EA042986B1 - SUBSTITUTED THIOPHENILURACILS, THEIR SALTS AND THEIR USE AS HERBICIDES - Google Patents

Description

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

In particular, the present invention relates to substituted thiophenyluracils and their salts, to methods for their preparation and to their use as herbicides, in particular for the control of broadleaf weeds and/or weeds in agricultural crops of useful plants, and/or as plant growth regulators. to influence the growth of 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 undesirable plants have some disadvantages in use, which is that either they (a) do not have a herbicidal effect against specific harmful plants or otherwise insufficient, or (b) have too little range of harmful plants that can be controlled by the active ingredient, or (c) have too low selectivity in crops of useful plants and/or (d) have an 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 certain substituted N-linked aryluracils can be used as active herbicidal ingredients (see EP408382, EP473551, EP648749, US4943309, US5084084, US5127935, WO91/00278, WO95/29168, WO95/30661, WO96/35679, WO97/01541, WO98/25909, WO2001/39597). However, the known aryluracils have a number of disadvantages in their action, in particular with respect to monocotyledonous weeds. A number of combinations of active herbicidal ingredients based on N-linked aryluracils have similarly become known (see DE4437197, EP714602, WO96/07323, WO96/08151, JP11189506). However, the properties of such combinations of active ingredients have not been satisfactory in all aspects.

It is also known that specific N-aryluracils, optionally containing additionally substituted lactic acid groups, can also be used as active herbicidal ingredients (see JP2000/302764, JP2001/172265, US6403534, EP408382). Additionally, it is known that Nariluracils, optionally containing particular additionally substituted thiolactic acid groups, similarly exhibit herbicidal effects (see WO2010/038953, KR2011110420). Particular substituted tetrahydrofuryl esters of N-aryluracils, optionally containing additionally substituted thiolactic acid groups, are described in JP09188676.

In contrast, substituted thiophenyluracils per se have not yet been described. In this work, it was surprisingly 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 salts thereof, 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 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, (C 1 -C ₈ ) alkoxy, (C ₁ -C ₈ ) alkoxy (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) alkoxy (C ₁ -C ₈ ) haloalkyl, (C1-C ₈ ) halogen- 1 042986 alkoxy (C 1 -C ₈ ) haloalkyl, (C ₁ -C ₈ ) haloalkoxy (C ₁ -C ₈ ) alkyl, aryl, aryl (C ₁ - C ₈ ) alkyl, heteroaryl, heteroaryl (C 1 -C ₈ ) alkyl, (C 4 -C 1 ₀ ) cycloalkenyl (C 1 -C ₈ ) alkyl, heterocyclyl, heterocyclyl (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 ) alkylcarbonyl (C ₁ -C ₈ ) alkyl, C (O )OR ¹⁹ , C(O)NR ¹⁷ R ¹⁸ , C(O)R ¹⁹ , R ¹⁹ O(O)C-(C1-C8)alkyl, R ¹⁷ R ¹⁸ N(O)C-(C1-C ₈ )alkyl, R ¹⁷ R ¹⁸ N-(C1C 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, or R ⁵ and R ⁶ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I') below

R ⁷ and R ⁸ are independently hydrogen, halogen, (C1-C8)alkyl, (C3-C8)cycloalkyl, (C3C8)cycloalkyl(C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl . , (C1-C8)haloalkoxy(C1-C8)haloalkyl, (C1-C8)haloalkoxy(C1-C8)alkyl, aryl, aryl(C1-C8)alkyl, heteroaryl, heteroaryl(C1-C8)alkyl, heterocyclyl, heterocyclyl (C1-C8)alkyl, (C1C8)alkylthio(C1-C8)alkyl, (C1-C8)haloalkylthio(C1-C8)alkyl, C(O)OR ¹⁹ , C(O)NR ¹⁷ R ¹⁸ , C(O )R ¹⁹ , R ¹⁹ O(O)C-(C1-C8)alkyl, R ¹⁷ R ¹⁸ N(O)C-(C1-C8)alkyl, R ¹⁷ R ¹⁸ N-(C1-C8)alkyl, or R ⁷ and R ⁸ together with the carbon atom to which they are bonded form a fully saturated or partially saturated 3-10 membered monocyclic or bicyclic ring, or R ⁷ and R ⁸ together with the carbon atom to which they are bonded form a double bond, optionally substituted with R ²² and R ²³ according to formula (I'') below

in which m is 0, n is 0, 1, 2, 3, 4, 5, 6, p is 1, 2, 3,

X is O (oxygen), N (nitrogen), or NR ¹⁵ or NOR ¹⁶ moieties, and wherein R ¹⁵ and R ¹⁶ in NR ¹⁵ and NOR ¹⁶ moieties independently have the meanings as defined below,

