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

Abstract

The present invention relates to substituted N-phenyluracils and their salts and their use as herbicides. [Formula 1] TIFF2023539226000366.tif61170 wherein the radicals in general formula (I) are according to the definitions given herein, or salts thereof, and their use, in particular as herbicides for controlling broadleaf weeds and / or weeds in crops of useful plants and / or as plant growth regulators for influencing the growth of crops of useful plants.

Description

[Technical Field]

[0001] The present invention relates to the technical field of crop protection agents, in particular to the technical field of herbicides for the selective control of broadleaf weeds and weeds in crops of useful plants.

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

[0003] In these applications, the crop protection agents known to date for selectively controlling harmful plants in useful plant crops or active ingredients for controlling undesirable vegetation sometimes have drawbacks, such as (a) no herbicidal activity or only insufficient herbicidal activity against specific harmful plants, (b) the range of harmful plants that can be controlled using active ingredients is not wide enough, (c) their selectivity in useful plant crops is too low, and / or (d) they have an undesirable toxicological profile.In addition, some active ingredients that can be used as plant growth regulators for some useful plants undesirably reduce the yield of other useful plants, or even if they do, they are only compatible with crops within a narrow application range.Some known active ingredients cannot be produced economically on an industrial scale due to the difficult-to-obtain precursors and reagents, or have insufficient chemical stability.For other active ingredients, their activity is too dependent on environmental conditions, such as weather and soil conditions.

[0004] In particular, the herbicidal action of these known compounds at low application rates and / or their compatibility with crops remains in need of improvement.

[0005] It is known from various documents that certain substituted N-linked aryluracils can be used as active herbicidal ingredients (EP 1106607, EP 408382, EP 473551, EP 648749, U.S. Pat. No. 4943309, U.S. Pat. No. 5084084, U.S. Pat. No. 5127935, U.S. Pat. No. 6537948, JP 2001-348376, JP 2001-354661, JP 2002-003480, JP 2002-363010, JP 2002-363170, WO 99 / 04404 ... (See WO 1 / 00278, WO 95 / 29168, WO 95 / 30661, WO 96 / 35679, WO 97 / 01541, WO 98 / 25909, WO 2001 / 034575, WO 2001 / 39597, WO 2001 / 85907, WO 2002 / 098227, WO 2002 / 098228, WO 2003 / 028462, WO 2003 / 028463, WO 2003 / 0284647, WO 2016 / 095768.) However, known aryluracils have some activity gaps, particularly with respect to monocotyledonous weeds. Several combinations of active herbicidal ingredients based on N-linked aryluracils are also known (see German Patent Application Publication No. 4437197, European Patent No. 714602, International Publication No. WO 96 / 07323, International Publication No. WO 96 / 08151, Japanese Patent Application Laid-Open No. 11-189506, Japanese Patent Application Laid-Open No. 2003-104808, Japanese Patent Application Laid-Open No. 2003-104809, Japanese Patent Application Laid-Open No. 2003-104810, Japanese Patent Application Laid-Open No. 2003-160415, and Japanese Patent Application Laid-Open No. 2003-160416). However, the properties of these active ingredient combinations are not always satisfactory.

[0006] Substituted uracils bearing N-linked and further substituted diaryl ester groups or corresponding heteroaryl ether radicals are also known (see U.S. Pat. No. 6,333,296, U.S. Pat. No. 6,121,201, WO 2001 / 85907, EP 1,122,244, EP 1,397,958, EP 1,422,227, and WO 2002 / 098,227). Furthermore, highly substituted N-phenyluracils bearing carbonylalkyloxy groups containing specific substituents have been described (see WO 2011 / 137088). WO 2018 / 019842 describes the use of specifically substituted N-phenyluracils to control specific dicotyledonous weeds with demonstrated specific resistance to herbicides. Substituted 3-phenyl-5-alkyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-diones (see WO 2019 / 101551) are likewise known. Summary of the Invention [Problem to be solved by the invention]

[0007] Surprisingly, selected substituted N-phenyluracils or salts thereof having a substituted alkyl ester side chain are highly suitable as herbicides and can be used with particular advantage as active ingredients for controlling monocotyledonous and dicotyledonous weeds in crops of useful plants. [Means for solving the problem]

[0008] Thus, the present invention provides compounds of general formula (I):

[0009] [ka]

[0010] In the formula (I), a substituted N-phenyluracil of the formula: R 1is hydrogen, halogen, cyano, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, R 2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (C1-C8)-alkoxy, R 3 is hydrogen, halogen, or (C1-C8)-alkoxy; R 4 is halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C8)-haloalkyl, (C2-C8)-alkynyl, R 5 , R 6 and R 7 are independently hydrogen, halogen, cyano, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, G is unbranched or branched (C1-C8)-alkylene; Q is a group having the formula:

[0011] [ka]

[0012] is a radical of R 8 is hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, aryl, aryl-(C1-C8)-alkyl, heteroaryl, (C2-C8)-alkynyl, (C2-C8)-alkenyl, C(O)R 13 , C(O)OR 13 , (C1-C8)-alkoxy-(C1-C8)-alkyl, R 9 is hydrogen or (C1-C8)-alkyl, R 10 is cyano, NO2, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl, R 11 R12 N-(C1-C8)-alkyl, R 13 O-(C1-C8)-alkyl, cyano-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyloxy-(C1-C8)-alkyl, (C3-C8)-cycloalkylcarbonyloxy-(C1-C8)-alkyl, arylcarbonyloxy-(C1-C8)-alkyl, heteroarylcarbonyloxy-(C1-C8)-alkyl, heterocyclylcarbonyloxy-(C1-C8)-alkyl, OR 13 , N.R. 11 R 12 , S.R. 14 , S(O)R 14 , SO2R 14 , R 14 S-(C1-C8)-alkyl, R 14 (O)S-(C1-C8)-alkyl, R 14 OS-(C1-C8)-alkyl, tris[(C1-C8)-alkyl]silyl-(C1-C8)-alkyl, bis[(C1-C8)-alkyl](aryl)silyl(C1-C8)-alkyl, [(C1-C8)-alkyl]bis(aryl)silyl-(C1-C8)-alkyl, tris-[(C1-C8)-alkyl]silyl, bis-hydroxyboryl-(C1-C8)-alkyl, bis[(C1-C8)-alkoxy]boryl-(C1-C8)-alkyl, tetramethyl-1,3,2-dioxaborolan-2-yl, tetramethyl-1,3,2-dioxaborolan-2-yl-(C1-C8)-alkyl, nitro-(C1-C8)-alkyl, C(O)R 14 , bis(C1-C8)-alkoxymethyl, bis(C1-C8)-alkoxymethyl-(C1-C8)-alkyl, or R 8 and R 10 together with the carbon atoms to which they are attached form an optionally further substituted fully or partially saturated 3- to 10-membered monocyclic or bicyclic heterocyclyl; R 11 and R 12may be the same or different and independently represent hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C 10 )-haloalkyl, (C2-C8)-haloalkenyl, (C3-C8)-haloalkynyl, (C3-C 10 )-cycloalkyl, (C3-C 10 )-halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10 )-halocycloalkenyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-haloalkoxy-(C1-C8)-alkyl, (C1-C8)-alkylthio-(C1-C8)-alkyl, (C1-C8)-haloalkylthio-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, aryl, aryl-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C4-C 10 )-Cycloalkenyl-(C1-C8)-alkyl, COR 13 , SO2R 14 , heterocyclyl, (C1-C8)-alkoxycarbonyl, bis[(C1-C8)-alkyl]aminocarbonyl-(C1-C8)-alkyl, (C1-C8)-alkylaminocarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkylaminocarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxycarbonyl, heteroaryl-(C1-C8)-alkoxycarbonyl, (C2-C8)-alkenyloxycarbonyl, (C2-C8)-alkynyloxycarbonyl, heterocyclyl-(C1-C8)-alkyl, or R 11 and R 12 together with the nitrogen atom to which they are attached form a fully or partially saturated 3- to 10-membered monocyclic or bicyclic ring which may be interrupted by heteroatoms and which may be further substituted; R 13is hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C 10 )-haloalkyl, (C2-C8)-haloalkenyl, (C3-C8)-haloalkynyl, (C3-C 10 )-cycloalkyl, (C3-C 10 )-halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10 )-halocycloalkenyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-haloalkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-a alkyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, aryl, aryl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxy-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C4-C 10 )-cycloalkenyl-(C1-C8)-alkyl, bis[(C1-C8)-alkyl]aminocarbonyl-(C1-C8)-alkyl, (C1-C8)-alkylaminocarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkylaminocarbonyl-(C1-C8)-alkyl, bis[(C1-C8)-alkyl]amino-(C2-C6)-alkyl, (C1-C8)-alkylamino-(C2-C6)-alkyl, aryl-(C1-C8)-alkylamino-(C2-C6)-alkyl, R 14 S-(C1-C8)-alkyl, R 14 (O)S-(C1-C8)-alkyl, R 14OS-(C1-C8)-alkyl, hydroxycarbonyl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl, tris[(C1-C8)-alkyl]silyl-(C1-C8)-alkyl, bis[(C1-C8)-alkyl](aryl)silyl(C1-C8)-alkyl, [(C1-C8)-alkyl]bis(aryl)silyl-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyloxy -(C1-C8)-alkyl, (C3-C8)-cycloalkylcarbonyloxy-(C1-C8)-alkyl, arylcarbonyloxy-(C1-C8)-alkyl, heteroarylcarbonyloxy-(C1-C8)-alkyl, heterocyclylcarbonyloxy-(C1-C8)-alkyl, aryloxy-(C1-C8)-alkyl, heteroaryloxy-(C1-C8)-alkyl, (C1-C8)-alkoxycarbonyl, R 14 is hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C 10 )-haloalkyl, (C2-C8)-haloalkenyl, (C3-C8)-haloalkynyl, (C3-C 10 )-cycloalkyl, (C3-C 10 )-halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10 )-halocycloalkenyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, aryl, aryl-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C4-C 10)-cycloalkenyl-(C1-C8)-alkyl, bis[(C1-C8)-alkyl]amino, (C1-C8)-alkylamino, aryl-(C1-C8)-amino, aryl-(C1-C6)-alkylamino, aryl-[(C1-C8)-alkyl]amino; (C3-C8)-cycloalkylamino, (C3-C8)-cycloalkyl-[(C1-C8)-alkyl]amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, and X and Y are independently O (oxygen) or S (sulfur); Substituted N-phenyluracils or salts thereof are provided. DETAILED DESCRIPTION OF THE INVENTION

[0013] The present invention particularly preferably R 1 is hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, R 2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (C1-C6)-alkoxy, R 3 is hydrogen, halogen, or (C1-C6)-alkoxy; R 4 is halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C6)-haloalkyl, (C2-C6)-alkynyl, R 5 , R 6 and R 7 are independently hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, G is unbranched or branched (C1-C6)-alkylene; Q is a group having the formula:

[0014] [ka]

[0015] is a radical of R 8 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, aryl, aryl-(C1-C6)-alkyl, heteroaryl, (C2-C6)-alkynyl, (C2-C6)-alkenyl, C(O)R 13 , C(O)OR 13 , (C1-C6)-alkoxy-(C1-C6)-alkyl, R 9 is hydrogen or (C1-C4)-alkyl, R 10 is cyano, NO2, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl, R 11 R 12 N-(C1-C8)-alkyl, R 13 O-(C1-C8)-alkyl, cyano-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyloxy-(C1-C8)-alkyl, (C3-C8)-cycloalkylcarbonyloxy-(C1-C8)-alkyl, arylcarbonyloxy-(C1-C8)-alkyl, heteroarylcarbonyloxy-(C1-C8)-alkyl, heterocyclylcarbonyloxy-(C1-C8)-alkyl, OR 13 , N.R. 11 R 12 , S.R. 14 , S(O)R 14 , SO2R 14 , R 14 S-(C1-C8)-alkyl, R 14 (O)S-(C1-C8)-alkyl, R 14OS-(C1-C8)-alkyl, tris[(C1-C8)-alkyl]silyl-(C1-C8)-alkyl, bis[(C1-C8)-alkyl](aryl)silyl(C1-C8)-alkyl, [(C1-C8)-alkyl]bis(aryl)silyl-(C1-C8)-alkyl, tris-[(C1-C8)-alkyl]silyl, bis-hydroxyboryl-(C1-C8)-alkyl, bis[(C1-C8)-alkoxy]boryl-(C1-C8)-alkyl, tetramethyl-1,3,2-dioxaborolan-2-yl, tetramethyl-1,3,2-dioxaborolan-2-yl-(C1-C8)-alkyl, nitro-(C1-C8)-alkyl, C(O)R 14 , bis(C1-C8)-alkoxymethyl, bis(C1-C8)-alkoxymethyl-(C1-C8)-alkyl, R 8 and R 10 together with the carbon atoms to which they are attached form an optionally further substituted fully or partially saturated 3- to 10-membered monocyclic or bicyclic heterocyclyl; R 11 and R 12 may be the same or different and independently represent hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C 10 )-haloalkyl, (C2-C8)-haloalkenyl, (C3-C8)-haloalkynyl, (C3-C 10 )-cycloalkyl, (C3-C 10 )-halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10)-halocycloalkenyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-haloalkoxy-(C1-C8)-alkyl, (C1-C8)-alkylthio-(C1-C8)-alkyl, (C1-C8)-haloalkylthio-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, aryl, aryl-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C4-C 10 )-Cycloalkenyl-(C1-C8)-alkyl, COR 13 , SO2R 14 , heterocyclyl, (C1-C8)-alkoxycarbonyl, bis[(C1-C8)-alkyl]aminocarbonyl-(C1-C8)-alkyl, (C1-C8)-alkylaminocarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkylaminocarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxycarbonyl, heteroaryl-(C1-C8)-alkoxycarbonyl, (C2-C8)-alkenyloxycarbonyl, (C2-C8)-alkynyloxycarbonyl, heterocyclyl-(C1-C8)-alkyl, or R 11 and R 12 together with the nitrogen atom to which they are attached form a fully or partially saturated 3- to 10-membered monocyclic or bicyclic ring which may be interrupted by heteroatoms and which may be further substituted; R 13 is hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C 10 )-haloalkyl, (C2-C8)-haloalkenyl, (C3-C8)-haloalkynyl, (C3-C 10 )-cycloalkyl, (C3-C 10 )-halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10)-halocycloalkenyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-haloalkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-a alkyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, aryl, aryl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxy-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C4-C 10 )-cycloalkenyl-(C1-C8)-alkyl, bis[(C1-C8)-alkyl]aminocarbonyl-(C1-C8)-alkyl, (C1-C8)-alkylaminocarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkylaminocarbonyl-(C1-C8)-alkyl, bis[(C1-C8)-alkyl]amino-(C2-C6)-alkyl, (C1-C8)-alkylamino-(C2-C6)-alkyl, aryl-(C1-C8)-alkylamino-(C2-C6)-alkyl, R 14 S-(C1-C8)-alkyl, R 14 (O)S-(C1-C8)-alkyl, R 14OS-(C1-C8)-alkyl, hydroxycarbonyl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl, tris[(C1-C8)-alkyl]silyl-(C1-C8)-alkyl, bis[(C1-C8)-alkyl](aryl)silyl(C1-C8)-alkyl, [(C1-C8)-alkyl]bis(aryl)silyl-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyloxy -(C1-C8)-alkyl, (C3-C8)-cycloalkylcarbonyloxy-(C1-C8)-alkyl, arylcarbonyloxy-(C1-C8)-alkyl, heteroarylcarbonyloxy-(C1-C8)-alkyl, heterocyclylcarbonyloxy-(C1-C8)-alkyl, aryloxy-(C1-C8)-alkyl, heteroaryloxy-(C1-C8)-alkyl, (C1-C8)-alkoxycarbonyl, R 14 is hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C 10 )-haloalkyl, (C2-C8)-haloalkenyl, (C3-C8)-haloalkynyl, (C3-C 10 )-cycloalkyl, (C3-C 10 )-halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10 )-halocycloalkenyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, aryl, aryl-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C4-C 10)-cycloalkenyl-(C1-C8)-alkyl, bis[(C1-C8)-alkyl]amino, (C1-C8)-alkylamino, aryl-(C1-C8)-amino, aryl-(C1-C6)-alkylamino, aryl-[(C1-C8)-alkyl]amino; (C3-C8)-cycloalkylamino, (C3-C8)-cycloalkyl-[(C1-C8)-alkyl]amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, and X and Y are independently O (oxygen) or S (sulfur); Compounds of general formula (I) are provided:

