EA042989B1 - SUBSTITUTED THIOPHENILURACIDES, THEIR SALTS AND THEIR USE AS HERBICIDES - Google Patents

Description

The present invention relates to the field of crop protection products, in particular herbicides for the selective control of weeds and weeds in agricultural crops of useful plants.

Specifically, the present invention relates to substituted thiophenyluracils and their salts, to processes for their preparation and to their use as herbicides, in particular for the control of weeds and/or weeds in agricultural crops of useful plants, and/or as plant growth regulators to influence on the growth of agricultural crops of useful plants.

Currently known crop protection products for the selective control of harmful plants in crops of useful plants or active ingredients for controlling the growth of unwanted plants have some disadvantages in their use, which is that either they (a) do not have a herbicidal effect in specific pests, or are otherwise insufficient, or (b) have too little spectrum of pests that can be controlled by the active ingredient, or (c) have too little selectivity in crops of beneficial plants, and/or (d) have undesirable profile in terms of toxicology. In addition, some active ingredients that can be used as plant growth regulators for some useful plants lead to an undesirable reduction in yield of other useful plants, or they are compatible with the cultivated plant only within a narrow range of application rates, if at all. . Some of the known active ingredients cannot be produced economically on an industrial scale due to the difficulty in obtaining precursors and reagents, or they have only insufficient chemical stability. For other active ingredients, the effect is also highly dependent on environmental conditions such as weather and soil conditions.

There remains a need to improve the herbicidal action of such known compounds, especially at low application rates, and their compatibility with crop plants.

It is known from various documents that specific substituted N-aryluracils can be used as active herbicidal ingredients (see EP 408382, EP 473551, EP 648749, US 4943309, US 5084084, US 5127935, WO 91/00278, WO 95/29168, WO 95/30661, WO 96/35679, WO 97/01541, WO 98/25909, WO 1801/39597). However, many known aryluracils have a number of disadvantages in their action, in particular in relation to monocotyledonous weeds. A number of combinations of active herbicidal ingredients based on N-aryluracils have similarly become known (see DE 4437197, EP 714602, WO 96/07323, WO 96/08151, JP 11189506). However, the properties of such combinations of active ingredients were also not satisfactory in all aspects.

However, it is known that specific N-aryluracils, optionally containing additionally substituted lactic acid groups, can also be used as active herbicidal ingredients (see JP 1800/302764, JP 1801/172265, US 6403534, EP 408382). Additionally, it is known that N-aryluracils, optionally containing additionally substituted thiolactic acid groups, similarly exhibit herbicidal effects (see WO 2010/038953, KR 2011110420).

Substituted thiophenyluracils, optionally containing additionally substituted thioacetic acid ester groups, in contrast, have not yet been described per se. In this work, it was unexpectedly found that specific substituted thiophenyluracils or their salts have good suitability as herbicides and can be used especially advantageously as active ingredients for the control of monocots and dicotyledonous weeds in agricultural crops of useful plants.

Thus, the present invention provides substituted thiophenyluracils of general formula (I) or their salts

in which

R ¹ is (C1-C ₈ )alkyl,

R ² is hydrogen, (C1-C ₈ )alkyl,

R ³ is halogen,

R ⁴ is halogen,

R ⁵ and R ⁶ independently represent hydrogen, halogen, (C1-C ₈ )alkyl, (C ₃ -C ₈ )cycloalkyl, (C ₃ C ₈ )cycloalkyl-(C1-C ₈ )alkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, (C 1 -C ₁₀ ) haloalkyl, (C ₂ -C ₈ ) haloalkenyl, (C ₂ -C ₈ ) haloalkynyl, (C ₃ -C ₁₀ ) halocycloalkyl, (C ₄ -C ₁₀ ) cycloalkenyl, (C ₄ -C ₁₀ ) halocycloalkenyl, (C1-C ₈ )alkoxy, (C1-C ₈ )alkoxy-(C1-C ₈ )alkyl, (C1-C ₈ )alkoxy-(C1 -C ₈ ) haloalkyl, (C1C ₈ ) haloalkoxy-(C ₁ -C ₈ ) haloalkyl, (C ₁ -C ₈ ) haloalkoxy-(C ₁ -C ₈ ) alkyl, aryl, aryl-(C ₁ -C ₈ ) alkyl, heteroaryl, heteroaryl-(C1-C ₈ )alkyl _, (C ₄ -C ₁₀ )cycloalkenyl-(C1-C ₈ )alkyl, heterocyclyl, _heterocyclyl )alkylthio-(C1-C ₈ )alkyl, (C1-C ₈ )haloalkylthio-(C1-C ₈ )alkyl, (C1-C ₈ )alkylcarbonyl-(C1-C ₈ )-alkyl, C(O)OR ¹⁷ , C(O)NR ¹⁵ R ¹⁶ , C(O)R ¹⁷ , R ¹⁷ O(O)C-(C1-C8)alkyl, R ¹⁵ R ¹⁶ N(O)C-(CiC8)alkyl, R ¹⁵ R ¹⁶ N-(C1-C ₈ )alkyl, or

R ⁵ and R ⁶ together with the carbon atom to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring, m is 0, p is 0, 1, 2, 3, 4, 5,

X is O (oxygen) or NR ¹¹ or NOR ¹² moieties, and R ¹¹ and R ¹² in NR ¹¹ and NOR ¹² moieties are independently defined as defined below,

R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are independently hydrogen, fluorine, (C1-C8) alkyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl-(C1-C8) alkyl, (C2-C8 )alkenyl, (C2-C8) alkynyl, (C1-C10) haloalkyl, (C2-C8) haloalkenyl, (C2-C8) haloalkynyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4-C10) halocycloalkenyl, (C1-C8) alkoxy-(C1-C8) haloalkyl, (C1-C8) haloalkoxy-(C1-C8) haloalkyl, aryl, aryl-(C1-C8) alkyl, heteroaryl, heteroaryl-(C1-C8) alkyl, (C4-C10) cycloalkenyl-(C1-C8) alkyl, heterocyclyl, heterocyclyl-(C1-C8) alkyl, R ¹⁷ O-(C1-C ₈ )alkyl, R ¹⁸ S-(C1-C8) alkyl, (C1-C8) alkylcarbonyl-(C1C8) alkyl, C(O)OR ¹⁷ , C(O)NR ¹⁵ R ¹⁶ , C(O)R ¹⁷ , R ¹⁷ O(O)C-(C1-C8) alkyl, R ¹⁵ R ¹⁶ N(O)C-(C1-C8) alkyl, R ¹⁵ R ¹⁶ N(C1-C ₈ ) alkyl, or

R ⁵ and R ⁷ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 8-membered monocyclic or bicyclic ring, or

R ⁷ and R ⁸ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or

R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or

R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form an exomethylene group, or

R ⁷ and R ⁹ together with the carbon atoms to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring,

R ¹¹ is hydrogen, (C1-C ₈ )alkyl, (C ₃ -C ₈ )cycloalkyl, cyano-(C1-C ₈ )alkyl, (C ₃ C ₈ )cycloalkyl-(C ₁ -C ₈ )alkyl, (C ₁ -C ₈ )alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C ₃ -C ₈ )cycloalkylsulfonyl, heterocyclylsulfonyl, aryl-(C ₁ -C ₈ )alkylsulfonyl, (C ₁ -C ₈ )alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C ₃ -C ₈ ) cycloalkylcarbonyl, heterocyclylcarbonyl, (C ₁ -C ₈ ) alkoxycarbonyl, (C ₁ -C ₈ ) alkoxy, (C ₂ -C ₈ ) alkenyloxy, aryl-(C ₁ -C ₈ ) alkoxycarbonyl, (C ₁ -C ₈ ) haloalkylcarbonyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C8) haloalkyl, halogen-(C2-C8) alkynyl, halo(C ₂ -C ₈ ) alkenyl, (C1-C ₈ ) alkoxy-(C1-C ₈ )alkyl, amino, (C1-C ₈ )alkylamino, bis[(C1-C ₈ )alkyl]amino, (C1C8) alkoxy-(C1-C8) alkoxy-(C1-C8 )alkyl, heteroaryl-(C1-C8)alkylsulfonyl, heterocyclyl-(C1-C8)alkylsulfonyl, (C2-C8)alkenyloxycarbonyl, (C2-C8)alkynyloxycarbonyl, (C1-C8)alkylaminocarbonyl, (C3C8)cycloalkylaminocarbonyl, bis-[ (C1-C8)alkyl]aminocarbonyl,

R ¹² is hydrogen, (C1-C8) alkyl, (C3-C8) cycloalkyl-(C1-C8) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C8) alkoxy-(C1-C8 )alkyl, aryl, aryl-(C1-C8)alkyl, R ¹⁷ O(O)C-(C1-C ₈ )alkyl, R ¹⁵ R ¹⁶ N(O)C(C ₁ -C ₈ )alkyl,

R ¹³ is hydrogen, (C1-C8) alkyl, (C1-C8) haloalkyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl-(C1-C8) alkyl, (C2-C8) alkenyl, (C2-C8 ) alkynyl, (C1-C8) alkoxy-(C1-C8) alkyl, (C1-C8) haloalkoxy-(C1-C8) alkyl, aryl, aryl-(C1-C8) alkyl, heteroaryl, heteroaryl-(C1-C8 )alkyl, heterocyclyl, heterocyclyl-(C1-C8)alkyl, (C1-C8)alkylthio-(C1-C8)alkyl, (C1-C8)haloalkylthio-(C1-C8)alkyl, (C1C8)alkylcarbonyl-(C1- C8) alkyl, R ¹⁷ O(O)C-(C1-C ₈ )alkyl, R ¹⁵ R ¹⁶ N(O)C-(C1-C8) alkyl, R ¹⁵ R ¹⁶ N-(c1C8) alkyl, or

R ⁷ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or

R ⁹ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or

R ¹¹ and R ¹³ when X is NR ¹¹ together with the nitrogen atom to which they are attached form a 4-10 membered monocyclic or bicyclic ring which is fully saturated, or

R ¹² and R ¹³ when X is NOR ¹² together with the nitrogen atom to which they are attached form a fully saturated and optionally further substituted 4-10 membered monocyclic or bicyclic ring,

R ¹⁴ is fluorine,

R ¹⁵ and R ¹⁶ are the same or different and are independently hydrogen, (C1C8) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C8) cyanoalkyl, (C1-C10) haloalkyl, (C2C8 ) haloalkenyl, (C2-C8) haloalkynyl, (C3-C10) cycloalkyl, (C3-C10) halocycloalkyl, (C4C10) cycloalkenyl, (C4-C10) halocycloalkenyl, (C1-C8) alkoxy-(C1-C8) alkyl, (C1-C8) haloalkoxy (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkylthio-(C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkylthio-(C ₁ -C ₈ ) alkyl , (C ₁ -C ₈ )alkoxy-(C ₁ C ₈ )haloalkyl, aryl, aryl-(C ₁ -C ₈ )alkyl, heteroaryl, heteroaryl-(C ₁ -C ₈ )alkyl, (C ₃ -C ₈ )cycloalkyl-(С ₁ - 2 042989

C ₈ )alkyl, (C4-C1o) cycloalkenyl-(C ₁ -C ₈ )alkyl, COR ¹⁷ , SO2R ¹⁸ , (C ₁ -C ₈ )-alkyl-HNO ₂ S-, (C ₃ -C ₈ ) cycloalkylHNO2S -, heterocyclyl, (C1-C ₈ )alkoxycarbonyl-(C1-C ₈ )alkyl, (C1-C ₈ )alkoxycarbonyl, aryl-(C1C ₈ )alkoxycarbonyl-(C ₁ -C ₈ )alkyl, aryl-(C ₁ -C ₈ ) alkoxycarbonyl, heteroaryl-(C ₁ -C ₈ ) alkoxycarbonyl, (C ₂ -C ₈ ) alkenyloxycarbonyl, (C ₂ -C ₈ ) alkynyloxycarbonyl, heterocyclyl-(C ₁ -C ₈ ) alkyl,

R ¹⁷ is hydrogen, (C1-C ₈ )alkyl, (C ₂ -C ₈ )alkenyl, (C ₂ -C ₈ )alkynyl, (C1-C ₈ )cyanoalkyl, (C1-C ₁₀ ) haloalkyl, (C ₂ -C ₈ ) haloalkenyl, (C ₂ -C ₈ ) haloalkynyl, (C ₃ -C ₁₀ ) cycloalkyl, (C ₃ C _1o ) halocycloalkyl, (C ₄ -C _1o ) cycloalkenyl, (C ₄ -C _1o ) halocycloalkenyl , (C ₁ -C ₈ )alkoxy-(C ₁ C ₈ )alkyl, (C ₁ -C ₈ )alkoxy-(C ₁ -C ₈ )haloalkyl, aryl, aryl-(C ₁ -C ₈ )alkyl, heteroaryl , heteroaryl-(C ₁ C8) alkyl, (C3-C8) cycloalkyl-(C1-C8) alkyl, (C4-C10) cycloalkenyl-(C1-C8) alkyl, (C1-C8) alkoxycarbonyl (C1-C8) alkyl , (C2-C8) alkenyloxycarbonyl-(C1-C8) alkyl, aryl-(C1-C8) alkoxycarbonyl-(C1-C8) alkyl, hydroxycarbonyl-(C1-C8) alkyl, heterocyclyl, heterocyclyl-(C1-C8) alkyl ,

R ¹⁸ is hydrogen, (C1-C8) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C8) cyanoalkyl, (C1-C10) haloalkyl, (C2-C8) haloalkenyl, (C2 -C8) haloalkynyl, (C3-C10) cycloalkyl, (C3C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4-C10) halocycloalkenyl, (C1-C8) alkoxy-(C1C ₈ ) alkyl, (C ₁ -C ₈ )alkoxy-(C ₁ -C ₈ )haloalkyl, aryl, aryl-(C ₁ -C ₈ )alkyl, heteroaryl, heteroaryl-(C ₁ C ₈ )alkyl, heterocyclyl-(C ₁ -C ₈ )alkyl, (C ₃ -C ₈ )cycloalkyl-(C ₁ -C ₈ )alkyl, (C ₄ -C ₁₀ )cycloalkenyl-(C ₁ C ₈ )alkyl, NR15R ¹⁶ , where aryl means a mono-, bi- or polycyclic aromatic system containing 6-14 ring carbon atoms, heterocyclyl contains at least one heterocyclic ring which is saturated, unsaturated, partially saturated or heteroaromatic and contains 3-9 ring atoms and 1-4 heteroatoms selected from the group consisting of N, O and S, heteroaryl means fully unsaturated aromatic heterocyclic 5-7 membered rings containing 1-4 identical or different heteroatoms selected from O, S or N.

The compounds of general formula (I) can form salts by adding a suitable inorganic or organic acid, for example mineral acids, for example HCl, HBr, H ₂ SO ₄ , H ₃ PO ₄ or HNO ₃ , or organic acids, for example carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, for example p-toluenesulfonic acid, to a basic group, for example amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. In such a case, such salts contain the conjugate base for the acid as an anion. Suitable substituents in deprotonated form, for example sulfonic acids, in particular sulfonamides or carboxylic acids, can form internal salts with groups which in turn are capable of protonation, such as amino groups. Salts can also be formed by attacking the compounds of general formula (I) with a base. Suitable bases are, for example, organic amines such as trialkylamines, morpholine, piperidine and pyridine, and hydroxides, carbonates and hydrogen carbonates of ammonium, alkali metals or alkaline earth metals, in particular sodium hydroxide and potassium hydroxide, sodium carbonate and potassium carbonate and hydrogen carbonate sodium and potassium bicarbonate. Such salts are compounds in which the acidic hydrogen has been replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR ^a R ^b R ^c R ^d ] ⁺ , in which each R ^a -R ^d independently represents an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (Cp C ₄ )-trialkylsulfonium and (C1-C ₄ )-trialkylsulfoxonium salts.

The compounds of formula (I) used in accordance with the present invention and their salts are hereinafter referred to as compounds of general formula (I).

The present invention preferably provides compounds of general formula (I) wherein

R ¹ is (C1-C ₇ )alkyl,

R ² is hydrogen, (C1-C ₇ )alkyl,

R ³ is halogen,

R ⁴ is halogen,

R ⁵ and R ⁶ are independently hydrogen, halogen, (C1-C7)alkyl, (C3-C7)cycloalkyl, (C3C7)cycloalkyl-(C1-C7)alkyl, (C2-C7)alkenyl, (C2-C7) alkynyl, (C1-C10) haloalkyl, (C2-C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4C10) halocycloalkenyl, (C1-C7) alkoxy, ( C1-C7) alkoxy-(C1-C7) alkyl, (C1-C7) alkoxy-(C1-C7) haloalkyl, (C1-C7) haloalkoxy-(C1-C7) haloalkyl, (C1-C7) haloalkoxy-(C1 -C7)alkyl, aryl, aryl(C1-C7)alkyl, heteroaryl, heteroaryl-(C1-C7)alkyl, (C4-C10)cycloalkenyl-(C1-C7)alkyl, heterocyclyl, heterocyclyl-(C1-C7)alkyl , (C1-C7)alkylthio-(C1-C7)alkyl, (C1-C7)haloalkylthio-(C1-C7)alkyl, (C1C7)alkylcarbonyl-(C1-C7)alkyl, C(O)OR ¹⁷ , C( O)NR ¹⁵ R ¹⁶ , C(O)R ¹⁷ , R ¹⁷ O(O)C-(C1-C7)alkyl, R ¹⁵ R ¹⁶ N(O)C(C1-C7)alkyl, R ¹⁵ R ¹⁶ N -(C ₁ -C ₇ )alkyl, or

- 3 042989

R ⁵ and R ⁶ together with the carbon atom to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring, m is 0, p is 0, 1, 2, 3,

X is O (oxygen), N (nitrogen), or NR ¹¹ or NOR ¹² moieties, and R ¹¹ and R ¹² in NR ¹¹ and NOR ¹² moieties independently have the meanings as defined below,

R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are independently hydrogen, fluoro, (C1-C7) alkyl, (C3-C7) cycloalkyl, (C3-C7) cycloalkyl-(C1-C7) alkyl, (C2-C7 )alkenyl, (C2-C7) alkynyl, (C1-C10) haloalkyl, (C2-C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4C10) halocycloalkenyl, (C1-C7) alkoxy-(C1-C7) haloalkyl, (C1-C7) haloalkoxy-(C1-C7) haloalkyl, aryl, aryl-(C1-C7) alkyl, heteroaryl, heteroaryl-(C1-C7) alkyl, (C4-C10) cycloalkenyl-(C1C7) alkyl, heterocyclyl, heterocyclyl-(C1-C7) alkyl, R ¹⁷ O-(C1-C ₇ )alkyl, R ¹⁸ S-(C1-C7) alkyl, (C1C7) alkylcarbonyl -(C1-C7)alkyl, C(O)OR ¹⁷ , C(O)NR ¹⁵ R ¹⁶ , C(O)R ¹⁷ , R ¹⁷ O(O)C-(C1-C7) alkyl, R ¹⁵ R ¹⁶ N(O)C(C1-C7)alkyl, R ¹⁵ R ¹⁶ N-(C ₁ -C ₇ )alkyl, or

R ⁵ and R ⁷ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 8-membered monocyclic or bicyclic ring, or

R ⁷ and R ⁸ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or

R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or

R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form an exomethylene group, or

R ⁷ and R ⁹ together with the carbon atoms to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring,

R ¹¹ is hydrogen, (C1-C ₇ )alkyl, (C ₃ -C ₇ )cycloalkyl, cyano-(C1-C ₇ )alkyl, (C ₃ C ₇ )cycloalkyl-(C1-C ₇ )alkyl, ( C1-C ₇ ) alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C ₃ C ₇ ) cycloalkylsulfonyl, heterocyclylsulfonyl, aryl-(C ₁ -C ₇ ) alkylsulfonyl, (C ₁ -C ₇ ) alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C ₃ -C ₇ ) cycloalkylcarbonyl, heterocyclylcarbonyl, (C ₁ -C ₇ ) alkoxycarbonyl, (C ₁ -C ₇ ) alkoxy, (C ₂ -C ₇ ) alkenyloxy, aryl-(C ₁ -C ₇ ) alkoxycarbonyl, (C ₁ -C ₇ ) haloalkylcarbonyl, (C ₂ -C ₇ ) alkenyl, (C ₂ -C ₇ ) alkynyl, (C ₁ -C ₇ ) haloalkyl, halogen-(C ₂ -C ₇ ) alkynyl, halogen (C ₂ -C ₇ ) alkenyl , (C1-C ₇ )alkoxy-(C1-C ₇ )alkyl, amino, (C1-C ₇ )alkylamino, bis[(C1-C ₇ )alkyl]amino, (C1C ₇ )alkoxy-(C ₁ -C ₇ ) alkoxy-(C ₁ -C ₇ ) alkyl, heteroaryl-(C ₁ -C ₇ ) alkylsulfonyl, heterocyclyl-(C ₁ C7) alkylsulfonyl, (C2-C7) alkenyloxycarbonyl, (C2-C7) alkynyloxycarbonyl, (C1- C7)alkylaminocarbonyl, (C3-C7)cycloalkylaminocarbonyl, bis-[(C1-C7)alkyl]aminocarbonyl,

R ¹² is hydrogen, (C1-C7) alkyl, (C3-C7) cycloalkyl-(C1-C7) alkyl, (C2-C7) alkenyl, (C2-C7) alkynyl, (C1-C7) alkoxy-(C1-C7) )alkyl, aryl, aryl-(C1-C7)alkyl, R ¹⁷ O(O)C-(C1-C ₇ )alkyl, R ¹⁵ R ¹⁶ N(O)C(C1-C7)alkyl,

R ¹³ is hydrogen, (C1-C7) alkyl, (C1-C7) haloalkyl, (C3-C7) cycloalkyl, (C3C7) cycloalkyl-(C1-C7) alkyl, (C2-C7) alkenyl, (C2-C7 )alkynyl, (C1-C7)alkoxy-(C1-C7)alkyl, (C1C7)haloalkoxy-(C1-C7)alkyl, aryl, aryl-(C1-C7)alkyl, heteroaryl, heteroaryl-(C1-C7)alkyl , heterocyclyl, heterocyclyl-(C1-C7) alkyl, (C1-C7) alkylthio-(C1-C7) alkyl, (C1-C7) haloalkylthio-(C1-C7) alkyl, (C1-C7) alkylcarbonyl-(C1- C7)alkyl, R ¹⁷ O(O)C-(C1-C7)alkyl, R ¹⁵ R ¹⁶ N(O)C-(C1-C7)alkyl, R ¹⁵ R ¹⁶ N-(CiC7)alkyl, or

R ⁷ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or

R ⁹ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or

R ¹¹ and R ¹³ when X is NR ¹¹ together with the nitrogen atom to which they are attached form a 4-10 membered monocyclic or bicyclic ring which is fully saturated, or

R ¹² and R ¹³ if X is NOR ¹² , together with the nitrogen atom to which they are attached, form a fully saturated substituted 4-10-membered monocyclic or bicyclic ring,

R ¹⁴ is fluorine,

R ¹⁵ and R ¹⁶ are the same or different and are independently hydrogen, (C1C7) alkyl, (C2-C7) alkenyl, (C2-C7) alkynyl, (C1-C7) cyanoalkyl, (C1-C10) haloalkyl, (C2 -C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C10) cycloalkyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4-C10) halocycloalkenyl, (C1-C7) alkoxy-(C1- C7) alkyl, (C1-C7) haloalkoxy-(C1-C7) alkyl, (C1-C7) alkylthio-(C1-C7) alkyl, (C1-C7) haloalkylthio-(C1-C7) alkyl, (C1-C7) ) alkoxy-(C1-C7) haloalkyl, aryl, aryl-(C1-C7) alkyl, heteroaryl, heteroaryl-(C1-C7) alkyl, (C3-C7) cycloalkyl-(C1-C7) alkyl, (C4C10) cycloalkenyl -(C1-C7) alkyl, COR ¹⁷ , SO2R ¹⁸ , (C1-C ₇ )alkyl-HNO ₂ S-, (C ₃ -C ₇ ) cycloalkyl-HNO ₂ S-, heterocyclyl, (C1-C7) alkoxycarbonyl- (C1-C7) alkyl, (C1-C7) alkoxycarbonyl, aryl-(C1-C7) alkoxycarbonyl (C ₁ -C ₇ ) alkyl, aryl-(C ₁ -C ₇ ) alkoxycarbonyl, heteroaryl-(C ₁ -C ₇ ) alkoxycarbonyl, (C ₂ -C ₇ ) alkenyloxycarbonyl, (C ₂ -C ₇ ) alkynyloxycarbonyl, heterocyclyl-(C ₁ -C ₇ ) alkyl,

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R ¹⁷ is hydrogen, (C1-C ₇ )alkyl, (C ₂ -C ₇ )alkenyl, (C ₂ -C ₇ )alkynyl, (C1-C ₇ )cyanoalkyl, (C1-C ₇ ) haloalkyl, (C ₂ -C ₇ ) haloalkenyl, (C ₂ -C ₇ ) haloalkynyl, (C ₃ -C ₁₀ ) cycloalkyl, (C3-C| ₀ ) halocycloalkyl, (C ₄ -C ₁₀ ) cycloalkenyl, (C ₄ -C ₁₀ ) halocycloalkenyl, (C ₁ -C ₇ )alkoxy-(C ₁ -C ₇ )alkyl, (C ₁ C ₇ )alkoxy-(C1-C ₇ )haloalkyl, aryl, aryl-(C1-C ₇ )alkyl, heteroaryl, heteroaryl-(C1-C ₇ )alkyl, (C ₃ C ₇ )cycloalkyl-(C ₁ -C ₇ )alkyl, (C ₄ -C ₁₀ )cycloalkenyl-(C ₁ -C ₇ )alkyl, (C ₁ -C ₇ ) alkoxycarbonyl-(C ₁ -C ₇ ) alkyl, (C ₂ -C ₇ ) alkenyloxycarbonyl-(C ₁ -C ₇ ) alkyl, aryl-(C ₁ -C ₇ ) alkoxycarbonyl-(C ₁ -C ₇ ) alkyl , hydroxycarbonyl-(C ₁ -C ₇ )alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₇ )alkyl,

R ¹⁸ is hydrogen, (C1-C ₇ )alkyl, (C ₂ -C ₇ )alkenyl, (C ₂ -C ₇ )alkynyl, (C1-C ₇ )cyanoalkyl, (C1-C ₁₀ ) haloalkyl, (C ₂ -C ₇ ) haloalkenyl, (C ₂ -C ₇ ) haloalkynyl, (C ₃ -C ₁₀ ) cycloalkyl, (C ₃ -C ₁₀ ) halocycloalkyl, (C ₄ -C ₁₀ ) cycloalkenyl, (C ₄ -C ₁₀ ) halocycloalkenyl, (C ₁ -C ₇ )alkoxy-(C ₁ -C ₇ )alkyl, (Cp C7) alkoxy-(C1-C7) haloalkyl, aryl, aryl-(C1-C7) alkyl, heteroaryl, heteroaryl-(C1 -C7) alkyl, heterocyclyl-(C1-C ₇ ) alkyl, (C ₃ -C ₇ ) cycloalkyl-(C 1 -C ₇ ) alkyl, (C ₄ -C ₁₀ ) cycloalkenyl-(CpC ₇ ) alkyl, NR ¹⁵ R ¹⁶ .

The present invention more preferably provides compounds of general formula (I), in which

R ¹ is (C1-C ₆ )alkyl,

R ² is hydrogen, (C1-C ₆ )alkyl,

R ³ is halogen,

R ⁴ is halogen,

R ⁵ and R ⁶ together with the carbon atom to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring, m is 0, p is 0, 1, 2, 3,

X is O (oxygen), N (nitrogen), or NR ¹¹ or NOR ¹² moieties, and R ¹¹ and R ¹² in NR ¹¹ and NOR ¹² moieties independently have the meanings as defined below,

R ⁷ , R ⁸ R ⁹ and R ¹⁰ are independently hydrogen, fluoro, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl-(C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C10) haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4-C10) halocycloalkenyl , (C1-C6) alkoxy-(C1-C6) haloalkyl, (C1-C6) haloalkoxy-(C1-C6) haloalkyl, aryl, aryl-(C1-C6) alkyl, heteroaryl, heteroaryl-(C1-C6) alkyl , (C4-C10) cycloalkenyl-(C1-C6) alkyl, heterocyclyl, heterocyclyl-(C1-C6) alkyl, R ¹⁷ O-(C1-C ₆ ) alkyl, R ¹⁸ S-(C ₁ -C ₆ ) alkyl , (C ₁ -C ₆ )alkylcarbonyl-(C ₁ C6) alkyl, C(O)OR ¹⁷ , C(O)NR ¹⁵ R ¹⁶ , C(O)R ¹⁷ , R ¹⁷ O(O)C-(C1 -C6)alkyl, R ¹⁵ R ¹⁶ N(O)C-(C1-C6)alkyl, R ¹⁵ R ¹⁶ N(C1-C6)alkyl, or

R ⁵ and R ⁷ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 8-membered monocyclic or bicyclic ring, or

R ⁷ and R ⁸ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or

R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or

R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form an exomethylene group, or

R ⁷ and R ⁹ together with the carbon atoms to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring,

R ¹¹ is hydrogen, (C1-C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, cyano-(C1-C ₆ )alkyl, (C ₃ C ₆ )cycloalkyl-(C ₁ -C ₆ )alkyl, (C1- _C6 )alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, ( _C3C6 )cycloalkylsulfonyl, heterocyclylsulfonyl, aryl-(C1-C6)alkylsulfonyl, (C1-C6)alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C3-C6)cycloalkylcarbonyl, heterocyclylcarbonyl, (C1-C6) alkoxycarbonyl, (C1-C6) alkoxy, (C2-C6) alkenyloxy, aryl-(C1-C6) alkoxycarbonyl, (C1-C6) haloalkylcarbonyl, (C2-C6) alkenyl, (C2-C6) alkynyl , (C1-C6) haloalkyl, halogen-(C2-C6) alkynyl, halo(C ₂ -C ₆ )alkenyl, (C ₁ -C ₆ )alkoxy-(C ₁ -C ₆ )alkyl, amino, (C1- C ₆ )alkylamino, bis[(C1-C ₆ )alkyl]amino, (Cp C ₆ )alkoxy-(C ₁ -C ₆ )alkoxy-(C ₁ -C ₆ )alkyl, heteroaryl-(C ₁ -C ₆ ) alkylsulfonyl, heterocyclyl-(C ₁ C ₆ ) alkylsulfonyl, (C ₂ -C ₆ ) alkenyloxycarbonyl, (C ₂ -C ₆ ) alkynyloxycarbonyl, (C ₁ -C ₆ ) alkylaminocarbonyl, (C ₃ -C ₆ ) cycloalkylaminocarbonyl, bis -[(C ₁ -C ₆ )alkyl]aminocarbonyl,

R ¹² is hydrogen, (C1-C6) alkyl, (C3-C6) cycloalkyl-(C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy-(C1-C6 )alkyl, aryl, aryl-(C1-C6)alkyl, R ¹⁷ O(O)C-(C1-C ₆ )alkyl, R ¹⁵ R ¹⁶ N(O)C(C ₁ -C ₆ )alkyl,

R ¹³ is hydrogen, (C1-C6) alkyl, (CpC6) haloalkyl, (C3-C6) cycloalkyl, (C3C6) cycloalkyl-(C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C1C6)haloalkoxy-(C1-C6)alkyl, aryl, aryl-(C1-C6)alkyl, heteroaryl, heteroaryl-(C1-C6)alkyl, heterocyclyl, heterocyclyl-(C1-C6) alkyl, (C1-C6)-alkylthio-(C1-C6) alkyl, (C1-C6) haloalkylthio-(C1C6) alkyl, (C1-C6) alkylcarbonyl-(C1-C6) alkyl, R ¹⁷ O(O)C-(C1-C ₆ )alkyl, R ¹⁵ R ¹⁶ N(O)C-(C1-C6) alkyl, R ¹⁵ R ¹⁶ N-(C1-C ₆ )alkyl, or

R ⁷ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or

- 5 042989

R ⁹ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or

R ¹¹ and R ¹³ when X is NR ¹¹ together with the nitrogen atom to which they are attached form a 4-10 membered monocyclic or bicyclic ring which is fully saturated, or

R ¹² and R ¹³ if X is NOR ¹² , together with the nitrogen atom to which they are attached, form a fully saturated 4-10-membered monocyclic or bicyclic ring,

R ¹⁴ is fluorine,

R ¹⁵ and R ¹⁶ are the same or different and are independently hydrogen, (Cp C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) cyanoalkyl, (C1-C10) haloalkyl, ( C2C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C10) cycloalkyl, (C3-C10) halocycloalkyl, (C4C10) cycloalkenyl, (C4-C10) 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-( C1C6) haloalkyl, aryl, aryl-(C1-C6) alkyl, heteroaryl, heteroaryl-(C1-C6) alkyl, (C3-C6) cycloalkyl-(C1C6) alkyl, (C4-C10) cycloalkenyl-(C1-C6) alkyl, COR ¹⁷ , SO2R, (C1-C ₆ )alkyl-HNO ₂ S-, (C ₃ -C ₆ )cycloalkylHNO ₂ S-, heterocyclyl, (C ₁ -C ₆ ) alkoxycarbonyl-(C ₁ -C ₆ ) alkyl, (C ₁ -C ₆ )alkoxycarbonyl, aryl-(C ₁ C ₆ )alkoxycarbonyl-(C ₁ -C ₆ )alkyl, aryl-(C ₁ -C ₆ )alkoxycarbonyl, heteroaryl-(C ₁ -C ₆ ) alkoxycarbonyl, (C ₂ -C ₆ )alkenyloxycarbonyl, (C ₂ -C ₆ )alkynyloxycarbonyl, heterocyclyl-(C ₁ -C ₆ )alkyl,

R ¹⁷ is hydrogen, (C ₁ -C ₆ )alkyl, (C ₂ -C ₆ )alkenyl, (C ₂ -C ₆ )alkynyl, (C ₁ -C ₆ )cyanoalkyl, (C ₁ -C ₆ ) haloalkyl _{. _ _ _ _ _ _ _} , (C1-C6)alkoxy-(C1-C6)alkyl, (C1C6)alkoxy-(C1-C6)haloalkyl, aryl, aryl-(C1-C6)alkyl, heteroaryl, heteroaryl-(C1-C6)alkyl, ( C3C6) cycloalkyl-(C1-C6) alkyl, (C4-C10) cycloalkenyl-(C1-C6) alkyl, (C1-C6) alkoxycarbonyl-(C1-C6) alkyl, (C2-C6) alkenyloxycarbonyl-(C1-C6) )alkyl, aryl-(C1-C6)alkoxycarbonyl-(C1-C6)alkyl, hydroxycarbonyl-(C1-C6)alkyl, heterocyclyl, heterocyclyl-(C1-C6)alkyl,

R ¹⁸ is hydrogen, (C1-C ₆ )alkyl, (C ₂ -C ₆ )alkenyl, (C ₂ -C ₆ )alkynyl, (C1-C ₆ )cyanoalkyl, (C ₁ -C ₁₀ ) haloalkyl, ( C ₂ -C ₆ ) haloalkenyl, (C ₂ -C ₆ ) haloalkynyl, (C ₃ -C ₁₀ ) cycloalkyl, (C ₃ C ₁₀ ) halocycloalkyl, (C ₄ -C ₁₀ ) cycloalkenyl, (C ₄ -C ₁₀ ) halocycloalkenyl, (C ₁ -C ₆ )alkoxy-(C ₁ C ₆ )alkyl, (C ₁ -C ₆ )alkoxy-(C ₁ -C ₆ )haloalkyl, aryl, aryl-(C ₁ -C ₆ )alkyl, heteroaryl, heteroaryl-(C ₁ C ₆ )alkyl, heterocyclyl-(C ₁ -C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl-(C ₁ -C ₆ )alkyl, (C ₄ -C ₁₀ )cycloalkenyl- (C ₁ C ₆ )alkyl, NR ¹⁵ R ¹⁶ .

The present invention even more preferably provides compounds of general formula (I), in which

R ¹ is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2methylpropyl, 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, 2methylpentyl, 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,

R ² is hydrogen, methyl, ethyl, n-propyl, isopropyl,

R ³ is fluorine, chlorine, bromine,

R ⁴ is halogen,

R ⁵ and R ⁶ are independently hydrogen, fluoro, methyl, ethyl, n-propyl, 1-methylethyl, nbutyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2- methylbutyl, 3methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex- 4-yl, 3spiro[2.3]hex-5-yl, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, 1-methylcyclopropyl, 2- methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1'bi(cyclopropyl)-1-yl, 1,1'-bi(cyclopropyl)-2-yl, 2'-methyl-1,1' -bi(cyclopropyl)-2-yl, 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3dimethylcyclobut-1-yl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 3,3difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocycloprop-1-yl, 2fluorocycloprop-1-yl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1- vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2methoxycyclohexyl, 3-methoxycyclohexyl, 2-fluorocycloprop-1-yl, 4-fluorocyclohexyl, 4,4difluorocyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1- dimethyl-2propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3methyl-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, 1methyl-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, 1,3dimethyl-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, 2ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1ethyl-2- methyl-2-propenyl, 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, 2methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1- hexynyl, 2hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4pentynyl, 2-methyl-3-pentynyl, 2-methyl- 4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl1-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-3butynyl, 1-ethyl-1-methyl-2-propynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlordifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2- fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, methoxy-n-propyl, methoxydifluoromethyl, ethoxydifluoromethyl, n-propyloxydifluoromethyl, n-butyloxydifluoromethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, phenyl, 2- fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3, 5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4- iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-bromophenyl, 3-fluoro-4-bromophenyl, 3-chloro-4-bromophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-fluorophenyl, 2fluoro-3- chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,5-trimethylphenyl, 3, 4,5trimethylphenyl, 2,4,6-trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4- dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 3difluoromethoxyphenyl, 4- difluoromethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 3,5bis(trifluoromethyl)phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3- methyl-5fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2-trifluoromethylthiophenyl, 3-trifluoromethylthiophenyl, 4-trifluoromethylthiophenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-methoxycarbonylphenyl, 3-methoxycarbonylphenyl, 4methoxycarbonylphenyl, 2-ethoxycarbonylphenyl, 3-ethoxycarbonylphenyl, 4-ethoxycarbonylphenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2yl, pyrimidin-5-yl, pyrimidin-4- yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2ylmethyl, pyrimidin-5-ylmethyl, pyrimidin-4-ylmethyl, pyrazin-2-ylmethyl, 3-chloropyrazin-2-yl, 3-bromopyrazin-2-yl, 3-methoxypyrazin-2-yl, 3-ethoxypyrazin-2-yl, 3-trifluoromethylpyrazin-2-yl, 3-cyanopyrazin-2-yl, naphth-2-yl, naphth-1-yl, quinolin-4-yl, quinolin- 6-yl, quinolin-8-yl, quinolin-2-yl, quinoxalin-2-yl, 2-naphthylmethyl, 1-naphthylmethyl, quinolin-4-ylmethyl, quinolin-6-ylmethyl, quinolin-8ylmethyl, quinolin-2- ylmethyl, quinoxalin-2-ylmethyl, pyrazin-2-ylmethyl, 4-chloropyridin-2-yl, 3-chloropyridin-4-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2-chloropyridin-5- yl, 2,6-dichloropyridin4-yl, 3-chloropyridin-5-yl, 3,5-dichloropyridin-2-yl, 3-chloro-5-trifluoromethylpyridin-2-yl, (4chloropyridin-2-yl)methyl, ( 3-chloropyridin-4-yl)methyl, (2-chloropyridin-3-yl)methyl, (2-chloropyridin-4yl)methyl, (2-chloropyridin-5-yl)methyl, (2,6-dichloropyridin-4- yl)methyl, (3-chloropyridin-5-yl)methyl, (3,5-dichloropyridin-2-yl)methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophen-2-yl, 5- ethylthiophen-2-yl, 5-chlorothiophen-2-yl, 5-bromothiophen-2-yl, 4-methylthiophen-2-yl, 3-methylthiophen-2-yl, 5-fluorothiophenyl-3-yl, 3.5

- 7 042989 dimethylthiophen-2-yl, 3-ethylthiophen-2-yl, 4,5-dimethylthiophen-2-yl, 3,4-dimethylthiophen-2-yl, 4chlorothiophen-2-yl, furan-2-yl, 5 -methylfuran-2-yl, 5-ethylfuran-2-yl, 5-methoxycarbonylfuran-2-yl, 5-chlorofuran-2-yl, 5-bromofuran-2-yl, thiophan-2-yl, thiophan-3-yl, sulfolane -2-yl, sulfolan-3-yl, tetrahydrothiopyran-4-yl, tetrahydropyran-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 1-(4methylphenyl)ethyl, 1-(3-methylphenyl)ethyl , 1-(2-methylphenyl)ethyl, 1-(4-chlorophenyl)ethyl, 1-(3chlorophenyl)ethyl, 1-(2-chlorophenyl)ethyl, benzyl, (4-fluorophenyl)methyl, (3-fluorophenyl)methyl , (2fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3,5-difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6difluorophenyl)methyl, (2,4,5-trifluorophenyl)methyl , (2,4,6-trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4-dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl, ( 2,5dichlorophenyl)methyl, (2,6-dichlorophenyl)methyl, (2,4,5-trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, (4-bromophenyl)methyl, (3-bromophenyl)methyl , (2-bromophenyl)methyl, (4-iodophenyl)methyl, (3-iodophenyl)methyl, (2-iodophenyl)methyl, (3-chloro-5-trifluoromethylpyridin-2-yl)methyl, (2-bromo-4 -fluorophenyl)methyl, (2-bromo4-chlorophenyl)methyl, (3-bromo-4-fluorophenyl)methyl, (3-bromo-4-chlorophenyl)methyl, (3-bromo-5-fluorophenyl)methyl, (3- bromine-5-chlorophenyl)methyl, (2-fluoro-4-bromophenyl)methyl, (2-chloro-4-bromophenyl)methyl, (3fluoro-4-bromophenyl)methyl, (3-chloro-4-bromophenyl)methyl, (2-chloro-4-fluorophenyl)methyl, (3-chloro-4fluorophenyl)methyl, (2-fluoro-3-chlorophenyl)methyl, (2-fluoro-4-chlorophenyl)methyl, (2-fluoro-5-chlorophenyl )methyl, (3-fluoro-4-chlorophenyl)methyl, (3-fluoro-5-chlorophenyl)methyl, (2-fluoro-6-chlorophenyl)methyl, 2-phenylethyl-1-yl, 3trifluoromethyl-4-chlorophenyl, 3-chloro-4-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5difluoropyridin-2-yl, (3,6-dichloropyridin-2-yl)methyl, (4-trifluoromethylphenyl)methyl, (3-trifluoromethylphenyl)methyl , (2-trifluoromethylphenyl)methyl, (4-trifluoromethoxyphenyl)methyl, (3-trifluoromethoxyphenyl)methyl, (2-trifluoromethoxyphenyl)methyl, (4-methoxyphenyl)methyl, (3-methoxyphenyl)methyl, (2methoxyphenyl)methyl, (4 -methylphenyl)methyl, (3-methylphenyl)methyl, (2-methylphenyl)methyl, (4cyanophenyl)methyl, (3-cyanophenyl)methyl, (2-cyanophenyl)methyl, (2,4-diethylphenyl)methyl, (3, 5diethylphenyl)methyl, (3,4-dimethylphenyl)methyl, (3,5-dimethoxyphenyl)methyl, 1-phenylethyl-1-yl, 1-(ochlorophenyl)eth-1-yl, 1,3-thiazol-2-yl , 4-methyl-1,3-thiazol-2-yl, 1,3-thiazol-2-yl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, n-propylthiomethyl, isopropylthiomethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, methylcarbonylmethyl, ethylcarbonylmethyl, n-propylcarbonylmethyl , isopropylcarbonylmethyl, methylcarbonylethyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, npropyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, npropylaminocarbonyl, isopropylaminocar bonyl, dimethylaminocarbonyl, diethylaminocarbonyl, methyl(ethyl)aminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl , cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, allylaminocarbonyl, benzylaminocarbonyl, tert-butyloxycarbonylaminocarbonyl, hydroxycarbonylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, n-butyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, allyloxycarbonyl methyl, benzyloxycarbonylmethyl, aminocarbonylmethyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, n-propylaminocarbonylmethyl, isopropylaminocarbonylmethyl, dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, methyl (ethyl)aminocarbonylmethyl, cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl, cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl, allylaminocarbonylmethyl, benzylaminocarbonylmethyl, 1-(hydroxycarbonyl)eth-1-yl, 1-(methoxycarbonyl)eth-1-yl, 1-(ethoxycarbonyl)eth-1-yl, 1(tert-butyloxycarbonyl)eth-1-yl, 1-(benzyloxycarbonyl)eth-1-yl, 2-(hydroxycarbonyl)eth-1-yl, 2(methoxycarbonyl)eth-1-yl, 2-(ethoxycarbonyl)eth -1-yl, 2-(tert-butyloxycarbonyl)eth-1-yl, 2-(benzyloxycarbonyl)eth-1-yl, 1-(hydroxycarbonyl)prop-1-yl, 1-(methoxycarbonyl)prop-1-yl , 1-(ethoxycarbonyl)prop-1-yl, 1-(tert-butyloxycarbonyl)prop-1-yl, 1-(benzyloxycarbonyl)prop-1-yl, 2(hydroxycarbonyl)prop-1-yl, 2-(methoxycarbonyl) )prop-1-yl, 2-(ethoxycarbonyl)prop-1-yl, 2-(tert-butyloxycarbonyl)prop-1-yl, 2-(benzyloxycarbonyl)prop-1-yl, 1-(hydroxycarbonyl)prop-2-yl , 1(methoxycarbonyl)prop-2-yl, 1-(ethoxycarbonyl)prop-2-yl, 1-(tert-butyloxycarbonyl)prop-2-yl, 1(benzyloxycarbonyl)prop-2-yl, 3-(hydroxycarbonyl) prop-1-yl, 3-(methoxycarbonyl)prop-1-yl, 3(ethoxycarbonyl)prop-1-yl, 3-(tert-butyloxycarbonyl)prop-1-yl, 3-(benzyloxycarbonyl)prop-1-yl , aminomethyl, 2-aminoethyl-1-yl, 1-aminoethyl-1-yl, 1-aminoprop-1-yl, 3-aminoprop-1-yl, methylaminomethyl, dimethylaminomethyl, diethylaminomethyl, ethylaminomethyl, isopropylaminomethyl, cyclopropylaminomethyl, cyclobutylaminomethyl, cyclopentylaminomethyl , cyclohexylaminomethyl, methoxycarbonylaminomethyl, ethoxycarbonylaminomethyl, tert-butyloxycarbonylaminomethyl, methylcarbonylaminomethyl, ethylcarbonylaminomethyl, n-propylcarbonylaminomethyl, isopropylcarbonylaminomethyl, 2(methylamino)eth-1-yl, 2-(dieth-1-ylamino)eth-1-yl, 2-(diethylamino )eth-1-yl, 2-(ethylamino)eth-1-yl, 2(isopropylamino)eth-1-yl, 2-(cyclopropylamino)eth-1-yl, 2-(cyclobutylamino)eth-1-yl, 2-(cyclopentylamino)eth-1-yl, 2-(cyclohexylamino)eth-1-yl, 2-(methoxycarbonylamino)eth-1-yl, 2-(ethoxycarbonylamino)eth-1-yl, 2-(tert-butyloxycarbonylamino )eth-1-yl, 2-(methylcarbonylamino)eth-1-yl, 2(ethylcarbonylamino)eth-1-yl, 2-(n-propylcarbonylamino)eth-1-yl, 2-(isopropylcarbonylamino)eth-1- yl, 1-(methylamino)eth-1-yl, 1-(dieth-1-ylamino)eth-1-yl, 1-(diethylamino)eth-1-yl, 1-(ethylamino)eth-1-yl, 1-(isopropylamino)eth-1-yl, 1-(cyclopropylamino)eth-1-yl, 1-(cyclobutylamino)eth-1-yl, 1-(cyclopentylamino)eth-1-yl, 1-( cyclohexylamino) eth-1-yl, 1-(methoxycarbonylamino) eth-1-yl, 1-(ethoxycarbonylamino) eth-1-yl, 1-(tert-butyloxycarbonylamino) eth-1-yl, 1-(methylcarbonylamino) eth- 1-yl, 1(ethylcarbonylamino)eth-1-yl, 1-(n-propylcarbonylamino)eth-1-yl, 1-(isopropylcarbonylamino)eth-1-yl, or

