and 4-dimethylaminopyridine (10 mol%), and the mixture was stirred at room temperature for 4 hours. Water and dichloromethane were added to the reaction mixture, the aqueous phase was repeatedly extracted with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure.

[0191] After purification by column chromatography on silica gel with an n-heptane / ethyl acetate gradient, 0.122 g (71% of theory) of a colorless solid was obtained.

[0192] 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).

[0193] Example I.7-10: (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid cyclobutyl methyl ester

[0194]

[0195] [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) was added to a solution of 1-cyclobutylmethanol (0.035 g, 0.408 mmol) in 5 ml of dichloromethane, followed by the addition of 1-hydroxy-1H-benzotriazole hydrate (0.058 g, 0.379 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.073 g, 0.379 mmol) and 4-dimethylaminopyridine (10 mol%), and the mixture was stirred at room temperature for 4 hours. Water and dichloromethane were added to the reaction mixture, the aqueous phase was repeatedly extracted with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure.

[0196] After purification by column chromatography on silica gel with an n-heptane / ethyl acetate gradient, 0.139 g (81% of theory) of a colorless solid was obtained.

[0197] 1 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).

[0198] Example I.7-18: (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate spiro[2.2]pentan-1-ylmethyl ester

[0199]

[0200] [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy]acetic acid (0.170 g, 0.330 mmol) was added to a solution of spiro[2.2]pentan-1-ylmethanol (0.045 g, 0.463 mmol) in 5 ml of dichloromethane, followed by the addition of 1-hydroxy-1H-benzotriazole hydrate (0.066 g, 0.430 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.082 g, 0.043 mmol) and 4-dimethylaminopyridine (10 mol %), and the mixture was stirred at room temperature for 2 hours. Water and dichloromethane were added to the reaction mixture, the aqueous phase was repeatedly extracted with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure.

[0201] After purification by column chromatography on silica gel with an n-heptane / ethyl acetate gradient, 0.170 g (86% of theory) of a colorless solid was obtained.

[0202] 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).

[0203] Example I.8-1: (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid cyclopropyl methyl ester

[0204]

[0205] (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (450 mg, 0.84 mmol) was added to a solution of 1-cyclopropylmethanol (98%, 81 mg, 1.09 mmol) in 10 ml of dichloromethane, followed by the addition of 1-hydroxy-1H-benzotriazole hydrate (148 mg, 1.10 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (210 mg, 1.10 mmol) and a catalytic amount of 4-dimethylaminopyridine (10 mg), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was left to stand overnight, and the reaction was subsequently monitored by thin layer chromatography, which showed incomplete conversion, so 1-hydroxy-1H-benzotriazole hydrate (148 mg, 1.10 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (210 mg, 1.10 mmol) and a catalytic amount of 4-dimethylaminopyridine (10 mg) were added again. The mixture was stirred for another 5 hours at room temperature, and the reaction was monitored by thin layer chromatography to determine almost complete conversion. Water was added to the reaction mixture, the phases were separated by a separator cartridge, and the solvent was removed under reduced pressure. Purification by silica gel column chromatography with an n-heptane / ethyl acetate gradient gave (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid cyclopropylmethyl ester (477 mg, 95% of theory) as a colorless oil.

[0206] 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).

[0207] Example I.9-1: (2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid cyclopropyl methyl ester

[0208]

[0209] An initial charge of 10 ml of N,N-dimethylacetamide (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid cyclopropylmethyl ester (327 mg, 0.56 mmol) and zinc cyanide (69 mg, 0.59 mmol) and tetrakis(triphenylphosphine)palladium(0) (65 mg, 0.06 mmol) were stirred at an oil bath temperature of 180 degrees Celsius under argon for 1 hour. After TLC monitoring showed complete conversion, the reaction mixture was added to 10 ml of water and repeatedly extracted with ethyl acetate. The combined organic phases were washed twice with saturated sodium chloride solution, then dried over sodium sulfate, filtered, and then concentrated under reduced pressure.

[0210] The crude product was purified by column chromatography on silica gel with an n-heptane / ethyl acetate gradient to give cyclopropylmethyl (2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (201 mg, 64% of theory) as a colorless oil.

[0211] 1 H-NMR (CDCl 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).

[0212] Analogously to the preparation examples cited above and listed where appropriate and taking into account the general details relating to the preparation of substituted N-heterocyclyl-tetrahydropyrimidones and N-heteroaryltetrahydropyrimidones, the following compounds are obtained.

[0213]

[0214] Table I.1: Preferred compounds of formula (I.1) are compounds I.1-1 to I.1-25, in which Q has the meaning indicated in the respective row of Table 1. Compounds I.1-1 to I.1-25 in Table I.1 are therefore defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0215] Table 1:

[0216]

[0217]

[0218]

[0219] Table I.2: Preferred compounds of the formula (I.2) are compounds I.2-1 to I.2-25, in which Q has the meaning indicated in the respective row of Table 1. Compounds I.2-1 to I.2-25 in Table I.2 are therefore defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0220]

[0221] Table I.3: Preferred compounds of formula (I.3) are compounds I.3-1 to I.3-25, in which Q has the meaning indicated in the respective row of Table 1. Compounds I.3-1 to I.3-25 in Table I.3 are therefore defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0222]

[0223] Table I.4: Preferred compounds of formula (I.4) are compounds I.4-1 to I.4-25, in which Q has the meaning indicated in the respective row of Table 1. Compounds I.4-1 to I.4-25 in Table I.4 are therefore defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0224]

[0225] Table I.5: Preferred compounds of formula (I.5) are compounds I.5-1 to I.5-25, in which Q has the meaning indicated in the respective row of Table 1. Compounds I.5-1 to I.5-25 in Table I.5 are therefore defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0226]

[0227] Table I.6: Preferred compounds of formula (I.6) are compounds I.6-1 to I.6-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.6-1 to I.6-25 in Table I.6 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0228]

[0229] Table I.7: Preferred compounds of formula (I.7) are compounds I.7-1 to I.7-25, in which Q has the meaning indicated in the respective row of Table 1. Compounds I.7-1 to I.7-25 in Table I.7 are therefore defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0230]

[0231] Table I.8: Preferred compounds of formula (I.8) are compounds I.8-1 to I.8-25, in which Q has the meaning indicated in the respective row of Table 1. Compounds I.8-1 to I.8-25 in Table I.8 are therefore defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0232]

[0233] Table I.9: Preferred compounds of formula (I.9) are compounds I.9-1 to I.9-25, in which Q has the meaning indicated in the respective row of Table 1. Compounds I.9-1 to I.9-25 in Table I.9 are therefore defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0234]

[0235] Table I.10: Preferred compounds of formula (I.10) are compounds I.10-1 to I.10-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.10-1 to I.10-25 in Table I.10 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0236]

[0237] Table I.11: Preferred compounds of formula (I.11) are compounds I.11-1 to I.11-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.11-1 to I.11-25 in Table I.11 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0238]

[0239] Table I.12: Preferred compounds of formula (I.12) are compounds I.12-1 to I.12-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.12-1 to I.12-25 in Table I.12 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0240]

[0241] Table I.13: Preferred compounds of formula (I.13) are compounds I.13-1 to I.13-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.13-1 to I.13-25 in Table I.13 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0242]

[0243] Table I.14: Preferred compounds of formula (I.14) are compounds I.14-1 to I.14-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.14-1 to I.14-25 in Table I.14 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0244]

[0245] Table I.15: Preferred compounds of formula (I.15) are compounds I.15-1 to I.15-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.15-1 to I.15-25 in Table I.15 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0246]

[0247] Table I.16: Preferred compounds of formula (I.16) are compounds I.16-1 to I.16-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.16-1 to I.16-25 in Table I.16 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0248]

[0249] Table I.17: Preferred compounds of formula (I.17) are compounds I.17-1 to I.17-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.17-1 to I.17-25 in Table I.17 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0250]

[0251] Table I.18: Preferred compounds of formula (I.18) are compounds I.18-1 to I.18-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.18-1 to I.18-25 in Table I.18 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0252]

[0253] Table I.19: Preferred compounds of formula (I.19) are compounds I.19-1 to I.19-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.19-1 to I.19-25 in Table I.19 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0254]

[0255] Table I.20: Preferred compounds of formula (I.20) are compounds I.20-1 to I.20-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.20-1 to I.20-25 in Table I.20 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0256]

[0257] Table I.21: Preferred compounds of formula (I.21) are compounds I.21-1 to I.21-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.21-1 to I.21-25 in Table I.21 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0258]

[0259] Table I.22: Preferred compounds of formula (I.22) are compounds I.22-1 to I.22-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.22-1 to I.22-25 in Table I.22 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0260]

[0261] Table I.23: Preferred compounds of formula (I.23) are compounds I.23-1 to I.23-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.23-1 to I.23-25 ​​in Table I.23 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0262]

[0263] Table I.24: Preferred compounds of formula (I.24) are compounds I.24-1 to I.24-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.24-1 to I.24-25 in Table I.24 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0264]

[0265] Table I.25: The preferred compounds of formula (I.25) are compounds I.25-1 to I.25-25, where Q has the meanings shown in each row of Table 1. Thus, compounds I.25-1 to I.25-25 in Table I.25 are defined by the meanings of the corresponding entries 1 to 25 of Q in Table 1.

[0266]

[0267] Table I.26: The preferred compounds of formula (I.26) are compounds I.26-1 to I.26-25, where Q has the meanings shown in each row of Table 1. Thus, compounds I.26-1 to I.26-25 in Table I.26 are defined by the meanings of the corresponding entries 1 to 25 of Q in Table 1.

[0268]

[0269] Table I.27: The preferred compounds of formula (I.27) are compounds I.27-1 to I.27-25, where Q has the meanings shown in each row of Table 1. Thus, compounds I.27-1 to I.27-25 in Table I.27 are defined by the meanings of the corresponding entries 1 to 25 of Q in Table 1.

[0270]

[0271] Table I.28: The preferred compounds of formula (I.28) are compounds I.28-1 to I.28-25, where Q has the meanings shown in each row of Table 1. Thus, compounds I.28-1 to I.28-25 in Table I.28 are defined by the meanings of the corresponding entries 1 to 25 of Q in Table 1.

[0272]

[0273] Table I.29: The preferred compounds of formula (I.29) are compounds I.29-1 to I.29-25, where Q has the meanings shown in each row of Table 1. Thus, compounds I.29-1 to I.29-25 in Table I.29 are defined by the meanings of the corresponding entries 1 to 25 of Q in Table 1.

[0274]

[0275] Table I.30: The preferred compounds of formula (I.30) are compounds I.30-1 to I.30-25, where Q has the meanings shown in each row of Table 1. Thus, compounds I.30-1 to I.30-25 in Table I.30 are defined by the meanings of the corresponding entries 1 to 25 of Q in Table 1.

