Substituted n-phenyluracils and salts thereof and their use as herbicidally active substances

Abstract

The present application relates to substituted N-phenyluracils of the general formula (I) or salts thereof, wherein the radicals in general formula (I) have the meanings given in the description, and to their use as herbicides, in particular for controlling trees and / or broad-leaved weeds in crops of useful plants and / or as plant growth regulators affecting the growth of crops of useful plants.

Description

[0001] This invention relates to the technical field of plant protectants, and more particularly to herbicides for the selective control of broadleaf weeds (Unkrautem) and tree weeds (Ungrasem) in useful plant crops (agricultural crops).

[0002] Specifically, the present invention relates to substituted N-phenyluracil and its salts, methods for their preparation, and their use as herbicides, particularly for the control of broadleaf weeds and / or weeds in useful plant crops and / or as plant growth regulators affecting the growth of useful plant crops.

[0003] Plant protectants known to date for selectively controlling harmful plants in beneficial crops, or active ingredients for controlling unwanted plant growth, sometimes have drawbacks in their application, whether they (a) lack or have insufficient herbicidal activity against specific harmful plants, (b) have an insufficiently broad range (species) of harmful plants that can be controlled by the active ingredient, (c) have low selectivity for beneficial crops, and / or (d) possess toxicologically unfavorable properties. Furthermore, some active ingredients that can be used as plant growth regulators for certain beneficial plants result in undesirable reductions in harvest yield for other beneficial plants, or are only compatible with crop plants (if any) within a narrow range of application rates. Some known active ingredients cannot be produced economically on an industrial scale due to the difficulty in obtaining precursors and reagents, or due to insufficient chemical stability. In the case of other active ingredients, activity is overly dependent on environmental conditions, such as weather and soil conditions.

[0004] The herbicidal effects of these known compounds, especially at low application rates, and / or their compatibility with crop plants still need improvement.

[0005] Various literature sources indicate that specifically substituted N-bonded aryluracils can be used as active herbicidal ingredients (see EP1106607, EP408382, EP473551, EP648749, US4943309, US5084084, US5127935, US6537948, JP2001 / 348376, JP2001 / 354661, JP2002 / 003480, JP2002 / 363010, JP2002 / 363170, WO91 / 00278, WO95 / 29168, WO95 / 30661, WO96 / 35679, WO97 / 01541, WO98 / 25909, WO95 / 2 ... WO2001 / 034575, WO2001 / 39597, WO2001 / 85907, WO2002 / 098227, WO2002 / 098228, WO2003 / 028462, WO2003 / 028463, WO2003 / 0284647, WO2016 / 095768). However, there are many discrepancies in the known activity of aryluracils, especially for monocotyledonous weeds. A series of combinations of herbicidal active ingredients based on N-bonded aryluracil are also known (see DE4437197, EP714602, WO96 / 07323, WO96 / 08151, JP11189506, JP2003 / 104808, JP2003 / 104809, JP2003 / 104810, JP2003 / 160415 and JP2003 / 160416). However, the properties of these combinations of active ingredients are not entirely satisfactory.

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

[0007] It has now been surprisingly discovered that selected N-phenyluracil or its salts with substituted alkyl ester side chains are well-suited for use as herbicides and can be particularly advantageously used as active ingredients to control monocot and dicot weeds in useful plant crops.

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

[0009]

[0010] in

[0011] R 1 It can be hydrogen, halogen, cyano, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-alkoxy, or (C1-C8)-haloalkoxy.

[0012] R 2 It can be hydrogen, fluorine, chlorine, bromine, trifluoromethyl, or (C1-C8)-alkoxy.

[0013] R 3 It is hydrogen, halogen, or (C1-C8)-alkoxy.

[0014] R 4 Halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C8)-haloalkyl, (C2-C8)-alkynyl

[0015] R 5 R 6 and R 7 Independently hydrogen, halogen, cyano, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy

[0016] G is unbranched or branched (C1-C8)-alkylene.

[0017] Q is a group in the following formula

[0018]

[0019] R 8 It 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

[0020] R 9 It is hydrogen or (C1-C8)-alkyl.

[0021] R 10 It is cyano, NO2, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclic, heterocyclic-(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, heterocyclic carbonyloxy-(C1-C8)-alkyl, OR 13 NR 11 R 12 SR 14 S(O)R 14 SO2R 14 R 14 S-(C1-C8)-alkyl, R 14 (O)S-(C1-C8)-alkyl, R 14 O2S-(C1-C8)-alkyl, tri[(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, tri[(C1-C8)-alkyl]silyl, dihydroxyboryl-(C1-C8)-alkyl, bis[(C1-C8)-alkoxy]boryl-(C1-C8)-alkyl, tetramethyl-1,3,2-dioxacyclopentaborane-2-yl, tetramethyl-1,3,2-dioxacyclopentaborane-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

[0022] R 8 and R 10 Together with the carbon atoms they are bonded to, they form fully or partially saturated, and optionally further substituted, 3- to 10-membered monocyclic or bicyclic heterocyclic groups.

[0023] R 11 and R 12 They may be the same or different and each independently is hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C 10(C2-C8)-haloalkyl, (C3-C8)-haloalkenyl, (C3-C8)-haloynyl, (C3-C8)-haloalkynyl 10 )-cycloalkyl, (C3-C 10 )-Halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10 (C1-C8)-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 Heterocyclic, (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, heterocyclic-(C1-C8)-alkyl, or

[0024] R 11 and R 12 Together with the nitrogen atoms they are bonded to, they form fully or partially saturated, and optionally interrupted and further substituted 3- to 10-membered monocyclic or bicyclic rings.

[0025] R 13 It is hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-ynyl, (C1-C8)-cyanoalkyl, (C1-C 10 (C2-C8)-haloalkyl, (C3-C8)-haloalkenyl, (C3-C8)-haloynyl, (C3-C8)-haloalkynyl 10 )-cycloalkyl, (C3-C 10 )-Halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10(C1-C8)-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)-alkyl C8)-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 14 O2S-(C1-C8)-alkyl, hydroxycarbonyl-(C1-C8)-alkyl, heterocyclic, heterocyclic-(C1-C8)-alkyl, tri[(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, heterocyclic carbonyloxy-(C1-C8)-alkyl, aryloxy-(C1-C8)-alkyl, heteroaryloxy-(C1-C8)-alkyl, (C1-C8)-alkoxycarbonyl,

[0026] R 14 It is hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-ynyl, (C1-C8)-cyanoalkyl, (C1-C 10(C2-C8)-haloalkyl, (C3-C8)-haloalkenyl, (C3-C8)-haloynyl, (C3-C8)-haloalkynyl 10 )-cycloalkyl, (C3-C 10 )-Halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10 (C1-C8)-halocycloalkenyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, aryl, aryl-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocycloyl-(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-azacyclobutyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl,

[0027] and

[0028] X and Y can each be independently O (oxygen) or S (sulfur).

[0029] The present invention particularly preferably provides compounds of general formula (I), wherein

[0030] R 1 It can be hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, or (C1-C6)-haloalkoxy.

[0031] R 2 It can be hydrogen, fluorine, chlorine, bromine, trifluoromethyl, or (C1-C6)-alkoxy.

[0032] R 3 It is hydrogen, halogen, or (C1-C6)-alkoxy.

[0033] R 4 Halogen, cyano, NO2, C(O)NH2, C(S)NH2, (C1-C6)-haloalkyl, (C2-C6)-alkynyl

[0034] R 5 R 6 and R 7Each is independently hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy.

[0035] G is unbranched or branched (C1-C6)-alkylene.

[0036] Q is a group in the following formula

[0037]

[0038] R 8 It 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

[0039] R 9 It is hydrogen or (C1-C4)-alkyl.

[0040] R 10 It is cyano, NO2, heteroaryl, heteroaryl-(C1-C6)-alkyl, heterocyclic, heterocyclic-(C1-C6)-alkyl, R 11 R 12 N-(C1-C6)-alkyl, R 13 O-(C1-C6)-alkyl, cyano-(C1-C6)-alkyl, (C1-C6)-alkylcarbonyloxy-(C1-C6)-alkyl, (C3-C6)-cycloalkylcarbonyloxy-(C1-C6)-alkyl, arylcarbonyloxy-(C1-C6)-alkyl, heteroarylcarbonyloxy-(C1-C6)-alkyl, heterocyclic carbonyloxy-(C1-C6)-alkyl, OR 13 NR 11 R 12 SR 14 S(O)R 14 SO2R 14 R 14 S-(C1-C6)-alkyl, R 14 (O)S-(C1-C6)-alkyl, R 14O2S-(C1-C6)-alkyl, tri[(C1-C6)-alkyl]silyl-(C1-C6)-alkyl, bis[(C1-C6)-alkyl](aryl)silyl(C1-C6)-alkyl, [(C1-C6)-alkyl]bis(aryl)silyl-(C1-C6)-alkyl, tri[(C1-C6)-alkyl]silyl, dihydroxyboryl-(C1-C6)-alkyl, bis[(C1-C6)-alkoxy]boryl-(C1-C6)-alkyl, tetramethyl-1,3,2-dioxacyclopentaborane-2-yl, tetramethyl-1,3,2-dioxacyclopentaborane-2-yl-(C1-C6)-alkyl, nitro-(C1-C6)-alkyl, C(O)R 13 bis(C1-C6)-alkoxymethyl, bis(C1-C6)-alkoxymethyl-(C1-C6)-alkyl

[0041] R 8 and R 10 Together with the carbon atoms they are bonded to, they form fully or partially saturated, and optionally further substituted, 3- to 10-membered monocyclic or bicyclic heterocyclic groups.

[0042] R 11 and R 12 The same or different and independently of hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-ynyl, (C1-C6)-cyanoalkyl, (C1-C 10 (C2-C6)-haloalkyl, (C3-C6)-haloalkenyl, (C3-C6)-haloynyl, (C3-C6)-haloalkynyl 10 )-cycloalkyl, (C3-C 10 )-Halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10 (C1-C6)-halocycloalkenyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-haloalkoxy-(C1-C6)-alkyl, (C1-C6)-alkylthio-(C1-C6)-alkyl, (C1-C6)-haloalkylthio-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-haloalkyl, aryl, aryl-(C1-C6)-alkyl, heteroaryl, heteroaryl-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C4-C 10 )-cycloalkenyl-(C1-C6)-alkyl, COR 13 SO2R 14Heterocyclic, (C1-C6)-alkoxycarbonyl, bis[(C1-C6)-alkyl]aminocarbonyl-(C1-C6)-alkyl, (C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyl, aryl-(C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyl, aryl-(C1-C6)-alkoxycarbonyl, heteroaryl-(C1-C6)-alkoxycarbonyl, (C2-C6)-alkenyloxycarbonyl, (C2-C6)-alkynyloxycarbonyl, heterocyclic-(C1-C6)-alkyl, or

[0043] R 11 and R 12 Together with the nitrogen atoms they are bonded to, they form fully or partially saturated, and optionally interrupted and further substituted 3- to 10-membered monocyclic or bicyclic rings.

[0044] R 13 It is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-ynyl, (C1-C6)-cyanoalkyl, (C1-C 10 (C2-C6)-haloalkyl, (C3-C6)-haloalkenyl, (C3-C6)-haloynyl, (C3-C6)-haloalkynyl 10 )-cycloalkyl, (C3-C 10 )-Halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10 (C1-C6)-halocycloalkenyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-haloalkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-haloalkyl, (C1-C6)-alkoxy-(C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkoxy-(C1-C6)-alkoxy-(C1-C6)-alkyl C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkoxy-(C1-C6)-alkoxy-(C1-C6)-alkoxy-(C1-C6)-alkyl, aryl, aryl-(C1-C6)-alkyl, aryl-(C1-C6)-alkoxy-(C1-C6)-alkyl, heteroaryl, heteroaryl-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C4-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C4-C6)-alkyl, (C1 ... 10)-cycloalkenyl-(C1-C6)-alkyl, bis[(C1-C6)-alkyl]aminocarbonyl-(C1-C6)-alkyl, (C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyl, aryl-(C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyl, bis[(C1-C6)-alkyl]amino-(C2-C4)-alkyl, (C1-C6)-alkylamino-(C2-C4)-alkyl, aryl-(C1-C6)-alkylamino-(C2-C4)-alkyl, R 14 S-(C1-C6)-alkyl, R 14 (O)S-(C1-C6)-alkyl, R 14 O2S-(C1-C6)-alkyl, hydroxycarbonyl-(C1-C6)-alkyl, heterocyclic, heterocyclic-(C1-C6)-alkyl, tri[(C1-C6)-alkyl]silyl-(C1-C6)-alkyl, bis[(C1-C6)-alkyl](aryl)silyl(C1-C6)-alkyl, [(C1-C6)-alkyl]bis(aryl)silyl-(C1-C6)-alkyl, (C1-C6) )-alkylcarbonyloxy-(C1-C6)-alkyl, (C3-C6)-cycloalkylcarbonyloxy-(C1-C6)-alkyl, arylcarbonyloxy-(C1-C6)-alkyl, heteroarylcarbonyloxy-(C1-C6)-alkyl, heterocyclic carbonyloxy-(C1-C6)-alkyl, aryloxy-(C1-C6)-alkyl, heteroaryloxy-(C1-C6)-alkyl, (C1-C6)-alkoxycarbonyl,

[0045] R 14 It is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-ynyl, (C1-C6)-cyanoalkyl, (C1-C 10 (C2-C6)-haloalkyl, (C3-C6)-haloalkenyl, (C3-C6)-haloynyl, (C3-C6)-haloalkynyl 10 )-cycloalkyl, (C3-C 10 )-Halocycloalkyl, (C4-C 10 )-cycloalkenyl, (C4-C 10 (C1-C6)-halocycloalkenyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-haloalkyl, aryl, aryl-(C1-C6)-alkyl, heteroaryl, heteroaryl-(C1-C6)-alkyl, heterocycloyl-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C4-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C4-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C4-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C4-C6)-alkyl, (C3-C6)-alkyl, (C3-C6)-cycloalkyl-(C1 ... 10)-cycloalkenyl-(C1-C6)-alkyl, bis[(C1-C6)-alkyl]amino, (C1-C6)-alkylamino, aryl-(C1-C6)-amino, aryl-(C1-C2)-alkylamino, aryl-[(C1-C6)-alkyl]amino; (C3-C6)-cycloalkylamino, (C3-C6)-cycloalkyl-[(C1-C6)-alkyl]amino; N-azacyclobutyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl,

[0046] and

[0047] X and Y can each be independently O (oxygen) or S (sulfur).

[0048] The present invention particularly preferably provides compounds of general formula (I), wherein

[0049] R 1 The following are compounds: hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, butyl-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 -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

[0050] R 2 It can be hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, prop-1-yloxy, or but-1-yloxy.

[0051] R 3 It can be hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, or 1,1-dimethyleth-1-yloxy.

[0052] R 4The following are compounds: fluorine, chlorine, bromine, cyano, NO2, C(O)NH2, C(S)NH2, trifluoromethyl, difluoromethyl, pentafluoroethyl, ethynyl, propyn-1-yl, 1-butyn-1-yl, pentyyn-1-yl, hexyn-1-yl.

[0053] R 5 R 6 and R 7 Each of these elements independently represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, butyl-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

[0054] G represents methylene, (methyl)methylene, (ethyl)methylene, (propyl-1-yl)methylene, (propyl-2-yl)methylene, (butyl-1-yl)methylene, (butyl-2-yl)methylene, (pentyl-1-yl)methylene, (pentyl-2-yl)methylene, (pentyl-3-yl)methylene, (dimethyl)methylene, (diethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ylene, (2-methyl)ethyl-1-ylene, n-butylene, 1-methylpropylene-1-ylene, 2-methylpropylene-1-ylene, 3-methyl 1,1-dimethylethylene-1-yl, 2,2-dimethylethylene-1-yl, 1-ethylethylene-1-yl, 2-ethylethylene-1-yl, 1-(propyl-1-yl)ethylene-1-yl, 2-(propyl-1-yl)ethylene-1-yl, 1-(propyl-2-yl)ethylene-1-yl, 2-(propyl-2-yl)ethylene-1-yl, 1,1,2-trimethylethylene-1-yl, 1,2,2-trimethylethylene-1-yl, 1,1,2,2-tetramethylethylene-1-yl, n-methylethylene pentyl, 1-methylbutyl-1-yl, 2-methylbutyl-1-yl, 3-methylbutyl-1-yl, 4-methylbutyl-1-yl, 1,1-dimethylpropylene-1-yl, 2,2-dimethylpropylene-1-yl, 3,3-dimethylpropylene-1-yl, 1,2-dimethylpropylene-1-yl, 1,3-dimethylpropylene-1-yl, 1-ethylpropylene-1-yl, n-hexylene, 1-methylpentyl-1-ylene, 2-methylpentyl-1-ylene, 3-methylpentyl-1-ylene, 4-methylpentyl- 1-Acetyl, 1,1-Dimethylbutylene-1-yl, 1,2-Dimethylbutylene-1-yl, 1,3-Dimethylbutylene-1-yl, 2,2-Dimethylbutylene-1-yl, 2,3-Dimethylbutylene-1-yl, 3,3-Dimethylbutylene-1-yl, 1-Ethylbutylene-1-yl, 2-Ethylbutylene-1-yl, 1,1,2-Trimethylpropylene-1-yl, 1,2,2-Trimethylpropylene-1-yl, 1-Ethyl-1-methylpropylene-1-yl, 1-Ethyl-2-methylpropylene-1-yl

[0055] X and Y can each independently be O (oxygen) or S (sulfur).

[0056] and

[0057] Q is one of the following parts Q-1 to Q-406, where the arrows in the structural formulas below represent the bonds between each Q group and the carbonyl group in general formula (I):

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069] The present invention particularly preferably provides compounds of general formula (I), wherein

[0070] R 1 The following are compounds: hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, and trifluoromethoxy.

[0071] R 2 It is fluorine.

[0072] R 3 It is composed of hydrogen, fluorine, chlorine, bromine, and methoxy groups.

[0073] R 4 It can be fluorine, chlorine, bromine, cyano, NO2, C(O)NH2, C(S)NH2, trifluoromethyl, ethynyl, or propyn-1-yl.

[0074] R 5 R 6 R 7 Each of these can be independently classified as hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, or trifluoromethoxy.

[0075] G represents methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethylene-1-yl, (2-methyl)ethylene-1-yl, n-butylene, 1-methylpropylene-1-yl, 2-methylpropylene-1-yl, 3-methylpropylene-1-yl, 1,1-dimethylethylene-1-yl, 2,2-dimethylethylene-1-yl, 1-ethylethylene-1-yl, 2-ethylethylene-1-yl, 1-(propyl-1-yl)ethylene-1-yl, 2-(propyl-1-yl) Ethylene-1-yl, 1-(propyl-2-yl)ethylene-1-yl, 2-(propyl-2-yl)ethylene-1-yl, n-pentylene, 1-methylbutylene-1-yl, 2-methylbutylene-1-yl, 3-methylbutylene-1-yl, 4-methylbutylene-1-yl, 1,1-dimethylpropylene-1-yl, 2,2-dimethylpropylene-1-yl, 3,3-dimethylpropylene-1-yl, 1,2-dimethylpropylene-1-yl, 1,3-dimethylpropylene-1-yl, 1-ethylpropylene-1-yl, n-hexylene,

[0076] X and Y can each independently be O (oxygen) or S (sulfur).