Y is O (oxygen) or S (sulphur), SO, SO ₂ , R ¹⁰ and R ¹¹ are independently hydrogen, fluorine, cyano, (C1-C8) alkyl, (C3-C8) cycloalkyl, (C3-C8 )cycloalkyl(C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C10)haloalkyl, aryl, aryl(C1-C8)alkyl, heteroaryl, heteroaryl(C1-C8)alkyl, (C4C10) cycloalkenyl (C1-C8) alkyl, heterocyclyl, heterocyclyl (C1-C8) alkyl, R ¹⁹ O-(C1-C ₈ ) alkyl, R ²⁰ S-(C1C8) alkyl, R ²⁰ SO2-(C ₁ - C ₈ )alkyl, or

R ¹⁰ and R ¹¹ 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 ¹² and R ¹³ are independently hydrogen, fluoro, (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 ¹⁹ O-(C1-C ₈ )alkyl, R ²⁰ S-(C1-C8) alkyl, R ²⁰ SO2-(C ₁ -C ₈ ) alkyl, R ¹⁷ R ¹⁸ N-(C ₁ C8) alkyl, or

R ¹² and R ¹³ 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 ¹⁴ is (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(C1C8)alkyl, aryl, aryl(C1-C8)alkyl, heteroaryl, heteroaryl(C1-C8)alkyl, heterocyclyl, heterocyclyl( C1C8) alkyl, (C1-C8) alkylthio (C1-C8) alkyl, (C1-C8) haloalkylthio (C1-C8) alkyl, R ¹⁷ R ¹⁸ N-(C1-C ₈ ) alkyl, cyano (C1-C ₈ )alkyl, or

R ¹⁰ and R ¹⁴ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or

R ¹² and R ¹⁴ 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 ¹⁵ 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(C1-C ₈ )alkylsulfonyl, (C1-C ₈ )alkylcarbonyl, aryl

- 2 042986 carbonyl, heteroarylcarbonyl, (C ₃ -C ₈ )cycloalkylcarbonyl, heterocyclylcarbonyl, (C1-C ₈ )alkoxycarbonyl, (C1-C ₈ )alkoxy, (C ₂ -C ₈ )alkenyloxy, aryl(C1-C ₈ ) alkoxycarbonyl, (C1-C ₈ ) haloalkylcarbonyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, (C 1-C ₈ ) haloalkyl, halogen (C ₂ -C ₈ ) alkynyl, halogen (C ₂ C ₈ )alkenyl, (C1-C ₈ )alkoxy(C1-C ₈ )alkyl, amino, (C1-C ₈ )alkylamino, bis-[(C1-C ₈ )alkyl]amino, (C ₁ C ₈ )alkoxy (C1-C ₈ ) alkoxy (C 1-C ₈ ) alkyl, heteroaryl (C 1-C ₈ ) alkylsulfonyl, heterocyclyl (C 1-C ₈ ) alkylsulfonyl, (C ₂ -C ₈ ) alkenyloxycarbonyl, (C ₂ -C ₈ ) alkynyloxycarbonyl , (C1-C ₈ )alkylaminocarbonyl, (C ₃ C ₈ )cycloalkylaminocarbonyl, bis-[(C ₁ -C ₈ )alkyl]aminocarbonyl,

R ¹⁶ 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 ¹⁹ O(O)C-(C1-C ₈ )alkyl, R ¹⁷ R ¹⁸ N(O)C(C ₁ -C ₈ )alkyl,

R ¹⁷ and R ¹⁸ are the same or different and are independently hydrogen, (C1C8) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C8) cyanoalkyl, (C1-C1o) 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(C1-C8)alkyl, (C1-C8)alkylthio(C1-C8)alkyl, (C1-C8)haloalkylthio(C1-C8)alkyl, (C1-C8)alkoxy(C1 -C8) haloalkyl, aryl, aryl (C1-C8) alkyl, heteroaryl, heteroaryl (C1-C8) alkyl, (C3-C8) cycloalkyl (C1-C8) alkyl, (C4C10) cycloalkenyl (C1-C8) alkyl, COR ¹⁹ , SO2R ²⁰ , (C1-C ₈ )alkyl-HNO ₂ S-, (C ₃ -C ₈ ) cycloalkyl-HNO ₂ S-, heterocyclyl, (C1-C ₈ ) alkoxycarbonyl-(C1-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 ¹⁹ 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 ₁₀ ) halocycloalkyl, (C ₄ -C ₁₀ ) cycloalkenyl, (C ₄ -C ₁₀ ) halocycloalkenyl, (C1- _C8 )alkoxy(C1- _C8 )alkyl, (C1C8)alkoxy(C1-C8)haloalkyl, aryl, aryl(C1-C8)alkyl, heteroaryl, heteroaryl(C1-C8)alkyl, (C3C8 )cycloalkyl (C1-C8) alkyl, (C4-C10) cycloalkenyl (C1-C8) alkyl, (C1-C8) alkoxycarbonyl-(C1-C8) alkyl, (C ₂ -C ₈ ) alkenyloxycarbonyl-(C ₁ -C ₈ ) alkyl, aryl (C ₁ -C ₈ ) alkoxycarbonyl- (C ₁ -C ₈ ) alkyl, hydroxycarbonyl (C ₁ -C ₈ ) alkyl, heterocyclyl, heterocyclyl (C ₁ -C ₈ ) alkyl,