[0276]

[0277] Table I.31: Preferred compounds of formula (I.31) are compounds I.31-1 to I.31-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.31-1 to I.31-25 in Table I.31 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0278]

[0279] Table I.32: Preferred compounds of formula (I.32) are compounds I.32-1 to I.32-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.32-1 to I.32-25 in Table I.32 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0280]

[0281] Table I.33: Preferred compounds of formula (I.33) are compounds I.33-1 to I.33-25, in which Q has the meaning indicated in the respective row of Table 1. Thus, compounds I.33-1 to I.33-25 in Table I.33 are defined by the meaning of the corresponding entry numbers 1 to 25 of Q in Table 1.

[0282] NMR data of selected examples: Selected examples of compounds of general formula (I) 1 H NMR data were presented in two different ways, either (a) as conventional NMR data or (b) as described below. 1 H NMR peaks are presented as a table.

[0283] a) Conventional NMR interpretation

[0284] Embodiment 1.7-12: 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),6.92-6.90(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).

[0285] b) NMR peak list method

[0286] Selected Embodiments 1 H-NMR data1 H-NMR peaks are presented in the form of a list. For each signal peak, the δ value in ppm is listed first, followed by the signal intensity in parentheses. The δ value / signal intensity pairs for different signal peaks are listed separated by semicolons.

[0287] Thus, the peak list for one embodiment has the following form:

[0288] δ 1 (strength 1 );δ 2 (strength 2 );……;δ i (strength i );……;δ n (strength n )

[0289] The intensity of the sharp signal is related to the signal height in cm in the printed example of the NMR spectrum and shows the true scale of the signal intensity. In the case of broad peak signals, several peaks or the middle part of the signal can be shown and their relative intensities compared to the strongest signal in the spectrum.

[0290] To correct 1 The chemical shifts of H NMR spectra use those of tetramethylsilane and / or the solvent, particularly in the case of spectra measured in DMSO. Thus, the tetramethylsilane peak may, but need not, appear in the NMR peak list.

[0291] 1 H NMR peak lists and conventional 1 The H NMR printout is similar and therefore usually contains all the peaks listed in a conventional NMR description.

[0292] In addition, as usual 1 H NMR printouts, which may show solvent signals, signals of stereoisomers of the target compound (which are also provided by the present invention) and / or peaks of impurities.

[0293] When recording signals of compounds in the delta range of solvent and / or water, 1 The H NMR peak list shows standard solvent peaks, such as in DMSO-D 6 The peaks of DMSO and water in the sample generally have high intensities on average.

[0294] The peaks of stereoisomers of the target compound and / or peaks of impurities generally have an average intensity lower than that of the peak of the target compound (eg, having a purity of >90%).

[0295] Such stereoisomers and / or impurities may be specific to a particular method of preparation. Therefore, their peaks can help identify the reproducibility of a method of preparation by reference to a "by-product fingerprint".

[0296] A person skilled in the art who calculates the peaks of the target compound by known methods (MestreC, ACD simulation, and using empirically estimated expected values) can separate the peaks of the target compound as desired, optionally using additional intensity filters. This separation is similar to conventional 1 Peak selection as described in the H NMR description.

[0297] 1 Further details of the H NMR peak list can be found in the Research Disclosure Database No. 564025.

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306] The present invention also provides for the use of one or more compounds of the invention of the general formula (I) as defined above, preferably in one embodiment identified as preferred or particularly preferred, and / or their salts, in particular one or more compounds of the formulae (I.1) to (I.33) as defined above in each case, and / or their salts, as herbicides and / or plant growth regulators, preferably in crops of useful plants and / or ornamental plants.

[0307] The present invention also provides a method for controlling harmful plants and / or regulating plant growth, characterized in that an effective amount of

[0308] - one or more compounds of the general formula (I) according to the invention as defined above, preferably in one embodiment identified as preferred or particularly preferred, and / or their salts, in particular one or more compounds of the formulae (I.1) to (I.33) as defined above in each case, and / or their salts, or

[0309] - a composition of the invention as defined hereinafter,

[0310] Apply to (harmful) plants, (harmful) plant seeds, the soil or cultivation area in or on which (harmful) plants grow.

[0311] The invention also provides a method for controlling unwanted vegetation, preferably in crops of useful plants, characterized in that an effective amount of

[0312] - one or more compounds of the general formula (I) as defined above, preferably in one embodiment identified as preferred or particularly preferred, and / or their salts, in particular one or more compounds of the formulae (I.1) to (I.33) as defined above in each case, and / or their salts, or - a composition according to the invention as defined below,

[0313] Application to unwanted plants (e.g. harmful plants such as monocotyledonous weeds or dicotyledonous weeds or unwanted crop plants), seeds of unwanted plants (i.e. plant seeds, such as grains, seeds or vegetative propagation organs (such as tubers) or shoot parts with buds), soil in or on which unwanted plants grow (e.g. soil of crop-planting sites or non-crop-planting sites) or cultivated areas (i.e. areas on which unwanted plants grow).

[0314] The present invention further provides a method for controlling and regulating the growth of plants (preferably useful plants), characterized in that an effective amount of

[0315] - one or more compounds of the general formula (I) as defined above, preferably in one embodiment identified as preferred or particularly preferred, and / or their salts, in particular one or more compounds of the formulae (I.1) to (I.33) as defined above in each case, and / or their salts, or - a composition according to the invention as defined below,

[0316] Application to plants, plant seeds (i.e. plant seeds, such as grains, seeds or vegetative propagation organs (such as tubers) or young shoots with buds), soil in or on which plants grow (such as arable or non-arable soil) or cultivation areas (i.e. the area on which plants grow).

[0317] In this context, the compounds of the general formula (I) according to the invention or the compositions according to the invention can be applied, for example, by pre-sowing (if appropriate, also by incorporation into the soil), by the pre-emergence method and / or by the post-emergence method. Some representative specific examples of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention are as follows, although there is no intention to be restricted to the specific species listed.

[0318] In the method according to the invention for controlling harmful plants or for regulating plant growth, one or more compounds of the general formula (I) and / or their salts are preferably used to control harmful plants or to regulate the growth of crops of useful plants or ornamental plants, wherein in a preferred form, the useful plants or ornamental plants are transgenic plants.

[0319] The compounds of the general formula (I) and / or their salts according to the present invention are suitable for controlling monocotyledonous and dicotyledonous harmful plants of the following genera:

[0320] Monocotyledonous harmful plant genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Panicum (Eriochloa), Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0321] Dicotyledonous harmful plants: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 Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0322] When the compound of the general formula (I) of the present invention is applied to the soil surface before the harmful plants (grass weeds and / or broadleaf weeds) germinate (pre-emergence method), the emergence of seedlings of the grass weeds or broadleaf weeds can be completely prevented, or they grow until they reach the cotyledon stage, but then stop growing and eventually die completely after three to four weeks.

[0323] When the compounds according to the invention of the general formula (I) are applied to the green parts of the plants after emergence, growth is arrested after the treatment and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, thus eliminating weed competition that is harmful to the crop plants very early and in a permanent manner.

[0324] Although the compounds of the general formula (I) according to the invention show excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops are only slightly damaged or not damaged at all, depending on the structure of the corresponding compounds according to the invention and their application rate, such crop plants are, for example, dicotyledonous crop plants of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Flax. The compounds of the invention are particularly suitable for selectively controlling the growth of unwanted plants in plant crops, such as agriculturally useful plants or ornamental plants.

[0325] In addition, the compounds of the general formula (I) according to the invention (depending on their special structure and the application rate used) have excellent growth regulating properties in crop plants. They intervene in the metabolism of the plant itself by means of a regulatory action and can therefore be used for controlled influencing of plant components and facilitating harvesting, for example by inducing dehydration and dwarfing growth. In addition, they are also suitable for general control and inhibition of unwanted vegetative growth without killing the plant in the process. The inhibition of vegetative growth plays an important role for many monocotyledonous and dicotyledonous crops, since, for example, it can reduce or completely prevent lodging.

[0326] The compounds of the general formula (I) of the present invention can also be used to control harmful plants in genetically modified plant crops or plant crops modified by conventional mutagenesis by virtue of their weed control and plant growth regulating properties. Typically, transgenic plants are characterized by particularly advantageous properties, such as resistance to certain pesticides (especially certain herbicides), resistance to plant diseases or pathogens of plant diseases (e.g. certain insects or microorganisms such as fungi, bacteria or viruses). Other specific features relate, for example, to the quantity, quality, storage, composition and specific ingredients of the harvested material. For example, there are known transgenic plants with increased starch content or altered starch quality, or those with different fatty acid compositions in the harvested material.

[0327] As far as transgenic crops are concerned, the compounds of the general formula (I) according to the invention and / or their salts are preferably used in transgenic crops of economically important useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, millet, rice and corn, or crops such as beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.

[0328] The compounds of the general formula (I) according to the invention are preferably also employed as herbicides in crops of useful plants which are resistant to the phytotoxic effects of herbicides or have been rendered resistant by recombinant methods.

[0329] The compounds of the general formula (I) of the present invention can also be used to control harmful plants in crops of known or yet to be developed genetically modified plants by virtue of their weed control and plant growth regulating properties. Typically, transgenic plants are characterized by particularly advantageous properties, such as resistance to certain pesticides (particularly certain herbicides), resistance to plant diseases or pathogens of plant diseases (e.g. certain insects or microorganisms such as fungi, bacteria or viruses). Other specific features relate, for example, to the quantity, quality, storage, composition and specific ingredients of the harvested material. For example, there are known transgenic plants with increased starch content or altered starch quality, or those with different fatty acid compositions in the harvested material. Other specific properties may be tolerance or resistance to abiotic stress factors (e.g. heat, cold, drought, salinity and ultraviolet radiation).

[0330] Preference is given to the use of the compounds of the general formula (I) according to the invention or their salts in transgenic crops of economically important useful and ornamental plants, such as cereals, such as wheat, barley, rye, oats, triticale, millet, rice, cassava and corn, or crops such as sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.

[0331] The compounds of the general formula (I) are preferably employed as herbicides in crops of useful plants which are resistant to the phytotoxic effects of the herbicides or have been rendered resistant by recombinant methods.

[0332] Conventional methods for producing novel plants with improved properties compared to existing plants comprise, for example, conventional breeding methods and the generation of mutants. Alternatively, novel plants with altered properties can be produced with the aid of recombinant methods.

[0333] A large number of molecular biological techniques by which new transgenic plants with improved properties can be produced are known to those skilled in the art. For this genetic manipulation, nucleic acid molecules that allow mutation or sequence change by DNA sequence recombination can be introduced into plasmids. By means of standard methods, for example, base exchange, removal of partial sequences or addition of natural or synthetic sequences can be performed. For connecting DNA fragments to each other, adapters or linkers can be added to the fragments.