[0016] The present invention very particularly preferably comprises R 1 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl butyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy; R 2is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, prop-1-yloxy, but-1-yloxy, R 3 is hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, R 4 is fluorine, chlorine, bromine, cyano, NO2, C(O)NH2, C(S)NH2, trifluoromethyl, difluoromethyl, pentafluoroethyl, ethynyl, propyn-1-yl, 1-butyn-1-yl, pentyn-1-yl, hexyn-1-yl, R 5 , R 6 and R 7 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1- ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy; G is methylene, (methyl)methylene, (ethyl)methylene, (prop-1-yl)methylene, (prop-2-yl)methylene, (but-1-yl)methylene, (but-2-yl)methylene, (pent-1-yl)methylene, (pent-2-yl)methylene, (pent-3-yl)methylene, (dimethyl)methylene, (diethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl 1-Propylene, 3-Methylpropyl-1-ene, 1,1-Dimethylethyl-1-ene, 2,2-Dimethylethyl-1-ene, 1-Ethylethyl-1-ene, 2-Ethylethyl-1-ene, 1-(Propylene)ethyl-1-ene, 2-(Propylene)ethyl-1-ene, 1-(Propylene)ethyl-1-ene, 2-(Propylene)ethyl-1-ene, 1,1,2-Trimethylethyl-1-ene, 1,2,2-Trimethylethyl-1-ene, 1,1,2,2-Trimethylethyl-1-ene, 1,1,2,2-Trimethylethyl-1-ene ene, n-pentylene, 1-methylbutyl-1-ene, 2-methylbutyl-1-ene, 3-methylbutyl-1-ene, 4-methylbutyl-1-ene, 1,1-dimethylpropyl-1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl-1-ene, 1,2-dimethylpropyl-1-ene, 1,3-dimethylpropyl-1-ene, 1-ethylpropyl-1-ene, n-hexylene, 1-methylpentyl-1-ene, 2-methylpentyl-1-ene, 3-methylpentyl-1-ene, 4-methylbutyl-1-ene ethylpentyl-1-ene, 1,1-dimethylbutyl-1-ene, 1,2-dimethylbutyl-1-ene, 1,3-dimethylbutyl-1-ene, 2,2-dimethylbutyl-1-ene, 2,3-dimethylbutyl-1-ene, 3,3-dimethylbutyl-1-ene, 1-ethylbutyl-1-ene, 2-ethylbutyl-1-ene, 1,1,2-trimethylpropyl-1-ene, 1,2,2-trimethylpropyl-1-ene, 1-ethyl-1-methylpropyl-1-ene, 1-ethyl-2-methylpropyl-1-ene, X and Y are independently O (oxygen) or S (sulfur); and Provided are compounds of general formula (I), wherein Q is one of the moieties Q-1 to Q-406 defined below, and the arrows in the structural formula in the table below represent the bond of the respective Q group to the carbonyl group in general formula (I):

[0017] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7] [Table 1-8] [Table 1-9] [Table 1-10] [Table 1-11] [Table 1-12] [Table 1-13]

[0018] The present invention particularly preferably R 1is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, R 2 is fluorine, R 3 is hydrogen, fluorine, chlorine, bromine, methoxy, R 4 is fluorine, chlorine, bromine, cyano, NO2, C(O)NH2, C(S)NH2, trifluoromethyl, ethynyl, propyn-1-yl, R 5 , R 6 , R 7 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy; G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, 1,1-dimethylethyl-1-ene, 2,2-dimethylethyl-1-ene, 1-ethylethyl-1-ene, 2-ethylethyl-1-ene, 1-(prop-1-yl)ethyl-1-ene, 2-(prop-1-yl) ethyl-1-ene, 1-(prop-2-yl)ethyl-1-ene, 2-(prop-2-yl)ethyl-1-ene, n-pentylene, 1-methylbutyl-1-ene, 2-methylbutyl-1-ene, 3-methylbutyl-1-ene, 4-methylbutyl-1-ene, 1,1-dimethylpropyl-1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl-1-ene, 1,2-dimethylpropyl-1-ene, 1,3-dimethylpropyl-1-ene, 1-ethylpropyl-1-ene, n-hexylene; X and Y are independently O (oxygen) or S (sulfur); and Q is one of the moieties Q-1 to Q-406 specifically mentioned above; Compounds of general formula (I) are provided:

[0019] The present invention very particularly preferably comprises R 1 is hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, R 2 is fluorine, R 3 is fluorine, R 4 are chlorine, bromine, cyano, NO2, C(O)NH2, C(S)NH2, R 5 , R 6 , R 7 are independently hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, or trifluoromethoxy; G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, n-pentylene, n-hexylene; X and Y are independently O (oxygen) or S (sulfur); and Q is one of the moieties Q-1 to Q-406 specifically mentioned above; Compounds of general formula (I) are provided:

[0020] The present invention particularly preferably comprises: R 1 are hydrogen, fluorine, chlorine, and bromine, R 2 is fluorine, R 3 is fluorine, R 4 are chlorine, bromine, cyano, and NO2, R 5 are hydrogen, fluorine, chlorine, and bromine, R 6is hydrogen, fluorine, chlorine, bromine, cyano, R 7 are hydrogen, fluorine, chlorine, and bromine, G is methylene, (methyl)methylene, (ethyl)methylene; X and Y are independently O (oxygen) or S (sulfur); and Q is one of the moieties Q-1 to Q-406 specifically mentioned above; Compounds of general formula (I) are provided:

[0021] The present invention very particularly preferably comprises R 1 is hydrogen, R 2 is fluorine, R 3 is fluorine, R 4 are chlorine, bromine, cyano, and NO2, R 5 are hydrogen, fluorine, chlorine, and bromine, R 6 is hydrogen, fluorine, chlorine, bromine, cyano, R 7 is hydrogen, G is methylene, (methyl)methylene; X is O (oxygen) or S (sulfur), Y is O (oxygen), and Q is one of the moieties Q-1 to Q-406 specifically mentioned above; Compounds of general formula (I) are provided:

[0022] The present invention very particularly preferably comprises R 1 is hydrogen, R 2 is fluorine, R 3 is fluorine, R 4 are chlorine, bromine, cyano, and NO2, R5 are hydrogen and fluorine, R 6 is hydrogen, fluorine, bromine, or cyano; R 7 is hydrogen, G is methylene, (methyl)methylene; X is O (oxygen) or S (sulfur), Y is O (oxygen), and Q is one of the moieties Q-1 through Q-35, Q-41 through Q-45, Q-58, Q-71 through Q-80, Q-89, Q-94, Q-95, Q-115, Q-120 through Q-123, Q-152 through Q-155, Q-166 through Q-170, Q-176 through Q-190, Q-261 through Q-348, Q-352 through Q-372, Q-377, and Q-391 through Q-399 specifically mentioned above; Compounds of general formula (I) are provided:

[0023] The present invention very particularly preferably comprises R 1 is hydrogen, R 2 is fluorine, R 3 is fluorine, R 4 are chlorine, bromine, cyano, and NO2, R 5 are hydrogen and fluorine, R 6 is hydrogen, fluorine, bromine, or cyano; R 7 is hydrogen, G is methylene, (methyl)methylene; X is O (oxygen) or S (sulfur), Y is O (oxygen), and Q represents the above-specified parts Q-1, Q-2, Q-3, Q-4, Q-7, Q-8, Q-9, Q-17, Q-18, Q-23, Q-24, Q-26, Q-27, Q-41, Q-42, Q-43, Q-58, Q-71, Q-72, Q-89, Q-94, Q-115, Q-121, Q-176, Q-177, Q-179, Q-183, Q-272, Q-274, Q-275, Q-276, Q- 277, Q-278, Q-281, Q-282, Q-283, Q-284, Q-286, Q-288, Q-291, Q-296, Q-301, Q-302, Q-303, Q-308, Q-309, Q-321, Q-327, Q-328, Q-329, Q-331, Q-335, Q-339, Q-356, Q-365, Q-366, Q-367, Q-371, Q-394, Compounds of general formula (I) are provided:

[0024] The above general or preferred radical definitions apply both to the final products of general formula (I) and also to the starting materials or intermediates necessary in each case for their preparation. These radical definitions can be combined with one another as necessary, i.e., include combinations of the given preferred ranges.

[0025] Mainly because of their higher herbicidal activity, better selectivity and / or better formulation possibilities, the compounds of the invention of the specified general formula (I) or their salts or their uses according to the invention are of particular interest, in which the individual radicals have one of the preferred meanings specified above or below, or in particular one or more of the preferred meanings specified above or below occur together.

[0026] Where a compound can produce tautomers by hydrogen transfer whose structure is not geometrically conformed by general formula (I), these tautomers are nevertheless encompassed within the definition of the compounds of the invention of general formula (I), unless a specific tautomer is being discussed. For example, many carbonyl compounds can exist in both keto and enol forms, and both forms are encompassed by the definition of the compounds of general formula (I).

[0027] Depending on the nature of the substituents and the manner in which they are attached, compounds of general formula (I) may exist as stereoisomers. All possible stereoisomers, defined by their specific three-dimensional configuration, such as enantiomers, diastereomers, and Z and E isomers, are encompassed by general formula (I). For example, if one or more alkenyl groups are present, diastereomers (Z and E isomers) may exist. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may exist. Stereoisomers can be obtained from mixtures obtained during production by conventional separation methods. Enantiomeric or diastereomeric excess can be found on an analytical scale, or chromatographic separation can be performed on a preparative scale to obtain samples for biological testing. It is also possible to selectively prepare stereoisomers by employing stereoselective reactions using optically active starting materials and / or auxiliaries. Thus, the present invention also relates to all stereoisomers encompassed by general formula (I) but not represented by a specific stereoisomer, and mixtures thereof.

[0028] If the compounds are obtained as solids, purification can also be achieved by recrystallization or digestion. If individual compounds (I) cannot be satisfactorily obtained by the routes described below, they can be prepared by derivatization of other compounds (I).

[0029] Suitable isolation methods, purification methods and methods for separating stereoisomers of compounds of general formula (I) are generally known to those skilled in the art from similar examples, for example, physical methods such as crystallization, chromatographic methods, in particular column chromatography and HPLC (high pressure liquid chromatography), distillation under reduced pressure if necessary, extraction and other methods, any remaining mixtures can generally be separated, for example, by chromatographic separation on chiral solid phases. For example, methods such as crystallization of diastereomeric salts, which can be obtained from diastereomeric mixtures using optically active acids, if appropriate, with optically active bases, provided that acidic groups are present, are suitable for preparative or industrial scale.

[0030] The terms used above and further below in relation to the compounds of the present invention are explained, and will have the definitions well known to those skilled in the art, and in particular as explained hereinafter.

[0031] Unless otherwise defined, the names of chemical groups generally indicate that the bond to the backbone or the rest of the molecule is via the structural element of the last-mentioned relevant chemical group, i.e., for example, via an oxygen atom in the case of (C2-C8)-alkenyloxy, and in each case heterocyclyl-(C1-C8)-alkyl or (C1-C6)-alkoxy-(C1-C6)-alkoxy-(C1-C6)-alkyl, via a carbon atom of the alkyl group.

[0032] According to the present invention, "alkylthio" - alone or as part of a chemical group - preferably (C1-C 10 )-, (C1-C6)- or (C1-C4)-alkylthio, such as (C1-C6)-, (C1-C6)- or (C1-C4)-alkylthio, including, but not limited to, 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, Examples of (C1-C6)-alkylthio include hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio.

[0033] "Alkoxy" refers to an alkyl radical attached through an oxygen atom, such as (but not limited to), methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, Examples of the alkyl groups include (C1-C6)-alkoxy groups such as 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 refers to an alkenyl radical bonded by an oxygen atom, and alkynyloxy refers to an alkynyl radical bonded by an oxygen atom, for example, (C2-C6). 10 )-, (C2-C6)- or (C2-C4)-alkenoxy and (C3-C 10 )-, (C3-C6)- or (C3-C4)-alkynoxy, etc.

[0034] According to the present invention, "alkylcarbonyl" (alkyl-C(=O)-), unless otherwise defined, is a group (C1-C 10 (C1-C6)- or (C1-C4)-alkylcarbonyl. The number of carbon atoms in this specification refers to the alkyl radical in the alkylcarbonyl group.

[0035] "Alkoxycarbonyl" (alkyl-OC(=O)-), unless otherwise defined, is an alkyl group (C1-C 10represents an alkyl radical linked to the backbone by -OC(=O)-, such as (C1-C6)-, (C1-C4)-alkoxycarbonyl. The number of carbon atoms in this specification refers to the alkyl radical in the alkoxycarbonyl group. Similarly, "alkenyloxycarbonyl" and "alkynyloxycarbonyl" refer, according to the present invention, to (C2-C 10 )-, (C2-C6)- or (C2-C4)-alkenyloxycarbonyl or (C3-C 10 and alkenyl and alkynyl radicals linked to the backbone by -OC(=O)-, such as (C3-C6)-, (C3-C6)-, or (C3-C4)-alkynyloxycarbonyl. The number of carbon atoms in this specification refers to the alkenyl or alkynyl radical in the alkenyloxycarbonyl or alkynyloxycarbonyl group, respectively.

[0036] According to the present invention, the term "alkylcarbonyloxy" (alkyl-C(=O)-O-), unless otherwise defined, refers to any of (C1-C 10 represents an alkyl radical attached to the skeleton by oxygen in a carbonyloxy group (-C(=O)-O-), such as (C1-C6)-, (C1-C4)- or (C1-C4)-alkylcarbonyloxy. The number of carbon atoms in this specification relates to the alkyl radical in the alkylcarbonyloxy group.

[0037] C(O)R 13 , C(O)OR 13 , OC(O)NR 11 R 12 or C(O)NR 11 R 12 In the shortened form, O shown in parentheses is an oxygen atom attached to the adjacent carbon atom by a double bond.

[0038] OC(S)OR 13 ,OC(S)SR 14 , OC(S)NR 11 R 12 In the shorthand forms such as, the shorthand form S shown in parentheses represents a sulfur atom attached to an adjacent carbon atom by a double bond.

[0039] The term "aryl" denotes an optionally substituted monocyclic, bicyclic or polycyclic aromatic system preferably having 6 to 14, especially 6 to 10, ring carbon atoms, such as phenyl, naphthyl, anthryl, phenanthrenyl and the like, preferably phenyl.

[0040] The term "optionally substituted aryl" also includes polycyclic structures such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, etc., where the binding site is on the aromatic structure. In systematic terms, "aryl" is also encompassed generally by the term "optionally substituted phenyl." Preferred aryl substituents herein include, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bisalkylaminoalkoxy, tris[alkyl]silyl, bis[alkyl]arylsilyl, bis[alkyl]alkyl, Examples of the alkynyl group include arylsilyl, tris[alkyl]silylalkynyl, arylalkynyl, heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bisalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, bisalkylaminocarbonyl, heteroarylalkoxy, and arylalkoxy.