R ²⁰ 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 ₁ -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 -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, heterocyclyl (C1-C8) alkyl, (C3-C8) cycloalkyl (C1-C8) alkyl, (C4-C10) cycloalkenyl (C1-C8) alkyl, NR ¹⁷ R ¹⁸ ,

R ²¹ is fluoro and

R ²² and R ²³ are independently hydrogen, halogen, (C1-C8) alkyl, (C3-C8) cycloalkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C10) haloalkyl, aryl, or

R ²² and R ²³ together with the carbon atom to which they are bonded form a 3-10 membered monocyclic or bicyclic ring which is saturated, where aryl is a mono-, bi- or polycyclic aromatic system containing 6-14 carbon atoms in ring, 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 is 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, such as p-toluenesulfonic acid, to a basic group, such as 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 sodium hydrogen carbonate 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 R ^a -R ^d independently represent an organic radical, in particular alkyl, aryl, aralkyl or

- 3 042986 alkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C1C ₄ )trialkylsulfonium and (C ₁ -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-C7) haloalkyl, (C2-C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C7) halocycloalkyl, (C4-C7) cycloalkenyl, (C4-C7) 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-C7)cycloalkenyl(C1-C7)alkyl, heterocyclyl, heterocyclyl(C1-C7)alkyl, (C1C7)alkylthio( C1-C7) alkyl, (C1-C7) haloalkylthio(C1-C7) alkyl, (C1-C7) alkylcarbonyl (C1-C7) alkyl, C(O)OR ¹⁹ , C(O)NR ¹⁷ R ¹⁸ , C( O)R ¹⁹ , R ¹⁹ O(O)C-(C1-C7)alkyl, R ¹⁷ R ¹⁸ N(O)C-(C1-C7)alkyl, R ¹⁷ R ¹⁸ N-(Cr 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 to 10-membered monocyclic or bicyclic ring, or

R ⁵ and R ⁶ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I') below

R ⁷ and R ⁸ are independently hydrogen, halogen, (C1-C7) alkyl, (C3-C7) cycloalkyl, (C3C7) cycloalkyl (C1-C7) alkyl, (C2-C7) alkenyl, (C2-C7) alkynyl , (C1-C7) haloalkyl, (C2-C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C7) halocycloalkyl, (C1-C7) alkoxy (C1-C7) alkyl, (C1-C7) alkoxy (C1C7) )haloalkyl, (C1-C7)haloalkoxy(C1-C7)haloalkyl, (C1-C7)haloalkoxy(C1-C7)alkyl, aryl, aryl(C1-C7)alkyl, heteroaryl, heteroaryl(C1-C7)alkyl, heterocyclyl , heterocyclyl (C1-C7) alkyl, (C1C7) alkylthio (C1-C7) alkyl, (C1-C7) haloalkylthio (C1-C7) alkyl, C (O) OR ¹⁹ , C (O) NR ¹⁷ R ¹⁸ , C (O)R ¹⁹ , R ¹⁹ O(O)C-(C1-C ₇ )alkyl, R ¹⁷ R ¹⁸ N(O)C-(C1-C7)alkyl, R ¹⁷ R ¹⁸ N-(C1-C ₇ )alkyl, 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 ⁷ and R ⁸ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I) below

in which m is 0, n is 0, 1, 2, 3, 4, 5, 6, p is 1, 2, 3,

X is O (oxygen), N (nitrogen), or NR ¹⁵ or NOR ¹⁶ moieties, and wherein R ¹⁵ and R ¹⁶ in NR ¹⁵ and NOR ¹⁶ moieties independently have the meanings as defined below,

Y is O (oxygen) or S (sulphur), SO, SO ₂ ,

R ¹⁰ and R ¹¹ are independently hydrogen, fluorine, cyano, (C1-C7) alkyl, (C3-C7) cycloalkyl, (C3-C7) cycloalkyl (C1-C7) alkyl, (C2-C7) alkenyl, (C2 -C7)alkynyl, (C1-C7)haloalkyl, aryl, aryl(C1C7)alkyl, heteroaryl, heteroaryl(C1-C7)alkyl, (C4-C7)cycloalkenyl(C1-C7)alkyl, heterocyclyl, heterocyclyl(C1-C7) )alkyl, R ¹⁹ O-(C1-C ₇ )alkyl, R ²⁰ S-(C1-C7)alkyl, R ²⁰ SO2-(C ₁ -C ₇ )alkyl, or