[0334] The production of plant cells with reduced activity of a gene product can be achieved, for example, by expressing at least one corresponding antisense RNA, a sense RNA for achieving co-suppression, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the above gene product.

[0335] For this purpose, firstly, DNA molecules can be used that contain the entire coding sequence of the gene product, including any flanking sequences that may be present, as well as DNA molecules that contain only parts of the coding sequence, in which case these parts need to be long enough to have an antisense effect in the cell. DNA sequences that have a high degree of homology to the coding sequence of the gene product, but are not completely identical thereto, can also be used.

[0336] When expressing nucleic acid molecules in plants, the synthesized protein can be located in any desired compartment of the plant cell. However, to achieve localization in a specific compartment, for example, the coding region can be linked to a DNA sequence that ensures localization in a specific compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). Nucleic acid molecules can also be expressed in organelles of plant cells.

[0337] The transgenic plant cells can be regenerated by known techniques to give whole plants. In principle, the transgenic plants can be plants of any desired plant species, ie not only monocotyledons but also dicotyledons.

[0338] In this way, transgenic plants can be obtained which have altered properties by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences, or expression of heterologous (=foreign) genes or gene sequences.

[0339] The compounds of the general formula (I) according to the invention are preferably used in transgenic crops which are resistant to growth regulators such as dicamba, or to herbicides which inhibit essential plant enzymes such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD), or to herbicides selected from the group consisting of sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and similar active ingredients.

[0340] When the compounds of the general formula (I) of the present invention are used in transgenic crops, not only the effects on harmful plants observed in other crops occur, but also the specific effects of application in specific transgenic crops generally occur, such as an altered or especially broadened spectrum of controllable weeds, an altered application rate that can be used for application, preferably good compatibility with herbicides to which the transgenic crops are resistant, and an influence on the growth and yield of transgenic crop plants.

[0341] The present invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or their salts as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crop plants.

[0342] Preferably, the application is carried out in cereals by the pre-emergence method or the post-emergence method, the cereals being preferably corn, wheat, barley, rye, oats, millet or rice.

[0343] It is also preferred to use it in soybeans by the pre-emergence method or the post-emergence method.

[0344] The use according to the invention for controlling harmful plants or for growth regulation of plants also includes the case in which the compounds of the general formula (I) or their salts are not formed from precursor substances ("prodrugs") until after application on, in or in the soil.

[0345] The present invention also provides the use of one or more compounds of the general formula (I) or their salts or the compositions of the invention (as defined below) (in a certain method) for controlling harmful plants or for regulating plant growth, which comprises applying an effective amount of one or more compounds of the general formula (I) or their salts to plants (harmful plants, if appropriate, together with useful plants), plant seeds, soil or cultivation areas in which or on which plants grow.

[0346] The present invention also provides a herbicidal composition and / or a plant growth regulating composition, characterized in that the composition comprises

[0347] (a) one or more compounds of the general formula (I) as defined above, preferably in one embodiment identified as preferred or particularly preferred, and / or their salts, in particular one or more compounds of the formulae (I.1) to (I.33) as defined above in each case, and / or their salts,

[0348] and

[0349] (b) one or more other substances selected from group (i) and / or (ii):

[0350] (i) one or more further agrochemical active substances, preferably selected from insecticides, acaricides, nematicides, other herbicides (i.e. those not conforming to the general formula (I) as defined above), fungicides, safeners, fertilizers and / or other growth regulators,

[0351] (ii) one or more formulation auxiliaries customary in crop protection.

[0352] The other agrochemical active substances of component (i) of the composition of the present invention are preferably selected from the substances mentioned in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0353] The herbicidal composition or plant growth regulating composition of the present invention preferably comprises one, two, three or more formulation adjuvants (ii) commonly used in crop protection, wherein the formulation adjuvants are selected from surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers which are solid at 25° C. and 1013 mbar (preferably adsorptive granular inert materials), wetting agents, antioxidants, stabilizers, buffer substances, defoamers, water, organic solvents (preferably organic solvents which are miscible with water in any proportion at 25° C. and 1013 mbar).

[0354] The compounds of the general formula (I) of the present invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in conventional formulations. Therefore, the present invention also provides herbicidal compositions and plant growth regulating compositions comprising the compounds of the general formula (I) and / or their salts.

[0355] The compounds of the general formula (I) according to the invention and / or their salts can be formulated in various ways, depending on the biological and / or physicochemical parameters specified. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) (such as oil-in-water emulsions and water-in-oil emulsions), sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), seed dressing products, granules for broadcasting and soil application, granules in microparticulate form (GR), sprayable granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV preparations, microcapsules and waxes.

[0356] These individual formulation types and formulation aids (such as inert materials, surfactants, solvents and other additives) are known to those skilled in the art and are described, for example, in the following literature: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd edition, Darland Books, Caldwell NJ; HvOlphen, "Introduction to Clay Colloid Chemistry", 2nd edition, J. Wiley & Sons, NY; C. Marsden, "Solvents Guide", 2nd edition, Interscience, NY 1963; McCutcheon's "Detergents and Emulsi-fiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "En-cyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Ver-lag Munich, 4th edition 1986.

[0357] Wettable powders are preparations which can be uniformly dispersed in water and which contain, in addition to the active ingredient, ionic and / or nonionic surfactants (wetting agents, dispersants) in addition to diluents or inert substances, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ether sulfates, alkyl sulfonates, alkylbenzene sulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. To prepare the wettable powders, the active herbicidal ingredient is finely ground in conventional apparatuses such as hammer mills, blower mills and jet mills and simultaneously or subsequently mixed with formulation adjuvants.

[0358] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent (e.g. butanol, cyclohexanone, dimethylformamide, xylene or relatively high-boiling aromatic compounds or hydrocarbons) or a mixture of organic solvents and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium salts of alkylarylsulfonic acids, for example calcium dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters (e.g. sorbitan fatty acid esters) or polyoxyethylene sorbitan esters (e.g. polyoxyethylene sorbitan fatty acid esters).

[0359] Dusting products are obtained by grinding the active ingredient with finely divided solids, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0360] Suspension concentrates may be water-based or oil-based. They may be prepared, for example, by wet grinding with the aid of a standard commercially available bead mill and optionally with the addition of surfactants such as those listed above for the other types of formulations.

[0361] Emulsions, such as oil-in-water emulsions (EW), can be prepared using aqueous organic solvents and optionally surfactants such as have been listed above for the other formulation types, with the aid of, for example, stirrers, colloid mills and / or static mixers.

[0362] Granules can be prepared by spraying the active ingredient onto a granular inert material capable of absorption or by applying the active ingredient concentrate to the surface of a carrier material such as sand, kaolin or granular inert material with the aid of a binder such as polyvinyl alcohol, sodium polyacrylate or mineral oil. Suitable active ingredients can also be granulated in a manner customary for the preparation of fertilizer granules, if desired mixed with fertilizers.

[0363] Water-dispersible granules are generally prepared by customary methods such as spray drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.

[0364] For the preparation of pan granules, fluidized bed granules, extruded granules and spray granules, see, for example, the methods in "Spray-Drying Handbook", 3rd edition 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq.; "Perry's Chemical Engineer's Handbook", 5th edition, McGraw-Hill, New York 1973, pages 8-57.

[0365] For further detailed information on the formulation of crop protection agents, see, for example, GC Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and JD Freyer, SA Evans, “Weed Control Handbook”, 5th edition, Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

[0366] The agrochemical preparations, preferably herbicidal compositions or plant growth regulating compositions of the present invention preferably contain the active ingredients of the general formula (I) and their salts in 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.

[0367] In wettable powders, the concentration of the active ingredient is, for example, about 10% to 90% by weight, and the remainder to 100% by weight is composed of conventional formulation ingredients. In emulsifiable concentrates, the concentration of the active ingredient may be about 1% to 90% by weight and preferably 5% to 80% by weight. Formulations in the form of dusting powders contain 1% to 30% by weight of active ingredients, preferably usually 5% to 20% by weight of active ingredients; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active ingredients. In the case of water-dispersible granules, the content of the active ingredient depends in part on whether the active ingredient is in liquid or solid form, as well as the granulation aids, fillers, etc. used. In water-dispersible granules, the content of the active ingredient is, for example, 1% to 95% by weight, preferably 10% to 80% by weight.

[0368] In addition, the active ingredient formulations mentioned optionally include various conventional adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents that influence pH and viscosity. Examples of formulation adjuvants are especially described in "Chemistry and Technology of Agrochemical Formulations", edited by D.A. Knowles, Kluwer Academic Publishers (1998).

[0369] The compound of the general formula (I) of the present invention or its salt can be used by itself or in the form of a preparation (formulation) combined with other pesticide active substances (e.g., insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators), for example in the form of a finished formulation or a tank mix. Taking into account the physical properties and stability of the active ingredients to be combined, the combined formulation can be prepared on the basis of the above-mentioned formulation.

[0370] Combination partners of the compounds of the general formula (I) which can be used according to the invention in mixed formulations or tank mixes are, for example, based on known active ingredients which inhibit the following enzymes: for example acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and in the literature cited therein.

[0371] Of particular concern is the selective prevention of harmful plants in crops of useful plants and ornamental plants. Although the compound of the general formula (I) of the present invention has shown very good to sufficient selectivity in a large number of crops, in principle, in some crops and particularly in the case of a mixture with other less selective herbicides, phytotoxicity to crop plants may occur. In this regard, the combination of the compound of the general formula (I) of the present invention that is particularly concerned comprises the compound of the general formula (I) or a combination thereof with other herbicides or pesticides and safeners. The safener used with the detoxification effective amount reduces the phytotoxic side effects of the herbicides / pesticides used in, for example, the following crops: economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), beet, sugarcane, rapeseed, cotton and soybeans, preferably cereals.

[0372] The weight ratio of herbicide (mixture) to safener generally depends on the application rate of the herbicide and the efficacy of the safener and can vary within a wide range, for example in the range of 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. Similar to the compounds of general formula (I) or mixtures thereof, the safener can be formulated with other herbicides / pesticides and can be provided and used as a finished formulation or tank mix containing the herbicide.

[0373] For application, the commercially available herbicide preparations or herbicide-safener preparations are diluted, if appropriate, in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersibles and water-dispersible granules with water. Preparations in the form of dusting powders, granules for soil application or granules for broadcasting and sprayable solutions are usually not diluted further with other inert substances before application.