[0077] and

[0078] Q refers to one of the specific components Q-1 to Q-406 mentioned above.

[0079] The present invention particularly preferably provides compounds of general formula (I), wherein

[0080] R 1 The radicals are hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, and trifluoromethoxy.

[0081] R 2 It is fluorine.

[0082] R 3 It is fluorine.

[0083] R 4 The radicals are chlorine, bromine, cyano, NO2, C(O)NH2, and C(S)NH2.

[0084] R 5 R 6 and R 7 Each of these can be independently classified as hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, or trifluoromethoxy.

[0085] G represents methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethylene-1-yl, (2-methyl)ethylene-1-yl, n-butylene, 1-methylpropylene-1-yl, 2-methylpropylene-1-yl, 3-methylpropylene-1-yl, n-pentylene, and n-hexylene.

[0086] X and Y can each independently be O (oxygen) or S (sulfur).

[0087] and

[0088] Q refers to one of the parts Q-1 to Q-406 mentioned above.

[0089] The present invention particularly preferably provides compounds of general formula (I), wherein

[0090] R 1 It consists of hydrogen, fluorine, chlorine, and bromine.

[0091] R 2 It is fluorine.

[0092] R 3 It is fluorine.

[0093] R 4 It contains chlorine, bromine, cyano, and NO2.

[0094] R 5 It consists of hydrogen, fluorine, chlorine, and bromine.

[0095] R 6 It has hydrogen, fluorine, chlorine, bromine, and cyano groups.

[0096] R 7 It consists of hydrogen, fluorine, chlorine, and bromine.

[0097] G represents methylene, (methyl)methylene, or (ethyl)methylene.

[0098] X and Y can each independently be O (oxygen) or S (sulfur).

[0099] and

[0100] Q refers to one of the parts Q-1 to Q-406 mentioned above.

[0101] The present invention particularly and preferably provides compounds of general formula (I), wherein

[0102] R 1 It is hydrogen.

[0103] R 2 It is fluorine.

[0104] R 3 It is fluorine.

[0105] R4 It consists of chlorine, bromine, cyano, and NO2.

[0106] R 5 It consists of hydrogen, fluorine, chlorine, and bromine.

[0107] R 6 It has hydrogen, fluorine, chlorine, bromine, and cyano groups.

[0108] R 7 It is hydrogen.

[0109] G stands for methylene or (methyl)methylene.

[0110] X is O (oxygen) or S (sulfur).

[0111] Y stands for O (oxygen).

[0112] and

[0113] Q refers to one of the parts Q-1 to Q-406 mentioned above.

[0114] The present invention particularly preferably provides compounds of general formula (I), wherein

[0115] R 1 It is hydrogen.

[0116] R 2 It is fluorine.

[0117] R 3 It is fluorine.

[0118] R 4 It consists of chlorine, bromine, cyano, and NO2.

[0119] R 5 It is hydrogen and fluorine.

[0120] R 6 It has hydrogen, fluorine, bromine, and cyano groups.

[0121] R 7 It is hydrogen.

[0122] G stands for methylene or (methyl)methylene.

[0123] X is O (oxygen) or S (sulfur).

[0124] Y stands for O (oxygen).

[0125] and

[0126] Q is one of the parts specifically mentioned above: 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, and Q-391 to Q-399.

[0127] The present invention particularly preferably provides compounds of general formula (I), wherein

[0128] R 1 It is hydrogen.

[0129] R 2 It is fluorine.

[0130] R 3 It is fluorine.

[0131] R 4 It consists of chlorine, bromine, cyano, and NO2.

[0132] R 5 It is hydrogen and fluorine.

[0133] R 6 It has hydrogen, fluorine, bromine, and cyano groups.

[0134] R 7 It is hydrogen.

[0135] G stands for methylene or (methyl)methylene.

[0136] X is O (oxygen) or S (sulfur).

[0137] Y stands for O (oxygen).

[0138] and

[0139] Q is the 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- mentioned specifically above 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-3 09. One of the parts Q-321, Q-327, Q-328, Q-329, Q-331, Q-335, Q-339, Q-356, Q-365, Q-366, Q-367, Q-371 and Q-394.

[0140] The above general or preferred group definitions apply to the final product of general formula (I) and, accordingly, to the preparation of the desired starting materials or intermediates. These group definitions can be combined with each other, i.e., they can also be combined arbitrarily within the specified preferred ranges.

[0141] Primarily for reasons of higher herbicidal activity, better selectivity and / or better preparability, there is particular interest in compounds of general formula (I) according to the invention or salts thereof or their use according to the invention, wherein each group has one of the preferred meanings already specified or specified below, or particularly wherein one or more preferred meanings already specified or specified below appear in combination.

[0142] If a compound can form a tautomer through hydrogen transfer that is not formally covered by general formula (I), then such tautomers are still included in the definition of compounds according to general formula (I) of the invention, unless a specific tautomer is taken into consideration. For example, many carbonyl compounds can exist in both ketone and enol forms, both of which are included in the definition of compounds according to general formula (I).

[0143] Depending on the nature of the substituents and how they are connected, compounds of general formula (I) can exist as stereoisomers. Possible stereoisomers defined by specific three-dimensional forms, such as enantiomers, diastereomers, Z- and E-isomers, are all included in general formula (I). Diastereomers (Z- and E-isomers) may occur if, for example, one or more alkenyl groups are present. Enantiomers and diastereomers may occur if, for example, one or more asymmetric carbon atoms are present. Stereoisomers can be obtained from preparative mixtures by conventional separation methods. Chromatographic separation can be performed on an analytical scale to determine excess enantiomers or diastereomers, or on a preparative scale to produce test samples for biological assays. Stereoisomers can also be selectively prepared by stereoselective reactions, using optically active starting materials and / or auxiliaries. The present invention therefore also relates to all stereoisomers included in general formula (I) but whose specific stereoforms are not shown, and mixtures thereof.

[0144] If the compound is obtained as a solid, it can also be purified by recrystallization or digestion. If a compound (I) cannot be generated satisfactorily via the following route, it can be prepared by derivatization of other compounds (I).

[0145] Suitable methods for the separation, purification, and stereoisomerization of compounds of general formula (I) are generally known to those skilled in the art from similar cases, for example by physical methods such as crystallization, chromatography, particularly column chromatography and HPLC (high-performance liquid chromatography), distillation, optionally carried out at low pressure, extraction, and other methods. Any mixtures remaining can generally be separated by chromatographic separation, for example by separation in a chiral solid phase. Suitable methods for preparation in large quantities or on an industrial scale include, for example, crystallization, such as the crystallization of diastereomer salts, which can be obtained from a mixture of diastereomers by means of an optically active acid and, if appropriate—in the presence of an acidic group—an optically active base.

[0146] Regarding the compounds according to the invention, the terms used above and below will be explained. Those skilled in the art will be familiar with these terms, and these terms have, in particular, the definitions explained below:

[0147] Unless otherwise defined, the name of a chemical group should generally be understood as being attached to the backbone or remainder of the molecule by the last structural element of the chemical group involved, i.e., by an oxygen atom in (C2-C8)-alkenoxy, and by a carbon atom of an alkyl group in heterocyclic-(C1-C8)-alkyl or (C1-C6)-alkoxy-(C1-C6)-alkoxy-(C1-C6)-alkyl, respectively.

[0148] According to the present invention, "alkylthio"—alone or as part of a chemical group—refers to a straight-chain or branched S-alkyl group, preferably having 1 to 8 or 1 to 6 carbon atoms, for example (C1-C6). 10 (C1-C6)- or (C1-C4)-alkylthio groups, such as (but not limited to) (C1-C6)-alkylthio groups, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1,1-dimethylbutyrothio, 1,2-dimethylbutyrothio, 1,3-dimethylbutyrothio, 2,2-dimethylbutyrothio, 2,3-dimethylbutyrothio, 3,3-dimethylbutyrothio, 1-ethylbutyrothio, 2-ethylbutyrothio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio.

[0149] "Alkoxy" refers to an alkyl group linked by an oxygen atom, such as (but not limited to) (C1-C6)-alkoxy groups, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, etc. 1-Methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy. Alkenyloxy refers to an alkenyl group linked by an oxygen atom, and alkynyloxy refers to an alkynyl group linked by an oxygen atom, for example (C2-C...). 10 (C2-C6)- or (C2-C4)-alkenyloxy groups and (C3-C4)-alkenyloxy groups 10 )-, (C3-C6)- or (C3-C4)-alkynyloxy group.

[0150] According to the present invention, "alkyl carbonyl" (alkyl-C(=O)-), unless otherwise defined, represents an alkyl group bonded to the backbone by -C(=O)-, for example (C1-C... 10(C1-C6)- or (C1-C4)-alkylcarbonyl. The number of carbon atoms in this text refers to the alkyl group within the alkylcarbonyl group.

[0151] "Alkoxycarbonyl (alkyl-OC(=O)-)", unless otherwise defined: an alkyl group bonded to the backbone via -OC(=O)-, for example (C1-C 10 (C1-C6)- or (C1-C4)-alkoxycarbonyl. The number of carbon atoms in this document refers to the alkyl group within the alkoxycarbonyl group. Similarly, “alkenyloxycarbonyl” and “alkynyloxycarbonyl”, unless otherwise defined, according to the invention, refer to the alkenyl and alkynyl groups bonded to the skeleton via -OC (=O)-, for example, (C2-C4)-, respectively. 10 )-, (C2-C6)- or (C2-C4)-alkenyloxycarbonyl and (C3-C 10 (C3-C6)- or (C3-C4)-alkynyloxycarbonyl. The number of carbon atoms in this text refers to the alkenyl or alkynyl group in the alkenyloxycarbonyl or alkynyloxycarbonyl group, respectively.

[0152] According to the present invention, the term "alkyl carbonyloxy" (alkyl-C(=O)-O-), unless otherwise defined, represents an alkyl group, such as (C1-C2) bonded to the skeleton by the oxygen of the carbonyloxy group (-C(=O)-O-). 10 (C1-C6)- or (C1-C4)-alkylcarbonyloxy groups. The number of carbon atoms in this text refers to the alkyl group within the alkylcarbonyloxy group.

[0153] Simplified form, such as C(O)R 13 C(O)OR 13 OC(O)NR 11 R 12 or C(O)NR 11 R 12 In the brackets, the abbreviation O represents an oxygen atom that is connected to an adjacent carbon atom via a double bond.

[0154] Simplified form such as OC(S)OR 13 OC(S)SR 14 OC(S)NR 11 R 12 In the brackets, the abbreviation S represents a sulfur atom that is connected to an adjacent carbon atom via a double bond.

[0155] The term "aryl" refers to an aromatic system having preferably 6 to 14, particularly 6 to 10, ring carbon atoms, of optional substituted monocyclic, bicyclic, or polycyclic forms, such as phenyl, naphthyl, anthracene, phenanthryl, and the like, preferably phenyl.

[0156] The term "optionally substituted aryl" also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, and biphenyl, wherein the bonding site is on an aromatic system. In systematic terminology, "aryl" is also generally included in the term "optionally substituted phenyl." Preferred aryl substituents herein are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclic, heterocyclic alkyl, alkoxyalkyl, alkathioyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, dialkylaminoalkoxy, tri[alkyl]silyl, di[alkyl]arylsilyl, di[ Alkyl]alkylsilyl, tri[alkyl]silylynyl, arylynyl, heteroarylynyl, alkylynyl, cycloalkylynyl, haloalkylynyl, heterocyclic -N-alkoxy, nitro, cyano, amino, alkylamino, bis-alkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, dialkylaminocarbonyl, heteroarylalkoxy, arylalkoxy.