R ⁵ and R ⁶ together with the carbon atom to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring,

R ¹⁴ is fluorine, m is 0, and Q is one of the Q-1-Q-300 moieties below:

Q-1 Q-2 Q-3 Q-4 Q-5

ABOUT O O Q-6 Q-7 Q-8 Q-9 Q-10

^O^Ao^A} Q-11 Q-12 Q-13 Q-14 Q-15

^ο^Αο^θ^^ 'Άχ Q-16 Q-17 Q-18 Q-19 Q-20

^<DH ^N \ _o jJA -ΑΛΑ -AJU Q-21 Q-22 Q-23 Q-24 Q-25

'^crkAo'^ Q-26 Q-27 Q-28 Q-29 Q-30

0 4%^ Q-31 Q-32 Q-33 Q-34 Q-3 5

O ^°x><5 ^o XQi ^o^Ao^z 'Άά' 'Xo^Ao'^ Q-3 6 Q-37 Q-3 8 Q-39 Q-40

z°Jo' ^H Z°Jo^

- 9 042989

Q-41 Q-42 Q-43 Q-44 Q-45

X°xAo^Q O χθΑ^ Q-46 Q-47 Q-48 Q-49 Q-50

M— O ___ ^Z °^°U) x) Q-51 Q-52 Q-53 Q-54 Q-55

ABOUT Q-56 Q-57 Q-58 Q-59 Q-60

/°Before'Xx°h O | l___JL X. Χ°Ά _ο ^γΧ ^Cl Q-61 Q-62 Q-63 Q-64 Q-65

AA^ X^CF ₃ / ^about Dou2u ^SRz ^θχ^'ο^Χ^Χι^ ⁰¹ ° ^X '0 _a Q-66 Q-67 Q-68 Q-69 Q-70

χΟγΑ O 0 xyA Q-71 Q-72 Q-73 Q-74 Q-75

x°yVo Ύ°^ ABOUT ABOUT O Q-76 Q-77 Q-78 Q-79 Q-80

/°γ _Ο ' ^Η X°yV x^ _χ °γ ₀ Λ ^A<rU

- 10 042989

Q-81 Q-82 Q-83 Q-84 Q-85

Q-86 Q-87 Q-88 Q-89 Q-90

X 0 X o •x Q-91 Q-92 Q-93 Q-94 Q-95

¢1½ -0¼ 0^ Q-96 Q-97 Q-98 Q-99 Q-100

χθ/^ χ°χ®Ά χ ^ο 2/Α Q-101 Q-102 Q-103 Q-104 Q-105

x-xVy x°/^ Q-106 Q-107 Q-108 Q-109 Q-110

X _o x^f _o x ABOUT Q-ll Q-112 Q-113 Q-114 Q-115

X°^°XQ 0 0 Xcr^Jo-Xi^ Q-116 Q-117 Q-118 Q-119 Q-120

Vo χ<ΑΑο' ^Η A

- 11 042989

Q-121 I Q-122 I Q-123 Q-124 Q-125

^v o 'όχΑοΑ' Q-126 Q-127 Q-128 Q-129 Q-130

0 Q-131 Q-132 Q-133 Q-134 Q-135

ABOUT -Λ- Q-136 Q-137 Q-138 Q-139 Q-140

z°v\ S~o o /Vyo \-o -\ O Q-141 Q-142 Q-143 Q-144 Q-145

Q-146 Q-147 Q-148 Q-149 Q-150

ABOUT H H Q-151 Q-152 Q-153 Q-154 Q-155

0 X-xAn^Q ^o^A^ xJk/ 0 Q-156 Q-157 Q-158 Q-159 Q-160

Q-161 Q-162 Q-163 Q-164 Q-165 -«•Άχγ Q-166 Q-167 Q-168 Q-169 Q-170

^o^Ap-jAj) Q-171 Q-172 Q-173 Q-174 Q-175

Ano. Q-176 Q-177 Q-178 Q-179 Q-180

0 H O H 0 H AΛ H Q-181 Q-182 Q-183 Q-184 Q-185

About ^H and 0 .o.___ η V O H O z°A _n ^ h | H Q-186 Q-187 Q-188 Q-189 Q-190

ABOUT H 0 H A ⁰ V ^OxJLiXxJx, ” XJ 0ci ”XJ About Br .O___Kk-x^rk ” kJ Q-191 Q-192 Q-193 Q-194 Q-195

^ ^Ox ^^CX _f ^HLI Α'-Α.ρθ^ Q-196 Q-197 Q-198 Q-199 Q-200

/\Ar\z\ H χ Α% ''°'^X^y ^F ,X°AjpQ^ ^CI XA;pQX' Q-201 Q-202 Q-203 Q-204 Q-205

- 12 042989

- 13 042989

Q-281 Q-282 Q-283 Q-284 Q-285

^ΝΗ X°---V %' Ι^ΝΗ Q-286 Q-287 Q-288 Q-289 Q-290

^ο^ο' ^Η ο 0 Q-291 Q-292 Q-293 Q-294 Q-295

ο 'V ο Q-296 Q-297 Q-298 Q-299 Q-300

The present invention particularly preferably provides compounds of general formula (I) in which

R ¹ is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2methylpropyl, 1,1-dimethylethyl, n-pentyl,

R ² is hydrogen, methyl, ethyl, n-propyl, isopropyl,

R ³ is fluorine, chlorine, bromine,

R ⁴ is halogen,

R ⁵ and R ⁶ are independently hydrogen, fluoro, methyl, ethyl, n-propyl, 1-methylethyl, nbutyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2- methylbutyl, 3methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4- pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1- methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 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, 2methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlordifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2, 2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, methoxy-n-propyl, methoxydifluoromethyl, ethoxydifluoromethyl, n-propyloxydifluoromethyl, n-butyloxydifluoromethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4fluorophenyl, 2,4- difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2- chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5dichlorophenyl, 2,4,5- trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, pyridin-2-yl, pyridin-3yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, furan-2- yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 1-(4-methylphenyl)ethyl, 1-(3-methylphenyl)ethyl, 1-(2-methylphenyl)ethyl, 1-(4-chlorophenyl)ethyl, 1-(3chlorophenyl)ethyl, 1-(2-chlorophenyl)ethyl, benzyl, (4-fluorophenyl)methyl, (3-fluorophenyl)methyl, (2fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3.5 -difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6difluorophenyl)methyl, (2,4,5-trifluorophenyl)methyl, (2,4,6-trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4-dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl, (2,5dichlorophenyl)methyl, (2,6-dichlorophenyl)methyl, (2,4 ,5-trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, n-propylthiomethyl, isopropylthiomethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, methylcarbonylmethyl, ethylcarbonylmethyl, npropylcarbonylmethyl, isopropylcarbonylmethyl, methylcarbonylethyl, hydroxycarbonyl, methoxycarbonyl silt, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, methyl(ethyl)aminocarbonyl yl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, allylaminocarbonyl, benzylaminocar

- 14 042989 bonyl, tert-butyloxycarbonylaminocarbonyl, hydroxycarbonylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, n-butyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, allyloxycarbonylmethyl, benzyloxycarbonylmethyl, aminocarbonylmethyl, methylamino carbonylmethyl, ethylaminocarbonylmethyl, n-propylaminocarbonylmethyl, isopropylaminocarbonylmethyl, dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, methyl (ethyl)aminocarbonylmethyl, cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl, cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl, allylaminocarbonylmethyl, benzylaminocarbonylmethyl, 1-(hydroxycarbonyl)eth-1-yl, 1-(methoxycarbonyl)eth-1-yl, 1(ethoxycarbonyl)eth-1-yl, 1 -(tert-butyloxycarbonyl)eth-1-yl, 1-(benzyloxycarbonyl)eth-1-yl, 2-(hydroxycarbonyl)eth-1-yl, 2-(methoxycarbonyl)eth-1-yl, 2-(ethoxycarbonyl) eth-1-yl, 2-(tert-butyloxycarbonyl)eth-1-yl, 2-(benzyloxycarbonyl)eth-1-yl, 1-(hydroxycarbonyl)prop-1-yl, 1-(methoxycarbonyl)prop-1- yl, 1-(ethoxycarbonyl)prop-1-yl, 1-(tert-butyloxycarbonyl)prop-1-yl, 1-(benzyloxycarbonyl)prop-1-yl, 2-(hydroxycarbonyl)prop-1-yl, 2- (methoxycarbonyl)prop-1-yl, 2-(ethoxycarbonyl)prop-1-yl, 2-(tert-butyloxycarbonyl)prop-1-yl, 2-(benzyloxycarbonyl)prop-1-yl, 1(hydroxycarbonyl)prop- 2-yl, 1-(methoxycarbonyl)prop-2-yl, 1-(ethoxycarbonyl)prop-2-yl, 1-(tert-butyloxycarbonyl)prop-2-yl, 1-(benzyloxycarbonyl)prop-2-yl, 3 - (hydroxycarbonyl)prop-1-yl, 3(methoxycarbonyl)prop-1-yl, 3-(ethoxycarbonyl)prop-1-yl, 3-(tert-butyloxycarbonyl)prop-1-yl, 3(benzyloxycarbonyl)prop-1 -yl, aminomethyl, 2-aminoethyl-1-yl, 1-aminoethyl-1-yl, 1-aminoprop-1-yl, 3aminoprop-1-yl, methylaminomethyl, dimethylaminomethyl, diethylaminomethyl, ethylaminomethyl, isopropylaminomethyl, cyclopropylaminomethyl, cyclobutylaminomethyl, cyclopentylaminomethyl . diethylamino)eth-1-yl, 2-(ethylamino)eth-1-yl, 2-(isopropylamino)eth-1-yl, 2-(cyclopropylamino)eth-1yl, 2-(cyclobutylamino)eth-1-yl, 2-(cyclopentylamino)eth-1-yl, 2-(cyclohexylamino)eth-1-yl, 2(methoxycarbonylamino)eth-1-yl, 2-(ethoxycarbonylamino)eth-1-yl, 2-(tert-butyloxycarbonylamino) eth1-yl, 2-(methylcarbonylamino)eth-1-yl, 2-(ethylcarbonylamino)eth-1-yl, 2-(n-propylcarbonylamino)eth-1yl, 2-(isopropylcarbonylamino)eth-1-yl, 1- (methylamino)eth-1-yl, 1-(dieth-1-ylamino)eth-1-yl, 1(diethylamino)eth-1-yl, 1-(ethylamino)eth-1-yl, 1-(isopropylamino) eth-1-yl, 1-(cyclopropylamino)eth-1-yl, 1-(cyclobutylamino)eth-1-yl, 1-(cyclopentylamino)eth-1-yl, 1-(cyclohexylamino)eth-1-yl, 1(methoxycarbonylamino)eth-1-yl, 1-(ethoxycarbonylamino)eth-1-yl, 1-(tert-butyloxycarbonylamino)eth1-yl, 1-(methylcarbonylamino)eth-1-yl, 1-(ethylcarbonylamino)eth- 1-yl, 1-(n-propylcarbonylamino)eth-1yl, 1-(isopropylcarbonylamino)eth-1-yl, or

R ⁵ and R ⁶ together with the carbon atom to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring,

R ¹⁴ is fluoro, m is 0, and Q is one of the Q-1-Q-300 moieties above.

The present invention particularly preferably provides compounds of general formula (I) in which

R ¹ is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2methylpropyl, 1,1-dimethylethyl,

R ² is hydrogen, methyl, ethyl, n-propyl, isopropyl,

R ³ is fluorine, chlorine, bromine,

R ⁴ is fluorine, chlorine, bromine,

R ⁵ and R ⁶ independently represent hydrogen, fluoro, methyl, ethyl, n-propyl, 1-methylethyl, nbutyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2- methylbutyl, 3methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4- pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1- methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 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, 2methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, methoxymethyl, ethoxymethyl, n- 15 042989 propyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, methoxy-n-propyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, phenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, furan-2-yl, tetrahydrofuran-2yl, tetrahydrofuran-3-yl, benzyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, npropylthiomethyl, isopropylthiomethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, or

R ⁵ and R ⁶ together with the carbon atom to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring,

R ¹⁴ is fluorine, m is 0 and

Q is one of the fragments Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-10, Q-11, Q-12, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-31, Q-32, Q-33, Q-41, Q- 42, Q-43, Q-44, Q-45, Q-46, Q47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, Q-57, Q- 61, Q-71, Q-72, Q-73, Q-74, Q-75, Q-76, Q-102, Q-103, Q127, Q-132, Q-133, Q-141, Q- 142, Q-144, Q-145, Q-146, Q-147, Q-148, Q-151, Q-152, Q-153, Q-154, Q-155, Q-156, Q-160, Q-161, Q-166, Q-167, Q-181, Q-182, Q-183, Q-184, Q-185, Q-186, Q-187, Q-188, Q-189, Q190, Q-191, Q-192, Q-201, Q-211, Q-231, Q-232, Q-233, Q-241, Q-242, Q-251, Q-254, Q-255, Q- 292, Q-293, above.

The definitions of radicals, given in general terms or listed in the preferred areas above, apply both to the end products of formula (I) and, accordingly, to the starting materials or intermediates necessary in each case for obtaining. These radical definitions can be combined with each other as desired, i.e. including as a combination between these preferred ranges.

Mainly for reasons of higher herbicidal activity, better selectivity and/or better ease of preparation, particular interest is associated with the compounds of said formula (I) according to the present invention, or their salts, or their use according to the present invention, in which individual radicals have one of the preferred meanings already indicated or indicated hereinafter, or, in particular, with those in which one or more of the preferred meanings already indicated or indicated hereinafter occur in combination.

If the compounds can form, as a result of the displacement of a hydrogen atom, tautomers having structures which will not be covered by formula (I) in the formal sense, such tautomers are nevertheless covered by the definition of compounds of formula (I) in accordance with the present invention, unless a particular tautomer is considered. For example, many carbonyl compounds may be in either the keto form or the enol form, both forms being encompassed by the definition of a compound of formula (I).

Depending on the nature of the substituents and the manner in which they are attached, the compounds of general formula (I) may exist as stereoisomers. All possible stereoisomers defined by their specific three-dimensional form, such as enantiomers, diastereomers and Z- and E-isomers, are covered by formula (I). For example, if one or more alkenyl groups are present, diastereomers (Z and E isomers) can be formed. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers can be formed. Stereoisomers can be obtained from mixtures obtained during preparation using conventional separation methods. Chromatographic separation can be performed either on an analytical scale to determine enantiomeric excess or diastereomeric excess, or on a preparative scale to obtain test samples for biological testing. Similarly, stereoisomers can be selectively obtained by applying stereoselective reactions using optically active starting materials and/or auxiliaries. Thus, the present invention also relates to all stereoisomers which are covered by the general formula (I) but are not defined by their particular stereomeric form, and mixtures thereof.

If the compounds are obtained in solid form, it is also possible to carry out purification by recrystallization or resolution. If individual compounds (I) cannot be obtained satisfactorily using the routes described later in this document, they can be obtained by derivatization of other compounds (I).

Applicable methods for isolating, purifying and separating stereoisomers for compounds of formula (I) include methods known generally to the person skilled in the art from similar cases, for example, using physical methods such as crystallization, chromatography methods, in particular column chromatography and HPLC (high pressure liquid chromatography), distillation, optionally under reduced pressure, extraction and other methods; any remaining mixtures can generally be separated by chromatographic separation, for example on solid chiral phases. For preparative amounts or on an industrial scale, applicable methods include the crystallization of, for example, diastereomeric salts, which can be obtained from mixtures of diastereomers with optically active acids and, if necessary, in the presence of acidic groups, with optically active bases.

- 16 042989

With regard to the compounds of the present invention, the designations used above and further below are explained. They are familiar to the person skilled in the art and, in particular, have the meanings explained later in this document.

Unless otherwise specified, as a rule, in the case of the designation of chemical groups, binding to the backbone or the rest of the molecule occurs through the last structural element indicated in the chemical group in question, i.e., for example, through the oxygen atom in the case of (C ₂ -C ₈ )alkenyloxy, and via the corresponding carbon atom of the alkyl group in the case of heterocyclyl-(C1-C ₈ )alkyl or R ¹⁷ O(O)C-(C ₁ -C ₈ )alkyl.

In accordance with the present invention, an alkylsulfonyl, alone or as part of a chemical group, is a straight or branched alkylsulfonyl, preferably containing 1-8 or containing 1-6 carbon atoms, for example (without limitation) (C 1 -C ₆ ) alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2 -dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3dimethylbutylsulfonyl, 2,2 -dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2 -methylpropylsulfonyl.

In accordance with the present invention, heteroarylsulfonyl is an optionally substituted pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl or an optionally substituted polycyclic heteroarylsulfonyl, herein in particular an optionally substituted quinolinylsulfonyl, e.g. , haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.

In accordance with the present invention, alkylthio, alone or as part of a chemical group, is a straight or branched S-alkyl, preferably containing 1-8 or containing 1-6 carbon atoms, such as (C1-C ₁₀ )-, (C1 -C6)- or (C1-C ₄ )alkylthio, for example (but not limited to) (C1-C ₆ )alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1- dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1, 1,2-trimethylpropylthio, 1,2,2trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio.

In accordance with the present invention, alkenylthio means an alkenyl radical linked via a sulfur atom, alkynylthio means an alkynyl radical linked via a sulfur atom, cycloalkylthio means a cycloalkyl radical linked via a sulfur atom, and cycloalkenylthio means a cycloalkenyl radical linked via a sulfur atom.

Alkylsulfinyl (alkyl-S(=O)-), unless otherwise defined elsewhere, in accordance with the present invention are alkyl radicals linked to the backbone via S(=O)-, such as (C1-C ₁₀ ) -, (C1-C6)- or (C1-C ₄ )alkylsulfinyl, for example (but not limited to) (Cp C ₆ )alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl . -methylpentylsulfinyl, 3methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl silt , 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.

Similarly, alkenylsulfinyl and alkynylsulfinyl are respectively defined in accordance with the present invention as alkenyl and alkynyl radicals linked to the backbone via -S(=O)-, such as (C ₂ -C ₁₀ )-, (C ₂ -C ₆ )- or ( C ₂ -C ₄ )alkenylsulfinyl and (C ₃ -C ₁₀ )-, (C3-C6)- or (C ₃ C4 )alkynylsulfinyl.

Similarly, alkenylsulfonyl and alkynylsulfonyl are respectively defined in accordance with the present invention as alkenyl and alkynyl radicals linked to the backbone via -S(=O) ₂ -, such as (C ₂ -C ₁₀ )-, (C ₂ -C ₆ )- or (C ₂ -C ₄ )alkenylsulfonyl and (C ₃ -C ₁₀ )-, (C3-C6)- or (C ₃ C ₄ )alkynylsulfonyl.

Alkoxy means an alkyl radical linked via an oxygen atom, for example (without

- 17 042989 restrictions) (C,-C ₆ )alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1, 2dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1- ethyl-1-methylpropoxy; and 1-ethyl-2-methylpropoxy. _Alkenyloxy means an alkenyl radical linked via _an oxygen atom, _{alkynyloxy means an} alkynyl radical linked via an oxygen atom, _e.g. -C ₁₀ )-, (C ₃ -C ₆ )- or (C ₃ -C ₄ )alkynyloxy.

Cycloalkyloxy means a cycloalkyl radical linked via an oxygen atom, and cycloalkenyloxy means a cycloalkenyl radical linked via an oxygen atom.

Alkylcarbonyl (alkyl-C(=O)-), unless otherwise defined elsewhere, in accordance with the present invention are alkyl radicals linked to the backbone through -C(=O)-, for example (C1-C1 ₀ ) -, (C1-C6)- or (C1- _C4 )alkylcarbonyl. The number of carbon atoms refers in this case to the alkyl radical in the alkylcarbonyl group.

Similarly, alkenylcarbonyl and alkynylcarbonyl, unless otherwise defined elsewhere, in accordance with the present invention, respectively, are alkenyl and alkynyl radicals linked to the backbone via -C(=O)-, such as (C ₂ -C ₁₀ )- , (C ₂ -C ₆ )- or (C _{2 -C 4} )alkenylcarbonyl and (C ₂ -C ₁₀ )-, (C ₂ -C ₆ )- or (C ₂ -C ₄ )alkynylcarbonyl. The number of carbon atoms refers here to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.

Alkoxycarbonyl (alkyl-O-C(=O)-), unless otherwise specified elsewhere, are alkyl radicals linked to the backbone via -O-C(=O)-, for example (C1-C1 ₀ )- , (C1-C6)- or (C1C4)alkoxycarbonyl. The number of carbon atoms refers in this case to the alkyl radical in the alkoxycarbonyl group. Similarly, alkenyloxycarbonyl and alkynyloxycarbonyl, unless otherwise specified elsewhere, in accordance with the present invention, respectively, are alkenyl and alkynyl radicals linked to the backbone via -O-C(=O)-, such as (C ₂ -C ₁₀ )-, (C ₂ -C ₆ )- or (C ₂ -C ₄ )alkenyloxycarbonyl and (C ₃ -C ₁₀ )-, (C ₃ -C ₆ )- or (C ₃ -C ₄ )alkynyloxycarbonyl. The number of carbon atoms refers here to the alkenyl or alkynyl radical in the alkenyl or alkynyloxycarbonyl group.

In accordance with the present invention, the term alkylcarbonyloxy (alkyl-C(=O)-O-), unless otherwise defined elsewhere, denotes alkyl radicals linked to the backbone via a carbonyloxy group (-C(=O)-O-) with using oxygen, for example (C1-C1 ₀ )-, (C1-Cb)- or (C1-C ₄ )alkylcarbonyloxy. The number of carbon atoms refers here to the alkyl radical in the alkylcarbonyloxy group.

Similarly, alkenylcarbonyloxy and alkynylcarbonyloxy are respectively defined in accordance with the present invention as alkenyl and alkynyl radicals linked to the backbone via (-C(=O)-O-) with oxygen, for example (C ₂ -C ₁₀ )-, (C ₂ - C ₆ )- or (C ₂ C ₄ )alkenylcarbonyloxy and (C ₂ -C ₁₀ )-, (C ₂ -C ₆ )- or (C ₂ -C ₄ )alkynylcarbonyloxy. The number of carbon atoms refers here to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.

In abbreviated forms such as C(O)R ¹⁷ , C(O)OR ¹⁷ , OC(O)NR ¹⁵ R ¹⁶ , or C(O)NR ¹⁵ R ¹⁶ , for example, the abbreviation O in parentheses represents an atom oxygen bonded to an adjacent carbon atom via a double bond.

In abbreviated forms such as OC(S)OR ¹⁷ , OC(S)SR ¹⁸ , OC(S)NR ¹⁵ R ¹⁶ , for example, the abbreviation S in parentheses represents a sulfur atom bonded to an adjacent carbon atom via a double connections.

The term aryl means an optionally substituted mono-, bi- or polycyclic aromatic system, preferably containing 6-14, in particular 6-10, carbon atoms in the ring, eg phenyl, naphthyl, anthryl, phenanthrenyl and the like, preferably phenyl.

The term optionally substituted aryl also includes polycyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the bonding site is on the aromatic system. In a systematic context, aryl is generally also covered by the term optionally substituted phenyl. Preferred aryl substituents in this case are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, Alcoxy, halogenicoxy, cycloalcoxy, cycliclalcoxy, aryloxy, heteroariloxy, alcohoxalcoxy, alkynilalcoxy, alkeniloxy, bisalcalaminalcoxy, tris [alkyl] Silil, bis [alkyil] arilil, bis [alkyil] alkylil [alkyl] silkillers, sirlillecinyl, arilac , heteroarilalkinil, alkylacinyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bisalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino,

- 18 042989 arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, bisalkylaminocarbonyl, heteroarylalkoxy, arylalkoxy.

The heterocyclic radical (heterocycle) contains at least one heterocyclic ring (= carbocyclic ring in which at least one carbon atom is replaced by a heteroatom, preferably a heteroatom from the group consisting of N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, where the binding site is located on a ring atom. If the heterocyclyl radical or heterocyclic ring is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, polycyclic systems are also included, for example 8-azabicyclo[3.2.1]octanyl, 8azabicyclo[2.2.2]octanyl or 1-azabicyclo[2.2.1]heptyl. In the case of optionally substituted heterocyclyl, spirocyclic systems are also included, for example 1-oxa-5-azaspiro[2.3]hexyl. Unless otherwise specified, the heterocyclic ring preferably contains 3-9 ring atoms, in particular 3-6 ring atoms, and one or more, preferably 1-4, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group consisting of N, O and S, although the two oxygen atoms need not be directly adjacent, for example with one heteroatom from the group consisting of N, O and S: 1-, or 2-, or 3-pyrrolidinyl, 3,4-dihydro -2H-pyrrol-2- or 3-yl, 2,3-dihydro-1H-pyrrole1-, or 2-, or 3-, or 4-, or 5-yl; 2,5-dihydro-III-pyrrole-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6-tetrahydropyridin-1-, or 2-, or 3-, or 4-, or 5-, or 6-yl; 1,2,3,4-tetrahydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridin-1-, or 2-, or 3-, or 4-yl; 2,3-dihydropyridin-2-, or 3-, or 4-, or 5-, or 6-yl; 2,5-dihydropyridine-2-, or 3-, or 4-, or 5-, or 6-yl, 1-, or 2-, or 3-, or 4-azepanil; 2,3,4,5-tetrahydro-1H-azepin-1-, or 2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,4,7tetrahydro-1H-azepin-1-, or 2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,6,7-tetrahydro-1H-azepin-1-, or 2-, or 3-, or 4-yl; 3,4,5,6-tetrahydro-2H-azepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 4,5dihydro-1H-azepin-1-, or 2-, or 3-, or 4-yl; 2,5-dihydro-1H-azepin-1-, or -2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,7-dihydro-1H-azepin-1- or -2- or 3- or 4-yl; 2,3-dihydro-1H-azepin-1-, or -2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 3,4-dihydro-2H-azepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 3,6-dihydro-2H-azepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 5,6-dihydro-2H-azepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 4,5-dihydro-3H-azepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 1H-azepine 1-, or -2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2H-azepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 3H-azepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 4H-azepine-2- or 3- or 4- or 5- or 6- or 7yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2-, or 3-, or 4-, or 5-yl; 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4dihydro-2H-pyran-2-, or 3-, or 4-, or 5-, or 6-yl; 3,6-dihydro-2H-pyran-2-, or 3-, or 4-, or 5-, or 6-yl; 2H-pyran-2- or 3- or 4- or 5- or 6-yl; 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,4,7tetrahydrooxepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,6,7-tetrahydrooxepin-2- or 3- or 4-yl; 2,3-dihydrooxepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 4,5-dihydrooxepin-2- or 3- or 4-yl; 2,5-dihydrooxepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; oxepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophen-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophen-2- or 3-yl; tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2-, or 3-, or 4-, or 5-, or 6-yl; 3,6-dihydro-2H-thiopyran-2-, or 3-, or 4-, or 5-, or 6-yl; 2Nthiopyran-2-, or 3-, or 4-, or 5-, or 6-yl; 4H-thiopyran-2- or 3- or 4-yl.

Preferred 3rd 4-membered heterocyclic rings are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl , 1,3-dioxetan-2-yl. Additional examples of heterocyclyl are a partially or fully hydrogenated heterocyclic radical containing two heteroatoms from the group consisting of N, O and S, for example 1-, or 2-, or 3-, or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazol-1-, or 3-, or 4-, or 5-yl; 2,3-dihydro-1H-pyrazol-1-, or 2-, or 3-, or 4-, or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazol-1-, or 2-, or 3-, or 4-yl; 2,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazol-1-, or 2-, or 4-, or 5-yl; hexahydropyridazin-1-, or 2-, or 3-, or 4-yl; 1,2,3,4-tetrahydropyridazin-1-, or 2-, or 3-, or 4-, or 5-, or 6-yl; 1,2,3,6-tetrahydropyridazin-1-, or 2-, or 3-, or 4-, or 5-, or 6-yl; 1,4,5,6-tetrahydropyridazin-1-, or 3-, or 4-, or 5-, or 6-yl; 3,4,5,6-tetrahydropyridazin-3-, or 4-, or 5yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3-, or 4-, or 5-, or 6-yl; 3,6dihydropyridazin-3- or 4-yl; 1,6-dihydropyridazin-1-, or 3-, or 4-, or 5-, or 6-yl;

hexahydropyrimidin-1- or 2- or 3- or 4-yl; 1,4,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidin-1-, or 2-, or 4-, or 5-, or 6-yl; 1,2-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidin-2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or 6-yl; 1,4-dihydropyrimidine-1-, or 2-, or 4-,

- 19 042989 or 5- or 6-yl; 1-, or 2-, or 3-piperazinyl;

1,2, 3,6-tetrahydropyrazin-1-, or 2-, or 3-, or 5-, or 6-yl; 1,2,3,4-tetrahydropyrazin-1-, or 2-, or 3-, or 4-, or 5-, or 6-yl; 1,2-dihydropyrazin-1-, or 2-, or 3-, or 5-, or 6-yl; 1,4dihydropyrazin-1- or 2- or 3-yl; 2,3-dihydropyrazin-2-, or 3-, or 5-, or 6-yl; 2,5dihydropyrazin-2- or 3-yl; 1,3-dioxolane-2- or 4- or 5-yl; 1,3-dioxol-2- or 4-yl; 1,3-dioxane-2- or 4- or 5-yl; 4H-1,3-dioxin-2-, or 4-, or 5-, or 6-yl; 1,4-dioxan-2-, or 3-, or 5-, or 6-yl;

2,3-dihydro-1,4-dioxin-2-, or 3-, or 5-, or 6-yl; 1,4-dioxin-2- or 3-yl; 1,2-dithiolan-3- or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl; 1,3-dithiolan-2- or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3 or 4-yl; 3,4-dihydro-1,2-dithiin-3-, or 4-, or 5-, or 6-yl; 3,6-dihydro-1,2-dithiin-3- or 4-yl; 1,2 dithiin-3- or 4-yl; 1,3-dithian-2- or 4- or 5-yl; 4H-1,3-dithiin-2-, or 4-, or 5-, or 6-yl;

isoxazolidin-2-, or 3-, or 4-, or 5-yl; 2,3-dihydroisoxazol-2-, or 3-, or 4-, or 5-yl; 2,5-dihydroisoxazol-2-, or 3-, or 4-, or 5-yl; 4,5-dihydroisoxazol-3- or 4- or 5-yl; 1,3oxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-oxazol-2-, or 3-, or 4-, or 5-yl; 2,5dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 1,2-oxazinan-2-, or 3-, or 4-, or 5-, or 6-yl; 3,4-dihydro-2H-1,2-oxazin-2-, or 3-, or 4-, or 5-, or 6-yl;

3,6-dihydro-2H-1,2-oxazin-2-, or 3-, or 4-, or 5-, or 6-yl; 5,6-dihydro-2H-1,2-oxazin-2-, or 3-, or 4-, or 5-, or 6-yl; 5,6-dihydro-4H-1,2-oxazin-3-, or 4-, or 5-, or 6-yl; 2H-1,2-oxazin-2-, or 3-, or 4-, or 5-, or 6-yl; 6H-1,2-oxazin-3-, or 4-, or 5-, or 6-yl; 4H-1,2-oxazin-3-, or 4-, or 5-, or 6-yl; 1,3-oxazinan-2-, or 3-, or 4-, or 5-, or 6-yl; 3,4-dihydro-2H-1,3-oxazin-2-, or 3-, or 4-, or 5-, or 6-yl;

3,6-dihydro-2H-1,3-oxazin-2-, or 3-, or 4-, or 5-, or 6-yl; 5,6-dihydro-2H-1,3-oxazin-2-, or 4-, or 5-, or 6-yl; 5,6-dihydro-4H-1,3-oxazin-2-, or 4-, or 5-, or 6-yl; 2H-1,3-oxazin-2-, or 4-, or 5-, or 6-yl; 6H-1,3-oxazin-2-, or 4-, or 5-, or 6-yl; 4H-1,3-oxazin-2-, or 4-, or 5-, or 6-yl; morpholin-2- or 3- or 4-yl; 3,4-dihydro-2H-1,4-oxazin-2-, or 3-, or 4-, or 5-, or 6-yl; 3,6dihydro-2H-1,4-oxazin-2-, or 3-, or 5-, or 6-yl; 2H-1,4-oxazin-2-, or 3-, or 5-, or 6-yl; 4H-1,4oxazin-2- or 3-yl; 1,2-oxazepan-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl;

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

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

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

2,3,4,5-tetrahydro-1,4-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,4,7-tetrahydro-1,4oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,6,7-tetrahydro-1,4-oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 2,5,6,7-tetrahydro-1,4-oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 4,5,6,7-tetrahydro1,4-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3-dihydro-1,4-oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 2,5-dihydro-1,4-oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 2,7-dihydro-1,4-oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl;

4,5-dihydro-1,4-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 4,7-dihydro-1,4-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 6,7-dihydro-1,4-oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 1,4oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; isothiazolidin-2-, or 3-, or 4-, or 5-yl; 2,3-dihydroisothiazol-2-, or 3-, or 4-, or 5-yl; 2,5-dihydroisothiazol-2-, or 3-, or 4-, or 5-yl; 4,5-dihydroisothiazol-3- or 4- or 5-yl; 1,3-thiazolidin-2-, or 3-, or 4-, or 5-yl; 2,3-dihydro-1,3thiazol-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-thiazinan-2- or 3- or 4- or 5- or 6-yl; 3,4dihydro-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. Additional examples of heterocyclyl are

- 20 042989 is a partially or fully hydrogenated heterocyclic radical containing 3 heteroatoms from the group consisting of N, O and S, for example, 1,4,2-dioxazolidin-2-, or 3-, or 5-yl; 1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazepan-2-, or 3-, or 5-, or 6-, or 7yl; 6,7-dihydro-5H-1,4,2-dioxazepin-3-, or 5-, or 6-, or 7-yl; 2,3-dihydro-7H-1,4,2-dioxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 2,3-dihydro-5H-1,4,2-dioxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 5H1,4,2-dioxazepin-3-, or 5-, or 6-, or 7-yl; 7H-1,4,2-dioxazepin-3-, or 5-, or 6-, or 7-yl. Structure examples of optionally further substituted heterocycles are also listed below.

- 21 042989

The heterocycles listed above are preferably substituted with, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl om, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy , haloalkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, heteroaryloxy, bisalkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonyl alkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.

If the basic structure is substituted by one or more radicals from the list of radicals (= group) or in general by a certain group of radicals, this in each case includes the simultaneous substitution by several identical and/or structurally different radicals.

In the case of a partially or fully saturated nitrogen-containing heterocycle, it can be attached to the rest of the molecule either through carbon or through nitrogen.

Useful substituents on the substituted heterocyclic radical include the substituents listed below, as well as additionally oxo and thioxo. An oxo group as a substituent on a carbon atom in a ring in this case means, for example, a carbonyl group in a heterocyclic ring. As a result, lactones and lactams are preferably also covered. The oxo group may also be present at the heteroatoms of the ring, which may exist in different oxidation states, for example in the case of N and S, and in such a case form, for example, the divalent groups N(O), S(O) (also SO for short) and S(O) ₂ (also SO2 for short) in a heterocyclic ring. In the case of -N(O)- and -S(O)- groups, both enantiomers are included in each case.

In accordance with the present invention, the expression heteroaryl indicates heteroaromatic compounds, i.e. fully unsaturated aromatic heterocyclic compounds, preferably 5-7-membered rings containing from 1 to 4, preferably 1 or 2, identical or different heteroatoms, preferably O, S or N. Heteroaryls according to the present invention are, for example, N-pyrrol-1-yl; SH-pyrrol-2-yl; SH-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl, N-imidazol-1-yl; N-imidazol-2-yl; III-imidazol-4-yl; 1Himidazol-5-yl; W-pyrazol-1-yl; W-pyrazol-3-yl; W-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-triazol1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H- 1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3- yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3yl, azepinyl, pyridin-2-yl, pyridin-3-yl, pyridin- 4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1.3, 5-triazin-2-yl, 1,2,4-triazin-3yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,3-triazin- 4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl , isoxazol-4-yl, isoxazol-5-yl,

1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5yl, 1,3- thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and 1,2,4-diazepinyl, 2H-1,2, 3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3,4-thiatriazol-5- yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl. The heteroaryl groups of the present invention may also be substituted with one or more identical or different radicals. If two adjacent carbons are part of an additional aromatic ring, this results in the formation of fused heteroaromatic systems such as benzocondense

- 22 042989 fused or polycondensed heteroaromatic substances. Preferred examples are quinolines (eg quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); isoquinolines (eg isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7naphthyridine; phthalazine; pyridopyrazines; pyridopyrimidines; pyridopyridazines; pteridines; pyrimidopyrimidines. Examples of heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol- 5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1- benzothiophen-6-yl, 1-benzothiophen-7-yl, N-indazol-1yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6- yl, 1H-indazol-7-yl, 2Nindazol-2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H- indazol-7yl, 2H-isoindol-2-yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6- silt; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H-benzimidazol- 7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1, 2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,2-benzisoxazol-7-yl, 1, 2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1,2-benzisothiazol-7-yl.

The term halogen means, for example, fluorine, chlorine, bromine or iodine. When the term is applied to a radical, halogen means, for example, a fluorine, chlorine, bromine or iodine atom.

In accordance with the present invention, alkyl means a straight or branched, open chain, saturated hydrocarbyl radical, which is optionally mono- or polysubstituted, and in the latter case is called substituted alkyl. Preferred substituents are halogen atoms or alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, more preferably methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine. The prefix bis also includes a combination of various alkyl radicals, such as methyl(ethyl) or ethyl(methyl).

Haloalkyl, -alkenyl and -alkynyl are respectively alkyl, alkenyl and alkynyl partially or completely substituted with identical or different halogen atoms, for example monohaloalkyl, for example CH ₂ CH ₂ Cl, CH ₂ CH ₂ Br, CHClCH ₃ , CH ₂ Cl, CH2F ; perhaloalkyl, for example CCl ₃ , CClF ₂ , CFCl ₂ , CF2CQF2, CF2CQFCF3; polyhaloalkyl, eg CH2CHFCl, CF2CQFH, _CF2CBrFH , CH2CF3; the term perhaloalkyl also includes the term perfluoroalkyl.

Partially fluorinated alkyl means a saturated straight or branched chain hydrocarbon, mono- or polysubstituted with fluorine, where the corresponding fluorine atoms may be present as substituents on one or more different carbon atoms in the straight or branched hydrocarbon, e.g. CHFCH ₃ , CH ₂ CH ₂ F, CH ₂ CH ₂ CF ₃ , CHF ₂ , CH ₂ F, CHFCF ₂ CF ₃ .

Partially fluorinated haloalkyl means a straight or branched saturated hydrocarbon substituted with various halogen atoms and at least one fluorine atom, where any other halogen atoms present are selected from the group consisting of fluorine, chlorine or bromine, iodine. The corresponding halogen atoms may in this case be present as substituents on one or more different carbon atoms of the straight chain or branched hydrocarbon. Partially fluorinated haloalkyl also includes complete substitution of a straight chain or branched chain alkyl with a halogen involving at least one fluorine atom.

Haloalkoxy is, for example, OCF ₃ , OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH ₂ CH ₂ Cl; the same applies to haloalkenyl and other halogen-substituted radicals.

The expression (C1-C ₄ )-alkyl, as used herein by way of example, is a shorthand for straight or branched chain alkyl having from one to 4 carbon atoms according to the indicated carbon atom range, i.e. includes radicals representing methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. Alkyl radicals in general form containing a greater range of carbon atoms, for example (C1-C ₆ )alkyl, also suitably include straight or branched chain alkyl radicals containing a greater number of carbon atoms, i.e. as an example also alkyl radicals containing 5 and 6 carbon atoms.

Unless otherwise stated, in the case of hydrocarbyl radicals such as alkyl, alkenyl and alkynyl radicals, preference is also given to lower carbon backbones in complex radicals, for example those containing 1-6 carbon atoms or, in the case of unsaturated groups, containing 2-6 carbon atoms. . Alkyl radicals included in complex radicals such as alkoxy, haloalkyl, etc. are, for example, methyl, ethyl, n- or isopropyl, n-, iso-, tert- or 2-butyl,

- 23 042989 pentyls, hexyls such as n-hexyl, isohexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals are defined as possible unsaturated radicals corresponding to alkyl radicals where at least one double bond/triple bond is present. Preference is given to radicals containing one double bond/triple bond.

The term alkenyl particularly also includes straight or branched chain, open chain hydrocarbyl radicals containing more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals containing one or several conjugated double bonds, such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3 pentatrienyl. Alkenyl is, for example, vinyl, which may optionally be substituted with additional alkyl radicals, for example (without limitation) (C ₂ -C ₆ )alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl , 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl , 4pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2butenyl, 3-methyl-2-butenyl, 1 -methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl , 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl , 3methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4methyl-2-pentenyl, 1-methyl-3 -pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1methyl-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, 1,3dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1 -ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1 -ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term alkynyl specifically also includes straight or branched chain, open chain, hydrocarbyl radicals containing more than one triple bond, or otherwise containing one or more triple bonds and one or more double bonds, for example 1,3butatrienyl or 3 -penten-1-in-1-yl. (C ₂ -C ₆ )Alkynyl is, for example, ethynyl, 1propynyl, 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, 5hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2 -methyl-3-pentynyl, 2-methyl-4pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1dimethyl-2 -butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1 -ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.