[0374] The application rate of the compound of the general formula (I) of the present invention and / or its salt is affected by external conditions such as temperature, humidity, etc. to a certain extent. The application rate can be changed in a wide range. For the application as a herbicide for preventing and treating harmful plants, the total amount of the compound of the general formula (I) of the present invention and its salt is preferably 0.001 to 10.0 kg / ha, preferably 0.005 to 5 kg / ha, more preferably 0.01 to 1.5 kg / ha, and particularly preferably 0.05 to 1 kg / ha. This is applicable to both pre-emergence application and post-emergence application.

[0375] When the compounds of the general formula (I) according to the invention and / or their salts are used as plant growth regulators, for example as stalk stabilizers for crop plants as mentioned above (preferably cereals, such as wheat, barley, rye, triticale, millet, rice or corn), the total application rate is preferably 0.001 to 2 kg / ha, preferably 0.005 to 1 kg / ha, in particular 10 to 500 g / ha, very particularly preferably 20 to 250 g / ha. This applies both to pre-emergence and post-emergence applications.

[0376] Application as a stalk stabilizer can be carried out at various stages of plant growth. It is preferably applied after the tillering stage, when the longitudinal growth begins.

[0377] As an alternative, application as a plant growth regulator can also be carried out by treating the seeds (which includes various techniques for seed dressing and seed coating). The application rate depends on the specific technique and can be determined in preliminary trials.

[0378] Combination partners that can be used for the compounds of the general formula (I), for example in mixed formulations or tank mixes, are, for example, based on known active ingredients that inhibit the following enzymes: for example acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoene dehydrogenase, photosystem I, photosystem II or protoporphyrinogen oxidase, or known active ingredients that act as plant growth regulators, as known from, for example, Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.

[0379] Examples of known herbicides or plant growth regulators that can be combined with the compounds of general formula (I) include the following active ingredients (the compounds are referred to by their "common name" or chemical name or code number according to the International Organization for Standardization (ISO)), and always include all use forms, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers. For example, these substances include one use form and in some cases also a plurality of use forms:

[0380] Acetochlor, acifluorfen, acifluorfen-methyl, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazon, amidochlor, amidosulfuron, 4 -amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachloro-potassium, aminocyclopyrachloro-methyl, aminopyralid, aminopyralid-dimethylammonium, aminopyralid-tripromine, amitrol, aminosulfonate ammonium, sulphanol anilofos, asulam, asulam-potassium, asulam-sodium, atrazine, azafenidin, azimsulfuron, beflubutamid, (S)-(-)-beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, benazolin-dimethylammonium dimethylammonium), benazolin-potassium, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulid, bentazon, bentazon-sodium, benzobicyclon, benzofenap, bicyclopyrone, bifenox,Bialafos, bilanafos-sodium, bipyrazone, bispyribac, bispyribac-sodium, bixlozon, bromacil, bromacil-lithium, bromacil-sodium, bromobutid, bromofenoxim, bromoxynil, bromoxynil butyrate, bromoxynil-potassium, bromoxynil heptanoate and bromoxynil octanoate octanoate), busoxinon, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylat, cafenstrol, cambendichlor, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamine, chloramben-methyl methyl), chloramben-methylammonium, chloramben-sodium, chlorbromuron, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalimide,Chlorotoluron, chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-cinmethylin (i.e., (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane), exo-(-)-cinmethylin (i.e., (1 R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane), cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-ethyl, clodinafop-propargyl, clonazon, clomeprop, clopyralid, clopyralid-methyl, clopyralid-ethyl clopyralid-olamine, clopyralid-potassium, clopyralid-tripomine, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloat, cyclopyranil, cyclopyrimorat, cyclosulfamuron, cycloxydim, cyhalo fop, cyhalofop-butyl, cyprazine, 2,4-D (and 2,4-D ammonium, 2,4-D-butoxyethyl ester (2,4-D-butoyl), 2,4-D-butyl ester, 2,4-D-choline, 2,4-D-diethylammonium, 2,4-D-dimethylammonium, 2,4-D-diolamine, 2,4-D-doboxyl, 2,4-D-dodecylammonium, 2,4-D-etexyl, 2,4-D-ethyl ester, 2,4-D-2-ethylhexyl ester, 2,4-D-heptyl ammonium, 2,4-D-isobutyl ester, 2,4-D-isooctyl ester, 2,4-D-isopropyl ester, 2,4-D-isopropylammonium,2,4-D-lithium, 2,4-D-meptyl, 2,4-D-methyl ester, 2,4-D-potassium, 2,4-D-tetradecyl ammonium, 2,4-D-triethyl ammonium, 2,4-D-triisopropanolammonium, 2,4-D-tripromine and 2,4-D-trolamine (2,4-D-trolamine) salt), 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl ester, 2,4-DB-potassium and 2,4-DB-sodium, daimuron (dymron), dalapon, dalapon-calcium, dalapon-magnesium (dalapon-magnesium), dalapon-sodium, dazomet, dazomet-sodium, n-decanol, 7-deoxy-D-sedoheptulose, desmedipham, detosyl-pyrazolate (DTP), dicamba and its salts (e.g., dicamba-biproamine, dicamba-N,N-bis(3-aminopropyl)methylamine, dicamba-butotyl), dicamba Choline (dicamba-choline), dicamba diglycolamine salt (dicambadiglycolamine), dicamba dimethylammonium (dicamba-dimethylammonium), dicamba diethanolamine ammonium salt (dicamba-diethanolaminemmonium), dicamba diethylammonium (dicamba-diethylammonium), dicamba isopropylammonium (dicamba-isopropylammonium), dicamba methyl (dicamba-methyl), dicamba monoethanolamine (dicamba-monoethanolammonium ine), dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine), dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-butotyl,2,4-Dichlorprop-dimethylammonium, dichlorprop-etexyl, dichlorprop-ethylammonium, 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, difenzoq uat), difenzoquat-metilsulfate, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuro n, diinitramine, 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, ethiozin, ethofumesate, ethoxyfen, fluorine Ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5231 (i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide), F-7967 (i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl xaprop-ethyl), fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamid, flamprop, flamprop-isoproyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfone sulfuron), 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, flurenol-dimethylammonium, and flurenol-methyl ester lurenol-methyl), fluoroglycofen, fluoroglycofen-ethyl, flupropanat, flupropanat-sodium, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluridon, flurochloridon, clofopyrazole fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, foramsulfuron-sodium, fosamine, fosamine ammonium -ammonium), glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate, glyphosate-ammonium,glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-sesquisodium and glyphosate-trimesium, H-9201 (i.e. O-(2,4-dimethyl-6-nitrophenyl)- O-(2,4-Dimethyl-6-nitrophenyl)-O-ethylisopropylphosphoramidothioate), halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop ethoxyethyl ester -ethoxyethyl), haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, haloxifop-sodium, hexazinon, HNPC-A8169 (i.e., (2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propionic acid prop-2-yn-1-yl ester), HW-02 (i.e., (2,4-dichlorophenoxy)acetic acid 1-(dimethoxyphosphoryl)ethyl ester), hydantoci din, 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, iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl sodium =The following are some of the following: sodium), ioxynil, ioxynil-lithium, ioxynil-octanoate, ioxynil-potassium and ioxynil-sodium, ipfencarbazone, iptriazopyrid (i.e., 3-[(isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo-[4,3-a]pyridine-8-carboxamide), isoproturon, isoxazolone (i souron), isoxaben, isoxaflutole, karbutilate, KUH-043 (i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospiradox, ketospiradox-potassium, lactofen, lenacil, linuron, MCPA, MCPA-butoxyethyl ester (MCPA-butoxyethyl ester) l), MCPA-butyl, MCPA-dimethylammonium, MCPA-diolamine, MCPA-2-ethylhexyl, MCPA-ethyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine,MCPA - potassium, MCPA - sodium and MCPA - trolamine, MCPB, MCPB - methyl, MCPB - ethyl and MCPB - sodium, 2 - methyl - 4 - chloropropionic acid (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, mecoprop - P - dimethylammonium, mecoprop - P - 2 - ethylhexyl, mecoprop - P - 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, molinat, monolinuron, monosulfuron, monosulfuron-methyl, MT-5950 (i.e., N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide), NGGC-011, napropamide), NC-310 (i.e., 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole), neburon, nicosulfuron, pelargonic acid acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, paraquat dichloride dichloride), paraquat-dimethylsulfate, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, mineral oil, phenmedipham, phenmedipham-ethyl, picloram, picloram-dimethylammonium, picloram-etexyl, picloram-isoctyl, picloram-methyl, picloram-olamine, picloram-potassium, picloram-triethylammonium,picloram-tripromine, picloram-trolamine, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamines, profoxydim, prometon, prometryn, propachlor ), propanil, propaquizafop, propazines, propham, propisochlor, propoxycarbazones, propoxycarbazone-sodium, propyrisulfuron, propyzamid, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyrazosulfuron raflufen-ethyl), (pyraquinat), pyrasulfotol, pyrazolynat (pyrazolat), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb 、pyridafol、pyridat、pyriftalid、pyriminobac、pyriminobac-methyl、pyrimisulfan、pyrithiobac、pyrithiobac-sodium、pyroxasulfon、pyroxsulam、quinclorac、quinclorac-dimethylammonium、quinclorac-methyl、Quinmerac, quinoclamin, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM201 (i.e., 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one), rimsulfuron, saflufenac il), sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249 (i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate), SYP-300 (i.e., 1-[7-