[0157] The heterocyclic group (heterocyclic group) comprises at least one heterocycle (= a carbon ring in which at least one carbon atom is replaced by a heteroatom, preferably selected from N, O, S, P), which is saturated, unsaturated, partially saturated, or heteroaromatic, and may be unsubstituted or substituted, wherein the bonding site is located on a ring atom. If the heterocyclic group or heterocycle is optionally substituted, it may be fused with other carbon rings or heterocycles. In the case of optionally substituted heterocyclic groups, polycyclic systems are also included, such as 8-azabicyclo[3.2.1]octyl, 8-azabicyclo[2.2.2]octyl, or 1-azabicyclo[2.2.1]heptyl. In the case of optionally substituted heterocyclic groups, spirocyclic systems are also included, such as 1-oxa-5-azaspiro[2.3]hexyl. Unless otherwise defined, the heterocycle preferably comprises 3 to 9 ring atoms, particularly 3 to 6 ring atoms, and one or more, preferably 1 to 4, particularly 1, 2 or 3 heteroatoms in the heterocycle, preferably selected from N, O and S, but the two oxygen atoms cannot be directly adjacent, for example having one heteroatom selected from N, O and S: 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrolidin-2- or -3-yl, 2,3-dihydro-1H-pyrrolidin-1- or -2- or -3- or -4- or -5-yl; 2,5-dihydro-1 H-pyrrole-1- or -2- or -3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridine-2- or -3- or -4- or -5- or -6-yl; 1,2,3,6-tetrahydropyridine-1- or -2- or -3- or -4- or -5- or -6-yl; 1,2,3,4-tetrahydropyridine-1- or -2- or -3- or -4- or -5- or -6-yl; 1,4-dihydropyridine-1- or -2- or -3- or -4-yl; 2,3-dihydropyridine-2- or -3- -4- or -5- or -6-yl; 2,5-dihydropyridine-2- or -3- or -4- or -5- or -6-yl, 1- or 2- or 3- or 4-azacycloheptyl; 2,3,4,5-tetrahydro-1H-azacycloheptanetriene-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-1H-azacycloheptanetriene-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-1H -azacycloheptatrien-1- or -2- or -3- or -4-yl; 3,4,5,6-tetrahydro-2H-azacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-1H-azacycloheptatrien-1- or -2- or -3- or -4-yl; 2,5-dihydro-1H-azacycloheptatrien-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,7-dihydro-1H-azacycloheptatrien-1- or -2- or -3- or -4-yl;2,3-Dihydro-1H-azacycloheptatrien-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 3,4-Dihydro-2H-azacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; 3,6-Dihydro-2H-azacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7 -yl; 5,6-dihydro-2H-azacycloheptanetrien-2-or-3-or-4-or-5-or-6-or-7-yl; 4,5-dihydro-3H-azacycloheptanetrien-2-or-3-or-4-or-5-or-6-or-7-yl; 1H-azacycloheptanetrien-1-or-2-or-3-or-4-or-5-or-6-or-7-yl; 2H -Azacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; 3H-Azacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; 4H-Azacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl, 2- or 3-oxapentyl (=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-oxacyclohexyl (=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- -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-oxetane-heptyl; 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 Trien-2- or -3- or -4-yl; 2,5-Dihydroxyheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; Oxetane-heptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; 2- or 3-Tetrahydrothiophene; 2,3-Dihydrothiophene-2- or -3- or -4- or -5-yl; 2,5-Di Hydrothiophene-2- or -3-yl; tetrahydro-2H-thiaran-2- or -3- or -4-yl; 3,4-dihydro-2H-thiaran-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-thiaran-2- or -3- or -4- or -5- or -6-yl; 2H-thiaran-2- or -3- or -4- or -5- or -6-yl;4H-thiaran-2- or -3- or -4-yl. Preferred 3- and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, ethylene oxide, thiamethoxane, 1- or 2- or 3-aziridine, 2- or 3-oxetane, 2- or 3-thiamethoxane, 1,3-dioxetane-2-yl. Other examples of "heterocyclic groups" are partially or fully hydrogenated heterocyclic groups containing two heteroatoms selected from N, O, and S, such as 1- or 2- or 3- or 4-pyrazolyl groups; 4,5-dihydro-3H-pyrazol-3- or -4- or -5-yl groups; 4,5-dihydro-1H-pyrazol-1- or -3- or -4- or -5-yl groups; 2,3-dihydro-1H-pyrazol-1- or -2- or -3- or -4- or -5-yl groups; 1- or 2- or 3- or 4-imidazolyl groups; 2,3-dihydro-1H-imidazolyl-1- or -2- or -3- or -4-yl groups; 2,5-dihydro-1H-imidazolyl-1- or -2- or -4- or -5-yl groups. ; 4,5-Dihydro-1H-imidazol-1- or -2- or -4- or -5-yl; hexahydropyridazine-1- or -2- or -3- or -4-yl; 1,2,3,4-tetrahydropyridazine-1- or -2- or -3- or -4- or -5- or -6-yl; 1,2,3,6-tetrahydropyridazine-1- or -2- or -3- or -4- or -5- or -6-yl; 1,4,5,6-tetrahydropyridazine-1- or -3- or -4- or -5- or -6-yl; 3,4,5,6-tetrahydropyridazine-3- or -4- or -5-yl; 4,5-dihydropyridazine-3- or -4-yl; 3,4-dihydropyridazine-3- or -4- or -5-yl or -6-yl; 3,6-dihydropyridazine-3- or -4-yl; 1,6-dihydropyrazine-1- or -3- or -4- or -5- or -6-yl; hexahydropyrimidine-1- or -2- or -3- or -4-yl; 1,4,5,6-tetrahydropyrimidine-1- or -2- or -4- or -5- or -6-yl; 1,2,5,6-tetrahydropyrimidine-1- or -2- or -4- or -5- or -6-yl; 1,2,3,4-tetrahydropyrimidine-1- or -2- or -3- or -4- or -5- or -6-yl; 1,6-dihydropyrimidine-1- or -2- or -4- or -5- or -6-yl; 1,2-dihydropyrimidine-1- or - 2- or -4- or -5- or -6-yl; 2,5-dihydropyrimidine-2- or -4- or -5-yl; 4,5-dihydropyrimidine-4- or -5- or -6-yl; 1,4-dihydropyrimidine-1- or -2- or -4- or -5- or -6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-tetrahydropyrazine-1- or -2- or -3- or -5- or -6-yl; 1,2,3,4-tetrahydropyrazine-1- or -2- or -3- or -4- or -5- or -6-yl; 1,2-dihydropyrazine-1- or -2- or -3- or -5- or -6-yl; 1,4-dihydropyrazine-1- or -2- or -3-;2,3-Dihydropyrazine-2- or -3- or -5- or -6-yl; 2,5-Dihydropyrazine-2- or -3-yl; 1,3-Dioxane-2- or -4- or -5-yl; 1,3-m-Dioxane-2- or -4- or -5-yl; 1,3-Dioxane-2- or -4- or -5-yl; 4H-1,3-Dioxane-2- or -4- or -5- or -6-yl; 1,4-dioxane-2- or -3- or -5- or -6-yl; 2,3-dihydro-1,4-dioxen-2- or -3- or -5- or -6-yl; 1,4-dioxen-2- or -3-yl; 1,2-dithiacyclopentane-3- or -4-yl; 3H-1,2-dithiacyclopentadien-3- or -4- or -5-yl; 1,3-dithiacyclopentane-2- or -4-yl; 1,3-dithiacyclopentadien-2- or -4-yl; 1,2-dithiaran-3- or -4-yl; 3,4-dihydro-1,2-dithiain-3- or -4- or -5- or -6-yl; 3,6-dihydro-1,2-dithiain-3- or -4-yl; 1,2-dithiain-3- or -4-yl; 1,3-dithiane-2- or -4- or -5-yl; 4H-1,3-dithiain-2- or -4- or -5- or -6-yl; isoxazolidine-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-oxazolidine-2- or -3- or -4- or -5-yl; 2,3-dihydro-1,3-oxazol-2- or -3- or -4- or -5-yl; 2,5-dihydro-1,3-oxazol-2- or -4- or -5-yl; 4,5-dihydro-1,3-oxazol-2- or -4- Or -5-yl; 1,2-oxazacyclohexane-2- or -3- or -4- or -5- or -6-yl; 3,4-dihydro-2H-1,2-oxazine-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-1,2-oxazine-2- or -3- or -4- or -5- or -6-yl; 5,6-dihydro-2H-1 2-Oxazine-2- or -3- or -4- or -5- or -6-yl; 5,6-dihydro-4H-1,2-oxazine-3- or -4- or -5- or -6-yl; 2H-1,2-oxazine-2- or -3- or -4- or -5- or -6-yl; 6H-1,2-oxazine-3- or -4- or -5- or -6-yl; 4H-1,2-oxazine Azine-3- or -4- or -5- or -6-yl; 1,3-oxazacyclohexane-2- or -3- or -4- or -5- or -6-yl; 3,4-dihydro-2H-1,3-oxazine-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-1,3-oxazine-2- or -3- or -4- or -5- or -6-yl;5,6-Dihydro-2H-1,3-oxazine-2- or -4- or -5- or -6-yl; 5,6-Dihydro-4H-1,3-oxazine-2- or -4- or -5- or -6-yl; 2H-1,3-oxazine-2- or -4- or -5- or -6-yl; 6H-1,3-oxazine-2- or -4- or -5- or -6-yl; 4H-1,3-oxazine-2- or -4- or -5- or -6-yl; Morpholin-2- or -3- or -4-yl; 3,4-Dihydro-2H-1,4-oxazine-2- or -3- or -4- or -5- or -6-yl; 3,6-Dihydro-2H-1,4-oxazine-2- or -3- or -5- or -6-yl; 2H-1,4-oxazine-2 - or -3- or -5- or -6-yl; 4H-1,4-oxazine-2- or -3-yl; 1,2-oxazacycloheptane-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,5-tetrahydro-1,2-oxazacycloheptane-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-1,2-oxazacycloheptane-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-1,2-oxazacycloheptane-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5,6,7-tetrahydro-1,2-oxazacycloheptane-2- or - 3- or -4- or -5- or -6- or -7-yl; 4,5,6,7-tetrahydro-1,2-oxazacycloheptatrien-3- or -4- or -5- or -6- or -7-yl; 2,3-dihydro-1,2-oxazacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5-dihydro-1,2-oxazacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; 2,7-dihydro-1,2-oxazacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-1,2-oxazacycloheptatrien-3- or -4- or -5- or -6- or -7-yl; 4,7- Dihydro-1,2-oxazacycloheptatrien-3- or -4- or -5- or -6- or -7-yl; 6,7-dihydro-1,2-oxazacycloheptatrien-3- or -4- or -5- or -6- or -7-yl; 1,2-oxazacycloheptatrien-3- or -4- or -5- or -6- or -7-yl; 1,3-oxazacycloheptan-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,5-tetrahydro-1,3-oxazacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-1,3-oxazacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl;2,3,6,7-Tetrahydro-1,3-oxazacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5,6,7-Tetrahydro-1,3-oxazacycloheptatrien-2- or -4- or -5- or -6- or -7-yl; 4,5,6,7-Tetrahydro-1,3-oxazacycloheptatrien-2- or -4- or -5- or -6- or -7-yl; 2,3-Dihydro-1,3-oxazacycloheptatrien-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5-Dihydro-1,3-oxazacycloheptatrien-2- or -4- or -5- or -6- or -7-yl; 2,7-Dihydro-1,3-oxazacycloheptatrien-2- or - 4- or -5- or -6- or -7-yl; 4,5-dihydro-1,3-oxazacycloheptatrien-2- or -4- or -5- or -6- or -7-yl; 4,7-dihydro-1,3-oxazacycloheptatrien-2- or -4- or -5- or -6- or -7-yl; 6,7-dihydro-1,3-oxazacycloheptatrien-2- or -4- -5- or -6- or -7-yl; 1,3-oxazacycloheptatrien-2- or -4- or -5- or -6- or -7-yl; 1,4-oxazacycloheptan-2- or -3- or -5- or -6- or -7-yl; 2,3,4,5-tetrahydro-1,4-oxazacycloheptatrien-2- or -3- or -4- or -5- or -6- or - 7-yl; 2,3,4,7-tetrahydro-1,4-oxazapyridine-heptanetrien-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-1,4-oxazapyridine-heptanetrien-2- or -3- or -5- or -6- or -7-yl; 2,5,6,7-tetrahydro-1,4-oxazapyridine-heptanetrien-2- -3- or -5- or -6- or -7-yl; 4,5,6,7-tetrahydro-1,4-oxazapyridine-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3-dihydro-1,4-oxazapyridine-2- or -3- or -5- or -6- or -7-yl; 2,5-dihydro-1,4-oxazapyridine-heptane Trien-2- or -3- or -5- or -6- or -7-yl; 2,7-dihydro-1,4-oxazapyridine-2- or -3- or -5- or -6- or -7-yl; 4,5-dihydro-1,4-oxazapyridine-2- or -3- or -4- or -5- or -6- or -7-yl; 4,7-dihydro-1,4-oxazapyridine-2- or -3- or -4- or -5- or -6- or -7-yl; 6,7-dihydro-1,4-oxazapyridine-2- or -3- or -5- or -6- or -7-yl; 1,4-oxazapyridine-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-Thiazolidin-2- or -3- or -4- or -5-yl; 2,3-Dihydro-1,3-Thiazol-2- or -3- or -4- or -5-yl; 2,5-Dihydro-1,3-Thiazol-2- or -4- or -5-yl; 4,5-Dihydro-1,3-Thiazol-2- or -4- or -5-yl; 1,3-Thiazazacyclohexane-2- or -3- or -4- or -5- or -6-yl; 3,4 -dihydro-2H-1,3-thiazin-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-1,3-thiazin-2- or -3- or -4- or -5- or -6-yl; 5,6-dihydro-2H-1,3-thiazin-2- or -4- or -5- or -6-yl; 5,6-dihydro-4H-1,3-thiazin-2- or -4- or -5- or -6-yl; 2H-1,3-thiazin-2- or -4- or -5- or -6-yl; 6H-1,3-thiazin-2- or -4- or -5- or -6-yl; 4H-1,3-thiazin-2- or -4- or -5- or -6-yl. Other examples of "heterocyclic groups" are partially or fully hydrogenated heterocyclic groups containing three heteroatoms selected from N, O, and S, such as 1,4,2-dioxazolidine-2- or -3- or -5-yl; 1,4,2-dioxazol-3- or -5-yl; 1,4,2-dioxazine-2- or -3- or -5- or -6-yl; 5,6-dihydro-1,4,2-dioxazine-3- or -5- or -6-yl; 1,4,2-dioxazine-3- or -5- or -6-yl; 1,4,2-dioxazine-2- or -3- or -5- or -6- or -7-yl; 6, 7-Dihydro-5H-1,4,2-dioxazonium-heptanetriene-3- or -5- or -6- or -7-yl; 2,3-Dihydro-7H-1,4,2-dioxazonium-heptanetriene-2- or -3- or -5- or -6- or -7-yl; 2,3-Dihydro-5H-1,4,2-dioxazonium-heptanetriene-2- or -3- or -5- or -6- or -7-yl; 5H-1,4,2-dioxazonium-heptanetriene-3- or -5- or -6- or -7-yl; 7H-1,4,2-dioxazonium-heptanetriene-3- or -5- or -6- or -7-yl. Examples of other optionally substituted heterocycles are listed below:

[0158]

[0159]

[0160]

[0161] The heterocycles listed above are preferably substituted with the following: for example, hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclic, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trialkylsilylalkynyl, nitro, amino, cyano, halogen Alkyloxy, haloalkylthio, alkylthio, hydrogen thio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclic alkoxy, heterocyclic alkylthio, heterocyclic thio, heteroaryloxy, dialkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.

[0162] When the basic structure is replaced by one or more groups selected from a series of groups (= radicals) or a group of groups defined by category, this includes, in each case, being replaced by multiple identical and / or structurally different groups simultaneously.

[0163] In the case of partially or fully saturated nitrogen heterocycles, they can be attached to the remainder of the molecule either via carbon or nitrogen.

[0164] Suitable substituents for the substituted heterocyclic groups are those mentioned later, as well as oxo and thio substituents. Oxosubstituted groups on the ring carbon atoms are, for example, carbonyl groups on the heterocycle. Therefore, lactones and lactams are also preferred. Oxosubstituted groups can also appear on the ring heteroatom and can exist in different oxidation states; for example, in the case of N and S, divalent -N(O)-, -S(O)- (also abbreviated as SO), and -S(O)2- (also abbreviated as SO2) groups are thus formed in the heterocycle. In the case of –N(O)- and –S(O)- groups, each includes two enantiomers.

[0165] According to the present invention, the term "heteroaryl" represents heteroaromatic compounds, that is, fully unsaturated aromatic heterocyclic compounds, preferably having 1 to 4, more preferably 1 or 2 identical or different heteroatoms, preferably O, S or N, 5 to 7-membered rings. The heteroaryl groups in this invention are, for example, 1H-pyrrolo-1-yl; 1H-pyrrolo-2-yl; 1H-pyrrolo-3-yl; furan-2-yl; furan-3-yl; thiophen-2-yl; thiophen-3-yl; 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazole-3-yl; 1H-pyrazole-4-yl; 1H-pyrazole-5-yl; 1H-pyrazole-1-yl; 1H-pyrazole-3-yl; 1H-pyrazole-4-yl; 1H-pyrazole-5-yl; 1H-1,2,3-triazol-1-yl; 1H-1,2,3-triazol-4-yl; 1H-1,2,3-triazol-5-yl; 2 H-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, aziridine-heptadienyl, 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-oxazolyl -5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, oxadiazonitetrienyl, thiaheptaquinoneyl, 1,2,4-triazoloneyl and 1,2,4-diazabiazonitetrienyl, 2H-1,2,3,4-tetrazolitetrienyl, 1H-1,2,3,4-tetrazolitetrienyl, 1,2,3,4-oxatriazolitetrienyl, 1,2,3,4-thiatriazolitetrienyl, 1,2,3,4-oxatriazolitetrienyl, 1,2,3,4-thiatriazolitetrienyl, 1,2,3,5-oxatriazolitetrienyl, 1,2,3,5-thiatriazolitetrienyl. The heteroaryl groups of the present invention may also be substituted by one or more identical or different groups. If two adjacent carbon atoms are part of another aromatic ring, the system is a fused heteroaromatic system, such as benzofused or polyfused heteroaromatic systems.Preferred examples are quinolines (e.g., quinoline-2-yl, quinoline-3-yl, quinoline-4-yl, quinoline-5-yl, quinoline-6-yl, quinoline-7-yl, quinoline-8-yl); isoquinolines (e.g., isoquinoline-1-yl, isoquinoline-3-yl, isoquinoline-4-yl, isoquinoline-5-yl, isoquinoline-6-yl, isoquinoline-7-yl, isoquinoline-8-yl); quinoxaline; quinazolin; zoline; 1,5-naphthoidine; 1,6-naphthoidine; 1,7-naphthoidine; 1,8-naphthoidine; 2,6-naphthoidine; 2,7-naphthoidine; phthalazine; pyridopyrazine; pyridopyrimidine; pyridopyridazine; pteridine; pyrimidine. Examples of heteroaryl groups are also selected from the following 5- or 6-membered benzo-fused rings: 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl 1-Benzothiophene-5-yl, 1-Benzothiophene-6-yl, 1-Benzothiophene-7-yl, 1H-Indazole-1-yl, 1H-Indazole-3-yl, 1H-Indazole-4-yl, 1H-Indazole-5-yl, 1H-Indazole-6-yl, 1H-Indazole-7-yl, 2H-Indazole-2-yl, 2H-Indazole-3-yl, 2H-Indazole-4-yl, 2H-Indazole-5-yl, 2H-Indazole-6-yl, 2H-Indazole-7-yl, 2H-Isoindol-2-yl, 2H-Isoindol-1-yl, 2H-Isoindol-3-yl, 2H-Isoindol-2-yl Indole-4-yl, 2H-isoindole-5-yl, 2H-isoindole-6-yl; 2H-isoindole-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-benzoisoxazole-3-yl, 1,2-benzoisoxazole-4-yl, 1,2-benzoisoxazole-5-yl, 1,2-benzoisoxazole-6-yl, 1,2-benzoisoxazole-7-yl, 1,2-benzoisothiazol-3-yl, 1,2-benzoisothiazol-4-yl, 1,2-benzoisothiazol-5-yl, 1,2-benzoisothiazol-6-yl, 1,2-benzoisothiazol-7-yl.

[0166] The term "halogen" refers to, for example, fluorine, chlorine, bromine, or iodine. When the term is used with a group, "halogen" means, for example, a fluorine, chlorine, bromine, or iodine atom.

[0167] According to the present invention, "alkyl" refers to a straight-chain or branched open-chain saturated hydrocarbon group, which is optionally monosubstituted or polysubstituted, and in the latter case, is referred to as "substituted alkyl". Preferred substituents are halogen atoms, alkoxy groups, haloalkoxy groups, cyano groups, alkylthio groups, haloalkylthio groups, amino groups, or nitro groups, with methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine, or iodine groups being particularly preferred. The prefix "bis" also includes combinations of different alkyl groups, for example, methyl (ethyl) or ethyl (methyl).

[0168] "Haloalkyl", "-alkenyl", and "-ynyl" refer to alkyl, alkenyl, and ynyl groups that are partially or completely replaced by the same or different halogen atoms, respectively. Examples of monohaloalkyl groups include CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, and CH2F; while examples of perhaloalkyl groups include CCl. 3、 CClF 2、 CFCl2, CF2CClF2, CF2CClFCF3; polyhalogenated alkyl groups such as CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3; the term "perhalogenated alkyl" also includes the term "perfluoroalkyl".

[0169] "Haloalkoxy" is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2Cl; this applies accordingly to haloalkenyl and other halogen-substituted groups.

[0170] The illustrative expression “(C1-C4)-alkyl” mentioned herein is an abbreviation for a straight-chain or branched alkyl group containing 1 to 4 carbon atoms, depending on the stated carbon number range, i.e., including methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl, or tert-butyl groups. Conventional alkyl groups having a larger carbon atom range, such as “(C1-C6)-alkyl”, also accordingly include straight-chain or branched alkyl groups containing a larger number of carbon atoms, i.e., according to examples, there are also alkyl groups having 5 and 6 carbon atoms.

[0171] Unless otherwise stated, in the case of hydrocarbon groups such as alkyl, alkenyl, and alkynyl groups, and also in the case of complex groups, a skeleton with a lower carbon number is preferred, for example, having 1 to 6 carbon atoms, or in the case of unsaturated groups having 2 to 6 carbon atoms. Alkyl groups, and also in complex groups such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, tert-butyl or 2-butyl, pentyl, hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl, heptyl such as n-heptyl, 1-methylhexyl, and 1,4-dimethylpentyl; alkenyl and alkynyl groups mean possible unsaturated groups corresponding to alkyl groups, containing at least one double or triple bond. Groups having one double or triple bond are preferred.

[0172] The term "alkenyl" also specifically includes straight-chain or branched open-chain hydrocarbon groups having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, as well as propadienyl or cumulenyl groups having one or more cumulative double bonds, such as propadienyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-penttrienyl. Alkenyl can mean, for example, vinyl groups optionally substituted with other alkyl groups, such as (but not limited to) (C2-C6)-alkenyl groups, such as vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2 ... 2-Butenyl, 1-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl 4-Methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2 2-Dimethyl-3-butenyl, 2,3-Dimethyl-1-butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1-butenyl, 3,3-Dimethyl-2-butenyl, 1-Ethyl-1-butenyl, 1-Ethyl-2-butenyl, 1-Ethyl-3-butenyl, 2-Ethyl-1-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1,1,2-Trimethyl-2-propenyl, 1-Ethyl-1-methyl-2-propenyl, 1-Ethyl-2-methyl-1-propenyl and 1-Ethyl-2-methyl-2-propenyl.

[0173] The term "alkynyl" also specifically includes straight-chain or branched open-chain hydrocarbon groups having more than one triple bond or having one or more triple bonds and one or more double bonds, such as 1,3-buttrienyl or 3-pent-1-en-1-yl. (C2-C6)-alkynyl refers to, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3- Pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.

[0174] The term "cycloalkyl" refers to a saturated carbocyclic system having preferably 3-8 ring carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, optionally further substituted, preferably further substituted with: hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, dialkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, or cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl groups, this includes cyclic systems containing substituents, including substituents containing a double bond on the cycloalkyl group, such as pinene or methine. In the case of optionally substituted cycloalkyl groups, polycyclic aliphatic systems are also included, such as bicyclo[1.1.0]but-1-yl, bicyclo[1.1.0]but-2-yl, bicyclo[2.1.0]pent-1-yl, bicyclo[1.1.1]pent-1-yl, bicyclo[2.1.0]pent-2-yl, bicyclo[2.1.0]pent-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]oct-2-yl, bicyclo[3.2.1]oct-2-yl, bicyclo[3.2.2]non-2-yl, adamantane-1-yl, and adamantane-2-yl, as well as some systems such as 1,1'-bis(cyclopropyl)-1-yl and 1,1'-bis(cyclopropyl)-2-yl. The term “(C3-C7)-cycloalkyl” refers to the range of carbon atoms described, and is an abbreviation for cycloalkyl with 3 to 7 carbon atoms.

[0175] In the case of cycloalkyl groups, spirocycloaliphatic 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.

[0176] "Cycloalkenyl" refers to a non-aromatic, partially unsaturated carbocyclic system having preferably 4-8 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, including substituents containing a double bond on the cycloalkenyl group, such as alkylene groups, for example, methineyl groups, for example, methylene groups. In the case of optionally substituted cycloalkenyl groups, the interpretation of substituted cycloalkyl groups may be applied accordingly.

[0177] The term "pyrenoid" is also used for example (C1-C) 10The term "-benzenealkyl" refers to a straight-chain or branched open-chain hydrocarbon group linked by a double bond. The possible bonding sites for benzenealkyl groups are naturally located only at positions in the basic structure where two hydrogen atoms can be replaced by a double bond; the group is, for example, =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5, or =C(C2H5)-C2H5. Cyclobenzenealkyl refers to a carbocyclic group linked by a double bond.

[0178] The term "alkylene" also refers to, for example, (C1-C8)-alkylene, a straight-chain or branched open-chain hydrocarbon group that is attached to other groups at two positions.

[0179] "Alkoxyalkyl" refers to an alkoxy group bonded by an alkyl group, and "alkoxyalkoxy" refers to an alkoxyalkyl group bonded by an oxygen atom, such as (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, and methoxypropoxy.

[0180] "Arylalkyl" refers to an aryl group bonded by an alkyl group, "heteroarylalkyl" refers to a heteroaryl group bonded by an alkyl group, and "heterocyclicalkyl" refers to a heterocyclic group linked by an alkyl group.