The term cycloalkyl means a carbocyclic saturated ring system, preferably containing 3-8 carbon atoms in the ring, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and optionally including additional substitution, preferably with hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen , alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems containing substituents are included, also including substituents having a double bond at the cycloalkyl radical, for example an alkylidene group such as methylidene. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems also include, for example, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo [1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept -2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl and adamantan-2 -yl, as well as systems such as, for example, 1,1'-bi(cyclopropyl)-1-yl, 1,1'-bi(cyclopropyl)-2-yl. The expression (C3-C7) cycloalkyl is shorthand for cycloalkyl containing from three to 7 carbon atoms in accordance with the specified range for carbon atoms.

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

Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system containing preferably 4-8 carbon atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1 ,3-cyclohexadienyl or 1,4-cyclohexadienyl also including substituents having a double bond at the cycloalkenyl radical, for example an alkylidene group such as methylidene. In the case of an optionally substituted cycloalkenyl, the explanation for substituted cycloalkyl applies accordingly.

The term alkylidene, for example, including in the form of (C1-C ₁₀ )-alkylidene, means the remainder of a straight or branched chain, open chain, hydrocarbyl radical linked via a double bond. Possible bonding sites for the alkylidene typically include exclusively positions on the main structure where two hydrogen atoms can be replaced by a double bond; while the radicals are, for example, =CH ₂ , =CH-CH ₃ , =C(CH ₃ )-CH ₃ , =C(CH ₃ )-C ₂ H ₅ or =C(C ₂ H ₅ )C ₂ H ₅ . Cycloalkylidene is a carbocyclic radical linked via a double bond.

Cycloalkylalkyloxy means a cycloalkylalkyl radical linked via an oxygen atom, and arylalkyloxy means an arylalkyl radical linked via an oxygen atom.

Alkoxyalkyl is an alkoxy radical linked via an alkyl group, and alkoxyalkoxy means an alkoxyalkyl radical linked via an oxygen atom, for example, but not limited to, methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.

Alkylthioalkyl is an alkylthio radical linked via an alkyl group, and alkylthioalkylthio means an alkylthioalkyl radical linked via an oxygen atom.

Arylalkoxyalkyl is an aryloxy radical linked via an alkyl group, and heteroaryloxyalkyl means a heteroaryloxy radical linked via an alkyl group.

Haloalkoxyalkyl is a linked haloalkoxy radical, and haloalkylthioalkyl means a haloalkylthio radical linked via an alkyl group.

Arylalkyl is an aryl radical linked via an alkyl group, heteroarylalkyl means a heteroaryl radical linked via an alkyl group, and heterocyclylalkyl means a heterocyclyl radical linked via an alkyl group.

Cycloalkylalkyl is a cycloalkyl radical linked via an alkyl group, for example (without limitation), cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3 -cyclopropylprop-1 -yl.

Arylalkenyl is an aryl radical linked via an alkenyl group, heteroarylalkenyl is a heteroaryl radical linked via an alkenyl group, and heterocyclylalkenyl is a heterocyclyl radical linked via an alkenyl group.

Arylalkynyl is an aryl radical linked via an alkynyl group, heteroarylalkynyl is a heteroaryl radical linked via an alkynyl group, and heterocyclylalkynyl is a heterocyclyl radical linked via an alkynyl group.

In accordance with the present invention, a haloalkylthio, alone or as part of a chemical group, is a straight or branched S-haloalkyl, preferably containing 1-8 or containing 1-6 carbon atoms, such as (C ₁ -C ₈ )-, ( C ₁ -C ₆ )- or (C1C ₄ ) haloalkylthio, for example (without limitation), trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3, 3,3-prop-1-ylthio.

Halocycloalkyl and halocycloalkenyl are cycloalkyl or cycloalkenyl partially or wholly substituted with identical or different halogen atoms, e.g. F, Cl and Br, or haloalkyl, e.g. trifluoromethyl or difluoromethyl, e.g. 1-fluorocycloprop-1-yl, 2fluorocycloprop-1-yl , 2,2-difluorocycloprop-1-yl, 1-fluorocyclobut-1-yl, 1-trifluoromethylcycloprop-1-yl, 2-trifluoromethylcycloprop-1-yl, 1-chlorocycloprop-1-yl, 2-chlorocycloprop-1-yl , 2,2-dichlorocycloprop-1yl, 3,3-difluorocyclobutyl.

In accordance with the present invention, a trialkylsilyl, alone or as part of a chemical group, is a straight or branched Si-alkyl, preferably containing 1-8 or containing 1-6 carbon atoms, such as tri-[(C1-C ₈ )- _{. _} silyl, tri(1-methylprop-1-yl)silyl, tri-(2-methylprop-1-yl)silyl, tri(1,1-dimethylethyl-1yl)silyl, tri(2,2-dimethylethyl-1-yl) )silyl.

Trialkylsilylalkynyl is a trialkylsilyl radical linked via an alkynyl group.

Synthesis of substituted thiophenyluracils of general formula (I)

Substituted thiophenyluracils of general formula (I) according to the present invention can be obtained using known methods. Synthetic routes used and contemplated are carried out using commercially available or easily obtained heteroaromatic amines and suitably substituted hydroxyesters. The Q, W, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ¹⁴ moieties in the general formula (I) in the Schemes below have the meanings defined above, but only if illustrative and not restrictive definitions are given. . The first key intermediate that is obtained

- 25 042989 for the synthesis of compounds of general formula (I) in accordance with the present invention, is an optionally additionally substituted mercaptophenyl-1H-pyrimidine-2,4-dione. As an example, and not limitation, this is shown for the synthesis of 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl-6trifluoromethyl-1H-pyrimidine-2,4-dione (IIa) (Scheme 1) . For this purpose, a suitable substituted aniline, 2-fluoro-4-chloroaniline by way of example and not limitation, is converted to the corresponding isocyanate with an appropriate reagent (e.g. triphosgene) in a suitable polar aprotic solvent (e.g. dichloromethane) and the isocyanate is converted to next step by reaction with a suitable aminoacrylic ester using a suitable base (eg sodium hydride or potassium t-butoxide) in a suitable polar aprotic solvent (eg N,N-dimethylformamide) to the corresponding optionally further substituted pyrimidine-2,4 -dione, by way of example, and not limitation, 3-(4-chloro-2-fluorophenyl)-1-methyl-6trifluoromethyl-1H-pyrimidine-2,4-dione (Scheme 1).

By subsequent sulfochlorination with a suitable reagent (e.g. chlorosulfonic acid) followed by reduction with a suitable reducing agent (e.g. Zn in EtOH and HCl, tin(II) chloride hydrate or triphenylphosphine), the desired further substituted mercaptophenyl-1H-pyrimidine- 2,4-dione, by way of example and not limitation, 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (IIa) (see KR 1345394; EP 1122244; EP 408382; WO 2003/029226; WO 2010/038953; US 2011/0224083; KR 2011/110420).

In Scheme 1 below, W by way of example and not limitation is O, R by way of example and not limitation is CH ₃ , R ² by way of example and not limitation is hydrogen, R ³ by way of example , and not limitation, is fluorine, R ⁴ by way of example, and not limitation, is chlorine, and R ¹⁴ by way of example, and not limitation, is fluorine.

Scheme 1

(Ila)

The synthesis of the key intermediate (IIa) described in Scheme 1 can also be used to prepare similar intermediates, e.g. -2,4-dione (IIb). In Scheme 2 below, R ¹ by way of example and not limitation is CH3, R ² by way of example and not limitation is methyl, R ³ by way of example and not limitation is fluorine, R ⁴ as example, and not limitation, is chlorine, and R ¹⁴ by way of example, and not limitation, is fluorine.

Scheme 2

The synthesis of the key intermediate (IIa) described in Scheme 1 can be further applied to the preparation of intermediates in which the R ¹ group is an amino group, for example 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1,5 -dimethyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (IIc). A suitable phthalimide is used in this case as a protecting group for the amino group. In Scheme 3 below, R ¹ by way of example and not limitation is NH2, R ² by way of example and not limitation is hydrogen, R ³ by way of example and not limitation is fluorine, R ⁴ as example, and not limitation, is chlorine, and R ¹⁴ by way of example, and not limitation, is fluorine.

Scheme 3

(Нс|

The considered intermediate, additionally substituted 5-mercaptophenyl-1H-pyrimidine2,4-diones (II) can then be converted into the necessary compounds of general formula (I) in accordance with the present invention using two different routes (Scheme 4): (i) by the reaction with a suitable, optionally further substituted 2-haloacetic acid ester (III) using a suitable base (e.g. potassium carbonate, cesium carbonate or sodium carbonate) in a suitable polar aprotic solvent, or (ii) by reacting intermediates (II) with a suitable , optionally further substituted with 2-haloacetic acid to give the corresponding thioacetic acid intermediate (IV) using a suitable base (e.g. potassium carbonate, cesium carbonate) and then reacting the corresponding intermediate (IV) with a suitable, optionally further substituted hydroxyester using suitable coupling reagents (e.g. HOBt=1-hydroxybenzotriazole, EDC=1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, HATU=O-(7-azabenzotriazol-1-yl)-N, N,N',N'-tetramethyluronium hexafluorophosphate, T3P=2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinan-2,4,6-trioxide) and suitable bases (e.g. diisopropylethylamine , triethylamine) in a suitable polar aprotic solvent (eg dichloromethane, chloroform). In Scheme 4 below, R ² and R ⁶ , by way of example, and not limitation, are hydrogen, and Q, by way of example, and not limitation, are fragments Q-2 and Q-42.

Scheme 4

Selected detailed synthesis examples for the compounds of general formula (I) according to the present invention are given below. The example numbers given correspond to the numbering given in Tables I.1-I.50 below. 1H NMR, ¹³ C NMR and ¹⁹ F NMR spectroscopy data given for the chemical examples described in the following paragraphs (400 MHz for 1H NMR, and 150 MHz for ¹³ C NMR, and 375 MHz for ¹⁹ F NMR , solvent: CDCl ₃ , CD3OD or d ₆ -DMSO, internal standard: tetramethylsilane δ = 0.00 ppm) was obtained with a Bruker instrument and the determined signals have the following definitions: br = wide; s = singlet, d = doublet, t = triplet, dd = doublet of doublets, ddd = doublet of doublet of doublets, m = multiplet, q = quartet, fifth. = quintet, sixth. = sextet, sept. = septet, dq = doublet of quartets, dt = doublet of triplets. In the case of mixtures of diastereomers, either the corresponding significant signals for both diastereomers or the characteristic signal of the main diastereomer are given. The abbreviations used for chemical groups have the following meanings, for example, Me \u003d CH ₃ , Et \u003d CH ₂ CH ₃ , t-Hex \u003d C (CH ₃ ) ₂ CH (CH ₃ ) ₂ , t-Bu \u003d C (CH ₃ ) ₃ , n-Bu = straight butyl, nPr = straight propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl.

Synthesis Examples No. I.2-3. 3-Ethoxy-3-oxopropyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6dihydropyrimidin-1(2H)-yl] phenyl}sulfanyl)butanoate

- 27 042989

2-fluoro-4-chloroaniline (145 g, 996 mmol) and triethylamine (202 g, 2000 mmol) were carefully added sequentially to a solution of triphosgene (119 g, 401 mmol) in abs. dichloromethane (1000 ml) so that the temperature of the resulting reaction mixture remained below 20°C. After completion of the addition, the reaction mixture was stirred at room temperature overnight and then washed with water (3x500 ml) and 1N. hydrochloric acid (500 ml), dried over sodium sulfate, filtered and concentrated under reduced pressure. The 2-fluoro-4-chlorophenylisocyanate thus obtained was used in the next step without further purification. Sodium hydride (5.60 g, 140 mmol, 60% dispersion in mineral oil) was suspended in abs. N,N-dimethylformamide and ethyl-(2E)-3-amino-4,4,4-trifluorobut-2-enoate (14.2 g, 77.5 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour, then cooled to 30° C. and 2-fluoro-4-chlorophenylisocyanate (12.0 g, 70.0 mmol) was added.

Upon completion of the addition, the resulting reaction mixture was stirred at room temperature for an additional 4 hours and then added to ice water. After adding ethyl acetate and acidifying with 1 N. hydrochloric acid, the aqueous phase was thoroughly extracted with ethyl acetate.

The combined organic phases were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. 3-(4-Chloro-2-fluorophenyl)6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (15.2 g, 50.2 mmol, 65%) was obtained in this way, which was used in the next step without further purification. It was also possible to successfully repeat this reaction step on a larger scale. To a solution of 3-(4-chloro-2-fluorophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)dione (238 g, 770 mmol) in abs. N,N-dimethylformamide (800 ml) was added potassium carbonate (117 g, 850 mmol).

After that, a solution of methyl iodide (120 g, 850 mmol) in abs. Ν,N-dimethylformamide (100 ml) and the resulting reaction mixture was stirred at room temperature for an additional 1 hour. After the conversion was completed, the reaction mixture was cooled to a temperature of 0°C, water (2000 ml) was carefully added, and then the mixture was thoroughly extracted with dichloromethane .

The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. In this way, 3-(4-chloro-2-fluorophenyl)-1-methyl-6(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (241 g, 747 mmol, 97% of theory) was obtained, which was converted in the next step without further purification. 3-(4-Chloro-2-fluorophenyl)-1-methyl-6(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (100 g, 310 mmol) was then gradually added to chlorosulfonic acid in a heated round bottom flask. The resulting reaction mixture was then stirred at 110° C. for 20 h and, after cooling to room temperature, added to ice water and extracted several times with ethyl acetate (3x300 ml).

The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. This provided 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]benzenesulfonyl chloride (75.0 g, 178 mmol, 57% of theory), which was used in the next step without further purification.

To the initial load in the form of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6dihydropyrimidin-1(2H)-yl]sulfonyl chloride (100.0 g, 237 mmol) in a round bottom flask were added successively hydrochloric acid (500 ml), acetic acid (500 ml) and tin dichloride dihydrate (270 g, 1197 mmol). The resulting reaction mixture was stirred at a temperature of 100°C for 10 h, after cooling to room temperature was added to ice water and carefully extracted with dichloromethane (3x400 ml).

The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. Final purification by column chromatography provided 3-(4-chloro-2-fluoro-5-sulfanylphenyl)-1-methyl-6-(trifluoromethyl)pyrimidine2,4(1H,3H)-dione (73.0 g, 206 mmol , 83% of theory) as a colorless solid. 2Chlorobutanecarboxylic acid (691 mg, 5.64 mmol) was dissolved in abs. acetonitrile under argon in a heated round bottom flask and then cesium carbonate (3.67 g, 11.28 mmol) and 3-(4-chloro-2fluoro-5-sulfanylphenyl)-1-methyl-6-(trifluoromethyl)pyrimidine- 2,4(1H,3H)-dione (2.0 g, 5.64 mmol).

The resulting reaction mixture was stirred at 50° C. for 1 hour and, after cooling to room temperature, mixed with water and dichloromethane and thoroughly extracted. The aqueous phase was then acidified with 10% hydrochloric acid and extracted again several times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give 2-({2-chloro-4fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine- 1(2H)-yl]phenyl}sulfanyl)buta

- 28 042989 new acid (2.0 g, 80% of theory) as a colorless solid.

'H-NMR (CDCl ₃ δ, ppm) 7.53 (d, 1H), 7.38 (d, 1H), 6.36 (d, 1H), 3.68 (m, 1H), 3.55 (s, 3H), 2.05-1.95 (m, 1H), 1.93-1.82 (m, 1H), 1.09 (t, 3H).

2-({2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoic acid (100 mg, 0.23 mmol), 1-hydroxy-1H-benzotriazole (40 mg, 0.29 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (57 mg, 0.29 mmol) were dissolved in abs. dichloromethane in a heated round bottom flask under argon and after stirring at room temperature for 5 minutes, ethyl 3-hydroxypropanoate (35 mg, 0.29 mmol) and triethylamine (0.08 ml, 0.57 mmol) were added. The resulting reaction mixture was stirred at room temperature for 6 hours, then mixed with water and dichloromethane and thoroughly extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure.

The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give 3-ethoxy-3-oxopropyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4- (trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoate (44 mg, 36% of theory) as a high viscosity colorless oil.

¹ H-NMR (CDCI3 δ, ppm) 7.53 (m, 1H), 7.36 (m, 1H), 6.35 (d, 1H), 4.36-4.27 (m, 2H), 4.17-4.10 (m, 2H), 3.71-3.64 (m, 1H), 3.55 (s, 3H), 2.59-2.52 (m, 2H), 2, 02-1.91 (m, 1H), 1.89-1.80 (m, 1H), 1.24 (t, 3H), 1.05 (t, 3H).

No. I.2-43. 2-Ethoxy-2-oxoethyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6dihydropyrimidin-1(2H)-yl] phenyl}sulfanyl)butanoate

2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-'(2H)-yl]phenyl}sulfanyl)butanoic acid (100 mg, 0.23 mmol), 1-hydroxy-1H-benzotriazole (40 mg, 0.29 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (57 mg, 0.29 mmol) were dissolved in abs. dichloromethane in a heated round bottom flask under argon and after stirring at room temperature for 5 minutes, ethyl hydroxyacetate (31 mg, 0.29 mmol) and triethylamine (0.08 ml, 0.57 mmol) were added. The resulting reaction mixture was stirred at room temperature for 6 hours, then mixed with water and dichloromethane and thoroughly extracted with dichloromethane.

The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give 2-ethoxy-2-oxoethyl-2-({2-chloro-4-fluoro-5-[3-methyl2,6-dioxo-4-(trifluoromethyl )-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoate (60 mg, 50% of theory) as a high viscosity colorless oil.

'h-NMR (CDCl3 δ, ppm) 7.58 (m, 1H), 7.36 (m, 1H), 6.34 (m, 1H), 4.63-4.53 (m, 2H), 4.19-4.12 (m, 2H), 3.77-3.72 (m, 1H), 3.55 (s, 3H), 2.09-1.99 (m, 1H), 1, 93-1.84 (m, 1H), 1.25 (t, 3H), '.12 (t, 3H).

No. I.2-145. (5-oxotetrahydrofuran-2-yl)methyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4(trifluoromethyl)-3,6-dihydropyrimidine-1(2Н )-yl]phenyl}sulfanyl)butanoate

2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoic acid (90 mg, 0.20 mmol), '-hydroxy-1H-benzotriazole (36 mg, 0.27 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (51 mg, 0.27 mmol) were dissolved in abs. dichloromethane in a heated round bottom flask under argon and after stirring at room temperature for 5 minutes, 5-(hydroxymethyl)dihydrofuran-2(3H)-one (31 mg, 0.27 mmol) and triethylamine (0.08 ml, 0 .57 mmol). The resulting reaction mixture was stirred at room temperature for 2 hours, then mixed with water and dichloromethane and thoroughly extracted with dichloromethane.

The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give (5-oxotetrahydrofuran-2-yl)methyl-2-({2-chloro-4fluoro-5-[3-methyl-2,6-dioxo-4 -(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoate (73 mg, 66% of theory) as a high viscosity colorless oil.

'H-NMR (CDCI3 δ, ppm) 7.54 (m, 'H), 7.38 (m, 1H), 6.33 (m, 1H), 4.64-4.57 (m, 'H ), 4.29-4.2' (m, 'H), 4.10-4.04 (m, 'H), 3.82-3.76 (m, 1H), 3.56 (s, 3H), 2.58-2.48 (m, 2H), 2.33-2.20 (m, 'H), 2.06-1.97 (m, 1H), 1.93-1.78 (m, 2H), '.11-1.06 (1H, 3n).

No. I.4-3. 3-Ethoxy-3-oxopropyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6dihydropyrimidin-1(2H)-yl] phenyl} sulfanyl)-4-methylpentanoate

- 29 042989 _f ^f ^nA ₀ a

2-chloro-4-methylpentanecarboxylic acid (849 mg, 5.64 mmol) was dissolved in abs. acetonitrile under argon in a heated round bottom flask and then cesium carbonate (3.67 g, 11.28 mmol) and 3-(4-chloro-2-fluoro-5-sulfanylphenyl)-1-methyl-6-(trifluoromethyl) were added pyrimidine-2,4(1H,3H)-dione (2.0 g, 5.64 mmol). The resulting reaction mixture was stirred at 50° C. for 1 hour and, after cooling to room temperature, mixed with water and dichloromethane and thoroughly extracted. The aqueous phase was then acidified with 10% hydrochloric acid and extracted again several times with dichloromethane.

The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4(trifluoromethyl)-3,6-dihydropyrimidine -1(2H)-yl]phenyl}sulfanyl)-4-methylpentanoic acid (1.62 g, 61% of theory) as a colorless solid.

¹ H-NMR (CDCl3 δ, ppm) 7.53 (d, 1H), 7.37 (d, 1H), 6.37 (m, 1H), 3.82-3.78 (m, 1H), 3.55 (s, 3H), 1.901.78 (m, 2H), 1.73-1.65 (m, 1H), 0.99-0.92 (m, 6H).

2-({2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-4 -methylpentanoic acid (100 mg, 0.21 mmol), 1-hydroxy-III-benzotriazole (38 mg, 0.28 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (53 mg, 0.28 mmol ) was dissolved in abs. dichloromethane in a heated round bottom flask under argon and, after stirring at room temperature for 5 minutes, ethyl 3-hydroxypropanoate (33 mg, 0.28 mmol) and triethylamine (0.07 ml, 0.51 mmol) were added. The resulting reaction mixture was stirred at room temperature for 6 hours, then mixed with water and dichloromethane and thoroughly extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give 3-ethoxy-3-oxopropyl-2-({2-chloro-4fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl )-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-4methylpentanoate (43 mg, 35% of theory) as a high viscosity colorless oil.

¹ H-NMR (CDCl3 δ, ppm) 7.47 (m, 1H), 7.35 (m, 1H), 6.35 (d, 1H), 4.37-4.30 (m, 1H), 4.28-4.22 (m, 1H), 4.14-4.09 (q, 2H), 3.84-3.80 (m, 1H), 3.55 (s, 3H), 2, 58-2.51 (m, 2H), 1.89-1.83 (m, 1H), 1.80-1.72 (m, 1H), 1.69-1.62 (m, 1H), 1.25 (t, 3H), 0.94 (d, 3H), 0.92 (d, 3H).

No. I.6-3. 3-Ethoxy-3-oxopropyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6dihydropyrimidin-1(2H)-yl] phenyl}sulfanyl)-3-methylbutanoate

2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-3 -methylbutanoic acid (100 mg, 0.22 mmol), 1-hydroxy-III-benzotriazole (39 mg, 0.29 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (55 mg, 0.29 mmol ) was dissolved in abs. dichloromethane in a heated round bottom flask under argon and after stirring at room temperature for 5 minutes, ethyl 3-hydroxypropanoate (34 mg, 0.29 mmol) and triethylamine (0.07 ml, 0.53 mmol) were added.

The resulting reaction mixture was stirred at room temperature for 6 hours, then mixed with water and dichloromethane and thoroughly extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give 3-ethoxy-3-oxopropyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4( trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-3-methylbutanoate (45 mg, 37% of theory) as a high viscosity colorless oil.

¹ H-NMR (CDCl ₃ δ, ppm) 7.45 (m, 1H), 7.34 (m, 1H), 6.35 (m, 1H), 4.37-4.23 (m, 2H) , 4.15-4.09 (m, 2H), 3.55 (s, 3H), 3.52 (m, 1H), 2.58-2.54 (m, 2H), 2.24-2 .16 (m, 1H), 1.19 (t, 3H), 1.07 (t, 3H).

No. I.6-43. 2-Ethoxy-2-oxoethyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6dihydropyrimidin-1(2H)-yl] phenyl}sulfanyl)-3-methylbutanoate

2-chloro-3-methylbutanecarboxylic acid (770 mg, 5.64 mmol) was dissolved in abs. acetonitrile in an argon atmosphere in a heated round bottom flask and then cesium carbonate (3.67 g, 11.28 mmol) was added and

3-(4-chloro-2-fluoro-5-sulfanylphenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (2.0 g, 5.64 mmol). The resulting reaction mixture was stirred at a temperature of 50° C. for one hour and, after cooling to room temperature, mixed with water and dichloromethane and thoroughly extracted.

The aqueous phase was then acidified with 10% hydrochloric acid and extracted again several times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give 2-({2-chloro-4-fluoro-5[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine -1(2H)-yl]phenyl}sulfanyl)-3methylbutanoic acid (0.47 g, 21% of theory) as a colorless solid.

¹ H-NMR (CDCl3 δ, ppm) 7.49 (d, 1H), 7.37 (d, 1H), 6.33 (m, 1H), 3.58-3.48 (m, 1H), 3.53 (s, 3H), 2.252.17 (m, 1H), 1.18 (d, 3H), 1.11 (d, 3H), 2-({2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-3-methylbutanoic acid (100mg, 0.22mmol), 1hydroxy-1H -benzotriazole (39 mg, 0.29 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (55 mg, 0.29 mmol) were dissolved in abs. dichloromethane in a heated round bottom flask under argon and after stirring at room temperature for 5 minutes, ethyl 3-hydroxyacetate (30 mg, 0.29 mmol) and triethylamine (0.07 ml, 0.53 mmol) were added.

The resulting reaction mixture was stirred at room temperature for 6 hours, then mixed with water and dichloromethane and thoroughly extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give 2-ethoxy-2-oxoethyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4- (trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-3-methylbutanoate (54 mg, 45% of theory) as a high viscosity colorless oil.

¹ H-NMR (CDCl ₃ δ, ppm) 7.56 (m, 1H), 7.36 (m, 1H), 6.34 (m, 1H), 4.60-4.50 (m, 2H) , 4.17-4.12(m, 1H), 3.64-3.58(m, 1H), 3.54(s, 3H), 2.32-2.24(m, 1H), 1 .26 (t, 3H), 1.20 (d, 3H), 1.16 (d, 3H).

No. I.44-3. Ethyl 3-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl }sulfanyl)(cyclopropyl)acetoxy]propanoate

Ethyl chloro(cyclopropyl)acetate (409 mg, 1.97 mmol) was dissolved in abs. acetonitrile under argon in a heated round bottom flask and then cesium carbonate (273 mg, 1.97 mmol) and 3-(4chloro-2-fluoro-5-sulfanylphenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2, 4(1H,3H)-dione (700 mg, 1.97 mmol). The resulting reaction mixture was stirred at 50° C. for 2 hours and, after cooling to room temperature, mixed with water and dichloromethane and thoroughly extracted. The aqueous phase was then acidified with 10% hydrochloric acid and extracted again several times with dichloromethane.

The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure.

The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give ethyl-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6dihydropyrimidine- 1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetate (940 mg, 99% of theory) as a colorless solid.

¹ H-NMR (CDCl3 δ, ppm) 7.51 (d, 1H), 7.35 (d, 1H), 6.34 (s, 1H), 4.18-4.05 (m, 2H), 3.53 (s, 3H), 3.133.10 (m, 1H), 1.33-1.26 (m, 1H), 1.15 (t, 3H), 0.75-0.66 (m, 2H), 0.48-0.44 (m, 1H), 0.42-0.36 (m, 1H).

Ethyl-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)yl]phenyl}sulfanyl)(cyclopropyl) acetate (160 mg, 0.33 mmol) was then dissolved in ethyl acetate and 6N hydrochloric acid was added. HCl. The resulting reaction mixture was stirred at a temperature of 100° C. for 3 hours, after cooling to room temperature, mixed with water and thoroughly extracted with abs. dichloromethane.

The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give ({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4(trifluoromethyl)-3,6-dihydropyrimidine-1 (2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetic acid (120 mg, 79% of theory) as a colorless solid.

1H-NMR (CDCl3 δ, ppm) 7.54 (dd, 1H), 7.36 (d, 1H), 6.34 (m, 1H), 3.55 (s, 3H), 3.11-3 .08 (m, 1H), 1.321.24 (m, 1H), 0.77-0.69 (m, 2H), 0.52-0.38 (m, 2H), ({2-chloro-4 -fluoro-5-[3-methyl-2,6-dioxo-4(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetic acid

- 31 042989 (120 mg, 0.27 mmol), 1-hydroxy-1H-benzotriazole (47 mg, 0.35 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (66 mg, 0.35 mmol) were dissolved in abs. dichloromethane in a heated round bottom flask under argon and, after stirring at room temperature for 5 minutes, ethyl 3-hydroxypropionate (41 mg, 0.35 mmol) and triethylamine (0.09 ml, 0.64 mmol) were added.

The resulting reaction mixture was stirred at room temperature for 2 hours, then mixed with water and dichloromethane and thoroughly extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure.

The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give ethyl 3-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl) -3,6dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetoxy]propanoate (81 mg, 54% of theory) as a high viscosity colorless oil.

¹ H-NMR (d ₆ -DMSO δ, ppm) 7.83 (d, 1H), 7.68 (m, 1H), 6.62 (m, 1H), 4.27-4.18 (m, 1H), 4.17-4.10 (m, 1H), 4.07-3.98 (m, 2H), 3.52-3.48 (m, 1H), 3.41 (s, 3H) , 2.71-2.58 (m, 2H) 1.23-1.11 (m, 4H), 0.72-0.56 (m, 2H), 0.49-0.34 (m, 2H ).

No. I.44-6. Benzyl-3-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl } sulfanyl)(cyclopropyl)acetoxy]propanoate

({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetic acid (120 mg, 0.27 mmol), 1-hydroxy-1H-benzotriazole (47 mg, 0.35 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (66 mg, 0.35 mmol) were dissolved in abs. dichloromethane in a heated round bottom flask under argon and after stirring at room temperature for 5 minutes, benzyl 3-hydroxypropionate (62 mg, 0.35 mmol) and triethylamine (0.09 ml, 0.64 mmol) were added.

The resulting reaction mixture was stirred at room temperature for 2 hours, then mixed with water and dichloromethane and thoroughly extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give benzyl-3-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl) -3,6dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)-acetoxy]propanoate (76 mg, 45% of theory) as a high viscosity colorless oil.

¹ H-NMR (d6-DMSO δ, ppm) 7.83 (d, 1H), 7.67 (m, 1H), 6.60 (m, 1H), 5.09 (s, 2H), 4, 30-4.23 (m, 1H), 4.21-4.15 (m, 1H), 3.41 (s, 3H), 3.39-3.31 (m, 1H), 2.72- 2.57 (m, 2H), 1.18-1.09 (m, 1H), 0.68-0.53 (m, 2H), 0.40-0.34 (m, 2H).

No. I.48-2. 3-Methoxy-3-oxopropyl-2-({2-chloro-5-[5-ethyl-3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6dihydropyrimidin-1(2H)-yl] -4-fluorophenyl}sulfanyl)propanoate

Similarly to the synthesis of example No. I.12-72, a solution of n-butyllithium in hexane was added to a solution of diisopropylamine cooled to -10°C in abs. tetrahydrofuran. The resulting reaction mixture was stirred at -10°C for 40 minutes and then further cooled to -78°C. Ethyl butanoate was then carefully added. The reaction mixture was stirred at -78° C. for 1 hour, an appropriate amount of 2,2,2-trifluoroethyltrifluoroacetate was added and finally the mixture was stirred at room temperature overnight. Upon completion of the transformation, the mixture was acidified with dil. hydrochloric acid (1 M) and thoroughly extracted several times with ethyl acetate.

These combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure and the ethyl 4,4,4-trifluoro-2-ethyl-3oxobutanoate thus obtained (67% of theory) was dissolved in toluene in a round bottom flask without further purification and mixed with ammonium acetate and acetic acid.

The resulting reaction mixture was stirred under reflux conditions using a water separator for several hours until no more water was separated. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, and then the residue was taken up in ethyl acetate and water.

The aqueous phase was then thoroughly extracted with ethyl acetate and the combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. Distillation purification of the resulting residue provided ethyl-(22)-3-amino-4,4,4-trifluoro-2-32 042989 ethylbut-2-enoate (58% of theory). 2-Fluoro-4-chloroaniline and triethylamine were carefully added sequentially to a solution of triphosgene in abs. dichloromethane so that the temperature of the resulting reaction mixture remained below 20°C.

After the addition was complete, the reaction mixture was stirred at room temperature overnight and then washed with water and 1N hydrochloric acid, dried over sodium sulfate, filtered and concentrated under reduced pressure. The 2-fluoro4-chlorophenylisocyanate thus obtained was used in the next step without further purification. Sodium hydride (60% dispersion in mineral oil) was suspended in abs. K,K-dimethylformamide and ethyl (2Z)-3-amino-4,4,4-trifluoro-2-ethylbut-2-enoate was added.

The reaction mixture was stirred at room temperature for 1 hour, then cooled to -30° C. and 2-fluoro-4-chlorophenylisocyanate was added. Upon completion of the addition, the resulting reaction mixture was stirred at room temperature for an additional 4 hours and then added to ice water. After adding ethyl acetate and acidifying with 1 N. hydrochloric acid, the aqueous phase was thoroughly extracted with ethyl acetate.

The combined organic phases were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. In this way, 3-(4-chloro-2-fluorophenyl)5-ethyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (66%) was obtained, which was used in the next step without further purification. To a solution of 3-(4-chloro-2-fluorophenyl)-5-methyl-6-(trifluoromethyl)pyrimidine2,4(1H,3H)-dione (1 eq.) in abs. Potassium carbonate (1.2 eq.) was added to N,N-dimethylformαmide.

After that, a solution of methyl iodide (1.2 eq.) was added in abs. K,K-dimethylformamide and the resulting reaction mixture were stirred at room temperature for an additional 1 hour. After the conversion was complete, the reaction mixture was cooled to a temperature of 0° C., water was carefully added, and then the mixture was thoroughly extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. In this way, 3-(4-chloro-2-fluorophenyl)-5-ethyl-1-methyl-6-(trifluoromethyl)pyrimidine2,4(1H,3H)-dione (97% of theory) was obtained, which was converted in the next step without additional cleaning. 3-(4-Chloro-2-fluorophenyl)-5-ethyl-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione was then gradually added to chlorosulfonic acid in a heated round bottom flask.

The resulting reaction mixture was then stirred at 110° C. for 20 hours and, after cooling to room temperature, added to ice-water and extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. This provided 2-chloro-4-fluoro5-[5-ethyl-3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]benzenesulfonyl chloride (54% of theoretical), which was used in the next step without further purification.

To the initial load in the form of 2-chloro-4-fluoro-5-[5-ethyl-3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6dihydropyrimidin-1(2H)-yl]sulfonyl chloride (1 eq.) in a round bottom flask were added successively hydrochloric acid (2 ml/mmol), acetic acid (2.5 ml/mmol) and tin dichloride dihydrate (3 eq.). The resulting reaction mixture was stirred at a temperature of 100° C. for 10 hours, after cooling to room temperature, added to ice-water and thoroughly extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure.

Final purification by column chromatography provided 3-(4-chloro-2fluoro-5-sulfanylphenyl)-5-ethyl-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (84% of theoretical) as a colorless solid. 2-Chloropropanecarboxylic acid (567 mg, 5.23 mmol) was dissolved in abs. acetonitrile under argon in a heated round bottom flask and then cesium carbonate (3.41 g, 10.45 mmol) and 3-(4-chloro-2-fluoro-5-sulfanylphenyl)-5-ethyl-1-methyl-6 (trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (2.0 g, 5.23 mmol).

The resulting reaction mixture was stirred at 50° C. for 1 hour and, after cooling to room temperature, mixed with water and dichloromethane and thoroughly extracted. The aqueous phase was then acidified with 10% hydrochloric acid and extracted again several times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure.

The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give 2-({2-chloro-5-[5-ethyl-3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6dihydropyrimidine- 1(2H)-yl]-4-fluorophenyl}sulfanyl)propanoic acid (1.30 g, 54% of theory) as a colorless solid.

¹ H-NMR (CDCl ₃ δ, ppm) 7.54 (d, 1H), 7.39 (d, 1H), 3.90-3.83 (m, 1H), 3.54 (s, 3H) , 2.72-2.69 (m, 2H), 1.55 (d, 3H), 1.13 (t, 3H), 2-({2-chloro-5-[5-ethyl-3-methyl -2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-4-fluorophenyl}sulfanyl)propanoic acid (110mg, 0.24mmol), 1hydroxy-1H-benzotriazole (42 mg, 0.31 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (60 mg, 0.31 mmol) were dissolved in abs. dichloromethane in a heated round-bottom flask in the atmosphere

- 33042989 argon and after stirring at room temperature for 5 minutes, methyl 3-hydroxypropanoate (33 mg, 0.31 mmol) and triethylamine (0.08 ml, 0.61 mmol) were added.

The resulting reaction mixture was stirred at room temperature for 6 hours, then mixed with water and dichloromethane and thoroughly extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography (ethyl acetate/heptane gradient) to give 3-methoxy-3-oxopropyl-2-({2-chloro-5-[5-ethyl-3-methyl-2,6-dioxo-4( trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-4-fluorophenyl}sulfanyl)propanoate (61 mg, 45% of theory) as a high viscosity colorless oil.

¹ H-NMR (CDCI3 δ, ppm) 7.49 (d, 1H), 7.37 (d, 1H), 4.37-4.25 (m, 2H), 3.92-3.87 (m , 1H), 3.67 (s, 3H), 3.54 (s, 3H), 2.74-2.68 (m, 2H), 2.60-2.53 (m, 2H), 1, 51 (t, 3H), 1.12 (t, 3H).

By analogy with the above production examples, which were indicated in the corresponding paragraph, and taking into account the general details of the preparation of substituted thiophenyluracils, the compounds indicated below were obtained. If the structural element in the table. 1 is defined by a structural formula containing a dotted line, this dotted line means that the group in question is attached to the rest of the molecule at that position. If the structural element in the table. 1 is defined by a structural formula containing an arrow, the arrow represents the bond of the corresponding Q group to the carbonyl group in the general formula (I).

Tab. 1.1. Preferred compounds of formula (I.1) are compounds I.1-1-I.1300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.1-1-I.1-300 from table. I.1 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

- 34 042989

9 Q-9 10 Q-10 AND Q-ll 12 Q-12 13 Q-13 14 Q-14 15 Q-15 16 Q-16 17 Q-17 18 Q-18 19 Q-19 20 Q-20 21 Q-21 22 Q-22 23 Q-23 24 Q-24 25 Q-25 26 Q-26 27 Q-27 28 Q-28 29 Q-29 thirty Q-30 31 Q-31 32 Q-32 33 Q-33 34 Q-34 35 Q-35 36 Q-36 37 Q-37 38 Q-38 39 Q-39

- 35 042989

- 36 042989

- 37 042989

164 Q-164 165 Q-165 166 Q-166 167 Q-167 168 Q-168 169 Q-169 170 Q-170 171 Q-171 172 Q-172 173 Q-173 174 Q-174 175 Q-175 176 Q-176 177 Q-177 178 Q-178 179 Q-179 180 Q-180 181 Q-181 182 Q-182 183 Q-183 184 Q-184 185 Q-185 186 Q-186 187 Q-187 188 Q-188 189 Q-189 190 Q-190 191 Q-191 192 Q-192 193 Q-193 194 Q-194

-38042989

- 39 042989

257 Q-257 258 Q-258 259 Q-259 260 Q-260 261 Q-261 262 Q-262 263 Q-263 264 Q-264 265 Q-265 266 Q-266 267 Q-267 268 Q-268 269 Q-269 270 Q-270 271 Q-271 272 Q-272 273 Q-273 274 Q-274 275 Q-275 276 Q-276 277 Q-277 27S Q-278 279 Q-279 280 Q-280 281 Q-281 282 Q-282 283 Q-283 284 Q-284 285 Q-285 286 Q-286 287 Q-287 288 Q-288 289 Q-289 290 Q-290 291 Q-291 292 Q-292 293 Q-293 294 Q-294 295 Q-295 296 Q-296 297 Q-297 298 Q-298 299 Q-299 300 Q-300

Tab. 1.2. Preferred compounds of formula (1.2) are compounds 1.2-1-1.2300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds 1.2-1-1.2-300 from table. 1.2 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. 1.3. Preferred compounds of formula (1.3) are compounds 1.3-1-1.3-40042989

300, in which Q has the definitions of the table. 1, which are given in the corresponding line. Compounds I.3-1-I.3-300 from table. I.3 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.4. Preferred compounds of formula (I.4) are compounds I.4-1-I.4300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.4-1-I.4-300 from table. I.4 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Q(1.5)

Tab. I.5. Preferred compounds of formula (I.5) are compounds I.5-1-I.5300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.5-1-I.5-300 from table. I.5 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.6)

Tab. I.6. Preferred compounds of formula (I.6) are compounds I.6-1-I.6300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.6-1-I.6-300 from table. I.6 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

,Q (1.7)

Tab. I.7. Preferred compounds of formula (I.7) are compounds I.7-1-I.7300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.7-1-I.7-300 from table. I.7 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Q (1.8)

Tab. I.8. Preferred compounds of formula (I.8) are compounds I.8-1-I.8300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.8-1-I.8-300 from table. I.8 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Q (1.9)

Tab. I.9. Preferred compounds of formula (I.9) are compounds I.9-1-I.9300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.9-1-I.9-300 from table. I.9 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (io)

Tab. I.10. Preferred compounds of formula (I.10) are compounds I.10-1I.10-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.10-1-I.10-300 from table. I.10 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

- 41 042989 ,Q (Mi)

Tab. I.11. Preferred compounds of formula (I.11) are compounds I.11-1I.11-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.11-1-I.11-300 from table. I.11 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.12)

Tab. I.12. Preferred compounds of formula (I.12) are compounds I.12-1I.12-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.12-1-I.12-300 from table. I.12 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (of)

Tab. I.13. Preferred compounds of formula (I.13) are compounds I.13-1I.13-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.13-1-I.13-300 from table. I.13 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.14)

Tab. I.14. Preferred compounds of formula (I.14) are compounds I.14-1I.14-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.14-1-I.14-300 from table. I.14 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.15. Preferred compounds of formula (I.15) are compounds I.15-1I.15-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.15-1-I.15-300 from table. I.15 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.16. Preferred compounds of formula (I.16) are compounds I.16-1I.16-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.16-1-I.16-300 from table. I.16 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.17)

Tab. I.17. Preferred compounds of formula (I.17) are compounds I.17-1I.17-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.17-1-I.17-300 from table. I.17 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

,Q (1.18)

- 42 042989

Tab. I.18. Preferred compounds of formula (I.18) are compounds I.18-11.18-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.18-1-I.18-300 from table. I.18 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.19)

Tab. I.19. Preferred compounds of formula (I.19) are compounds I.19-1I.19-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.19-1-I.19-300 from table. I.19 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.20)

Tab. I.20. Preferred compounds of formula (I.20) are compounds I.20-1I.20-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.20-1-I.20-300 from table. I.20 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.21)

Tab. I.21. Preferred compounds of formula (I.21) are compounds I.21-1I.21-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.21-1-I.21-300 from table. I.21 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.22)

Tab. I.22. Preferred compounds of formula (I.22) are compounds I.22-1I.22-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.22-1-I.22-300 from table. I.22 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.23)

Tab. I.23. Preferred compounds of formula (I.23) are compounds I.23-1I.23-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.23-1-I.23-300 from table. I.23 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

,Q (1-24)

Tab. I.24. Preferred compounds of formula (I.24) are compounds I.24-1I.24-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.24-1-I.24-300 from table. I.24 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.25)

Tab. I.25. Preferred compounds of formula (I.25) are compounds I.25-1I.25-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.25-1-I.25-300 from table. I.25 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

- 43 042989

Tab. I.26. Preferred compounds of formula (I.26) are compounds I.26-1I.26-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.26-1-I.26-300 from table. I.26 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

,Q (1.27)

Tab. I.27. Preferred compounds of formula (I.27) are compounds I.27-1I.27-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.27-1-I.27-300 from table. I.27 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.28)

Tab. I.28. Preferred compounds of formula (I.28) are compounds I.28-1I.28-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.28-1-I.28-300 from table. I.28 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

-Q (1.29)

Tab. I.29. Preferred compounds of formula (I.29) are compounds I.29-1I.29-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.29-1-I.29-300 from table. I.29 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.30)

Tab. I.30. Preferred compounds of formula (I.30) are compounds I.30-1I.30-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.30-1-I.30-300 from table. I.30 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

,Q (1.31)

Tab. I.31. Preferred compounds of formula (I.31) are compounds I.31-1I.31-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.31-1-I.31.31-300 from table. I.31 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

-Q (1.32)

Tab. I.32. Preferred compounds of formula (I.32) are compounds I.32-1I.32-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.32-1-I.32-300 from table. I.32 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

,Q (1.33)

Tab. I.33. Preferred compounds of formula (I.33) are compounds I.33-1-44 042989

I.33-300, in which Q has the definitions from Table. 1, which are given in the corresponding line. Compounds I.33-1-I.33-300 from table. I.33 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.34. Preferred compounds of formula (I.34) are compounds I.34-1I.34-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.34-1-I.34-300 from table. I.34 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.35. Preferred compounds of formula (I.35) are compounds I.35-1I.35-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.35-1-I.35-300 from table. I.35 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.36. Preferred compounds of formula (I.36) are compounds I.36-1I.36-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.36-1-I.36-300 from table. I.36 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.37. Preferred compounds of formula (I.37) are compounds I.37-1I.37-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.37-1-I.37-300 from table. I.37 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.38. Preferred compounds of formula (I.38) are compounds I.38-1I.38-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.38-1-I.38-300 from table. I.38 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.39. Preferred compounds of formula (I.39) are compounds I.39-1I.39-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.39-1-I.39-300 from table. I.39 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.40. Preferred compounds of formula (I.40) are compounds I.40-1I.40-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.40-1-I.40-300 from table. I.40 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

- 45 042989

Tab. I.41. Preferred compounds of formula (I.41) are compounds I.41-1I.41-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.41-1-I.41-300 from table. I.41 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.42. Preferred compounds of formula (I.42) are compounds I.42-1I.42-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.42-1-I.42-300 from table. I.42 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.43)

Tab. I.43. Preferred compounds of formula (I.43) are compounds I.43-1I.43-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.43-1-I.43-300 from table. I.43 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.44. Preferred compounds of formula (I.44) are compounds 1.44-1I.44-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds 1.44-1-I.44-300 from table. I.44 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

L (1.45)

Tab. I.45. Preferred compounds of formula (I.45) are compounds I.45-1I.45-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.45-1-I.45-300 from table. I.45 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.46. Preferred compounds of formula (I.46) are compounds I.46-1I.46-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.46-1-I.46-300 from table. I.46 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

.Q (1.47)

Tab. I.47. Preferred compounds of formula (I.47) are compounds I.47-1I.47-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.47-1-I.47-300 from table. I.47 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

,Q (1.48)

Tab. I.48. Preferred compounds of formula (I.48) are compounds I.48-1I.48-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.48-1-I.48-300 from table. I.48 are thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

- 46 042989

Tab. I.49. Preferred compounds of formula (I.49) are compounds I.49-1I.49-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.49-1-I.49-300 from table. I.49 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Tab. I.50. Preferred compounds of formula (I.50) are compounds I.50-1I.50-300, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.50-1-I.50-300 from table. I.50 is thus determined by the value of the corresponding entries No. 1-300 for Q from Table. 1.