[0045] fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione), 2,3,6-TBA, TCA (trichloroacetic acid) and its salts (such as ammonium trichloroacetate, calcium trichloroacetate, ethyl trichloroacetate, magnesium trichloroacetate, sodium trichloroacetate), tebuthiuron, tefuryltriones, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbutylazine (tebuthiuron), tefuryltriones, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbutylazine (tebuthiuron), tefuryltriones, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbutylazine (tebuthiuron), tefuryltriones, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthion ... rbuthylazines), terbutryn, tetflupyrolimet, thaxtomin, thenylchlor, thiazopyr, thiencarbazones, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralat, topramezon,tralkoxydim, triafamon, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-choline, triclopyr-ethyl hyl), triclopyr-triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate sulfate), vernolate, XDE-848, ZJ-0862 (i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline), 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1-(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid methyl ester, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1-(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo- 4-(trifluoromethyl)-3,6-dihydropyrimidin-1-(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid, 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)isoxazol-5-yl]phenyl 5-chloropyrimidin-2-yl ether, 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazin-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dione,(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-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]-1H-pyrazol-5-ylpropane-1-sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)propane ) pyridine-2-carboxylic acid cyanomethyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) pyridine-2-carboxylic acid prop-2-yn-1-yl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) pyridine-2-carboxylic acid methyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) pyridine-2-carboxylic acid benzyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) pyridine-2-carboxylic acid ethyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) pyridine-2-carboxylic acid methyl ester, 6-(1-acetyl-7 4-amino-3-chloro-5-fluoro-6-[1-(2,2-dimethylpropanoyl)-7-fluoro-1H-indol-6-yl]-5-fluoro-pyridine-2-carboxylic acid methyl ester, 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl] pyridine-2-carboxylic acid methyl ester, 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl] pyridine-2-carboxylic acid methyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) pyridine-2-carboxylic acid potassium, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) pyridine-2-carboxylic acid sodium, 4-amino-3-chloro-5-fluoro-6-(7-fluoro- 1H-indol-6-yl) pyridine-2-carboxylic acid butyl ester, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione,3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin-1-ium salt (with a suitable anion such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-1-ium salt (with a suitable anion such as chloride, acetate or trifluoroacetate), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazin-1- onium salt (having a suitable anion such as chloride, acetate or trifluoroacetate), 4-(pyridazin-3-yl)-1-(2-sulfoethyl)pyridazin-1-ium salt (having a suitable anion such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3-thiazol-2-yl)pyridazin-1-ium salt (having a suitable anion such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3,4-thiadiazol-2-yl)pyridazin-1-ium salt (having a suitable anion such as chloride, acetate or trifluoroacetate), (2R)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)- 3,6-dihydropyrimidin-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoic acid methyl ester, (2S)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoic acid methyl ester, (2R / S)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoic acid methyl ester, (E)-2-(trifluoromethyl)benzaldehyde O-{2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzaldehyde 2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanecarboxylic acid, 2-ethoxy-2-oxoethyl 1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropanecarboxylate, 2-methoxy-2-oxoethyl 1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropanecarboxylate,{[(1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}acetic acid, 2-(2-bromo-4-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}acetic acid, 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylic acid ethyl ester.

[0381] Examples of plant growth regulators as possible admixtures are:

[0382] abscisic acid and related analogs (e.g., (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid, (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid methyl ester, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2 ,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoic acid methyl ester, (2Z,4E)-5-(2-hydroxy-1,3-dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-dienoic acid]), acibenzolar, acibenzolar-S-methyl, S-adenosylhomocysteine, allantoin, 2-aminoethoxyvinylglycine (AVG), aminooxyacetic acid and related esters [e.g. (isopropylidene )aminooxyacetic acid 2-(methoxy)-2-oxoethyl ester, (isopropylidene)aminooxyacetic acid 2-(hexyloxy)-2-oxoethyl ester, (cyclohexylidene)aminooxyacetic acid-2-(isopropyloxy)-2-oxoethyl ester], 1-aminocyclopropane-1-ylcarboxylic acid, N-methyl-1-aminocyclopropyl-1-carboxylic acid, 1-aminocyclopropyl-1-carboxamide, substituted 1-aminocyclopropyl-1-carboxylic acid derivatives described in DE3335514, EP30287, DE2906507 or US5123951, 1-aminocyclopropyl-1-hydroxyamine, 5-aminopyruvic acid, ancymidol, 6-benzylaminopurine (6-benzylaminopurine rine), bikinin, brassinolide, brassinolide-ethyl, L-canaline, catechol and catechols (e.g. (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol), chitooligosaccharides (CO; CO differs from LCO in that they lack the fatty acid side chains characteristic of LCO. CO, also called N-acetylchitooligosaccharides in some cases, is also composed of GlcNAc units, but has a characteristic that allows them to bind to chitin molecules [(C8 H 13 NO 5 ) n , CAS No. 1398-61-4] and chitosan molecules [(C 5 H 11 NO 4 ) n, CAS No. 9012-76-4] different side chains), chitin-like compounds, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozid, dazomet, dazomet-sodium, n-decanol, dikegulac, dikegulac-sodium, endot hal), endothal-dipotassum, endothal-disodium and mono(N,N-dimethylalkylammonium), ethephon, 1-ethylcyclopropene, flumetralin, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, gibberellic acid acid), inabenfid, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolan, probenazole, jasmonic acid, jasmonate or other derivatives (such as methyl jasmonate, ethyl jasmonate), lipochitooligosaccharides (LCO, also sometimes called symbiotic nodulation signal (Nod or Nod factor) or Myc factor, which consists of an oligosaccharide backbone composed of β-l,4-linked N-acetyl-D-glucosamine residues ("GlcNAc") with N-linked fatty acid side chains bound to the non-reducing terminus.As can be deduced from the literature, LCOs differ in: the number of GlcNAc units in the backbone structure, the length and degree of saturation of the fatty acid chains and the substitution of 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, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methylsulfonamide and related substituted (tetrahydroquinolin-6-yl)methylsulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one and related lactones described in EP2248421, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture (nitrophenoxide mixture), 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole, 4-phenylbutyric acid and its salts (e.g. sodium 4-phenylbutyrate, potassium 4-phenylbutyrate), phenylalanine, N-phenyl-o-aminobenzoic acid, prohexadiones, prohexadione-calcium, 1-n-propylcyclopropene, putrescine, prohydrojasmone, rhizobitoxin, salicylic acid, methyl salicylate, sarcosine, sodium cycloprop-1-en-1-yl acetate, sodium cycloprop-2-en-1-yl acetate, sodium 3-(cycloprop-2-en-1-yl) propionate, 3-(cycloprop- sodium 1-en-1-yl)propionate, sidefungin, spermidine, spermines, strigolactones, tecnazenes, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tryptophan, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine, 2-chloro-N-(3-methoxyphenyl)-9H-purin-6-amine.

[0383] Useful combination partners of the compounds of general formula (I) of the present invention also include, for example, the following safeners:

[0384] S1) Compound of formula (S1)

[0385]

[0386] The symbols and subscripts are defined as follows:

[0387] n A A natural number from 0 to 5, preferably from 0 to 3;

[0388] R A 1 For halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, nitro or (C 1 -C 4 )-haloalkyl;

[0389]

[0390] W A is an unsubstituted or substituted divalent heterocyclic group selected from partially unsaturated or aromatic five-membered heterocyclic rings having 1 to 3 heteroatoms selected from N or O, wherein at least one nitrogen atom and at most one oxygen atom are present in the ring, preferably selected from (W A 1 ) to (W A 5 ),

[0391] m A is 0 or 1;

[0392] R A 2 OR A 3 , SR A 3 or NR A 3 R A 4 or a saturated or unsaturated 3- to 7-membered heterocyclic ring having at least one nitrogen atom and up to 3 heteroatoms preferably selected from O and S, said heterocyclic ring being linked to the carbonyl group in (S1) via the nitrogen atom, and said heterocyclic ring being unsubstituted or selected from (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy or optionally substituted phenyl, R A 2 Preferably, the formula is ORA 3 、NHR A 4 or N(CH 3 ) 2 Groups, especially of the formula OR A 3 ;

[0393] R A 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group, preferably having a total of 1 to 18 carbon atoms;

[0394] R A 4 For hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or substituted or unsubstituted phenyl;

[0395] R A 5 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 , where R A 9 For 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;

[0396] R A 6 , R A 7 , R A 8 the same or different and are hydrogen, (C 1 -C8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 3 -C 12 )-cycloalkyl or substituted or unsubstituted phenyl;

[0397] R A 10 H, (C 3 -C 12 )-cycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted heteroaryl;

[0398] Preferably:

[0399] a) Dichlorophenylpyrazoline-3-carboxylic acid compounds (S1 a ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) ("mefenpyr-diethyl") and related compounds as described in WO-A-91 / 07874;

[0400] b) Derivatives of dichlorophenylpyrazole carboxylic acid (S1 b ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid ethyl ester (S1-2), 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylic acid ethyl ester (S1-3), 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylic acid ethyl ester (S1-4) and related compounds, as described in EP-A-333131 and EP-A-269806;

[0401] c) 1,5-diphenylpyrazole-3-carboxylic acid derivatives (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;

[0402] d) Triazole carboxylic acid compounds (S1 d ), preferably compounds such as fenchlorazole (ethyl ester), i.e. 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174562 and EP-A-346620;

[0403] e) 5-benzyl-2-isoxazoline-3-carboxylic acid compounds, 5-phenyl-2-isoxazoline-3-carboxylic acid compounds, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid compounds (S1 e ), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds, as described in WO-A-91 / 08202; or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) ("isoxadifen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13), as described in patent application WO-A-95 / 07897.

[0404] f) Triazolyloxyacetic acid derivatives (S1 f ), preferably compounds such as methyl {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-14) or {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-15) or methyl {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-16) or {[5-(4-chloro-2-fluorophenyl) -1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (S1-17) or {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid methyl ester (S1-18) or {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (S1-19), as described in patent application WO2021105101.

[0405] S2) a quinoline derivative of formula (S2),

[0406]

[0407] The symbols and subscripts are defined as follows:

[0408] R B 1 For halogen, (C 1 -C 4 )-alkyl, (C 1-C 4 )-alkoxy, nitro or (C 1 -C 4 )-haloalkyl;

[0409] n B A natural number from 0 to 5, preferably from 0 to 3;

[0410] R B 2 OR B 3 , SR B 3 or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocyclic ring having at least one nitrogen atom and up to 3 heteroatoms preferably selected from O and S, said heterocyclic ring being linked to the carbonyl group in (S2) via the nitrogen atom, and said heterocyclic ring being unsubstituted or selected from (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy or optionally substituted phenyl, R B 2 Preferably, the formula is OR B 3 、NHR B 4 or N(CH 3 ) 2 Groups, especially of the formula OR B 3 ;

[0411] R B 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group, preferably having a total of 1 to 18 carbon atoms;

[0412] R B 4 For hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or substituted or unsubstituted phenyl;

[0413] T B is unsubstituted or replaced by one or two (C 1 -C 4 )-alkyl groups or [(C 1 -C 3 )-alkoxy]carbonyl substituted (C 1 or C 2 )-alkanediyl chain;

[0414] Preferably:

[0415] a) 8-Quinolinyloxyacetic acid compounds (S2 a ), preferably (5-chloro-8-quinolinyloxy)acetic acid 1-methylhexyl ester ("cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinyloxy)acetic acid 1,3-dimethylbutan-1-yl ester (S2-2), (5-chloro-8-quinolinyloxy)acetic acid 4-allyloxybutyl ester (S2-3), (5-chloro-8-quinolinyloxy)acetic acid 1-allyloxypropan-2-yl ester (S2-4), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-5), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-6), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-7), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-8), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-9), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-10), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-11), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-12), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-13), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-14), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-15), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-16), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-17), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-18), (5-chloro-8 S2-5), methyl (5-chloro-8-quinolinyloxy)acetate (S2-6), allyl (5-chloro-8-quinolinyloxy)acetate (S2-7), 2-(2-propyleneiminooxy)-1-ethyl (5-chloro-8-quinolinyloxy)acetate (S2-8), 2-oxopropan-1-yl (5-chloro-8-quinolinyloxy)acetate (S2-9) and related compounds, as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492366; and (5-chloro-8-quinolinyloxy)acetic acid (S2-10), hydrates and salts thereof, for example, lithium salts, sodium salts, potassium salts, calcium salts, magnesium salts, aluminum salts, iron salts, ammonium salts, quaternary ammonium salts, sulfonium salts or phosphonium salts thereof, as described in WO-A-2002 / 34048;

[0416] b) (5-chloro-8-quinolinyloxy)malonic acid compounds (S2 b ), preferably compounds such as diethyl (5-chloro-8-quinolyloxy)malonate, diallyl (5-chloro-8-quinolyloxy)malonate, methyl ethyl (5-chloro-8-quinolyloxy)malonate and related compounds as described in EP-A-0 582 198.