[0041] Heterocyclic radicals (heterocyclyl) are saturated, unsaturated, partially saturated, or heteroaromatic, and may be unsubstituted or substituted. If substituted, they contain at least one heterocyclic ring (= a carbocyclic ring in which at least one carbon atom is replaced by a heteroatom, preferably a heteroatom selected from N, O, S, and P), with the binding site being on a ring atom. If the heterocyclyl radical or heterocyclic ring is optionally substituted, it may be fused to another carbocyclic or heterocyclic ring. In the case of optionally substituted heterocyclyl, polycyclic systems also include, for example, 8-azabicyclo[3.2.1]octanyl, 8-azabicyclo[2.2.2]octanyl, or 1-azabicyclo[2.2.1]heptyl. Optionally substituted heterocyclyl also includes spirocyclic systems, for example, 1-oxa-5-azacyclo[2.3]hexyl. Unless otherwise defined, heterocyclic rings preferably contain 3 to 9 ring atoms, especially 3 to 6 ring atoms, one or more, preferably 1 to 4, especially 1, 2 or 3 heteroatoms selected from the group N, O and S in the heterocyclic ring, although two oxygen atoms should not be directly adjacent to one heteroatom selected from the group N, O and S, for example: 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or -3-yl, 2,3-dihydro-1H-pyrrol-1- or -2- or -3- or -4- or -5-yl; 2,5-dihydro-1H-pyrrol-1- or -2- or -3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or -3- or -4- or -5-yl or -6-yl; 1,2,3,6-tetrahydropyridin-1- or -2- or -3- or -4- or -5- or -6-yl; 1,2,3,4-tetrahydropyridin-1- or -2- or -3- or -4- or -5- or -6-yl; 1,4-dihydropyridin-1- or -2- or -3- or -4-yl; 2,3-dihydropyridin-2- or -3- or -4- or -5- or -6-yl; 2,5-dihydropyridin-2- or -3- or -4- or -5- or -6-yl, 1- or 2- or 3- or 4-azepanyl;2,3,4,5-Tetrahydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-Tetrahydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-Tetrahydro-1H-azepin-1- or -2- or -3- or -4-yl; 3,4,5,6-Tetrahydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-Dihydro-1H-azepine -1- or -2- or -3- or -4-yl;2,5-dihydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl;2,7-dihydro-1H-azepin-1- or -2- or -3- or -4-yl;2,3-dihydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl;3,4-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl;3,6-dihydro-2H-azepin- 2- or -3- or -4- or -5- or -6- or -7-yl; 5,6-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-3H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 3H-azepin-2- or -3- or or -4- or -5- or -6- or -7-yl; 4H-azepine-2- or -3- or -4- or -5- or -6- or -7-yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or -3- or -4- or -5-yl; 2,5-dihydrofuran-2- or -3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl;3,6-Dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl; 2H-pyran-2- or -3- or -4- or -5- or -6-yl; 4H-pyran-2- or -3- or -4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl ;2,3,4,7-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl;2,3,6,7-tetrahydrooxepin-2- or -3- or -4-yl;2,3-dihydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl;4,5-dihydrooxepin-2- or -3- or -4-yl;2,5-dihydrooxepin-2- or -3- or -4-yl Droxepin-2- or -3- or -4- or -5- or -6- or -7-yl; Oxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2- or 3-Tetrahydrothiophenyl; 2,3-Dihydrothiophen-2- or -3- or -4- or -5-yl; 2,5-Dihydrothiophen-2- or -3-yl; Tetrahydro-2H-thio Pyran-2- or -3- or -4-yl; 3,4-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 4H-thiopyran-2- or -3- or -4-yl. Preferred 3- and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1-, 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, and 1,3-dioxetan-2-yl. Further examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic radicals having two heteroatoms selected from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl;2,3-Dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-Dihydro-1H-imidazol-1- or 2- or 3- or 4-yl; 2,5-Dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; 4,5-Dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; Hexahydropyridazin-1- or 2- or 3- or 4-yl; 1,2,3,4-Tetrahydropyridazin-1- or 2 - or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-tetrahydropyridazin-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazin-3 or 4-yl; 1,6-dihydropyridazin ridazin-1- or 3- or 4- or 5- or 6-yl; hexahydropyrimidin-1- or 2- or 3- or 4-yl; 1,4,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2 -dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidin-2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or 6-yl; 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-tetrahydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,2,3,4-tetrahydropyrazin-1- or 2- or 3- or 4- or 5- or 6-yl;1,2-Dihydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,4-Dihydropyrazin-1- or 2- or 3-yl; 2,3-Dihydropyrazin-2- or 3- or 5- or 6-yl; 2,5-Dihydropyrazin-2- or 3-yl; 1,3-Dioxolan-2- or 4- or 5-yl; 1,3-Dioxol-2- or 4-yl; 1,3-Dioxan-2- or 4- or 5-yl; 4H-1,3-Dioxin-2- or 4- or 5- or 6-yl; 1,4-Dioxan-2- or 3- - or 5- or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; 1,4-dioxin-2- or 3-yl; 1,2-dithiolan-3- or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl; 1,3-dithiolan-2- or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3- or 4-yl; 3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-1,2-dithiin-3- or 4- yl;1,2-dithiin-3- or 4-yl;1,3-dithian-2- or 4- or 5-yl;4H-1,3-dithiin-2- or 4- or 5- or 6-yl;isoxazolidin-2- or 3- or 4- or 5-yl;2,3-dihydroisoxazol-2- or 3- or 4- or 5-yl;2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl;4,5-dihydroisoxazol-3- or 4- or 5-yl;1,3-oxazolidin-2- or 3- or 4- or 5-yl yl; 2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 1,2-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl;5,6-Dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-1,2-oxazin-3- or 4- or 5- or 6-yl; 4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 1,3-oxazinane-2-; or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-oxazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-oxazin-2- or 4- or 5- or 6-yl; 2H-1,3-oxazin-2- or 4- or 5- or 6-yl; 6H-1,3-oxazin 2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 4H-1,3-oxazin-2- or 4- or 5- or 6-yl; morpholin-2- or 3- or 4-yl; 3,4-dihydro-2H-1,4-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 4H-1,4-oxazin-2- or 3-yl; 1,2-oxazepan-2- or 3- or 4 - or 5- or 6- or 7-yl;2,3,4,5-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,3,4,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,3,6,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,5,6,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;4 ,5,6,7-tetrahydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl;4,7-Dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 6,7-Dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 1,3-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-Tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-Tetrahydro-1,3-oxazepin- 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,3 -oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,4-Oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl;4,5,6,7-Tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-Dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5-Dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,7-Dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5-Dihydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;4,7-dihydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;6,7-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl;1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl;isothiazolidine-2- or 3- or 4- or 5-yl;2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl;2,5-dihydroisothiazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisothiazol-3- or 4- or 5-yl; 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-thiazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 1,3-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;Further examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic radicals having three heteroatoms selected from the group consisting of N, O and S, such as 1,4,2-dioxazolidin-2- or 3- or 5-yl; 1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or 3- or 5- or 6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-1,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-1,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-1,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 5H-1,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 7H-1,4,2-dioxazepin-3- or 5- or 6- or 7-yl. Structural examples of optionally further substituted heterocycles are listed in the table below:

[0042] [Table 2-1] [Table 2-2] [Table 2-3]

[0043] Heterocycles in the above list are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, haloalkenyl Substituted by alkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, heteroaryloxy, bisalkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.

[0044] If the base structure is substituted with "one or more radicals" selected from a list of radicals (=groups) or generally with a defined radical group, in each case this includes simultaneous substitution with multiple identical and / or structurally different radicals.

[0045] In the case of a partially or fully saturated nitrogen heterocycle, it may be attached to the rest of the molecule by either the carbon or the nitrogen.

[0046] Suitable substituents for substituted heterocyclic radicals are the substituents further specified below, as well as oxo and thioxo. An oxo group as a substituent on a ring carbon atom is, for example, a carbonyl group in a heterocyclic ring. As a result, lactones and lactams are also preferably included. An oxo group may also be present on a ring heteroatom that can exist in different oxidation states, for example, in the case of N and S, forming, for example, divalent N(O), S(O) (abbreviated SO) and S(O)2 (abbreviated SO2) groups in the heterocyclic ring. In the case of -N(O)- and -S(O)- groups, both enantiomers in each case are included.

[0047] According to the present invention, the expression "heteroaryl" denotes heteroaromatic compounds, i.e. fully unsaturated aromatic heterocyclic compounds, preferably 5- to 7-membered rings having 1 to 4, preferably 1 or 2, identical or different heteroatoms, preferably O, S or N. Heteroaryls of the present invention include, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl, 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-trimethyl-1H-pyrrol ... Azol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1, 2,3-Oxadiazol-4-yl, 1,2,3-Oxadiazol-5-yl, 1,2,5-Oxadiazol-3-yl, Azepinyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, 1,3,5-Triazin-2-yl, 1,2,4-Triazin-3-yl, 1,2,4-Triazin-5-yl , 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,The heteroaryl group of the present invention may be substituted with one or more of the same or different radicals.When two adjacent carbon atoms are part of another aromatic ring, the system is a fused heteroaromatic system, such as a benzofused or polyannelated heteroaromatic system. Preferred examples include quinolines (e.g., quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); isoquinolines (e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine, phthalazine, pyridopyrazines, pyridopyrimidines, pyridopyridazines, pteridines, pyrimidopyrimidines. Examples of heteroaryl include 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen ...6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzofuran-7-yl, 1-benzothiophen-3-yl, 1-benzofuran-8-yl, 1-benzofuran-9-yl, 1-benzothiophen-10-yl, 1-benzothiophen-11-yl, 1-benzofuran-12-yl, 1-benzothiophen-13-yl, 1-benzofuran-14-yl, 1-benzofuran-15-yl, 1-benzofuran-16-yl, 1-benzofuran-17-yl, 1-benzothiophen-18-yl, 1-benzothiophen-19-yl, 1-benzofuran-19-yl, 1-benzofuran-1 Benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1H-indazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazol-2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H- Indazol-7-yl, 2H-isoindol-2-yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H-benzimidazol-7-yl 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,Also included are 5- or 6-membered benzo-fused rings selected from the group consisting of 2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,2-benzisoxazol-7-yl, 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, and 1,2-benzisothiazol-7-yl.

[0048] The term "halogen" denotes, for example, fluorine, chlorine, bromine or iodine. When the term is used in reference to a radical, "halogen" denotes, for example, a fluorine, chlorine, bromine or iodine atom.

[0049] According to the present invention, "alkyl" denotes a linear or branched saturated hydrocarbon radical which may be mono- or polysubstituted, in the latter case referred to as "substituted alkyl". Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine. The preposition "bis" also includes combinations of different alkyl radicals, for example methyl (ethyl) or ethyl (methyl).

[0050] "Haloalkyl", "-alkenyl" and "-alkynyl" refer to alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted with the same or different halogen atoms, for example, monohaloalkyl, such as CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, CH2F; perhaloalkyl, such as CCl3, CClF2, CFCl2, CF2CClF2, CF2CClFCF3; polyhaloalkyl, such as CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3; the term "perhaloalkyl" also includes the term "perfluoroalkyl".

[0051] "Haloalkoxy" is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3, and OCH2CH2Cl; this likewise applies to haloalkenyl and other halogen-substituted radicals.

[0052] As an example, the expression "(C1-C4)-alkyl" referred to herein is a shorthand description of a straight-chain or branched-chain alkyl having 1 to 4 carbon atoms according to the range stated for the carbon atom, i.e., encompasses methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radicals. Conventional alkyl radicals having a larger specific range of carbon atoms, such as "(C1-C6)-alkyl," likewise encompass straight-chain or branched-chain alkyl radicals having a larger number of carbon atoms, i.e., by way of example, alkyl radicals having 5 and 6 carbon atoms.

[0053] Unless otherwise specified, for hydrocarbon radicals, such as alkyl, alkenyl, and alkynyl radicals, including complex radicals, lower carbon skeletons having 1 to 6 carbon atoms are preferred, or for unsaturated groups, 2 to 6 carbon atoms. Alkyl radicals, including complex radicals such as alkoxy, haloalkyl, and others, are, for example, methyl, ethyl, n-propyl or i-propyl, n-, i-, t-, or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl, and 1,3-dimethylbutyl, and heptyls such as n-heptyl, 1-methylhexyl, and 1,4-dimethylpentyl; alkenyl and alkynyl radicals are defined as unsaturated radicals, possibly corresponding to alkyl radicals, in which at least one double or triple bond is present. Radicals with one double or triple bond are preferred.

[0054] The term "alkenyl" includes linear or branched hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, such as allenyl (1,2-propadienyl), 1,2-butadienyl, and 1,2,3-pentatrienyl. Alkenyl refers, for example, to vinyl, which may be substituted by further alkyl radicals, such as (but not limited to) ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl- 1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl , 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl , 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,(C2-C6)-alkenyl such as 3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl.

[0055] The term "alkynyl" specifically includes straight or branched chain hydrocarbon radicals having more than one triple bond, or one or more triple bonds and one or more double bonds, for example, 1,3-butatrienyl or 3-penten-1-yn-1-yl. Examples of (C2-C6)-alkynyl include 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.

[0056] The term "cycloalkyl" preferably denotes a carbocyclic saturated ring system having 3 to 8 ring carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which may be further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or cycloalkylaminocarbonyl. Optionally substituted cycloalkyl includes ring systems having substituents, including substituents having a double bond on the cycloalkyl radical, for example alkylidene groups such as methylidene. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems are also included, such as, for example, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]pentan-5-yl, bicyclo[2.1.1]pentan-5-yl, bicyclo[2.1.0 ... Examples of cycloalkyl include cycloalkyl, cyclohexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl, and adamantan-2-yl, but also include systems such as 1,1'-bi(cyclopropyl)-1-yl, 1,1'-bi(cyclopropyl)-2-yl, etc. The term "C3-C7)-cycloalkyl" is an abbreviation for cycloalkyl having 3 to 7 carbon atoms corresponding to the range specified for carbon atoms.

[0057] In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-1-yl, and spiro[3.3]hept-2-yl.

[0058] "Cycloalkenyl" refers to a carbocyclic non-aromatic partially unsaturated ring system, preferably having 4 to 8 carbon atoms, such as 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl, or 1,4-cyclohexadienyl, and also includes substituents on the cycloalkenyl radical having a double bond, for example, alkylidene groups such as methylidene. In the case of optionally substituted cycloalkenyl, the explanations for substituted cycloalkyl apply analogously.

[0059] For example, (C1~C 10 In the form of )-alkylidene, the term "alkylidene" refers to a radical of a straight or branched chain hydrocarbon radical linked by a double bond. The only possible bonding sites for alkylidene are naturally those positions on the base structure where two hydrogens can be replaced by double bonds; radicals are, for example, =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5 or =C(C2H5)-C2H5. Cycloalkylidene refers to a carbocyclic radical linked by a double bond.

[0060] For example, in the form (C1-C8)-alkylene, the term "alkylene" denotes a radical of a straight or branched chain hydrocarbon radical attached at two positions to further groups.

[0061] "Alkoxyalkyl" refers to an alkoxy radical attached through an alkyl group, and "alkoxyalkoxy" refers to an alkoxyalkyl radical attached through an oxygen atom, e.g., methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.

[0062] An "arylalkyl" is an aryl radical attached through an alkyl group, a "heteroarylalkyl" refers to a heteroaryl radical attached through an alkyl group, and a "heterocyclylalkyl" refers to a heterocyclyl radical attached through an alkyl group.

[0063] "Cycloalkylalkyl" is a cycloalkyl bonded by an alkyl group, including (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl.

[0064] "Arylalkenyl" refers to an aryl radical attached through an alkenyl group, "heteroarylalkenyl" refers to a heteroaryl radical attached through an alkenyl group, and "heterocyclylalkenyl" refers to a heterocyclyl radical attached through an alkenyl group.

[0065] "Arylalkynyl" refers to an aryl radical attached through an alkynyl group, "heteroarylalkynyl" refers to a heteroaryl radical attached through an alkynyl group, and "heterocyclylalkynyl" refers to a heterocyclyl radical attached through an alkynyl group.

[0066] According to the present invention, "haloalkylthio" - by itself or as a component of a chemical group - is a straight or branched chain S-haloalkyl, preferably having 1 to 8, or 1 to 6 carbon atoms, such as (C1-C8)-, (C1-C6)- or (C1-C4)-haloalkylthio, including (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.

[0067] "Halocycloalkyl" and "halocycloalkenyl" refer to cycloalkyl or cycloalkenyl, respectively, that are partially or fully substituted with the same or different halogen atoms, such as F, Cl, and Br, or with haloalkyl, such as trifluoromethyl or difluoromethyl, and include, 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.

[0068] Synthesis of substituted N-phenyluracils of general formula (I).

[0069] The substituted N-phenyluracils of general formula (I) according to the present invention can be prepared using known methods. The synthetic routes used and considered proceed from commercially available or easily prepared heteroaromatic amines and similarly substituted hydroxyesters. In the following schemes, the moieties G, Q, R of general formula (I) are 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7, X and Y have the above-defined meanings unless an illustrative but non-limiting definition is given. As a first key intermediate in the synthesis of compounds of the present invention of general formula (Ia) where X is sulfur (S) and Y is oxygen (O), optionally further substituted mercaptophenyl-1H-pyrimidine-2,4-dione is prepared. This is illustrated by the synthesis of 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (IIa) (Scheme 1). To this end, a suitable substituted aniline, for example but not limited to, 2-fluoro-4-chloroaniline, is converted to the corresponding isocyanate using a suitable reagent (e.g., triphosgene) in a suitable polar aprotic solvent (e.g., dichloromethane), which is then converted in a next step to the corresponding pyrimidine-2,4-dione, which may be further substituted, for example but not limited to, 3-(4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione, by reaction with a suitable aminoacrylate using a suitable base (e.g., sodium hydride or potassium tert-butoxide) in a suitable polar aprotic solvent (e.g., N,N-dimethylformamide) (Scheme 1). Subsequent sulfochlorination with an appropriate reagent (e.g., chlorosulfonic acid) followed by reduction with an appropriate reducing agent (e.g., Zn, tin(II) chloride hydrate, or triphenylphosphine in EtOH and HCl) can produce 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 Korean Patent No. 1345394; European Patent No. 1122244; European Patent No. 408382; International Publication No. 2003 / 029226; International Publication No. 2010 / 038953; U.S. Patent Application Publication No. 2011 / 0224083; Korean Patent Application Publication No. 2011 / 110420). In Scheme 1, R 2 and R 3 is, by way of example and not limitation, fluorine, and R4 By way of example and not limitation, is chlorine, and X is by way of example and not limitation, sulfur.

[0070] [ka]

[0071] The synthesis of key intermediate (IIa) described in Scheme 1 can also be applied to the preparation of similar intermediates. Compound (II) is then converted to intermediate (III) in a first step utilizing an appropriate, optionally further substituted iodophenol using an appropriate base in a suitable polar aprotic solvent (e.g., dioxane) or an appropriate transition metal catalyst (e.g., tris(dibenzylideneacetone)dipalladium(0)) with an appropriate ligand (e.g., 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene) and a suitable base (e.g., diisopropyl(ethyl)amine). Each further substituted N-methyl-5-mercaptophenyl-1H-pyrimidine-2,4-dione intermediate (II) can then be converted to the desired compound of the present invention of general formula (Ia), where X is sulfur (S) and Y is oxygen (O), via various routes (Scheme 2). In Scheme 2 below, Q, R 2 , R 3 , R 3 and R 4 has the meaning of the present invention as described above. 1 , R 5 , R 6 , R 7is, for example, but not limited to, hydrogen, X is, for example, but not limited to, sulfur, Y is, for example, but not limited to, oxygen, and G is, for example, but not limited to, CH. The corresponding intermediate (III) shown in Scheme 2 can be converted to the corresponding oxyalkanoate intermediate (IVa, IVb) or the desired target compound of general formula (Ia) by reaction with an appropriate optionally further substituted iodoalkanoate (in Scheme 3, for example, iodoacetate) using an appropriate base (e.g., silver carbonate(I)) in a suitable polar aprotic solvent (e.g., n-hexane or cyclohexane) at elevated temperature (e.g., under microwave conditions) (see Synthesis 2009, 2725). The corresponding iodoalkanoates can be prepared by routes known from the literature (see Eur. J. Org. Chem., 2006, 71, 8459; WO2012037573; Organometallics, 2009, 28, 132).

[0072] [ka]

[0073] The ethyl ester (IVa) and tert-butyl ester (IVb) intermediates can then be converted to the corresponding free acids (V) using appropriate reaction conditions [use of an appropriate 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 reaction of the corresponding acid intermediate (V) with an appropriate compound QH mediated by a suitable coupling reagent (e.g., HOBt = 1-hydroxybenzotriazole, EDC = 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, HATU = O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, T3P = 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane 2,4,6-trioxide) in a suitable polar aprotic solvent (e.g., dichloromethane, chloroform) and a suitable base (e.g., diisopropylethylamine, triethylamine). 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 mediated by a suitable Lewis acid (e.g., indium(III) chloride) (see WO 2011 / 1307088).