Data spectral analysis of selected examples from the table.

a) Traditional interpretation of NMR

Example No. I.1-43:

¹ H-NMR (CDCl ₃ δ, ppm) 7.61 (m, 1H), 7.37 (d, 1H), 6.34 (s, 1H), 4.63-4.53 (m, 2H) , 4.20-4.13(m, 2H), 3.98-3.91(m, 1H), 3.55(s, 3H), 1.57(d, 3H), 1.25(t , 3H).

Example No. I.1-46:

1H-NMR (CDCl ₃ δ, ppm) 7.59 (m, 1H), 7.39-7.27 (m, 6H), 6.32 (m, 1H), 5.18-5.11 (m , 2H), 4.70-4.59 (m, 2H), 3.98-3.91 (m, IH), 3.53 (m, 3H), 1.55 (m, 3H).

Example No. I.1-51:

1H-NMR (CDCl ₃ δ, ppm) 7.63 (m, 1H), 7.37 (d, 1H), 6.34 (m, 1H), 4.63-4.53 (m, 2H), 4.13-4.09 (m, 2H), 3.96-3.93 (m, 1H), 3.55 (s, 3H), 1.62-1.55 (m, 5H), 1, 39-1.33 (m, 2H), 0.92 (t, 3H).

Example No. I.1-233:

1H-NMR (CDCl ₃ δ, ppm) 7.52 (m, 1H), 7.37 (d, 1H), 6.34 (s, 1H), 4.43-4.32 (m, 2H), 3.91-3.8 (m, 1H), 3.55 (s, 3H), 3.43-3.37 (m, 1H), 3.32-3.27 (m, 1H), 2, 92/2.88 (s, 3H), 2.57-2.51 (m, 2H), 1.52 (d, 3H), 1.15/1.07 (t, 3H).

Example No. I.2-6:

1H-NMR (CDCl ₃ δ, ppm) 7.48 (m, IH), 7.37-7.31 (m, 6H), 6.33 (m, IH), 5.11 (s, 2H), 4.39-4.26(m, 2H), 3.66(m, 1H), 3.52(m, 3H), 2.62-2.56(m, 2H), 1.97-1, 89 (m, 1H), 1.86-1.75 (m, 1H), 1.04 (t, 3H).

Example No. I.8-54:

1H-NMR (CDCl ₃ δ, ppm) 7.53 (d, 1H), 7.35 (d, IH), 6.34 (s, 1H), 5.03-4.97 (sept, 1H), 4.59 (s, 2H), 3.74 (s, 2H), 3.55 (s, 3H), 1.24 (d, 6H).

Example No. I.8-46:

1H-NMR (CDCl ₃ δ, ppm) 7.51 (m, IH), 7.39-7.28 (m, 6H), 6.32 (s, 1H), 5.14 (s, 2H), 4.69 (s, 2H), 3.983.74 (s, 2H), 3.53 (s, 3H).

Example No. I.8-51:

1H-NMR (CDCl ₃ δ, ppm) 7.52 (d, 1H), 7.35 (d, IH), 6.34 (s, 1H), 4.63 (s, 2H), 4.10 ( t, 2H), 3.74 (s, 2H), 3.55 (s, 3H), 1.63-1.56 (m, 5H), 1.42-1.32 (m, 2H), 0 .93 (t, 3H).

Example No. I.12-3:

1H-NMR (CDCl ₃ δ, ppm) 7.47 (m, 1H), 7.35 (m, 1H), 4.39-4.24 (m, 2H), 4.17-4.09 (m , 2H), 3.70-3.67(m, 1H), 3.54(s, 3H), 2.62-2.55(m, 2H), 2.27-2.22(m, 3H ), 1.99-1.91 (m, 1H), 1.89-1.81 (m, 1H), 1.25 (t, 3H), 1.06 (t, 3H).

Example No. I.14-3:

1H-NMR (CDCl ₃ δ, ppm) 7.47 (m, 1H), 7.36 (m, 1H), 4.37-4.29 (m, 1H), 4.28-4.20 (m , 1H), 4.13-4.10 (q, 2H), 3.84-3.80 (m, 1H), 3.54 (s, 3H), 2.58-2.52 (m, 2H ), 2.24-2.20 (m, 3H), 1.89-1.82 (m, 1H), 1.78-1.73 (m, 1H), 1.69-1.60 (m , 2H), 1.31-1.22 (m, 4H), 0.96-0.92 (m, 6H).

Example No. I.47-3:

1H-NMR (d6-DMSO δ, ppm) 7.85 (m, 1H), 7.70 (m, 1H), 6.60 (m, 1H), 4.27-4.21 (m, 1H) , 4.20-4.14(m, 1H), 4.06(q, 2H), 3.92-3.87(m, 1H), 3.47(s, 3H), 2.59-2 .55 (m, 2H), 1.87-1.78 (m, 1H), 1.76-1.68 (m, 1H), 1.42-1.24 (m, 4H), 1.17 (t, 3H), 0.85 (t, 3H).

Example No. I.47-6:

1H-NMR (CDCl ₃ δ, ppm) 7.56 (m, 1H), 7.36-7.32 (m, 6H), 6.33 (m, 1H), 5.11 (s, 2H), 4.39-4.25(m, 2H), 3.72(m, 1H), 3.52(m, 3H), 2.62-2.58(m, 2H), 1.93-1, 88 (m, 1H), 1.81-1.73 (m, 1H), 1.45-1.33 (m, 4H), 0.91 (t, 3H).

List of peaks in the NMR method

1H NMR data for selected examples are shown as 1H NMR peak lists. For

- 47 042989 each signal peak is given first the δ value in ppm and then the signal intensity in parentheses. Pairs of numbers value δ/signal intensity for peaks of different signals are given separated from each other by a semicolon.

The example peak list therefore becomes: δ1 (intensity^; δ ₂ (intensity ₂ ); ; δ _i (intensity^; ; δ _n (intensity^). see and shows the real ratios of the signal intensity values.In the case of wide signals, several peaks or the center of the signal and its relative intensity in comparison with the most intense signal in the spectrum can be shown.

To calibrate the 1H NMR chemical shift, the present inventors used tetramethylsilane and/or solvent chemical shift, in particular in the case of spectra that were measured in DMSO. Therefore, a tetramethylsilane peak may be present in NMR peak listings, but this is not required.

1H NMR peak listings are similar to traditional 1H NMR printouts and thus typically contain all of the peaks listed in the traditional NMR interpretation.

In addition, like traditional 1H NMR printouts, they may show solvent signals, stereoisomer signals of target compounds, which are likewise represented in the present invention, and/or impurity peaks. While providing information on the delta signals of compounds for solvents and/or water, the 1H NMR peak listings show standard solvent peaks, eg DMSO peaks in DMSO-D6 and water peak, which are typically high on average. Stereoisomer peaks of the target compounds and/or impurity peaks typically have an average lower intensity than the target compound peaks (eg, >90% pure).

Such stereoisomers and/or impurities may be typical of a particular production process. Their peaks can thus assist in identifying the reproduction of the presented preparation process by means of the characteristic properties of the by-products. An expert who calculates target compound peaks by known methods (MestreC, ACD simulation, or using empirically estimated expected values) can highlight the target compound peaks if necessary, optionally with additional intensity filters. This selection will be similar to the selection of significant peaks in the traditional interpretation of H-NMR. Additional details for 1H NMR peak listings can be found in Research Disclosure Database #564025.

Example No. I.1-1:

'H-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.5183 (3.8); 7.4518(5.2); 7.4451 (5.5); 7.4331 (5.2);

7.4266 (5.5); 7.3877 (5.3); 7.3802 (5.6); 7.3647 (5.4); 7.3574 (5.8); 7.3089 (3.1); 7.2966 (1.7); 7.2594 (648.9); 7.2081 (1.9); 6.9953 (3.5); 6.4114 (10.7); 5.2986 (13.6); 4.4561 (1.0);

4.4428 (1.1); 4.4391 (1.3); 4.4283 (2.6); 4.4157 (2.3); 4.3991 (2.7); 4.3848 (2.0); 4.3717 (1.5); 4.3320 (1.5); 4.3188 (2.4); 4.3120 (1.7); 4.3038 (2.4); 4.2998 (2.2); 4.2958 (1.8);

4.2902 (1.9); 4.2840 (2.6); 4.2715 (1.5); 4.2561 (1.0); 3.9480 (1.3); 3.9424 (1.4); 3.9298 (4.3); 3.9245 (4.4); 3.9117(4.2); 3.9064 (4.3); 3.8938 (1.4); 3.8883 (1.3); 3.5810 (13.9);

3.5780 (15.6); 3.5735 (16.0); 3.5705 (14.1); 2.5391 (5.6); 2.5241 (9.8); 2.5174 (3.5); 2.5104 (4.4); 2.0054 (1.3); 1.5698 (18.9); 1.5676 (18.0); 1.5516 (18.5); 1.5495 (17.3); 0.1462 (1.0);

0.0494 (1.1); 0.0079 (8.6); -0.0002 (238.4); -0.0084 (6.9); -0.0515 (0.7); -0.1495 (0.9)

Example No. I.1-2:

D-NMR (400 MHz, CDC13 δ, ppm) 7.4907 (0.6); 7.4847 (0.7); 7.4719 (0.7); 7.4659 (0.7);

7.3814 (0.7); 7.3777 (0.7); 7.3587 (0.7); 7.3549 (0.7); 7.2595 (75.2); 6.3512 (1.2); 6.3475 (1.2); 4.2934 (0.7); 3.8837 (1.0); 3.8658 (1.0); 3.6668 (6.2); 3.5515 (3.0); 3.5489 (3.0);

2.5821 (0.6); 2.5665 (1.0); 2.5548 (0.7); 2.5517 (0.7); 1.5327 (16.0); 1.5232 (3.7); 1.5053 (3.6); 1.3686 (0.7); 0.0078 (0.9); -0.0002 (26.8); -0.0085 (0.8)

- 48 042989

Example No. I.1-3:

'H-NMR (400 MHz, CDCI3 δ, ppm) 7.5184 (2.3); 7.4974 (3.4); 7.4908(3.6); 7.4786 (3.5); 7.4720 (3.5); 7.3800 (3.7); 7.3760 (3.7); 7.3572 (3.8); 7.3532 (3.7); 7.2914 (1.0); 7.2841 (0.8); 7.2595 (404.0); 6.9955 (2.3); 6.3497 (5.6); 6.3444 (5.7); 4.3686 (0.5); 4.3513 (0.7); 4.3409 (1.5); 4.3340 (1.5); 4.3262 (1.6); 4.3237 (1.9); 4.3190 (1.7); 4.3162 (2.0); 4.3130 (1.7); 4.3092 (2.6); 4.3012 (1.8); 4.2976 (2.5); 4.2944 (2.7); 4.2819 (2.0); 4.2783 (1.6); 4.2665 (1.0); 4.2542 (0.5); 4.1591 (0.7); 4.1509 (2.2); 4.1487 (2.3); 4.1412 (0.8); 4.1331(6.4); 4.1308 (6.6); 4.1152 (6.5); 4.1129 (6.6); 4.0974 (2.2); 4.0951 (2.3); 3.8988 (1.3); 3.8809 (4.4); 3.8630 (4.4); 3.8452 (1.3); 3.5504 (15.3); 3.5475 (15.8); 2.6517 (0.5); 2.5959 (0.7); 2.5805 (0.6); 2.5704 (3.0); 2.5552 (5.2); 2.5447 (2.1); 2.5415 (3.8); 2.5393 (4.7);

2.5272 (1.7); 2.5239 (1.6); 2.5005 (0.5); 2.0331 (1.0); 2.0277 (1.2); 1.5691 (1.8); 1.5531 (1.8); 1.5223 (20.8); 1.5044 (20.3); 1.2744 (0.8); 1.2652 (7.8); 1.2634 (8.0); 1.2565 (1.8); 1.2473 (15.5); 1.2455 (16.0); 1.2388 (1.2); 1.2295 (7.5); 1.2277 (7.6); 0.3308 (0.7); 0.2375 (0.5); 0.1574 (0.7); 0.1459 (0.6); 0.0079 (5.2); -0.0002 (177.4); -0.0085 (5.4); -0.1495 (0.7)

Example No. I.1-5:

'H-NMR (400 MHz, CDC13 δ, ppm) 7.5186 (1.7); 7.5125 (3.7); 7.5068 (3.8); 7.4938 (3.7); 7.4880 (3.8); 7.3787 (3.8); 7.3750 (4.0); 7.3559 (3.8); 7.3522 (4.0); 7.2861 (0.6); 7.2597 (283.3); 6.9957 (1.6); 6.3505 (5.9); 6.3439 (6.1); 5.2986 (3.6); 4.3112 (0.7); 4.3083 (0.6); 4.3026 (1.5); 4.2984 (1.8); 4.2932 (0.7); 4.2877(1.9); 4.2839 (3.7); 4.2807 (2.4); 4.2779 (1.8); 4.2689 (3.3); 4.2624 (2.8); 4.2562 (0.8); 4.2527 (1.7); 4.2466 (1.5); 4.2409 (0.8);

4.2348 (0.8); 3.8956 (0.8); 3.8918 (0.9); 3.8776 (3.0); 3.8739 (3.2); 3.8597 (3.1); 3.8560 (3.2); 3.8419 (0.9); 3.8382 (0.9); 3.5503 (15.5); 3.5477 (16.0); 2.5151 (0.8); 2.4994 (0.5);

2.4896 (2.6); 2.4741 (5.8); 2.4616 (2.7); 2.4587(4.9); 2.4443 (1.7); 2.4400 (1.6); 1.6097 (7.4); 1.5210 (20.5); 1.5031(20.2); 1.4472 (1.0); 1.4308 (92.0); 1.4293 (95.4); 0.0080 (3.2); 0.0002 (102.5); -0.0085 (2.9)

Example No. I.1-6:

¹ H-NMR (400 MHz, CDC13 δ, ppm) 7.5183 (9.6); 7.4723 (6.0); 7.4603 (6.4); 7.4536 (6.0); 7.4416 (6.4); 7.3726 (3.6); 7.3599 (3.3); 7.3550 (7.3); 7.3498 (9.4); 7.3418 (23.8); 7.3352 (29.0); 7.3271 (10.7); 7.3217 (10.2); 7.3178 (6.1); 7.2979 (2.2); 7.2931 (2.2); 7.2906 (2.5); 7.2867 (2.9); 7.2843 (2.9); 7.2820 (3.1); 7.2772 (4.8); 7.2740 (6.0); 7.2732 (6.2); 7.2724 (6.7); 7.2700 (9.6); 7.2684 (11.8); 7.2668 (15.6); 7.2594 (1724.6); 7.2378 (1.0); 7.2271 (1.1); 7.2088 (1.9); 6.9954 (9.8); 6.3351 (9.3); 6.3182 (9.6); 5.2985 (9.0); 5.1439 (1.0); 5.1092 (16.0); 5.0770 (0.9); 4.3853 (1.1); 4.3707 (1.2); 4.3675 (1.4); 4.3578 (3.2); 4.3529 (1.6); 4.3483 (2.4); 4.3431 (3.5); 4.3399 (3.0); 4.3334 (2.7); 4.3304 (3.2); 4.3251(2.6); 4.3212 (3.2); 4.3155 (2.7); 4.3051 (6.0); 4.2895 (3.3); 4.2773 (2.4); 4.2611 (1.3); 3.8686 (1.4);

3.8506(5.2); 3.8354 (5.6); 3.8328 (5.6); 3.8175 (5.6); 3.7997 (1.4); 3.5307 (13.7); 3.5276 (14.2); 3.5048 (13.0); 3.5018 (13.5); 2.6667 (0.9); 2.6514 (1.5); 2.6252 (4.9); 2.6096 (9.3); 2.5942 (8.4); 2.5798 (2.6); 2.5755 (2.4); 2.5526 (1.0); 2.0049 (0.9); 1.5343 (143.3); 1.4845 (21.0); 1.4823 (21.6); 1.4666 (20.2); 1.4644 (21.0); 1.2844 (0.8); 1.2562 (1.5); 0.1459 (2.8); 0.1131 (1.2); 0.0334 (1.0); 0.0080 (27.7); 0.0064 (10.6); 0.0055 (11.6); 0.0047 (13.5); -0.0002 (851.4); -0.0059 (10.4); -0.0067 (9.1); -0.0085 (24.9); -0.0115 (2.7); -0.0163 (1.1); -0.0219 (0.9); -0.0507 (0.8); -0.1496 (2.5)

Example No. I.1-8:

¹ H-NMR (400 MHz, CDC13 δ, ppm) 7.4969 (1.0); 7.4900 (1.0); 7.4782 (1.0); 7.4713 (1.0); 7.3794 (1.0); 7.3754 (1.0); 7.3566 (1.0); 7.3527 (1.0); 7.2689 (0.6); 7.2681 (0.7); 7.2673 (0.8); 7.2665 (0.9); 7.2657 (1.1); 7.2649 (1.4); 7.2600 (86.0); 7.2535 (0.9); 7.2527 (0.8); 7.2519 (0.6); 6.3488 (1.6); 6.3429 (1.4); 4.3383 (0.5); 4.3274 (0.5); 4.3231 (0.5); 4.3126 (0.7); 4.2976 (0.6); 4.2934 (0.6); 4.2815 (0.5); 4.0445 (1.1); 4.0420 (1.1); 4.0276 (2.1); 4.0252(2.2); 4.0107 (1.1); 4.0084 (1.1); 3.8806 (0.9); 3.8789 (0.9); 3.8628 (0.9); 3.8609 (0.9); 3.5496 (4.3); 3.5465 (4.3); 2.5810 (0.7); 2.5657 (1.3); 2.5499 (1.1); 1.6638 (0.8); 1.6452 (1.5); 1.6283 (1.4); 1.6098 (0.8); 1.5759 (16.0); 1.5206 (5.4); 1.5027 (5.4); 0.9465 (2.3); 0.9379 (0.7); 0.9278 (4.6); 0.9094 (2.0); 0.0080 (1.0); -0.0002 (29.7); -0.0085 (0.8)

- 49 042989

Example No. I.1-22:

'H-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.5185 (1.1); 7.5088 (1.3); 7.5008 (1.4); 7.4901 (1.3); 7.4821 (1.4); 7.4670 (1.4); 7.4639 (1.3); 7.4486 (1.3); 7.4453 (1.4); 7.3670 (3.9); 7.3442 (3.9); 7.2596 (208.2); 6.9956 (1.1); 6.3503 (5.7); 5.2986 (1.2); 5.2520 (0.7); 5.2411 (0.8); 5.2366 (0.8); 5.2224 (0.9); 5.2065 (0.8); 5.1930 (0.5); 3.8666 (1.0); 3.8595 (1.1); 3.8486 (1.4); 3.8416 (1.2); 3.8304 (1.5); 3.8123 (1.2); 3.6461 (16.0); 3.6371 (15.2); 3.5523 (9.9); 3.5494 (9.4); 2.6192 (1.1); 2.6004 (1.0); 2.5802 (1.9); 2.5614 (1.8); 2.4937 (0.9); 2.4901 (0.9); 2.4800 (0.9); 2.4767 (1.0); 2.4659 (0.8); 2.4574 (0.8); 2.4512 (1.3); 2.4422 (1.0); 2.4182 (0.5); 2.4122 (0.5); 1.7277 (1.0); 1.5155 (9.2); 1.4976 (9.2); 1.2638 (4.1); 1.2611 (4.4); 1.2480(4.2); 1.2453 (4.3); 1.2018 (8.0); 1.1860 (7.9); 0.0080 (2.1); -0.0002 (73.2); 0.0085 (2.3)

Example No. I.1-23:

Ή-NMR (400 MHz, CDC13 δ, ppm) 7.5184 (3.1); 7.5151(2.4); 7.5053 (2.4); 7.4965 (2.2); 7.4867 (2.3); 7.4723 (2.2); 7.4696 (2.2); 7.4538 (2.2); 7.3660 (5.9); 7.3433 (5.9); 7.2871 (1.2); 7.2596 (522.0); 7.2267 (1.1); 7.2099 (1.0); 6.9956 (2.9); 6.3471 (8.1); 5.2986 (6.9); 5.2630 (1.0); 5.2486 (1.6); 5.2332 (1.6); 5.2153 (1.2); 5.2003 (0.9); 4.2038 (1.0); 4.1861 (3.1); 4.1682 (3.1); 4.1503 (1.2); 4.1300 (1.4); 4.1242 (2.3); 4.1121 (4.2); 4.1063(6.7); 4.0942 (4.4); 4.0885 (6.8); 4.0765 (1.5); 4.0707 (2.3); 3.8751 (0.6); 3.8648 (1.7); 3.8577 (1.8); 3.8466 (2.1); 3.8397 (1.9); 3.8272 (3.1); 3.8091 (2.8); 3.7913 (0.8); 3.5514 (16.0); 3.5484 (14.9); 2.9716 (0.9); 2.9634 (0.9); 2.6089 (1.0); 2.6042 (1.0); 2.5897 (1.1); 2.5853 (0.9); 2.5732 (1.7); 2.5697 (1.9); 2.5652 (1.7); 2.5568 (1.5); 2.5506 (1.7); 2.5462 (1.6); 2.4759 (2.1); 2.4646 (1.7); 2.4608(1.7); 2.4509 (1.3); 2.4429 (2.6); 2.4363 (2.0); 2.4278 (1.3); 2.4212 (2.0); 2.4119 (0.9); 2.4038 (0.9); 2.3973 (1.0); 2.3890 (0.8); 2.0051 (0.6);

1.5347 (122.2); 1.5187 (9.1); 1.5131 (13.4); 1.5008 (9.2); 1.4952 (13.0); 1.2962(3.6); 1.2783 (7.2); 1.2604(11.1); 1.2566 (6.1); 1.2443 (11.3); 1.2387(14.0); 1.2277 (9.9); 1.2256(11.0); 1.2228 (7.1); 1.2099 (4.8); 1.2078(5.2); 1.1997 (13.0); 1.1839 (12.6); 0.1459 (0.8); 0.0079 (5.8); -0.0002 (185.2); -0.0085 (5.1); -0.1496 (0.8)

Example No. I.1-32:

'H-NMR (400 MHz, CDCh δ, ppm) 7.5184 (0.9); 7.4862 (2.0); 7.4739(2.2); 7.4677 (2.0); 7.4551 (2.1); 7.3630 (2.5); 7.3400 (2.5); 7.2596 (168.8); 6.9955 (0.9); 6.3526 (3.7); 6.3485 (3.8); 4.1714 (1.6); 4.1624 (1.7); 4.1446 (2.5); 4.1357(2.6); 4.0597 (2.6); 4.0430 (2.4);

4.0330 (1.6); 4.0163 (1.6); 3.8935 (0.7); 3.8755 (2.1); 3.8580 (2.1); 3.8401 (0.6); 3.6775 (1.6); 3.6454 (14.6); 3.6403 (15.1); 3.5530 (9.5); 2.0126 (0.8); 2.0050 (1.0); 1.5784 (3.1); 1.5245 (11.4); 1.5067 (11.2); 1.2079(1.5); 1.1642(12.2); 1.1615(11.9); 1.1356(16.0);

0.0079 (2.1); -0.0002 (65.2); -0.0085 (1.9)

Example No. I.1-42:

'H-NMR (400 MHz, CDC13 δ, ppm) 7.6230 (2.3); 7.6040 (2.4); 7.5965 (2.2); 7.5776 (2.2); 7.5183 (2.5); 7.3813 (2.5); 7.3759 (2.3); 7.3663 (0.6); 7.3585 (2.5); 7.3532 (2.3); 7.3094 (1.0); 7.2920 (0.5); 7.2594 (453.3); 7.2098 (0.6); 6.9954 (2.4); 6.3457 (3.4); 6.3387 (3.8); 4.7127 (0.9); 4.7018 (0.6); 4.6559 (1.0); 4.6504 (1.5); 4.6355 (0.6); 4.6102(3.4); 4.5959 (4.0); 4.5838 (5.5); 4.5434 (1.2); 3.9686 (1.9); 3.9555 (2.0); 3.9506(1.9); 3.9375 (1.9); 3.9327 (0.7); 3.9198 (0.6); 3.7402 (1.6); 3.7244 (1.8); 3.7084 (15.2); 3.7040 (16.0); 3.5501 (10.1); 3.5470 (10.8); 3.5295 (0.7); 2.0049 (0.7); 1.5911 (7.4); 1.5852 (8.0); 1.5731 (9.3); 1.5672(12.1); 1.5606 (8.6); 0.0079 (4.7); -0.0002 (167.9); -0.0085 (5.1); -0.1495 (0.6)

Example No. I.1-71:

'H-NMR (400 MHz, CDC13 δ, ppm) δ= 7.4932 (3.4); 7.4890 (3.3); 7.4743 (3.5); 7.4702 (3.3); 7.3814 (3.8); 7.3784 (3.7); 7.3587 (3.8); 7.3557(3.6); 7.2603 (78.2); 6.3869 (5.5); 6.3770 (5.2); 5.2985 (14.1); 4.9902 (0.7); 4.9798 (0.8); 4.9724 (2.5); 4.9622 (2.8); 4.9547(2.6);

4.9445 (2.8); 4.9370 (0.8); 4.9267 (0.8); 4.1333 (0.7); 4.1271 (0.7); 4.1154 (2.1); 4.1093 (2.1); 4.0975 (2.1); 4.0915 (2.1); 4.0797 (0.7); 4.0734 (0.6); 3.5715 (7.7); 3.5687 (7.9);

3.5579 (8.5); 3.5551 (8.8); 1.5699 (10.6); 1.5678 (10.9); 1.5520 (10.6); 1.5500 (10.8); 1.5297 (0.6); 1.5258 (0.5); 1.4225 (16.0); 1.4048 (15.9); 0.0080 (1.0); -0.0002 (30.3); -0.0085 (1.1)

- 50 042989

Example No. I.1-72:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.6037 (1.5); 7.5850 (1.6); 7.5603 (1.9); 7.5572 (2.8); 7.5418 (1.9); 7.5382 (2.7); 7.5183 (2.5); 7.3846 (2.0); 7.3795 (1.9); 7.3611(3.2); 7.3563 (3.4); 7.3379 (1.7); 7.3334 (1.8); 7.2883 (0.5); 7.2811 (0.6); 7.2803 (0.6); 7.2794 (0.6); 7.2787 (0.7); 7.2779 (0.8); 7.2771 (0.8); 7.2763 (0.8); 7.2755 (0.9); 7.2747 (1.0); 7.2739 (1.1); 7.2731 (1.2); 7.2723 (1.4); 7.2715 (1.5); 7.2707(1.7); 7.2699 (2.0); 7.2691(2.2); 7.2683 (2.5); 7.2675 (2.8); 7.2667 (3.2); 7.2659 (4.0); 7.2650 (5.0); 7.2594 (418.8); 7.2530 (3.5); 7.2506 (1.3); 7.2497 (1.0); 7.2489 (0.8); 7.2481 (0.7); 7.2473 (0.7); 7.2465 (0.6); 7.2457 (0.5); 7.2449 (0.6); 6.9954 (2.4); 6.3526 (3.0); 6.3406(3.2); 6.3369 (2.8); 5.2983 (4.7); 5.0983 (1.5); 5.0808(2.2); 5.0633 (1.4); 5.0227 (1.4); 5.0144 (1.4); 5.0050 (1.4); 4.9968 (1.5); 4.0133 (1.6); 4.0086 (1.7); 3.9954 (1.7); 3.9908 (1.8); 3.9240 (1.3); 3.9160 (1.3); 3.9059 (1.4); 3.8978 (1.4); 3.7010 (15.3); 3.6982 (16.0); 3.6824 (14.3); 3.6806 (14.0); 3.5592 (4.3); 3.5560 (4.6); 3.5451 (10.1); 1.6000 (11.6); 1.5958 (13.2); 1.5884 (8.5); 1.5776 (6.0); 1.5702(5.7); 1.5619 (6.3); 1.5577 (6.6); 1.5440 (5.9); 1.5398 (6.2); 1.4603(5.5); 1.4487 (5.7); 1.4426 (5.6); 1.4310 (5.6); 1.3514 (8.6); 1.3338 (8.7); 0.0079 (5.1); 0.0063 (1.7); 0.0054 (2.0); 0.0046 (2.6); -0.0002 (163.8); -0.0051 (2.6); -0.0060 (2.1); -0.0069 (2.0); 0.0085 (4.8)

Example No. I.1-102:

Ή-NMR (400 MHz, d ₆ -DMSO δ, ppm) 7.8549 (1.5); 7.8513 (1.4); 7.8312 (1.5); 7.8274 (1.4). 7.7657 (1.2); 7.7594 (1.3); 7.7466 (1.2); 7.7407 (1.3); 6.6184 (2.6); 6.6151(2.6); 5.7526(3.6); 4.1723 (1.0); 4.1610 (1.1); 4.1545 (1.0); 4.1433 (1.0); 3.5974 (16.0); 3.4230 (5.7);

3.3081 (219.0); 2.6738 (1.3); 2.6692 (1.8); 2.6646 (1.3); 2.5226 (9.0); 2.5179 (12.6); 2.5093 (113.1); 2.5047 (230.5); 2.5002 (313.9); 2.4956 (216.7); 2.4911(97.9); 2.3316 (1.3); 2.3270 (1.9); 2.3224 (1.3); 1.4714 (6.4); 1.4537 (6.3); 1.4125 (0.8); 1.3962 (0.6); 1.3474 (0.6);

1.3294 (0.9); 1.1382 (0.7); 1.1236 (2.0); 1.1084(1.3); 1.0813 (0.5); 0.0080 (3.6); -0.0002 (112.5); -0.0085 (3.6)

Example No. I.1-127:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.5184 (1.2); 7.4816 (1.2); 7.4687 (1.2); 7.4630 (1.2); 7.4502 (1.2); 7.3700 (1.2); 7.3650 (1.3); 7.3473 (1.2); 7.3423 (1.2); 7.2595 (203.8); 6.9955 (1.2); 6.3486 (3.6); 5.4824 (0.7); 5.4665 (0.5); 3.8281(1.3); 3.8106 (1.3); 3.6485 (16.0); 3.6445 (10.0); 3.6424 (9.8); 3.5498 (5.3); 2.6900 (2.0); 2.6862 (1.2); 2.6756 (2.7); 2.6694 (1.2); 2.6590 (2.4); 2.6490 (1.1); 2.6430 (1.8); 2.6334 (1.1); 2.6241 (0.9); 1.5339 (58.3); 1.5154 (5.7); 1.4974 (5.6); 0.0080 (2.4); -0.0002 (77.4); -0.0085 (2.2)

Example No. I.1-132:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.5307 (1.7); 7.5246 (1.7); 7.5120 (1.8); 7.5059 (1.7); 7.3713 (1.8); 7.3673 (1.8); 7.3486 (1.8); 7.3446 (1.8); 7.2604 (50.2); 6.3441 (5.2); 3.9130 (1.4); 3.9058 (1.4); 3.8950 (1.4); 3.8878 (1.4); 3.6714 (16.0); 3.6698 (15.8); 3.5485 (7.3); 3.5457 (7.6); 2.0048 (3.0); 1.5546 (7.6); 1.5400 (5.4); 1.5360 (5.6); 1.5220 (5.3); 1.5180 (5.4); 1.4765 (9.1); 1.4711(25.5); 0.0079 (0.6); -0.0002 (21.9); -0.0085 (0.7)

- 51 042989

Example No. I.1-141:

'H-NMR (400 MHz, CDC13 δ, ppm) 7.6862 (3.7); 7.6780 (4.3); 7.6674 (4.0); 7.6592 (8.0);

7.6511 (4.1); 7.6404 (4.0); 7.6324 (4.1); 7.5185 (3.5); 7.3841 (6.6); 7.3802 (7.4); 7.3614 (6, 2); 7.3575 (7.6); 7.3178 (0.7); 7.3107 (0.8); 7.3092 (2.1); 7.3020 (0.6); 7.2940 (0.8);

7.2908 (0.7); 7.2892 (0.5); 7.2837 (0.8); 7.2829 (0.7); 7.2820 (0.9); 7.2813 (0.8); 7.2804 (0.9); 7.2797 (1.1); 7.2789 (1.1); 7.2781 (1.1); 7.2773 (1.3); 7.2765 (1.3); 7.2757 (1.5);

7.2749 (1.6); 7.2741 (1.6); 7.2733 (1.6); 7.2725 (1.8); 7.2717 (2.0); 7.2709 (2.0); 7.2701 (2, 4); 7.2693 (2.7); 7.2685 (3.1); 7.2677 (3.7); 7.2669(4.2); 7.2661 (4.9); 7.2653 (6.0);

7.2645 (7.8); 7.2637 (10.4); 7.2596 (611.7); 7.2556 (21.9); 7.2548 (17.5); 7.2540 (14.6);

7.2532(12.2); 7.2524 (10.4); 7.2516 (8.8); 7.2507 (7.7); 7.2499 (7.2); 7.2491 (6.6); 7.2483 (6.2); 7.2475 (5.7); 7.2467 (5.4); 7.2459 (5.0); 7.2451 (4.6); 7.2443(4.4); 7.2436 (4.3);

7.2428 (3.9); 7.2419 (3.8); 7.2412 (3.7); 7.2404 (3.5); 7.2396 (3.3); 7.2387 (3.3); 7.2380 (3.2); 7.2372 (3.1); 7.2364 (3.1); 7.2356 (3.0); 7.2340 (3.2); 7.2236 (1.9); 7.2197 (1.8);

7.2149 (1.6); 7.2089 (0.9); 7.2054 (0.9); 7.1974 (0.9); 7.1588 (1.1); 7.1467 (0.6); 6.9956 (3.5); 6.3483 (5.7); 6.3318 (5.9); 6.3215 (7.2); 6.3171 (6.7); 5.4442 (1.8); 5.4366 (1.7);

5.4226 (2.1); 5.4192 (2.2); 5.4148 (2.2); 5.4110 (2.2); 5.3973 (2.0); 5.3892 (1.9); 5.3466 (1.8); 5.3225(3.9); 5.3005 (4.5); 5.2985 (7.9); 5.2763 (2.2); 4.4636 (0.8); 4.4582 (1.0);

4.4500 (1.0); 4.4407 (2.0); 4.4353 (2.1); 4.4273 (2.5); 4.4221 (2.7); 4.4183 (1.6); 4.4128 (1.3); 4.4062(3.9); 4.4003 (4.2); 4.3835 (2.1); 4.3776 (2.0); 4.2771 (1.3); 4.2704 (1.3);

4.2615 (2.3); 4.2589 (1.7); 4.2543(2.6); 4.2519 (1.9); 4.2456 (2.8); 4.2427 (2.1); 4.2375 (3.3); 4.2359 (3.3); 4.2314 (1.9); 4.2289 (2.9); 4.2215 (3.0); 4.2143 (2.0); 4.2111 (1.7);

4.2062 (1.3); 4.1980 (1.4); 4.1949 (1.4); 4.0885 (0.8); 4.0760 (1.1); 4.0707 (3.3); 4.0582 (4.0); 4.0530 (3.6); 4.0404 (4.1); 4.0354 (1.1); 4.0227 (1.1); 3.8910 (0.8); 3.8728 (3.4);

3.8548 (3.7); 3.8381 (3.7); 3.8201 (3.3); 3.8021 (0.9); 3.5512 (10.9); 3.5481 (11.4); 3.5391 (10.4); 3.5358 (13.1); 3.5324 (14.0); 3.5289 (15.1); 3.5247 (12.0); 2.6357 (1.1); 2.6304 (1.1);

2.6199 (1.3); 2.6143 (1.9); 2.6086 (1.3); 2.6038 (1.6); 2.5983 (3.0); 2.5926 (1.8); 2.5880 (1.8); 2.5822 (2.8); 2.5764 (2.4); 2.5660 (2.0); 2.5597 (2.3); 2.5535 (1.1); 2.5490 (1.1);

2.5434 (1.8); 2.5376 (1.2); 2.5271 (1.1); 2.5215 (0.9); 2.3182 (0.6); 2.3052 (0.6); 2.2927 (1.3); 2.2865 (0.7); 2.2800 (1.4); 2.2701 (1.5); 2.2673 (1.0); 2.2609 (1.4); 2.2575 (1.5);

2.2481(1.3); 2.2447 (0.8); 2.2382 (1.2); 2.2322 (0.8); 2.2256 (1.2); 2.2125 (0.5); 2.1403 (1.4); 2.1333 (1.0); 2.1240 (0.8); 2.1157(1.9); 2.1082 (0.7); 2.0995 (1.6); 2.0931(1.6);

2.0834 (1.3); 2.0768 (1.7); 2.0674 (1.7); 2.0610 (1.3); 2.0520 (0.7); 2.0445 (1.4); 2.0365 (0.6); 2.0199 (0.6); 2.0049 (0.9); 1.6350 (4.8); 1.6038 (16.0); 1.6019 (15.7); 1.5857 (15.5);

1.5838 (15.0); 1.5707 (25.7); 1.5529 (24.8); 0.3309 (0.9); 0.2376 (0.8); 0.1579 (1.2); 0.1460 (0.7); 0.1262 (0.6); 0.0494 (1.0); 0.0160 (0.6); 0.0136 (0.7); 0.0128 (0.7); 0.0120 (0.8);

0.0112 (0.9); 0.0104 (1.1); 0.0080 (8.0); 0.0065 (2.2); 0.0057 (2.5); 0.0048 (3.1); 0.0040 (4.2); -0.0002 (278.7); -0.0057 (7.2); -0.0066 (6.3); -0.0085 (10.3); -0.1497 (0.8)

Example No. I.1-142:

'H-NMR (400 MHz, CDCI3 5, ppm) 7.7293 (1.5); 7.7157 (1.8); 7.7104 (1.6); 7.6970 (1.7);

7.6551 (1.7); 7.6364 (1.7); 7.5952 (1.7); 7.5768 (1.7); 7.5184 (1.1); 7.3723 (1.6); 7.3620 (3.5); 7.3538 (1.9); 7.3496 (1.7); 7.3394 (3.6); 7.3314 (1.8); 7.2595 (203.2); 6.9955 (1.1);

6.3441 (2.4); 6.3296 (2.8); 6.3216 (4.8); 5.3188 (3.7); 5.3141 (3.8); 5.2962 (3.1); 5.2881(3.6); 4.0857 (1.2); 4.0761 (1.4); 4.0677 (1.2); 4.0582 (1.4); 4.0321 (1.0); 4.0248 (0.9);

4.0097 (3.1); 4.0014 (3.7); 3.9890 (4.4); 3.9724 (1.4); 3.9661(1.3); 3.9544 (1.4); 3.9362 (0.7); 3.9177 (1.3); 3.8996 (1.3); 3.5482 (4.2); 3.5452 (4.5); 3.5373 (4.3); 3.5342 (4.8);

3.5300 (4.4); 3.5266 (3.8); 3.5168 (4.1); 3.5138 (4.1); 2.1271 (0.7); 2.0046 (3.7); 1.6429 (5.1); 1.6367 (5.1); 1.6248 (5.4); 1.6186(5.5); 1.5949 (10.6); 1.5770(9.4); 1.1561(8.6);

1.1476 (16.0); 1.1391 (7.4); 1.0342 (11.6); 0.9934 (5.7); 0.9625 (6.7); 0.0079 (2.3); -0.0002 (81.5); -0.0085 (2.7)

- 52 042989

Example No. I.1-144:

'H-NMR (400 MHz, d ₆ -DMSO δ, ppm) 7.9102 (3.3); 7.8956 (3.4); 7.8617 (2.7); 7.8542 (3.4);

7.8374 (2.6); 7.8311 (3.1); 7.8257 (2.9); 7.7520 (3.9); 7.7333 (4.2); 7.7205 (2.4); 6.6041 (8.2); 6.5922 (3.8); 6.2417 (1.7); 6.2371 (3.0); 6.2316 (1.9); 6.2227 (2.8); 6.2171 (1.6);

5.7528 (9.5); 5.3130 (3.1); 5.2997 (3.2); 4.9603 (7.1); 4.9550 (11.9); 4.9506 (7.1); 4.4841 (1.9); 4.4715 (2.0); 4.4566 (2.6); 4.4440 (3.1); 4.4263 (1.5); 4.4163 (1.8); 4.4047 (1.2);

4.2561 (1.5); 4.2293 (1.6); 4.2109 (1.3); 4.1083 (2.2); 4.0906 (3.6); 4.0809 (2.0); 4.0731(2.6); 4.0592 (3.8); 4.0326 (2.8); 3.4257(20.9); 3.3084(331.5); 3.0207 (1.8); 3.0033 (2.2);

2.9939 (1.5); 2.9770 (2.5); 2.9569 (2.3); 2.9484 (1.4); 2.9325 (1.4); 2.6691(5.4); 2.5220 (41.3); 2.5085 (319.6); 2.5043 (620.2); 2.4999 (827.8); 2.4956 (601.1); 2.4914(298.3);

2.4311 (3.2); 2.3866 (1.2); 2.3267 (5.5); 2.2853 (1.2); 2.2675 (1.1); 2.0711 (1.1); 1.4451 (16.0); 1.4329 (8.0); 1.4274 (15.2); 1.2368 (1.1); 0.0074 (5.2); -0.0002 (123.3); -0.0083 (6.7)

Example No. I.1-145:

'H-NMR (400 MHz, CDC13 δ, ppm) 7.6028 (3.4); 7.5839 (3.5); 7.5724 (3.3); 7.5581 (3.3); 7.5536 (3.6); 7.5393 (3.2); 7.5211 (3.5); 7.5025 (3.4); 7.4106 (6.4); 7.4029 (3.8); 7.3972 (3.8); 7.3879 (6.7); 7.3801 (3.8); 7.3745 (3.6); 7.2724 (0.8); 7.2610 (127.6); 7.2117 (0.5);

6.9970 (0.7); 6.3471 (4.6); 6.3281 (5.1); 6.3159 (5.1); 6.3001(5.2); 4.6195 (0.6); 4.6109 (1.1); 4.6018 (1.3); 4.5921 (1.9); 4.5852 (1.7); 4.5742 (2.3); 4.5673 (1.9); 4.5634 (1.4);

4.5561 (2.2); 4.5491 (1.4); 4.5377 (0.9); 4.2747 (1.4); 4.2672 (1.4); 4.2539 (1.6); 4.2469 (1.9); 4.2443 (2.3); 4.2369 (2.4); 4.2308 (3.1); 4.2234 (3.8); 4.2164 (2.3); 4.2080 (2.4);