[0417] S3) Compound of formula (S3)

[0418]

[0419] The symbols and subscripts are defined as follows:

[0420] R C 1 For (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C3 -C 7 )-cycloalkyl, preferably dichloromethyl;

[0421] R C 2 , R C 3 the same 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, furanyl, furanylalkyl, thienyl, piperidinyl, substituted or unsubstituted phenyl, or R C 2 and R C 3Together they form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; preferably: an active ingredient of the dichloroacetamide class, which is often used as a pre-emergence safener (a safener acting on the soil), such as "dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2) from Stauffer, "R-28725" (3-dichloroacetyl-2,2,-dimethyl-1,3-oxazolidine) (S3-3) from Stauffer, "benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), available from PPG Industries, “PPG-1292” (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) (S3-5), purchased from Sagro-Chem, “DKA-24” (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6), purchased from Nitrokemia or Monsanto, “AD-67” or “MON4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4,5]decane) (S3-7), purchased from TRI-Chemical "TI-35" (1-dichloroacetylazepane) (S3-8) from RT, "diclonon" (dicyclonon) or "BAS145138" or "LAB145138" (S3-9) ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) purchased from BASF, "furilazole" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10) and its (R) isomer (S3-11).

[0422] S4) N-acylsulfonamide of formula (S4) and its salt,

[0423]

[0424] The symbols and subscripts are defined as follows:

[0425] X D is CH or N;

[0426] R D 1 For CO-NR D 5 R D6 or NHCO-R D 7 ;

[0427] R D 2 For 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;

[0428] R D 3 For hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl or (C 2 -C 4 )-alkynyl;

[0429] R D 4 For 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;

[0430] R D5 For 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 a V-containing radical selected from nitrogen, oxygen and sulfur D 3 to 6 membered heterocyclic group containing 4 heteroatoms, wherein the last seven groups are replaced by v D Substituents are substituted, said v D The substituents are selected from 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 a cyclic group, may also be selected from (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl;

[0431] R D 6 For hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl, in which the last three groups are replaced by v D The v D A group is selected from halogen, hydroxyl, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and (C 1 -C 4 )-alkylthio, or

[0432] R D5 and R D 6 Together with the nitrogen atom that carries them, they form a pyrrolidinyl or piperidinyl group;

[0433] R D 7 For hydrogen, (C 1 -C 4 )-alkylamino, di(C 1 -C 4 )-alkylamino, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, wherein the last two groups are v D Substituents are substituted, said v D The substituents are selected from halogen, (C 1 -C 4 )-alkoxy, (C 1 -C 6 )-haloalkoxy and (C 1 -C 4 )-alkylthio, and in the case of a cyclic group, may also be selected from (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl;

[0434] n D is 0, 1, or 2;

[0435] m D is 1 or 2;

[0436] v D is 0, 1, 2, or 3;

[0437] Among them, N-acylsulfonamide compounds are preferred, such as the following formula (S4 a ), which is known from, for example, WO-A-97 / 45016.

[0438]

[0439] in

[0440] R D 7 For (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, wherein the last two groups are v D Substituents are substituted, said v D The substituents are selected from halogen, (C1 -C 4 )-alkoxy, (C 1 -C 6 )-haloalkoxy and (C 1 -C 4 )-alkylthio, and in the case of a cyclic group, further selected from (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl;

[0441] R D 4 For halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, CF 3 ;

[0442] m D is 1 or 2;

[0443] v D is 0, 1, 2, or 3;

[0444] Also preferred are acylaminosulfonylbenzamides, for example, those of the formula (S4 b ), which is known, for example, from WO-A-99 / 16744,

[0445]

[0446] For example,

[0447] R D 5 = cyclopropyl, (R D 4 )=2-OMe("cyprosulfamide", S4-1),

[0448] R D 5 = cyclopropyl, (R D 4 )=5-Cl-2-OMe(S4-2),

[0449] R D 5 =ethyl, (R D 4 )=2-OMe(S4-3),

[0450] R D 5 = isopropyl, (R D 4)=5-Cl-2-OMe(S4-4), and

[0451] R D 5 = isopropyl, (R D 4 )=2-OMe(S4-5),

[0452] And preferably N-acylaminosulfonylphenyl urea compounds, such as formula (S4 c ), which is known, for example, from EP-A-365484,

[0453]

[0454] in

[0455] R D 8 and R D 9 are independently hydrogen, (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl,

[0456] R D 4 For halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, CF 3 ,

[0457] m D is 1 or 2;

[0458] For example

[0459] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,

[0460] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0461] 1-[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylurea.

[0462] S5) Active ingredients (S5) of the class of hydroxyaromatic compounds and aromatic-aliphatic carboxylic acid derivatives, for example ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001.

[0463] S6) Active ingredients of the 1,2-dihydroquinoxaline-2-one class (S6), for example 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one, as described in WO-A-2005 / 112630.

[0464] S7) A compound of formula (S7), as described in WO-A-1998 / 38856,

[0465]

[0466] The symbols and subscripts are defined as follows:

[0467] R E 1 , R E 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;

[0468] A E For COOR E 3 or COSR E 4 .

[0469] R E 3 , R E 4 are 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, pyridylalkyl and alkylammonium,

[0470] n E 1 0 or 1

[0471] n E 2 、n E 3 are independently 0, 1 or 2,

[0472] Preferred are diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, and methyl diphenylmethoxyacetate (CAS Registry No. 41858-19-9) (S7-1).

[0473] S8) A compound of formula (S8), as described in WO-A-98 / 27049,

[0474]

[0475] in

[0476] X F is CH or N,

[0477] n F In X F =N is an integer from 0 to 4, and

[0478] In X F =CH is an integer from 0 to 5,

[0479] 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, nitro, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 4)-alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy,

[0480] R F 2 is hydrogen or (C 1 -C 4 )-alkyl,

[0481] R F 3 For hydrogen, (C 1 -C 8 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl or aryl, wherein each of the above carbon-containing groups is unsubstituted or substituted by one or more, preferably up to three, identical or different groups selected from halogen and alkoxy; or a salt thereof,

[0482] Preferred are compounds in which

[0483] X F For CH,

[0484] n F is an integer from 0 to 2,

[0485] R F 1 For halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy,

[0486] R F 2 is hydrogen or (C 1 -C 4 )-alkyl,

[0487] R F 3 For hydrogen, (C 1 -C 8 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl or aryl, wherein each of the above carbon-containing groups is unsubstituted or substituted by one or more, preferably up to three, identical or different groups selected from halogen and alkoxy, or a salt thereof.

[0488] S9) Active ingredients of the 3-(5-tetrazolylcarbonyl)-2-quinolone class (S9), for example 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.

[0489] S10 a ) or (S10 b ),

[0490] As described in WO-A-2007 / 023719 and WO-A-2007 / 023764,

[0491]

[0492] in

[0493] R G 1 For halogen, (C 1 -C 4 )-alkyl, methoxy, nitro, cyano, CF 3 、OCF 3 ,

[0494] Y G , Z G represent O or S independently of each other,

[0495] n G is an integer from 0 to 4,

[0496] R G 2 For (C 1 -C 16 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-cycloalkyl, aryl; benzyl, halogenated benzyl,

[0497] R G 3 is hydrogen or (C 1 -C 6 )-alkyl.

[0498] S11) Active ingredients of the class of oxyimino compounds (S11), which are known as seed dressing ingredients, for example "oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet / sorghum against damage by isopropylamine, "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 to resist isopropylamine damage, and "cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet / sorghum to resist isopropylamine damage.

[0499] S12) Active ingredients of isothiochromanones (S12), for example [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetic acid methyl ester (CAS Reg. No. 205121-04-6) (S12-1) and related compounds in WO-A-1998 / 13361.

[0500] One or more compounds of group (S13) of S13: "naphthalic anhydride" (1,8-naphthalic anhydride) (S13-1), which is known as a seed dressing safener for corn against damage by thiocarbamate herbicides, "fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice, "flurazole" (2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylic acid benzyl ester) (S13-3), which is known as a seed dressing safener for millet against damage by alachlor and isopropylamine, available from American Cyanamid's "CL-304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4), which is known as a safener for corn against damage by imidazolinones, was purchased from Nitrokemia's "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5), which is known as a safener for corn, "MG-838" (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-dithiocarbamate) (S13-6), "disulfoton" (S-2-ethylthioethyl dithiophosphoric acid O,O-diethyl ester) (S13-7), "dietholate" (O-phenylthiophosphoric acid O,O-diethyl ester) (S13-8), "mephenate" (methylcarbamic acid 4-chlorophenyl ester) (S13-9).

[0501] S14) Active ingredients which, in addition to their herbicidal action on harmful plants, also have a safener effect on crop plants such as rice, for example "dimepiperate" or "MY-93" (S-1-methyl 1-phenylethylpiperidine-1-thiocarboxylate), which is known as a safener for rice against damage by the herbicide cypermethrin, "methoxyphenon" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide pyrazosulfuron-methyl, "benzylpyruvate" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), which is known as a safener for rice against damage by some herbicides, "methoxyphenon" or "NK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide pyrazosulfuron-methyl, 049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for use in rice against damage by some herbicides, and "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) (CAS Reg. No. 54091-06-4), available from Kumiai, which is known as a safener for use in rice against damage by some herbicides.