R ¹⁰ and R ¹¹ 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 ¹² and R ¹³ are independently hydrogen, fluoro, (C1-C7)alkyl, (C3-C7)cycloalkyl, (C3C7)cycloalkyl(C1-C7)alkyl, (C2-C7)alkenyl, (C2-C7)alkynyl , (C1-C7) haloalkyl, (C2-C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C7) halocycloalkyl, (C4-C7) cycloalkenyl, (C4-C7) 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(C1C7) alkyl, R ¹⁹ O-(C1-C ₇ )alkyl, R ²⁰ S-(C1-C7) alkyl, R ²⁰ SO2-(C ₁ -C ₇ ) alkyl, R ¹⁷ R ¹⁸ N-(C ₁ -C ₇ )alkyl, or

- 4 042986

R ¹² and R ¹³ 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 ¹⁴ is (C1-C7) alkyl, (C1-C7) haloalkyl, (C3-C7) cycloalkyl, (C3-C7) 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, R ¹⁷ R ¹⁸ N-(C1-C ₇ ) alkyl, cyano (C1-C ₇ )alkyl, or

R ¹⁰ and R ¹⁴ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or

R ¹² and R ¹⁴ 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 ¹⁵ is hydrogen, (C 1 -C ₇ )alkyl, (C ₃ -C ₇ ) cycloalkyl, cyano(C 1 -C ₇ ) alkyl, (C ₃ C ₇ ) cycloalkyl (C ₁ -C ₇ ) alkyl, (C 1 -C ₇ )alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C ₃ C7) cycloalkylsulfonyl, heterocyclylsulfonyl, aryl(C1-C7) alkylsulfonyl, (C1-C7) 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, (C ₁ -C ₇ ) alkoxy (C ₁ -C ₇ )alkyl, amino, (C1-C ₇ )alkylamino, bis-[(C1-C ₇ )alkyl]amino, (C ₁ -C ₇ )alkoxy(C ₁ -C ₇ )alkoxy(C ₁ - C ₇ )alkyl, heteroaryl (C1-C ₇ ) alkylsulfonyl, heterocyclyl (C1C ₇ ) alkylsulfonyl, (C ₂ -C ₇ ) alkenyloxycarbonyl, (C ₂ -C ₇ ) alkynyloxycarbonyl, (C 1-C ₇ ) alkylaminocarbonyl, (C ₃ -C ₇ )cycloalkylaminocarbonyl, bis-[(C ₁ -C ₇ )alkyl]aminocarbonyl,

R ¹⁶ 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 ¹⁹ O(O)C-(C1-C ₇ )alkyl, R ¹⁷ R ¹⁸ N(O)C(C ₁ -C ₇ )alkyl,

R ¹⁷ and R ¹⁸ are the same or different and are independently hydrogen, (C1C7) alkyl, (C2-C7) alkenyl, (C2-C7) alkynyl, (C1-C7) cyanoalkyl, (C1-C7) haloalkyl, (C2C7 ) haloalkenyl, (C2-C7) haloalkynyl, (C3-C7) cycloalkyl, (C3-C7) halocycloalkyl, (C4C10) cycloalkenyl, (C4-C7) halocycloalkenyl, (C1-C7) alkoxy (C1-C7) alkyl, ( C1-C7) haloalkoxy (C1C7) 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-C7) cycloalkenyl (C1-C7) alkyl, COR ¹⁹ , SO2R ²⁰ , (C1- C ₇ )alkyl-HNO ₂ S-, (C ₃ -C ₇ )cycloalkylHNO2S-, heterocyclyl, (C ₁ -C ₇ )alkoxycarbonyl-(C ₁ -C ₇ )alkyl, (C ₁ -C ₇ )alkoxycarbonyl, aryl (C1C7)alkoxycarbonyl-(C1-C7)alkyl, aryl(C1-C7)alkoxycarbonyl, heteroaryl(C1-C7)alkoxycarbonyl, (C2C7)alkenyloxycarbonyl, (C2-C7)alkynyloxycarbonyl, heterocyclyl(C1-C7)alkyl,

R ¹⁹ 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-C7) cycloalkyl, (C3C ₇ ) halocycloalkyl, (C ₄ -C ₇ ) cycloalkenyl, (C ₄ -C ₇ ) halocycloalkenyl, (C । -C ₇ ) alkoxy (C । -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 ₇ ) 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(C1-C ₇ )alkyl, heterocyclyl, heterocyclyl(C1- C ₇ )alkyl,