[0181] “Cycloalkylalkyl” represents a cycloalkyl group bonded by an alkyl group, such as (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropylethyl-1-yl, 2-cyclopropylethyl-1-yl, 1-cyclopropylpropyl-1-yl, 3-cyclopropylpropyl-1-yl.

[0182] "Arylalkenyl" refers to an aryl group bonded by an alkenyl group, "heteroarylalkenyl" refers to a heteroaryl group bonded by an alkenyl group, and "heterocyclic alkenyl" refers to a heterocyclic group bonded by an alkenyl group.

[0183] "Aromaticynyl" represents an aryl group bonded by an alkynyl group, "Heteroaryynyl" refers to a heteroaryl group bonded by an alkynyl group, and "Heterocyclicynyl" refers to a heterocyclic group bonded by an alkynyl group.

[0184] According to the present invention, “haloalkylthio” – either in itself or as part of a chemical group – represents a straight-chain or branched S-haloalkyl group, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C1-C8)-, (C1-C6)- or (C1-C4)-haloalkylthio, such as (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroethyl-1-thio, 2,2,2-difluoroethyl-1-thio, 3,3,3-prop-1-thio.

[0185] "Halogenated cycloalkyl" and "halogenated cycloalkenyl" respectively refer to cycloalkyl or cycloalkenyl groups that are partially or completely substituted with the same or different halogen atoms such as F, Cl and Br, or with halogenated alkyl groups such as trifluoromethyl or difluoromethyl, for example, 1-fluorocyclopropyl-1-yl, 2-fluorocyclopropyl-1-yl, 2,2-difluorocyclopropyl-1-yl, 1-fluorocyclobutyl-1-yl, 1-trifluoromethylcyclopropyl-1-yl, 2-trifluoromethylcyclopropyl-1-yl, 1-chlorocyclopropyl-1-yl, 2-chlorocyclopropyl-1-yl, 2,2-dichlorocyclopropyl-1-yl, and 3,3-difluorocyclobutyl.

[0186] Synthesis of substituted N-phenyluracil of general formula (I).

[0187] According to the present invention, substituted N-phenyluracil of general formula (I) can be prepared by known methods. The synthetic route used and investigated herein begins with a commercially available or readily prepared heteroaromatic amine and the corresponding substituted hydroxy ester. In the following schemes, G, Q, R in general formula (I) 1 R 2 R 3 R 4 R 5 R 6 R 7The X and Y portions have the meanings defined above, unless given in an illustrative but not limiting manner. As a first key intermediate for the synthesis of compounds of general formula (Ia) according to the invention, wherein X is sulfur (S) and Y is oxygen (O), a mercaptophenyl-1H-pyrimidin-2,4-dione, optionally further substituted, was prepared. This is illustrated, by way of example but not limitation, by the synthesis of 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidin-2,4-dione (IIa) (Scheme 1). For this purpose, a suitable substituted aniline, such as, but not limited to, 2-fluoro-4-chloroaniline, is converted to the corresponding isocyanate in a suitable polar aprotic solvent (e.g., dichloromethane) with a suitable reaction reagent (e.g., triphosgene). In the next step, it is converted to the corresponding pyrimidine-2,4-dione by reacting it with a suitable aminoacrylate in a suitable polar aprotic solvent (e.g., N,N-dimethylformamide) using a suitable base (e.g., sodium hydride or potassium tert-butoxide), which is optionally further substituted, such as, but not limited to, 3-(4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (Scheme 1). The desired mercaptophenyl-1H-pyrimidin-2,4-dione, such as but not limited to 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidin-2,4-dione (IIa), can be prepared by subsequent sulfonation with a suitable reagent (e.g., chlorosulfonic acid) followed by reduction with a suitable reducing agent (e.g., zinc in ethanol and HCl, tin(II) chloride hydrate, or triphenylphosphine). (See KR1345394; EP1122244; EP408382; WO 2003 / 029226; WO2010 / 038953; US2011 / 0224083; KR2011 / 110420). In Scheme 1 below, R 2 and R 3 For example, but not limited to, fluorine, R 4 For example, but not limited to, chlorine, and X, for example, but not limited to, sulfur.

[0188]

[0189] Option 1

[0190] The synthesis of the key intermediate (IIa) described in Scheme 1 is applicable to the preparation of similar intermediates. The corresponding further substituted N-methyl-5-mercaptophenyl-1H-pyrimidin-2,4-dione intermediate (II) can be converted to the desired compound of general formula (Ia) according to the invention via various routes, where X is sulfur (S) and Y is oxygen (O) (Scheme 2). Then, in the first step, compound (II) is converted to intermediate (III) by means of a suitable optionally further substituted iodophenol, using a suitable base or a suitable transition metal catalyst (e.g., tris(dibenzylideneacetone)dipalladium(O)) with a suitable ligand (e.g., 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene) and a suitable base (e.g., diisopropyl(ethyl)amine) in a suitable polar aprotic solvent (e.g., dioxane). In Scheme 2 below, Q, R 2 R 3 R 3 and R 4 This has the meaning described above according to the present invention. Furthermore, R 1 R 5 R 6 R 7 For example, but not limited to, hydrogen; X, for example, but not limited to, sulfur; Y, for example, but not limited to, oxygen; and G, for example, but not limited to, CH2. The corresponding intermediate (III) described, for example, but not limited to, scheme 2, can be converted to the corresponding oxyalkanoate intermediate (IVa, IVb) or the desired target general formula (Ia) compound by reacting with a suitable, optionally further substituted iodoalkanoate (for example, but not limited to, iodoacetate in scheme 3) in a suitable polar aprotic solvent (e.g., n-hexane or cyclohexane) at high temperature (e.g., under microwave conditions) using a suitable base (e.g., silver carbonate (I)). The corresponding iodoalkanoate can be prepared by routes known in the literature (see Eur. J. Org. Chem., 2006, 71, 8459; WO2012037573; Organometallics, 2009, 28, 132).

[0191]

[0192] Option 2

[0193] The ethyl ester (IVa) and tert-butyl ester (IVb) intermediates can then be converted to the corresponding free acid (V) under suitable reaction conditions [in the case of (IVa), using a suitable acid such as hydrochloric acid or acetic acid, or in the case of (IVb), using trifluoroacetic acid (TFA)]. The desired substituted N-phenyluracil of general formula (Ia) can be prepared by reacting the corresponding acid intermediate (V) with a suitable compound QH in a suitable polar aprotic solvent (e.g., dichloromethane, chloroform) under the regulation of a suitable coupling agent (e.g., HOBt = 1-hydroxybenzotriazole, EDC = 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, HATU = O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethylurea hexafluorophosphate, T3P = 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphacyclohexane 2,4,6-trioxide) and a suitable base (e.g., diisopropylethylamine, triethylamine). Alternatively, the ethyl ester (IVa) can be converted into the corresponding substituted N-phenyluracil of the desired general formula (Ia) by coupling with a suitable compound QH under the control of a suitable Lewis acid (e.g., indium(III) chloride) (see WO2011 / 1307088).

[0194] The preparation of compounds of general formula (I), where X and Y represent, for example but not limited to, oxygen (O), is carried out by synthesizing a key intermediate (VI) having a fluorine substituent at the 5-position, such as 3-(2,5-difluoro-4-nitro)-1-methyl-6-trifluoromethyl-1H-pyrimidin-2,4-dione (VIa). For this purpose, a suitable substituted aniline, such as but not limited to 2,5-difluoroaniline, is converted to the corresponding isocyanate in a suitable polar aprotic solvent (e.g., dichloromethane) with a suitable reactant (e.g., triphosgene). In the next step, the corresponding isocyanate is converted to the corresponding pyrimidin-2,4-dione by reacting with a suitable aminoacrylate in a suitable polar aprotic solvent (e.g., N,N-dimethylformamide) using a suitable base (e.g., sodium hydride or potassium tert-butoxide), optionally further substituted, here for example but not limited to 3-(2,5-difluorophenyl)-6-trifluoromethyl-1H-pyrimidin-2,4-dione (Scheme 3). Nitration with a suitable nitrating agent, followed by N-methylation with a suitable methylating agent, yields the desired intermediate, for example, but not limited to, 3-(2,5-difluoro-4-nitro)-1-methyl-6-trifluoromethyl-1H-pyrimidin-2,4-dione (VIa). In Scheme 3 below, R 2 and R 3 For example, but not limited to, fluorine, and R 4 For example, but not limited to, nitro groups.

[0195]

[0196] Option 3

[0197] The intermediate (VI) obtained in the manner described above, such as compound (VIa), can then be converted into the desired substituted N-phenyluracil (Ib, R) using a suitable substituted 2-carbonylalkoxy-1-hydroxybenzene (VII), with a suitable base (e.g., potassium carbonate), in a suitable polar aprotic solvent (e.g., N,N-dimethylformamide (DMF)). 4 =Nitro). The intermediate (VII) used for this purpose can be obtained from commercially available 1-chloro-2-nitrobenzene via a multi-step synthesis, said multi-step synthesis being (i) base-regulated coupling (e.g., with sodium hydride) in a suitable polar aprotic solvent (e.g., tetrahydrofuran or dioxane) with a suitable substituted hydroxyalkyl carbonyl reagent, or alternatively by reacting 2-nitrophenol with a suitable substituted chloromethyl carbonyl reagent, (ii) reduction of the nitro group with a suitable reducing agent (e.g., hydrogen, palladium supported on carbon in a suitable polar protic solvent), and (iii) diazotization (using a suitable diazotizing agent, For example, tert-butyl nitrite (t-BuONO), boron trifluoride ether (BF3-OEt2), react with acetic anhydride in a suitable polar aprotic solvent (e.g., dichloromethane (DCM), dimethoxyethane), (iv) and (v) by removing the acetyl protecting group (e.g., base-regulated with potassium carbonate in a polar protic solvent) to release the hydroxyl group. The nitro group of compound (Ib) can then be converted to a halogen substituent (e.g., chlorine, bromine) by reduction and a subsequent Sandmeyer reaction, so that the desired substituted N-phenyluracil (Ic) can be obtained in this manner. In scheme 4 below, Q and R 2 It has the meaning of the above-mentioned invention. Furthermore, R 3 For example, but not limited to, fluorine, R 4 For example, but not limited to, chlorine or nitro, R 1 R 5 R 6 R 7 For example, but not limited to, hydrogen; X and Y, for example, but not limited to, oxygen; and G, for example, but not limited to, CH2.

[0198]

[0199] Option 4

[0200] Therefore, the intermediate (VI) obtained in the manner described above can be converted into the desired substituted N-phenyluracil (Id, R) using a suitable substituted 2-carbonylalkylthio-1-hydroxybenzene (VIII), a suitable base (e.g., potassium carbonate), and in a suitable polar aprotic solvent (e.g., N,N-dimethylformamide (DMF)). 4=nitro), where X = O (oxygen) and Y = S (sulfur). The intermediate (VIII) used for this purpose can be prepared by a multi-step synthesis similar to that of intermediate (VII) described in Scheme 4, starting from commercially available 1-chloro-2-nitrobenzene or 2-nitrobenzenethiophenol. The nitro group in compound (Id) can then be converted to a halogen substituent (e.g., chlorine, bromine) by reduction and subsequent Sandmeyer reaction, so that the desired substituted N-phenyluracil (Ie) can be obtained in this way. In Scheme 5 below, Q and R 2 This has the meaning described above according to the present invention. Furthermore, R 3 For example, but not limited to, fluorine, R 4 For example, but not limited to, chlorine or nitro, R 1 R 5 R 6 R 7 For example, but not limited to, hydrogen; X, for example, but not limited to, oxygen; Y, for example, but not limited to, sulfur; and G, for example, but not limited to, CH2.

[0201]

[0202] Option 5

[0203] Further substituted N-methyl-5-mercaptophenyl-1H-pyrimidin-2,4-dione intermediate (II) can also be converted into the desired compound of general formula (If) according to the invention, wherein X and Y are sulfur (S) (Scheme 6). Then, in the first step, compound (III) is converted into an intermediate of type (IX) in a suitable polar aprotic solvent (e.g., dioxane) using a suitable base or a suitable transition metal catalyst (e.g., tris(dibenzylacetone)dipalladium(O)) with a suitable ligand (e.g., 4,5-bis(diphenylphosphino)-9,9-dimethyloxanthracene) and a suitable base (e.g., diisopropyl(ethyl)amine). Depending on the circumstances, it may be necessary to intermediately protect the thiol group with a suitable protecting group. Subsequently, intermediate (IX) can be reacted with a haloalkane carboxylic acid containing various substituents using a suitable base to give the desired compound of general formula (If). In Scheme 6 below, Q, R... 2 R 3 and R 4 This has the meaning described above according to the present invention. Furthermore, R 1 R 5 R 6 R 7For example, but not limited to, hydrogen; X and Y, for example, but not limited to, sulfur; and G, for example, but not limited to, CH2. Furthermore, for clarity, the reaction pathway is described in Scheme 6 below, for example, but not limited to, the use of iodoacetic acid esters. Similar haloalkane carboxylic acids (halogen = bromine or chlorine) are also suitable for coupling with intermediate (IX).

[0204]

[0205] Option 6

[0206] Detailed synthetic examples of selected compounds of general formula (I) according to the present invention are given below. The example numbers mentioned correspond to the schemes numbered in Tables I.1 to I.33 below. The chemical examples described in the following sections... 1 H NMR, 13 C-NMR and 19 F-NMR spectral data ( 1 H NMR is 400MHz 13 C-NMR at 150MHz and 19 F-NMR was performed at 375 MHz using CDCl3, CD3OD, or d6-DMSO as solvents, with tetramethylsilane as the internal standard (δ = 0.00 ppm). The results were obtained using a Bruker instrument, and the signals are listed as follows: br = broad peak; s = singlet; d = doublet; t = triplet; dd = doublet; ddd = double doublet; m = multiplet; q = quartet; quintet; sext = sextet; sept = septet; dq = double quartet; dt = double triplet. In the case of diastereomer mixtures, report the significant signal for each of the two diastereomers, or report the characteristic signal of the dominant diastereomer. The abbreviations used for chemical groups have the following meanings, for example: 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.

[0207] Synthesis Example:

[0208] Example I.1-1: [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}thio)phenoxy]acetic acid 2-methoxyethyl ester

[0209]

[0210] To a solution of methyl ethylene glycol (0.012 g, 0.155 mmol) in 4 mL of dichloromethane, [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}thio)phenoxy]acetic acid (0.060 g, 0.119 mmol) was added sequentially, 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%). The mixture was stirred overnight at room temperature. The reaction mixture was purified by column chromatography on silica gel using a heptane / ethyl acetate gradient. This yielded 0.044 g (64% of the theoretical value) of 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}thio)phenoxy]acetic acid 2-methoxyethyl ester. 1 H-NMR(CDCl3δ,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).

[0211] Example I.2-1: (2RS)-2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}thio)phenoxy]propionic acid 2-methoxyethyl ester

[0212]

[0213] To a solution of methyl ethylene glycol (0.011 g, 0.150 mmol) in 4 mL of dichloromethane, (2RS)-2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}thio)phenoxy]propionic acid (0.060 g, 0.116 mmol) was added sequentially, 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%). The mixture was stirred overnight at room temperature. The reaction mixture was purified by column chromatography on silica gel using a heptane / ethyl acetate gradient. This yielded 0.056 g (80% of the theoretical value) 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}thio)phenoxy]propionic acid. 1 H-NMR(CDCl3δ,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).

[0214] 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

[0215]

[0216] To a solution of hydroxyacetonitrile (0.027 g, 0.286 mmol) in 10 mL of dichloromethane, add (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), then sequentially add 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 stir the mixture at room temperature for 2 h. Add water and dichloromethane to the reaction mixture, repeatedly extract the aqueous phase with dichloromethane, and dry the combined organic phases to sodium sulfate, removing the solvent under reduced pressure. After purification by column chromatography on silica gel using a gradient of n-heptane / ethyl acetate, 0.095 g (79% of the theoretical value) 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),6.9 4(d,1H),6.68(d,1H),6.29(s,1H),4.76(s,2H),4.74(s,2H),3.50(s,3H).

[0217] Example I.7-71: (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)tetrahydrofuran-2-ylmethyl acetate

[0218]

[0219] To a solution of tetrahydrofuran-2-ylmethanol (0.042 g, 0.412 mmol) in 15 mL of dichloromethane, add (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), followed by the sequential addition of 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%). The mixture is stirred at room temperature for 2 h. Water and dichloromethane are added to the reaction mixture. The aqueous phase is repeatedly extracted with dichloromethane. The combined organic phases are dried over sodium sulfate, and the solvent is removed under reduced pressure. After purification by column chromatography on silica gel using a gradient of n-heptane / ethyl acetate, 0.129 g (73% of the theoretical value) of a colorless solid was obtained. 1H-NMR(CDCl3δ,ppm)7.36(d,1H),7.14-7.10(m,1H),7.07-7.04(m,1H),7.01-6.97(m,1H),6.92(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).

[0220] 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-yl methyl acetate

[0221]

[0222] To a solution of pyridin-2-ylmethanol (0.028 g, 0.258 mmol) in 10 mL of dichloromethane, add (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 the sequential addition of 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%). The mixture is stirred at room temperature for 2 h. Water and dichloromethane are added to the reaction mixture. The aqueous phase is repeatedly extracted with dichloromethane. The combined organic phases are dried over sodium sulfate, and the solvent is removed under reduced pressure. After purification by column chromatography on silica gel using a gradient of n-heptane / ethyl acetate, 0.096 g (81% of the theoretical value) 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),7.14-7.0 8(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).

[0223] Example I.7-183: (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid 2-nitroethyl ester

[0224]

[0225] To a solution of (0.150 g, 0.306 mmol) of 2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid 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 sequentially, and the mixture was stirred under reflux for 5 h. The reaction mixture was left to stand overnight and stirred under reflux for another 5 h. Water and dichloromethane were added to the reaction mixture, and 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. The product was purified by column chromatography on silica gel using a heptane / acetone gradient, and then further purified by column chromatography on silica gel using a heptane / ethyl acetate gradient to obtain 0.036 g (20% of the theoretical value) of 2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid 2-nitroethyl ester. 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).

[0226] Example I.7-177: (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid 1-cyanoethyl ester

[0227]

[0228] To a solution of (0.160 g, 0.327 mmol) of 2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid in 4.0 mL of acetonitrile, 4-dimethylaminopyridine (0.005 g, 0.039 mmol), potassium carbonate (0.056 g, 0.404 mmol), and 2-bromopropionitrile (0.052 g, 0.389 mmol) were successively added, and the mixture was stirred at room temperature for 2 h and then refluxed for 1 h. Water and dichloromethane were added to the reaction mixture, and 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. Purified by column chromatography using a heptane / ethyl acetate gradient, followed by drying under reduced pressure at 40 °C, yielded 0.160 g (95% of the theoretical value) of 1-cyanoethyl 2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid. 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).

[0229] Example I.7-1: (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid 2-methoxyethyl ester

[0230]

[0231] Under a nitrogen atmosphere, indium(III) chloride (2.599 g, 11.749 mmol) was added to 46.32 mL of ethyl acetate (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy) in 4-methoxyethanol (5.520 g, 10.681 mmol), 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, and the aqueous phase was repeatedly extracted with ethyl acetate. The combined organic phases were washed with a saturated sodium chloride aqueous solution, dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel using a heptane / ethyl acetate gradient, 5.150 g (88% of the theoretical value) of a colorless solid was obtained. 1H-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,1 H),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).