4.2005 (4.1); 4.1933 (2.3); 4.0909 (2.5); 4.0893 (2.4); 4.0808 (2.4); 4.0759 (2.8); 4.0637 (4.2); 4.0604 (2.4); 4.0506 (1.9); 4.0456 (3.8); 4.0334 (2.9); 4.0155 (1.6); 3.9946 (0.9);

3.9907 (1.0); 3.9856 (0.9); 3.9766 (3.0); 3.9728 (3.2); 3.9677 (2.9); 3.9589 (3.6); 3.9550 (3.4); 3.9499 (3.0); 3.9418 (3.6); 3.9371 (1.2); 3.9321 (1.0); 3.9239 (3.1); 3.9062 (0.9);

3.5502 (7.9); 3.5470 (9.2); 3.5419 (10.3); 3.5355 (16.0); 2.5425 (1.8); 2.5400 (2.0); 2.5373 (2.1); 2.5352 (1.9); 2.5282 (1.8); 2.5253(2.3); 2.5187 (7.0); 2.5129 (4.5); 2.5085(2.4);

2.5017 (3.7); 2.4971(5.2); 2.4873 (4.0); 2.4777 (2.2); 2.4752 (2.3); 2.4650 (2.0); 2.4513 (0.6); 2.4412 (0.5); 2.3289 (0.5); 2.3230 (0.5); 2.3104 (0.9); 2.3046 (0.9); 2.2964 (0.7);

2.2906 (1.3); 2.2843 (0.9); 2.2787 (1.4); 2.2761 (1.4); 2.2731(1.3); 2.2595 (1.6); 2.2571 (1.7); 2.2434 (1.2); 2.2404 (1.4); 2.2375 (1.1); 2.2344 (1.0); 2.2273 (1.3); 2.2241 (1.1);

2.2210 (1.2); 2.2080 (1.0); 2.2047 (1.1); 2.1857 (0.5); 1.8931 (0.5); 1.8883 (0.5); 1.8752 (0.6); 1.8695 (1.0); 1.8664 (0.8); 1.8595 (0.8); 1.8535 (1.2); 1.8476 (1.2); 1.8421(1.5);

1.8371 (1.7); 1.8332 (1.6); 1.8293 (1.4); 1.8209 (1.6); 1.8147 (2.0); 1.8093 (1.5); 1.8032 (1.1); 1.7969 (1.5); 1.7910 (1.2); 1.7822 (1.1); 1.7643 (0.7); 1.7582 (0.8); 1.5605 (9.7);

1.5536 (10.2); 1.5445 (14.7); 1.5428 (20.7); 1.5358 (11.0); 1.5267 (12.6); 1.5252 (11.7);

0.0079 (1.5); -0.0002 (51.8); -0.0085 (2.2)

Example No. I.1-151:

^X H-NMR (400 MHz, d ₆ -DMSO δ, ppm) 7.8607 (8.7); 7.8370 (9.0); 7.7546 (3.9); 7.7473 (4.3); 7.7354 (4.2); 7.7282 (4.2); 7.3034 (2.4); 6.8591 (2.5); 6.6152 (15.5); 4.2586 (0.9); 4.2419 (1.8); 4.2315 (2.5); 4.2150 (4.1); 4.1987(4.2); 4.1827 (5.0); 4.1666(2.6); 4.1556 (2.2);

4.1395 (1.1); 4.0575 (1.3); 4.0407 (5.4); 4.0229 (5.4); 4.0051 (1.4); 3.4363 (17.6); 3.3685 (67.3); 2.6854 (1.5); 2.5388 (5.0); 2.5341 (7.2); 2.5254 (89.1); 2.5208 (186.5); 2.5162 (259.7); 2.5116 (177.7); 2.5071 (79.7); 2.3991 (0.8); 2.3770 (3.0); 2.3696 (3.0); 2.3610 (6.6);

2.3532 (5.8); 2.3448 (3.5); 2.3370 (3.4); 2.0878 (3.1); 1.4301 (16.0); 1.4130 (15.8); 0.0157 (1.0)

Example No. I.1-152:

- 53 042989 'H-NMR (400 MHz, CDC1 ₃ δ, ppm) δ= 7.4893 (1.7); 7.4705 (1.7); 7.4609 (1.6); 7.4421 (1.6); 7.3982 (1.7); 7.3909 (1.7); 7.3755 (1.7); 7.3682 (1.7); 7.2598 (84.7); 6.3803 (2.8); 6.3665 (2.9); 4.3498 (0.6); 4.3444 (0.7); 4.3377 (0.8); 4.3287 (1.6); 4.3226 (1.4); 4.3135 (1.4);

4.3081 (1.4); 4.2948 (1.0); 4.2888 (0.8); 4.2744 (0.6); 3.9720 (0.5); 3.9674 (1.3); 3.9543 (1.4); 3.9495 (1.4); 3.9364 (1.3); 3.5750 (6.2); 3.5724 (6.2); 2.6723 (4.9); 2.6651 (5.2);

2.6604 (5.1); 2.6532 (4.6); 2.2788 (0.7); 2.2710 (0.5); 2.2639 (0.9); 2.2566 (1.0); 2.2446 (0.7); 2.2271 (0.7); 2.2224 (0.6); 2.2120 (0.6); 2.2071 (0.8); 2.1883 (0.6); 1.5429 (16.0);

1.5334 (5.1); 1.5256 (5.2); 1.5155 (4.8); 1.5077 (4.9); 0.0079 (2.0); -0.0002 (48.4); -0.0085 (1.6)

Example #1.1-153:

'H-NMR (400 MHz, CDC1 ₃ δ, ppm) δ= 7.5194 (0.7); 7.5029 (4.1); 7.4840 (4.2); 7.4740 (4.0); 7.4552 (4.0); 7.3953 (4.3); 7.3871(4.2); 7.3726 (4.3); 7.3644 (4.2); 7.3112 (0.8); 7.2606 (115.1); 7.2118 (0.8); 6.9965 (0.7); 6.3739 (6.5); 6.3542 (7.0); 6.1415 (0.7); 6.0210 (0.7);

4.3609 (0.5); 4.3541 (0.9); 4.3453 (1.4); 4.3422 (1.8); 4.3387 (0.9); 4.3316 (2.4); 4.3268 (3.6); 4.3179 (4.4); 4.3134 (2.8); 4.3054 (2.1); 4.3030 (2.1); 4.2991 (2.0); 4.2906 (2.0);

4.2864 (2.2); 4.2784 (0.7); 4.2716 (1.8); 4.2635 (0.6); 4.2592 (0.7); 4.2443 (0.6); 3.9695 (0.9); 3.9515 (3.5); 3.9368 (3.5); 3.9336 (3.8); 3.9189 (3.4); 3.9011 (0.9); 3.5717 (16.0);

3.2090 (1.0); 3.2042 (0.6); 3.1908 (3.3); 3.1861 (1.8); 3.1764 (3.7); 3.1725 (4.5); 3.1680 (2.0); 3.1587 (3.3); 3.1542 (2.7); 3.1405 (1.1); 3.1361 (0.6); 2.2940 (1.2); 2.2789 (1.4);

2.2712 (1.2); 2.2638 (0.7); 2.2564 (3.3); 2.2414 (3.5); 2.2334 (1.4); 2.2265 (1.2); 2.2179 (1.6); 2.2152 (1.8); 2.2124 (1.6); 2.1998 (1.5); 2.1962 (2.0); 2.1932 (1.8); 2.1774 (1.9);

2.1591 (0.7); 2.1557 (0.7); 2.1399 (0.5); 1.5580 (12.2); 1.5317 (11.8); 1.5237 (12.8); 1.5138 (11.9); 1.5058 (12.3); 1.0702 (7.7); 1.0668 (7.5); 1.0520 (15.9); 1.0486 (15.3); 1.0338 (7.6); 1.0304 (7.3); 0.0080 (2.0); -0.0002 (67.3); -0.0085 (2.6)

Example No. I.1-182:

'H-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.5411 (5.0); 7.5393 (5.0); 7.5223 (5.1); 7.5205 (5.3); 7.4091 (7.8); 7.3865 (7.8); 7.3100 (1.1); 7.2599 (286.8); 6.9959 (1.6); 6.3716 (6.9); 6.3620 (6.8); 5.9964 (1.0); 4.5648 (1.4); 4.5548 (1.1); 4.5267 (4.7); 4.5171 (5.2); 4.4983 (7.2);

4.4599 (1.6); 3.9302 (1.0); 3.9253 (1.0); 3.9124 (3.5); 3.9075 (3.5); 3.8946(3.6); 3.8897 (3.5); 3.8769 (1.1); 3.8719 (1.0); 3.5669 (16.0); 2.7704 (10.9); 2.7638 (11.2); 2.7582 (11.4);

2.7516 (10.6); 2.0052(2.4); 1.6077 (2.6); 1.5674 (19.1); 1.5496 (18.6); 0.1463 (0.6); 0.0499 (0.5); 0.0079 (4.9); -0.0002 (154.1); -0.0085 (5.1); -0.1495 (0.6)

Example No. I.1-183:

'H-NMR (400 MHz, CDCI3 δ, ppm) 7.5291 (4.3); 7.5279 (4.4); 7.5197 (0.9); 7.5105 (4.3); 7.5092 (4.4); 7.4048 (7.0); 7.3822 (7.1); 7.3105 (0.7); 7.2607 (111.8); 7.2269 (0.7); 7.2126 (0.8); 6.9967 (0.6); 6.3651 (6.0); 6.3584 (5.8); 6.0674 (0.9); 4.5655 (1.7); 4.5512 (1.2);

4.5276 (4.6); 4.5136 (5.1); 4.4919 (5.7); 4.4887 (5.2); 4.4544 (1.5); 4.4508 (1.8); 3.9521 (0.9); 3.9495 (0.9); 3.9344 (3.2); 3.9316 (3.2); 3.9166 (3.3); 3.9138 (3.2); 3.8987 (1.0);

3.8961 (1.0); 3.5655 (11.1); 3.5624 (16.0); 3.5591 (11.8); 3.3062 (1.0); 3.2920 (1.3); 3.2879 (2.4); 3.2740 (3.4); 3.2696 (2.6); 3.2604 (2.5); 3.2559 (3.4); 3.2423 (2.4); 3.2379 (1.4);

3.2242(1.1); 3.2090 (0.5); 2.0049 (1.9); 1.6934 (1.7); 1.5692 (11.6); 1.5662 (11.8); 1.5514 (11.6); 1.5484 (11.7); 1.1152(7.1); 1.1134(7.2); 1.0970(14.4); 1.0952(14.8); 1.0788 (7.0); 1.0770 (7.1); 0.0080 (1.3); -0.0002 (42.3); -0.0085 (1.4)

Example No. I.1-184:

'H-NMR (400 MHz, CDCI3 δ, ppm) 7.5193 (3.8); 7.5163 (3.4); 7.5007 (3.3); 7.4977 (3.4); 7.4030 (6.1); 7.3804 (6.1); 7.2605 (97.9); 6.9965 (0.5); 6.3586 (7.2); 5.9415 (0.8); 4.5442 (1.7); 4.5297 (1.1); 4.5068 (4.8); 4.4926(5.4); 4.4757 (5.5); 4.4711 (5.0); 4.4385 (1.2); 4.4336 (1.7); 4.0924 (0.7); 4.0892 (0.9); 4.0760 (1.0); 4.0727 (1.5); 4.0695 (0.8); 4.0594 (0.8); 4.0563 (1.5); 4.0530 (1.0); 4.0398 (0.9); 4.0366 (0.7); 3.9694 (1.3); 3.9516 (4.8); 3.9338 (5.0); 3.9160 (1.3); 3.5597(13.2); 2.0044 (0.7); 1.5959 (0.7); 1.5680 (9.9); 1.5640 (10.0); 1.5502 (9.7); 1.5462 (9.7); 1.1309(12.1); 1.1229 (9.3); 1.1131 (16.0); 1.1066(9.3); 1.0957 (8.6); 0.0080 (1.1); -0.0002 (35.1); -0.0085 (1.0)

- 54 042989

Example No. I.1-231:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) δ= 7.5141 (2.0); 7.5116 (1.9); 7.4954 (2.0); 7.4928 (1.9);

7.3690 (2.7); 7.3463 (2.7); 7.2608(35.2); 6.3421(5.3); 4.4087 (0.9); 4.3984 (0.9); 4.3916 (0.5); 4.3812 (1.9); 4.3633 (1.4); 4.3542 (0.6); 4.3461 (1.3); 4.3379 (1.3); 4.3298 (0.7);

4.3214 (0.7); 4.3188 (0.6); 4.3105 (0.6); 3.8958 (0.7); 3.8779 (2.5); 3.8601(2.6); 3.8422 (0.7); 3.5468 (7.9); 2.9592 (12.4); 2.9563 (12.1); 2.9134 (16.0); 2.5657(2.1); 2.5491(4.2); 2.5323 (2.0); 1.5641 (4.9); 1.5242 (5.9); 1.5219 (5.9); 1.5063 (5.9); 1.5040 (5.8); 0.0080 (0.7); -0.0002 (20.1); -0.0085 (0.7)

Example No. I.1-241:

Ή-NMR (400 MHz, CDC13 δ, ppm) 7.6956 (1.7); 7.6767 (1.7); 7.6665 (1.7); 7.6478 (1.6); 7.5187 (0.7); 7.3619 (1.8); 7.3510 (1.8); 7.3391 (1.8); 7.3283 (1.7); 7.2599 (127.1); 6.9958 (0.7); 6.3300 (2.7); 6.3194 (2.8); 4.7569 (0.9); 4.7365 (0.9); 4.7206 (1.6); 4.7002 (1.7);

4.6251 (1.7); 4.6217 (1.8); 4.5889 (1.0); 4.5853 (1.0); 4.0410 (1.5); 4.0242 (1.8); 4.0065 (1.5); 3.5419 (7.8); 3.5390 (8.1); 2.9245 (16.0); 2.9030 (7.7); 2.8991 (7.4); 1.6152 (4.8);

1.6033 (5.2); 1.5972 (5.0); 1.5854 (5.0); 1.5475 (4.8); 1.2553 (0.6); 0.0079 (1.2); -0.0002 (35.0); -0.0085 (1.1)

Example No. I.1-242:

Ή-NMR (400 MHz, CDC13 δ, ppm) 7.7081 (1.6); 7.6892 (1.6); 7.6689 (1.6); 7.6502 (1.6); 7.5188 (0.6); 7.3631 (1.9); 7.3532 (1.7); 7.3402 (1.7); 7.3305 (1.7); 7.2599 (103.8); 6.9959 (0.6); 6.3282 (2.7); 6.3157 (2.6); 4.8718 (0.5); 4.8324 (1.2); 4.8170 (1.4); 4.7909 (1.5);

4.7871 (1.5); 4.7392 (0.6); 4.7346 (0.8); 4.0084 (1.3); 3.9904 (1.4); 3.9877 (1.4); 3.9697 (1.4); 3.7169 (16.0); 3.7149 (14.8); 3.5422 (7.6); 3.5394 (8.1); 3.5110 (0.6); 3.1469 (1.3);

3.1351 (13.9); 3.1168 (1.3); 2.0053 (2.2); 1.6134 (5.0); 1.6027 (5.5); 1.5954 (5.6); 1.5847 (5.6); 1.5771 (1.7); 1.5745 (1.5); 1.5589 (1.1); 1.5565 (1.0); 0.0080 (1.7); -0.0002 (56.2); 0.0085 (1.9)

Example No. I.1-251:

Ή-NMR (400 MHz, CDC13 δ, ppm) 7.5432 (3.2); 7.5322 (3.2); 7.5247 (3.4); 7.5203 (1.2); 7.5137 (6.0); 7.5105 (3.2); 7.4952 (3.0); 7.4918 (2.9); 7.3770 (2.8); 7.3728 (3.0); 7.3615 (3.6); 7.3584 (3.8); 7.3542 (3.2); 7.3501 (3.2); 7.3389 (3.6); 7.3358 (3.7); 7.2727 (0.5);

7.2719 (0.5); 7.2711 (0.6); 7.2703 (0.6); 7.2694 (0.8); 7.2687 (0.9); 7.2679 (1.1); 7.2670 (1.3); 7.2662 (1.7); 7.2654 (2.3); 7.2614 (136.5); 7.2573 (4.1); 7.2565 (3.3); 7.2557 (2.8);

7.2549 (2.4); 7.2541 (2.1); 7.2533 (1.8); 7.2525 (1.5); 7.2517 (1.4); 7.2509 (1.2); 7.2501 (1.1); 7.2493 (1.0); 7.2485 (0.9); 7.2477 (0.9); 7.2469 (0.8); 7.2461 (0.8); 7.2453 (0.7);

7.2445 (0.7); 7.2437 (0.7); 7.2429 (0.7); 7.2421 (0.6); 7.2413 (0.6); 7.2405 (0.6); 7.2397

- 55 042989 (0.6); 7.2389 (0.6); 7.2357 (0.5); 7.2167 (0.5); 6.9973 (0.8); 6.3683 (4.9); 6.3574 (5.3); 6.3518 (5.0); 6.3487 (4.8); 5.7628 (0.8); 5.6816 (1.3); 4.4584 (0.9); 4.4501 (1.0); 4.4306 (1.4); 4.4223 (1.5); 4.4001 (0.7); 4.3914 (0.8); 4.3771 (0.9); 4.3726 (1.9); 4.3671 (1.6);

4.3638 (2.0); 4.3575 (0.8); 4.3495 (1.6); 4.3400 (4.0); 4.3294 (4.4); 4.3181 (2.7); 4.3168 (2.8); 4.3138 (1.5); 4.3053 (2.4); 4.3015 (3.3); 4.2884 (3.0); 4.2777 (0.9); 4.2740 (1.1);

4.2605 (1.0); 4.1304 (0.8); 4.1125 (0.8); 3.8846 (0.7); 3.8665 (2.6); 3.8534 (0.8); 3.8485 (3.0); 3.8461 (3.0); 3.8355 (2.6); 3.8327 (2.9); 3.8280 (3.0); 3.8174 (2.6); 3.8147(2.7);

3.8100 (1.0); 3.7994 (0.8); 3.7968 (0.8); 3.5613 (7.8); 3.5581 (12.0); 3.5549 (16.0); 3.5517 (15.0); 3.5483 (9.2); 3.5468 (8.8); 3.5433 (7.6); 3.2906 (2.5); 3.2760 (3.4); 3.2743(4.2);

3.2703 (2.8); 3.2677(1.9); 3.2545(3.6); 3.2482 (1.2); 3.2287 (1.8); 3.2122 (1.6); 3.1927 (1.2); 3.1861 (0.7); 3.1834 (0.7); 3.1726 (0.8); 3.1699 (0.9); 3.1638 (1.2); 3.1608 (1.0);

3.1548 (0.7); 3.1442 (0.9); 3.1413 (1.0); 3.1346 (0.9); 3.1321 (0.9); 2.6354 (0.9); 2.6259 (1.4); 2.6154 (1.7); 2.6123 (1.7); 2.6029 (1.8); 2.5925 (1.3); 2.5821 (1.0); 2.2307 (0.7);

2.2207 (1.0); 2.2148 (1.0); 2.2109 (0.9); 2.2047 (1.2); 2.2013 (1.2); 2.1973 (1.8); 2.1917 (1.2); 2.1883 (1.4); 2.1819 (1.4); 2.1779 (1.2); 2.1735 (1.4); 2.1686 (1.0); 2.1644 (1.0);

2.1592 (0.8); 2.1547 (0.5); 2.0436 (4.0); 1.9229 (1.0); 1.9104 (0.9); 1.9064 (1.1); 1.9028(1.1); 1.8899 (1.9); 1.8828 (0.7); 1.8778 (0.8); 1.8698 (1.8); 1.8555 (1.4); 1.8501 (0.9);

1.8364 (1.0); 1.5804 (6.6); 1.5558 (10.0); 1.5517 (14.7); 1.5501 (13.5); 1.5378 (10.4); 1.5349 (12.7); 1.5336 (14.7); 1.5320 (13.6); 1.2764 (1.4); 1.2586 (3.3); 1.2407 (1.3); 0.0079 (1.9);

0.0054 (0.5); 0.0046 (0.7); -0.0002 (70.0); -0.0052 (1.9); -0.0060 (1.6); -0.0069 (1.5); -0.0085 (2.7); -0.0116 (0.7); -0.0124 (0.7); -0.0140 (0.6); -0.0148 (0.5)

Example No. I.1-254:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.5189 (1.0); 7.5114 (2.0); 7.4920 (4.5); 7.4774 (2.7); 7.4726 (3.0); 7.4179 (2.4); 7.4094 (2.8); 7.4047 (2.8); 7.3952 (2.7); 7.3867 (2.8); 7.3820 (2.8); 7.2600 (151.9); 6.9959 (0.9); 6.3656 (5.2); 6.3617 (5.0); 6.3577 (4.3); 6.3449 (4.3);

5.6570 (1.2); 5.6283 (1.3); 5.6085 (1.0); 5.5535 (0.9); 5.2761(1.7); 5.2615(3.6); 5.2466 (2.8); 5.2309 (0.7); 4.0852 (0.5); 4.0674(1.9); 4.0543 (2.1); 4.0498 (2.1); 4.0366 (2.0);

4.0192 (0.6); 3.9183 (0.6); 3.9010 (1.9); 3.8980 (1.8); 3.8830 (1.9); 3.8649 (0.6); 3.6418 (1.0); 3.6368 (1.0); 3.6283 (1.1); 3.6235 (1.0); 3.6126 (1.3); 3.6077 (1.3); 3.5994 (2.4);

3.5861 (1.5); 3.5805 (1.6); 3.5629 (14.5); 3.5540 (16.0); 3.5382 (1.6); 3.2446 (1.2); 3.2316 (1.1); 3.2161 (1.1); 3.2023 (1.0); 3.0583 (1.4); 3.0283 (1.3); 3.0107 (1.4); 2.9816 (1.3); 2.6486 (1.2); 2.6324 (1.3); 2.6183 (1.0); 2.6106 (1.2); 2.6026 (2.4); 2.5941 (1.3); 2.5878 (1.6); 2.5737 (1.3); 2.5662 (1.5); 2.5572 (1.3); 2.5498 (1.3); 2.3091 (1.6); 2.2962 (1.6);

2.2619 (2.4); 2.2515(2.4); 2.2190 (1.0); 2.2070 (0.9); 2.0045 (1.9); 1.5459 (12.2); 1.5284 (16.1); 1.5147 (10.1); -0.0002 (54.6)

- 56 042989

Example No. I.1-255:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.5387 (3.0); 7.5194 (4.1); 7.5151 (2.9); 7.4963 (2.7); 7.4766 (3.1); 7.4721 (2.8); 7.4579 (3.3); 7.4534 (3.0); 7.4499 (3.8); 7.4256 (6.8); 7.4021 (3.7); 7.2601 (297.0); 7.2104 (1.1); 6.9961 (1.6); 6.3797 (4.2); 6.3614 (8.0); 6.3448 (5.0); 5.8476 (0.9); 5.7945 (1.7); 5.7683 (0.9); 4.1754 (1.3); 4.1720(1.4); 4.1658(1.5); 4.1619 (1.6); 4.1475 (1.6); 4.1444 (1.8); 4.1379 (1.7); 4.1343 (1.8); 4.0557 (1.1); 4.0475 (1.1); 4.0268 (2.4); 4.0192 (3.4); 4.0023 (5.7); 3.9981 (2.7); 3.9899 (2.2); 3.9846 (5.7); 3.9806 (2.7); 3.9669 (1.7); 3.9628 (2.4); 3.9451 (0.6); 3.8742 (1.7); 3.8711 (1.4); 3.8585 (2.0);

3.8552 (1.7); 3.8459 (1.2); 3.8427 (1.1); 3.8301 (1.5); 3.8269 (1.4); 3.8040 (1.2); 3.7878 (1.7); 3.7750 (1.8); 3.7597 (3.4); 3.7471 (1.0); 3.7318 (2.2); 3.7146 (1.2); 3.7004 (1.9);

3.6932 (1.8); 3.6858 (1.8); 3.6729 (1.2); 3.5652 (7.4); 3.5622 (8.0); 3.5510 (16.0); 2.3759 (0.6); 2.3505 (1.9); 2.3330 (1.9); 2.3255 (1.6); 2.3082 (2.7); 2.3008 (1.3); 2.2949 (2.1);

2.2911 (2.3); 2.2880 (3.1); 2.2834 (2.9); 2.2767 (1.7); 2.2719 (3.3); 2.2700 (3.1); 2.2662 (3.1); 2.2597 (1.1); 2.2555 (1.8); 2.2498 (1.8); 2.2457 (0.8); 2.2413 (0.8); 2.2323 (1.2);

2.2288 (1.5); 2.2226 (1.1); 2.2146 (1.4); 2.2073 (1.5); 2.1976 (1.2); 2.1946 (1.3); 2.1867 (1.4); 2.1788 (1.6); 2.1749 (1.7); 2.1662 (0.7); 2.1623 (0.9); 2.1561 (1.2); 2.0048 (2.3);

1.8045 (0.9); 1.7920 (1.1); 1.7825 (1.2); 1.7791 (1.3); 1.7705 (1.7); 1.7625 (1.8); 1.7549 (1.5); 1.7500 (1.6); 1.7414 (1.3); 1.7331 (1.7); 1.7247 (1.1); 1.7191 (1.0); 1.7147 (1.0);

1.7011 (1.0); 1.6455 (0.6); 1.5524 (8.4); 1.5434 (11.7); 1.5400 (13.3); 1.5347 (9.3); 1.5257 (11.5); 1.5231 (12.6); 0.0080 (3.3); -0.0002 (108.7); -0.0085 (3.3)

Example No. I.1-293:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.4868 (3.5); 7.4794 (3.6); 7.4683 (3.6); 7.4608 (3.6); 7.3655 (4.9); 7.3429 (5.0); 7.2717 (0.5); 7.2709 (0.6); 7.2701 (0.6); 7.2693 (0.7); 7.2685 (0.8); 7.2677 (1.0); 7.2668 (1.1); 7.2660 (1.4); 7.2652 (1.7); 7.2610 (83.8); 6.3517 (7.4); 4.1846(2.8); 4.1835 (2.9); 4.1789 (2.4); 4.1766 (2.6); 4.1654(6.9); 4.1586 (10.2); 4.1520 (4.8); 4.1476 (7.3); 4.1409 (7.2); 4.1298 (2.3); 4.1231 (2.4); 4.1148 (4.2); 4.0992 (3.8); 4.0878 (1.9); 4.0722 (2.1); 3.8702 (0.7); 3.8597 (0.8); 3.8522 (2.9); 3.8418 (3.0); 3.8343 (3.0); 3.8239 (3.8); 3.8160 (1.7); 3.8137 (1.7); 3.8055 (2.1); 3.7945 (2.4); 3.7842 (2.5); 3.7745 (1.9); 3.7654 (1.7); 3.7555 (0.9); 3.5597 (9.4); 3.5565 (13.4); 3.5530 (10.0); 3.4871 (1.3); 3.4804(2.1); 3.4762 (1.1); 3.4737 (1.1); 3.4700 (1.0); 3.4595 (1.8); 3.4572 (1.9);

3.4528 (2.5); 3.4505 (2.7); 3.4464 (1.9); 3.4433 (1.6); 3.4300 (1.4); 3.4233 (1.7); 3.4192 (1.0); 3.4166 (0.8); 3.4130 (0.7); 2.0034 (1.1); 1.9935 (0.8); 1.9785 (2.0); 1.9587 (0.9); 1.9505 (1.3); 1.9448 (1.2); 1.5769 (2.3); 1.5727 (2.3); 1.5679 (2.4); 1.5505 (1.3); 1.5406 (1.5); 1.5308(2.2); 1.5220(13.8); 1.5209(14.0); 1.5041 (14.7); 1.5032(14.4); 1.4960 (1.8); 1.4922 (1.4); 1.4846 (1.2); 1.4686 (1.2); 1.4574 (0.9); 1.2666(7.4); 1.2616 (7.5); 1.2488 (15.7); 1.2439 (16.0); 1.2310 (7.1); 1.2260 (7.3); 0.0080 (1.1); 0.0048 (0.5); 0.0040 (0.7); 0.0002 (32.9); -0.0085 (0.8)

Example No. I.2-2:

Ή-NMR (400 MHz, CDCI3 δ, ppm) 7.6080 (0.6); 7.5183 (1.2); 7.4793 (1.8); 7.4715 (1.8); 7.4607 (2.0); 7.4528 (1.9); 7.3708 (2.0); 7.3670 (2.2); 7.3481 (1.9); 7.3444 (2.2); 7.2787 (0.7); 7.2594 (216.1); 7.2456 (0.6); 7.2081 (0.5); 6.9955 (1.2); 6.3517 (3.5); 6.3483 (3.5); 5.2985 (0.8); 4.3495 (0.8); 4.3427 (0.8); 4.3324 (1.1); 4.3258 (0.9); 4.3111 (1.2); 4.2965 (1.6); 4.2837 (1.0); 4.2683 (0.5); 3.7022 (0.6); 3.6932 (1.0); 3.6737 (2.0); 3.6649 (15.7); 3.6635 (16.0); 3.6403 (0.5); 3.5503 (8.5); 2.5888 (1.5); 2.5804 (1.3); 2.5732 (2.7); 2.5645 (2.0); 2.5576 (1.6); 2.5478 (1.0); 1.9955 (0.5); 1.9763 (0.7); 1.9604 (1.0); 1.9422 (1.2);

1.9226 (0.8); 1.8682 (0.8); 1.8515 (1.2); 1.8332 (1.4); 1.8150 (1.0); 1.7986 (0.6); 1.6535 (1.3); 1.0666 (4.9); 1.0482 (10.7); 1.0298 (4.6); 0.0080 (2.5); -0.0002 (74.9); -0.0085 (2.3)

- 57 042989

Example #1.2-32:

'H-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.5180 (7.0); 7.4695 (2.1); 7.4534 (2.4); 7.4346 (2.0); 7.3794 (1.0); 7.3549 (2.3); 7.3511 (2.6); 7.3322 (3.0); 7.3287 (2.9); 7.2998 (2.8); 7.2966 (3.0); 7.2918 (4.6); 7.2871 (4.9); 7.2839 (5.8); 7.2831 (5.7); 7.2814 (6.8); 7.2807 (7.0);

7.2799 (7.2); 7.2791 (7.5); 7.2783 (8.0); 7.2775 (8.2); 7.2767 (8.8); 7.2759 (9.8); 7.2751 (10.3); 7.2743 (10.8); 7.2735 (11.5); 7.2727 (12.4); 7.2719 (13.3); 7.2711 (14.6); 7.2703 (16.0); 7.2695 (17.6); 7.2687 (19.6); 7.2679 (21.6); 7.2671 (24.0); 7.2663 (27.3); 7.2591 (1212.4); 7.2558 (43.1); 7.2550 (33.0); 7.2542 (26.8); 7.2533 (23.0); 7.2525 (19.8); 7.2517(18.2); 7.2509 (16.2); 7.2501 (14.8); 7.2493 (13.7); 7.2485 (12.7); 7.2477 (12.1); 7.2469 (11.5); 7.2462 (10.9); 7.2454 (10.1); 7.2446 (9.6); 7.2437 (9.1); 7.2430 (8.8); 7.2421 (8.4);

7.2414 (8.5); 7.2406 (7.9); 7.2398 (7.6); 7.2390 (7.4); 7.2382(7.2); 7.2374 (6.9); 7.2366 (6.8); 7.2358 (6.8); 7.2350 (6.8); 7.2342(6.4); 7.2334 (6.4); 7.2318 (6.4); 7.2295 (5.8);

7.2247(6.6); 7.2152 (5.8); 7.2087 (6.5); 7.1400 (2.6); 7.1170 (1.5); 6.9951 (6.9); 6.3501 (3.5); 6.2796 (0.8); 4.1771(1.4); 4.1667(1.6); 4.1503 (2.2); 4.1399 (2.4); 4.0479 (2.4);

4.0268 (2.3); 4.0212 (1.7); 4.0001 (1.8); 3.6845 (1.1); 3.6678 (2.1); 3.6382 (15.7); 3.6327 (16.0); 3.5539 (6.0); 3.5505 (6.1); 3.5192 (1.5); 2.0048(2.0); 1.9486 (1.0); 1.9295 (1.2);

1.9091 (0.8); 1.8721 (0.8); 1.8539(1.2); 1.8377(1.5); 1.8191 (1.0); 1.5275 (180.9); 1.2545 (1.0); 1.1668 (11.1); 1.1643 (10.5); 1.1383 (10.9); 1.1361 (10.9); 1.0508 (4.6); 1.0325 (9.5); 1.0141 (4.1); 0.1459 (1.6); 0.0365 (1.0); 0.0142 (4.2); 0.0079 (19.7); 0.0062 (12.4); 0.0046 (20.3); -0.0002 (470.3); -0.0052 (13.0); -0.0060 (11.4); -0.0068 (10.5); -0.0085 (18.6); 0.0116 (5.8); -0.0123 (5.6); -0.0179 (3.9); -0.0235 (3.2); -0.0275 (2.9); -0.0346 (2.9); -0.0498 (2.8); -0.1495 (2.0)

Example #1.2-46:

'H-NMR (400 MHz, CDC1 ₃ δ, ppm) δ= 7.3818 (0.6); 7.3633 (0.8); 7.3519 (0.6); 7.3461 (1.8); 7.3427 (1.9); 7.3378 (0.8); 7.3236 (1.8); 7.3214 (1.5); 7.2593 (69.0); 6.3157 (0.8); 6.2865 (0.8); 5.1265 (2.2); 4.0533 (0.5); 4.0400 (0.6); 3.5182 (1.2); 3.5154 (1.3); 3.4994 (1.2);

3.4965 (1.2); 2.0046 (0.8); 1.5337 (16.0); 1.1242(1.3); 1.1057 (2.7); 1.0872 (1.2); 0.0079 (1.2); -0.0002 (34.5); -0.0085 (1.3)

Example #1.4-43:

'H-NMR (400 MHz, CDC13 δ, ppm) 7.5932 (0.5); 7.3734 (0.5); 7.3507 (0.5); 7.2646 (0.6); 7.2597 (46.5); 6.3405 (1.1); 4.5843 (0.7); 4.5710 (0.8); 4.5270 (0.8); 4.5203 (0.7); 4.1612 (0.8); 4.1433 (0.8); 3.5481 (1.8); 3.5444 (1.4); 1.5388 (16.0); 1.2627 (1.2); 1.2613 (1.3);

1.2448 (2.4); 1.2434 (2.6); 1.2269(1.1); 1.2255 (1.2); 0.9781 (1.2); 0.9754 (1.4); 0.9678 (2.3); 0.9619 (1.4); 0.9591 (1.4); 0.9518 (2.0); 0.0079 (0.6); -0.0002 (19.5); -0.0085 (0.6)

Example #1.5-2:

'H-NMR (400 MHz, CDC13 δ, ppm) δ= 7.5185 (1.0); 7.3596 (0.7); 7.3566 (0.5); 7.3370 (0.6); 7.3340 (0.5); 7.2742 (0.5); 7.2734 (0.5); 7.2726 (0.6); 7.2718 (0.6); 7.2710 (0.7); 7.2702 (0.8); 7.2694 (0.9); 7.2686 (1.1); 7.2678 (1.2); 7.2670 (1.4); 7.2662 (1.6); 7.2654 (2.0);

7.2645 (2.4); 7.2597 (179.3); 7.2524 (1.0); 7.2516 (0.7); 7.2508 (0.6); 7.2500 (0.6); 7.2492 (0.6); 6.9956 (1.0); 6.3475 (1.2); 6.3434 (1.2); 3.6602(6.4); 3.6584 (4.5); 3.6438 (0.5);

3.6403 (0.5); 3.5469 (3.0); 2.5634 (0.8); 2.5557 (0.6); 1.5338 (16.0); 1.1284 (2.2); 1.1114 (2.1); 1.0391 (1.2); 1.0222 (1.2); 0.9467 (0.7); 0.9362 (1.1); 0.9281 (1.4); 0.9177 (2.4);

0.9096 (0.6); 0.8991 (0.9); 0.1263 (0.5); 0.0080 (2.3); -0.0002 (79.6); -0.0085 (2.2)

Example #1.5-3:

'H-NMR (400 MHz, CDC13 δ, ppm) δ= 7.2694 (0.5); 7.2686 (0.6); 7.2678 (0.7); 7.2670 (0.7) 7.2662 (0.9); 7.2654 (1.0); 7.2646(1.2); 7.2638 (1.6); 7.2597 (83.0); 7.2557 (1.6); 7.2549 (1.2); 7.2540 (0.9); 7.2532 (0.7); 7.2524 (0.6); 6.3458 (0.6); 6.3403 (0.6); 5.2988 (16.0);

4.1258 (0.6); 4.1080 (0.6); 3.5457 (1.4); 2.0439 (0.8); 1.5355 (12.5); 1.2591 (1.2); 1.2429 (1.6); 1.2414 (1.8); 1.2238 (0.8); 1.1266 (1.0); 1.1097 (1.0); 1.0394 (0.6); 1.0227 (0.6);

0.9344 (0.6); 0.9260 (0.7); 0.9159 (1.1); 0.8973 (0.5); 0.0080 (1.0); -0.0002 (36.9); -0.0085 (1.0)

-58042989

Example No. I.8-2:

Ή-NMR (400 MHz, CDC13 δ, ppm) 7.5184 (1.0); 7.4121(2.2); 7.3938 (2.2); 7.3592 (2.3); 7.3367 (2.3); 7.3105 (0.8); 7.2596(173.6); 6.9956 (1.0); 6.3545 (3.5); 5.2986 (1.2); 4.3769 (2.3); 4.3612 (4.6); 4.3456 (2.4); 3.6752 (16.0); 3.6351 (9.4); 3.5541(5.3); 3.5510 (5.6);

2.6266 (2.1); 2.6109 (4.1); 2.5952 (2.0); 1.5836 (5.4); 0.0079 (2.0); -0.0002 (64.9); -0.0085 (2.1)

Example #1.8-3:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) δ= 7.4172 (3.9); 7.3989 (3.9); 7.3582 (4.0); 7.3356 (4.0); 7.2616 (8.1); 6.3525 (6.8); 4.3777 (3.8); 4.3620 (7.9); 4.3462 (4.1); 4.1567 (2.1); 4.1389 (6.4); 4.1210 (6.5); 4.1032 (2.2); 3.6349 (16.0); 3.5526 (10.3); 3.5498 (11.0); 2.6123 (3.9); 2.5966 (7.7); 2.5809 (3.8); 1.5637 (0.6); 1.2689 (7.0); 1.2511 (14.2); 1.2332 (7.1); -0.0002 (10.4); -0.0083 (0.6)

Example No. I.8-23:

Ή-NMR (400 MHz, CDC13 δ, ppm) 7.5182 (2.3); 7.4130 (1.7); 7.4059 (1.8); 7.3948 (1.9); 7.3878 (1.8); 7.3489 (2.8); 7.3262 (2.9); 7.2969 (0.5); 7.2929 (0.7); 7.2825 (0.7); 7.2802 (0.9); 7.2785 (0.9); 7.2778 (0.9); 7.2762 (1.1); 7.2754 (1.3); 7.2746 (1.3); 7.2738 (1.4); 7.2730 (1.5); 7.2722 (1.6); 7.2714 (1.8); 7.2706 (1.9); 7.2698 (2.2); 7.2690 (2.5); 7.2682 (2.7); 7.2674 (3.2); 7.2666 (3.6); 7.2657 (4.3); 7.2594 (419.5); 7.2544 (10.8); 7.2536 (9.1); 7.2528 (7.8); 7.2520 (6.7); 7.2512 (5.9); 7.2504 (5.3); 7.2496 (4.8); 7.2488 (4.5); 7.2480(4.2); 7.2472 (4.0); 7.2464 (3.7); 7.2456 (3.6); 7.2448 (3.4); 7.2440 (3.3); 7.2432 (3.0); 7.2424 (2.9); 7.2416 (3.0); 7.2408 (2.8); 7.2400 (2.8); 7.2393 (2.6); 7.2384 (2.5); 7.2376 (2.5); 7.2369 (2.4); 7.2360 (2.3); 7.2352 (2.3); 7.2345 (2.2); 7.2337 (2.0); 7.2329 (1.9); 7.2321 (2.0); 7.2313 (1.9); 7.2305 (1.8); 7.2297 (1.8); 7.2289 (1.8); 7.2273 (1.7); 7.2249 (1.6); 7.2233 (1.6); 7.2209 (1.6); 7.2091 (1.4); 7.1971 (1.0); 7.1875 (0.8); 6.9953 (2.4); 6.3494 (3.8); 5.3010 (0.6); 5.2853 (1.0); 5.2666 (1.0); 5.2512 (0.6); 4.1250 (1.4); 4.1070 (4.3); 4.0898 (4.4); 4.0719 (1.5); 3.6193 (4.9); 3.6167 (8.6); 3.6149 (5.4); 3.5518 (8.0); 3.5487 (8.3); 2.6314 (0.9); 2.6123 (1.0); 2.5923 (1.6); 2.5735 (1.5); 2.4920 (1.3); 2.4887 (1.3); 2.4781 (1.4); 2.4746 (1.4); 2.4530 (0.8); 2.4497 (0.8); 2.4390 (0.8); 2.4356 (0.8);

1.5403 (24.9); 1.2712 (7.0); 1.2696 (7.2); 1.2554 (7.2); 1.2537 (7.5); 1.2493 (8.4); 1.2314 (16.0); 1.2135 (7.6); 0.0080 (4.6); -0.0002 (161.4); -0.0085 (6.1); -0.1496 (0.6)

Example No. I.8-42:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.5102 (2.3); 7.4919 (2.3); 7.3576 (2.4); 7.3350 (2.4); 7.2601(38.9); 6.3459 (3.9); 4.7512 (1.0); 4.7495 (0.9); 4.6549 (1.3); 4.6400 (8.5); 3.7478 (2.6); 3.7399 (9.6); 3.7086 (16.0); 3.5515 (5.3); 3.5484 (5.5); 3.5451(2.6); 3.5406 (1.0); 0.0002 (14.5)

Example #1.8-43:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) δ= 7.5170 (2.5); 7.4983 (2.1); 7.3530 (2.3); 7.3303 (2.3); 7.2929 (0.6); 7.2594(225.1); 7.2091 (1.2); 6.9954 (1.3); 6.3409 (3.7); 5.2985 (0.7); 4.6242 (8.9); 4.1858 (1.0); 4.1679 (3.2); 4.1500 (3.3); 4.1321 (1.2); 3.7409 (8.7); 3.5498 (5.6);

3.5469 (5.6); 1.5667 (16.0); 1.2715 (3.8); 1.2536(7.9); 1.2358 (3.8); 0.0080 (2.7); -0.0002 (81.2); -0.0084 (3.3)

Example No. I.8-127:

Ή-NMR (400 MHz, CDC13 δ, ppm) 7.3850 (1.1); 7.3669 (1.1); 7.3494 (1.2); 7.3269 (1.2); 7.2604(21.7); 6.3480 (1.8); 5.5276 (0.5); 5.5117(0.8); 5.4959 (0.5); 3.6477 (16.0); 3.6211 (4.4); 3.5497 (2.6); 3.5467 (2.7); 2.6947 (3.5); 2.6786 (3.4); 1.5467 (6.4); -0.0002 (7.9)

Example No. I.11-3:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.5184 (1.8); 7.4851 (2.1); 7.4820 (2.1); 7.4664 (2.1); 7.4632 (2.1); 7.3719 (3.5); 7.3490 (3.6); 7.2854 (0.6); 7.2781 (0.8); 7.2773 (0.8); 7.2741 (1.1); 7.2717 (1.5); 7.2710 (1.5); 7.2701 (1.7); 7.2693 (1.9); 7.2686 (2.1); 7.2669 (2.7);

7.2595 (328.4); 6.9955 (1.8); 4.3477 (0.6); 4.3375 (1.4); 4.3323 (0.6); 4.3220 (1.7); 4.3195 (1.7); 4.3086 (1.5); 4.3046 (1.5); 4.2928 (2.7); 4.2810 (0.6); 4.2771 (1.5); 4.2652 (0.9);

4.2495 (0.5); 4.1496 (1.6); 4.1319 (4.8); 4.1140 (4.8); 4.0964 (1.6); 3.8979 (0.6); 3.8815 (2.0); 3.8799 (2.0); 3.8636 (2.1); 3.8620 (2.0); 3.8457 (0.6); 3.5516 (2.9); 3.5463 (8.0);

- 59 042989

3.5409 (8.2); 3.5354 (2.9); 2.5736 (1.2); 2.5580 (3.2); 2.5429 (2.8); 2.5280 (0.9); 2.5249 (0.9); 2.2496 (1.7); 2.2404 (4.6); 2.2381 (4.9); 2.2289 (4.9); 2.2266 (4.9); 2.2174 (1.7);

2.2150 (1.7); 2.0243 (0.7); 1.5864 (8.3); 1.5167 (10.9); 1.4989 (10.7); 1.2713 (0.6); 1.2634(7.8); 1.2567 (0.9); 1.2455 (16.0); 1.2277 (7.6); 0.0080 (4.5); 0.0057 (1.8); 0.0048 (2.1); -

0.0002 (147.0); -0.0085 (3.9)

Example No. I.46-2:

Ή-NMR (400 MHz, CDC1 ₃ δ, ppm) 7.5387 (2.2); 7.5193 (2.4); 7.4067 (2.2); 7.3836 (2.3);

7.2596 (84.2); 6.3496 (3.7); 4.3413 (2.0); 4.3253 (4.5); 4.3094 (2.2); 3.6677 (16.0); 3.5559(5.4); 3.5530 (5.6); 2.6364 (2.0); 2.6204(4.2); 2.6044 (2.0); 1.5380 (2.6); 1.5245 (11.2);

1.5202 (11.2); 0.0080 (1.0); -0.0002 (31.3); -0.0084 (0.9)

The present invention further provides for the use of one or more compounds of formula (I) according to the present invention and/or their salts as defined above, preferably in the configuration identified as being preferred or especially preferred, in particular one or more compounds of formula (I. 1)-(I.50) and/or their salts, as defined above in each case, as a herbicide, preferably for agricultural crops of useful plants and/or ornamental plants.