R ²⁰ is hydrogen, (C1-C ₇ )alkyl, (C ₂ -C ₇ )alkenyl, (C ₂ -C ₇ ) alkynyl, (C 1 -C ₇ )cyanoalkyl, (C 1 -C ₇ ) haloalkyl, (C ₂ -C ₇ ) haloalkenyl, (C ₂ -C ₇ ) haloalkynyl, (C ₃ -C ₇ ) cycloalkyl, (C ₃ C ₇ ) halocycloalkyl, (C ₄ -C ₇ ) cycloalkenyl, (C ₄ -C ₇ ) halocycloalkenyl , (C । -C ₇ ) alkoxy (C । -C ₇ ) alkyl, (C ₁ -C ₇ ) alkoxy (C ₁ -C ₇ ) haloalkyl, aryl, aryl (C 1-C ₇ ) alkyl, heteroaryl, heteroaryl ( C1-C ₇ )alkyl, heterocyclyl(C1-C ₇ )alkyl, (C ₃ -C ₇ )cycloalkyl(C ₁ -C ₇ )alkyl, (C ₄ -C ₇ )cycloalkenyl(C ₁ -C ₇ )alkyl, ^NR17R18 ,

R ²¹ is fluoro and

R ²² and R ²³ independently represent hydrogen, halogen, (C 1 -C ₇ )alkyl, (C ₃ -C ₇ ) cycloalkyl, (C ₂ C ₇ ) alkenyl, (C ₂ -C ₇ ) alkynyl, (C 1 -C ₇ ) haloalkyl, aryl, or

R ²² and R ²³ together with the carbon atom to which they are attached form a 3-10 membered monocyclic or bicyclic ring which is saturated.

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 independently represent hydrogen, halogen, (C1-C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, (C ₃ C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C 1 -C ₆ ) haloalkyl, (C ₂ -C ₆ ) haloalkenyl, (C ₂ -C ₆ ) haloalkynyl, (C ₃ -C ₆ ) halocycloalkyl, (C1 -C ₆ ) alkoxy, (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl, (C 1 C ₆ ) alkoxy (C ₁ -C ₆ ) haloalkyl, (C ₁ -C ₆ ) haloalkoxy (C ₁ -C ₆ ) haloalkyl, (C1-C ₆ ) haloalkoxy (C1 C ₆ ) alkyl, aryl, aryl (C1-C ₆ ) alkyl, heteroaryl, heteroaryl (C1-C ₆ ) alkyl, heterocyclyl, heterocyclyl (C1 C ₆ ) alkyl, ( C ₁ -C ₆ )alkylthio (C ₁ -C ₆ )alkyl, (C ₁ -C ₆ ) haloalkylthio (C ₁ -C ₆ )alkyl, (C ₁ -C ₆ )alkylcarbonyl (C ₁ - 5 042986

C ₆ )alkyl, C(O)OR ¹⁹ , C(O)NR ¹⁷ R ¹⁸ , C(O)R ¹⁹ , R ¹⁹ O(O)C-(C1-C6) alkyl, R ¹⁷ R ¹⁸ N(O )C-(C1-C ₆ )alkyl, R ¹⁷ R ¹⁸ 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 to 10-membered monocyclic or bicyclic ring, or

R ⁵ and R ⁶ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I') below

R ⁷ and R ⁸ are independently hydrogen, halogen, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl , (C1-C6) haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) halocycloalkyl, (C1-C6) alkoxy (C1-C6) alkyl, (C1-C6) alkoxy (C1C6 ) haloalkyl, (C 1 -C6) haloalkoxy (C 1 -C6) haloalkyl, (C 1 -C6) haloalkoxy (C 1 -C6) alkyl, aryl, aryl (C 1 -C 6) alkyl, heteroaryl, heteroaryl (C 1 -C 6 )alkyl, heterocyclyl, heterocyclyl(C1-C6)alkyl, (C1C6)alkylthio(C1-C6)alkyl, (C1-C6)haloalkylthio(C1-C6)alkyl, C(O)OR ¹⁹ , C(O)NR ¹⁷ R ¹⁸ , C(O)R ¹⁹ , R ¹⁹ O(O)C-(C1-C ₆ )alkyl, R ¹⁷ R ¹⁸ N(O)C-(C1-C6)alkyl, R ¹⁷ R ¹⁸ N-( C1-C ₆ )alkyl, 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 ⁷ and R ⁸ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I') below

in which m is 0, n is 0, 1, 2, 3, 4, 5, 6, p is 1, 2, 3,

X is O (oxygen), N (nitrogen), or NR ¹⁵ or NOR ¹⁶ moieties, and wherein R ¹⁵ and R ¹⁶ in NR ¹⁵ and NOR ¹⁶ moieties independently have the meanings as defined below,

Y is O (oxygen) or S (sulphur), SO, SO ₂ ,

R ¹⁰ and R ¹¹ are independently hydrogen, fluorine, cyano, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (C1-C6) alkyl, (C2-C6) alkenyl, (C2 -C6)alkynyl, (C1-C6)haloalkyl, aryl, aryl(C1C6)alkyl, heteroaryl, heteroaryl(C1-C6)alkyl, (C4-C6)cycloalkenyl(C1-C6)alkyl, heterocyclyl, heterocyclyl(C1-C6 )alkyl, R ¹⁹ O-(C1-C ₆ )alkyl, R ²⁰ S-(C1-C6)alkyl, R ²⁰ SO2-(C ₁ -C ₆ )alkyl, or