[0232] Example I.7-94: (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid 1-methoxypropyl-2-yl ester

[0233]

[0234] Under a nitrogen atmosphere, indium(III) chloride (0.116 g, 0.527 mmol) was added to 4.0 mL of 1-methoxyprop-2-ol containing 2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid 2-methoxyethyl ester (0.160 g, 0.293 mmol). The reaction mixture was heated in a microwave reactor at 125 °C for 1.5 h. After cooling to room temperature, the reaction mixture was poured into water, and dichloromethane was added. 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 column chromatography using a gradient of n-heptane / ethyl acetate, 0.110 g (66% of the theoretical value) of 1-methoxypropyl-2-yl ester of (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid 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).

[0235] Example I.6-1: (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetic acid 2-methoxyethyl ester

[0236]

[0237] To a microwave-safe container under argon atmosphere, ethyl acetate (100 mg, 0.19 mmol) of 2-methoxyethanol (505 mg, 6.63 mmol) and indium(III) chloride (51.2 mg, 0.23 mmol) were added to ethyl acetate (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy) of 100 mg, 0.19 mmol. The reaction mixture was stirred at 115 °C for 120 min 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 the mixture was concentrated. The crude product was purified by column chromatography on silica gel using a gradient of n-heptane / ethyl acetate to obtain colorless oil form of (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetic acid 2-methoxyethyl ester (78 mg, 73% of theoretical value).

[0238] 1 H-NMR(CDCl3δ,ppm)7.87(d,1H),7.19(m,2H),7.03(t,1H),6.95(d,1H),6.88(d,1 H),6.28(s,1H),4.67(s,2H),4.25(t,2H),3.53(t,2H),3.50(s,3H),3.31(s,3H).

[0239] 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

[0240]

[0241] Under argon atmosphere, the mixture initially loaded with 1 ml of acetone containing (100 mg, 0.20 mmol) of (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetic acid, 38 mg, 0.30 mmol, and triethylamine (30 mg, 0.30 mmol) was stirred at room temperature for 2.5 h. After TLC monitoring, 13 mg, 0.10 mmol of bromoacetonitrile was added, and the mixture was stirred at room temperature for another 1 h. The reaction mixture was concentrated by adding 10 ml of water and 10 ml of dichloromethane. The organic phase was removed and the mixture was concentrated. The crude product was purified by column chromatography on silica gel using a gradient of n-heptane / ethyl acetate to obtain colorless oil form of (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)cyanomethyl acetate (104 mg, 95% of theoretical value).

[0242] 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).

[0243] 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

[0244]

[0245] Under argon atmosphere, the mixture initially loaded into 22 mL of dichloromethane, consisting 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), bromoacetonitrile (337 mg, 2.81 mmol), and triethylamine (380 mg, 3.75 mmol), was stirred at room temperature for 5 hours. The mixture was left to stand overnight, 10 mL of water was added, and the mixture was stirred again. The organic phase was removed and the mixture was concentrated. The crude product was purified by column chromatography on silica gel using a gradient of n-heptane / ethyl acetate to obtain colorless oil form of (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy) cyanomethyl acetate (598 mg, 55% of theoretical value).

[0246] 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).

[0247] Example I.9-176: (2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)cyanomethyl acetate

[0248]

[0249] Under argon atmosphere, methyl cyanoacetate (598 mg, 1.05 mmol) initially packed in 15 mL of N,N-dimethylacetamide, along with zinc cyanide (129 mg, 1.10 mmol) and tetrakis(triphenylphosphine)palladium(O) (121 mg, 0.10 mmol), was stirred at 180 °C for 1 hour. 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, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using a gradient of n-heptane / ethyl acetate to obtain colorless oil form of (2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)cyanomethyl acetate (232 mg, 42% of theoretical value).

[0250] 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).

[0251] Similar to the preparation examples cited above and described where appropriate, and taking into account general information relating to the preparation of substituted N-heterocyclic groups and N-heteroaryltetrahydropyrimidinones, the compounds cited below were obtained.

[0252]

[0253] Table I.1: Preferred compounds of formula (I.1) are compounds I.1-1 to I.1-406, wherein Q has the meaning given in the corresponding row of Table 1. Therefore, compounds I.1-1 to I.1-406 in Table I.1 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0254] Table 1:

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267] Table I.2: Preferred compounds of formula (I.2) are compounds I.2-1 to I.2-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.2-1 to I.2-406 in Table I.2 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0268]

[0269] Table I.3: Preferred compounds of formula (I.3) are compounds I.3-1 to I.3-406, where Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.3-1 to I.3-406 in Table I.3 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0270]

[0271] Table I.4: Preferred compounds of formula (I.4) are compounds I.4-1 to I.4-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.4-1 to I.4-406 in Table I.4 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0272]

[0273] Table I.5: Preferred compounds of formula (I.5) are compounds I.5-1 to I.5-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.5-1 to I.5-406 in Table I.5 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0274]

[0275] Table I.6: Preferred compounds of formula (I.6) are compounds I.6-1 to I.6-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.6-1 to I.6-406 in Table I.6 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0276]

[0277] Table I.7: Preferred compounds of formula (I.7) are compounds I.7-1 to I.7-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.7-1 to I.7-406 in Table I.7 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0278]

[0279] Table I.8: Preferred compounds of formula (I.8) are compounds I.8-1 to I.8-406, where Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.8-1 to I.8-406 in Table I.8 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0280]

[0281] Table I.9: Preferred compounds of formula (I.9) are compounds I.9-1 to I.9-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.9-1 to I.9-406 in Table I.9 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0282]

[0283] Table I.10: Preferred compounds of formula (I.10) are compounds I.10-1 to I.10-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.10-1 to I.10-406 in Table I.10 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0284]

[0285] Table I.11: Preferred compounds of formula (I.11) are compounds I.11-1 to I.11-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.11-1 to I.11-406 in Table I.11 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0286]

[0287] Table I.12: Preferred compounds of formula (I.12) are compounds I.12-1 to I.12-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.12-1 to I.12-406 in Table I.12 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0288]

[0289] Table I.13: Preferred compounds of formula (I.13) are compounds I.13-1 to I.13-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.13-1 to I.13-406 in Table I.13 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0290]

[0291] Table I.14: Preferred compounds of formula (I.14) are compounds I.14-1 to I.14-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.14-1 to I.14-406 in Table I.14 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0292]

[0293] Table I.15: Preferred compounds of formula (I.15) are compounds I.15-1 to I.15-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.15-1 to I.15-406 in Table I.15 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0294]

[0295] Table I.16: Preferred compounds of formula (I.16) are compounds I.16-1 to I.16-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.16-1 to I.16-406 in Table I.16 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0296]

[0297] Table I.17: Preferred compounds of formula (I.17) are compounds I.17-1 to I.17-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.17-1 to I.17-406 in Table I.17 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0298]

[0299] Table I.18: Preferred compounds of formula (I.18) are compounds I.18-1 to I.18-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.18-1 to I.18-406 in Table I.18 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0300]

[0301] Table I.19: Preferred compounds of formula (I.19) are compounds I.19-1 to I.19-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.19-1 to I.19-406 in Table I.19 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0302]

[0303] Table I.20: Preferred compounds of formula (I.20) are compounds I.20-1 to I.20-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.20-1 to I.20-406 in Table I.20 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0304]

[0305] Table I.21: Preferred compounds of formula (I.21) are compounds I.21-1 to I.21-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.21-1 to I.21-406 in Table I.21 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0306]

[0307] Table I.22: Preferred compounds of formula (I.22) are compounds I.22-1 to I.22-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.22-1 to I.22-406 in Table I.22 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0308]

[0309] Table I.23: Preferred compounds of formula (I.23) are compounds I.23-1 to I.23-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.23-1 to I.23-406 in Table I.23 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0310]

[0311] Table I.24: Preferred compounds of formula (I.24) are compounds I.24-1 to I.24-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.24-1 to I.24-406 in Table I.24 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0312]

[0313] Table I.25: Preferred compounds of formula (I.25) are compounds I.25-1 to I.25-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.25-1 to I.25-406 in Table I.25 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0314]

[0315] Table I.26: Preferred compounds of formula (I.26) are compounds I.26-1 to I.26-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.26-1 to I.26-406 in Table I.26 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0316]

[0317] Table I.27: Preferred compounds of formula (I.27) are compounds I.27-1 to I.27-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.27-1 to I.27-406 in Table I.27 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0318]

[0319] Table I.28: Preferred compounds of formula (I.28) are compounds I.28-1 to I.28-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.28-1 to I.28-406 in Table I.28 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0320]

[0321] Table I.29: Preferred compounds of formula (I.29) are compounds I.29-1 to I.29-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.29-1 to I.29-406 in Table I.29 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0322]

[0323] Table I.30: Preferred compounds of formula (I.30) are compounds I.30-1 to I.30-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.30-1 to I.30-406 in Table I.30 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0324]

[0325] Table I.31: Preferred compounds of formula (I.31) are compounds I.31-1 to I.31-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.31-1 to I.31-406 in Table I.31 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0326]

[0327] Table I.32: Preferred compounds of formula (I.32) are compounds I.32-1 to I.32-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.32-1 to I.32-406 in Table I.32 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0328]

[0329] Table I.33: Preferred compounds of formula (I.33) are compounds I.33-1 to I.33-406, wherein Q has the meaning indicated by the corresponding row in Table 1. Therefore, compounds I.33-1 to I.33-406 in Table I.33 are defined by the meaning of the corresponding entries 1 to 406 of Q in Table 1.

[0330] NMR data of selected embodiments: 1H NMR data of selected embodiments of compounds of general formula (I) are presented in two different ways, namely (a) conventional NMR evaluation and description or (b) a list of 1H NMR peaks according to the method described below.

[0331] a) Conventional NMR description

[0332] 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).

[0333] Example I.7-121: 1 H-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).

[0334] 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).

[0335] 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).

[0336] Example I.8-335: 1 H-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).

[0337] 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).

[0338] 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).

[0339] 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).

[0340] Example I.20-176: 1 H-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).

[0341] 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).

[0342] b) NMR peak listing method

[0343] Selected Implementation 1 H NMR data with 1 The H NMR peaks are presented in a list format. For each signal peak, the δ value in ppm is listed first, followed by the signal intensity in parentheses. δ value-signal intensity pairs for different signal peaks are listed, separated by semicolons.

[0344] Therefore, the peak list in the embodiment takes the following form:

[0345] δ1 (Intensity 1); δ2 (Intensity 2); ...; δ i (strength i );……;δ n (strength n )

[0346] The intensity of a sharp signal is correlated with the signal height (in cm) in the printed example of the NMR spectrum, and the true ratio of signal intensity is displayed. In the case of a broad signal, multiple peaks or the middle portion of the signal can be displayed, along with their relative intensity compared to the strongest signal in the spectrum.

[0347] To calibrate the chemical shifts of a 1H NMR spectrum, the chemical shifts of tetramethylsilane and / or the solvent are used, especially in the case of spectra measured in DMSO. Therefore, a tetramethylsilane peak may, but is not necessarily, appear in the NMR peak list.

[0348] The list of 1H NMR peaks is similar to that of a regular 1H NMR print and therefore typically includes all the peaks listed in a regular NMR description.

[0349] In addition, like conventional 1H NMR prints, they can display solvent signals, stereoisomer signals of the target compounds, which are also the subject of this invention, and / or impurity peaks.

[0350] In our 1H NMR peak list for compound signal reports in the solvent and / or water δ range, we show typical solvent peaks, such as the DMSO peak in DMSO-D6 and water peaks, which generally have high average intensities.

[0351] The peaks of the stereoisomers of the target compound and / or the peaks of impurities typically have lower average intensities than the peaks of the target compound (e.g., having a purity >90%).

[0352] Such stereoisomers and / or impurities can be typical of the corresponding preparation methods. Therefore, referring to the "byproduct fingerprint," their peaks can help identify the reproducibility of the preparation process in this case.

[0353] A specialist who calculates the peaks of a target compound using known methods (MestreC, ACD simulation, but also with expected values ​​based on empirical assessment) can separate the peaks of the target compound (with an optional additional intensity filter). This separation is similar to the relevant peak selection in a conventional 1H NMR description.

[0354] Further details of the 1H NMR peak list can be found in Research Disclosure Database number 564025.

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385] The present invention further provides one or more compounds of general formula (I) according to the invention as defined above, preferably in one of the embodiments deemed preferred or particularly preferred, and in particular, in their respective cases, one or more compounds of formulas (I.1) to (I.33) as defined above and / or salts thereof for use as herbicides and / or plant growth regulators, preferably in crops of useful plants and / or ornamental plants.

[0386] The present invention further provides a method for controlling harmful plants and / or regulating plant growth, characterized in that an effective amount of

[0387] - One or more compounds of general formula (I) according to the invention as defined above, preferably in one of the embodiments considered preferred or particularly preferred, and / or salts thereof, particularly in their respective cases one or more compounds of formulas (I.1) to (I.33) as defined above and / or salts thereof, or

[0388] -The compositions according to the invention as defined below

[0389] Apply to (harmful) plants, (harmful) plant seeds, (harmful) plants growing in or on the soil, or cultivation area.

[0390] This invention also provides a method for controlling unwanted plants, preferably used on crops with beneficial plants, characterized in that an effective amount of...

[0391] - One or more compounds of general formula (I) as defined above, preferably in one of the embodiments deemed preferred or particularly preferred, and / or salts thereof, particularly in their respective cases one or more compounds of formulas (I.1) to (I.33) as defined above and / or salts thereof, or

[0392] -The compositions according to the invention as defined below

[0393] It is applied to unwanted plants (e.g., harmful plants such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), seeds of unwanted plants (i.e., plant seeds, such as grains, seeds or vegetative reproductive organs such as tubers or budding shoots), soil in which unwanted plants grow or on it (e.g., soil in crop-growing land and non-crop-growing land) or cultivation areas (i.e., areas where unwanted plants will grow).

[0394] The present invention further provides a method for controlling and regulating plant growth, preferably used for useful plants, characterized in that an effective amount of

[0395] - One or more compounds of general formula (I) as defined above, preferably in one of the embodiments deemed preferred or particularly preferred, and / or salts thereof, particularly in their respective cases one or more compounds of formulas (I.1) to (I.33) as defined above and / or salts thereof, or

[0396] -The compositions according to the invention as defined below

[0397] It is applied to plants, plant seeds (i.e., plant seeds, such as grains, seeds or vegetative reproductive organs such as tubers or budding shoots), soil in which or on which the plant grows (e.g., soil in crop land and non-crop land), or cultivated areas (i.e., areas where the plant will grow).

[0398] Here, compounds of general formula (I) according to the invention or compositions according to the invention can be applied, for example, by pre-seeding (and, if appropriate, by incorporation into the soil), pre-emergence and / or post-emergence methods (pre-emergence and / or post-emergence methods). Specific examples of some representative monocotyledonous and dicotyledonous weeds that can be controlled by compounds according to the invention are as follows, although not intended to be limited to specific species.

[0399] In the method for controlling harmful plants or regulating plant growth according to the present invention, it is preferred to use one or more compounds of general formula (I) and / or salts thereof to control harmful plants or regulate the growth of useful or ornamental plants, wherein in a preferred embodiment, the useful or ornamental plants are transgenic plants.

[0400] Compounds of general formula (I) and / or salts thereof according to the present invention are suitable for controlling monocotyledonous and dicotyledonous harmful plants of the following genera:

[0401] Genus of monocotyledonous harmful plants: *Aegilops*, *Agropyron*, *Agrostis*, *Alopecurus*, *Apera*, *Avena*, *Brachiaria*, *Bromus*, *Cenchrus*, *Commelina*, *Cynodon*, *Cyperus*, *Dactyloctenium*, *Digitaria*, *Echinochloa*, *Eleocharis*, *Eleusine*, *Eragrostis*, *Wild Millet* The genera *Eriochloa*, *Festuca*, *Fimbristylis*, *Heteranthera*, *Imperata*, *Ischaemum*, *Leptochloa*, *Lolium*, *Monochoria*, *Panicum*, *Paspalum*, *Phalaris*, *Phleum*, *Poa*, *Rottboellia*, *Sagittaria*, *Scirpus*, *Setaria*, and *Sorghum*.

[0402] Genus of harmful dicotyledonous plants:The genera *Abutilon*, *Amaranthus*, *Ambrosia*, *Anoda*, *Anthemis*, *Aphanes*, *Artemisia*, *Atriplex*, *Beilis*, *Bidens*, *Capsella*, *Carduus*, *Cassia*, *Centaurea*, *Chenopodium*, and *Cirsium* are all related to the plant family. ), Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria Genus (Matricaria), Genus (Mentha), Genus (Mercurialis), Genus (Mullugo), Genus (Myosotis), Genus (Papaver), Genus (Pharbitis), Genus (Plantago), Genus (Polygonum), Genus (Portulaca), Genus (Ranunculus), Genus (Raphanus), Genus (Rorippa), Genus (Rotala), Genus (Rumex), Genus (Salvia). The genera *alsola*, *Senecio*, *Sesbania*, *Sida*, *Sinapis*, *Solanum*, *Sonchus*, *Sphenoclea*, *Stellaria*, *Taraxacum*, *Thlaspi*, *Trifolium*, *Urtica*, *Veronica*, *Viola*, and *Xanthium*.

[0403] When the compound of general formula (I) according to the invention is applied to the soil surface before the emergence of harmful plants (tree weeds and / or broadleaf weeds) (pre-emergence method), it either completely prevents the emergence of tree weeds and / or broadleaf weeds, or causes them to grow to the cotyledon stage and then stop growing, eventually dying completely after 3 to 4 weeks.

[0404] When the compound of general formula (I) according to the invention is applied to the green parts of plants after emergence, their growth ceases after treatment, harmful plants remain in the growth stage at the time of application, or they die completely after a certain period of time, thereby eliminating harmful weed competitors to crop plants very early and continuously.

[0405] Although the compounds of general formula (I) according to the present invention exhibit outstanding herbicidal activity against both monocot and dicot weeds, they are suitable for economically important crop plants, such as dicotyledonous genera: *Arachis*, *Beta*, *Brassica*, *Cucumis*, *Cucurbita*, *Helianthus*, *Daucus*, *Glycine*, *Gossypium*, *Ipomoea*, *Lactuca*, *Linum*, *Lycopersicon*, *Miscanthus*, and *Nicotiana*. Monocotyledonous crops of the genera *Phaseolus*, *Pisum*, *Solanum*, *Vicia*, or the following genera: *Allium*, *Ananas*, *Asparagus*, *Avena*, *Hordeum*, *Oryza*, *Panicum*, *Saccharum*, *Secale*, *Sorghum*, *Triticale*, *Triticum*, and *Zea*, are only slightly damaged or not damaged at all, depending on the structure and application rate of the corresponding compound of formula (I) according to the invention. For these reasons, this compound is very suitable for the selective control of unwanted plant growth in plant crops, such as useful or ornamental plants in agriculture.