[0502] S15) A compound of formula (S15) or a tautomer thereof

[0503] As described in WO-A-2008 / 131861 and WO-A-2008 / 131860,

[0504]

[0505] in

[0506] R H 1 For (C 1 -C 6 )-haloalkyl, and

[0507] R H 2 is hydrogen or a halogen, and

[0508] R H 3 , R H 4 are independently hydrogen, (C 1 -C 16 )-alkyl, (C 2 -C 16 )-alkenyl or (C 2 -C 16 )-alkynyl, wherein each of the last three groups is unsubstituted or substituted by one or more groups selected from the group consisting of halogen, hydroxy, cyano, (C 1 -C4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylamino, bis[(C 1 -C 4 )-alkyl]amino, [(C 1 -C 4 )-alkoxy]carbonyl, [(C 1 -C 4 )haloalkoxy]carbonyl, unsubstituted or substituted (C 3 -C 6 )-cycloalkyl, unsubstituted or substituted phenyl, and unsubstituted or substituted heterocyclic group, or (C 3 -C 6 )-cycloalkyl, (C 4 -C 6 )-cycloalkenyl, (C 3 -C 6 )-cycloalkyl fused on one side to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 )cycloalkenyl fused on one side to a 4- to 6-membered saturated or unsaturated carbocyclic ring, wherein each of the latter four groups is unsubstituted or substituted by one or more groups selected from: 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, bis[(C 1 -C 4 )-alkyl]amino, [(C 1 -C 4 )-alkoxy]carbonyl, [(C 1 -C 4 )-haloalkoxy]carbonyl, unsubstituted or substituted (C 3 -C 6 )-cycloalkyl, unsubstituted or substituted phenyl, and unsubstituted or substituted heterocyclic group,

[0509] or

[0510] R H 3 For (C 1 -C 4 )-alkoxy, (C 2 -C 4 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy or (C 2 -C 4 )-Haloalkoxy

[0511] and

[0512] R H 4 is hydrogen or (C 1 -C 4 )-alkyl, or

[0513] R H 3 and R H 4 Together with the directly bonded nitrogen atom, it is a four- to eight-membered heterocyclic ring which, in addition to the nitrogen atom, may contain further ring heteroatoms, preferably up to two further ring heteroatoms selected from N, O and S, and which is unsubstituted or substituted by one or more groups selected from the group consisting of halogen, cyano, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy and (C 1 -C 4 )-alkylthio.

[0514] S16) Active ingredients that are mainly used as herbicides but also have a safener effect on crop plants, such as (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (2-methyl-4-chloropropionic acid), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 3,6-dichloro-2-methoxybenzoic acid 1-(ethoxycarbonyl)ethyl ester (lactidichlor-ethyl).

[0515] Biological Examples:

[0516] A. Post-emergence herbicidal action and crop compatibility of selected compounds of general formula (I)

[0517] Seeds of monocotyledonous and dicotyledonous weeds and crop plants are placed in sandy loam in plastic pots or wood fiber pots, covered with soil and cultivated in a greenhouse under controlled growth conditions. The test plants are treated 2 to 3 weeks after sowing, at the one-leaf stage. The compounds of the invention formulated as wettable powders (WP) or emulsion concentrates (EC) are then sprayed onto the green parts of the plants as aqueous suspensions or emulsions at a water application rate of 600 l / ha (converted value) and with the addition of 0.5% additives. After the test plants have been kept in a greenhouse under optimal growth conditions for about 3 weeks, the activity of the preparations is visually assessed in comparison with an untreated control group. For example, 100% activity = plant has died, 0% activity = similar to the control plants.

[0518] Tables A1 to A13 below show the effects of selected compounds of the general formula (I) from Tables I.1 to I.33 on various harmful plants and the corresponding application rates of 20 g / ha and lower, which were obtained by the above-specified test method.

[0519] The suffixes "a", "b" and "c" distinguish between different doses used on the same harmful plant species tested.

[0520] Table A1a: Post-emergence efficacy in % against ABUTH at 1.25 g / ha

[0521]

[0522] Table A1b: Post-emergence efficacy in % against ABUTH at 5 g / ha

[0523]

[0524]

[0525] Table A1c: Post-emergence efficacy in % against ABUTH at 20 g / ha

[0526] Table A2a: Post-emergence efficacy in % against ALOMY at 1.25 g / ha

[0527] Table A2b: Post-emergence efficacy in % against ALOMY at 5 g / ha

[0528]

[0529] Table A2c: Post-emergence efficacy in % against ALOMY at 20 g / ha

[0530]

[0531] Table A3a: Post-emergence efficacy in % on AMARE at 1.25 g / ha

[0532]

[0533]

[0534] Table A3b: Post-emergence efficacy in % on AMARE at 5 g / ha

[0535]

[0536] Table A3c: Post-emergence efficacy in % on AMARE at 20 g / ha

[0537]

[0538]

[0539] Table A4a: Post-emergence efficacy in % against ECHCG at 1.25 g / ha

[0540]

[0541] Table A4b: Post-emergence efficacy in % against ECHCG at 5 g / ha

[0542]

[0543]

[0544] Table A4c: Post-emergence efficacy in % against ECHCG at 20 g / ha

[0545] Table A5a: Post-emergence efficacy in % against LOLRI at 20 g / ha

[0546] Table A6a: Post-emergence efficacy in % on MATIN at 1.25 g / ha

[0547] Table A6b: Post-emergence efficacy in % on MATIN at 5 g / ha

[0548] Table A6c: Post-emergence efficacy in % on MATIN at 20 g / ha

[0549]

[0550] Table A7a: Post-emergence efficacy in % against PHBPU at 1.25 g / ha

[0551]

[0552] Table A7b: Post-emergence efficacy in % on PHBPU at 5 g / ha

[0553]

[0554] Table A7c: Post-emergence efficacy in % on PHBPU at 20 g / ha

[0555]

[0556] Table 8a: Post-emergence efficacy in % against POLCO at 1.25 g / ha

[0557]

[0558] Table A8b: Post-emergence efficacy in % against POLCO at 5 g / ha

[0559]

[0560] Table A8c: Post-emergence efficacy in % against POLCO at 20 g / ha

[0561]

[0562]

[0563] Table A9a: Post-emergence efficacy in % against SETVI at 1.25 g / ha

[0564]

[0565] Table A9b: Post-emergence efficacy in % against SETVI at 5 g / ha

[0566]

[0567]

[0568] Table A9c: Post-emergence efficacy in % against SETVI at 20 g / ha

[0569] Table A10a: Post-emergence efficacy in % against VERPE at 1.25 g / ha

[0570]

[0571] Table A10b: Post-emergence efficacy in % against VERPE at 5 g / ha

[0572]

[0573] Table A10c: Post-emergence efficacy in % against VERPE at 20 g / ha

[0574]

[0575]

[0576] Table A11a: Post-emergence efficacy in % against VIOTR at 1.25 g / ha

[0577]

[0578] Table A11b: Post-emergence efficacy in % against VIOTR at 5 g / ha

[0579]

[0580]

[0581] Table A11c: Post-emergence efficacy in % against VIOTR at 20 g / ha

[0582]

[0583] Table A12a: Post-emergence efficacy in % against DIGSA at 1.25 g / ha

[0584]

[0585] Table A12b: Post-emergence efficacy in % against DIGSA at 5 g / ha

[0586]

[0587]

[0588] Table A12c: Post-emergence efficacy in % against DIGSA at 20 g / ha

[0589]

[0590] Table A13a: Post-emergence efficacy in % against KCHSC at 1.25 g / ha

[0591]

[0592]

[0593] Table A13b: Post-emergence efficacy in % against KCHSC at 5 g / ha

[0594]

[0595] Table A13c: Post-emergence efficacy in % against KCHSC at 20 g / ha

[0596]

[0597]

[0598] Tables A14 to A17 below show the crop plant compatibility of selected compounds of the general formula (I) from Tables I.1 to I.33 at application rates corresponding to 20 g / ha or less, the effects being observed in tests carrying out the above-described experimental procedure.

[0599] The observed effects on the selected crop plants are reported here in comparison with untreated controls (values ​​in %).

[0600] The suffixes "a", "b" and "c" distinguish between different doses used on the same crop plants tested.

[0601] Table A14a: Post-emergence efficacy in % against ZEAMX at 1.25 g / ha

[0602]

[0603] Table A14b: Post-emergence efficacy in % against ZEAMX at 5 g / ha

[0604]

[0605] Table A15a: Post-emergence efficacy in % against TRZAS at 1.25 g / ha

[0606]

[0607]

[0608] Table A15b: Post-emergence efficacy in % against TRZAS at 20 g / ha

[0609] Table A16a: Post-emergence efficacy in % against ORYSA at 1.25 g / ha

[0610] Table A16b: Post-emergence efficacy in % against ORYSA at 5 g / ha

[0611] Table A16c: Post-emergence efficacy in % against ORYSA at 20 g / ha

[0612]

[0613] Table A17a: Post-emergence efficacy in % against GLXMA at 1.25 g / ha

[0614]

[0615] As shown in these results, the compounds of the general formula (I) of the present invention have good herbicidal efficacy against harmful plants such as Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Bassia scoparia (KCHSC), Lolium rigidum (LOLRI), Tripleurospermuminodorum (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Veronica officinalis (VITVI), and Echinochloa crus-galli (ECHCG). persica)(VERPE) and pansy (Violatricolor) (VIOTR), and (b) at application rates of 0.02 kg per hectare and below, it has good crop compatibility with organisms such as rice (Oryza sativa) (ORYSA), maize (Zea mays) (ZEAMX), soybean (Glycinemax) (GLXMA) and wheat (Triticum aestivum) (TRZAS).

[0616] B. Post-emergence herbicidal action and crop plant compatibility of selected compounds according to the invention (I.7-12, I.7-14, I.7-16) in comparison with structurally similar compounds known from the literature (WO 2002 / 098227, structures "a-27" and "a-29").

[0617] The following Tables B1-B5 show the efficacy of the compounds of the present invention (I.7-12, I.7-14, I.7-16) obtained by the above-mentioned specified test method compared with the structurally similar compounds known from the literature ("a-27", "a-29" disclosed in WO2002 / 098227), at an application rate corresponding to 20 g / ha or less, against various harmful plants.

[0618] In this case, the tested compounds of the invention (I.7-12, I.7-14, I.7-16) each have a significant structural feature in the ester unit that is different from the compounds known in the literature, which is achieved by introducing a methylene bridge (-CH 2 -) while having the same "cycloalkyl group".

[0619] Table B1

[0620]

[0621] Table B2

[0622]

[0623] Table B3

[0624]

[0625] Table B4

[0626]

[0627]

[0628] Table B5

[0629]

[0630] As shown in the results shown in Tables B1 to B5, the compounds I.7-12, I.7-14, I.7-16 of the present invention show significantly improved herbicidal efficacy against harmful plants, such as Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Avena fatura (AVEFA), Veronica persica (VERPE), at an application rate of 20 g per hectare or less, compared to the structurally similar compounds "a-27", "a-29" known in the literature (WO 2002 / 098227) or the structures generally covered in the literature.