R ¹⁰ and R ¹¹ 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 ¹² and R ¹³ independently represent hydrogen, fluorine, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C3C6)cycloalkyl(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl . 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 ¹⁹ O-(C1-C ₆ )alkyl, R ²⁰ S-(C1-C6) alkyl, R ²⁰ SO2-(C ₁ -C ₆ ) alkyl, R ¹⁷ R ¹⁸ N( C ₁ -C ₈ )alkyl, or

R ¹² and R ¹³ 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 (C1-C6) alkyl, (C1-C6) haloalkyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6)alkoxy(C1-C6)alkyl, (C1-C6)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, R ¹⁷ R ¹⁸ N-(C1C ₆ ) alkyl, cyano (C ₁ -C ₆ )alkyl, or

R ¹⁰ and R ¹⁴ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or

R ¹² and R ¹⁴ 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 ¹⁵ is hydrogen, (C ₁ -C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, cyano(C ₁ -C ₆ )alkyl, (C ₃ C ₆ )cycloalkyl(C ₁ -C ₆ )alkyl, (C ₁ -C ₆ )alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C ₃ C ₆ )cycloalkylsulfonyl, heterocyclylsulfonyl, aryl(C ₁ -C ₆ )alkylsulfonyl, (C ₁ -C ₆ )alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C ₃ - C ₆ ) cycloalkylcarbonyl, heterocyclylcarbonyl, (C ₁ -C ₆ ) alkoxycarbonyl, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, aryl (C ₁ -C ₆ ) alkoxycarbonyl, (C ₁ -C ₆ )haloalkylcarbonyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)haloalkyl, halo(C2-C6)alkynyl, halo(C2-6 042986

C _b ) alkenyl, (C1-Cb) alkoxy(C1-Cb) alkyl, amino, (C1-Cb) alkylamino, bis-[(C1-Cb) alkyl] amino, (C1 Cb) alkoxy (C1-C6) alkoxy ( C1-Cb) alkyl, heteroaryl (C1-C _b ) alkylsulfonyl, heterocyclyl (C1C _b ) alkylsulfonyl, (C ₂ -C _b ) alkenyloxycarbonyl, (C ₂ -C _b ) alkynyloxycarbonyl, (C1-C _b ) alkylaminocarbonyl, (C ₃ -C _b ) cycloalkylaminocarbonyl, bis-[(C1-C _b ) alkyl] aminocarbonyl,

R ¹⁶ 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-Cb)alkyl, R ¹⁹ O(O)C-(C1-C _b )alkyl, R ¹⁷ R ¹⁸ N(O)C(C ₁ -C _b )alkyl,

R ¹⁷ and R ¹⁸ are the same or different and are independently hydrogen, (C1C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)cyanoalkyl, (C1-C6)haloalkyl, (C2 -Cb) haloalkenyl, (C2-Cb) haloalkynyl, (C3-Cb) cycloalkyl, (C3-Cb) halocycloalkyl, (C4-C10) cycloalkenyl, (C4Cb) halocycloalkenyl, (C 1 -Cb) alkoxy (C 1 -Cb )alkyl, (C 1 -Cb) haloalkoxy (C1-Cb) alkyl, (C 1 -Cb) alkylthio (C1-Cb) alkyl, (C 1-Cb) haloalkylthio (C 1-Cb) alkyl, (C 1-Cb) alkoxy (C1-C6) haloalkyl, aryl, aryl(C1C6) alkyl, heteroaryl, heteroaryl (C1-C6) alkyl, (C3-C6) cycloalkyl (C1-C6) alkyl, (C4-C6) cycloalkenyl (C1C6) alkyl, COR ¹⁹ , SO2R ²⁰ , (C1-C _b ) alkyl-HNO ₂ S-, (C ₃ -C _b ) cycloalkyl-HNO ₂ S-, heterocyclyl, (C1C _b ) alkoxycarbonyl-(C1-C _b ) alkyl, (C ₁ -C _b ) alkoxycarbonyl, aryl (C ₁ -C _b ) alkoxycarbonyl- (C ₁ -C _b ) alkyl, aryl (C 1 -C _b ) alkoxycarbonyl, heteroaryl (C 1 -C _b ) alkoxycarbonyl, (C ₂ -C _b ) alkenyloxycarbonyl, (C ₂ C _b ) alkynyloxycarbonyl, heterocyclyl (C ₁ -C _b ) alkyl,