[0074] The preparation of compounds of general formula (I) where X and Y are, by way of example and not limitation, oxygen (O), proceeds via the synthesis of a key intermediate (VI) bearing a fluorine substituent at 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, for example but not limited to, 2,5-difluoroaniline, is converted to the corresponding isocyanate using a suitable reagent (e.g., triphosgene) in a suitable polar aprotic solvent (e.g., dichloromethane), which is then converted in a next step to the corresponding pyrimidine-2,4-dione, which may be further substituted, for example but not limited to, 3-(2,5-difluorophenyl)-6-trifluoromethyl-1H-pyrimidine-2,4-dione, by reaction with a suitable aminoacrylate using a suitable base (e.g., sodium hydride or potassium tert-butoxide) in a suitable polar aprotic solvent (e.g., N,N-dimethylformamide) (Scheme 3). Nitration with an appropriate nitrating reagent followed by N-methylation with an appropriate methylating reagent provides the desired intermediate, here by way of example and not limitation, 3-(2,5-difluoro-4-nitro)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (VIa). In Scheme 3 below, R 2 and R 3 is, by way of example and not limitation, fluorine, and R 4 is, by way of example and not limitation, nitro.

[0075] [ka]

[0076] The intermediate (VI) obtained by the above method, for example, compound (VIa), can then be converted to the desired substituted N-phenyluracil (Ib, R 4= nitro). The intermediate (VII) used for this purpose can be obtained by a multi-step synthesis proceeding from commercially available 1-chloro-2-nitrobenzene by (i) base-mediated coupling (e.g., with sodium hydride) with a suitable substituted hydroxyalkylcarbonyl reagent in a suitable polar aprotic solvent (e.g., tetrahydrofuran or dioxane) or by reaction of 2-nitrophenol with a suitable substituted chloromethylcarbonyl reagent, (ii) reduction of the nitro group with a suitable reducing agent (e.g., hydrogen, palladium on carbon in a suitable polar protic solvent), (iii) diazotization (using a suitable diazotization reagent, e.g., tert-butyl nitrite (t-BuONO), boron trifluoride etherate (BF3-OEt2)) in a suitable polar aprotic solvent (e.g., dichloromethane (DCM), dimethoxyethane), (iv) reaction with acetic anhydride, and (v) liberation of the hydroxy group by base-mediated removal of the acetyl protecting group (e.g., with potassium carbonate in a polar protic solvent). The nitro group of compound (Ib) can then be reduced and then added to a halogen substituent (e.g., chlorine, bromine) via a Sandmeyer reaction, so that the desired substituted N-phenyluracil (Ic) can be obtained in this manner. In Scheme 4 below, Q and R 2 has the meaning of the present invention as described above. 3 is, by way of example and not limitation, fluorine, and R 4 is, by way of example and not limitation, chlorine or nitro, and R 1 , R 5 , R 6 , R 7 By way of example and not limitation, is hydrogen; X and Y are, by way of example and not limitation, oxygen; and G is, by way of example and not limitation, CH2.

[0077] [ka]

[0078] Thus, the intermediate (VI) obtained by the above method can be converted to the desired substituted N-phenyluracil (Id, R 4 = nitro). The intermediate (VIII) used for this purpose can be prepared by a multi-step synthesis, starting from commercially available 1-chloro-2-nitrobenzene or 2-nitrophenol, in a manner similar to the synthesis of intermediate (VII) described in Scheme 4. The nitro group of compound (Id) can then be reduced and subsequently converted to a halogen substituent (e.g., chlorine, bromine) by a Sandmeyer reaction, so that the desired substituted N-phenyluracil (Ie) can be obtained in this manner. In Scheme 5 below, Q and R 2 has the meaning of the present invention as described above. 3 is, by way of example and not limitation, fluorine, and R 4 is, by way of example and not limitation, chlorine or nitro, and R 1 , R 5 , R 6 , R 7 By way of example and not limitation, X is hydrogen; by way of example and not limitation, Y is sulfur; and G is, by way of example and not limitation, CH.

[0079] [ka]

[0080] In a first step, compound (III) is converted to an intermediate of type (IX) utilizing a suitable, optionally further substituted iodophenol using a suitable base in a suitable polar aprotic solvent (e.g., dioxane) or a suitable transition metal catalyst (e.g., tris(dibenzylideneacetone)dipalladium(0)) with a suitable ligand (e.g., 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene) and a suitable base (e.g., diisopropyl(ethyl)amine). The further substituted N-methyl-5-mercaptophenyl-1H-pyrimidine-2,4-dione intermediate (II) can then be converted to the desired compound of the present invention of general formula (If) in which X and Y are sulfur (S) (Scheme 6). In some cases, intermediate protection of the thiol group with a suitable protecting group may be required. Intermediate (IX) can then be reacted with variously substituted haloalkanecarboxylic acids using a suitable base. In Scheme 6 below, Q, R 2 , R 3 , and R 4 has the meaning of the present invention as described above. 1 , R 5 , R 6 , R 7 is, by way of example and not limitation, hydrogen, X and Y are, by way of example and not limitation, sulfur, and G is, by way of example and not limitation, CH. Additionally, for greater clarity, by way of example and not limitation, a reaction pathway using iodoacetate is depicted in Scheme 6 below. The equivalent haloalkanecarboxylic acid (halogen = bromine or chlorine) is suitable for coupling with intermediate (IX).

[0081] [ka] [Example]

[0082] Selected detailed synthetic examples for compounds of the present invention of general formula (I) are added below. The example numbers mentioned correspond to the numbered schemes in Tables I.1 to I.33 below. The chemical examples reported for the chemical examples described in the following sections are 1 H NMR, 13 C-NMR and 19F-NMR spectroscopic data ( 1 1H NMR at 400 MHz and 13 For C-NMR, 150 MHz and 19 F-NMR was obtained on a Bruker instrument at 375 MHz, solvents CDCl3, CD3OD or d6-DMSO, internal standard: tetramethylsilane (δ = 0.00 ppm), and the listed signals have the following meaning: br = broad; s = singlet; d = doublet; t = triplet; dd = doublet of doublets; ddd = doublet of doublet of doublets; m = multiplet; q = quartet; quint = quintet; sext = sextet; sept = septet; dq = doublet of quartets; dt = doublet of triplets. In the case of diastereomeric mixtures, either the significant signals for each of the two diastereomers or the characteristic signal of the major diastereomer are reported. The abbreviations used for chemical groups have, for example, the following meanings: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl.

[0083] Synthesis Examples: Example I.1-1: 2-Methoxyethyl [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy}acetate.

[0084] [ka]

[0085] To a solution of methyl glycol (0.012 g, 0.155 mmol) in 4 mL of dichloromethane was added [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy}acetic acid (0.060 g, 0.119 mmol), followed by 1-hydroxy-1H-benzotriazole hydrate (0.024 g, 0.155 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.030 g, 0.155 mmol), and 4-dimethylaminopyridine (10 mol%) in succession, and the mixture was stirred at room temperature overnight. The reaction mixture was purified by silica gel column chromatography using an n-heptane / ethyl acetate gradient. This gave 0.044 g (64% of theoretical yield) of 2-methoxyethyl [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy}acetate. 1 H-NMR (CDCl3 δ, ppm) 7.44-7.41 (m, 1H), 7.34-7.30 (m, 2H), 7.08 (d, 1H), 7.01-6.97 (m, 1H), 6.78-6.76 (m, 1H), 6.27 (s, 1H), 4.70 (s, 2H), 4.29-4.26 (m, 2H), 3.58-3.56 (m, 2H),3.50-3,49 (m, 3H), 3.35 (s, 3H).

[0086] Example I.2-1: 2-Methoxyethyl (2RS)-2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy}propanoate.

[0087] [ka]

[0088] To a solution of methyl glycol (0.011 g, 0.150 mmol) in 4 mL of dichloromethane was added (2RS)-2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy}propanoic acid (0.060 g, 0.116 mmol), followed by 1-hydroxy-1H-benzotriazole hydrate (0.023 g, 0.150 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.029 g, 0.150 mmol), and 4-dimethylaminopyridine (10 mol%) in succession, and the mixture was stirred at room temperature overnight. The reaction mixture was purified by silica gel column chromatography using an n-heptane / ethyl acetate gradient. This gave 0.056 g (80% theoretical yield) of 2-methoxyethyl (2RS)-2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy}propanoate. 1 H-NMR (CDCl3 δ, ppm) 7.43-7.40 (m, 1H), 7.32-7.28 (m, 2H), 7.10-6.95 (m, 2H), 6.76-6.72 (m, 1H), 6.27-6.26 (m, 1H), 4.79-4.73 (m, 1H), 4.32-4.22 (m, 2H), 3.56-3.53 (m, 2H), 3,49 (m, 3H), 3.33 (s, 3H), 1.51-1.50 (m, 3H).

[0089] Example I.7-176: (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy) cyanomethyl acetate.

[0090] [ka]

[0091] To a solution of glycolonitrile (0.027 g, 0.286 mmol) in 10 ml of dichloromethane was added (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (0.100 g, 0.205 mmol), followed by 1-hydroxy-1H-benzotriazole hydrate (0.041 g, 0.266 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.051 g, 0.266 mmol), and 4-dimethylaminopyridine (10 mol%), and the mixture was stirred at room temperature for 2 hours. Water and dichloromethane were added to the reaction mixture, the aqueous phase was repeatedly extracted with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by silica gel column chromatography using an n-heptane / ethyl acetate gradient, 0.095 g (79% of theoretical yield) of a colorless solid was obtained. 1 H-NMR (CDCl3δ, ppm) 7.39 (d, 1H), 7.18-7.12 (m, 1H), 7.11-7.03 (m, 2H), 6.94 (d, 1H), 6.68 (d, 1H), 6.29 (s, 1H), 4.76 (s, 2H), 4.74 (s, 2H), 3.50 (s, 3H).

[0092] Example I.7-71: tetrahydrofuran-2-ylmethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate.

[0093] [ka]

[0094] To a solution of tetrahydrofuran-2-ylmethanol (0.042 g, 0.412 mmol) in 15 ml of dichloromethane was added (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (0.160 g, 0.327 mmol), then successively 1-hydroxy-1H-benzotriazole hydrate (0.059 g, 0.383 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.073 g, 0.383 mmol) and 4-dimethylaminopyridine (10 mol %), and the mixture was stirred at room temperature for 2 hours. Water and dichloromethane were added to the reaction mixture, the aqueous phase was repeatedly extracted with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by silica gel column chromatography using an n-heptane / ethyl acetate gradient, 0.129 g (73% theoretical yield) of a colorless solid was obtained. 1 H-NMR (CDCl3δ, ppm) 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.04 (m, 1H), 7.01-6.97 (m, 1H), 6.92 (d, 1H), 6.77 (d, 1H), 6.28 (s, 1H), 4.70 (s, 2H), 4.21-4.18 (m, 1H), 4,13-4.05 (m, 2H), 3.83-3.73 (m, 2H), 3.50 (s, 3H), 2.04-1.83 (m, 3H), 1.59-1.52 (m, 1H).

[0095] Example I.7-276: (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)pyridin-2-ylmethyl acetate.

[0096] [ka]

[0097] To a solution of pyridin-2-ylmethanol (0.028 g, 0.258 mmol) in 10 ml of dichloromethane was added (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (0.100 g, 0.205 mmol), followed by 1-hydroxy-1H-benzotriazole hydrate (0.037 g, 0.239 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.046 g, 0.239 mmol), and 4-dimethylaminopyridine (10 mol%), and the mixture was stirred at room temperature for 2 hours. Water and dichloromethane were added to the reaction mixture, the aqueous phase was repeatedly extracted with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by silica gel column chromatography using an n-heptane / ethyl acetate gradient, 0.096 g (81% theoretical yield) of a colorless solid was obtained. 1 H-NMR (CDCl3δ, ppm) 8.57-8.55 (m, 1H), 7.66 (t, 1H), 7.32 (d, 1H), 7.26-7.21 (m, 2H), 7.14-7.08 (m, 2H), 7.02-6.94 (m, 2H), 6.75 (d, 1H), 6.24 (s, 1H), 5.28 (s, 2H), 4.77 (s, 2H), 3.48 (s, 3H).

[0098] Example I.7-183: 2-nitroethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate.

[0099] [ka]

[0100] To a solution of (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (0.150 g, 0.306 mmol) in 1.0 mL of toluene, 2-nitroethanol (0.139 g, 1.531 mmol), concentrated acetic acid (0.092 g, 1.531 mmol), and concentrated sulfuric acid (0.015 g, 0.153 mmol) were added successively, and the mixture was stirred under reflux at room temperature for 5 hours. The reaction mixture was left overnight and then stirred under reflux for an additional 5 hours. Water and dichloromethane were added to the reaction mixture, the aqueous phase was repeatedly extracted with dichloromethane, and the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by silica gel column chromatography with an n-heptane / acetone gradient and then further purification by silica gel column chromatography with an n-heptane / ethyl acetate gradient, 0.036 g (20% theoretical yield) of 2-nitroethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate was obtained. 1 H-NMR (CDCl3δ, ppm) 7.37 (d, 1H), 7.16-7.12 (m, 1H), 7.09-7.07 (m, 1H), 7.04-7.00 (m, 1H), 6.90 (d, 1H), 6.67 (d, 1H), 6.28 (s, 1H), 4.67 (s, 2H), 4.66-4.64 (m, 2H), 4.59-4.56 (m, 2H), 3.50 (s, 3H).

[0101] Example I.7-177: 1-cyanoethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate.

[0102] [ka]

[0103] To a solution of (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (0.160 g, 0.327 mmol) in 4.0 mL of acetonitrile, 4-dimethylaminopyridine (0.005 g, 0.039 mmol), potassium carbonate (0.056 g, 0.404 mmol), and 2-bromopropanenitrile (0.052 g, 0.389 mmol) were added successively, and the mixture was stirred at room temperature for 2 hours and then under reflux for 1 hour. 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. Purification by silica gel column chromatography using an n-heptane / ethyl acetate gradient, followed by drying of the resulting product under reduced pressure at 40°C, gave 0.160 g (95% theoretical yield) of 1-cyanoethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate. 1 H-NMR (CDCl3δ, ppm) 7.38 (d, 1H), 7.17-7.13 (m, 1H), 7.10-7.02 (m, 2H), 6.95-6.93 (m, 1H), 6.72-6.68 (m, 1H), 6.29 (d, 1H), 5.45-5.42 (m, 1H), 4.72 (s, 2H), 3.50 (s, 3H), 1.64-1.61 (m, 3H).

[0104] Example I.7-1: 2-Methoxyethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate.

[0105] [ka]

[0106] Under a nitrogen atmosphere, indium(III) chloride (2.599 g, 11.749 mmol) was added to ethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (5.520 g, 10.681 mmol) in 46.32 ml of 2-methoxyethanol, and the mixture was stirred at 115 °C for 3 hours. After cooling to room temperature, the reaction mixture was poured into water, ethyl acetate was added, the aqueous phase was repeatedly extracted with ethyl acetate, the combined organic phases were washed with saturated aqueous sodium chloride, the organic phase was dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by silica gel column chromatography using an n-heptane / ethyl acetate gradient, 5.150 g (88% theoretical yield) of a colorless solid was obtained. 1 H-NMR (CDCl3δ, ppm) 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.05 (m, 1H), 7.01-6.99 (m, 1H), 6.93-6.91 (m, 1H), 6.77 (d, 1H), 6.28 (s, 1H), 4.70 (s, 2H), 4.29-4.27 (m, 2H), 3.56-3.54 (m, 2H), 3.50 (s, 3H), 3.33 (s, 3H).

[0107] Example I.7-94: 1-Methoxypropan-2-yl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate.

[0108] [ka]

[0109] Under a nitrogen atmosphere, indium(III) chloride (0.116 g, 0.527 mmol) was added to 2-methoxyethyl (2-{1-2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (0.160 g, 0.293 mmol) in 4.0 ml of 1-methoxypropan-2-ol, and the reaction mixture was heated in a microwave reactor at 125° C. for 1.5 hours. After cooling to room temperature, the reaction mixture was poured into water, dichloromethane was added, the aqueous phase was repeatedly extracted with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography using an n-heptane / ethyl acetate gradient, 0.110 g (66% theoretical yield) of 1-methoxypropan-2-yl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate was obtained. 1 H-NMR (CDCl3δ, ppm) 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.04 (m, 1H), 7.01-6.96 (m, 1H), 6.93-6.90 (m, 1H), 6.79-6.76 (m, 1H), 6.28 (d, 1H), 5.16-5.12 (m, 1H), 4.65 (s, 2H), 3.50 (s, 3H), 3.44-3.36 (m, 2H), 3.33 (s, 3H), 1.23 (d, 3H).

[0110] Example I.6-1: 2-Methoxyethyl (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetate.