[0631] Tables B6-B10 below show the efficacy of the compounds of the invention (I.7-12, I.7-14, I.7-16) obtained by the above-mentioned specified test method in comparison with structurally similar compounds known from the literature ("a-27", "a-29" disclosed in WO2002 / 098227), at application rates corresponding to 5 g / ha or less on the crop plants Oryza sativa (ORYSA), maize (Zea mays) (ZEAMX) and wheat (Triticum aestivum) (TRZAS).

[0632] Table B6

[0633]

[0634] Table B7

[0635]

[0636] Table B8

[0637]

[0638] Table B9

[0639]

[0640]

[0641] Table B10

[0642]

[0643] As shown in the results shown in Tables B6 to B10, the compounds of the present invention (I.7-12, I.7-14, I.7-16) are directly compared with the structurally similar compounds "a-27", "a-29" known in the literature (WO2002 / 098227) or the structures generally covered in the literature, and show significantly improved compatibility with the crop plants rice (Oryza sativa) (ORYSA), maize (Zea mays) (ZEAMX) and wheat (Triticum aestivum) (TRZAS) at an application rate of 5 g per hectare or less.

Claims

1. Substituted N-phenyluracil of formula (I) or its salt in 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 Halogen, cyano, NO 2 、C(O)NH 2 、C(S)NH 2 , (C 1 -C 8 )-haloalkyl or (C 2 -C 8 )-alkynyl, R 5 , R 6 and R 7 are independently hydrogen, halogen, cyano, (C 1 -C 8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 1 -C 8 )-alkoxy or (C 1 -C 8 )-haloalkoxy, G is unbranched or branched (C 1 -C 8 )-alkylene, Q is a group of the formula R 8 For hydrogen, (C 1 -C 8 )-alkyl or cyano, R 9 is hydrogen or (C 1 -C 8 )-alkyl, R 10 is unsubstituted or substituted independently in each case by "m" groups (C 3 -C 8 )-cycloalkyl, the "m" groups are selected from 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 is unsubstituted or substituted independently in each case by "m" groups of spiro-(C 5 -C 9 )-alkyl or dispiro-(C 7 -C 8 )-alkyl, wherein the "m" groups are selected from 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 as well as X and Y are independently O (oxygen) or S (sulfur).

2. The compound of formula (I) and / or its salt according to claim 1, Features 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 Halogen, cyano, NO 2 、C(O)NH 2 、C(S)NH 2 , (C 1 -C 6 )-haloalkyl or (C 2 -C 6 )-alkynyl, R 5 , R 6 and R 7 are independently hydrogen, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy or (C 1 -C 6 )-haloalkoxy, G is unbranched or branched (C 1 -C 6 )-alkylene, Q is a group of the formula R 8 For hydrogen, (C 1 -C 6 )-alkyl or cyano, R 9 is hydrogen or (C 1 -C 6 )-alkyl, R 10 is unsubstituted or substituted independently in each case by "m" groups (C 3 -C 7 )-cycloalkyl, the "m" groups are selected from 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 and nitro, or is unsubstituted or substituted independently in each case by "m" groups of spiro-(C 5 -C 7 )-alkyl or dispiro-(C 7 -C 8 )-alkyl, wherein the "m" groups are selected from halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, m is 0, 1, 2, or 3 as well as X and Y are independently O (oxygen) or S (sulfur).

3. The compound of formula (I) and / or its salt according to claim 1, Features R 1 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, propan-1-yl, 1-methylethyl, butan-1-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3 -dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, R 2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, propan-1-yloxy, but-1-yloxy, R 3 is hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, propan-1-yloxy, propan-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylpropan-1-yloxy, 1,1-dimethyleth-1-yloxy, R 4 Fluorine, chlorine, bromine, cyano, NO 2 、C(O)NH 2 、C(S)NH 2 , trifluoromethyl, difluoromethyl, pentafluoroethyl, ethynyl, propyn-1-yl, 1-butyn-1-yl, pentyn-1-yl, hexyn-1-yl, R 5 , R 6 and R 7 and 1-ethylpropyl, 1-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, G is methylene, (methyl)methylene, (ethyl)methylene, (prop-1-yl)methylene, (prop-2-yl)methylene, (but-1-yl)methylene, (but-2-yl)methylene, (pent-1-yl)methylene, (pent-2-yl)methylene, (pent-3-yl)methylene, (dimethyl)methylene, (diethyl)methylene, ethylene, n-propylene, (1-methyl)ethylene-1-yl, (2-methyl)ethylene-1-yl, n-butylene, 1-methylpropylene-1-yl, 2-methylpropylene- 1-yl, 3-methylpropylene-1-yl, 1,1-dimethylethylene-1-yl, 2,2-dimethylethylene-1-yl, 1-ethylethylene-1-yl, 2-ethylethylene-1-yl, 1-(propylene-1-yl)ethylene-1-yl, 2-(propylene-1-yl)ethylene-1-yl, 1-(propylene-2-yl)ethylene-1-yl, 2-(propylene-2-yl)ethylene-1-yl, 1,1,2-trimethylethylene-1-yl, 1,2,2-trimethylethylene-1-yl, 1,1,2,2-tetramethylethylene-1 -yl, n-pentylene, 1-methylbutylene-1-yl, 2-methylbutylene-1-yl, 3-methylbutylene-1-yl, 4-methylbutylene-1-yl, 1,1-dimethylpropylene-1-yl, 2,2-dimethylpropylene-1-yl, 3,3-dimethylpropylene-1-yl, 1,2-dimethylpropylene-1-yl, 1,3-dimethylpropylene-1-yl, 1-ethylpropylene-1-yl, n-hexylene, 1-methylpentylene-1-yl, 2-methylpentylene-1-yl, 3-methylpentylene-1-yl, 4-methylbutylene-1-yl, pentan-1-yl, 1,1-dimethylbutan-1-yl, 1,2-dimethylbutan-1-yl, 1,3-dimethylbutan-1-yl, 2,2-dimethylbutan-1-yl, 2,3-dimethylbutan-1-yl, 3,3-dimethylbutan-1-yl, 1-ethylbutan-1-yl, 2-ethylbutan-1-yl, 1,1,2-trimethylpropylene-1-yl, 1,2,2-trimethylpropylene-1-yl, 1-ethyl-1-methylpropylene-1-yl, 1-ethyl-2-methylpropylene-1-yl, X and Y are independently O (oxygen) or S (sulfur) as well as Q is one of the groups Q-1 to Q-25 specifically mentioned below, wherein the arrows in the structural formulas in the following table represent the bond connecting each Q group to the carbonyl group in formula (I), 4. The compound of formula (I) and / or its salt according to claim 1, Features 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 Fluorine, chlorine, bromine, cyano, NO 2 、C(O)NH 2 、C(S)NH 2 , trifluoromethyl, ethynyl or propyn-1-yl, R 5 , R 6 and R 7 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethylene-1-yl, (2-methyl)ethylene-1-yl, n-butylene, 1-methylpropylene-1-yl, 2-methylpropylene-1-yl, 3-methylpropylene-1-yl, 1,1-dimethylethylene-1-yl, 2,2-dimethylethylene-1-yl, 1-ethylethylene-1-yl, 2-ethylethylene-1-yl, 1-(propylene-1-yl)ethylene-1-yl, 2-(propylene-1-yl)ethylene-1-yl, 1-(propyl-2-yl)ethylene-1-yl, 1-(propyl-2-yl)ethylene-1-yl, 2-(propyl-2-yl)ethylene-1-yl, n-pentylene, 1-methylbutylene-1-yl, 2-methylbutylene-1-yl, 3-methylbutylene-1-yl, 4-methylbutylene-1-yl, 1,1-dimethylpropylene-1-yl, 2,2-dimethylpropylene-1-yl, 3,3-dimethylpropylene-1-yl, 1,2-dimethylpropylene-1-yl, 1,3-dimethylpropylene-1-yl, 1-ethylpropylene-1-yl or n-hexylene, X and Y are independently O (oxygen) or S (sulfur) as well as Q is one of the groups Q-1 to Q-25 specifically mentioned in claim 3.

5. The compound of formula (I) and / or its salt according to claim 1, Features R 1 is hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, R 2 For fluorine, R 3 For fluorine, R 4 For chlorine, bromine, cyano, NO 2 、C(O)NH 2 or C(S)NH 2 , R 5 , R 6 and R 7 are independently hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethylene-1-yl, (2-methyl)ethylene-1-yl, n-butylene, 1-methylpropylene-1-yl, 2-methylpropylene-1-yl, 3-methylpropylene-1-yl, n-pentylene or n-hexylene, X and Y are independently O (oxygen) or S (sulfur) as well as Q is one of the groups Q-1 to Q-25 specifically mentioned in claim 3.

6. The compound of formula (I) and / or its salt according to claim 1, Features R 1 is hydrogen, fluorine, chlorine or bromine, R 2 For fluorine, R 3 For fluorine, R 4 Chloro, bromo, 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 are independently O (oxygen) or S (sulfur) as well as Q is one of the groups Q-1 to Q-25 specifically mentioned in claim 3.

7. The compound of formula (I) and / or its salt according to claim 1, Features R 1 For hydrogen, R 2 For fluorine, R 3 For fluorine, R 4 Chloro, bromo, cyano or NO 2 , R 5 For hydrogen, R 6 For hydrogen, fluorine, chlorine, R 7 For hydrogen, G is methylene, (methyl)methylene, X is O (oxygen) or S (sulfur), Y is O (oxygen) as well as Q is one of the groups Q-1 to Q-25 specifically mentioned in claim 3.

8. The compound of formula (I) and / or its salt according to claim 1, Features R 1 For hydrogen, R 2 For fluorine, R 3 For fluorine, R 4 is chlorine, bromine or cyano, R 5 For hydrogen, R 6 is hydrogen or fluorine, R 7 For hydrogen, G is a methylene group, X is O (oxygen), Y is O (oxygen) as well as Q represents 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 formula (I) as defined in any one of claims 1 to 8 and / or their salts as herbicides and / or plant growth regulators, preferably in crops of useful and / or ornamental plants.

10. Herbicidal compositions and / or plant growth regulating compositions, It is characterized in that The composition comprises one or more compounds of formula (I) as defined in any one of claims 1 to 8 and / or their salts, and one or more other substances selected from group (i) and / or (ii), including (i) one or more further agrochemical active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, other herbicides, fungicides, safeners, fertilizers and / or other growth regulators, (ii) one or more formulation auxiliaries customary in crop protection.

11. Methods for controlling harmful plants or regulating plant growth, It is characterized in that The effective amount - one or more compounds of formula (I) as defined in any one of claims 1 to 8 and / or their salts, or - The composition according to claim 10, Application to plants, plant seeds, soil or cultivation area in or on which plants are growing.

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