R ¹⁹ is hydrogen, (C1-C _b )alkyl, (C ₂ -C _b )alkenyl, (C ₂ -C _b )alkynyl, (C1-C _b )cyanoalkyl, (C ₁ -C ₁₀ ) haloalkyl, ( C ₂ -C _b ) haloalkenyl, (C ₂ -C _b ) haloalkynyl, (C ₃ -C _b ) cycloalkyl, (C ₃ -C _b ) halocycloalkyl, (C ₄ -C _b ) cycloalkenyl, (C ₄ -C _b ) halocycloalkenyl, (C ₁ -C _b ) alkoxy (C ₁ -C _b ) alkyl, (C ₁ Cb) alkoxy (C 1-Cb) haloalkyl, aryl, aryl (C 1-Cb) alkyl, heteroaryl, heteroaryl (C 1-Cb )alkyl, (C3Cb) cycloalkyl (C1-Cb) alkyl, (C4-Cb) cycloalkenyl (C1-Cb) alkyl, (C1-Cb) alkoxycarbonyl-(C1-Cb) alkyl, (C2-Cb) alkenyloxycarbonyl-(C1 -C6)alkyl, aryl(C1-C6)alkoxycarbonyl-(C1-C6)alkyl, hydroxycarbonyl(C1-C6)alkyl, heterocyclyl, heterocyclyl(C1-C6)alkyl,

R ²⁰ is hydrogen, (C1-Cb) alkyl, (C2-Cb) alkenyl, (C2-Cb) alkynyl, (C1-Cb) cyanoalkyl, (C ₁ -C _b ) haloalkyl, (C ₂ -C _b ) haloalkenyl, (C ₂ -C _b ) haloalkynyl, (C ₃ -C _b ) cycloalkyl, (C ₃ -C _b ) halocycloalkyl, (C ₄ -C _b ) cycloalkenyl, (C ₄ -C _b ) halocycloalkenyl, (C ₁ -C _b ) alkoxy (C ₁ -C _b ) alkyl, (C ₁ -C _b ) alkoxy (C ₁ -C _b ) haloalkyl, aryl, aryl (C ₁ -C _b ) alkyl, heteroaryl, heteroaryl (C ₁ - C _b ) alkyl, heterocyclyl (C ₁ -C _b ) alkyl, (C ₃ -C _b ) cycloalkyl (C ₁ -C _b ) alkyl, (C ₄ -C _b ) cycloalkenyl (C ₁ -C _b ) alkyl, NR ¹⁷ R ¹⁸ , R ²¹ is fluorine, and

R ²² and R ²³ are independently hydrogen, halogen, (C ₁ -C _b )alkyl, (C ₃ -C _b ) cycloalkyl, (C ₂ Cb) alkenyl, (C 2 -Cb) alkynyl, (C 1 -Cb) haloalkyl , aryl, or

R ²² and R ²³ together with the carbon atom to which they are attached form a 3-10 membered monocyclic or bicyclic ring which is saturated.

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, 1,1,2trimethylpropyl, 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, 3,3-difluorocyclobut-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, 1-hexenyl, 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, 2-ethyl-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, 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, 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, 3,5-bis(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, 3bromopyrazin- 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, (4-chloropyridin-2 -yl)methyl, (3-chloropyridin-4-yl)methyl, (2-chloropyridin-3-yl)methyl, (2-chloropyridin-4-yl)methyl, (2-chloropyridin-5-yl)methyl, ( 2,6-dichloropyridin-4-yl)methyl, (3-chloropyridin-5-yl)methyl, (3,5-dichloro

- 8 042986 pyridin-2-yl)methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, 5-chlorothiophen2-yl, 5-bromothiophen-2 -yl, 4-methylthiophen-2-yl, 3-methylthiophen-2-yl, 5-fluorothiophenyl-3-yl, 3,5dimethylthiophen-2-yl, 3-ethylthiophen-2-yl, 4,5-dimethylthiophen-2 -yl, 3,4-dimethylthiophen-2-yl, 4-chlorothiophen-2-yl, furan-2-yl, 5-methylfuran-2-yl, 5-ethylfuran-2-yl, 5-methoxycarbonylfuran-2-yl, 5chlorofuran -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-(4-methylphenyl)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, (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-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, 3-trifluoromethyl-4-chlorophenyl, 3-chloro-4-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5-difluoropyridine-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, or

R ⁵ and R ⁶ 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 ⁵ and R ⁶ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I') below

R ⁷ and R ⁸ independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1- methylbutyl, 2methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2dimethylbutyl, 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-2methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobut-1-yl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 3,3-difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, 2-fluorocycloprop-1-yl, 4fluorocyclohexyl, 4,4-difluorocyclohexyl, 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-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl- 2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2methyl- 1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl- 4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2- butenyl, 1.2