[0406] Furthermore, compounds of general formula (I) according to the invention (depending on their corresponding structures and the application rates used) exhibit outstanding growth-regulating properties in crop plants. They modulate the plant's own metabolism and can therefore be used to controllably influence plant components, and promote harvesting, for example, by inducing drying and dwarfing growth. In addition, they are also suitable for general control and suppression of unwanted vegetative growth without killing the plant in the process. Suppressing vegetative growth is important for many monocotyledonous and dicotyledonous crops because, for example, this can reduce or completely prevent lodging.

[0407] Due to their herbicidal and plant growth regulator properties, compounds of general formula (I) according to the present invention can also be used to control harmful plants in genetically modified plants or plant crops modified through conventional mutagenesis. Generally, transgenic plants are characterized by particularly advantageous properties, such as resistance to certain pesticides (especially herbicides), and resistance to plant diseases or pathogens of plant diseases (e.g., certain insects or microorganisms such as fungi, bacteria, or viruses). Other specific characteristics relate to, for example, the quantity, quality, storability, composition, and specific components of the harvest. For example, transgenic plants with increased starch content or altered starch quality, or those with different fatty acid compositions in their harvests, are known.

[0408] With regard to genetically modified crops, it is preferred to use compounds of general formula (I) according to the invention and / or their salts in genetically modified crops of economically important useful plants and ornamental plants, such as cereals like wheat, barley, rye, oats, millet, rice and corn, or other crops like sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.

[0409] Preferably, the compound of general formula (I) according to the invention is used as a herbicide on crops with useful plants that can resist or have become resistant to the phytotoxic effects of the herbicide through recombination.

[0410] Due to their herbicidal and plant growth regulator properties, compounds of general formula (I) according to the invention can also be used to control harmful plants in known or developing genetically modified plant crops. Generally, transgenic plants are characterized by particularly advantageous properties, such as resistance to certain pesticides (especially certain herbicides), plant diseases or pathogens of plant diseases (e.g., certain insects or microorganisms such as fungi, bacteria, or viruses). Other specific characteristics relate to, for example, the quantity, quality, storability, composition, and specific components of the harvest. For example, transgenic plants with increased starch content or altered starch quality, or harvests with different fatty acid compositions, are known to have these properties. Other special properties may include tolerance or resistance to abiotic stresses such as heat, cold, drought, salinity, and ultraviolet radiation.

[0411] The use of compounds of general formula (I) according to the invention or salts thereof in genetically modified crops of economically important useful plants and ornamental plants is preferred, such as cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and corn, or other crops such as sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.

[0412] It is preferred to use compounds of general formula (I) as herbicides in crops with useful plants that are resistant to or have become resistant to the phytotoxic effects of herbicides through recombination.

[0413] Conventional methods for producing new plants with altered properties compared to existing plants include, for example, traditional breeding methods and mutation generation. Alternatively, new plants with altered properties can be produced using recombination methods.

[0414] Those skilled in the art are aware of a multitude of molecular biotechnologies capable of producing novel transgenic plants with altered properties. For such genetic manipulation, nucleic acid molecules that allow mutation or sequence alteration through DNA sequence recombination can be introduced into plasmids. Standard methods can be employed, such as base exchange, removal of partial sequences, or addition of natural or synthetic sequences. To link DNA fragments together, aptamers (adaptors) or linkers can be added to the fragments.

[0415] For example, plant cells with reduced gene product activity can be generated by expressing at least one corresponding antisense RNA, a sense RNA for co-inhibition, or by expressing at least one appropriately constructed nuclease that specifically cleaves the transcript of the aforementioned gene product.

[0416] Therefore, one can first use a DNA molecule containing the entire coding sequence of the gene product, including any flanking sequences that may be present, or a DNA molecule containing only a portion of the coding sequence, in which case these portions must be long enough to produce an antisense effect in the cell. Alternatively, a DNA sequence that is highly homologous to but not identical to the coding sequence of the gene product can also be used.

[0417] When nucleic acid molecules are expressed in plants, the synthesized proteins can be localized to any desired compartment of the plant cell. However, to achieve localization in a specific compartment, the coding region can be, for example, linked to a DNA sequence that ensures localization in that specific compartment. Such sequences are known to those skilled in the art (e.g., see Braun et al., EMBO J.11 (1992), 3219-3227). Nucleic acid molecules can also be expressed in organelles of plant cells.

[0418] Transgenic plant cells can be regenerated using known techniques to produce whole plants. In principle, transgenic plants can be plants of any desired plant species, including both monocots and dicots.

[0419] Therefore, transgenic plants with altered characteristics can be obtained through overexpression, repression, or inhibition of homologous (=natural) genes or gene sequences, or through the expression of heterologous (=foreign) genes or gene sequences.

[0420] Preferably, the compound of general formula (I) according to the invention is used in transgenic crops that are resistant to growth regulators such as dicamba, or to herbicides that inhibit basic plant enzymes such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS), or hydroxyphenylpyruvate dioxygenase (HPPD), or to herbicides derived from sulfonylureas, glyphosate, glufosinate, or benzoylisoxazoles and similar active ingredients.

[0421] When compounds of general formula (I) according to the present invention are used in genetically modified crops, not only do they exhibit the efficacy against harmful plants observed in other crops, but they also frequently exhibit specific effects when applied to particular genetically modified crops, such as altering or particularly broadening the spectrum of controllable weeds, allowing for altered application rates, preferably good compatibility with herbicides to which genetically modified crops are resistant, and influencing the growth and yield of genetically modified crop plants.

[0422] Therefore, the present invention also relates to the use of compounds of general formula (I) and / or salts thereof according to the present invention as herbicides for the control of harmful plants in useful or ornamental crops, optionally in genetically modified crops.

[0423] In pre- or post-emergence methods, use in cereals is preferred, with corn, wheat, barley, rye, oats, millet, or rice being the most preferred.

[0424] It is also preferred to use it in soybeans in pre-emergence or post-emergence methods.

[0425] The use of the present invention for controlling harmful plants or regulating plant growth also includes cases where the compound of general formula (I) or its salt is formed from a precursor ("prodrug") only after it has been applied to the plant, inside the plant or in the soil.

[0426] The present invention also provides the use of one or more compounds of general formula (I) or salts thereof or compositions of the present invention (as defined below) (in one method) for controlling harmful plants or regulating plant growth, characterized in that an effective amount of one or more compounds of general formula (I) or salts thereof is applied to plants (harmful plants, if suitable to be used with beneficial plants), plant seeds, soil on or in which plants grow, or cultivation areas.

[0427] The present invention also provides a weed-controlling and / or plant growth-regulating composition, characterized in that the composition comprises

[0428] (a) One or more compounds of general formula (I) as defined above, preferably in one of the embodiments considered preferred or particularly preferred, and / or salts thereof, particularly in their respective cases one or more compounds of formulas (I.1) to (I.33) as defined above and / or salts thereof.

[0429] and

[0430] (b) One or more additional substances selected from groups (i) and / or (ii):

[0431] (i) one or more other agricultural chemically active substances, preferably insecticides, acaricides, nematicides, other herbicides (i.e., those that do not conform to the general formula (I) defined above), fungicides, safeners, fertilizers and / or other growth regulators,

[0432] (ii) One or more formulation adjuvants commonly used in plant protection.

[0433] Here, the additional agrochemically active substances of component (i) of the composition of the present invention are preferably selected from the group of substances mentioned in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0434] The herbicidal or plant growth regulating composition according to the invention comprises preferably one, two, three or more formulation adjuvants (ii) commonly used in crop protection, selected from surfactants, emulsifiers, dispersants, film-forming agents, thickeners, inorganic salts, dusting agents, carriers that are solid at 25°C and 1013 mbar, preferably adsorbent particulate inert materials, wetting agents, antioxidants, stabilizers, buffers, defoamers, water, and organic solvents, preferably organic solvents that are miscible with water in any proportion at 25°C and 1013 mbar.

[0435] The compounds of general formula (I) according to the invention can be used in conventional formulations as wettable powders, emulsifiable concentrates, sprayable solutions, powdered products, or granules. The invention therefore also provides herbicidal and plant growth regulating compositions comprising compounds of general formula (I) and / or salts thereof.

[0436] Compounds of general formula (I) and / or salts thereof according to the present invention can be formulated in a variety of ways according to desired biological and / or physicochemical parameters. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), coatings, granules for broadcasting and soil application, granules in microparticle form (GR), spray granules, absorbent and adsorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, and waxes.

[0437] These individual formulations and formulation aids, such as inert materials, surfactants, solvents, and additional additives, are known to those skilled in the art and are described, for example: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ; HvOlphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, NY; C. Marsden, "Solvents Guide", 2nd ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MCPubl. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; [Interface-active Ethylene Oxide] Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0438] Wettable powders are formulations that can be uniformly dispersed in water. In addition to the active ingredient, they include ionic and / or nonionic surfactants (wetting agents, dispersants) other than diluents or inert substances, such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyethylene glycol ether sulfates, alkyl sulfonates, alkylbenzene sulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyl taurate. To produce wettable powders, the active herbicidal ingredient is finely ground, for example in conventional equipment such as hammer mills, blower mills, and air mills, and mixed simultaneously or subsequently with formulation adjuvants.

[0439] Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of relatively high-boiling aromatics or hydrocarbons or organic solvents, and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used include: calcium alkyl aryl sulfonates such as calcium dodecylbenzene sulfonate, or nonionic emulsifiers such as fatty acid polyethylene glycol esters, alkyl aryl polyethylene glycol ethers, fatty alcohol polyethylene glycol 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.

[0440] Powdered products are obtained by grinding active ingredients together with finely dispersed solids such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0441] Suspension concentrates can be water-based or oil-based. They can be produced, for example, by wet milling using a standard commercially available ball mill and optionally by adding surfactants such as those listed above for other formulation types.

[0442] Emulsions such as oil-in-water emulsions (EW) can be produced, for example, by means of agitators, colloid mills and / or static mixers, using aqueous organic solvents and optionally surfactants such as those listed above for other formulation types.

[0443] Granules can be prepared by spraying the active ingredient onto an adsorbent granular inert material or by applying a concentrated active ingredient to a carrier material such as sand, kaolin, or granular inert material using a binder such as polyvinyl alcohol, sodium polyacrylate, or mineral oil. Suitable active ingredients can also be granulated using conventional methods for producing fertilizer granules—if necessary, they can be mixed with fertilizer.

[0444] The production of water-dispersible granules generally employs conventional processes, such as spray drying, fluidized bed granulation, disc granulation, mixing with a high-speed mixer, and extrusion without solid inert materials.

[0445] For the production of disc pellets, fluidized bed pellets, extruder pellets, and spray pellets, see, for example, the methods in "Spray-Drying Handbook," 3rd edition, 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration," Chemical and Engineering, 1967, p. 147 and below; and "Perry's Chemical Engineer's Handbook," 5th edition, McGraw-Hill, New York, 1973, pp. 8-57.

[0446] For further details on the formulation of crop protection compositions, see, for example, G.K. Lingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96, and JD. F. Reyer and SAEvans, "Weed Control Handbook", 5th edition, Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

[0447] The agricultural chemical formulations of the present invention, preferably herbicidal or plant growth regulating compositions, preferably contain 0.1 to 99% by weight, more preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, and especially preferably 2 to 80% by weight of the active ingredient of general formula (I) and its salts.

[0448] In wettable powders, the concentration of the active ingredient is, for example, from about 10% to 90% by weight, with the remainder made up to 100% by weight being conventional formulation components. In emulsifiable concentrates, the concentration of the active ingredient can be from about 1% to 90% by weight, and preferably from 5% to 80% by weight. Formulations in powder form contain 1% to 30% by weight of the active ingredient, preferably typically from 5% to 20% by weight; sprayable solutions contain about 0.05% to 80% by weight, preferably from 2% to 50% by weight of the active ingredient. In the case of water-dispersible granules, the content of the active ingredient depends in part on whether the active compound is in liquid or solid form, and on the type of granulation aid, filler, etc., used. In water-dispersible granules, the content of the active ingredient is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

[0449] Furthermore, the active ingredients mentioned optionally include, in their respective cases, conventional binders, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and reagents that affect pH and viscosity. Examples of formulation aids are particularly documented in "Chemistry and Technology of Agrochemical Formulations", ed. D.A. Knowles, Kluwer Academic Publishers (1998).

[0450] Compounds of general formula (I) according to the invention, or salts thereof, may be used in their own form or in formulations (compositions) in combination with other pesticide active substances (e.g., insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and / or growth regulators), for example, as finished formulations or canned mixtures. Here, combined formulations can be prepared based on the above-described formulations, taking into account the physical properties and stability of the active ingredients to be combined.

[0451] Combination partners that can be used in combination with compounds of general formula (I) according to the invention in mixed formulations or canned mixtures are, for example, known active ingredients, based on, for example, inhibition of acetyllactone synthase, acetyl-CoA carboxylase, cellulase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytopenic lycopene desaturase, photosystem I, photosystem II, and 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.

[0452] Of particular value is the selective control of harmful plants in crops containing both beneficial and ornamental plants. Although compounds of formula (I) according to the invention have shown very good to sufficient selectivity in a wide range of crops, in principle, phytotoxicity may occur in some crops, especially when mixed with other herbicides of lower selectivity. In this regard, combinations of compounds of formula (I) according to the invention of particular interest are those comprising compound (I) or combinations thereof with other herbicides or pesticides and safeners. Safeners applied at an effective detoxifying level reduce the phytotoxic side effects of herbicides / pesticides used in, for example, important economic crops such as cereals (wheat, barley, rye, maize, rice, millet), sugar beets, sugarcane, rapeseed, cotton, and soybeans, preferably cereals.

[0453] The weight ratio of herbicide (mixture) to safener typically depends on the herbicide application rate and the efficacy of the safener used, and can vary over a wide range, for example, from 200:1 to 1:200, preferably from 100:1 to 1:100, and particularly from 20:1 to 1:20. Similar to compounds of general formula (I) or mixtures thereof, safeners can be formulated with additional herbicides / pesticides and provided and used as finished formulations or tank mixtures containing herbicides.

[0454] For application, commercially available herbicide formulations or herbicide safener formulations are diluted in the conventional manner where appropriate, such as with water in the case of wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Powder formulations, granules or broadcast granules for soil application, and sprayable solutions are generally not diluted with additional inert substances before application.

[0455] The application rate of the compound of formula (I) and / or its salts according to the invention is influenced to some extent by external conditions, such as temperature and humidity. The application rate can vary over a wide range. For application as a herbicide to control harmful plants, the total amount of the compound of formula (I) and its salts according to the invention is preferably 0.001 to 10.0 kg / ha, more preferably 0.005 to 5 kg / ha, more preferably 0.01 to 1.5 kg / ha, and particularly preferably 0.05 to 1 kg / ha. This is suitable for both pre-emergence and post-emergence application.

[0456] When compounds of general formula (I) according to the invention and / or their salts are used as plant growth regulators, for example as stem stabilizers, for crops similar to those mentioned above, preferably cereal crops such as wheat, barley, rye, triticale, millet, rice, or maize, the total application rate is preferably 0.001 to 2 kg / ha, more preferably 0.005 to 1 kg / ha, particularly 10 to 500 g / ha, and very particularly preferably 20 to 250 g / ha. This is suitable for both pre-emergence and post-emergence application.

[0457] Application as a stem stabilizer can be carried out at any stage of plant growth. Preferably, it is applied, for example, after tillering and at the onset of longitudinal growth.

[0458] Alternatively, seed treatment can be used for application as a plant growth regulator, including various seed dressing and coating techniques. The application rate depends on the specific technique and can be determined in preliminary testing.

[0459] Combinatorial partners of compounds of general formula (I) of the present invention that can be used in compositions (e.g., mixtures or tank blends) according to the present invention are, for example, known active ingredients based on, for example, inhibition of acetyllactate synthase, acetyl-CoA carboxylase, cellulase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytopenic oleoresin, 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 Soc. of Chemistry, 2012, and the references therein. Known herbicides or plant growth regulators that can be combined with the compounds of the present invention are, for example, substances in which the active ingredient is represented by its “common name” according to the International Organization for Standardization (ISO) or by its chemical name or by a code. These always include all forms of use, such as acids, salts, esters, and all isomers, such as stereoisomers and optical isomers, even if not explicitly mentioned.

[0460] An example of such a weed-control mix is:

[0461] Acetochlor, trifluralin, trifluralin-sodium, bensulfuron, metolachlor, chlorpyrifos, quizalofop-P-ethyl, quizalofop-P-ethyl, atrazine, azoxystrobin, amadochlor, pyrimisulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, cyclopropimidic acid, cyclopropimidic acid-potassium, cyclopropimidic acid-methyl, chlorpyrifos, chlorpyrifos, ammonium aminosulfonate, sparphos, sulfadiazine, atrazine, pyrimisulfuron, tetrazalofop-P-ethyl, flubutyroxyfen, chlorpyrifos-ethyl, fluazinam, furazolidone, bensulfuron-methyl Phosphamidon, dimethoate, bentazon, bispyribac-sodium, pyrazosulfuron, bicyclopyranone, carbamate, bispyribac-sodium, bispyribac-sodium, bispyribac-sodium, chlorpyrifos, bromophenoxim, bromobenzonitrile, bromobenzonitrile-butyrate, bromobenzonitrile-potassium, bromobenzonitrile-heptanoate and bromobenzonitrile-octanoate, hydroxylone, butachlor, flupropyrazosulfuron, chlorpyrifos, butachlor, terbufos, butachlor, butachlor, butachlor, carfentrazone, carfentrazone, carfentrazone-ethyl, chlorpyrifos, chlorobromosulfuron, chlorpyrifos-sodium, oat ester , ... (cloransulam-methyl), bensulfuron, cyanamide, cyanazine, cyclopyrimorate, cyclosulfamuron, thiamethoxam, cyhalofop, cyhalofop-butyl, cyclopyrimorate, 2,4-D, 2,4-D-butoxyethyl, 2,4-D-butyl, 2,4-D-dimethylammonium, 2,4-D-diethanolamine, 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, 2,4-D-Triisopropanolammonium and 2,4-D-Triethanolamine, 2,4-DB, 2,4-DB-Butyl, 2,4-DB-Dimethylammonium, 2,4-DB-Isooctyl, 2,4-DB-Potassium and 2,4-DB-sodium, sapura (sapura), basil, dazomet, n-decyl alcohol, betaine, desulfuron-pyrazosulfuron (DTP), dicamba, diquat, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dipropionic acid, dipropionic acid-P, quizalofop-P-methyl, quizalofop-P-methyl, dichlorvos, pyrifluquinazon, flupyrazole, flupyrazole hydrazone, flupyrazole hydrazone-sodium, oxazolone, piperazine, metolachlor, isoamyl ether, dimethyl phenoxychloride, dimethyl phenoxychloride-P, dimetrasulfuron, dichlorvos , terbufenozide, glyphosate, diquat dibromide, flusulfanilamide, diuron, DNOC, fenpropathrin, EPTC, pendimethalin, ethylbutenylsulfuron, azoxystrobin, azoxystrobin-methyl, ethoxysulfuron, ethoxysulfuron-ethyl, ethoxysulfuron, ethoxysulfuron, ethoxysulfuron, F-9600, F-5231 (i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide), F-7967 (i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, tetrazolium, fenoxaprop-M-isopropyl, fenoxaprop-M-methyl, pyrimisulfuron, fenoxam, fluazifop, fenoxam-P, fenoxam-butyl, fenoxam-P-butyl, fluazifop-sulfuron, fluazifop-sodium, flupyrsulfuron, fluazifop-sulfuron, fluazifop-sulfuron, fluthiamethoxam, flufenpyr, flufenpyr Flupyridazine-ethyl, pyrazosulfuron, flumiclorac, flumiclosulfuron-pentyl, propyzoxystrobin, fenfluridine, fenfluridine-butyl, fenfluridine-dimethylammonium and fenfluridine-methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrimisulfuron, flupyrimisulfuron-methyl-sodium, fluridone, flurflufenoxam, flupyridine, clopyralid, furazolidone, cyhalofop-methyl, flusulfanilamide, flusulfanilamide-sodium, formamide-sulfuron, phosphonium, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, and more. Ammonium phosphine-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium and glyphosate trimethyl sulfide, H-9201 (i.e., O-(2,4-dimethyl-6-nitrophenyl)-O-ethylisopropylthiophosphoramide), halauxifen, halauxifen-methyl, flunisulfonamide, chlorpyrifos, chlorpyrifos-methyl, haloxy-haloxy-P, haloxy-haloxy-Ethoxy-Ethoxy-Ethoxy-Ethoxy-Methyl, haloxy-haloxy-P-methyl, cycloazinone, HW-02 (i.e., 1-(dimethoxyphosphoryl)ethyl(2,4-dichlorophenoxy) (Acetyl)acetate), imidacloprid, imidacloprid-methyl, methoxyimidacloprid, methoxyimidacloprid-ammonium, methyl imidacloprid, methyl imidacloprid-ammonium, metsulfuron-methyl, metsulfuron-isopropylammonium, metsulfuron-methyl, metsulfuron-ammonium, imidacloprid, immonium, pyrazosulfuron, indaziflam, iodosulfuron-methyl-sodium, iodobenzonitrile, iodobenzonitrile-octanoate, iodobenzonitrile-potassium and sodium, ipfencarbazone, isoproturon, isoxaflutole, isoxaflutole, isoxazolidinone, terazolidinone, 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, flufenoxuron, cyclohexane, linuron, MCPA, MCPA-butoxyethyl, MCPA-dimethylammonium, MCPA-2-ethylhexyl, MCPA-isopropylammonium, MCPA-potassium and sodium, MCPB, MCPB-methyl, MCPB-ethyl and MCPB-sodium, mecopropionic acid, mecopropionic acid-sodium and butoxyethyl, mecopropionic acid-P, mecopropionic acid-P-butoxyethyl, mecopropionic acid-P-dimethylammonium, mecopropionic acid-P-2-ethylhexyl and potassium, benzthiamethoxam, flusulfanilamide, mesosulfuron-methyl, mesosulfuron-methyl, mesosulfuron-methyl, nicosulfuron, thiazoline, vemurafen, oxazolidinyl, benzalkonium chloride, pyrazosulfuron-methyl, dimethoate, chlorpyrifos Metazosulfuron, methizopyrsulfuron, methizolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, sulfadiazine, methoxyfenozide, metsulfuron, metsulfuron-methyl, quizalofop-p-ethyl, chlorpyrifos, chlorpyrifos, monosulfuron-ester, MT-5950 (N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide), NGGC-011, dichlorvos, NC-310 (4-(2,4-Dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole), glyphosate, nicosulfuron, nonanoic acid (n-nonanoic acid), dapoxuron, oleic acid (fatty acids), pyrimethanil, pyrimethanil, amosulfuron, propyzoxystrobin, oxadiazon, cyclopyrimethanil, tebufenozide, ethoxyflufenozide, paraquat, paraquat dihydrochloride, chlorpyrifos, nitrofurazone, penoxsulam, pentachlorophenol, cyclopyrimethanil, clethodim, petroleum oils, betaine, chlorpyrifos, flupyridine, flupyrflufenozide, cyclopyrrolizamide, pretilachlor, flupyrsulfuron, flupyrsulfuron-methyl, amosulfuron Phoxim, cyclobenzanone, propiconazole, propiconazole, chlorpyrifos, propiconazole, oxychlorpyrifos, propiconazole, acetamiprid, isopropanil, propiconazole-sodium, propiconazole-pyrazosulfuron, pendimethalin, bensulfuron-methyl, flusulfuron, pyrazosulfuron-methyl, pyrazosulfuron-ethyl, pyrazosulfuron-methyl, bensulfuron-methyl, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyrimidin, barnsulfuron-methyl, chlorpyrifos pyridafol), pyrazosulfuron, pyrimisulfan, pyrimisulfan-methyl, pyrimisulfan, pyrimisulfan-sodium, pyroxasulfone, pyroxulam, quinclorac acid, chlorpyrifos, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-ethyl, quizalofop-P-ethyl, pyrimisulfuron, pyrimisulfuron-methyl, pyrimisulfuron, pyrimisulfuron-methyl, cyprodinil, cycloribonucleosulfuron, simazine, cyprodinil, S L-261, sulfadiazine, mesotrione, pyrisulfuron, pyrisulfuron-methyl, sulfonylsulfuron, SYN-523, SYP-249 (i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[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-thioimidazolidine-4,5-dione), 2,3-6-TBA, TCA (trifluoroacetic acid), TCA-sodium, Butthiazoline, Terfusarium, Tembotrione, Dexamethasone, Terbufos, Terbufos, Terbufos, Methoxysulfuron, Thiazolamide, Thiazolamide-methyl, Thiphensulfuron-methyl, Thiphensulfuron-methyl, Butanediol, Flupyralid, Tolpyralate, Benzopyrrolidone, Triafamone, Wild valerate, Ether Bensulfuron, triazine, tribenuron-methyl, chlorpyrifos, sulfadiazine, trifludimoxazin, trifludimoxazin-sodium, trifluralin, flusulfanilamide, flusulfanilamide-methyl, triflumethoprim, urea sulfate, metsulfuron-methyl, XDE-848, ZJ-0862 (i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline), and the following compounds:

[0462]

[0463]

[0464] Examples of plant growth regulators that could be potential mixing partners include:

[0465] Acibenzolar, aramazolin-S-methyl, 5-aminolevulinic acid, pyrimidinol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cyproheptadine, 3-(cyclopropion-1-enyl)propionic acid, butyrylhydrazine, dazomet, n-decanol, furfurylic acid, furfurylic acid-sodium, cyproheptadine-dipotassium, cyproheptadine-disodium, and mono(N,N-dimethylalkylammonium), ethephon, flubendiamide, cyproheptadine-butyl, cyproheptadine-butyl, cyproheptadine-pyrimidinol, chlorpyrifos, gibberellic acid, anti-dipamine, indole-3-acetic acid (IAA), 4-indole-3- Butyric acid, isoprothiolane, thiabendazole, jasmonic acid, methyl jasmonicate, maleic hydrazine, growth promoter aqueous solution, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenol salt mixture, 4-oxo-4-[(2-phenylethyl)amino]butyric acid, paclobutrazol, N-phenyl-o-carbamoylbenzoic acid, cyclohexanoic acid, cyclohexanoic acid-calcium, prohydrojasmone, salicylic acid, unicornuate, tetraoxonitrobenzene, phenylthiazolidinyl urea, triacontanol, anti-rebound ester, anti-rebound ester-ethyl, tsitodef, uniconazole, uniconazole-P.

[0466] Combination partners for compounds of general formula (I) according to the present invention also include, for example, the following safeners:

[0467] S1) Compounds from the group consisting of heterocyclic carboxylic acid derivatives:

[0468] S1 a Dichlorophenylpyrazoline-3-carboxylic acid compounds (S1) a Preferred compounds include, for example

[0469] 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-carboxylic acid (S1-1) (“pyrazoline”), and related compounds as described in WO-A-91 / 07874;

[0470] S1 b )Derivatives of dichlorophenylpyrazole carboxylic acid (S1) b Preferred compounds include ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4), and related compounds as described in EP-A-333 131 and EP-A-269 806;

[0471] S1 c )1,5-Diphenylpyrazole-3-carboxylic acid derivatives (S1 c Preferred compounds include ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6), and related compounds as described, for example, in EP-A-268 554;

[0472] S1 d Triazole carboxylic acid compounds (S1) d Preferred compounds include ethyl oxazolium (ethyl ester), namely ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate (S1-7), and related compounds as described in EP-A-174 562 and EP-A-346 620;

[0473] S1 eCompounds of the type 5-benzyl- or 5-phenyl-2-isooxazoline-3-carboxylic acid or 5,5-diphenyl-2-isooxazoline-3-carboxylic acid (S1e), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isooxazoline-3-carboxylic acid (S1-8) or ethyl 5-phenyl-2-isooxazoline-3-carboxylic acid (S1-9) and related compounds as described in WO-A-91 / 08202, or 5,5- Diphenyl-2-isooxazoline carboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isooxazoline-3-carboxylate (S1-11) (“Diphenyloxazoline-ethyl”) or n-propyl 5,5-diphenyl-2-isooxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isooxazoline-3-carboxylate (S1-13), as described in patent application WO-A-95 / 07897.

[0474] S2) Compounds from the group consisting of 8-quinolinoxy derivatives (S2):

[0475] S2 a )8-Quinolinoxyacetic acid compounds (S2) a Preferred are (5-chloro-8-quinolinoxy)acetic acid 1-methylhexyl ester (“Jiecaoquin”) (S2-1), (5-chloro-8-quinolinoxy)acetic acid 1,3-dimethyl-butyl-1-yl ester (S2-2), (5-chloro-8-quinolinoxy)acetic acid 4-allyloxybutyl ester (S2-3), (5-chloro-8-quinolinoxy)acetic acid 1-allyloxy-propyl-2-yl ester (S2-4), and (5-chloro-8-quinolinoxy)acetic acid... Ethyl acetate (S2-5), methyl 5-chloro-8-quinolinoxy acetate (S2-6), allyl (5-chloro-8-quinolinoxy)acetate (S2-7), 2-(2-propyliminooxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxopropyl-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9), and related compounds such as EP-A-86750 and EP-A-94. As described in 349 and EP-A-191 736 or EP-A-0 492 366, and also (5-chloro-8-quinolinoxy)acetic acid (S2-10), its hydrates and salts, such as its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as described in WO-A-2002 / 34048;

[0476] S2 b (5-Chloro-8-quinolinoxy)malonic acid compounds (S2) bPreferred compounds include diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate, and related compounds as described in EP-A-0 582 198.

[0477] S3) Dichloroacetamide active ingredient (S3) is often used as a pre-emergence safener (soil activator safener), for example...

[0478] "Dichloropropenamide (N,N-diallyl-2,2-dichloroacetamide) (S3-1);

[0479] “R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2) is from Stauffer Company;

[0480] “R-28725” (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (S3-3) is from Stauffer Company;

[0481] "benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4);

[0482] “PPG-1292” (N-allyl-N-[(1,3-dioxolane-2-yl)methyl]dichloroacetamide) (S3-5) is from PPG Industries.

[0483] “DKA-24” (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6) is from Sagro-Chem.

[0484] “AD-67” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4,5]decane) (S3-7) is from Nitrokemia or Monsanto.

[0485] “TI-35” (1-Dichloroacetylazineheptanane) (S3-8) is from TRI-Chemical RT.

[0486] "Diclonon" (dicyclonone), "BAS145138", or "LAB145138" (S3-9)

[0487] ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one), from BASF;

[0488] "furilazole" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (S3-10); and its (R) isomer (S3-11).

[0489] S4) Compounds from the acylsulfonamide class (S4):

[0490] S4 a Formula (S) 4a N-acylsulfonamides and their salts, as described in WO-A-97 / 45016,

[0491]

[0492] in

[0493] R A 1 It is (C1-C6)alkyl, (C3-C6)cycloalkyl, wherein the latter two groups are derived from the following v A Substituent substitution: halogen, (C1-C4)alkoxy, (C1-C6)haloalkoxy and (C1-C4) alkylthio, and in the case of cyclic groups, also substituted by (C1-C4)alkyl and (C1-C4)haloalkyl.

[0494] R A 2 It is a halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3;

[0495] m A It is 1 or 2;

[0496] v A It is 0, 1, 2, or 3;

[0497] S4 b ) formula (S4 b Compounds of the 4-(benzoylaminosulfonyl)benzamide type and their salts, as described in WO-A-99 / 16744,

[0498]

[0499] in

[0500] R B 1 ,R B 2 Each is independently hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C3-C6)alkenyl, or (C3-C6)ynyl.

[0501] RB 3 It is a halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, or (C1-C4)alkoxy and

[0502] m B It is 1 or 2.

[0503] For example, the following, among which

[0504] R B 1 =Cyclopropyl, R B 2 = Hydrogen and (R) B 3 ) = 2-OMe(“cyclopropanesulfonamide”, S4-1),

[0505] R B 1 =Cyclopropyl, R B 2 = Hydrogen and (R) B 3 )=5-Cl-2-OMe(S4-2),

[0506] R B 1 =Ethyl, R B 2 = Hydrogen and (R) B 3 ) = 2 - OMe(S4-3),

[0507] R B 1 =Isopropyl, R B 2 = Hydrogen and (R) B 3 )=5-Cl-2-OMe(S4-4) and

[0508] R B 1 =Isopropyl, R B 2 = Hydrogen and (R) B 3 ) = 2 - OMe(S4-5);

[0509] S4 c ) formula (S4 c Compounds of the benzoylaminosulfonylphenylurea class, such as those described in EP-A-365484,

[0510]

[0511] in

[0512] R C 1 ,R C 2 Each is independently hydrogen, (C1-C8)alkyl, (C3-C8)cycloalkyl, (C3-C6)alkenyl, or (C3-C6)ynyl.

[0513] R C 3 It is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3 and

[0514] m C It is 1 or 2;

[0515] For example

[0516] 1-[4-(N-2-methoxybenzoylaminosulfonyl)phenyl]-3-methylurea,

[0517] 1-[4-(N-2-methoxybenzoylaminosulfonyl)phenyl]-3,3-dimethylurea

[0518] 1-[4-(N-4,5-dimethylbenzoylaminosulfonyl)phenyl]-3-methylurea;

[0519] S4 d ) formula (S4 d Compounds of the type N-phenylsulfonyl terephthalamide and their salts, such as those known from CN101838227,

[0520]

[0521] in

[0522] R D 4 It is a halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3;

[0523] m D It is 1 or 2;

[0524] R D 5 It is hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C2-C6)ynyl, and (C5-C6)cycloalkenyl.

[0525] S5) Active ingredients derived from the hydroxy aromatic compounds and aromatic-aliphatic carboxylic acid derivatives classes, such as

[0526] Ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, and WO-A-2005 / 016001.

[0527] S6) Active ingredients (S6) from the 1,2-dihydroquinoxaline-2-one class, such as

[0528] 1-Methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005 / 112630.

[0529] S7) Compounds derived from the diphenylmethoxyacetic acid derivative class (S7), such as methyl diphenylmethoxyacetate (CAS Registry No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid as described in WO-A-98 / 38856.

[0530] Compounds of formula (S8) or salts thereof, as described in WO-A-98 / 27049,

[0531]

[0532] The symbols and exponents are defined as follows:

[0533] R D 1 It is a halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy.

[0534] R D 2 It is hydrogen or (C1-C4) alkyl.

[0535] R D 3 It is hydrogen, (C1-C8)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, or aryl, wherein each of the above carbon-containing groups is unsubstituted or substituted by one or more, preferably up to three identical or different groups from the group consisting of halogens and alkoxy groups;

[0536] n DIt is an integer from 0 to 2.

[0537] S9) refers to active ingredients from the 3-(5-tetrazolylcarbonyl)-2-quinolone class, such as...

[0538] 1,2-Dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Registry No.: 219479-18-2) and 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Registry No.: 95855-00-8), as described in WO-A-1999 / 000020.

[0539] S10) formula (S10) a ) or (S10 b ) compounds

[0540] As described in WO-A-2007 / 023719 and WO-A-2007 / 023764,

[0541]

[0542] in

[0543] R E 1 It is halogen, (C1-C4)alkyl, methoxy, nitro, cyano, CF3, OCF3

[0544] Y E Z E Each can be either O or S independently.

[0545] n E It is an integer between 0 and 4.

[0546] R E 2 It is (C1-C) 16 alkyl, (C2-C6)alkenyl, (C3-C6)cycloalkyl, aryl; benzyl, chlorobenzyl,

[0547] R E 3 It is hydrogen or (C1-C6) alkyl.

[0548] S11) is an active ingredient of the oxyimino compound type, known as a seed dressing agent, for example...

[0549] "Z-1,3-dioxolane-2-ylmethoxyimino(phenyl)acetonitrile" (S11-1) is known as a seed treatment safener for millet / sorghum against metolachlor damage.

[0550] Fluroxypyr (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethyl-O-(1,3-dioxolane-2-ylmethyl)oxime) (S11-2), is known as a seed treatment safener for millet / sorghum against metolachlor damage, and

[0551] "Metolachlor" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3) is known as a seed dressing safer for millet / sorghum against metolachlor damage.

[0552] S12) Active ingredients from the isothiobenzodihydropyranone class, such as [(3-oxo-1H-2-benzothiaran-4(3H)-ylidene)methoxy]methyl acetate (CAS Registry No. 205121-04-6)(S12-1) and related compounds from WO-A-1998 / 13361.

[0553] S13) One or more compounds from group (S13):

[0554] "Naphthalene anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1) is known as a seed-treating safener for corn against damage from thiocarbamate herbicides.

[0555] "4,6-Dichloro-2-phenylpyrimidine" (S13-2) is known as a safener for propachlor in rice cultivation.

[0556] "Metolachlor" (2-chloro-4-trifluoromethyl-1,3-thiazolyl-5-carboxylate benzyl ester) (S13-3) is known as a seed treatment safener for millet / sorghum against damage from metolachlor and isopropylate.

[0557] “CL304415” (CAS Registration No. 31541-57-8)

[0558] (4-Carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid is known as a safe agent for corn against imidazolinone damage.

[0559] "MG 191" (CAS Registry No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia is known as a corn safener.

[0560] “MG 838” (CAS registration number 133993-74-5),

[0561] From Nitrokemia (1-oxa-4-azaspiro[4.5]decane-4-dithiocarboxylic acid 2-propenyl ester) (S13-6),

[0562] "Ethyl phorate" (S-2-ethylthioethyl dithiophosphate O,O-diethyl ester) (S13-7)

[0563] "Dietholate" (O-phenyl thiophosphate O,O-diethyl ester) (S13-8)

[0564] “mephenate” (4-chlorophenyl methylcarbamate) (S13-9).

[0565] S14) Active ingredient, in addition to its herbicidal effect against harmful plants, also acts as a safener for crops (such as rice), for example...

[0566] "Peptochlor" or "MY-93" (1-phenylethylpiperidine-1-thiocarboxylic acid S-1-methyl ester) is known as a safe agent for rice against damage caused by the herbicide glyphosate.

[0567] "Karazuron" or "SK23" (1-(1-methyl-1-phenylethyl)-3-p-tolylureuron) is known as a safe agent for rice against damage caused by the herbicide pyrazosulfuron.

[0568] "Benzalkonium chloride" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), is known as a safener for rice against some herbicides that can damage it.