[0111] [ka]

[0112] To ethyl (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetate (100 mg, 0.19 mmol) in a microwave bath under argon were added 2-methoxyethanol (505 mg, 6.63 mmol) and indium(III) chloride (51.2 mg, 0.23 mmol). The reaction mixture was stirred at 115° C. for 120 minutes under microwave conditions. After cooling to room temperature, the reaction mixture was stirred with 50 mL of water and 10 mL of dichloromethane was added. The organic phase was removed and concentrated. The crude product obtained was purified by silica gel column chromatography using an n-heptane / ethyl acetate gradient to give 2-methoxyethyl (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetate (78 mg, 73% theoretical yield) in the form of a colorless oil. 1 H-NMR (CDCl3δ, ppm) 7.87 (d, 1H), 7.19 (m, 2H), 7.03 (t, 1H), 6.95 (d, 1H), 6.88 (d, 1H), 6.28 (s, 1H), 4.67 (s, 2H), 4.25 (t, 2H), 3.53 (t, 2H), 3.50 (s, 3H), 3.31 (s, 3H).

[0113] Example I.6-176: (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy) cyanomethyl acetate.

[0114] [ka]

[0115] Under argon, a first charge of (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetic acid (100 mg, 0.20 mmol) was stirred at room temperature for 2.5 hours with bromoacetonitrile (38 mg, 0.30 mmol) and triethylamine (30 mg, 0.30 mmol) in 1 mL of acetone. After TLC monitoring, additional bromoacetonitrile (13 mg, 0.10 mmol) was added, and the mixture was stirred at room temperature for another hour. The reaction mixture was concentrated, and 10 mL of water and 10 mL of dichloromethane were added. The organic phase was removed and concentrated. The crude product obtained was purified by silica gel column chromatography using an n-heptane / ethyl acetate gradient to give cyanomethyl (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetate (104 mg, 95% theoretical yield) in the form of a colorless oil. 1 H-NMR (CDCl3δ, ppm) 7.89 (d, 1H), 7.24-7.20 (m, 2H), 7.09 (dt, 1H), 6.92 (dd, 1H), 6.82 (d, 1H), 6.30 (s, 1H), 4.75 (s, 2H), 4.71 (s, 2H), 3.51 (s, 3H).

[0116] Example I.8-176: (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy) cyanomethyl acetate.

[0117] [ka]

[0118] Under argon, a first charge of (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-phenoxy}phenoxy)acetic acid (1.000 g, 1.86 mmol) was stirred at room temperature for 5 hours with bromoacetonitrile (337 mg, 2.81 mmol) and triethylamine (380 mg, 3.75 mmol) in 22 mL of dichloromethane. The mixture was left overnight, 10 mL of water was added, and the mixture was then stirred. The organic phase was removed and concentrated. The crude product obtained was purified by silica gel column chromatography using an n-heptane / ethyl acetate gradient to give cyanomethyl (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (598 mg, 55% theoretical yield) in the form of a colorless oil. 1 H-NMR (CDCl3δ, ppm) 7.55 (d, 1H), 7.18-7.03 (m, 3H), 6.95 (dd, 1H), 6.64 (d, 1H), 6.29 (s, 1H), 4.76 (s, 2H), 4.75 (s, 2H), 3.50 (s, 3H).

[0119] Example I.9-176: cyanomethyl (2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate.

[0120] [ka]

[0121] Under argon, a first charge of cyanomethyl (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-phenoxy}phenoxy)acetate (598 mg, 1.05 mmol) together with zinc cyanide (129 mg, 1.10 mmol) and tetrakis(triphenylphosphine)palladium(0) (121 mg, 0.10 mmol) in 15 ml of N,N-dimethylacetamide was stirred at 180 °C for 1 h. After TLC monitoring, the reaction mixture was added to 10 ml of water and extracted with ethyl acetate. The combined organic phases were washed twice with saturated sodium chloride solution, then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product obtained was purified by silica gel column chromatography using an n-heptane / ethyl acetate gradient to give cyanomethyl (2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (232 mg, 42% theoretical yield) in the form of a colorless oil. 1 H-NMR (CDCl3δ, ppm) 7.53 (d, 1H), 7.23 (m, 2H), 7.09 (dt, 1H), 6.90 (d, 1H), 6.68 (d, 1H), 6.29 (s, 1H), 4.75 (s, 2H), 4.71 (s, 2H), 3.50 (s, 3H).

[0122] Similarly to the preparative examples cited above and described where appropriate, and taking into consideration the general details associated with the preparation of substituted N-heterocyclyl- and N-heteroaryl tetrahydropyrimidinones, the compounds cited below are obtained:

[0123] [ka]

[0124] Table I.1: Preferred compounds of formula (I.1) are compounds I.1-1 to I.1-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.1-1 to I.1-406 of Table I.1 are therefore defined by the meaning of Q in Table 1, respectively, of entries No. 1 to 406.

[0125] [Table 3-1] [Table 3-2] [Table 3-3] [Table 3-4] [Table 3-5] [Table 3-6] [Table 3-7] [Table 3-8] [Table 3-9] [Table 3-10] [Table 3-11] [Table 3-12] [Table 3-13] [Table 3-14] [Table 3-15] [Table 3-16] [Table 3-17] [Table 3-18]

[0126] [ka]

[0127] Table I.2: Preferred compounds of formula (I.2) are compounds I.2-1 to I.2-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.2-1 to I.2-406 in Table I.2 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0128] [ka]

[0129] Table I.3: Preferred compounds of formula (I.3) are compounds I.3-1 to I.3-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.3-1 to I.3-406 in Table I.3 are therefore defined by the meaning of Q in Table 1, entries 1 to 406, respectively.

[0130] [ka]

[0131] Table I.4: Preferred compounds of formula (I.4) are compounds I.4-1 to I.4-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.4-1 to I.4-406 in Table I.4 are therefore defined by the meaning of Q in Table 1, entries 1 to 406, respectively.

[0132] [ka]

[0133] Table I.5: Preferred compounds of formula (I.5) are compounds I.5-1 to I.5-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.5-1 to I.5-406 in Table I.5 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0134] [ka]

[0135] Table I.6: Preferred compounds of formula (I.6) are compounds I.6-1 to I.6-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.6-1 to I.6-406 in Table I.6 are therefore defined by the meaning of Q in Table 1, entries 1 to 406, respectively.

[0136] [ka]

[0137] Table I.7: Preferred compounds of formula (I.7) are compounds I.7-1 to I.7-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.7-1 to I.7-406 of Table I.7 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0138] [ka]

[0139] Table I.8: Preferred compounds of formula (I.8) are compounds I.8-1 to I.8-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.8-1 to I.8-406 of Table I.8 are therefore defined by the meaning of Q in Table 1, entries 1 to 406, respectively.

[0140] [ka]

[0141] Table I.9: Preferred compounds of formula (I.9) are compounds I.9-1 to I.9-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.9-1 to I.9-406 of Table I.9 are therefore defined by the meaning of Q in Table 1, entries 1 to 406, respectively.

[0142] [ka]

[0143] Table I.10: Preferred compounds of formula (I.10) are compounds I.10-1 to I.10-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.10-1 to I.10-406 of Table I.10 are therefore defined by the meaning of Q in Table 1, entries 1 to 406, respectively.

[0144] [ka]

[0145] Table I.11: Preferred compounds of formula (I.11) are compounds I.11-1 to I.11-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.11-1 to I.11-406 of Table I.11 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0146] [ka]

[0147] Table I.12: Preferred compounds of formula (I.12) are compounds I.12-1 to I.12-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.12-1 to I.12-406 of Table I.12 are therefore defined by the meaning of Q in Table 1, entries 1 to 406, respectively.

[0148] [ka]

[0149] Table I.13: Preferred compounds of formula (I.13) are compounds I.13-1 to I.13-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.13-1 to I.13-406 of Table I.13 are therefore defined by the meaning of Q in Table 1, entries 1 to 406, respectively.

[0150] [ka]

[0151] Table I.14: Preferred compounds of formula (I.14) are compounds I.14-1 to I.14-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.14-1 to I.14-406 of Table I.14 are therefore defined by the meaning of Q in Table 1, respectively, entries No. 1 to 406.

[0152] [ka]

[0153] Table I.15: Preferred compounds of formula (I.15) are compounds I.15-1 to I.15-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.15-1 to I.15-406 of Table I.15 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0154] [ka]

[0155] Table I.16: Preferred compounds of formula (I.16) are compounds I.16-1 to I.16-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.16-1 to I.16-406 of Table I.16 are therefore defined by the meaning of Q in Table 1 of the respective entries No. 1 to 406.

[0156] [ka]

[0157] Table I.17: Preferred compounds of formula (I.17) are compounds I.17-1 to I.17-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.17-1 to I.17-406 of Table I.17 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0158] [ka]

[0159] Table I.18: Preferred compounds of formula (I.18) are compounds I.18-1 to I.18-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.18-1 to I.18-406 of Table I.18 are therefore defined by the meaning of Q in Table 1, entries 1 to 406, respectively.

[0160] [ka]

[0161] Table I.19: Preferred compounds of formula (I.19) are compounds I.19-1 to I.19-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.19-1 to I.19-406 of Table I.19 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0162] [ka]

[0163] Table I.20: Preferred compounds of formula (I.20) are compounds I.20-1 to I.20-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.20-1 to I.20-406 of Table I.20 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0164] [ka]

[0165] Table I.21: Preferred compounds of formula (I.21) are compounds I.21-1 to I.21-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.21-1 to I.21-406 of Table I.21 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0166] [ka]

[0167] Table I.22: Preferred compounds of formula (I.22) are compounds I.22-1 to I.22-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.22-1 to I.22-406 of Table I.22 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0168] [ka]

[0169] Table I.23: Preferred compounds of formula (I.23) are compounds I.23-1 to I.23-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.23-1 to I.23-406 of Table I.23 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0170] [ka]

[0171] Table I.24: Preferred compounds of formula (I.24) are compounds I.24-1 to I.24-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.24-1 to I.24-406 of Table I.24 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0172] [ka]

[0173] Table I.25: Preferred compounds of formula (I.25) are compounds I.25-1 to I.25-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.25-1 to I.25-406 of Table I.25 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0174] [ka]

[0175] Table I.26: Preferred compounds of formula (I.26) are compounds I.26-1 to I.26-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.26-1 to I.26-406 of Table I.26 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0176] [ka]

[0177] Table I.27: Preferred compounds of formula (I.27) are compounds I.27-1 to I.27-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.27-1 to I.27-406 of Table I.27 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0178] [ka]

[0179] Table I.28: Preferred compounds of formula (I.28) are compounds I.28-1 to I.28-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.28-1 to I.28-406 of Table I.28 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0180] [ka]

[0181] Table I.29: Preferred compounds of formula (I.29) are compounds I.29-1 to I.29-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.29-1 to I.29-406 of Table I.29 are therefore defined by the meaning of Q in Table 1, entries 1 to 406, respectively.

[0182] [ka]

[0183] Table I.30: Preferred compounds of formula (I.30) are compounds I.30-1 to I.30-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.30-1 to I.30-406 of Table I.30 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0184] [ka]

[0185] Table I.31: Preferred compounds of formula (I.31) are compounds I.31-1 to I.31-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.31-1 to I.31-406 of Table I.31 are therefore defined by the meaning of Q in Table 1, entries 1 to 406, respectively.

[0186] [ka]

[0187] Table I.32: Preferred compounds of formula (I.32) are compounds I.32-1 to I.32-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.32-1 to I.32-406 of Table I.32 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0188] [ka]

[0189] Table I.33: Preferred compounds of formula (I.33) are compounds I.33-1 to I.33-406, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.33-1 to I.33-406 of Table I.33 are therefore defined by the meaning of Q in Table 1, entries No. 1 to 406, respectively.

[0190] NMR data of selected examples: 1 H NMR data are described in two different ways: (a) by conventional NMR interpretation or (b) by the following method: 1 H NMR peak list format.

[0191] a) Conventional NMR interpretation Example I.7-23: 1 H-NMR (CDCl3δ, ppm): 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.04 (m, 1H), 7.01-6.99 (m, 1H), 6.94-6.91 (m, 1H), 6.77 (d, 1H), 6.28 (s, 1H), 4.69 (s, 2H), 4.31-4.29 (m, 2H), 3.69-3.67 (m, 2H), 3.61-3.59 (m, 2H), 3.52-3.50 (m, 2H), 3.37 (s, 3H).

[0192] Example I.7-121: 1H-NMR (CDCl3δ, ppm): 7.37 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.05 (m, 1H), 7.02-6.98 (m, 1H), 6.91 (d, 1H), 6.74-6.71 (m, 1H), 6.28 (s, 1H), 5.36-5.33 (m, 1H), 4.65 (s, 2H), 3.88-3.77 (m, 4H), 3.50 (s, 3H), 2.17-2.10 (m, 1H), 1.99-1.95 (m, 1H).

[0193] Example I.7-286: 1 H-NMR (CDCl3δ, ppm): 8.47 (d, 1H), 7.69 (d, 1H), 7.33 (d, 1H), 7.26-7.22 (m, 1H), 7.13-6.96 (m, 4H), 6.80 (d, 1H), 6.26 (s, 1H), 5.30 (s, 2H), 4.82 (s, 2H), 3.48 (s, 3H).

[0194] Example I.7-335: 1 H-NMR (CDCl3δ, ppm): 8.65 (s, 1H), 7.75 (d, 1H), 7.67 (d, 1H), 7.32 (d, 1H), 7.12 (t, 1H), 7.07 (d, 1H), 7.03 (t, 1H), 6.93 (d, 1H), 6.68 (d, 1H), 6.28 (s, 1H), 5.24 (s, 2H), 4.71 (s, 2H), 3.50 (s, 3H).

[0195] Example I.8-335: 1H-NMR (CDCl3δ, ppm): 8.65 (s, 1H), 7.75 (d, 1H), 7.66 (d, 1H), 7.47 (d, 1H), 7.13 (t, 1H), 7.08 (d, 1H), 7.04 (t, 1H), 6.93 (d, 1H), 6.65 (d, 1H), 6.29 (s, 1H), 5.24 (s, 2H), 4.71 (s, 2H), 3.50 (s, 3H).

[0196] Example I.9-367: 1 H-NMR (CDCl3δ, ppm): 7.46 (d, 1H), 7.22 (d, 1H), 7.15 (t, 1H), 7.07 (s, 1H), 7.03 (t, 1H), 6.85 (d, 1H), 6.80 (d, 1H), 6.25 (s, 1H), 5.19 (s, 2H), 4.68 (s, 2H), 3.48 (s, 3H), 2.69 (s, 3H).

[0197] Example I.23-365: 1 H-NMR (CDCl3δ, ppm): 7.86 (s, 1H), 7.69 (s, 1H), 7.37 (d, 1H), 6.94-6.90 (m, 1H), 6.84 (d, 1H), 6.81-6.73 (m, 2H), 6.30 (s, 1H), 5.13 (s, 2H), 4.67 (s, 2H), 3.52 (s, 3H).

[0198] Example I.23-367: 1 H-NMR (CDCl3δ, ppm): 7.36 (d, 1H), 7.11 (s, 1H), 6.95-6.90 (m, 1H), 6.86 (d, 1H), 6.79-6.74 (m, 2H), 6.29 (s, 1H), 5.23 (s, 2H), 4.68 (s, 2H), 3.51 (s, 3H), 2.71 (s, 3H).

[0199] Example I.20-176: 1H-NMR (CDCl3δ, ppm): 7.55 (d, 1H), 7.16-7.12 (m, 1H), 6.94-6.89 (m, 1H), 6.70-6.68 (m, 1H), 6.57 (d, 1H), 6.28 (s, 1H), 4.75 (s, 2H), 4.73 (s, 2H), 3.50 (s, 3H).

[0200] Example I.20-1: 1 H-NMR (CDCl3δ, ppm): 7.52 (d, 1H), 7.11-7.08 (m, 1H), 6.88-6.85 (m, 1H), 6.69 (d, 1H), 6.68-6.66 (m, 1H), 6.26 (s, 1H), 4.69 (s, 2H), 4-28-4.25 (m, 2H), 3.55-3.52 (m, 2H), 3.49 (s, 3H), 3.32 (s, 3H).

[0201] b) NMR peak list method Selected Examples 1 H NMR data, 1 The information is written in the form of a H NMR peak list. For each signal peak, first the δ value (ppm) is listed, followed by the signal intensity in parentheses. The δ value / signal intensity number pairs for different signal peaks are listed, separated from each other by semicolons.

[0202] Thus, the peak list for one embodiment is of the form: δ1(Intensity 1); δ2(Intensity 2);···;δ i (strength i );···;δ n (strength n )

[0203] The intensity of sharp signals correlates with the signal height (cm) in the printed example of the NMR spectrum, showing the ratio of signal intensities. In the case of broad signals, several peaks or centers of the signal and their relative intensities can be shown compared to the maximum intensity in the spectrum.

[0204] 1 For correction of chemical shifts in H NMR spectra, we use the chemical shifts of tetramethylsilane and / or the solvent, especially for spectra measured in DMSO. Thus, the tetramethylsilane peak may, but need not, be present in the NMR peak list.

[0205] 1 The 1 H NMR peak listing is similar to a conventional 1 H NMR printout and therefore includes all peaks that would normally be listed in a conventional NMR interpretation.

[0206] In addition, the conventional 1 Similar to the 1 H NMR printouts, these may show solvent signals, signals of stereoisomers of the target compounds that also form part of the subject matter of the present invention, and / or peaks of impurities.

[0207] In reporting compound signals within the δ range of the solvent and / or water, our 1 The list of H NMR peaks shows the usual solvent peaks, e.g., the DMSO peak in DMSO-D6, and the water peak, which usually have high intensities on average.