The present invention further provides a method for controlling pests, characterized in that an effective amount of one or more compounds of formula (I) in accordance with the present invention and/or salts thereof, as defined above, preferably in the configuration identified as preferred or especially preferred, in in particular, one or more compounds of formulas (I.1)-(I.50) and/or their salts, as defined above in the case of each, or the compositions of the present invention, as defined below, are applied to (harmful) plants, seeds (harmful) plants, soil in or on which (harmful) plants grow, or crop area.

The present invention also provides a method for controlling unwanted plants, preferably crops of useful plants, characterized in that an effective amount of one or more compounds of formula (I) and/or salts thereof, as defined above, preferably in the configuration identified as preferred or especially preferred , in particular one or more compounds of formulas (I.1)-(I.50) and/or their salts, as defined above in the case of each, or the compositions of the present invention, as defined below, are applied to undesirable plants (for example , harmful plants such as monocotyledonous or dicotyledonous weeds or undesirable crop plants), undesirable plant seeds (i.e. plant seeds, e.g. grains, seeds or vegetative propagating organs such as tubers or shoot parts with buds), soil, in or on which unwanted plants grow (e.g. arable land or non-arable land), or crop area (i.e. e. area where unwanted plants will grow).

Also further contemplated are methods for controlling the growth regulation of plants, preferably useful plants, characterized in that an effective amount of one or more compounds of formula (I) and/or salts thereof, as defined above, preferably in the configuration identified as preferred or particularly preferred, in in particular, one or more compounds of formulas (I.1)-(I.50) and/or their salts, as defined above in the case of each, or the composition of the present invention, as defined below, is applied to a plant, plant seed (t e. the seeds of a plant, e.g. grains, seeds or vegetative propagation organs such as tubers or parts of shoots with buds), the soil in or on which the plants grow (e.g. arable land or non-arable land), or area under crop (i.e. . area on which plants will grow).

In such a case, the compounds of the present invention or the compositions of the present invention may be used, for example, by means of pre-plant treatment (perhaps even by application to the soil), pre-emergence and/or post-emergence treatments. Specific examples of certain monocotyledonous and dicotyledonous weed flora that can be controlled with the compounds of the present invention are provided below, without being limited to the listing of specific species.

In the method for controlling harmful plants or regulating plant growth in accordance with the present invention, preference is given to the use of one or more compounds of formula (I) and/or salts thereof for controlling harmful plants or for regulating the growth of useful plants or ornamental plants in agricultural crops, while useful plants or ornamental plants in a preferred configuration are transgenic plants.

The compounds of formula (I) according to the present invention and/or their salts are suitable for the control of the following genera of monocot and dicot pests.

Monocotyledonous harmful plants of the genus Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena,

- 60 042989

Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. Dicotyledonous plants of the genus Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

If the compounds of the present invention are applied to the soil surface before the germination of harmful plants (weeds and/or broadleaf weeds) (pre-emergence treatment method), the emergence of weeds and/or sprouts of broadleaf weeds is completely prevented, or weeds grow until then until they reach the cotyledon stage, but then they stop growing and eventually die completely after three to four weeks.

If the active ingredients are applied after emergence to the green parts of plants, growth stops after treatment and the harmful plants remain in the growth stage at the time of application, or they die completely after a certain time, so that competition from weeds that are harmful to cultivated plants, due to this, it is eliminated very early and for a long time.

Although the compounds of the present invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, such as dicotyledonous crops of the genus Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia or monocot crops of the genus Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea will only be slightly damaged , if at all, depending on the structure of the particular compound of the present invention and the rate of its application. For these reasons, the compounds of the present invention have a very good suitability for the selective growth control of undesirable plants among plant crops, such as agriculturally useful plants or ornamental plants grown in plantations.

In addition, the compounds of the present invention (depending on their specific structure and applied rate of application) have excellent properties in relation to the regulation of growth in crop plants. They interfere with the plant's own metabolism with a regulating effect and can thus be used to control plant components and facilitate harvesting, for example by causing desiccation and stunting. In addition, they are also suitable for the general control and suppression of unwanted vegetative growth without destroying the plants. The suppression of vegetative growth plays a key role in many mono- and dicotyledonous crops because, for example, it can reduce or completely prevent lodging.

Due to their herbicidal and plant growth regulating properties, the active ingredients can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, transgenic plants are characterized by specific advantageous properties, such as resistance to certain pesticides, in particular certain herbicides, resistance to plant diseases or pathogens that cause plant diseases, such as certain insects or microorganisms, such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the collected material in terms of quantity, quality, storage stability, composition and specific components. For example, transgenic plants are known with increased starch content or altered starch quality or different fatty acid composition of harvested material.

With regard to transgenic crops, preference is given to the use of the compounds of the present invention and/or salts thereof in economically important transgenic crops of useful plants and ornamental plants, for example cereals such as wheat, barley, rye, oat varieties, millet/sorghum, rice. and corn, or, otherwise, crops - sugar beets, cotton, soybeans, oilseed rape, varieties of potatoes, tomatoes, peas and other vegetables. The compounds of the present invention can also preferably be used as herbicides in useful plant crops that are resistant, or have become resistant by recombinant means, to the phytotoxic effects of the herbicides.

Due to their herbicidal and plant growth regulating properties, the active ingredients can also be used to control harmful plants in crops of genetically modified plants that are known or not yet developed. In general, transgenic plants are characterized by specific advantageous properties, such as resistance to certain pesticides, in particular certain herbicides, resistance to plant diseases or pathogens that cause plant diseases, such as certain insects or microorganisms, such as fungi, bacteria or viruses.

Other specific characteristics relate, for example, to the collected material in terms of quantity, quality, storage stability, composition and specific components. For example, transgenic plants are known with increased starch content or altered starch quality or different fatty acid composition of harvested material. Other specific properties may be tolerance or resistance to abiotic stress factors, such as heat, cold, drought, salinity and ultraviolet radiation.

Preference is given to the use of the compounds of formula (I) according to the present invention or their salts in economically important transgenic agricultural crops of useful plants and ornamental plants, for example cereals such as wheat, barley, rye, oat varieties, triticale, millet/sorghum, rice, cassava and corn, or, otherwise, crops - sugar beets, cotton, soybeans, oilseed rape, varieties of potatoes, tomatoes, peas and other vegetables.

The compounds of formula (I) may preferably be used as herbicides in crops of useful plants which are resistant, or have acquired resistance by recombinant means, to the phytotoxic effects of the herbicides.

Conventional methods for producing new plants that have modified properties compared to existing plants include, for example, conventional cultivation methods and the production of mutants. Alternatively, new plants with altered properties can be obtained using recombinant methods.

The person skilled in the art is aware of numerous molecular biology techniques by which new transgenic plants with modified properties can be obtained. For such recombinant manipulations, nucleic acid molecules that allow mutagenesis or sequence change by recombination of DNA sequences can be introduced into plasmids. Using standard methods, for example, base substitutions can be made, portions of sequences removed, or natural or synthetic sequences added. To connect DNA fragments to each other, adapters or linkers can be added to the fragments.

For example, the production of plant cells with reduced gene product activity can be achieved by expressing at least one appropriate antisense RNA, a sense RNA to achieve a co-suppression effect, or by expressing at least one suitably designed ribozyme that specifically cleaves transcripts of said gene product.

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

When nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any desired compartment of the plant cell. However, in order to achieve localization in a particular compartment, one can, for example, attach a coding region to DNA sequences that provide localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). Nucleic acid molecules can also be expressed in plant cell organelles.

Transgenic plant cells can be regenerated by known techniques to obtain whole plants. As such, the transgenic plants may be plants of any desired plant species, ie not only monocots but also dicots.

In this way, transgenic plants can be obtained having properties altered by overexpression, suppression or silencing of homologous (=natural) genes or gene sequences or by the expression of heterologous (=foreign) genes or gene sequences.

Compounds (I) according to the present invention can preferably be used in transgenic crops that are resistant to growth regulators, such as dicamba, or herbicides that inhibit vital plant enzymes, such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS ) or hydroxyphenylpyruvate dioxygenase

- 62 042989 (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and similar active ingredients.

When the active ingredients of the present invention are used in transgenic crops, they not only have effects on harmful plants that are observed in other crops, but often also effects that are specific to the application in a particular transgenic crop, for example, an altered or specifically enhanced the range of weeds that can be controlled, the modified application rates that can be used for application, preferably good compatibility with herbicides to which the transgenic crop is resistant, and the effect on the growth and yield of the transgenic crop.

The present invention therefore also provides for the use of the compounds of formula (I) according to the present invention and/or their salts as herbicides for the control of harmful plants in crops of useful plants or ornamental plants, if necessary in transgenic crops.

Preference is given to use in cereals, preferably corn, wheat, barley, rye, oat varieties, millet/sorghum or rice before or after emergence

Preference is also given to soybeans before or after emergence.

The use according to the present invention for the control of harmful plants or for the regulation of plant growth also includes the case in which the active ingredient of formula (I) or its salt is formed only after being placed on the plant, in the plant or in the soil from the precursor substance (prodrug). The present invention also provides for the use of one or more compounds of formula (I) or their salts or compositions in accordance with the present invention (as defined below) (in a method) for the control of harmful plants or the regulation of plant growth, where an effective amount of one or more compounds of formula ( I) or their salts is applied to plants (harmful plants, if necessary together with cultivated plants), seeds of plants, soil in which or on which plants grow, or cultivated area.

The present invention also provides a herbicidal composition characterized in that the composition comprises one or more compounds of formula (I) and/or their salts as defined above, preferably in the configuration identified as preferred or particularly preferred, in particular one or more compounds of formula (I. 1)-(I.XX) and/or salts thereof, as defined above for each, and one or more formulation aids traditionally used for crop protection.

In some cases, the composition may also contain one or more additional active agrochemical ingredients, preferably selected from the group consisting of insecticides, acaricides, nematicides, additional herbicides (i.e. those that do not correspond to the above formula (I)), fungicides, safeners , fertilizers and/or additional growth regulators.

The additional active agrochemical ingredients of component (i) of the composition of the present invention are preferably selected from the group of substances specified in The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

The herbicidal composition of the present invention preferably contains one, two, three or more formulation aids that are conventional for crop protection, selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, pulverizing agents, carriers which are solid at 25°C and 1013 mbar, preferably adsorbent granular inert materials, wetting agents, antioxidants, stabilizers, buffering agents, defoamers, water, organic solvents, preferably organic solvents, which are miscible with water in any necessary ratio at 25°C and 1013 mbar.

Compounds (I) according to the present invention can be used as wettable powders, emulsifiable concentrates, spray solutions, powders or granules in conventional formulations. Therefore, the present invention also provides herbicidal compositions and compositions for regulating plant growth, containing compounds of formula (I) and/or their salts.

The compounds of formula (I) and/or their salts can be formulated in various ways according to the required biological and/or physico-chemical 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-based or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting powders (DP), seed dressing formulations, granules for spreading and soil application, granules (GR) in form

- 63 042989 microgranules, sprayable granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These particular types of 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, in: Watkins, Handbook of Insecticide Dust Diluents and Carriers, 2nd ed ., Darland Books, Caldwell N.J., H.v. Olphen, Introduction to Clay Colloid Chemistry; 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, Solvents Guide; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, Grenzflachenaktive Athylenoxidaddukte [Interface-Active Ethylene Oxide Products], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Kuchler, Chemische Technologie [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th ed. 1986.

Wettable powders are preparations which are uniformly dispersed in water and, in addition to the active ingredient, in addition to a diluent or inert substance, also contain ionic and/or nonionic surfactants (wetting agents, dispersing agents), e.g. polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ether sulfates, alkane sulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or, alternatively, sodium oleoylmethyl taurate. Wettable powders are prepared by finely grinding the herbicidal active ingredients, for example, in conventional devices such as hammer mills, blower mills and air jet mills, and simultaneously or sequentially mixing with formulation aids.

Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene, or otherwise relatively high boiling aromatics or hydrocarbons or mixtures of organic solvents, with the addition of one or more ionic and/or nonionic surfactants. (emulsifiers). Examples of emulsifiers that can be used are: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate or non-ionic emulsifiers such as polyglycol fatty acid esters, alkylaryl polyglycol ethers, polyglycol fatty alcohol ethers, propylene oxide-ethylene oxide condensates, alkyl polyethers, sorbitan esters, eg sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, eg polyoxyethylene sorbitan fatty acid esters.

Powders for dusting are prepared by grinding the active ingredient with finely divided solids, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water or oil based. They can be obtained, for example, by wet grinding with commercial bead mills and the optional addition of surfactants, as already listed above, for example, for other types of formulations.

Emulsions, such as oil-in-water (EW) type emulsions, can be prepared, for example, using agitators, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants, as already listed above, for example, for other types of compounds.

Granules can be prepared either by spraying the active ingredient onto an absorbent granular inert material, or by applying concentrates of the active ingredient to the surface of carriers such as sand, kaolinites or granular inert material using adhesives such as polyvinyl alcohol, sodium polyacrylate or otherwise case, mineral oils. Suitable active ingredients can also be granulated in the manner conventional for the preparation of fertilizer granules, if desired as a mixture with fertilizers.

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

For plate granulator, fluid bed, extruder, and spray granulation, see, for example, methods in Spray Drying Handbook 3rd Ed. 1979, G. Goodwin Ltd., London, J.E. Browning, Agglomeration, Chemical and Engineering 1967, pp. 147ff; Perry's Chemical Engineer's Handbook, 5th ed., McGraw-Hill, New York 1973, pp. 8-57.

For more information on the formulation of crop protection compositions, see, for example, G.C. Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, Weed Control Handbook, 5th Ed., Blackwell

- 64 042989

Scientific Publications, Oxford, 1968, pp. 101-103.

The agrochemical preparations, preferably the herbicidal or plant growth regulating compositions of the present invention preferably contain in total from 0.1 to 99% by weight, preferably from 0.5 to 95% by weight, more preferably from 1 to 90% by weight, especially preferably from 2 to 80% by weight of the active ingredients of formula (I) and their salts.

In wettable powders, the concentration of the active ingredient is, for example, from about 10 to 90% by weight, with the remainder up to 100% by weight consisting of conventional formulation components. In emulsifiable concentrates, the concentration of the active ingredient may be from about 1 to 90% and preferably from 5 to 80% by weight. Formulations in dustable form contain from 1 to 30% by weight of the active ingredient, preferably usually from 5 to 20% by weight of the active ingredient; spray solutions contain from 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 amount of active ingredient depends in part on whether the active compound is in liquid or solid form and on which granulation aids, excipients, etc. are used. In water-dispersible granules, the active ingredient content is, for example, from 1% to 95% by weight, preferably from 10 to 80% by weight.

In addition, said active ingredient formulations optionally contain appropriate conventional adhesives, wetting agents, dispersants, emulsifiers, penetration enhancers, preservatives, antifreezes and solvents, fillers, carriers and colorants, defoamers, evaporation retarders, and pH and viscosity modifiers. Examples of formulation aids are described, inter alia, in Chemistry and Technology of Agrochemical Formulations, ed. D. A. Knowles, Kluwer Academic Publishers (1998).

The compounds of formula (I) or their salts can be used alone or in combination in the form of preparations (compositions) based on them with other substances with pesticidal activity, for example, insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or regulators growth, for example, in the form of a finished composition or in the form of tank mixes. Combined formulations can be obtained in this case based on the above formulations, taking into account the physical properties and stability values of the active ingredients to be combined.

Components for forming a combination applicable with the compounds of formula (I) according to the present invention in mixed formulations or tank mix are, for example, known active ingredients whose action is based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase , enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.

Of particular interest is the selective control of harmful plants in agricultural crops of useful plants and ornamental plants. Although the compounds (I) according to the present invention already have very good or proper selectivity for many crops, phytotoxicity to crops could theoretically occur in the case of some crops and in particular in the case of mixtures with other herbicides which are less selective. . Of particular interest in this respect are combinations of compounds (I) according to the present invention which contain compounds (I) or combinations thereof with other herbicides or pesticides and safeners. Antidotes used at antidote levels reduce the phytotoxic side effects of the herbicides/pesticides used, for example in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet/sorghum), sugar beet, sugar cane, oilseed rape, cotton and soybeans, preferably cereals.

The weight ratios of herbicide (mixture) and safener generally depend on the rate of application of the herbicide and the effectiveness of the respective safener and may vary within wide limits, for example in the range from 200:1 to 1:200, preferably from 100:1 to 1:100, especially from 20 :1 to 1:20. Antidotes can be formulated in a similar manner to compounds (I) or mixtures thereof with additional herbicides/pesticides and can be provided and applied as a ready-made formulation or tank mix with herbicides.

For use, herbicide or herbicide safener formulations in commercial form are diluted, if necessary, in the conventional manner with water, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Dusting formulations, soil or spreading granules, and spray solutions are generally not further diluted with additional inerts prior to use.

External conditions such as temperature, humidity, etc., to some extent affect the application rate of the compounds of formula (I) and/or their salts. The rate of application can vary widely

- 65 042989 within. When used as a herbicide for pest control, the total amount of the compounds of formula (I) and their salts is preferably in the range of 0.001 to 10.0 kg/ha, preferably in the range of 0.005 to 5 kg/ha, more preferably in the range of 0.01 to 1.5 kg/ha, particularly preferably in the range of 0.05 to 1 kg/ha. This applies to both pre- and post-emergence applications.

When the compounds of formula (I) and/or their salts are used as plant growth regulators, for example as a stem shortening agent in the case of cultivated plants as mentioned above, preferably in the case of cereal plants such as wheat, barley, rye, triticale , millet/sorghum, rice or corn, the total application rate is preferably in the range of 0.001 to 2 kg/ha, preferably in the range of 0.005 to 1 kg/ha, especially in the range of 10 to 500 g/ha, most preferably in the range from 20 to 250 g/ha. This applies to both pre- and post-emergence applications.

Use as a stem shortening agent can be carried out at various stages of plant growth. Preference is given, for example, to application after tillering at the beginning of linear growth.

An alternative option for use as a plant growth regulator is also seed treatment, which involves various seed dressing and coating techniques. The rate of application depends on the individual methods and can be established in preliminary tests.

The combination forming components applicable with the compounds of formula (I) according to the present invention in the compositions of the present invention (for example, mixed formulations or tank mix) are, for example, known active ingredients whose action is based on inhibition, for example, Acetolaktatsintase, acetyl-soo-carboxylase, cellulososyntase, nolpirovichikimat-3-phosphatase, glutaminsyntase, p-hydroxyphenilpyuruvatexygenase, phytoenesiac, photosystems II, protoportfirinogenoxids, as described, for example, in WEEDD, in WEED Research 26 (1986) 441-445 or The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein. By way of example, known herbicides or plant growth regulators which may be combined with the compounds of the present invention are indicated hereinafter, with the designation of such active ingredients either by their common name in English in accordance with the rules of the International Organization for Standardization (ISO), or chemical name or code number. They always include all forms for use, such as acids, salts, esters, as well as all isomeric forms such as stereoisomers and optical isomers, even if not explicitly stated.

Examples of such herbicidal components to form a mixture are: acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxidim, alloxidim-sodium, ametrin, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4- chlorine-2-fluor-3-methylphenil) -5 phutorpyridine-2-carbon acid, aminocyclopyrylor, aminocyclopyrylor-kali, aminocyclopyrylor-methyl, aminopiralide, aminopiralide, ammonium sulfamate, anilophos, asulas, atrazine, azafenidine, azifururus, beflubutamide , Benazolin, Benazolin -ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazon, benzobicyclone, benzofenap, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromophenoxime, bromoxynil, bromoxynil-but irat, - potassium, -heptanoate and -octanoate, buzoxynone, butachlor, butafenacil, butamiphos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac sodium, chlorfenprop, chlorflurenol, chlorph lurenol- methyl, chloridazone, chlorimuron, chlorimuron-ethyl, chlorphthalim, chlortoluron, chlortaldimethyl, chlorsulfuron, cinidon, cynidone-ethyl, cinmethylin, cinosulfuron, claciphos, cletodym, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, clo ransulammethyl, cumiluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cyclooxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-O-butotyl, -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dimron), dalapon, dazomet, n-decanol, desmedifam, detosyl pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5- dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3one, dichlorprop, dichlorprop-R, diclofop, diclofop-methyl, diclofop-R-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate , dimetamlor, dimetometrin, dimetenamide, dimetenamide-r, dimetrisulfuron, dinitramine, dinothel, diphenamide, savage, di-dibromide, diopier, diuron, dnoc, endol, Erts, Esprokarb, thief, this meter-meter, etomittsulfuron-meals, ethi-mein, ethi-mein, ethiozin, ethiozin, ethiozin. This is fumesate, ethoxifen , ethoxyphenethyl, ethoxysulfuron, etobenzanide, F-9600, F-5231, i. e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1yl]phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop- R, fenoxaprop-ethyl,

- 66 042989 fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrion, fentrazamide, flamprop, flamprop-Misopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-R, fluazifopbutyl, fluazifop-P-butyl, flucarba zones, flucarbazone-sodium , flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl -sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, flutiacet, flutiacet-methyl, fomesafen, fomesafen sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate- R -sodium, glyphosate, glyphosate-ammonium,

-isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, i. e. O-(2,4dimethyl-6-nitrophenyl)-O-ethylisopropylphosphoramidothioate, galauxifen, galauxifen-methyl, halofafen, halosulfuron, halosulfuron-methyl, haloxifop, haloxifop-R, haloxifop-ethoxyethyl, haloxifop-P-ethoxyethyl, haloxifop-methyl, haloxyfop-P-methyl, hexazinon, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl-(2,4-dichlorophenoxy)acetate, imazamethabenz, imazametabenz-methyl, imazamox, imazamox-ammonium, imazapik, imazapir-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr- immonium, imazosulfuron, indanophane, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynyl-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutol, carbutylate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MSRV, MSRV-methyl, -ethyl and -sodium, mecoprop, mecopropsodium and -butyl, mecoprop-R, mecoprop-R-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, metabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, metabenzthiazuron, methiopyrsulfuron, methiozol in , methylisothiocyanate, metobromuron, metolachlor, S-metolachlor, methosulam, methoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950 i.e. N-[3-chloro-4 -(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC310 i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid ( pelargonic acid), norflurazone, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxulam, pentachlorophenol, pentoxazone, petoxamide, petroleum oils, phencopper fam , picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuronmethyl, prodiamine, profoxydim, promethone, promethrin, propachlor, propanil, propaquizafop, propazine, profam, propisochlor, propoxycarbazone, propoxycarbazone sodium, propyrisulfuron, propizamide, prosulfocarb, prosulfuron, pyraclonil , pyraflufen, pyraflufenethyl, pyrasulfotol, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuronethyl, pyrazoxyfen, pyribambenz, pyribambenzisopropyl, pyribambenz-propyl, pyribenzoxime, pyributicarb, pyridafol, pyridate, pyrifthalide, pyriminobac, pyriminobacmethyl, pyrimisulfan, pyrithiobac, pyrithiobacsodium, pyroxasulfone, piroxulam, quinclorac, quinmerac, quinoclamin, quizalofop, quizalofopethyl, quizalofop-R, quizalofop-P-ethyl, quizalofop-R-tefuryl, rimsulfuron, saflufenacil, sethoxydim, sidurone, simazine, simetrin, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometu ronmethyl, sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chloro-4(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i. e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin- 4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumetone, terbutylazine, terbutrin, tenylchlor, thiazopyr, thiencarbazone, thiencarbazone- methyl, thifensulfuron, thifensulfuronmethyl, thiobencarb, thiafenacil, tolpyralate, topramesone, tralkoxydim, triafamon, triallate, triasulfuron, triaziflam, tribenuron, tribenuronmethyl, triclopyr, triethazine, trifloxysulfuron, trifloxysulfuron sodium, trifludimoxazine, trifluralin, tri flusulfuron, triflusulfuron methyl, tritosulfuron, urea sulfate, vernolate , XDE-848, ZJ-0862, i.e. 3,4dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline and the following compounds:

o ^CO ₂ Et

Examples of plant growth regulators as possible components for the formation of a mixture

- 67 042989 are acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancimidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminoside, dazomet, n-decanol, dikegulac, dikegulac sodium, endothal, endothal-dicalium, α-disodium and mono(H2dimethylalkylammonium), ethephon, flumetraline, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione calcium, prohydrojasmone, salicylic acid, strigolactone, teknazen, thidiazuron, triacontanol, trinexapac, trinexapak-ethyl , cytodef, uniconazole, uniconazole-P.

Also suitable as components for forming a combination with the compounds of formula (I) according to the present invention are, for example, the following safeners:

S1) compounds from the group of derivatives of heterocyclic carboxylic acids:

S1 ^a ) compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1 ^a ), preferably compounds such as

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

S1 ^b ) derivatives of dichlorophenylpyrazolecarboxylic acid (S1 ^b ), preferably compounds such as ethyl-1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl-1-(2,4- dichlorophenyl)-5isopropylpyrazole-3-carboxylate (S1-3), ethyl-1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4) and related compounds as described in EP-A-333131 and EP-A-269806;

S1 ^c ) 1,5-diphenylpyrazole-3-carboxylic acid derivatives (S1 ^c ), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl -1-(2-chlorophenyl)-5phenylpyrazole-3-carboxylate (S1-6) and related compounds as described, for example, in EP-A-268554;

S1 ^d ) compounds of the triazolecarboxylic acid type (S1 ^d ), preferably compounds such as fenchlorazole (ethyl ester), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4triazole-3-carboxylate (S1-7), and related compounds as described in EP-A-174562 and EP- A-346620;

S1 ^e ) compounds of the type 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl2-isoxazoline-3-carboxylic acid (S1 ^e ), preferably compounds such as ethyl-5-( 2,4dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S19) and related compounds as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10), or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) (isoxadifen-ethyl), or npropyl-5,5-diphenyl -2-isoxazoline-3-carboxylate (S1-12), or ethyl 5-(4-fluorophenyl)-5-phenyl-2isoxazoline-3-carboxylate (S1-13) as described in patent application WO-A- 95/07897;

S2) compounds from the group of 8-quinolinoxy derivatives (S2):

S2 ^a ) compounds of the 8-quinolineoxyacetic acid type (S2 ^a ), preferably 1-methylhexyl-(5chloro-8-quinolinoxy)acetate (cloquintoset-mexyl) (S2-1), 1,3-dimethylbut-1-yl-(5 -chloro-8-quinolinoxy)acetate (S2-2), 4-allyloxybutyl-(5-chloro-8-quinolineoxy)acetate (S2-3), 1-allyloxyprop-2yl-(5-chloro-8-quinolinoxy)acetate (S2 -4), ethyl (5-chloro-8-quinolinoxy) acetate (S2-5), methyl-(5-chloro-8-quinolinoxy) acetate (S2-6), allyl-(5-chloro-8-quinolinoxy) acetate ( S2-7), 2-(2-propylideneimineoxy)-1ethyl(5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxoprop-1-yl(5-chloro-8-quinolinoxy)acetate (S2- 9) and related compounds as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0492366 and (5-chloro-8-quinolinoxy)acetic acid (S2-10 ), hydrates and their salts, for example their salts formed with lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium, as described in WO-A-2002/34048;

S2 ^b ) compounds of the type (5-chloro-8-quinolinoxy)malonic acid (S2 ^b ), preferably compounds such as diethyl-(5-chloro-8-quinolinoxy)malonate, diallyl-(5-chloro-8-quinolinoxy) malonate, methylethyl-(5-chloro-8-quinolinoxy)malonate and related compounds as described in EP-A-0582198;

S3) active ingredients of the dichloroacetamide type (S3), which are often used as pre-emergence antidotes (soil-acting antidotes), e.g. dichlormide (N,N-diallyl-2,2-dichloroacetamide) (S3-1),

R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),

R-28725 (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4- benzoxazine) (S3-4),

PPG-1292 (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) from PPG Industries (S3-5),

DKA-24 (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from Sagro-Chem (S3-6),

AD-67 or MON 4660 (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) from Nitrokemia or Monsanto (S3-7),

TI-35 (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8),

- 68 042989

Diclonon (dicyclonon) or BAS145138 or LAB 145138 (S3-9), ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF, furilazole or MON 13900 ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10) and (R)-rooMep of each (S3-11);

S4) compounds from the class of acylsulfonamides (S4):

S4 ^a ) N-acylsulfonamides of formula (S4 ^a ) and their salts as described in WO-A-97/45016,

in which

RA ¹ is (C 1 -C ₆ )alkyl, (C ₃ -C ₆ ) cycloalkyl, where the last 2 radicals are substituted v _A with substituents from the halogen group, (C _g C 4 ) alkoxy, (C 1 -C ₆ ) haloalkoxy and (C 1 -C ₄ )alkylthio, and, in the case of cyclic radicals, also (C1-C ₄ )alkyl and (C1-C ₄ )haloalkyl;

RA ² is halogen, (C1-C ₄ )alkyl, (C1-C ₄ )alkoxy, CF ₃ ;

m _A is 1 or 2;

v _A is 0, 1, 2, or 3;

S4 ^b ) 4-(benzoylsulfamoyl)benzamide type compounds of formula (S4 ^b ) and their salts as described in WO-A-99/16744,

in which

R _B 1, R _B ² independently represent hydrogen, (C1-C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, (C ₃ -C ₆ )alkenyl, (C ₃ -C ₆ )alkynyl,

R _B ³ is halogen, (C1-C ₄ )alkyl, (C1-C ₄ )haloalkyl or (C1-C4)alkoxy and m _B is 1 or 2, for example, compounds in which

R _B 1 = cyclopropyl, R _B ² = hydrogen, and (R _B ³ ) = 2-OMe (cyprosulfamide, S4-1),

R _B 1 = cyclopropyl, R _B ² = hydrogen, and (R _B ³ ) = 5-Cl-2-OMe (S4-2),

R _B 1 = ethyl, R _B ² = hydrogen and (R _B ³ ) = 2-OMe (S4-3),

R _B 1 = isopropyl, R _B ² = hydrogen, and (R _B ³ ) = 5-Cl-2-OMe (S4-4), and

R _B 1 = isopropyl, R _B ² = hydrogen and (R _B ³ ) = 2-OMe (S4-5);

S4 ^c ) compounds from the class of benzoylsulfamoylphenylureas of formula (S4 ^c ) as described in EP-A365484,

in which

R _C 1 , R _C ² independently represent hydrogen, (C 1 -C ₈ )alkyl, (C ₃ -C ₈ )cycloalkyl, (C ₃ -C ₆ )alkenyl, (C ₃ -C ₆ )alkynyl,

_RC ³ is halogen, (C1-C ₄ )alkyl, (C1-C ₄ )alkoxy, CF ₃ and m _C is 1 or 2;

For example,

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

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

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

S4 ^d ) compounds of the N-phenylsulfonyl terephthalamide type of formula (S4 ^d ) and salts thereof, which are known, for example, from CN 101838227,

in which

RD ⁴ is halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )alkoxy, CF ₃ ;

m _D is 1 or 2;

RD ⁵ is hydrogen, (C1-C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, (C ₂ -C ₆ )alkenyl, (C ₂ -C ₆ ) alkynyl, (C 5 -C 6 )cycloalkenyl;

S5) active ingredients from the class of derivatives of hydroxyaromatic and aromatic aliphatic carboxylic acids (S5), e.g. acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid as described in

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WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001;

S6) active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g. 1-methyl-3-(2thienyl)-1,2-dihydroquinoxalin-2-one, )-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-( 2thienyl)-1,2-dihydroquinoxalin-2-one as described in WO-A-2005/112630;

S7) compounds from the class of diphenylmethoxyacetic acid derivatives (S7), for example methyldiphenylmethoxyacetate (CAS Registry 41858-19-9) (S7-1), ethyldiphenylmethoxyacetate or diphenylmethoxyacetic acid as described in WO-A-98/38856;

S8) compounds of formula (S8) as described in WO-A-98/27049,

in which symbols and indices are defined as follows:

RD ¹ is halo, (C1- _C4 ) alkyl, (C1- _C4 ) haloalkyl, (C1- _C4 ) alkoxy, (C1- _C4 ) haloalkoxy,

RD ² is hydrogen or (C1-C ₄ )alkyl,

RD ³ is hydrogen, (C1-C ₈ )alkyl, (C ₂ -C ₄ )alkenyl, (C ₂ -C ₄ ) alkynyl or aryl, where each of the above carbon-containing radicals is unsubstituted or substituted by one or more, preferably not more than three identical or different radicals from the group consisting of halogen and alkoxy; or their salts, nD is an integer from 0 to 2;

S9) active ingredients from the 3-(5-tetrazolylcarbonyl)-2-quinolones class (S9), e.g. 1,2dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS registration : 219479-18-2), 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;

S10) compounds of formula (S10 ^a ) or (S10 ^b ) as described in WO-A-2007/023719 and WO-A2007/023764,

(S10 ^a ) (S10 ^b ) where

RE ¹ is halogen, (C1-C ₄ )alkyl, methoxy, nitro, cyano, CF ₃ , OCF ₃ ,

YE, ZE are independently O or S, nE is an integer from 0 to 4,

RE ² is (C1-C ₁₆ )alkyl, (C ₂ -C ₆ )alkenyl, (C ₃ -C ₆ )cycloalkyl, aryl; benzyl, halobenzyl,

RE ³ is hydrogen or (C1-C ₆ )alkyl;

S11) active ingredients of the hydroxyimino compound type (S11) which are known as seed dressing agents, e.g. seed dressing for millet/sorghum against damage caused by metolachlor, fluxofenim (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)oxime) ( S112), which is known as a seed dressing antidote for millet/sorghum against metolachlor damage, and cyometrinil or CGA-43089 ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing antidote for millet/sorghum against damage caused by metolachlor;

S12) active ingredients from the class of isothiochromanones (S12), e.g. and related compounds from WO-A-1998/13361;

S13) one or more compounds from the group (S13):

naphthoic anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing antidote for corn against damage caused by the thiocarbamate herbicide, fenclorim (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as an antidote for pretilachlor in cultivated rice, flurazol (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing antidote for millet/sorghum from damage caused by alachlor and metolachlor,

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CL 304415 (CAS Registry Number 31541-57-8), (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as an antidote for maize from damage caused by imidazolinones,

MG 191 (CAS registration number 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a corn antidote,

MG 838 (CAS Registry Number 133993-74-5), (2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia, disulfotone (O,O-diethyl -S-2-ethylthioethylphosphorodithioate) (S13-7), dietholate (O,O-diethyl-O-phenylphosphorothioate) (S13-8), mephenate (4-chlorophenylmethylcarbamate) (S13-9);

S14) active ingredients which, in addition to herbicidal activity against harmful plants, also exhibit antidote activity against cultivated plants such as rice, for example dimepiperate or MY-93 (S-1-methyl-1-phenylethylpiperidine-1-carbothioate), which is known as an antidote for rice against damage caused by the herbicide molinate, daimuron or SK23 (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as an antidote for rice against damage caused by the herbicide imazosulfuron, cumiluron = JC-940 (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A60087254), which is known as an antidote for rice damage caused by certain herbicides, methoxyphenone or NK 049 (3,3'-dimethyl-4-methoxybenzophenone), which are known as an antidote for rice damage caused by certain herbicides,

CSB (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai (CAS Accession No. 5409106-4), which is known as an antidote for certain herbicide damage in rice;

S15) compounds of formula (S15) or their o tautomers

as described in WO-A-2008/131861 and WO-A-2008/131860, in which RH ¹ is a (C1C ₆ ) haloalkyl radical,

RH ² is hydrogen or halogen and

RH ³ , RH ⁴ independently represent hydrogen, (C1-C ₁₆ )alkyl, (C ₂ -C ₁₆ )alkenyl or (C ₂ -C ₁₆ )alkynyl, where each of the last 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halo, 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 heterocyclyl , which is unsubstituted or substituted, or (C ₃ -C ₆ ) cycloalkyl, (C 4 -C 6 ) cycloalkenyl, (C ₃ -C ₆ ) cycloalkyl fused on one side of the ring with a 4-6 membered saturated or unsaturated carbocyclic ring, or (C4-C6)cycloalkenyl fused on one side of the ring with a 4 to 6 membered saturated or unsaturated carbocyclic ring, where each of the last 4 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxyl, cyano, (C1-C ₄ )alkyl, (C1-C ₄ ) haloalkyl, (C1-C4) alkoxy, (C1-C ₄ ) haloalkoxy, (C1-C ₄ ) alkylthio, (C1-C ₄ ) alkylamino, di[( _C1C4 )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 a heterocyclyl which is unsubstituted or substituted, or

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

RH ⁴ is hydrogen or (C1-C ₄ )alkyl, or

R _H ³ and RH ⁴ together with the directly bonded nitrogen atom are a four to eight membered heterocyclic ring which, in addition to the nitrogen atom, may also contain additional ring heteroatoms, preferably no more than two additional ring heteroatoms from the group consisting of N, O and S, and which is unsubstituted or substituted by one or more radicals from the group consisting of halo, cyano, nitro, (C1-C4)alkyl, (C1- _C4 )haloalkyl, ( _CpC4 )alkoxy, (C1-C4)haloalkoxy, and (C1 -C ₄ )alkylthio;

S16) active ingredients which are used primarily as herbicides, but which also have an antidote effect on cultivated plants, e.g. (2,4dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R, S)-2-(4-chloro-o-

- 71 042989 tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-tolyloxy)acetic acid (MCPA), 4-(4-chloro- o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl-3,6dichloro-2-methoxybenzoate (lactidichloroethyl).

Preferred antidotes in combination with the compounds of formula (I) according to the present invention and/or their salts, especially with the compounds of formulas (I.1)-(I.50) and/or their salts, are cloquintoset-mexil, cyprosulfamide, fenchlorazole ethyl ester, isoxadifenethyl, mefenpyrdiethyl, fenclorim, cumiluron, S4-1 and S4-5, and particularly preferred safeners are cloquintosetmexil, cyprosulfamide, isoxadifenethyl and mefenpyrdiethyl.

Biological examples

A. Herbicidal activity and crop compatibility after emergence

Seeds of mono- and dicotyledonous weeds and crop plants were laid out in sandy loamy soil in plastic or wood fiber pots, covered with soil and grown under controlled growth conditions in a greenhouse. The test plants were treated at the single leaf stage 2-3 weeks after sowing. Compounds of the present invention formulated as wettable powders (WP) or emulsion concentrates (EC) were then sprayed onto green plant parts as an aqueous suspension or emulsion with 0.5% additive at an equivalent water application rate of 600 l/ha. After the test plants had stood for approximately 3 weeks in the greenhouse, under optimal growth conditions, the effect of the preparations was assessed visually by comparison with untreated controls. For example, 100% efficiency corresponded to the state when the plants died, 0% efficiency corresponded to control plants. Crop compatibility values were also evaluated accordingly.

In table. A1-A16 below shows the efficacy values of selected compounds of general formula (I) in accordance with Tables I.I.1-I.50 against various noxious plants and the application rate corresponding to 80 g/ha or less, which were obtained using the above test method.