[0569] Methoxyphenon, or NK 049 (3,3'-dimethyl-4-methoxybenzophenone), is known as a safener for rice against some herbicides that can damage it.

[0570] "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai (CAS Registry No. 54091-06-4) is known as a safe agent for rice against some herbicides that can cause damage.

[0571] Compounds of formula (S15) or their tautomers

[0572]

[0573] As described in WO-A-2008 / 131861 and WO-A-2008 / 131860,

[0574] in

[0575] RH 1 It is a (C1-C6) haloalkyl and

[0576] R H 2 It is hydrogen or halogen and

[0577] R H 3 ,R H 4 Each independently is hydrogen, (C1-C) 16 )alkyl, (C2-C 16 )alkenyl or (C2-C 16 ) ynyl group,

[0578] Each of the last three groups is either unsubstituted or substituted with one or more of the following groups: 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, (C3-C6)cycloalkyl (which is unsubstituted or substituted), phenyl (which is unsubstituted or substituted), and heterocyclic (which is unsubstituted or substituted).

[0579] Or (C3-C6)cycloalkyl, (C4-C6)cycloalkenyl, (C3-C6)cycloalkyl (fused to a 4- to 6-membered saturated or unsaturated carbon ring on one side of the ring), or (C4-C6)-cycloalkenyl (fused to a 4- to 6-membered saturated or unsaturated carbon ring on one side of the ring),

[0580] Each of the last four groups is either unsubstituted or substituted with one or more of the following groups: halogen, hydroxyl, cyano, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylamino, di[(C1-C4)alkyl]amino, [(C1-C4)alkoxy]carbonyl, [(C1-C4)haloalkoxy]carbonyl, (C3-C6)cycloalkyl (which is unsubstituted or substituted), phenyl (which is unsubstituted or substituted), and heterocyclic (which is unsubstituted or substituted).

[0581] or

[0582] R H 3 It is (C1-C4)alkoxy, (C2-C4)alkenyloxy, (C2-C6)alkynyloxy, or (C2-C4)haloalkoxy and

[0583] R H4 It is hydrogen or (C1-C4)-alkyl or

[0584] R H 3 and R H 4 Together with the directly bonded nitrogen atom, it is a four- to eight-membered heterocycle, and the O,O-diethyl ring may contain additional cyclic heteroatoms in addition to the nitrogen atom, preferably up to two additional cyclic heteroatoms (from the group consisting of N, O and S), and is unsubstituted or substituted by one or more of the following groups: halogen, cyano, nitro, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4) alkylthio.

[0585] S16) is an active ingredient primarily used as a herbicide but also acting as a safener for crops, for example...

[0586] (2,4-Dichlorophenoxy)acetic acid (2,4-D),

[0587] (4-Chlorophenoxy)acetic acid,

[0588] (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (2-methyl-4-chloropropionic acid (mecoprop)),

[0589] 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),

[0590] (4-Chloro-o-tolyloxy)acetic acid (MCPA),

[0591] 4-(4-chloro-o-tolyloxy)butyric acid,

[0592] 4-(4-Chlorophenoxy)butyric acid,

[0593] 3,6-Dichloro-2-methoxybenzoic acid (dicamba),

[0594] 3,6-Dichloro-2-methoxybenzoic acid 1-(ethoxycarbonyl)ethyl ester (inner iminoyl dichloro-ethyl).

[0595] Preferred safeners in combination with compounds of formula (I) and / or their salts, especially with compounds of formulas (I.1) to (I.34) and / or their salts, are: cyclopropanesulfonamide, oxazol-ethyl ester, bis(oxazolyl) ethyl ester, pyrazole-oxazolyl diethyl ester, oxazolyl sulfadiazine, benzalkonium chloride, S4-1 and S4-5, and particularly preferred safeners are: cyclopropanesulfonamide, bis(oxazolyl) ethyl ester, and pyrazole-oxazolyl diethyl ester.

[0596] Biological Example:

[0597] A. Post-emergence weed control and crop-plant compatibility

[0598] Seeds of monocotyledonous and dicotyledonous weeds and crops were placed in sandy soil in plastic or wood fiber pots, covered with soil, and cultivated in a greenhouse under controlled growth conditions. Two to three weeks after sowing, test plants were treated at the one-leaf stage. The compounds of the invention were formulated as wettable powders (WP) or emulsion concentrates (EC), and then sprayed as an aqueous suspension or emulsion onto the green parts of the plants at a water application rate of 600 l / ha (equivalent value), with the addition of 0.5% additive. After approximately three weeks of placing the test plants in a greenhouse under optimal growth conditions, the activity of the formulation was visually assessed compared to an untreated control group. For example, 100% activity = plant death, 0% activity = similar to control plants.

[0599] Tables A1 to A14 below show the effects of selected compounds of general formula (I) according to Tables I.1 to I.33 on various harmful plants at application rates of 20 g / ha or less, the effects obtained by the experimental methods described above. Appendices (labels) “a”, “b” and “c” distinguish the dosages used (for harmful plants tested equivalently in other respects).

[0600] Table A1a: Postemergence effect of 1.25 g / ha on ABUTH (in %)

[0601]

[0602]

[0603] Table A1b: Postemergence effect of 5 g / ha on ABUTH (in %)

[0604]

[0605]

[0606] Table A1c: Postemergence effect of 20 g / ha on ABUTH (in %)

[0607]

[0608]

[0609] Table A2a: Postemergence effect of 1.25 g / ha on ALOMY (in %)

[0610]

[0611] Table A2b: Postemergence effect of 5 g / ha on ALOMY (in %)

[0612]

[0613]

[0614] Table A2c: Postemergence effect of 20 g / ha on ALOMY (in %)

[0615]

[0616]

[0617]

[0618] Table A3a: Postemergence effect of 1.25 g / ha on AMARE (in %)

[0619]

[0620]

[0621] Table A3b: Postemergence effect of 5 g / ha on AMARE (in %)

[0622]

[0623]

[0624]

[0625] Table A3c: Post-emergence effect of 20 g / ha on AMARE (in %)

[0626]

[0627]

[0628] Table A4a: Postemergence effect of AVEFA at a concentration of 5 g / ha (in %)

[0629]

[0630] Table A4b: Postemergence effect of 20 g / ha on AVEFA (in %)

[0631]

[0632]

[0633] Table A5a: Postemergence effect of ECHCG at 1.25 g / ha (in %)

[0634]

[0635] Table A5b: Postemergence effect of ECHCG at 5 g / ha (in %)

[0636]

[0637]

[0638] Table A5c: Postemergence effect of ECHCG at 20 g / ha (in %)

[0639]

[0640]

[0641] Table A6a: Postemergence effect of 5 g / ha on LOLRI (in %)

[0642]

[0643] Table A6b: Postemergence effect of 20 g / ha on LOLRI (in %)

[0644]

[0645] Table A7a: Postemergence effect of MATIN at 1.25 g / ha (in %)

[0646]

[0647]

[0648] Table A7b: Postemergence effect of MATIN at a concentration of 5 g / ha (in %)

[0649]

[0650]

[0651] Table A7c: Postemergence effect of MATIN at 20 g / ha (in %)

[0652]

[0653]

[0654] Table A8a: Postemergence effect of 1.25 g / ha on PHBPU (in %)

[0655]

[0656]

[0657] Table A8b: Post-emergence effect of 5 g / ha on PHBPU (in %)

[0658]

[0659]

[0660] Table A8c: Post-emergence effect of 20 g / ha on PHBPU (in %)

[0661]

[0662]

[0663]

[0664] Table 9a: Postemergence effect of 1.25 g / ha on POLCO (in %)

[0665]

[0666] Table A9b: Postemergence effect of 5 g / ha on POLCO (in %)

[0667]

[0668]

[0669]

[0670] Table A9c: Postemergence effect of 20 g / ha on POLCO (in %)

[0671]

[0672]

[0673] Table A10a: Postemergence effect of SETVI at 125 g / ha (in %)

[0674]

[0675]

[0676]

[0677] Table A10b: Postemergence effect of SETVI at 5 g / ha (in %)

[0678]

[0679]

[0680] Table A10c: Postemergence effect of SETVI at a concentration of 20 g / ha (in %)

[0681]

[0682]

[0683] Table A11a: Post-emergence effect of VERPE at a concentration of 1.25 g / ha (in %)

[0684]

[0685]

[0686] Table A11b: Post-emergence effect of VERPE at a concentration of 5 g / ha (in %)

[0687]

[0688]

[0689] Table A11c: Post-emergence effect of 20 g / ha on VERPE (in %)

[0690]

[0691]

[0692]

[0693] Table A12a: Postemergence effect of VIOTR at 1.25 g / ha (in %)

[0694]

[0695]

[0696] Table A12b: Postemergence effect of VIOTR at 5 g / ha (in %)

[0697]

[0698]

[0699] Table A12c: Post-emergence effect of 20 g / ha on VIOTR (in %)

[0700]

[0701]

[0702]

[0703] Table A13a: Post-emergence effect of 5 g / ha on HORMU (in %)

[0704]

[0705] Table A13b: Post-emergence effect of 20 g / ha on HORMU (in %)

[0706]

[0707] Table A14a: Postemergence effect of 1.25 g / ha on STEME (in %)

[0708]

[0709] Table A14b: Postemergence effect of 5 g / ha on STEME (in %)

[0710]

[0711] Table A14c: Postemergence effect of 20 g / ha on STEME (in %)

[0712]

[0713] Tables A15 to A19 below show the crop plant compatibility of selected compounds of general formula (I) according to Tables I.1 to I.33 at application rates corresponding to 5 g / ha or lower, as observed in the experiments using the methods described above. Here, the observed effects on the selected crop plants (values ​​in %) are given compared to the untreated control group. Labels “a”, “b”, and “c” distinguish the dosage used (for crops tested equivalently in other respects).

[0714] Table A15a: Postemergence effect of 1.25 g / ha on BRSNW (in %)

[0715]

[0716] Table A15b: Postemergence effect of 5 g / ha on BRSNW (in %)

[0717]

[0718] Table A15c: Postemergence effect of 20 g / ha on BRSNW (in %)

[0719]

[0720] Table A16a: Postemergence effect of 1.25 g / ha on ZEAMX (in %)

[0721]

[0722]

[0723] Table A16b: Post-emergence effect of 5 g / ha on ZEAMX (in %)

[0724]

[0725]

[0726] Table A16c: Post-emergence effect of 20 g / ha on ZEAMX (in %)

[0727]

[0728] Table A17a: Postemergence effect of 1.25 g / ha on TRZAS (in %)

[0729]

[0730]

[0731] Table A17b: Postemergence effect of 5 g / ha on TRZAS (in %)

[0732]

[0733]

[0734]

[0735] Table A17c: Postemergence effect of 20 g / ha on TRZAS (in %)

[0736]

[0737] Table A18a: Postemergence effect of 1.25 g / ha on ORYSA (in %)

[0738]

[0739]

[0740]

[0741] Table A18b: Postemergence effect of 5 g / ha on ORYSA (in %)

[0742]

[0743]

[0744] Table A18c: Postemergence effect of 20 g / ha on ORYSA (in %)

[0745]

[0746] Table A19a: Postemergence effect of 1.25 g / ha on GLXMA (in %)

[0747]

[0748] Table A19b: Post-emergence effect of 5 g / ha on GLXMA (in %)

[0749]

[0750] Table A19c: Post-emergence effect of 20 g / ha on GLXMA (in %)

[0751]

[0752]

[0753] As the results show, the compounds of general formula (I) according to the present invention exhibit good herbicidal effects against harmful plants (e.g., Abutilon theophrasti, Alomy, Amaranth, Avefa, Ecclesia asiatica, Hormu, Lorri, Matin, Phoebe pilosa, Polygonum aviculare, Setvi, Stellaria media, Veronica persica, and Viotr) at an application rate of 0.02 kg or less per hectare, and good crop plant compatibility with organisms (e.g., rice, maize, brassica rapa, soybean, and wheat) at an application rate of 0.02 kg or less per hectare.

[0754] B. Pre-emergence weed control and crop-plant compatibility

[0755] Seeds of monocotyledonous and dicotyledonous weeds and crops were placed in plastic or organic planting pots and covered with soil. The compound according to the invention, formulated as a wettable powder (WP) or emulsion concentrate (EC), was then applied to the surface of the covered soil as an aqueous suspension or emulsion with 0.5% additive added, at a water application rate equivalent to 600 l / ha (equivalent). After treatment, the pots were placed in a greenhouse and maintained under good growing conditions for the test plants. After approximately 3 weeks, the effectiveness of the formulation was visually rated (in percentage) compared to an untreated control group. For example, 100% activity = plant death, 0% activity = similar to control plants.

[0756] Tables B1 to B10 below show the effects of selected compounds of general formula (I) according to Tables I.1 to I.33 on various harmful plants at application rates of 80 g / ha or less, the effects obtained by the experimental methods described above. Labels “a”, “b”, and “c” distinguish the dosage used (for harmful plants tested equivalently in other respects).

[0757] Table B1a: Pre-emergence effect of 20 g / ha on ABUTH (in %)

[0758]

[0759] Table B1b: Pre-emergence effect of 80 g / ha on ABUTH (in %)

[0760]

[0761] Table B2a: Pre-emergence effect of 20 g / ha on ALOMY (in %)

[0762]

[0763] Table B2b: Pre-emergence effect of 80 g / ha on ALOMY (in %)

[0764]

[0765] Table B3a: Pre-emergence effect of 20 g / ha on AMARE (in %)

[0766]

[0767] Table B3b: Pre-emergence effect of 80 g / ha on AMARE (in %)

[0768]

[0769] Table B4: Pre-emergence effect of 80 g / ha on AVEFA (in %)

[0770]

[0771] Table B5a: Pre-emergence effect of 20 g / ha on DIGSA (in %)

[0772]

[0773] Table B5b: Pre-emergence effect of 80 g / ha on DIGSA (in %)

[0774]

[0775] Table B6a: Pre-emergence effect of ECHCG at 20 g / ha (in %)

[0776]

[0777] Table B6b: Pre-emergence effect of ECHCG at 80 g / ha (in %)

[0778]

[0779] Table B7a: Pre-emergence effect of 20 g / ha on LOLRI (in %)

[0780]

[0781] Table B7b: Pre-emergence effect of 80 g / ha on LOLRI (in %)

[0782]

[0783] Table B8a: Pre-emergence effect of MATIN at 20 g / ha (in %)

[0784]

[0785] Table B8b: Pre-emergence effect of MATIN at 80 g / ha (in %)

[0786]

[0787] Table B9a: Pre-emergence effect of 20 g / ha on PHBPU (in %)

[0788]

[0789] Table B9b: Pre-emergence effect of 80 g / ha on PHBPU (in %)

[0790]

[0791] Table B10a: Pre-emergence effect of 20 g / ha on VERPE (in %)

[0792]

[0793] Table B10b: Pre-emergence effect of 80 g / ha on VERPE (in %)

[0794]

[0795] Tables B11 to B12 below show the crop plant compatibility of selected compounds of general formula (I) according to Tables I.1 to I.33 at application rates corresponding to 80 g / ha or lower, which were observed in the experiments using the methods described above. Here, the observed effects on the selected crop plants (values ​​in %) are reported compared with the untreated control group.

[0796] Table B11: Pre-emergence effect of 20 g / ha on ZEAMX (in %)

[0797]

[0798] Table B12: Pre-emergence effect of 20 g / ha on GLXMA (in %)

[0799]

[0800] As the results show, the compounds of general formula (I) according to the present invention exhibit good herbicidal activity against harmful plants (e.g., Abutilon theophrasti, Alomy, Amaranth, Avefa, Digitaria, Ecclesia asiatica, Lorraine serrata, Matin, Phoebe pilosa, and Veronica persica) at an application rate of 0.08 kg or less of active substance per hectare in pre-emergence treatment, and good compatibility with organisms (e.g., Zeamyces maize and Glycine soy) at an application rate of 0.02 kg per hectare.

[0801] C. Comparison of the herbicidal activity and crop compatibility of two compounds according to the invention (I.7-1 and I.7-115) with known structure-related compounds in the literature (WO2002 / 098227, a-17 and EP1106607, 3-14) in post-emergence treatment.

[0802] Tables C1-C4 below show the effects of two compounds according to the invention (I.7-1 and I.7-115) and structurally related compounds known in the literature (a-17 in WO2002 / 098227 and 3-14 in EP1106607) on various harmful plants obtained by the above-described experimental methods at application rates corresponding to 5 g / ha and below.

[0803] Here, under the same ester functionality (functional group) and "chain length", the two compounds according to the invention (I.7-1 and I.7-115) are distinguished from known compounds in the literature by significant structural features in terms of the ester unit, either by introducing heteroatoms or by introducing heteroatoms during ring formation.

[0804] Table C1

[0805]

[0806] Table C2

[0807]

[0808] Table C3

[0809]

[0810] Table C4

[0811]

[0812] As shown in Tables C1 to C4, compounds I.7-1 and I.7-115, according to the invention, exhibit significantly improved herbicidal activity against harmful plants (e.g., Alomy, ECHCG, MATIN, and SETVI) at application rates of 5 g per hectare or less, compared to compounds a-17 (WO2002 / 098227) or 3-14 (EP1106607) known in the literature.

[0813] Table C5 below shows the effects of the two compounds according to the invention (I.7-1 and I.7-115) and the structure-related compounds known in the literature (a-17 in WO2002 / 098227 and 3-14 in EP1106607) on the crop plant rice (ORYSA) obtained by the above experimental method at an application rate corresponding to 1.25 g / ha.

[0814] Table C5

[0815]

[0816] As shown in Table C5, compounds I.7-1 and I.7-115, according to the invention, exhibit significantly improved compatibility with the crop plant rice (ORYSA) at an application rate of 1.25 g per hectare, compared with known compounds a-17 (WO2002 / 098227) or 3-14 (EP1106607) in the literature.

Claims

1. Substituted N-phenyluracil of general formula (I) or a salt thereof (I) in R 1 It is hydrogen. R 2 It is fluorine. R 3 It is fluorine. R 4 It consists of chlorine, bromine, cyano, and NO2. R 5 It is hydrogen and fluorine. R 6 It has hydrogen, fluorine, bromine, and cyano groups. R 7 It is hydrogen. G stands for methylene or (methyl)methylene. X is O (oxygen) or S (sulfur). Y stands for O (oxygen). and Q is one of the specified parts of Q-41 and Q-291.

2. Use of one or more compounds of general formula (I) as defined in claim 1 and / or their salts as herbicides and / or plant growth regulators.

3. The use as defined in claim 2, which is used in crops of useful plants and / or ornamental plants.

4. A weed-controlling and / or plant growth-regulating composition, characterized in that... The composition comprises one or more compounds of general formula (I) as defined in claim 1 and / or salts thereof, and one or more additional substances selected from group (i) and / or (ii), wherein (i) one or more other agriculturally active chemical substances, selected from insecticides, acaricides, nematicides, other herbicides, fungicides, safeners, fertilizers and / or other growth regulators, (ii) One or more formulation adjuvants commonly used in plant protection.

5. A method for controlling harmful plants or regulating plant growth, characterized in that... effective amount - One or more compounds of general formula (I) as defined in claim 1 and / or salts thereof, or -The composition according to claim 4 Apply to plants, plant seeds, soil in which or on which plants grow, or cultivation areas.

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