[0208] The peaks of stereoisomers of the target compound and / or impurity peaks typically have lower intensities on average than the peaks of the target compound (eg, have a purity of >90%).

[0209] Such stereoisomers and / or impurities may be unique to a particular manufacturing method, and thus, in this case, these peaks can be used to help identify the reproduction of our manufacturing method by reference to a "by-product fingerprint."

[0210] The expert who calculates the peaks of the target compounds by known methods (MestreC, ACD simulation, as well as empirically evaluated expected values) can isolate the peaks of the target compounds, if necessary, using additional intensity filters. This isolation is achieved by the conventional 1 This would be similar to relative peak picking in H NMR interpretation.

[0211] 1 Further details of the 1 H NMR peak list can be found in Research Disclosure Database No. 564025.

[0212] [Table 4-1] [Table 4-2] [Table 4-3] [Table 4-4] [Table 4-5] [Table 4-6] [Table 4-7] [Table 4-8] [Table 4-9] [Table 4-10] [Table 4-11] [Table 4-12] Table 4-13 Table 4-14 Table 4-15 Table 4-16 Table 4-17 Table 4-18 Table 4-19 Table 4-20 Table 4-21 Table 4-22 Table 4-23 Table 4-24 Table 4-25 Table 4-26 Table 4-27 Table 4-28 Table 4-29 Table 4-30 Table 4-31 Table 4-32 Table 4-33 Table 4-34 Table 4-35 Table 4-36 Table 4-37 Table 4-38 Table 4-39 Table 4-40 Table 4-41 Table 4-42 Table 4-43 Table 4-44 Table 4-45 Table 4-46 Table 4-47 Table 4-48 Table 4-49 Table 4-50 Table 4-51 Table 4-52 Table 4-53 Table 4-54 Table 4-55 Table 4-56 Table 4-57 Table 4-58 Table 4-59 Table 4-60 Table 4-61

[0213] The present invention further provides the use, preferably in one of the embodiments specified as preferred or particularly preferred, of one or more compounds of the invention of general formula (I) as defined above and / or salts thereof, in particular one or more compounds of formulae (I.1) to (I.33) as defined above and / or salts thereof, preferably in crops of useful plants and / or ornamental plants, as herbicides and / or plant growth regulators.

[0214] The present invention provides - preferably, in one embodiment, an effective amount of one or more compounds of the invention of general formula (I) as defined above and / or salts thereof, which are preferred or particularly preferred, in particular in each case one or more compounds of formulae (I.1) to (I.33) as defined above and / or salts thereof, or an effective amount of the composition of the present invention as defined below, on (harmful) plants, on the seeds of (harmful) plants, on the soil in or on which (harmful) plants grow, or on cultivated areas. Further provided is a method for controlling harmful plants and / or regulating plant growth, comprising:

[0215] The present invention provides - preferably, in one embodiment, an effective amount of one or more compounds of general formula (I) and / or salts thereof as defined above, which are preferred or particularly preferred, in particular one or more compounds of formulae (I.1) to (I.33) as defined above in each case and / or salts thereof, or an effective amount of the composition of the present invention as defined below, onto undesirable plants (e.g., noxious plants such as monocotyledonous or dicotyledonous weeds or undesirable crops), seeds of undesirable plants (i.e., plant seeds, e.g., grains, seeds, or vegetative propagation organs such as tubers or shoot parts bearing buds), soil in or on which undesirable plants grow (e.g., soil of crop or non-crop cultivation areas), or cultivated areas (i.e., areas where undesirable plants will grow). Also provided is a method for controlling undesirable plants, preferably in crops of useful plants, characterized by:

[0216] The present invention provides - preferably, in one embodiment, an effective amount of one or more compounds of general formula (I) and / or salts thereof as defined above, which are preferred or particularly preferred, in particular one or more compounds of formulae (I.1) to (I.33) as defined above in each case and / or salts thereof, or an effective amount of the composition of the present invention as defined below, onto plants, plant seeds (i.e., plant seeds, e.g., grains, seeds, or vegetative propagation organs such as tubers or shoot parts bearing buds), the soil in or on which the plants grow (e.g., agricultural or non-agricultural soil), or cultivated areas (i.e., areas where the plants will grow). Further provided is a control method for regulating the growth of plants, preferably useful plants, characterized by:

[0217] In this context, the compounds of the invention of general formula (I) or compositions of the invention can be deployed, for example, by pre-sowing treatment (where appropriate also by incorporation into the soil), pre-emergence and / or post-emergence methods. Without intending to limit the list to a particular species, some representative specific examples of monocotyledonous and dicotyledonous weed flowers that can be controlled by the compounds according to the invention are as follows:

[0218] In the method of the present invention for controlling harmful plants or regulating plant growth, one or more compounds of general formula (I) and / or salts thereof are used for controlling harmful plants or regulating the growth of harmful plants in crops of useful plants or ornamental plants, and in a preferred configuration, the useful plants or ornamental plants are preferably transgenic plants.

[0219] The compounds according to the invention of general formula (I) and / or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants: Harmful monocotyledonous plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitalia, Echinochloa, Eleocharis, Eleusine, Eragrostis , Eriochloa genus, Festuca genus, Fimbristylis genus, Heteranthera genus, Imperata genus, Ischaemum genus, Leptochloa genus, Lolium genus, Monochoria genus, Panicum genus, Paspalum genus, Phalaris genus, Phleum genus, Poa genus, Rottboellia genus, Sagittaria genus, Scirpus genus, Setaria genus, Sorghum genus. Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium Genus Chenopodium, Genus Cirsium, Genus Convolvulus, Genus Datura, Genus Desmodium, Genus Emex, Genus Erysimum, Genus Euphorbia, Genus Galeopsis, Genus Galinsoga, Genus Galium, Genus Hibiscus, Genus Ipomoea, Genus Kochia, Genus Lamium, Genus Lepi Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Lorice Genus Rorippa, genus Rotala, genus Rumex, genus Salsola, genus Senecio, genus Sesbania, genus Sida, genus Sinapis, genus Solanum, genus Sonchus, genus Sphenoclea, genus Stellaria, genus Taraxacum, genus Thlaspi, genus Trifolium, genus Urtica,Veronica, Viola, Xanthium.

[0220] When the compound of the present invention represented by general formula (I) is applied to the soil surface before the germination of harmful plants (weeds and / or broad-leaf weeds) (pre-emergence method), either the seedlings of the weeds or broad-leaf weeds are completely prevented from germinating, or they grow until they reach the cotyledon stage, but then stop growing and finally die completely after 3 to 4 weeks.

[0221] When the compounds of the invention of general formula (I) are applied post-emergence to the leaf parts of the plants, growth stops after treatment and the harmful plants remain in the vegetative stage at the time of application or die completely after a certain time, thus resulting in a very early and lasting elimination of competition by weeds that are harmful to the crop.

[0222] The compounds of the present invention of general formula (I) show significant herbicidal activity against monocotyledonous and dicotyledonous weeds, as well as against economically important crops, such as those of the genus Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, P. Dicotyledonous crops of the genera Haseolus, Pisum, Solanum, and Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, and Zea are only slightly or not at all damaged, depending on the structure and application rate of the compounds according to the invention. For these reasons, the compounds are highly suitable for selectively controlling undesired plant growth in crops such as agriculturally useful or ornamental plants.

[0223] In addition, the compounds of the present invention of general formula (I) (depending on their specific structure and the amount of application) have significant growth-regulating properties in crops. The compounds of the present invention interfere with the metabolism of the plant itself with a regulating effect, and can therefore be used to control the effects of plant components and promote harvesting, for example, by causing drought and growth inhibition. Furthermore, the compounds of the present invention are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plant in the process. Inhibition of vegetative growth plays a major role for many monocotyledonous and dicotyledonous crops, for example, because it can reduce or completely prevent lodging.

[0224] Due to these herbicidal and plant growth regulating properties, the compounds of the present invention of general formula (I) can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis.Generally, transgenic plants are characterized by certain advantageous properties, such as resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms, such as fungi, bacteria, or viruses.Other specific characteristics relate to the yield, for example, in terms of quantity, quality, storability, composition, and specific components.For example, there are known transgenic plants with high starch content or altered starch quality, or transgenic plants with different fatty acid compositions in the harvest.

[0225] The use of the compounds of the invention of general formula (I) and / or their salts in economically important transgenic crops of useful and ornamental plants, for example of cereals such as wheat, barley, rye, oat, millet, rice and maize, or of crops such as sugar beet, cotton, soybean, oilseed rape, potato, tomato, pea and other vegetables, is preferred from the standpoint of transgenic crops.

[0226] It is also preferred to use the compounds of the invention of general formula (I) as herbicides in crops of useful plants which are tolerant or have been made tolerant by recombinant means to the phytotoxic effects of herbicides.

[0227] Due to these herbicidal and plant growth regulating properties, the compounds of the present invention of general formula (I) can also be used to control harmful plants in crops of known or yet to be developed genetically modified plants. Generally, transgenic plants are characterized by certain advantageous properties, such as resistance to certain pesticides, particularly certain herbicides, resistance to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms, such as fungi, bacteria, or viruses. Other specific properties relate to the yield, for example, in terms of quantity, quality, storability, composition, and specific components. For example, there are known transgenic plants with high starch content or altered starch quality, or transgenic plants with different fatty acid compositions in the harvest. Another special property can be tolerance or resistance to abiotic stress factors, such as heat, cold, drought, salinity, and ultraviolet radiation.

[0228] It is preferred to use the compounds of the invention of general formula (I) and / or their salts in economically important transgenic crops of useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize, or crops such as sugar beet, cotton, soybean, oilseed rape, potato, tomato, pea and other vegetables.

[0229] It is preferred to use the compounds of general formula (I) as herbicides in crops of useful plants which are tolerant, or have been made tolerant by recombinant means, to the phytotoxic effects of herbicides.

[0230] Conventional methods for producing novel plants with modified properties compared to existing plants include, for example, traditional cultivation methods and the production of mutants. Alternatively, novel plants with altered properties can be produced with the aid of recombinant methods.

[0231] A large number of molecular biology techniques that can produce novel transgenic plants with modified properties are known to those skilled in the art. For such genetic manipulation, nucleic acid molecules that allow sequence variation by mutagenesis or recombination of DNA sequences can be introduced into plasmids. Standard methods can be used, for example, to perform base exchanges, remove subsequences, or add natural or synthetic sequences. To link DNA fragments to each other, adapters or linkers can be added to the fragments.

[0232] For example, plant cells with reduced activity of a gene product can be produced by expressing at least one corresponding antisense RNA, a sense RNA to obtain co-suppression, or by expressing at least one stably constructed ribozyme that specifically cleaves the transcript of the gene product.

[0233] To achieve this goal, it is possible to use DNA molecules that contain the entire coding sequence of a gene product, including any flanking sequences that may be present, and DNA molecules that contain only a portion of the coding sequence, provided that these portions are long enough to have an antisense effect in cells. It is also possible to use DNA sequences that are highly homologous to, but not completely identical to, the coding sequence of a gene product.

[0234] When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired compartment of plant cells.However, to achieve localization in a specific compartment, it is possible to link the coding region with a DNA sequence that ensures localization in a specific compartment.This type of sequence is known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227).Nucleic acid molecules can also be expressed in organelles of plant cells.

[0235] The transgenic plant cells can be regenerated by known techniques to give rise to whole plants. In principle, the transgenic plants can be of any desired plant species, i.e., dicotyledonous as well as monocotyledonous plants.

[0236] Transgenic plants can be obtained in this way, whose properties are altered by the overexpression, suppression or inhibition of a homologous (=native) gene or gene sequence or a heterologous (=foreign) gene or gene sequence.

[0237] It is preferred to use the compounds of the invention of general formula (I) in transgenic crops which are tolerant to growth regulators such as, for example, 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 sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and similar active compounds.

[0238] When the compounds of the present invention of general formula (I) are used in transgenic crops, not only do they produce the effects against harmful plants observed in other crops, but they also frequently produce effects that are specific to the application in the particular transgenic crop, such as a change or a specific broadening of the spectrum of weeds that can be controlled, a changed application rate that can be used for application, preferably a better integration possibility with herbicides to which the transgenic crop is resistant, and an effect on the growth and yield of the transgenic crop plants.

[0239] The present invention therefore also relates to the use of the compounds of the invention of general formula (I) and / or their salts as herbicides for the control of harmful plants in crops of useful plants or ornamental plants, optionally in transgenic crops.

[0240] Preferred is the use in cereals, here preferably maize, wheat, barley, rye, oats, millet or rice, by the pre-emergence or post-emergence method.

[0241] Also preferred is use in soybeans, by the pre-emergence or post-emergence method.

[0242] Uses according to the invention for controlling harmful plants or regulating plant growth also include cases where the compound of general formula (I) or a salt thereof is not produced from a precursor substance (a "prodrug") in the plant or in the soil until after application to the plant.

[0243] The present invention also provides the use of one or more active compounds of general formula (I) (defined below) or salts thereof or compositions of the present invention for controlling harmful plants or regulating plant growth, which comprises applying an effective amount of one or more active compounds of general formula (I) or salts thereof or compositions of the present invention to plants (optionally harmful plants together with useful plants), plant seeds, the soil in or on which plants grow, or cultivated areas. The present invention also provides a herbicidal and / or plant growth regulating composition, characterized in that the composition comprises: (a) preferably, in one embodiment, an effective amount of one or more compounds of general formula (I) and / or salts thereof as defined above, which are preferred or particularly preferred, in particular in each case one or more compounds of formulae (I.1) to (I.33) as defined above and / or salts thereof, and (b) one or more further substances selected from group (i) and / or (ii): (i) one or more further pesticidal active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. those not meeting general formula (I) as defined above), fungicides, safeners, fertilizers and / or growth regulators; (ii) one or more formulation adjuvants customary in crop protection.

[0244] The further pesticide active substances of component (i) of the composition of the present invention are preferably selected from the group of substances described in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Society of Chemistry, 2012.

[0245] The herbicidal or plant growth regulating compositions of the invention preferably comprise one, two, three or more formulation adjuvants (ii) customary in crop protection, selected from the group consisting of surfactants, emulsifiers, dispersants, film-forming agents, thickeners, inorganic salts, dusting agents, carriers that are solid at 25°C and 1013 mbar, preferably adsorbent granular inert substances, wetting agents, antioxidants, stabilizers, buffer substances, antifoaming agents, water, organic solvents, preferably organic solvents that are miscible with water in all proportions at 25°C and 1013 mbar.

[0246] The compounds of the present invention of general formula (I) can be used in the form of wettable powders, emulsifiable concentrates, sprayable liquids, dusts or granules in conventional formulations.Accordingly, the present invention also provides herbicidal and plant growth regulating compositions comprising the compounds of general formula (I) and / or their salts.

[0247] The compound of the present invention of general formula (I) and / or its salt can be formulated in various ways to define biological and / or physicochemical parameters.Possible formulations include, for example, wettable powders (WP), water-soluble powders (SP), solutions, emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water and water-in-oil emulsions, spray solutions, flowable formulations (SC), oil-in-water dispersions, oil-mixed solutions, microcapsules (CS), dusts (DP), fertilizers, granules for spraying and soil application, granules in the form of microgranules (GR), spray granules, absorbing and adsorbing granules, water-dispersible granules (WG), water-soluble granules (SG), micro-dusts, microcapsules and waxes.

[0248] These individual formulations and formulation aids such as inert substances, surfactants, solvents and further additives are known to those skilled in the art and can be found, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ; Hv Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, NY; C. Marsden, "Solvents Guide", 2nd ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.

[0249] Wettable powders are formulations that can be uniformly dispersed in water in addition to the active ingredient, excluding diluents or inert substances, and also contain ionic and / or nonionic surfactants (wetting agents, dispersants), such as polyoxyethylenated alkylphenols, polyoxyethylenated fatty alcohols, polyoxyethylenated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyl tartrate. To prepare wettable powders, the active herbicidal ingredient is finely ground using customary equipment, such as a hammer mill, blower mill, or air-jet mill, and simultaneously or subsequently mixed with formulation adjuvants.

[0250] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of relatively high-boiling aromatic compounds or hydrocarbons or organic solvents, with the addition of one or more ionic and / or nonionic surfactants (emulsifying agents). Examples of emulsifiable concentrates that may be used are: calcium salts of alkali arylsulfonic acids, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiable concentrates such as fatty acid polyglycols, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.

[0251] Dusts are obtained by grinding the active ingredient with finely divided solid matter, for example talc, kaolin, natural clays such as bentonite and pyrophyllite, or diatomaceous earth.

[0252] Flowable formulations can be water-based or oil-based and can be prepared, for example, by wet milling using standard commercial bead mills and, if necessary, by adding surfactants, for example, as already mentioned above for other formulation types.

[0253] Emulsion formulations, e.g., oil-in-water emulsion formulations (EW), can be formulated, for example, by means of a stirrer, colloid mill and / or static mixer using aqueous organic solvents and, if necessary, surfactants, as already mentioned above for other formulation types.

[0254] Granules can be prepared either by spraying the active ingredient onto a granular inert material capable of adsorbing it, or by spreading an active ingredient concentrate on the surface of a carrier material such as sand, kaolinite, or a granular inert material with the aid of a binder such as polyvinyl alcohol, sodium polyacrylate, or mineral oil. The appropriate active ingredient can also be ground in the usual manner for preparing fertilizer granules, if necessary as a mixture with fertilizer.

[0255] Water dispersible granules are generally produced by conventional methods such as spray drying, fluidized bed granulation, pan granulation, mixing with high speed mixers and extrusion without the use of solid inert materials.