Table A1

Compound Example No. Alopecurus myosuroides (Efficacy in %) Application rate [g/ha] 1.1-2 100 80 1.1-3 100 80 1.1-22 80 80 1.1-23 90 80 1.1-127 90 80 1.1-132 80 80 1.1-141 90 80 1.1-151 90 80 1.1-182 80 80 1.1-183 80 80 1.1-184 80 80 1.1-242 90 20 1.1-251 100 80 1.1-255 90 80 1.2-2 100 80 1.8-2 80 80 1.8-127 80 80 1.1-32 80 80 1.1-142 80 20 1.1-2-3 90 20 1.1-144 80 20 1.1-8 90 80 1.1-43 80 20 1.1-46 80 20 1.2-6 80 20 1.2-32 80 20 1.5-3 80 20 1.5-2 80 20 1.1-233 90 20 1.1-153 90 20 1.1-152 80 20

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Table A2

Compound Example No. Echinochloa crus-galli (Efficacy %) Application rate [g/ha] 1.1-1 100 80 1.1-2 100 80 1.1-3 100 80 1.1-5 100 80 1.1-22 100 80 1.1-23 100 80 1.1-42 100 20 1.1-72 100 80 1.1-127 100 80 1.1-132 100 80 1.1-141 100 80 1.1-151 100 80 1.1-182 100 80 1.1-183 100 80 1.1-184 100 80 1.1-241 100 80 1.1-242 100 80 1.1-251 100 80 1.1-254 100 80 1.1-255 100 80 1.2-2 100 80 1.8-2 100 80 1.8-23 100 80 1.8-42 100 80 1.8-127 100 20 1.46-2 100 80 1.1-32 100 80 1.1-142 100 20 1.1-102 100 20 1.1-2-3 100 20 1.1-144 100 20 1.1-8 100 80 1.11-3 100 20 1.1-43 100 20 1.8-43 90 20 1.1-51 100 20 1.8-46 90 20 1.1-46 100 20 1.8-51 90 20 1.47-3 80 20 1.2-6 100 20 1.2-8 100 20 1.2-32 100 20 1.2-43 100 20 1.2-145 100 20 1.5-3 100 20 1.5-2 100 20 1.12-3 100 20 1.1-293 90 20 1.1-233 100 20 1.1-231 100 20 1.1-153 100 20 1.1-152 100 20

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Table AZ

Compound Example No. Setaria viridis (Efficacy in %) Application rate [g/ha] 1.1-1 100 80 1.1-2 100 80 1.1-3 100 80 1.1-5 100 80 1.1-22 100 80 1.1-23 100 80 1.1-42 100 20 1.1-72 100 20 1.1-127 100 80 1.1-132 100 80 1.1-141 100 20 1.1-151 100 80 1.1-183 100 80 1.1-184 100 20 1.1-241 100 80 1.1-242 100 80 1.1-251 100 20 1.1-254 100 80 1.1-255 100 80 1.2-2 100 80 1.8-2 100 80 1.8-23 100 80 1.8-42 100 80 1.8-127 100 20 1.46-2 100 80 1.1-32 100 80 1.1-142 100 20 1.1-102 100 20 1.1-2-3 100 20 1.1-144 100 20 1.1-8 100 80 1.1-43 100 20 1.8-43 100 20 1.1-51 100 20 1.8-46 100 20 1.1-46 100 20 1.8-51 100 20 1.8-44 100 20 1.47-6 100 20 1.47-3 100 20 1.2-6 100 20 1.2-8 100 20 1.2-32 100 20 1.2-43 100 20 1.6-3 100 20 1.2-145 100 20 1.4-3 90 20 1.5-3 100 20 1.5-2 100 20 1.12-3 100 20 1.14-3 90 20 1.1-293 90 20 1.1-233 100 20 1.1-231 100 20 1.1-153 100 20 1.1-152 100 20

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Table A4

Compound Example No. Abutilon theophrasti (Efficacy in %) Application rate [g/ha] 1.1-1 100 80 1.1-2 100 80 1.1-3 100 80 1.1-5 100 80 1.1-22 100 80 1.1-23 100 80 1.1-42 100 20 1.1-72 100 20 1.1-127 100 80 1.1-132 100 80 1.1-141 100 80 1.1-151 100 80 1.1-182 100 80 1.1-183 100 80 1.1-184 100 80 1.1-241 100 80 1.1-242 100 80 1.1-251 100 80 1.1-254 100 80 1.1-255 100 80 1.2-2 100 80 1.8-2 100 80 1.8-23 100 80 1.8-42 100 80 1.8-127 100 20 1.46-2 100 80 1.1-32 100 80 1.1-142 100 20 1.1-102 100 20 1.1-2-3 100 20 1.1-144 100 20 1.1-6 100 20 1.1-8 100 80 1.11-3 100 20 1.1-43 100 20 1.8-43 100 20 1.1-51 100 20 1.8-46 100 20 1.1-46 100 20 1.8-51 100 20 1.8-44 100 20 1.47-6 100 20 1.47-3 100 20 1.2-6 100 20 1.2-8 100 20 1.2-32 100 20 1.2-43 100 20 1.6-3 100 20 1.6-43 100 20 1.2-145 100 20 1.4-3 100 20 1.4-43 100 20 1.5-3 100 20 1.5-2 100 20 1.12-3 100 20 1.14-3 100 20 1.1-293 100 20 1.1-233 100 20 1.1-231 100 20 1.1-153 100 20 1.1-152 100 20

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Table A5

Compound Example No. Amaranthus retroflexus (Efficiency in %) Application rate [g/ha] 1.1-1 100 20 1.1-2 100 80 1.1-3 100 80 1.1-5 100 80 1.1-22 100 80 1.1-23 100 80 1.1-42 100 20 1.1-72 100 20 1.1-127 100 20 1.1-132 100 80 1.1-141 100 80 1.1-151 100 80 1.1-182 100 80 1.1-183 100 80 1.1-184 100 80 1.1-241 100 80 1.1-242 100 80 1.1-251 100 80 1.1-254 100 80 1.1-255 100 80 1.2-2 100 80 1.8-2 100 20 1.8-23 100 80 1.8-42 100 20 1.8-127 100 20 1.46-2 100 80 1.1-32 100 80 1.1-142 100 20 1.1-102 100 20 1.1-2-3 100 20 1.1-144 100 20 1.1-6 100 20 1.1-8 100 80 1.1-43 100 20 1.8-43 100 20 1.1-51 100 20 1.8-46 100 20 1.1-46 100 20 1.8-51 100 20 1.8-44 100 20 1.47-6 100 20 1.47-3 100 20 1.2-6 100 20 1.2-8 100 20 1.2-32 100 20 1.2-43 100 20 1.6-3 100 20 1.2-145 100 20 1.4-3 100 20 1.4-43 100 20 1.5-3 100 20 1.5-2 100 20 1.12-3 100 20 1.14-3 100 20 1.1-293 100 20 1.1-233 100 20 1.1-231 100 20 1.1-153 100 20 1.1-152 100 20

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Table A6

Compound Example No. Matricaria inodora (Efficacy in %) Application rate [g/ha] 1.1-1 100 80 1.1-2 100 80 1.1-3 100 80 1.1-5 100 80 1.1-22 100 80 1.1-23 100 80 1.1-42 100 20 1.1-72 100 80 1.1-127 100 80 1.1-132 90 80 1.1-141 100 80 1.1-151 100 80 1.1-182 100 80 1.1-183 100 80 1.1-184 100 80 1.1-241 100 80 1.1-242 100 80 1.1-251 100 80 1.1-254 100 80 1.1-255 100 80 1.2-2 100 80 1.8-2 100 20 1.8-23 100 20 1.8-42 100 20 1.8-127 100 20 1.46-2 100 20 1.1-32 100 80 1.1-142 100 20 1.1-102 100 20 1.1-2-3 100 20 1.1-144 100 20 1.1-8 100 80 1.11-3 90 20 1.1-43 100 20 1.8-43 100 20 1.1-51 100 20 1.8-46 100 20 1.1-46 100 20 1.8-51 100 20 1.8-44 100 20 1.47-3 100 20 1.2-6 100 20 1.2-8 100 20 1.2-32 100 20 1.2-43 100 20 1.6-3 100 20 1.2-145 100 20 1.4-3 80 20 1.4-43 90 20 1.5-3 100 20 1.5-2 100 20 1.1-293 100 20 1.1-233 100 20 1.1-231 100 20 1.1-153 100 20 1.1-152 100 20

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Table A7

Compound Example No. Polygonum convolvulus (Efficacy in %) Application rate [g/ha] 1.1-1 100 80 1.1-2 100 20 1.1-3 100 80 1.1-5 100 80 1.1-22 100 80 1.1-23 100 80 1.1-42 100 20 1.1-72 100 80 1.1-127 100 80 1.1-132 100 80 1.1-141 100 80 1.1-151 100 80 1.1-182 100 80 1.1-183 100 80 1.1-184 100 80 1.1-241 100 80 1.1-242 100 80 1.1-251 100 80 1.1-254 100 80 1.1-255 100 80 1.2-2 100 80 1.8-2 100 20 1.8-23 100 20 1.8-42 100 80 1.8-127 100 80 1.46-2 100 20 1.1-32 100 80 1.1-142 100 20 1.1-102 100 20 1.1-2-3 100 20 1.1-144 100 20 1.1-8 100 80 1.1-43 100 20 1.8-43 100 20 1.1-51 100 20 1.8-46 100 20 1.1-46 100 20 1.8-51 100 20 1.8-44 100 5 1.47-6 100 20 1.47-3 100 20 1.2-6 100 20 1.2-8 100 20 1.2-32 100 20 1.2-43 100 20 1.2-145 100 20 1.4-43 100 20 1.5-3 100 20 1.5-2 100 20 1.12-3 100 20 1.14-3 100 20 1.1-233 100 20 1.1-231 100 20 1.1-153 100 20 1.1-152 100 20

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Table A8

Compound Example No. Stellaria media (Efficiency in %) Application rate [g/ha] 1.1-1 100 80 1.1-2 100 20 1.1-3 100 80 1.1-5 100 80 1.1-22 100 80 1.1-23 100 80 1.1-42 100 20 1.1-72 100 80 1.1-127 100 20 1.1-132 100 80 1.1-141 100 80 1.1-151 90 80 1.1-182 100 80 1.1-183 100 20 1.1-184 100 80 1.1-241 100 80 1.1-242 100 80 1.1-251 100 80 1.1-254 90 80 1.1-255 100 80 1.2-2 100 80 1.8-2 100 20 1.8-23 100 80 1.8-42 100 80 1.8-127 100 20 1.46-2 80 80 1.1-32 100 80 1.1-142 100 20 1.1-102 80 20 1.1-2-3 100 20 1.1-144 80 20 1.1-8 100 80 1.11-3 100 20 1.1-43 80 20 1.8-43 80 20 1.1-51 100 20 1.8-46 100 20 1.1-46 100 20 1.8-44 100 20 1.47-6 80 20 1.2-6 100 20 1.2-8 100 20 1.2-43 100 20 1.6-3 100 20 1.6-43 90 20 1.2-145 100 20 1.4-43 80 20 1.5-3 100 20 1.5-2 100 20 1.12-3 100 20 1.1-293 100 20 1.1-233 100 20 1.1-231 100 20 1.1-153 100 20 1.1-152 100 20

Table A9

Compound Example No. Viola tricolor (Efficiency in %) Application rate [g/ha] 1.1-1 100 80 1.1-2 100 80

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1.1-3 100 80 1.1-5 100 20 1.1-22 100 80 1.1-23 100 20 1.1-42 100 20 1.1-72 100 80 1.1-127 100 80 1.1-151 100 80 1.1-182 100 20 1.1-183 100 20 1.1-184 100 80 1.1-241 100 80 1.1-242 100 80 1.1-251 100 80 1.1-254 100 80 1.1-255 100 80 1.2-2 100 80 1.8-2 100 80 1.8-23 100 20 1.8-42 100 80 1.8-127 100 80 1.46-2 80 80 1.1-32 100 80 1.1-142 100 20 1.1-102 100 20 1.1-2-3 100 20 1.1-144 100 20 1.1-6 100 20 1.1-8 100 80 1.11-3 90 20 1.1-43 100 20 1.8-43 100 20 1.1-51 100 20 1.8-46 100 20 1.1-46 100 20 1.8-51 100 20 1.8-44 100 20 1.47-6 100 20 1.47-3 100 20 1.2-6 100 20 1.2-8 100 20 1.2-32 100 20 1.2-43 100 20 1.6-3 100 20 1.6-43 100 20 1.2-145 100 20 1.4-3 100 20 1.4-43 100 20 1.5-3 100 20 1.5-2 100 20 1.12-3 100 20 1.14-3 100 20 1.1-293 100 20 1.1-233 100 20 1.1-231 100 20 1.1-153 100 20 1.1-152 100 20

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Table A10

Compound Example No. Veronica persica (Efficiency in %) Application rate [g/ha] 1.1-1 100 80 1.1-2 100 20 1.1-3 100 80 1.1-5 100 80 1.1-22 100 80 1.1-23 100 80 1.1-42 100 80 1.1-72 100 80 1.1-127 100 20 1.1-132 100 80 1.1-141 100 80 1.1-151 100 80 1.1-182 100 80 1.1-183 100 20 1.1-184 100 80 1.1-241 100 80 1.1-242 100 80 1.1-251 100 80 1.1-254 90 80 1.1-255 100 80 1.2-2 100 20 1.8-2 100 80 1.8-23 100 80 1.8-42 100 80 1.8-127 100 20 1.46-2 80 80 1.1-32 100 80 1.1-142 100 20 1.1-102 100 20 1.1-2-3 100 20 1.1-144 100 20 1.1-6 100 20 1.1-8 100 80 1.1-43 100 20 1.8-43 100 20 1.1-51 100 20 1.8-46 100 20 1.1-46 100 20 1.8-51 100 20 1.8-44 100 20 1.47-6 100 20 1.47-3 100 20 1.2-6 100 20 1.2-8 100 20 1.2-32 100 20 1.2-43 100 20 1.6-3 100 20 1.6-43 100 5 1.2-145 100 20 1.4-3 80 20 1.4-43 100 20 1.5-3 100 20 1.5-2 100 20 1.12-3 100 20 1.14-3 100 20 1.1-293 100 20 1.1-233 100 20 1.1-231 100 20 1.1-153 100 20 1.1-152 100 20

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Table All

Compound Example No. Pharbitis purpurea (Efficacy in %) Application rate [g/ha] 1.1-1 100 80 1.1-2 100 20 1.1-3 100 80 1.1-5 100 80 1.1-22 100 80 1.1-23 100 80 1.1-42 100 20 1.1-72 100 20 1.1-127 100 20 1.1-132 100 80 1.1-141 100 80 1.1-151 100 80 1.1-182 100 80 1.1-183 100 80 1.1-184 100 80 1.1-241 100 80 1.1-242 100 80 1.1-251 100 80 1.1-254 100 80 1.1-255 100 80 1.2-2 100 20 1.8-2 100 80 1.8-23 100 20 1.8-42 100 80 1.8-127 100 20 1.46-2 100 80 1.1-32 100 80 1.1-142 100 20 1.1-102 100 20 1.1-2-3 100 20 1.1-144 100 20 1.1-8 100 80 1.1-43 100 20 1.8-43 100 20 1.1-51 100 20 1.8-46 100 20 1.1-46 100 20 1.8-51 100 20 1.8-44 100 20 1.47-6 100 20 1.47-3 100 20 1.2-6 100 20 1.2-8 100 20 1.2-32 100 20 1.2-43 100 20 1.5-3 100 20 1.5-2 100 20 1.12-3 100 5 1.14-3 100 20 1.1-233 100 20 1.1-231 100 20 1.1-153 100 20 1.1-152 100 20

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Table Al2

Compound Example No. Hordeum murinum (Efficacy in %) Application rate [g/ha] 1.1-2 100 20 1.1-5 80 80 1.1-127 90 80 1.1-184 80 80 1.1-242 90 80 1.1-254 100 80 1.1-254 80 80 1.8-2 80 20 1.2-2 80 80 1.8-42 80 80 1.1-102 100 20 1.1-144 80 20 1.1-8 90 80 1.1-46 100 20

Table A13

Compound Example No. Avena fatua (Efficiency in %) Application rate [g/ha] 1.1-2 80 80 1.1-3 80 80 1.1-127 80 80 1.1-182 90 80 1.1-242 80 80 1.1-251 80 80 1.1-254 80 80 1.1-255 80 80 1.2-2 80 80 1.8-127 80 80 1.1-32 80 80 12-3 100 20 1.1-144 100 20 1.1-8 80 80

Al4 table

Compound Example No. Lolium multiflorum (Efficacy in %) Application rate [g/ha] 1.1-3 100 80

Al5 table

Compound Example No. Lolium rigidum (Efficacy in %) Application rate [g/ha] 1.1-1 80 80 1.1-2 90 80 1.1-5 80 80 1.1-22 90 80 1.1-23 90 80 1.1-42 90 80 1.1-127 100 80 1.1-182 100 80 1.1-183 100 80 1.1-184 100 80 1.1-241 90 80 1.1-242 100 80 1.1-251 100 80 1.1-255 100 80 1.2-2 80 80 1.8-2 90 80 1.8-127 90 80 1.1-32 100 80

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1.1-102 80 20 1.1-144 100 20 1.1-8 90 80 1.1-46 80 20 1.2-32 80 20 1.1-233 90 20 1.1-153 80 20 1.1-152 80 20

Table A16

Compound Example No. Digitaria sanguinalis (Efficacy in %) Application rate [g/ha] 1.1-32 100 80 1.1-142 100 20 1.1-102 100 20 1.1-2-3 100 20 1.1-144 80 20 1.1-8 100 80 1.1-43 100 20 1.1-51 90 20 1.1-46 100 20 1.8-51 100 20 1.47-6 80 20 1.47-3 100 20 1.2-6 80 20 1.2-8 100 20 1.2-32 100 20 1.2-43 100 20 1.6-3 100 20 1.2-145 100 20 1.5-3 80 20 1.5-2 80 20 1.12-3 100 20 1.1-293 100 20 1.1-233 100 20 1.1-231 100 20 1.1-153 100 20 1.1-152 100 20

In table. A17-A21 below shows the compatibility values of selected compounds of General formula (I) in accordance with the table. I.1-I.50 with crops at an application rate corresponding to 80 g/ha or below, which were observed in tests in accordance with the above test method. The following are the observed effects on selected crops compared to untreated controls (values in %).

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Table A17

Compound Example No. Oryza sativa (Efficacy in %) Application rate [g/ha] 1.1-32 20 20 1.1-102 0 5 1.1-2-3 0 20 1.1-144 20 5 1.1-6 0 20 1.1-8 20 5 1.11-3 10 20 1.8-51 0 20 1.47-6 20 20 1.47-3 20 20 1.2-6 10 20 1.2-8 0 20 1.2-32 0 20 1.2-43 20 20 1.6-3 20 20 1.6-43 0 20 1.2-145 0 20 1.4-43 10 20 1.12-3 0 20 1.14-3 0 20 1.1-233 20 20 1.1-231 10 5 1.1-153 10 5 1.1-152 10 5 1.1-3 20 20 1.1-72 10 20 1.8-42 0 20 1.1-42 10 20 1.1-22 0 5 1.2-2 20 5 1.46-2 20 80 1.8-23 20 5 1.1-241 10 5 1.1-242 20 5 1.1-183 20 20 1.1-254 0 80 1.1-255 0 80 1.1-251 20 20 1.1-182 20 20 1.1-145 20 5 1.1-151 10 20 1.1-141 0 20 1.1-132 20 80

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Table A18

Compound Example No. Zea mays (Efficiency in %) Application rate [g/ha] 1.1-32 20 20 1.1-102 0 5 1.1-2-3 0 20 1.1-144 10 5 1.1-6 10 20 1.47-6 20 20 1.2-6 0 5 1.2-8 0 20 1.2-32 20 5 1.2-43 20 20 1.1-231 20 5 1.1-127 20 5 1.46-2 20 20 1.1-1 10 5 1.1-242 20 80 1.1-183 10 20 1.1-254 0 80 1.1-184 20 20 1.1-255 10 80 1.1-251 10 20 1.1-182 20 20 1.1-151 20 5 1.1-141 10 5 1.1-132 20 20

Table A19

Compound Example No. Brassica napis (Efficiency in %) Application rate [g/ha] 1.1-6 0 5 1.1-3 0 20 1.46-2 20 5 1.1-254 20 20 1.1-255 10 20 Table A20 Compound Glycinemax Application rate [g/ha] Example No. (Efficiency in %) 1.47-6 20 5 1.2-6 20 5 1.2-43 20 5 1.14-3 20 20 1.1-152 20 5 1.46-2 20 5 1.1-241 10 5 1.1-254 20 20 1.1-255 20 20

Table A21

Compound Example No. Triticum aestivum (Efficacy in %) Application rate [g/ha] 1.1-32 20 5 1.1-142 20 20 1.1-6 0 20 1.1-8 20 20 1.11-3 10 5 1.1-43 10 5 1.8-43 10 5 1.1-51 0 5 1.8-46 20 5 1.1-46 20 20 1.8-51 20 20 1.8-44 20 5

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1.47-6 20 5 1.47-3 20 20 1.2-6 20 20 1.2-8 0 20 1.2-32 20 5 1.2-43 10 20 1.2-145 20 20 1.4-43 10 20 1.5-3 20 5 1.5-2 20 5 1.12-3 20 20 1.14-3 20 20 1.1-231 20 5 1.1-152 20 5 1.1-3 10 20 1.1-72 20 20 1.8-42 20 5 1.1-42 20 20 1.1-22 20 20 1.2-2 20 5 1.46-2 20 20 1.1-5 20 80 1.1-23 20 20 1.8-23 20 20 1.1-241 10 5 1.1-1 20 80 1.1-242 20 5 1.1-254 10 20 1.1-255 10 20 1.1-251 10 20 1.1-182 10 5 1.1-151 20 80 1.1-141 20 20 1.1-132 10 20

The results show that the compounds of general formula (I) according to the present invention, when treated after emergence, exhibit adequate herbicidal efficacy against harmful plants such as, for example, Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Echinochloa crus- galli, Hordeum murinum, Lolium multiflorum, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronicapersica and Viola tricolor, at an application rate of 0.08 kg of active substance or less per hectare.

The tested crop plants Brassica napus, Glycine max, Oryza sativa, Triticum aestivum and Zea mays are affected only slightly, if at all, after application of the compounds of general formula (I) in accordance with the present invention at an application rate of 0.005 to 0.08 kg active substance per hectare.

B. Herbicidal activity and crop compatibility before emergence

Seeds of mono- and dicotyledonous weeds and crop plants were laid out in plastic or organic plant growing pots and covered with soil. The compounds of the present invention, formulated as wettable powders (WP) or emulsion concentrates (EC), were then applied to the surface of the covering soil as an aqueous suspension or emulsion with the addition of 0.5% additive at an equivalent water application rate of 600 l/ha. After treatment, the pots were placed in a greenhouse and maintained under the proper conditions for the growth of the test plants. After approximately 3 weeks, the efficacy of the formulations was assessed visually as a percentage by comparison with untreated controls. For example, 100% efficiency corresponded to the state when the plants died, 0% efficiency corresponded to control plants. Crop compatibility values were also evaluated accordingly.

In table. B1-B17 below shows the effectiveness of the selected compounds of General formula (I) in accordance with the table. I.1-I.50 against various noxious plants and the application rate corresponding to 320 g/ha or below, which was obtained using the above test method.

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Table B1

Compound Example No. Alopecurus myosuroides (Efficacy in %) Application rate [g/ha] 1.1-1 100 320 1.1-2 90 320 1.1-3 90 80 1.1-5 100 320 1.1-22 80 320 1.1-23 100 320 1.1-42 90 320 1.1-127 90 320 1.1-132 100 320 1.1-141 80 320 1.1-182 80 320 1.1-183 90 320 1.1-184 90 320 1.1-241 100 320 1.1-242 90 320 1.1-251 100 320 1.1-254 100 320 1.1-255 90 320 1.2-2 100 320 1.8-2 80 320 1.46-2 90 320 1.1-32 90 320 1.1-8 80 320 Compound Example No. 1.1-1 1.1-2 1.1-3 1.1-5 1.1-22 1.1-23 1.1-42 1.1-72 1.1-127 1.1-132 1.1-141 1.1-151 1.1-182 1.1-183 1.1-184 1.1-241 1.1-242 1.1-251 1.1-254 1.1-255 1.2-2 Table Echinochloa cras-galli (Efficacy in %) 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 AT 2 Application rate [g/ha] 320 320 320 320 320 320 320 320 320 320 320 320 320 320 320 320 320 320 320 320 320 1.8-2 100 320 1.8-23 100 320 1.8-42 100 320 1.8-127 100 320 1.46-2 100 320 1.1-32 100 320 1.1-142 90 80 1.1-8 100 320

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Table B3

Compound Example No. Setaria viridis (Efficacy in %) Application rate [g/ha] 1.1-1 100 320 1.1-2 100 80 1.1-3 100 320 1.1-5 100 320 1.1-22 100 80 1.1-23 100 80 1.1-42 100 80 1.1-72 100 80 1.1-127 100 320 1.1-132 100 320 1.1-141 100 320 1.1-151 100 320 1.1-182 100 320 1.1-183 100 320 1.1-184 100 80 1.1-241 100 320 1.1-242 100 80 1.1-251 100 320 1.1-254 100 320 1.1-255 100 320 1.2-2 100 320 1.8-2 100 320 1.8-23 100 320 1.8-42 100 320 1.8-127 100 320 1.46-2 100 320 1.1-32 100 320 1.1-142 100 80 1.1-8 100 320

Table B4

Compound Example No. Ab util on theophrasti (Efficacy in %) Application rate [g/ha] 1.1-1 100 320 1.1-2 100 80 1.1-3 100 320 1.1-5 100 320 1.1-22 100 80 1.1-23 100 80 1.1-42 100 80 1.1-72 100 80 1.1-127 100 320 1.1-132 100 320 1.1-141 100 320 1.1-151 100 320 1.1-182 100 320 1.1-183 100 320 1.1-184 100 80 1.1-241 100 320 1.1-242 100 80 1.1-251 100 320 1.1-254 100 320 1.1-255 100 320 1.2-2 100 320 1.8-2 100 320 1.8-23 100 320 1.8-42 100 320 1.8-127 100 320 1.46-2 100 320 1.1-32 100 320 1.1-142 100 80 1.1-8 100 320

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Table B5

Compound Example No. Amaranthus retroflexus (Efficiency in %) Application rate [g/ha] 1.1-1 100 20 1.1-2 100 80 1.1-3 100 80 1.1-5 100 80 1.1-22 100 80 1.1-23 100 80 1.1-42 100 20 1.1-72 100 20 1.1-127 100 20 1.1-132 100 80 1.1-141 100 80 1.1-151 100 80 1.1-182 100 80 1.1-183 100 80 1.1-184 100 80 1.1-241 100 80 1.1-242 100 80 1.1-251 100 80 1.1-254 100 80 1.1-255 100 80 1.2-2 100 80 1.8-2 100 20 1.8-23 100 80 1.8-42 100 20 1.8-127 100 20 1.46-2 100 80 1.1-32 100 320 1.1-142 100 80 1.1-8 100 320

Table B6

Compound Example No. Matricaria inodora (Efficacy in %) Application rate [g/ha] 1.1-1 100 320 1.1-2 100 80 1.1-3 100 320 1.1-5 100 80 1.1-22 100 80 1.1-23 100 800 1.1-42 100 80 1.1-72 100 80 1.1-127 100 320 1.1-132 100 320 1.1-141 100 320 1.1-151 100 320 1.1-182 100 320 1.1-183 100 320 1.1-184 100 80 1.1-241 100 320 1.1-242 100 80 1.1-251 100 320 1.1-254 100 320 1.1-255 100 320 1.2-2 100 320 1.8-2 100 320 1.8-23 100 80 1.8-42 100 320 1.8-127 100 320 1.46-2 100 320 1.1-32 100 320 1.1-142 100 80 1.1-8 100 320

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Table B7

Compound Example No. Polygonum convolvulus (Efficacy in %) Application rate [g/ha] 1.1-1 100 320 1.1-2 100 80 1.1-3 100 320 1.1-5 100 320 1.1-22 100 80 1.1-23 100 80 1.1-42 100 80 1.1-72 100 80 1.1-127 100 320 1.1-132 100 320 1.1-141 100 320 1.1-151 100 320 1.1-182 100 320 1.1-183 100 320 1.1-184 100 80 1.1-241 100 320 1.1-242 100 80 1.1-251 100 320 1.1-254 100 320 1.1-255 100 320 1.2-2 100 320 1.8-2 100 320 1.8-23 100 320 1.8-42 100 320 1.8-127 100 320 1.46-2 100 320 1.1-32 100 320 1.1-142 100 80 1.1-8 100 320 Table B8 Compound Stellaria media Application rate [g/ha] Example No. (Efficiency in %) 1.1-1 100 320 1.1-2 100 80 1.1-3 100 320 1.1-5 100 80 1.1-22 100 80 1.1-23 100 80 1.1-42 100 80 1.1-72 100 80 1.1-127 100 320 1.1-132 100 320 1.1-141 100 320 1.1-151 100 320 1.1-182 100 320 1.1-183 100 320 1.1-184 100 80 1.1-241 100 320 1.1-242 100 80 1.1-254 100 320 1.1-255 100 320 1.2-2 100 320 1.8-2 100 320 1.8-23 100 80 1.8-42 100 320 1.8-127 100 320 1.46-2 100 320 1.1-32 100 320 1.1-142 100 80 1.1-8 100 320

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Table B9

Compound Example No. Viola tricolor (Efficiency in %) Application rate [g/ha] 1.1-1 100 320 1.1-2 100 80 1.1-3 100 320 1.1-5 100 320 1.1-22 100 80 1.1-23 100 80 1.1-42 100 80 1.1-72 100 80 1.1-127 100 320 1.1-132 100 320 1.1-141 100 320 1.1-151 100 320 1.1-182 100 320 1.1-183 100 320 1.1-184 100 80 1.1-241 100 320 1.1-242 100 80 1.1-251 100 320 1.1-254 100 320 1.1-255 100 320 1.2-2 100 320 1.8-2 100 320 1.8-23 100 320 1.8-42 100 320 1.1-32 100 320 1.1-142 100 80 1.1-8 100 320

Table B10

Compound Example No. Veronica persica (Efficiency in %) Application rate [g/ha] 1.1-1 100 320 1.1-2 100 80 1.1-3 100 320 1.1-5 100 320 1.1-22 100 320 1.1-23 100 80 1.1-42 100 80 1.1-72 100 80 1.1-127 100 320 1.1-132 100 320 1.1-141 100 320 1.1-151 100 320 1.1-182 100 320 1.1-183 100 320 1.1-184 100 80 1.1-241 100 320 1.1-242 100 80 1.1-251 100 320 1.1-254 100 320 1.1-255 100 320 1.2-2 100 80 1.8-2 100 80 1.8-23 100 320 1.8-42 100 320 1.8-127 100 320 1.46-2 100 320 1.1-32 100 320 1.1-142 100 80 1.1-8 100 320

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Table Bl 1

Compound Example No. Pharbitis purpurea (Efficacy in %) Application rate [g/ha] 1.1-1 100 320 1.1-2 100 80 1.1-3 100 320 1.1-5 100 320 1.1-22 100 320 1.1-23 100 80 1.1-42 100 80 1.1-72 100 320 1.1-127 100 320 1.1-132 100 320 1.1-141 100 320 1.1-151 100 320 1.1-182 100 320 1.1-183 100 320 1.1-184 100 80 1.1-241 100 320 1.1-242 100 80 1.1-251 100 320 1.1-254 100 320 1.1-255 100 320 1.2-2 100 320 1.8-2 100 320 1.8-23 100 320 1.8-42 100 320 1.8-127 100 320 1.46-2 100 320 1.1-32 100 320 1.1-142 90 80 1.1-8 100 320

Table B12

Compound Example No. Hordeum murinum (Efficacy in %) Application rate [g/ha] 1.1-1 90 320 1.1-2 90 320 1.1-5 100 320 1.1-22 100 320 1.1-23 100 320 1.1-42 100 320 1.1-72 80 320 1.1-127 100 320 1.1-132 80 320 1.1-141 100 320 1.1-151 80 320 1.1-182 90 320 1.1-183 90 320 1.1-184 90 320 1.1-241 100 320 1.1-242 90 320 1.1-251 90 320 1.1-254 90 320 1.1-255 100 320 1.2-2 100 320 1.8-2 80 320 1.8-23 80 320 1.8-42 80 320 1.8-127 90 320 1.1-32 90 320

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Table B13

Compound Example No. Avena fatua (Efficiency in %) Application rate [g/ha] 1.1-2 90 320 1.1-5 100 320 1.1-23 100 320 1.1-42 90 320 1.1-72 90 320 1.1-127 90 320 1.1-132 90 320 1.1-141 80 320 1.1-151 90 320 1.1-182 90 320 1.1-183 90 320 1.1-184 90 320 1.1-241 100 320 1.1-242 80 320 1.1-251 90 320 1.1-254 90 320 1.1-255 90 320 1.8-2 80 320 1.8-42 80 320

Table B14

Compound Example No. Lolium multiflorum (Efficacy in %) Application rate [g/ha] 1.1-3 100 80

Table B15

Compound Example No. Lolium rigidum (Efficacy in %) Application rate [g/ha] 1.1-1 100 320 1.1-2 100 320 1.1-5 100 320 1.1-22 100 320 1.1-23 100 80 1.1-42 100 320 1.1-72 90 320 1.1-127 100 320 1.1-132 100 320 1.1-141 100 320 1.1-151 90 320 1.1-182 100 320 1.1-183 90 320 1.1-184 100 320 1.1-241 100 320 1.1-242 100 320 1.1-254 100 320 1.1-255 100 320 1.2-2 100 320 1.8-2 90 80 1.8-23 90 320 1.8-42 80 320 1.8-127 90 320 1.46-2 100 320 1.1-32 90 320 1.1-8 90 320

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Table B16

Compound Example No. Cyperus esculentus (Efficacy in %) Application rate [g/ha] 1.1-3 100 320 1.1-5 80 320 1.1-22 90 320 1.1-42 100 320 1.1-72 100 320 1.1-182 80 320 1.1-183 80 320 1.1-241 100 320 1.1-242 80 80 1.1-251 80 320 1.1-254 80 320 1.2-2 90 320 1.8-2 90 320 1.8-23 90 320 1.8-42 100 320 1.8-127 90 320

Table B17

Compound Example No. Digitaria sanguinalis (Efficacy in %) Application rate [g/ha] 1.1-32 100 320 1.1-142 100 80 1.1- 100 320

As the results show, the compounds of general formula (I) according to the present invention, when treated before emergence, show proper herbicidal efficacy against harmful plants, for example against such harmful plants as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Cyperus esculentus, Echinochloa crus-galli, Hordeum murinum, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica and Viola tricolor, at an application rate of 0.32 kg of active substance or less per hectare.

Claims (8)