[0256] For the preparation of pan, fluidized bed, extruder and spray granules, see, for example, the methods in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff.; "Perry's Chemical Engineer's Handbook", 5th ed., McGraw-Hill, New York 1973, pp. 8-57.

[0257] For further details regarding the formulation of crop protection compositions, see, for example, G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0258] The pesticide formulation, preferably the herbicide or plant growth regulator composition, of the present invention preferably contains a total amount of the active ingredient of general formula (I) and its salt of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, particularly preferably 1 to 90% by weight, more preferably 2 to 80% by weight.

[0259] In wettable powders, the active ingredient concentration is, for example, about 10% to 90% by weight, with the remainder up to 100% being made up of customary formulation ingredients. In emulsifiable concentrates, the active ingredient concentration can be about 1% to 90% by weight, preferably 5% to 80% by weight. Formulations in dust form contain 1% to 30% by weight of the active ingredient, preferably usually 5% to 20% by weight; sprayable liquids contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of the active ingredient. In the case of water dispersible granules, the active ingredient content depends in part on whether the active ingredient is liquid or solid, and the use of granulation aids, filters, etc. In water dispersible granules, the active ingredient content is, for example, 1% to 95% by weight, preferably 10% to 80% by weight.

[0260] In addition, the active ingredient formulations described may optionally contain the usual spreading agents, wetting agents, dispersing agents, emulsifying agents, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, antifoaming agents, evaporation inhibitors and agents that influence pH and viscosity. Examples of formulation adjuvants are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).

[0261] The compounds of the present invention of general formula (I) and their salts can be used, for example, in the form of final formulations or tank mixes, either by themselves or in the form of formulations in combination with other pesticides, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators. Based on the above formulations, complex formulations can be prepared taking into account the physical properties and stability of the active ingredients to be combined.

[0262] Combination partners that can be used for the compounds of the present invention of general formula (I) in mixed formulations or tank mixes are known active ingredients based on, for example, the inhibition of acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enoylpyruvinylshikimate-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 "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the references cited therein.

[0263] The selective control of harmful plants in useful plant crops and ornamental plants is particularly interesting.The compounds of the present invention of general formula (I) have already demonstrated excellent selectivity for most crops, primarily for some crops, especially when mixed with other less selective herbicides, but phytotoxicity to crops may occur.In this regard, the combination of the compounds of the present invention of general formula (I) is particularly interesting is the combination comprising compound (I) or its combination with other herbicides or insecticides and safeners.The safener used in an effective amount of detoxification reduces the phytotoxic side effects of herbicides / insecticides used in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugarcane, rapeseed, cotton and soybean, preferably cereals.

[0264] The weight ratio of herbicide to safener (mixture) generally depends on the herbicide application rate and the efficacy of the safener in question and can vary widely, for example, from 200:1 to 1:200, preferably from 100:1 to 1:100, in particular from 20:1 to 1:20. As with the compounds of general formula (I) or mixtures thereof, the safener can be formulated with further herbicides / insecticides and can be provided and used as a final formulation or tank mix with the herbicide.

[0265] For application, the commercially available herbicide or herbicide / safener formulations are diluted, if necessary, in the usual manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water dispersible granules. Formulations in dust form, granules for soil application or granules for application and spraying liquids are usually not further diluted with other inert substances before application.

[0266] The application rate of the compounds of the present invention of general formula (I) and / or their salts is influenced to some extent by external conditions such as temperature, humidity, etc. The application rate can vary widely. For application as a herbicide to control harmful plants, the total amount of the compounds of the present invention of general formula (I) and / or their salts is preferably in the range of 0.001 to 10.0 kg / ha, more preferably in the range of 0.005 to 5 kg / ha, more preferably in the range of 0.01 to 1.5 kg / ha, and particularly preferably in the range of 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence applications.

[0267] When the compounds of the present invention of general formula (I) and / or their salts are used as plant growth regulators, for example as stem stabilizers for crops similar to those mentioned above, preferably cereal plants such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range of 0.001 to 2 kg / ha, preferably in the range of 0.005 to 1 kg / ha, in particular in the range of 10 to 500 g / ha, very particularly preferably in the range of 20 to 250 g / ha. This applies to both pre-emergence and post-emergence application.

[0268] Application as a stem stabilizer may be carried out at various stages of plant development, preferably after the tillering stage, for example at the beginning of vertical growth.

[0269] Alternatively, plant growth regulators can be applied by seed treatment, using a variety of techniques for dry and wet seed dressing. The application rate depends on the specific technique and can be determined in preliminary tests.

[0270] Combination partners that can be used for the compound of formula (I) of the present invention in the composition (e.g., mixed formulation or tank mix) of the present invention are known active ingredients, for example, based on the inhibition of acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enoylpyruvinylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, or protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Society of Chemistry, 2012, and the references cited therein. Known herbicides or plant growth regulators that can be combined with the compound of the present invention include, for example, the following, and the active ingredients are represented by their "common names" or chemical names or code numbers according to the International Organization for Standardization (ISO): These always include all use forms, eg acids, salts and all isomers, such as stereoisomers and optical isomers, even if these are not explicitly mentioned.

[0271] Examples of such herbicide mixing partners are: Acetochlor, acifluorfen, acifluorfen sodium, aclonifen, alachlor, aridchlor, alloxydim, alloxydim sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor potassium, aminocyclopyrachlor methyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asuram, atto azalazine, azafenidine, azimsulfuron, beflubutamide, benazolin, benazolin ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron methyl, bensulide, bentazon, benzobicyclon, benzofenap, bicyclopyrone, bifenox, viranaphos, viranaphos sodium, bispyribac, bispyribac sodium, bromacil, bromobutide, bromofenoxime, bromoxynil, bromoxynil butyrate, bromoxynil potassium, bromoxynil heptanoate and bromoxynil octanoate, Busoxinone, butachlor, butafenacil, butamiphos, butenachlor, butralin, butroxydim, butyrate, cafenstrole, carbetamide, carfentrazone, carfentrazone ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac sodium, chlorfenprop, chlorflurenol, chlorflurenol methyl, chloridazon, chlorimuron, chlorrimuron ethyl, chlorphthalim, chlorotoluron, chlorthal dimethyl, chlorsulfuron, cinidon, cinidon ethyl, cinmethylin , cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop butyl, ciprazine, 2,4-D, 2,4-D butotyl, 2,4-D butyl, 2,4-D dimethylammonium salt, 2,4-D diolamine, 2,4-D ethyl, 2,4-D 2-ethylhexyl, 2,4-D isobutyl, 2,4-D isooctyl, 2,4-D isopropylammonium, 2,4-D potassium salt, 2,4-D triisopropanolammonium and 2,4-D triolamine, 2,4-DB, 2,4-DB butyl, 2,4-DB dimethylammonium salt, 2,4-DB isooctyl, 2,4-DB potassium salt and 2,4-DB sodium salt, dymron, dalapon, dazomet, n-decanol, Desmedipham, detosylpyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufeni Can, diflufenzopyr, diflufenzopyr sodium, dimefron, dimepiperate, dimethachlor, dimethametrin, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamide, diquat, diquat dibromide, dithiopyr, diuron, DNOC, endothall, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, etiodin, etho Fumesate, ethoxyphene, ethoxyphene ethyl, ethoxysulfuron, etobenzanide, F-9600, F-5231, i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-2-yl]phenyl]ethanesulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone sodium, flucetosulfuron, fluchloralin, flufe Nacet, flufenpyr, flufenpyr ethyl, flumetsulam, flumiclorac, flumiclorac pentyl, flumioxazin, fluometuron, flurenol, flurenol butyl, flurenol dimethylammonium salt and flurenol methyl, fluroglicofen, fluroglicofen ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron methyl sodium salt, fluridone, flurochloridone, fluroxypyr, fluroxypyr meptyl, flurtamone, fluthiacet, flu Thiacetmethyl, Fomesafen, Fomesafen Sodium, Foramsulfuron, Fosamine, Glufosinate, Glufosinate Ammonium Salt, Glufosinate-P-Sodium Salt, Glufosinate-P-Ammonium Salt, Glufosinate-P-Sodium Salt, Glyphosate, Glyphosate Ammonium Salt, Glyphosate Isopropylammonium Salt, Glyphosate Diammonium Salt, Glyphosate Dimethylammonium Salt, Glyphosate Potassium Salt, Glyphosate Sodium Salt and Glyphosate Trimesium phosphate, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropyl phosphoramidothioate, haloxifen, haloxifen methyl, halosafen, halosulfuron, halosulfuron methyl, haloxyfop, haloxyfop-P, haloxyfop ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e., 1-(dimethoxyphosphoryl)ethyl (2,4-Dichlorophenoxy)acetate, imazamethabenz, imazamethabenz methyl, imazamox, imazamox ammonium salt, imazapic, imazapic ammonium salt, imazethapyr, imazethapyr immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron methyl sodium, ioxynil, ioxynil octanoate, ioxynil potassium and ioxynil sodium, ipfencarbasone, isoproturon, isouron, isoxabet methylpropanol, isoxaflutole, carbutyrate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, renecyl, linuron, MCPA, MCPA butotyl, MCPA dimethylammonium, MCPA-2-ethylhexyl, MCPA isopropylammonium, MCPA potassium, and MCPA sodium sodium, MCPB, MCPB methyl, MCPB methyl, MCPB ethyl and MCPB sodium, mecoprop, mecoprop sodium and mecoprop butotyl, mecoprop-P, mecoprop-P butotyl, mecoprop dimethylammonium, mecoprop-2-ethylhexyl and mecoprop potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazolam Sulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metoslam, metoxuron, metribuzin, metsulfuron, metsulfuron methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, i.e., N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., 4-(2,4-Dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, nebron, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pentoxamide, petroleum, phenmedipham, picloram, picloram Corinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolinate (pyrazolate), pyrazosulfuron phenanthrene, pyrazosulfuron ethyl, pyrazoxifen, pyribambenz, pyribambenzisopropyl, pyribambenzpropyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulf ron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron methyl, sulfosulfuron, SYN-523, SYP-249, i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thiooxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA sodium salt, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone methyl, thifensulfuron, thifensulfuron methyl, thiobencarb, thiafenacil, tolpyralate, topramezone, tralkoxy Dim, triafamone, triallate, trisulfuron, triaziflam, tribenuron, tribenuron methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron sodium, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:

[0272] [ka]

[0273] Examples of plant growth regulators as possible mixing partners are: Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, daminozide, dikegulac sodium, endothal, endothal dipotassium salt, endothal disodium salt, and endothal mono(N,N-dimethylalkylammonium) salt, ethephon, flumetralin, flurenol, flurenol butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (I AA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, n-phenylphthalamic acid, prohexadione calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, and uniconazole-P.

[0274] Useful combinations for the compounds of the present invention of general formula (I) include, for example, the following safeners: S1) Compounds from the group of heterocyclic carboxylic acid derivatives: S1 a ) Dichlorophenylpyrazoline-3-carboxylic acid type compounds (S1 a ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) (“mefenpyr diethyl”) and related compounds described in WO 91 / 07874; S1b ) Derivatives of dichlorophenylpyrazolecarboxylic acid (S1 b ), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4) and related compounds described in EP-A-333131 and EP-A-269806; S1 c ) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c ), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds described in EP 268554; S1 d ) Triazole carboxylic acid type compounds (S1 d ), preferably compounds such as fenchlorazole (ethyl ester), i.e., ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (S1-7), and related compounds described in EP 174562 and EP 346620; S1 e ) 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type compounds (S1 e), preferably ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds described in WO 91 / 08202, or compounds such as 5,5-diphenyl-2-isoxazolinecarboxylic 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) described in WO 95 / 07897.

[0275] S2) Compounds (S2) from the group of 8-quinolinoxy derivatives: S2 a ) 8-Quinolineoxyacetic acid type compounds (S2 a), preferably 1-methylhexyl (5-chloro-8-quinolinoxy)acetate (“cloquintocet-mexyl”) (S2-1), 1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), methyl (5-chloro-8-quinolinoxy)acetate (S2-6), allyl (5-chloro-8-quinolinoxy)acetate (S2-7), 2-(2-propylidene) (5-chloro-8-quinolinoxy)acetate minoxy)-1-ethyl (S2-8), (5-chloro-8-quinolinoxy)acetic acid 2-oxoprop-1-yl (S2-9) and related compounds described in EP 86750, EP 94349, EP 191736 or EP 0492366, further (5-chloro-8-quinolinoxy)acetic acid (S2-10) described in WO 2002 / 34048, its hydrates and salts, for example its lithium salt, sodium salt, potassium salt, calcium salt, magnesium salt, aluminum salt, iron salt, ammonium salt, quaternary ammonium salt, sulfonium salt or phosphonium salt; S2 b )(5-chloro-8-quinolinoxy)malonic acid type compounds (S2 b ), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methylethyl (5-chloro-8-quinolinoxy)malonate and related compounds described in EP 0 582 198.

[0276] S3) Active ingredients of the dichloroacetamide type (S3), often used as pre-emergence safeners (soil-acting safeners), e.g. "Dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), Stauffer's "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2), Stauffer's "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), PPG Industries' "PPG-1292" (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) (S3-5), Sagro-Chem's "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6), Nitrokemia or Monsanto's "AD-67" or "MON4660" (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (S3-7); TRI-Chemical RT's "TI-35" (1-dichloroacetylacepane) (S3-8), "Diclonon" (Dicyclonon) or "BAS145138" or "LAB145138" (S3-9), BASF's ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one), "Furilazol" or "MON13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), and its (R) isomer (S3-11).

[0277] S4) Compounds from the class of acylsulfonamides (S4): S4 a ) Formula (S4 a ):

[0278] [ka]

[0279] During the ceremony: R A 1 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, the two latter radicals being selected from the group halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio; A substituted by substituents, which in the case of cyclic radicals are substituted by (C1-C4)-alkyl and (C1-C4)-haloalkyl; R A 2 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3; mA is 1 or 2; v A is 0, 1, 2 or 3 N-acylsulfonamides and salts thereof; S4 b ) Formula (S4 b ):

[0280] [ka]

[0281] During the ceremony: R B 1 , R B 2 are independently hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, R B 3 is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, or (C1-C4)-alkoxy, m B is either 1 or 2, 4-(benzoylsulfamoyl)benzamide type compounds and salts thereof, such as R B1 = cyclopropyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe ("cyprosulfamide", S4-1), R B 1 = cyclopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe (S4-2), R B 1 = ethyl, R B 2 = hydrogen and (R B 3 )=2-OMe(S4-3), R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe (S4-4), and R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 )=2-OMe(S4-5) What is; S4 c ) Formula (S4 c ):

[0282] [ka]

[0283] During the ceremony: R C 1 , R C 2 are independently hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, R C3 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3, m C is either 1 or 2, Compounds from the class of benzoylsulfamoylphenylureas; for example, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; S4 d ) For example, the formula (S4 d ):

[0284] [ka]

[0285] During the ceremony: R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3; m D is 1 or 2; R D 5 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl, N-phenylsulfonylterephthalamide type compounds and salts thereof.

[0286] S5) Active ingredients (S5) from hydroxyaromatic compounds and aromatic-aliphatic carboxylic acid derivatives, such as, for example, ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO 2004 / 084631, WO 2005 / 015994, WO 2005 / 016001.

[0287] S6) Active ingredients (S6) from the class of the 1,2-dihydroquinoxalin-2-ones, such as 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO 2005 / 112630.

[0288] S7) Compounds (S7) from the class of diphenylmethoxyacetic acid derivatives, such as methyl diphenylmethoxyacetate (CAS registration number 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid, as described in WO 98 / 38856.

[0289] S8) Compounds of formula (S8) described in WO 98 / 27049:

[0290] [ka]

[0291] where the symbols and subscripts are defined as follows: R D 1 is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, R D 2 is hydrogen or (C1-C4)-alkyl, R D 3 is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, each of the aforementioned carbon-containing radicals being unsubstituted or substituted by one or more, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy; or a salt thereof, n D is an integer between 0 and 2.

[0292] S9) Active ingredients (S9) from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones, such as 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Registry Number: 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Registry Number: 95855-00-8), as described in WO 1999 / 000020.

[0293] S10) Formula (S10) described in WO 2007 / 023719 and WO 2007 / 023764 a ) or (S10 b ) compounds:

[0294] [ka]

[0295] During the ceremony: R E 1 is halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3, Y E , Z E are independently O or S, n E is an integer from 0 to 4, RE 2 is (C1~C 16 )-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl; benzyl, halobenzyl, R E 3 is hydrogen or (C1-C6)-alkyl.

[0296] S11) Active ingredients of the oxyimino compound type (S11) known as seed dressing agents, for example: "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for foxtail millet / sorghum against metolachlor damage; Fluxofenim (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a seed dressing safener for foxtail millet / sorghum against metolachlor damage, and "Siometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), known as a seed dressing safener for foxtail millet / sorghum against metolachlor damage.

[0297] S12) Active ingredients (S12) from the class of isothiochromanones, for example, methyl [3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS registration number 205121-04-6) (S12-1) from WO 1998 / 13361 and related compounds.