1. Substituted thiophenyluracil of general formula (I) or its salt in which R ¹ is (C ₁ -C ₈ )alkyl R ² is hydrogen, (C1-C ₈ )alkyl, R ³ is halogen, R ⁴ is halogen, R ⁵ and R ⁶ are independently hydrogen, halogen, (C1-C8)alkyl, (C3-C8)cycloalkyl, (C3C8)cycloalkyl-(C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8) alkynyl, (C1-C10) haloalkyl, (C2-C8) haloalkenyl, (C2-C8) haloalkynyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4C10) halocycloalkenyl, (C1-C8) alkoxy, ( C1-C8) alkoxy-(C1-C8) alkyl, (C1-C8) alkoxy-(C1-C8) haloalkyl, (C1-C8) haloalkoxy-(C1-C8) haloalkyl, (C1-C8) haloalkoxy-(C1-C8) )alkyl, aryl, aryl-(C1-C8)alkyl, heteroaryl, heteroaryl-(C1-C8)alkyl, (C4-C10)cycloalkenyl-(C1-C8)alkyl, heterocyclyl, heterocyclyl-(C1-C8)alkyl, (C1-C8) alkylthio-(C1-C8) alkyl, (C1-C8) haloalkylthio-(C1-C8) alkyl, (C1-C8) alkylcarbonyl-(C1-C8) alkyl, C(O)OR ¹⁷ , C (O)NR ¹⁵ R ¹⁶ , C(O)R ¹⁷ , R ¹⁷ O(O)C-(C1-C ₈ )alkyl, R ¹⁵ R ¹⁶ N(O)C-(C1-C8)alkyl, R ¹⁵ R ¹⁶ N-(C1-C8)alkyl, or R ⁵ and R ⁶ together with the carbon atom to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring, m is 0, p is 0, 1, 2, 3, 4, 5, X is O (oxygen) or NR ¹¹ or NOR ¹² moieties, and R ¹¹ and R ¹² in NR ¹¹ and NOR ¹² moieties are independently defined as defined below, R ⁷ , R ⁸ , R ⁹ and R ¹⁰ independently represent hydrogen, fluorine, (C1-C ₈ )alkyl, (C ₃ -C ₈ )cycloalkyl, (C ₃ -C ₈ )cycloalkyl-(C1-C ₈ ) alkyl, (C ₂ -C ₈ )alkenyl, (C ₂ -C ₈ )alkynyl, (C1-C ₁₀ )-haloalkyl, (C ₂ -C ₈ ) haloalkenyl, (C ₂ -C ₈ ) haloalkynyl, (C ₃ -C ₁₀ ) halocycloalkyl, (C ₄ -C ₁₀ ) cycloalkenyl, (C ₄ -C ₁₀ ) halocycloalkenyl, (C 1-C ₈ ) alkoxy-(C 1 -C ₈ ) haloalkyl, (C ₁ -C ₈ )- haloalkoxy-(C ₁ -C ₈ )haloalkyl, aryl, aryl-(C1-C ₈ )alkyl, heteroaryl, heteroaryl-(C1-C ₈ )alkyl, (C ₄ -C ₁₀ )cycloalkenyl-(C1-C ₈ ) alkyl, heterocyclyl, heterocyclyl-(C1-C ₈ )alkyl, R ¹⁷ O-(C1-C8) alkyl, R ¹⁸ S-(C1-C ₈ )alkyl, (C1-C ₈ )alkylcarbonyl-( C1C ₈ )alkyl, C(O)OR ¹⁷ , C(O)NR ¹⁵ R ¹⁶ , C(O)R ¹⁷ , R ¹⁷ O(O)C-(C1-C8) alkyl, R ¹⁵ R ¹⁶ N(O )C-(C1-C8)alkyl, R ¹⁵ R ¹⁶ N(C ₁ -C ₈ )alkyl, or R ⁵ and R ⁷ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 8-membered monocyclic or bicyclic ring, or R ⁷ and R ⁸ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form an exomethylene group, or R ⁷ and R ⁹ together with the carbon atoms to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring, R ¹¹ is hydrogen, (C1-C ₈ )alkyl, (C ₃ -C ₈ )cycloalkyl, cyano-(C1-C ₈ )alkyl, (C ₃ C ₈ )cycloalkyl-(C1-C ₈ )alkyl, ( C1-C ₈ ) alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C ₃ C ₈ ) cycloalkylsulfonyl, heterocyclylsulfonyl, aryl-(C ₁ -C ₈ ) alkylsulfonyl, (C ₁ -C ₈ ) alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C ₃ -C ₈ ) cycloalkylcarbonyl, heterocyclylcarbonyl, (C1C ₈ ) alkoxycarbonyl, (C1-C ₈ ) alkoxy, (C ₂ -C ₈ ) alkenyloxy, aryl-(C1-C ₈ ) alkoxycarbonyl, (C 1-C ₈ ) haloalkylcarbonyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, (C ₁ -C ₈ ) haloalkyl, halogen-(C ₂ -C ₈ ) alkynyl, halo-(C ₂ -C ₈ ) alkenyl, (C 1 -C ₈ )alkoxy-(C1-C ₈ )alkyl, amino, (C1-C ₈ )alkylamino, bis[(C1-C ₈ )alkyl]amino, (C ₁ -C ₈ )alkoxy-(C ₁ -C ₈ ) alkoxy-(C ₁ -C ₈ )alkyl, heteroaryl-(C ₁ -C ₈ )alkylsulfonyl, heterocyclyl-(C ₁ C8) alkylsulfonyl, (C2-C8) alkenyloxycarbonyl, (C2-C8) alkynyloxycarbonyl, (C1-C8) alkylaminocarbonyl, (C ₃ -C ₈ )cycloalkylaminocarbonyl, bis-[(C1-C ₈ )alkyl]aminocarbonyl, R ¹² is hydrogen, (C1-C8) alkyl, (C3-C8) cycloalkyl-(C1-C8) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C8) alkoxy-(C1-C8 )alkyl, aryl, aryl-(C1-C8)alkyl, R ¹⁷ O(O)C-(C1-C ₈ )alkyl, R ¹⁵ R ¹⁶ N(O)C(C1-C ₈ )alkyl, R ¹³ is hydrogen, (C1-C8) alkyl, (C1-C8) haloalkyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl-(C1-C8) alkyl, (C2-C8) alkenyl, (C2-C8 )alkynyl, (C1-C8)alkoxy-(C1-C8)alkyl, (C1C8)haloalkoxy-(C1-C8)alkyl, aryl, aryl-(C1-C8)alkyl, heteroaryl, heteroaryl-(C1-C8)alkyl , heterocyclyl, heterocyclyl-(C1-C8) alkyl, (C1-C8) alkylthio-(C1-C8) alkyl, (C1-C8) haloalkylthio-(C1-C8) alkyl, (C1-C8) alkylcarbonyl-(C1- C8) alkyl, R ¹⁷ o(o)C-(C1-C ₈ )alkyl, R ¹⁵ R ¹⁶ N(O)C-(C1-C8) alkyl, R ¹⁵ R ¹⁶ N-(C1C8) alkyl, or R ⁷ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or R ⁹ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or R ¹¹ and R ¹³ when X is NR ¹¹ together with the nitrogen atom to which they are attached form a 4-10 membered monocyclic or bicyclic ring which is fully saturated, or R ¹² and R ¹³ if X is NOR ¹² , together with the nitrogen atom to which they are attached, form a fully saturated 4-10-membered monocyclic or bicyclic ring, R ¹⁴ is fluorine, R ¹⁵ and R ¹⁶ are the same or different and are independently hydrogen, (C1C8) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C8) cyanoalkyl, (C1-C10) haloalkyl, (C2 -C8) haloalkenyl, (C2-C8) haloalkynyl, (C3-C10) cycloalkyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4-C10) halocycloalkenyl, (C1-C8) alkoxy-(C1- C8) alkyl, (C1-C8) haloalkoxy-(C1C8) alkyl, (C1-C8) alkylthio-(C1-C8) alkyl, (C1-C8) haloalkylthio-(C1-C8) alkyl, (C1-C8) alkoxy -(C1C8) haloalkyl, aryl, aryl-(C1-C8) alkyl, heteroaryl, heteroaryl-(C1-C8) alkyl, (C3-C8) cycloalkyl-(C1C8) alkyl, (C4-C10) cycloalkenyl-(C1- C8) alkyl, COR ¹⁷ , SO2R ¹⁸ , (C1-C ₈ ) alkyl-HNO ₂ S-, (C ₃ -C ₈ ) cycloalkylHNO ₂ S-, heterocyclyl, (C ₁ -C ₈ ) alkoxycarbonyl-(C ₁ - C ₈ )alkyl, (C ₁ -C ₈ )alkoxycarbonyl, aryl-(C ₁ C ₈ )alkoxycarbonyl-(C ₁ -C ₈ )alkyl, aryl-(C ₁ -C ₈ )alkoxycarbonyl, heteroaryl-(C ₁ - C ₈ ) alkoxycarbonyl, (C ₂ -C ₈ ) alkenyloxycarbonyl, (C ₂ -C ₈ ) alkynyloxycarbonyl, heterocyclyl-(C ₁ -C ₈ ) alkyl, R ¹⁷ is hydrogen, (C ₁ -C ₈ )alkyl, (C ₂ -C ₈ )alkenyl, (C ₂ -C ₈ )alkynyl, (C ₁ -C ₈ )cyanoalkyl, (C ₁ -C ₁₀ ) haloalkyl , (C ₂ -C ₈ ) haloalkenyl, (C ₂ -C ₈ ) haloalkynyl, (C ₃ -C ₁₀ ) cycloalkyl, (C ₃ C ₁₀ ) halocycloalkyl, (C ₄ -C ₁₀ ) cycloalkenyl, (C ₄ -C ₁₀ ) halocycloalkenyl, (C ₁ -C ₈ ) alkoxy-(C ₁ C8) alkyl, (C1-C8) alkoxy-(C1-C8) haloalkyl, aryl, aryl-(C1-C8) alkyl, heteroaryl, heteroaryl-( C1C8) alkyl, (C3-C8) cycloalkyl-(C1-C8) alkyl, (C4-C10) cycloalkenyl-(C1-C8) alkyl, (C1-C8) alkoxycarbonyl (C1-C8) alkyl, (C2-C8) alkenyloxycarbonyl-(C1-C8) alkyl, aryl-(C1-C8) alkoxycarbonyl-(C1-C8) alkyl, hydroxycarbonyl-(C1-C8) alkyl, heterocyclyl, heterocyclyl-(C1-C8) alkyl, R ¹⁸ is hydrogen, (C1-C8) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C8) cyanoalkyl, (C1-C10) haloalkyl, (C2-C8) haloalkenyl, (C2 -C8) haloalkynyl, (C3-C10) cycloalkyl, (C3C ₁₀ ) halocycloalkyl, (C ₄ -C ₁₀ ) cycloalkenyl, (C ₄ -C ₁₀ ) halocycloalkenyl, (C ₁ -C ₈ ) alkoxy-(C ₁ C ₈ )alkyl, (C ₁ -C ₈ )alkoxy-(C ₁ -C ₈ )haloalkyl, aryl, aryl-(C ₁ -C ₈ )alkyl, heteroaryl, heteroaryl-(C ₁ - 96 042989 C ₈ )alkyl, heterocyclyl-(C1-C ₈ )alkyl, (C ₃ -C ₈ )cycloalkyl-(C1-C ₈ )alkyl, (C ₄ -C ₁₀ )cycloalkenyl-(C1C8) alkyl, NR15R ¹⁶ , where aryl means a mono-, bi- or polycyclic aromatic system containing 6-14 carbon atoms in the ring, heterocyclyl contains at least one heterocyclic ring that is saturated, unsaturated, partially saturated and contains 3-9 ring atoms and 1-4 heteroatoms , selected from the group consisting of N, O and S, heteroaryl means fully unsaturated aromatic heterocyclic 5-7-membered rings containing 1-4 identical or different heteroatoms selected from O, S or N. 2. A compound of general formula (I) according to claim 1 and/or a salt thereof, characterized in that R ¹ is (C1-C ₇ )alkyl, R ² is hydrogen, (C1-C ₇ )alkyl, R ³ is halogen, R ⁴ is halogen, R ⁵ and R ⁶ are independently hydrogen, halogen, (C1-C7)alkyl, (C3-C7)cycloalkyl, (C3C7)cycloalkyl-(C1-C7)alkyl, (C2-C7)alkenyl, (C2-C7) alkynyl, (C1-C10) haloalkyl, (C2-C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4-C10) halocycloalkenyl, (C1-C7) alkoxy , (C1-C7) alkoxy-(C1-C7) alkyl, (C1-C7) alkoxy-(C1-C7) haloalkyl, (C1-C7) haloalkoxy-(C1-C7) haloalkyl, (C1-C7) haloalkoxy-(C1 -C7)alkyl, aryl, aryl-(C1-C7)alkyl, heteroaryl, heteroaryl-(C1-C7)alkyl, (C4-C10)cycloalkenyl-(C1-C7)alkyl, heterocyclyl, heterocyclyl(C1-C7)alkyl , (C1-C7)alkylthio-(C1-C7)alkyl, (C1-C7)haloalkylthio-(C1-C7)alkyl, (C1-C7)alkylcarbonyl-(C1-C7)alkyl, C(O)OR ¹⁷ , C(O)NR ¹⁵ R ¹⁶ , C(O)R ¹⁷ , R ¹⁷ O(O)C-(C1-C7)alkyl, R ¹⁵ R ¹⁶ N(O)C-(CiC7)alkyl, R ¹⁵ R ¹⁶ N-(C ₁ -C ₇ )alkyl, or R ⁵ and R ⁶ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3-10 membered monocyclic or bicyclic ring or m is 0, p is 0, 1, 2, 3, X is O (oxygen), or NR ¹¹ or NOR ¹² moieties, wherein R ¹¹ and R ¹² in NR ¹¹ and NOR ¹² moieties independently have the meanings as defined below, R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are independently hydrogen, fluoro, (C1-C7) alkyl, (C3-C7) cycloalkyl, (C3-C7) cycloalkyl-(C1-C7) alkyl, (C2-C7 )alkenyl, (C2-C7) alkynyl, (C1-C10) haloalkyl, (C2-C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4-C10) halocycloalkenyl, (C1-C7) alkoxy-(C1-C7) haloalkyl, (C1-C7) haloalkoxy-(C1-C7) haloalkyl, aryl, aryl-(C1-C7) alkyl, heteroaryl, heteroaryl-(C1-C7) alkyl, (C4-C10) cycloalkenyl-(C1-C7) alkyl, heterocyclyl, heterocyclyl-(C1-C7) alkyl, R ¹⁷ O-(C1-C ₇ )alkyl, R ¹⁸ S-(C ₁ -C ₇ ) alkyl, (C1-C ₇ )alkylcarbonyl-(C1C7) alkyl, C(O)OR ¹⁷ , C(O)NR ¹⁵ R ¹⁶ , C(O)R ¹⁷ , R ¹⁷ O(O)C-(C1-C7 )alkyl, R ¹⁵ R ¹⁶ N(O)C-(C1-C7)alkyl, R ¹⁵ R ¹⁶ N(C1-C7)alkyl, or R ⁵ and R ⁷ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 8-membered monocyclic or bicyclic ring, or R ⁷ and R ⁸ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form an exomethylene group, or R ⁷ and R ⁹ together with the carbon atoms to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring, R ¹¹ is hydrogen, (C1-C ₇ )alkyl, (C ₃ -C ₇ )cycloalkyl, cyano-(C1-C ₇ )alkyl, (C ₃ C7) cycloalkyl-(C1-C7) alkyl, (C1- C7) alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (С3С ₇ ) cycloalkylsulfonyl, heterocyclylsulfonyl, aryl-(С ₁ -С ₇ ) alkylsulfonyl, (С ₁ -С ₇ ) alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (С ₃ -С ₇ ) cycloalkylcarbonyl, heterocyclylcarbonyl , (C ₁ -C ₇ ) alkoxycarbonyl, (C ₁ -C ₇ ) alkoxy, (C ₂ -C ₇ ) alkenyloxy, aryl-(C ₁ -C ₇ ) alkoxycarbonyl, (C ₁ -C ₇ ) haloalkylcarbonyl, (C ₂ -C ₇ ) alkenyl, (C ₂ -C ₇ ) alkynyl, (C ₁ -C ₇ ) haloalkyl, halogen-(C ₂ -C ₇ ) alkynyl, halogen (C ₂ -C ₇ ) alkenyl, (C ₁ - C ₇ )alkoxy-(C ₁ -C ₇ )alkyl, amino, (C1-C ₇ )alkylamino, bis[(C1-C ₇ )alkyl]amino, (C1C ₇ )alkoxy-(C ₁ -C ₇ )alkoxy -(C ₁ -C ₇ )alkyl, heteroaryl-(C ₁ -C ₇ )alkylsulfonyl, heterocyclyl-(C ₁ -C ₇ )alkylsulfonyl, (C2-C7) alkenyloxycarbonyl, (C2-C7) alkynyloxycarbonyl, (C1-C7 )alkylaminocarbonyl, (C3C7)cycloalkylaminocarbonyl, bis-[(C1-C7)alkyl]aminocarbonyl, R ¹² is hydrogen, (C1-C7) alkyl, (C3-C7) cycloalkyl-(C1-C7) alkyl, (C2-C7) alkenyl, (C2-C7) alkynyl, (C1-C7) alkoxy-(C1-C7) )alkyl, aryl, aryl-(C1-C7)alkyl, R ¹⁷ O(O)C-(C1-C ₇ )alkyl, R ¹⁵ R ¹⁶ N(O)C(C1-C7)alkyl, R ¹³ is hydrogen, (C1-C ₇ )alkyl, (C1-C ₇ )haloalkyl, (C ₃ -C ₇ )cycloalkyl, (C ₃ C ₇ )cycloalkyl-(C ₁ -C ₇ )alkyl, (C ₂ -C ₇ )alkenyl, (C ₂ -C ₇ )alkynyl, (C ₁ -C ₇ )alkoxy-(C ₁ -C ₇ )alkyl, (C ₁ -C ₇ ) haloalkoxy-(C ₁ -C ₇ ) alkyl, aryl, aryl-(C ₁ -C ₇ )alkyl, heteroaryl, heteroaryl-(C ₁ -C ₇ )alkyl, heterocyclyl, - 97 042989 heterocyclyl-(C1-C ₇ )alkyl, (C1-C ₇ )alkylthio-(C1-C ₇ )alkyl, (C1-C ₇ )haloalkylthio-(C1-C ₇ )alkyl, (C1C ₇ )alkylcarbonyl -(C1-C ₇ )alkyl, R ¹⁷ O(O)C-(C1-C7)alkyl, R ¹⁵ R ¹⁶ N(O)C-(C1-C ₇ )alkyl, R ¹⁵ R ¹⁶ N-(c1C ₇ ) alkyl, or R ⁷ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or R ⁹ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or R ¹¹ and R ¹³ when X is NR ¹¹ together with the nitrogen atom to which they are attached form a 4-10 membered monocyclic or bicyclic ring which is fully saturated, or R ¹² and R ¹³ if X is NOR ¹² , together with the nitrogen atom to which they are attached, form a fully saturated 4-10-membered monocyclic or bicyclic ring, R ¹⁴ is fluorine, R ¹⁵ and R ¹⁶ are the same or different and are independently hydrogen, (C1C7) alkyl, (C2-C7) alkenyl, (C2-C7) alkynyl, (C1-C7) cyanoalkyl, (C1-C10) haloalkyl, (C2C7 ) haloalkenyl, (C2-C7) haloalkynyl, (C3-C10) cycloalkyl, (C3-C10) halocycloalkyl, (C4C10) cycloalkenyl, (C4-C10) halocycloalkenyl, (C1-C7) alkoxy-(C1-C7) alkyl, (C1-C7) haloalkoxy(C1-C7) alkyl, (C1-C7) alkylthio-(C1-C7) alkyl, (C1-C7) haloalkylthio-(C1-C7) alkyl, (C1-C7) alkoxy-(C1C7) ) haloalkyl, aryl, aryl-(C1-C7) alkyl, heteroaryl, heteroaryl-(C1-C7) alkyl, (C3-C7) cycloalkyl-(C1C7) alkyl, (C4-C10) cycloalkenyl-(C1-C7) alkyl , COR ¹⁷ , SO2R ¹⁸ , (C1-C ₇ )alkyl-HNO ₂ S-, (C ₃ -C ₇ )cycloalkylHNO2S-, heterocyclyl, (C1-C7) alkoxycarbonyl-(C1-C7) alkyl, (C1-C7 )alkoxycarbonyl, aryl-(C1C7)alkoxycarbonyl-(C1-C7)alkyl, aryl-(C1-C7)alkoxycarbonyl, heteroaryl-(C1-C7)alkoxycarbonyl, (C2-C7)alkenyloxycarbonyl, (C2-C7)alkynyloxycarbonyl, heterocyclyl -(C1-C7)alkyl, R ¹⁷ is hydrogen, (C1-C7) alkyl, (C2-C7) alkenyl, (C2-C7) alkynyl, (C1-C7) cyanoalkyl, (C1-C7) haloalkyl, (C2-C7) haloalkenyl, (C2 -C7) haloalkynyl, (C3-C10) cycloalkyl, (C3C ₁₀ ) halocycloalkyl, (C ₄ -C ₁₀ ) cycloalkenyl, (C ₄ -C ₁₀ ) halocycloalkenyl, (C ₁ -C ₇ ) alkoxy-(C ₁ C ₇ )alkyl, (C ₁ -C ₇ )alkoxy-(C ₁ -C ₇ )haloalkyl, aryl, aryl-(C ₁ -C ₇ )alkyl, heteroaryl, heteroaryl-(C ₁ C ₇ )alkyl, (C ₃ - C ₇ )cycloalkyl-(C ₁ -C ₇ )alkyl, (C ₄ -C ₁₀ )cycloalkenyl-(C ₁ -C ₇ )alkyl, (C ₁ -C ₇ )-alkoxycarbonyl (C ₁ -C ₇ )alkyl, (C ₂ -C ₇ )alkenyloxycarbonyl-(C ₁ -C ₇ )alkyl, aryl-(C ₁ -C ₇ )alkoxycarbonyl-(C ₁ -C ₇ )alkyl, hydroxycarbonyl-(C ₁ -C ₇ )alkyl, heterocyclyl , heterocyclyl-(C ₁ -C ₇ )alkyl, R ¹⁸ is hydrogen, (C1-C ₇ )alkyl, (C ₂ -C ₇ )alkenyl, (C ₂ -C ₇ )alkynyl, (C1-C ₇ )cyanoalkyl, (C1-C10) haloalkyl, (C2- C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C10) cycloalkyl, (C3C ₁₀ ) halocycloalkyl, (C ₄ -C ₁₀ ) cycloalkenyl, (C ₄ -C ₁₀ ) halocycloalkenyl, (C1-C ₇ ) alkoxy- (C1C7) alkyl, (C1-C7) alkoxy-(C1-C7) haloalkyl, aryl, aryl-(C1-C7) alkyl, heteroaryl, heteroaryl-(C1-C7) alkyl, heterocyclyl-(C1-C7) alkyl, (C3 -C7) cycloalkyl-(C1-C7) alkyl, (C4-C10) cycloalkenyl-(C1C7) alkyl, NR15R ¹⁶ . 3. A compound of general formula (I) according to claim 1 and/or a salt thereof, characterized in that R ¹ is (C1-C ₆ )alkyl, R ² is hydrogen, (C1-C ₆ )alkyl, R ³ is halogen, R ⁴ is halogen, R ⁵ and R ⁶ are independently hydrogen, halogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C3C6)cycloalkyl-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6) alkynyl, (C1-C10) haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4-C10) halocycloalkenyl, (C1-C6) alkoxy , (C1-C6) alkoxy-(C1-C6) alkyl, (C1-C6) alkoxy-(C1-C6) haloalkyl, (C1-C6) haloalkoxy-(C1-C6) haloalkyl, (C1-C6) haloalkoxy-(C1 -C6)alkyl, aryl, aryl-(C1-C6)alkyl, heteroaryl, heteroaryl-(C1-C6)alkyl, (C4-C10)cycloalkenyl-(C1-C6)alkyl, heterocyclyl, heterocyclyl(C1-C6)alkyl , (C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)haloalkylthio-(C1-C6)alkyl, (C1-C6)alkylcarbonyl-(C1-C6)alkyl, C(O)OR ¹⁷ , C(O)NR ¹⁵ R ¹⁶ , C(O)R ¹⁷ , R ¹⁷ O(O)C-(C1-C6)alkyl, R ¹⁵ R ¹⁶ N(O)C-(CiC6)alkyl, R ¹⁵ R ¹⁶ N-(C ₁ -C ₆ )alkyl, or R ⁵ and R ⁶ together with the carbon atom to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring, m is 0, p is 0, 1, 2, 3, X is O (oxygen), or NR ¹¹ or NOR ¹² moieties, wherein R ¹¹ and R ¹² in NR ¹¹ and NOR ¹² moieties independently have the meanings as defined below, R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are independently hydrogen, fluorine, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl-(C1-C6) alkyl, (C2-C6 )alkenyl, (C2-C6) alkynyl, (C1-C10) haloalkyl, (C2C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4C10) halocycloalkenyl, (C1 -C6) alkoxy-(C1-C6) haloalkyl, (C1-C6) haloalkoxy-(C1-C6) haloalkyl, aryl, aryl-(C1-C6) alkyl, heteroaryl, heteroaryl-(C1-C6) alkyl, (C4 -C10) cycloalkenyl-(C1-C6) alkyl, heterocyclyl, heterocyclyl-(C1-C6) alkyl, R ¹⁷ O-(C1-C ₆ ) alkyl, R ¹⁸ S-(C ₁ -C ₆ ) alkyl, (C1 -C ₆ )alkylcarbonyl- 98 042989 (C1-Cb)alkyl, C(O)OR ¹⁷ , C(O)NR ¹⁵ R ¹⁶ , C(O)R ¹⁷ , R ¹⁷ O(O)C-(C1-C6 )alkyl, R ¹⁵ R ¹⁶ N(O)C-(C1-C6)alkyl, R ¹⁵ R ¹⁶ N-(C ₁ -C ₆ )alkyl, or R ⁵ and R ⁷ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 8-membered monocyclic or bicyclic ring, or R ⁷ and R ⁸ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form an exomethylene group, or R ⁷ and R ⁹ together with the carbon atoms to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring, R ¹¹ is hydrogen, (C1-C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, cyano-(C1-C ₆ )alkyl, (C ₃ C ₆ )cycloalkyl-(C1-C ₆ )alkyl, ( C1-C ₆ )alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C ₃ C6) cycloalkylsulfonyl, heterocyclylsulfonyl, aryl-(C1-C6) alkylsulfonyl, (C1-C6) alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C ₃ -C ₆ ) cycloalkylcarbonyl, heterocyclylcarbonyl , (C ₁ -C ₆ )alkoxycarbonyl, (C1-C ₆ )alkoxy, (C ₂ -C ₆ )alkenyloxy, aryl-(C1-C ₆ )alkoxycarbonyl, (C1-C ₆ )haloalkylcarbonyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₁ -C ₆ ) haloalkyl, halogen-(C ₂ -C ₆ ) alkynyl, halogen-(C ₂ -C ₆ ) alkenyl, (C 1 -C ₆ ) alkoxy-(C1-C ₆ )alkyl, amino, (C1-C ₆ )alkylamino, bis[(C1-C ₆ )alkyl]amino, (C ₁ -C ₆ )-alkoxy-(C ₁ -C ₆ )alkoxy -(C ₁ -C ₆ )alkyl, heteroaryl-(C ₁ -C ₆ )alkylsulfonyl, heterocyclyl-(C ₁ C ₆ )alkylsulfonyl, (C ₂ -C ₆ )alkenyloxycarbonyl, (C ₂ -C ₆ )alkynyloxycarbonyl, ( C ₁ -C ₆ )alkylaminocarbonyl, (C3-C6)cycloalkylaminocarbonyl, bis-[(C1-C6)alkyl]aminocarbonyl, R ¹² is hydrogen, (C1-C6) alkyl, (C3-C6) cycloalkyl-(C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy-(C1-C6 )alkyl, aryl, aryl-(C1-C6)alkyl, R ¹⁷ O(O)C-(C1-C ₆ )alkyl, R ¹⁵ R ¹⁶ N(O)C(C1-C6)alkyl, R ¹³ is hydrogen, (C1-C6) alkyl, (C1-C6) haloalkyl, (C3-C6) cycloalkyl, (C3C6) cycloalkyl-(C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6 )alkynyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C1C6)haloalkoxy-(C1-C6)alkyl, aryl, aryl-(C1-C6)alkyl, heteroaryl, heteroaryl-(C1-C6)alkyl , heterocyclyl, heterocyclyl-(C1-C6) alkyl, (C1-C6) alkylthio-(C1-C6) alkyl, (C1-C6) haloalkylthio-(C1-C6) alkyl, (C1-C6) alkylcarbonyl-(C1- C6)alkyl, R ¹⁷ O(O)C-(C1-C6)alkyl, R ¹⁵ R ¹⁶ N(O)C-(C1-C6)alkyl, R ¹⁵ R ¹⁶ N-(CiC6)alkyl, or R ⁷ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or R ⁹ and R ¹³ together with the atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or R ¹¹ and R ¹³ when X is NR ¹¹ together with the nitrogen atom to which they are attached form a 4-10 membered monocyclic or bicyclic ring which is fully saturated, or R ¹² and R ¹³ if X is NOR ¹² , together with the nitrogen atom to which they are attached, form a fully saturated 4-10-membered monocyclic or bicyclic ring, R ¹⁴ is fluorine, R ¹⁵ and R ¹⁶ are the same or different and are independently hydrogen, (C1C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) cyanoalkyl, (C1-C10) haloalkyl, (C2C6 ) haloalkenyl, (C2-C6) haloalkynyl, (C3-C10) cycloalkyl, (C3-C10) halocycloalkyl, (C4C10) cycloalkenyl, (C4-C10) 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-(C1C6) ) haloalkyl, aryl, aryl-(C1-C6) alkyl, heteroaryl, heteroaryl-(C1-C6) alkyl, (C3-C6) cycloalkyl-(C1C6) alkyl, (C4-C10) cycloalkenyl-(C1-C6) alkyl , COR ¹⁷ , SO2R ¹⁸ , (C1-C ₆ )alkyl-HNO ₂ S-, (C ₃ -C ₆ )cycloalkylHNO2S-, heterocyclyl, (C1-C ₆ )alkoxycarbonyl-(C1-C ₆ )alkyl, (C1 -C ₆ )alkoxycarbonyl, aryl-(C1C ₆ )alkoxycarbonyl-(C ₁ -C ₆ )alkyl, aryl-(C ₁ -C ₆ )alkoxycarbonyl, heteroaryl-(C ₁ -C ₆ )alkoxycarbonyl, (C ₂ -C ₆ ) alkenyloxycarbonyl, (C ₂ -C ₆ ) alkynyloxycarbonyl, heterocyclyl-(C ₁ -C ₆ ) alkyl, R ¹⁷ is hydrogen, (C ₁ -C ₆ )alkyl, (C ₂ -C ₆ )alkenyl, (C ₂ -C ₆ )alkynyl, (C ₁ -C ₆ )cyanoalkyl, (C ₁ -C ₁₀ ) haloalkyl , (C ₂ -C ₆ ) haloalkenyl, (C ₂ -C ₆ ) haloalkynyl, (C ₃ -C ₁₀ ) cycloalkyl, (C ₃ C ₁₀ ) halocycloalkyl, (C ₄ -C ₁₀ ) cycloalkenyl, (C ₄ -C ₁₀ ) halocycloalkenyl, (C ₁ -C ₆ ) alkoxy-(C ₁ C ₆ ) alkyl, (C ₁ -C ₆ ) alkoxy-(C ₁ -C ₆ ) haloalkyl, aryl, aryl-(C ₁ -C ₆ ) alkyl _heteroaryl (C1-C6) alkyl, (C2-C6) alkenyloxycarbonyl-(C1-C6) alkyl, aryl-(C1-C6) alkoxycarbonyl-(C1C6) alkyl, hydroxycarbonyl-(C1-C6) alkyl, heterocyclyl, heterocyclyl-(C1 -C6) alkyl, R ¹⁸ is hydrogen, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) cyanoalkyl, (C1-C10) haloalkyl, (C2-C6) haloalkenyl, (C2 -C6) haloalkynyl, (C3-C10) cycloalkyl, (C3C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4-C10) halocycloalkenyl, (C1-C6) alkoxy-(C1C ₆ ) alkyl, (C ₁ -C ₆ )alkoxy-(C ₁ -C ₆ )haloalkyl, aryl, aryl-(C ₁ -C ₆ )alkyl, heteroaryl, heteroaryl-(C ₁ C ₆ )alkyl, heterocyclyl-(C ₁ -C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl-(C ₁ -C ₆ )alkyl, (C ₄ -C ₁₀ )cycloalkenyl-(C ₁ - 99 042989 C6)alkyl, NR ¹⁵ R ¹⁶ . 4. A compound of general formula (I) according to claim 1 and/or a salt thereof, characterized in that R ¹ is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2methylpropyl, 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, 2methylpentyl, 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, 1,1,2trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1- methylpropyl, 1-ethyl-2-methylpropyl, R ² is hydrogen, methyl, ethyl, n-propyl, isopropyl, R ³ is fluorine, chlorine, bromine, R ⁴ is halogen, R ⁵ and R ⁶ are independently hydrogen, fluoro, methyl, ethyl, n-propyl, 1-methylethyl, nbutyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2- methylbutyl, 3methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex- 4-yl, 3spiro[2.3]hex-5-yl, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, 1-methylcyclopropyl, 2- methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1'bi(cyclopropyl)-1-yl, 1,1'-bi(cyclopropyl)-2-yl, 2'-methyl-1,1' -bi(cyclopropyl)-2-yl, 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3dimethylcyclobut-1-yl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 3,3difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocycloprop-1-yl, 2fluorocycloprop-1-yl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1- vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2methoxycyclohexyl, 3-methoxycyclohexyl, 2-fluorocycloprop-1-yl, 4-fluorocyclohexyl, 4,4difluorocyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl- 2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1methyl-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, 1,3dimethyl-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, 2ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1ethyl-2-methyl-2- propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl- 2-butynyl, 1-methyl-3-butynyl, 2methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl1-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, 1-ethyl-1-methyl-2-propynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n- propyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, methoxy-n-propyl, methoxydifluoromethyl, ethoxydifluoromethyl, n-propyloxydifluoromethyl, n-butyloxydifluoromethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, phenyl, 2-fluorophenyl, 3- fluorophenyl, 4-fluorophenyl, 2,4difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5difluorophenyl, 2,4,5-trifluorophenyl, 3,4, 5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, - 100 042989 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5- fluorophenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-bromophenyl, 3-fluoro-4-bromophenyl, 3-chloro-4-bromophenyl, 2-chloro-4-fluorophenyl, 3- chloro-4-fluorophenyl, 2fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6- chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,5-trimethylphenyl, 3,4,5trimethylphenyl, 2,4,6-trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4- trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4-difluoromethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 3,5bis(trifluoromethyl)phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5chlorophenyl, 2-ethoxyphenyl, 3- ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4methylthiophenyl, 2-trifluoromethylthiophenyl, 3-trifluoromethylthiophenyl, 4-trifluoromethylthiophenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-methoxycarbonylphenyl, 3-methoxycarbonylphenyl, 4methoxycarbonylphenyl, 2- ethoxycarbonylphenyl, 3-ethoxycarbonylphenyl, 4-ethoxycarbonylphenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2yl, pyrimidin-5-yl, pyrimidin-4-yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2ylmethyl, pyrimidin-5-ylmethyl, pyrimidin-4-ylmethyl, pyrazin-2-ylmethyl, 3-chloropyrazin- 2-yl, 3-bromopyrazin-2-yl, 3-methoxypyrazin-2-yl, 3-ethoxypyrazin-2-yl, 3-trifluoromethylpyrazin-2-yl, 3-cyanopyrazin-2-yl, naphth-2-yl, naphth-1- yl, quinolin-4-yl, quinolin-6-yl, quinolin-8-yl, quinolin-2-yl, quinoxalin-2-yl, 2-naphthylmethyl, 1-naphthylmethyl, quinolin-4-ylmethyl, quinolin-6- ylmethyl, quinolin-8ylmethyl, quinolin-2-ylmethyl, quinoxalin-2-ylmethyl, pyrazin-2-ylmethyl, 4-chloropyridin-2-yl, 3-chloropyridin-4-yl, 2-chloropyridin-3-yl, 2-chloropyridin- 4-yl, 2-chloropyridin-5-yl, 2,6-dichloropyridin4-yl, 3-chloropyridin-5-yl, 3,5-dichloropyridin-2-yl, 3-chloro-5-trifluoromethylpyridin-2-yl, (4chloropyridin-2-yl)methyl, (3-chloropyridin-4-yl)methyl, (2-chloropyridin-3-yl)methyl, (2-chloropyridin-4yl)methyl, (2-chloropyridin-5-yl)methyl , (2,6-dichloropyridin-4-yl)methyl, (3-chloropyridin-5-yl)methyl, (3,5-dichloropyridin-2-yl)methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, 5-chlorothiophen-2-yl, 5-bromothiophen-2-yl, 4-methylthiophen-2-yl, 3-methylthiophen-2-yl, 5-fluorothiophen- 3-yl, 3,5dimethylthiophen-2-yl, 3-ethylthiophen-2-yl, 4,5-dimethylthiophen-2-yl, 3,4-dimethylthiophen-2-yl, 4chlorothiophen-2-yl, furan-2- yl, 5-methylfuran-2-yl, 5-ethylfuran-2-yl, 5-methoxycarbonylfuran-2-yl, 5-chlorofuran-2-yl, 5-bromofuran-2-yl, thiophan-2-yl, thiophan-3- yl, sulfolan-2-yl, sulfolan-3-yl, tetrahydrothiopyran-4-yl, tetrahydropyran-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 1-(4methylphenyl)ethyl, 1-(3- methylphenyl)ethyl, 1-(2-methylphenyl)ethyl, 1-(4-chlorophenyl)ethyl, 1-(3-chlorophenyl)ethyl, 1-(2-chlorophenyl)ethyl, benzyl, (4-fluorophenyl)methyl, ( 3-fluorophenyl)methyl, (2-fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3,5-difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6difluorophenyl)methyl, (2, 4,5-trifluorophenyl)methyl, (2,4,6-trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4-dichlorophenyl)methyl, (3, 5-dichlorophenyl)methyl, (2,5dichlorophenyl)methyl, (2,6-dichlorophenyl)methyl, (2,4,5-trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, (4-bromophenyl)methyl , (3-bromophenyl)methyl, (2-bromophenyl)methyl, (4-iodophenyl)methyl, (3-iodophenyl)methyl, (2-iodophenyl)methyl, (3-chloro-5-trifluoromethylpyridin-2-yl)methyl , (2-bromo-4-fluorophenyl)methyl, (2-bromo4-chlorophenyl)methyl, (3-bromo-4-fluorophenyl)methyl, (3-bromo-4-chlorophenyl)methyl, (3-bromo-5- fluorophenyl)methyl, (3-bromo-5-chlorophenyl)methyl, (2-fluoro-4-bromophenyl)methyl, (2-chloro-4-bromophenyl)methyl, (3fluoro-4-bromophenyl)methyl, (3-chloro -4-bromophenyl)methyl, (2-chloro-4-fluorophenyl)methyl, (3-chloro-4fluorophenyl)methyl, (2-fluoro-3-chlorophenyl)methyl, (2-fluoro-4-chlorophenyl)methyl, ( 2-fluoro-5-chlorophenyl)methyl, (3-fluoro-4-chlorophenyl)methyl, (3-fluoro-5-chlorophenyl)methyl, (2-fluoro-6-chlorophenyl)methyl, 2-phenylethyl-1-yl , 3trifluoromethyl-4-chlorophenyl, 3-chloro-4-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5difluoropyridin-2-yl, (3,6-dichloropyridin-2-yl)methyl, (4-trifluoromethylphenyl)methyl , (3-trifluoromethylphenyl)methyl, (2-trifluoromethylphenyl)methyl, (4-trifluoromethoxyphenyl)methyl, (3-trifluoromethoxyphenyl)methyl, (2-trifluoromethoxyphenyl)methyl, (4-methoxyphenyl)methyl, (3-methoxyphenyl)methyl, (2-methoxyphenyl)methyl, (4-methylphenyl)methyl, (3-methylphenyl)methyl, (2-methylphenyl)methyl, (4cyanophenyl)methyl, (3-cyanophenyl)methyl, (2-cyanophenyl)methyl, (2, 4-diethylphenyl)methyl, (3,5diethylphenyl)methyl, (3,4-dimethylphenyl)methyl, (3,5-dimethoxyphenyl)methyl, 1-phenylethyl-1-yl, 1-(ochlorophenyl)eth-1-yl, 1,3-thiazol-2-yl, 4-methyl-1,3-thiazol-2-yl, 1,3-thiazol-2-yl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, n-propylthiomethyl, isopropylthiomethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, methylcarbonylmethyl, ethylcarbonylmethyl, n-propylcarbonylmethyl, isopropylcarbonylmethyl, methylcarbonylethyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, npropyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, npropylaminocarbonyl, isopropylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, me - 101 042989 tyl(ethyl)aminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, allylaminocarbonyl, benzylaminocarbonyl, tert-butyloxycarbonylaminocarbonyl, hydroxycarbonylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycar bonylmethyl, isopropyloxycarbonylmethyl, n-butyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, allyloxycarbonylmethyl, benzyloxycarbonylmethyl, aminocarbonylmethyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl , n-propylaminocarbonylmethyl, isopropylaminocarbonylmethyl, dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, methyl(ethyl)aminocarbonylmethyl, cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl, cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl, allylaminocarbonylmethyl, benzylaminocarbonylmethyl, 1-(hydroxycarbonyl yl)eth-1-yl, 1-(methoxycarbonyl)eth-1-yl , 1-(ethoxycarbonyl)eth-1-yl, 1(tert-butyloxycarbonyl)eth-1-yl, 1-(benzyloxycarbonyl)eth-1-yl, 2-(hydroxycarbonyl)eth-1-yl, 2-(methoxycarbonyl )eth-1-yl, 2-(ethoxycarbonyl)eth-1-yl, 2-(tert-butyloxycarbonyl)eth-1-yl, 2-(benzyloxycarbonyl)eth-1-yl, 1-(hydroxycarbonyl)prop-1 -yl, 1-(methoxycarbonyl)prop-1-yl, 1-(ethoxycarbonyl)prop-1-yl, 1-(tert-butyloxycarbonyl)prop-1-yl, 1-(benzyloxycarbonyl)prop-1-yl, 2 (hydroxycarbonyl)prop-1-yl, 2-(methoxycarbonyl)prop-1-yl, 2-(ethoxycarbonyl)prop-1-yl, 2-(tert-butyloxycarbonyl)prop-1-yl, 2-(benzyloxycarbonyl)prop-1 -yl, 1-(hydroxycarbonyl)prop-2-yl, 1(methoxycarbonyl)prop-2-yl, 1-(ethoxycarbonyl)prop-2-yl, 1-(tert-butyloxycarbonyl)prop-2-yl, 1( benzyloxycarbonyl)prop-2-yl, 3-(hydroxycarbonyl)prop-1-yl, 3-(methoxycarbonyl)prop-1-yl, 3(ethoxycarbonyl)prop-1-yl, 3-(tert-butyloxycarbonyl)prop-1 -yl, 3-(benzyloxycarbonyl)prop-1-yl, aminomethyl, 2-aminoeth-1-yl, 1-aminoeth-1-yl, 1-aminoprop-1-yl, 3-aminoprop-1-yl, methylaminomethyl, dimethylaminomethyl, diethylaminomethyl, ethylaminomethyl, isopropylaminomethyl, cyclopropylaminomethyl, cyclobutylaminomethyl, cyclopentylaminomethyl, cyclohexylaminomethyl, methoxycarbonylaminomethyl, ethoxycarbonylaminomethyl, tert-butyloxycarbonylaminomethyl, methylcarbonylaminomethyl, ethylcarbonylaminomethyl, n-propylcarbonylaminomethyl, isopropylcarbonylamino methyl, 2(methylamino)eth-1-yl, 2-(diet-1 -ylamino)eth-1-yl, 2-(diethylamino)eth-1-yl, 2-(ethylamino)eth-1-yl, 2(isopropylamino)eth-1-yl, 2-(cyclopropylamino)eth-1- yl, 2-(cyclobutylamino)eth-1-yl, 2-(cyclopentylamino)eth-1-yl, 2-(cyclohexylamino)eth-1-yl, 2-(methoxycarbonylamino)eth-1-yl, 2-(ethoxycarbonylamino )eth-1-yl, 2-(tert-butyloxycarbonylamino)eth-1-yl, 2-(methylcarbonylamino)eth-1-yl, 2(ethylcarbonylamino)eth-1-yl, 2-(n-propylcarbonylamino)eth- 1-yl, 2-(isopropylcarbonylamino)eth-1-yl, 1-(methylamino)eth-1-yl, 1-(dieth-1-ylamino)eth-1-yl, 1-(diethylamino)eth-1- yl, 1-(ethylamino)eth-1-yl, 1(isopropylamino)eth-1-yl, 1-(cyclopropylamino)eth-1-yl, 1-(cyclobutylamino)eth-1-yl, 1-(cyclopentylamino) eth-1-yl, 1-(cyclohexylamino)eth-1-yl, 1-(methoxycarbonylamino)eth-1-yl, 1-(ethoxycarbonylamino)eth-1-yl, 1-(tert-butyloxycarbonylamino)eth-1- yl, 1-(methylcarbonylamino)eth-1-yl, 1(ethylcarbonylamino)eth-1-yl, 1-(n-propylcarbonylamino)eth-1-yl, 1-(isopropylcarbonylamino)eth-1-yl, or R ⁵ and R ⁶ together with the carbon atom to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring, R ¹⁴ is fluorine, m is 0 and Q is one of the fragments Q-1 - Q-300 below: - 102 042989 Xtr-xAcT^ Q-l Q-2 Q-3 Q-4 Q-5 X _o --xAoyY] ^oX^oy X _o /\A _o y< Q-6 Q-7 Q-8 Q-9 Q-10 o Ο ΐ ° ^ox x) Xo-AyA^ ___ Q-ll Q-12 Q-13 Q-14 Q-15 ° ^x ^0C| ₅ Xo^Ao-yy Q _- 16 Q-17 Q ^- ₁₈ Q-19 Q-20 Q-21 Q-22 Q-23 Q-24 Q-25 Xo^AoyQ >oxAo^s/ X _o DD _o xy AJA- Q-26 Q-27 Q-28 Q-29 Q- ³⁰ Q-31 Q-32 Q-33 Q-34 Q-3 5 ^h oC O Q-3 6 Q-3 7 Q-3 8 Q-3 9 Q-40 z°Uo' ^H xA _o . X ^o ^Do^x / °Do^ AL Q-41 Q-42 Q-43 Q-44 Q-45 xA^ 0 z°Ao^/ X°^L _o y/ χοΑο^ Q-46 Q- ₄₇ Q-48 Q-49 Q-50 Q-51 Q-52 Q-53 Q-54 Q-55x-Ay XX ^XsXci ^Χ^ΧβΓ xAx^ Q-56 Q-57 Q-58 Q-59 Q-50 z^o^L /°Do^ ^°^Uyy ^F /°AAyy ^Br Q-61 Q-62 Q-63 Q-64 Q-65 O | Λ L_x\A, and .0___A _n x^x^ X1 Xx-Xfs and pXy» ^D^C! Q-66 Q-67 Q-68 Q-69 Q-70 - 103 042989 about Υ /-/O- YU Q-71 Q-72 Q-73 Q-74 Q-75 /yYq 0 O Ύ O Q-76 Q-77 Q-78 Q-79 Q-80 YyV /°Y ABOUT Y γ.Α YA Q-81 Q-82 Q-83 Q-84 Q-85 Y^O O Y~ 0 /°v^o ^x ^Y' O Y^ Q-86 Q-87 Q-88 Q-89 Q-90 Ά A O A Υ ^Λ Q-91 Q-92 Q-93 Q-94 Q-95 ySo Y°^ 0 Q-96 Q-97 Q-98 Q-99 Q-100 /°Y ^H o AY -Ya "Ya Q-101 Q-102 Q-103 Q-104 Q-105 Y°O Yx O Yn^ Y^ Q-106 Q-107 Q-108 Q-109 Q-110 - 104 042989 about O ^00^0^- Q-111 Q-112 Q-113 Q-114 Q-115 0 Xq^o^ Q-116 Q-117 Q-118 Q-119 Q-120 M o ^sLAo'I 1 ° Xa ^o χΐχ dgi Au Q-121 Q-122 Q-123 Q-124 Q-125 Aha ^0< ^Xd D^ Q-126 Q-127 Q-128 Q-129 Q-130 o Χ°^Αθ' ^{Η χ} Ά' A- Q-131 Q-132 Q-133 Q-134 Q-135 ,0___JL _n xx_^\ AU Αά Q-136 Q-137 Q-138 Q-139 Q-140 o^~ A /Vyo '-o' Q-141 Q-142 Q-143 Q-144 Q-145 Q-146 Q-147 Q-148 Q-149 Q-150 - 105 042989 Η ABOUT Η ABOUT Η Q-151 Q-152 Q-153 Q-154 Q-155 O O ° H ⁰ 0 H Q-156 Q-157 Q-158 Q-159 Q-160 ABOUT About CF3 Q-161 Q-162 Q-163 Q-164 Q-165 ^Z^CI ⁰ Q-166 Q-167 Q-168 Q-169 Q-170 O I ^A _f: ° no ^Αχι O Q-171 Q-172 Q-173 Q-174 Q-175 ⁰ 1 Ϊ h T jl O I ^h ° !PE k T 1 CI^^CFs Q-176 Q-177 Q-178 Q-179 Q-180 Z°Jn^ ^h H o Η Η ^ ^Ο χΑ _Ν Λ η / ^Ο χΑνΧ Q-181 Q-182 Q-183 Q-184 Q-185 ο I -4χ _Μ ^^^4 ^Η 10 ^Ο^/ΙΙχ,,ΧΧ^ Η V Η ο Ο.___ ^Η 1 ο Η Q-186 Q-187 Q-188 Q-189 Q-190 - 106 042989 O X ° xA _n ^ '- Η o yu A ⁰ ί L ___ ^H U O CI O.___ ⁿ and Q-191 Q-192 Q-193 Q-194 Q-195 O CF ₃ ⁿ and /Cgts _vg O Q-196 Q-197 Q-198 Q-199 Q-200 ___ N/D/AD ⁰¹ N N 11| Q-201 Q-202 Q-203 Q-204 Q-205 /°Ay ^^SRz L___ XY -Chgu about CI Q ^- 206 Q-207 Q-208 Q-209 Q- ₂₁₀ Q- ²¹¹ Q-212 Q-213 Q-214 Q-215 Q-216 Q-217 Q-218 Q-219 Q-220 Η STROKE Η Η ___ Η ^N OD Q-221 Q-222 Q-223 Q-224 Q-225 ____ H Q-226 Q-227 Q-228 Q-229 Q-230 - 107 042989 1 O Ο Ν' O ABOUT S N^ Q-231 Q-232 Q-233 Q-234 Q-235 ^χ 'Άο o o o ° Q-236 Q-237 Q-238 Q-239 Q-240 about 1 X°A o Z°^A|X 1 ABOUT ABOUT Q-241 Q-242 Q-243 Q-244 Q-245 Z°\Aq o ___Jf _N xp xA O^/ A Q-246 Q-247 Q-248 Q-249 Q-250 An Oh H X°Y^o N H O Q-251 Q-252 Q-253 Q-254 Q-255 ^Αγ' \ Z\ _/ ⁰ \ ⁰ Ϊ I Q-256 Q-257 Q- ²⁵⁸ Q-259 Q-260 Q-261 Q-262 Q-263 Q-264 Q-265 x° ^D O o Xq'xAn'P A® oV Z°^N^ A A Q-266 Q-267 Q-268 Q-269 Q-270 - 108 042989 5. A compound of general formula (I) according to claim 1 and/or a salt thereof, characterized in that R ¹ is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2methylpropyl, 1,1-dimethylethyl, n-pentyl, R ² is hydrogen, methyl, ethyl, n-propyl, isopropyl, R ³ is fluorine, chlorine, bromine, R ⁴ is halogen, R ⁵ and R ⁶ are independently hydrogen, fluoro, methyl, ethyl, n-propyl, 1-methylethyl, nbutyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2- methylbutyl, 3methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4- pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1- methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 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, 2methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlordifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2, 2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, methoxy-n-propyl, methoxydifluoromethyl, ethoxydifluoromethyl, n-propyloxydifluoromethyl, n-butyloxydifluoromethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4fluorophenyl, 2,4- difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2- chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5dichlorophenyl, 2,4,5- trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, pyridin-2-yl, pyridin-3yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, furan-2- yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 1-(4-methylphenyl)ethyl, 1-(3-methylphenyl)ethyl, 1-(2-methylphenyl)ethyl, 1-(4-chlorophenyl)ethyl, 1-(3chlorophenyl)ethyl, 1-(2-chlorophenyl)ethyl, benzyl, (4-fluorophenyl)methyl, (3-fluorophenyl)methyl, (2fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3.5 -difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6difluorophenyl)methyl, (2,4,5-trifluorophenyl)methyl, (2,4,6-trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3-109 042989 chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4-dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl, (2,5dichlorophenyl)methyl, (2,6-dichlorophenyl)methyl, (2,4,5-trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, n-propylthiomethyl, isopropylthiomethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, methylcarbonylmethyl, ethylcarbonylmethyl, npropylcarbonylmethyl, isopropylcarbonylmethyl, methylcarbonylethyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, dimethylaminocarbonyl, diethylamino carbonyl, methyl(ethyl)aminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, allylaminocarbonyl, benzylaminocarbonyl, tert-butyloxycarbonylaminocarbonyl, hydroxycarbonylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, n-butyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, allyloxycarbonylmethyl, benzyloxycarbonylmethyl , aminocarbonylmethyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, n-propylaminocarbonylmethyl, isopropylaminocarbonylmethyl, dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, Methyl (ethyl) aminocarbonetil, cyclopropylaminocarbonetil, cyclobotylaminocarbonomethyl, cyclopentilaminocarbonomethyl, cycloglogylaminocylaminocarbonomethyl, allalaminocarbonomethyl, gasylaminocarbonomethyl, 1- (hydroxicarbon) ET-1-l, 1- (methoxycar bonil) ET, 1- ) ET -1 -il, 1-(tert-butyloxycarbonyl)eth-1-yl, 1-(benzyloxycarbonyl)eth-1-yl, 2-(hydroxycarbonyl)eth-1-yl, 2-(methoxycarbonyl)eth-1-yl, 2-(ethoxycarbonyl )eth-1-yl, 2-(tert-butyloxycarbonyl)eth-1-yl, 2-(benzyloxycarbonyl)eth-1-yl, 1-(hydroxycarbonyl)prop-1-yl, 1-(methoxycarbonyl)prop-1 -yl, 1-(ethoxycarbonyl)prop-1-yl, 1-(tert-butyloxycarbonyl)prop-1-yl, 1-(benzyloxycarbonyl)prop-1-yl, 2-(hydroxycarbonyl)prop-1-yl , 2-(methoxycarbonyl)prop-1-yl, 2-(ethoxycarbonyl)prop-1-yl, 2-(tert-butyloxycarbonyl)prop-1-yl, 2-(benzyloxycarbonyl)prop-1-yl, 1-( hydroxycarbonyl)prop-2-yl, 1-(methoxycarbonyl)prop-2-yl, 1-(ethoxycarbonyl)prop-2-yl, 1-(tert-butyloxycarbonyl)prop-2-yl, 1-(benzyloxycarbonyl) prop-2-yl, 3-(hydroxycarbonyl)prop-1-yl, 3-(methoxycarbonyl)prop-1-yl, 3-(ethoxycarbonyl)prop-1-yl, 3-(tert-butyloxycarbonyl)prop-1 -yl, 3-(benzyloxycarbonyl)prop-1-yl, aminomethyl, 2-aminoeth-1-yl, 1-aminoeth-1-yl, 1-aminoprop-1-yl, 3-aminoprop1-yl, methylaminomethyl, dimethylaminomethyl , diethylaminomethyl, ethylaminomethyl, isopropylaminomethyl, cyclopropylaminomethyl, cyclobutylaminomethyl, cyclopentylaminomethyl, cyclohexylaminomethyl, methoxycarbonylaminomethyl, ethoxycarbonylaminomethyl, tert-butyloxycarbonylaminomethyl, methylcarbonylaminomethyl, ethylcarbonylaminomethyl, n-propylcarbonylaminomethyl, isopropylcarbonylaminomethyl, 2 -(methylamino)eth-1-yl, 2-(diet-1 -ylamino)eth-1-yl, 2-(diethylamino)eth-1-yl, 2(ethylamino)eth-1 -yl, 2-(isopropylamino)eth-1 -yl, 2-(cyclopropylamino)eth-1 - yl, 2-(cyclobutylamino)eth1-yl, 2-(cyclopentylamino)eth-1-yl, 2-(cyclohexylamino)eth-1-yl, 2-(methoxycarbonylamino)eth-1-yl, 2(ethoxycarbonylamino)eth- 1-yl, 2-(tert-butyloxycarbonylamino)eth-1-yl, 2-(methylcarbonylamino)eth-1-yl, 2-(ethylcarbonylamino)eth-1-yl, 2-(n-propylcarbonylamino)eth-1-yl , 2-(isopropylcarbonylamino)eth-1-yl, 1-(methylamino)eth-1-yl, 1-(dieth-1-ylamino)eth-1-yl, 1-(diethylamino)eth-1-yl, 1-( ethylamino)eth-1-yl, 1-(isopropylamino)eth-1-yl, 1-(cyclopropylamino)eth-1-yl, 1-(cyclobutylamino)eth-1-yl, 1-(cyclopentylamino)eth-1- yl, 1-(cyclohexylamino)eth-1-yl, 1-(methoxycarbonylamino)eth-1-yl, 1-(ethoxycarbonylamino)eth-1-yl, 1-(tert-butyloxycarbonylamino)eth-1-yl, 1 -(methylcarbonylamino)eth-1-yl, 1-(ethylcarbonylamino)eth-1-yl, 1-(n-propylcarbonylamino)eth-1-yl, 1-(isopropylcarbonylamino)eth-1-yl, or R ⁵ and R ⁶ together with the carbon atom to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring, R ¹⁴ is fluorine, m is 0 and Q is one of the fragments Q-l - Q-300 specified in and.4. 6. The use of one or more compounds of general formula (I) and/or their salts according to any one of claims 1 to 5 as a herbicide in agricultural crops of useful plants and/or ornamental plants. 7. Herbicidal composition, characterized in that the composition contains one or more compounds of formula (I) and/or their salts according to any one of claims 1 to 5 and one or more adjuvants traditionally used for crop protection. 8. A method for controlling harmful plants, characterized in that an effective amount of one or more compounds of formula (I) and/or salts thereof according to any one of claims 1 to 5 or a composition according to claim 7 is applied to plants, plant seeds, soil, in which or on which plants grow, or acreage.