[0298] S13) One or more compounds from group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for corn against thiocarbamate herbicide damage; "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in seeded rice; Flurazole (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), known as a seed dressing safener for foxtail millet / sorghum against alachlor and metolachlor damage; "CL304415" (CAS registration number 31541-57-8) American Cyanamid's (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4), a known safener for corn against imidazolinone damage; "MG191" (CAS Registry Number 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5), known as a safener for corn; "MG838" (CAS registration number 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6), "Disulfoton" (O,O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7), "Dietholate" (O,O-diethyl O-phenylphosphorodithioate) (S13-8), "Mefenate" (4-chlorophenylmethylcarbamate) (S13-9).

[0299] S14) Active ingredients that have a herbicidal effect on harmful plants as well as a mitigating effect on crops such as rice, e.g. "Dimepiperate" or "MY-93" (S-1-methyl 1-phenylethylpiperidine-1-carbothioate), known as a safener for rice against damage caused by the herbicide molinate; "Dymron" or "SK23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), known as a safener for rice against damage caused by the herbicide imazosulfuron; "Cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60-087254), which is known as a safener for rice against damage caused by some herbicides; "Methoxyphenone" or "NK049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage caused by some herbicides; Kumiai's "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) (CAS Registry Number 54091-06-4) is known as a safener for some herbicide damage in rice.

[0300] S15) Compounds of formula (S15) as described in WO 2008 / 131861 and WO 2008 / 131860 or tautomers thereof:

[0301] [ka]

[0302] During the ceremony: R H 1 is a (C1-C6)-haloalkyl radical, R H 2 is hydrogen or halogen, R H 3 , R H 4 are independently hydrogen, (C1 to C 16 )-Alkyl, (C2-C 16 )-alkenyl or (C2-C 16 )-alkynyl, each of the three latter radicals is selected from halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)-cycloalkyl, unsubstituted or substituted phenyl, and unsubstituted or substituted heterocyclyl; or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl fused on one side to a 4- to 6-membered saturated or unsaturated monocyclic ring, or (C4-C6)-cycloalkenyl fused on one side to a 4- to 6-membered saturated or unsaturated monocyclic ring, each of the four latter radicals is halogen, hydroxy, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)-cycloalkyl, unsubstituted or substituted phenyl and unsubstituted or substituted heterocyclyl, or R H 3 is (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy, R H 4 is hydrogen or (C1-C4)-alkyl, or R H 3and RH4 together and directly attached to the nitrogen atom form a 4- to 8-membered heterocyclic ring which, as well as the nitrogen atom, may contain further ring heteroatoms, preferably up to two further ring heteroatoms from the group N, O and S, and which are unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio.

[0303] S16) Active ingredients primarily used as herbicides but also having a safener effect on crops, e.g. (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloroethyl).

[0304] Preferred safeners in combination with the compounds of the invention of general formula (I), in particular the compounds of formulae (I.1) to (I.34) and / or salts thereof, are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.

[0305] Biological Examples: A. Post-emergence herbicidal activity and crop compatibility Seeds of monocotyledonous and dicotyledonous weeds and crops were sown in sandy loam, plastic, or wood fiber pots, covered with soil, and cultivated in a greenhouse under controlled growth conditions. Two to three weeks after sowing, the test plants were treated at the single-leaf stage. The compounds of the present invention, formulated as wettable powders (WP) or emulsifiable concentrates (EC), were then sprayed onto the leaves of the plants as aqueous suspensions or emulsions with a 0.5% additive at a water application rate of 600 l / ha (equivalent). After the test plants were maintained in the greenhouse for approximately three weeks under optimal growth conditions, the activity of the formulations was visually assessed in comparison with untreated controls. For example, 100% activity = plants killed; 0% activity = similar to control plants.

[0306] Tables A1 to A14 below show the efficacy of selected compounds of general formula (I) according to Tables I.1 to I.33 against various harmful plants and at application rates equivalent to 20 g / ha or less, obtained by the experimental method embodied above. Appendices "a", "b" and "c" differentiate between different dosages, otherwise the same harmful plants tested.

[0307] [Table 5-1] [Table 5-2] [Table 5-3] [Table 5-4]

[0308] [Table 6-1] [Table 6-2] [Table 6-3] [Table 6-4] Table 6-5

[0309] Table 7-1 Table 7-2 Table 7-3 Table 7-4 Table 7-5

[0310] Table 8

[0311] Table 9-1 Table 9-2 Table 9-3

[0312] Table 10-1 Table 10-2 Table 10-3 Table 10-4

[0313] Table 11-1 Table 11-2 Table 11-3 Table 11-4

[0314] Table 12-1 Table 12-2 Table 12-3 Table 12-4 Table 12-5

[0315] Table 13-1 Table 13-2 Table 13-3 Table 13-4 Table 13-5

[0316] Table 14

[0317] Table 15-1 Table 15-2 Table 15-3

[0318] Table 16-1 Table 16-2

[0319] Table 17-1 Table 17-2 Table 17-3 Table 17-4

[0320] Table 18-1 Table 18-2 Table 18-3 Table 18-4

[0321] Table 19

[0322] Table 20-1 Table 20-2

[0323] Table 21-1 Table 21-2

[0324] Table 22-1 Table 22-2 Table 22-3 Table 22-4

[0325] Table 23-1 Table 23-2 Table 23-3 Table 23-4 Table 23-5

[0326] Table 24-1 Table 24-2 Table 24-3 Table 24-4

[0327] Table 25-1 Table 25-2 Table 25-3 Table 25-4 Table 25-5

[0328] Table 26-1 Table 26-2 Table 26-3 Table 26-4 Table 26-5

[0329] Table 27

[0330] Table 28-1 Table 28-2 Table 28-3

[0331] Table 29-1 Table 29-2 Table 29-3 Table 29-4

[0332] Table 30-1 Table 30-2 Table 30-3 Table 30-4

[0333] Table 31-1 Table 31-2 Table 31-3 Table 31-4 Table 31-5

[0334] Table 32-1 Table 32-2 Table 32-3 Table 32-4 Table 32-5

[0335] Table 33-1 Table 33-2 Table 33-3 Table 33-4

[0336] Table 34-1 Table 34-2 Table 34-3 Table 34-4 Table 34-5

[0337] Table 35-1 Table 35-2 Table 35-3 Table 35-4 Table 35-5

[0338] Table 36-1 Table 36-2 Table 36-3 Table 36-4

[0339] Table 37-1 Table 37-2 Table 37-3 Table 37-4 Table 37-5

[0340] Table 38-1 Table 38-2 Table 38-3 Table 38-4 Table 38-5

[0341] Table 39

[0342] Table 40

[0343] Table 41

[0344] Table 42

[0345] Table 43

[0346] Tables A15 to A19 below show the crop suitability of selected compounds of general formula (I) according to Tables I.1 to I.33 at application rates equivalent to 5 g / ha or less, which was observed in tests following the experimental procedure described above. The observed effects on this selected crop are reported here (% values) compared to the untreated control. Appendices "a", "b" and "c" differentiate between different doses tested on otherwise the same crop.

[0347] [Table 44]

[0348] [Table 45]

[0349] [Table 46]

[0350] [Table 47-1] [Table 47-2] [Table 47-3]

[0351] [Table 48]

[0352] [Table 49]

[0353] [Table 50-1] Table 50-2 Table 50-3 Table 50-4

[0354] Table 51-1 Table 51-2 Table 51-3 Table 51-4 Table 51-5

[0355] Table 52

[0356] Table 53-1 Table 53-2 Table 53-3 Table 53-4

[0357] Table 54-1 Table 54-2 Table 54-3

[0358] Table 55-1 Table 55-2

[0359] Table 56-1 Table 56-2

[0360] Table 57

[0361] Table 58

[0362] As the results show, the compounds of the present invention of the general formula (I) in the case of post-emergence application have excellent herbicidal activity against harmful plants, such as Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Echinochloa crus-galli (ECHCG), Hordeum murinum (HORMU), Lolium rigidum (LOLRI), Matricaria inodora (Matricaria inodora), and the like, at an application rate of 0.02 kg or less of active substance per hectare. inodora (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Stellaria media (STEME), Veronica persica (VERPE), and Viola tricolor (VIOTR), as well as Oryza sativa (ORYSA), Zea mays (ZEAMX), Brassica napus (BRSNW), Glycine max (GLXMA), and Triticum aestivum at application rates of 0.02 kg per hectare or less. In the case of organisms such as Rhizobium aestivum (TRZAS), it has excellent crop compatibility.

[0363] B. Pre-emergence herbicidal activity and crop compatibility Seeds of monocotyledonous and dicotyledonous weed plants and crops are sown in plastic or organic plant pots and covered with soil.Then, the compound of the present invention formulated in the form of wettable powder (WP) or emulsifiable concentrate (EC) is sprayed on the surface of the covered soil as an aqueous suspension or emulsion, with the addition of 0.5% additive, at a water spray volume equivalent to 600 l / ha (equivalent).After treatment, the pot is placed in a greenhouse and maintained under good growing conditions for test plants.After about 3 weeks, the effect of the formulation is visually scored in percentage compared to untreated control.For example, 100% activity = plant is killed, 0% activity = same as control plant.

[0364] Tables B1 to B10 below show the efficacy of selected compounds of general formula (I) according to Tables I.1 to I.33 against various harmful plants and at application rates equivalent to 80 g / ha or less, obtained by the experimental method embodied above. Appendices "a", "b" and "c" differentiate between different dosages, otherwise the same harmful plants tested.

[0365] [Table 59]

[0366] [Table 60]

[0367] [Table 61]

[0368] [Table 62]

[0369] [Table 63]

[0370] [Table 64]

[0371] Table 65

[0372] Table 66

[0373] Table 67

[0374] Table 68

[0375] Table 69

[0376] Table 70

[0377] Table 71

[0378] Table 72

[0379] Table 73

[0380] Table 74

[0381] [Table 75]

[0382] [Table 76]

[0383] [Table 77]

[0384] Tables B11 and B12 below show the crop suitability of selected compounds of general formula (I) according to Tables I.1 to I.33 at application rates equal to or less than 80 g / ha observed in tests following the experimental procedure described above. The observed effects on this selected crop are reported here (% values) compared to untreated controls.

[0385] [Table 78]

[0386] [Table 79]

[0387] The results show that in pre-emergence treatments, the compounds of the invention of general formula (I) effectively control weeds such as, for example, Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Pharbitis purpurea, at application rates of up to 0.08 kg of active substance per hectare. It has excellent herbicidal activity against harmful plants such as P. purpurea (PHBPU) and Veronica persica (VERPE), and also has excellent crop compatibility with organisms such as Zea mays (ZEAMX) and Glycine max (GLXMA) at an application rate of 0.02 kg per hectare.

[0388] C. Herbicidal activity and crop compatibility of two compounds of the present invention (I.7-1 and I.7-115) in post-emergence applications compared with compounds of similar structure known from the literature (WO 2002 / 098227, a-17 and EP 1 106 607, 3-14).

[0389] Tables C1 to C4 below show the efficacy of two compounds of the invention (I.7-1 and I.7-115) together with compounds of similar structure known from the literature (a-17 of WO 2002 / 098227 and 3-14 of EP 1 106 607) on different crops at application rates corresponding to 5 g / ha or less, as obtained by the experimental procedure described above.

[0390] The two compounds of the present invention (I.7-1 and I.7-115) are distinguished herein by important structural differences from compounds known from the literature for ester units with the same "chain length" of the ester functionality, either through the incorporation of a heteroatom or through the incorporation of a heteroatom with simultaneous ring formation.

[0391] [Table 80]

[0392] [Table 81]

[0393] [Table 82]

[0394] [Table 83]

[0395] As the results shown in Tables C1 to C4 show, the compounds I.7-1 and I.7-115 of the present invention show a clear improvement in herbicidal activity against harmful plants such as Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Matricaria inodora (MATIN) and Setaria viridis (SETVI) at application rates of 5 g per hectare or less, compared to the literature compounds a-17 (WO 2002 / 098227) or 3-14 (EP 1 106 607).

[0396] Table C5 below shows the efficacy of two compounds of the invention (I.7-1 and I.7-115) together with compounds of similar structure known from the literature (WO 2002 / 098227 a-17 and EP 1 106 607 3-14) on the crop Oryza sativa (ORYSA) at an application rate equivalent to 1.25 g / ha obtained by the experimental procedure described above.

[0397] [Table 84]

[0398] As the results shown in Table C5 show, the compounds I.7-1 and I.7-115 of the present invention show a clear improvement in suitability for the crop Oryza sativa (ORYSA) at an application rate of 1.25 g per hectare compared to the literature compounds a-17 (WO 2002 / 098227) or 3-14 (EP 1 106 607).

Claims

1. General formula (I): 【Chemistry 1】 and / or salts thereof, R １ is hydrogen, R ２ is fluorine, R ３ is fluorine, R ４ are chlorine, bromine, cyano, NO ２ and R ５ are hydrogen, fluorine, chlorine, and bromine, R ６ is hydrogen, fluorine, chlorine, bromine, cyano, R ７ is hydrogen, G is methylene, (methyl)methylene; X is O (oxygen) or S (sulfur), Y is O (oxygen), and Q is one of the moieties Q-1 to Q-406 defined below, and the arrows in the structural formulae in the table below represent the bond of the respective Q group to the carbonyl group in general formula (I), 【Chemistry 2-1】 【Chemistry 2-2】 [Chemistry 2-3] [Chemistry 2-4] 【Chemistry 2-5】 【Chemistry 2-6】 【Chemistry 2-7】 【Chemistry 2-8】 【Chemistry 2-9】 【Chemistry 2-10】 【Chemistry 2-11】 【Chemistry 2-12】 【Chemistry 2-13】 characterized in that Compounds and / or salts thereof.

2. R １ is hydrogen, R ２ is fluorine, R ３ is fluorine, R ４ are chlorine, bromine, cyano, NO ２ and R ５ are hydrogen and fluorine, R ６ is hydrogen, fluorine, bromine, or cyano; R ７ is hydrogen, G is methylene, (methyl)methylene; X is O (oxygen) or S (sulfur), Y is O (oxygen), and Q is one of the moieties Q-1 to Q-35, Q-41 to Q-45, Q-58, Q-71 to Q-80, Q-89, Q-94, Q-95, Q-115, Q-120 to Q-123, Q-152 to Q-155, Q-166 to Q-170, Q-176 to Q-190, Q-261 to Q-348, Q-352 to Q-372, Q-377, Q-391 to Q-399 specifically mentioned in claim 1.

2. The compound of formula (I) and / or its salt according to claim 1 .

3. R １ is hydrogen, R ２ is fluorine, R ３ is fluorine, R ４ are chlorine, bromine, cyano, NO ２ and R ５ are hydrogen and fluorine, R ６ is hydrogen, fluorine, bromine, or cyano; R ７ is hydrogen, G is methylene, (methyl)methylene; X is O (oxygen) or S (sulfur), Y is O (oxygen), and Q is any of the moieties Q-1, Q-2, Q-3, Q-4, Q-7, Q-8, Q-9, Q-17, Q-18, Q-23, Q-24, Q-26, Q-27, Q-41, Q-42, Q-43, Q-58, Q-71, Q-72, Q-89, Q-94, Q-115, Q-121, Q-176, Q-177, Q-179, Q-183, Q-272, Q-274, Q-275, Q-276, Q-277, Q-278, Q-279, Q-300, Q-301, Q-302, Q-303, Q-304, Q-305, Q-306, Q-307, Q-308, Q-309, Q-410, Q-411, Q-412, Q-413, Q-414, Q-415, Q-416, Q-417, Q-418, Q-419, Q-420, Q-419, Q-4210, Q-4111, Q-4122, Q-413, Q-414, Q-415, Q-416, Q-417, Q-418, Q-419, Q-422, Q-419, Q-423, Q-424, Q-425, Q-426, Q-427, Q-428, Q-429, Q-520, Q-5210, Q-5221, Q-523, Q-524, Q-525, Q-526, Q-527, Q-528, Q-529, Q-530, Q-531, Q-53 6, Q-277, Q-278, Q-281, Q-282, Q-283, Q-284, Q-286, Q-288, Q-291, Q-296, Q-301, Q-302, Q-303, Q-308, Q-309, Q-321, Q-327, Q-328, Q-329, Q-331, Q-335, Q-339, Q-356, Q-365, Q-366, Q-367, Q-371, Q-394 2. The compound of formula (I) and / or its salt according to claim 1 .

4. Use of one or more compounds of general formula (I) and / or salts thereof according to any one of claims 1 to 3 as herbicides and / or plant growth regulators.

5. Use of one or more compounds of general formula (I) and / or salts thereof according to any one of claims 1 to 3 as herbicides and / or plant growth regulators in crops of useful plants and / or ornamental plants.

6. 1. A herbicidal and / or plant growth regulating composition comprising: The composition comprises one or more compounds of general formula (I) according to any one of claims 1 to 3 and / or salts thereof, and Group (i) and / or group (ii) comprising the following substances: (i) one or more further pesticidal active substances; (ii) one or more formulation adjuvants customary in crop protection, characterized in that it contains one or more further substances selected from Herbicidal and / or plant growth regulating compositions.

7. The herbicide and / or plant growth regulator composition of claim 6, wherein the one or more further pesticidal active substances are selected from the group consisting of insecticides, acaricides, nematicides, further herbicides, fungicides, safeners, fertilizers and / or further growth regulators.

8. 1. A method for controlling harmful plants or regulating plant growth, said method comprising: an effective amount of one or more compounds of general formula (I) and / or salts thereof according to any one of claims 1 to 3, or - administering an effective amount of the composition according to claim 6 or 7, A method characterized by applying the plant, the plant seed, the soil in or on which the plant grows or the cultivated area.

Images