- 9 042986 dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl3-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-1butenyl, 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, 1-ethyl-2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl , 2butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2butynyl, 1-methyl-3-butynyl, 2-methyl-3 -butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl -2-pentynyl, 1-methyl-3pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl4-pentynyl, 4 -methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl -3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, trifluoromethyl , pentafluoroethyl, 1,1,2,2tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlordifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2difluoroethyl, 2,2,2-trifluoroethyl, difluoro -tert-butyl, chloromethyl, bromomethyl, methoxy, ethoxy, npropyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, npropyloxymethyl, 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, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl , 2,3difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2 ,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6trichlorophenyl, 2 -bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-bromo4-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, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2fluoro-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, 3,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5 -dimethoxyphenyl, 2,6dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,4,5trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2-trifluoromethoxyphenyl , 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4-difluoromethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2difluoromethylphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 3,5-bis(trifluoromethyl)phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy- 5-chlorophenyl, 2-ethoxyphenyl, 3ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2trifluoromethylthiophenyl, 3-trifluoromethylthiophenyl, 4-trifluoromethylthiophenyl, 2-ethylphenyl, 3ethylphenyl, 4-ethylphenyl, 2-methoxycarbonylphenyl, 3-methoxycarbonylphenyl, 4-methoxycarbonylphenyl, 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-2-yl, pyrimidin-5-yl, pyrimidin-4-yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2-ylmethyl, pyrimidin-5-ylmethyl, pyrimidin- 4-ylmethyl, pyrazin-2-ylmethyl, 3-chloropyrazin-2-yl, 3-bromopyrazin-2-yl, 3-methoxypyrazin2-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, 1naphthylmethyl, quinolin-4-ylmethyl, quinolin-6-ylmethyl, quinolin-8-ylmethyl, 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-dichloropyridin-4-yl, 3-chloropyridin-5-yl, 3,5- dichloropyridin-2-yl, 3-chloro-5-trifluoromethylpyridin-2-yl, (4-chloropyridin-2-yl)methyl, (3-chloropyridin-4yl)methyl, (2-chloropyridin-3-yl)methyl, ( 2-chloropyridin-4-yl)methyl, (2-chloropyridin-5-yl)methyl, (2,6dichloropyridin-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-dimethylthiophen-2-yl, 3-ethylthiophen-2yl, 4,5-dimethylthiophen-2-yl, 3, 4-dimethylthiophen-2-yl, 4-chlorothiophen-2-yl, furan-2-yl, 5-methylfuran-2yl, 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-(4-methylphenyl)ethyl, 1-(3-methylphenyl)ethyl, 1-(2methylphenyl)ethyl, 1-(4-chlorophenyl)ethyl, 1-(3-chlorophenyl)ethyl , 1-(2-chlorophenyl)ethyl, benzyl, (4fluorophenyl)methyl, (3-fluorophenyl)methyl, (2-fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3,5difluorophenyl)methyl, (2, 5-difluorophenyl)methyl, (2,6-difluorophenyl)methyl, (2,4,5-trifluorophenyl)methyl,

- 10 042986 (2,4,6-trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3-chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl , (2,5-dichlorophenyl)methyl, (2,6-dichlorophenyl)methyl, (2,4,5trichlorophenyl)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-5trifluoromethylpyridin-2-yl)methyl, (2-bromo-4-fluorophenyl )methyl, (2-bromo-4-chlorophenyl)methyl, (3-bromo-4fluorophenyl)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, (3-fluoro-4-bromophenyl)methyl, (3chloro-4-bromophenyl)methyl, (2 -chloro-4-fluorophenyl)methyl, (3-chloro-4-fluorophenyl)methyl, (2-fluoro-3chlorophenyl)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, 3-trifluoromethyl-4-chlorophenyl, 3-chloro-4-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5-difluoropyridin-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, (4methylphenyl)methyl, (3-methylphenyl)methyl, (2-methylphenyl)methyl, (4-cyanophenyl)methyl, (3cyanophenyl)methyl, (2-cyanophenyl)methyl, (2,4-diethylphenyl)methyl, ( 3,5-diethylphenyl)methyl, (3,4dimethylphenyl)methyl, (3,5-dimethoxyphenyl)methyl, 1-phenylethyl-1-yl, 1-(o-chlorophenyl)eth-1-yl, 1,3-thiazole -2yl, 4-methyl-1,3-thiazol-2-yl, 1,3-thiazol-2-yl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, n-propylthiomethyl, isopropylthiomethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl , n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, methyl(ethyl)aminocarbonyl, cyclo propylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, allylaminocarbonyl, benzylaminocarbonyl , tert-Butyloxycarbonylaminocarbonyl, hydroxycarbonylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, nbutyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, allyloxycarbonylmethyl, benzyloxycarbonylmethyl, aminocarbonylmethyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, npropylaminocarbonylmethyl, isopropylaminocarbonylmethyl, dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, methyl(ethyl)aminocarbonylmethyl, cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl , cyclopentilaminocarbonethyl, cycloglogslaminocylaminocarbonetil, allylaminocarbonethyl meters, gaslaminocarbonomethyl, aminomethyl, 2-aminoet-1-il, 1-aminoet-1-il, 1 aminoprop-1-il, 3-aminoprop-1-il, metlaminomethylominomethyl, dietlaminominominomal, ethylaminomethyl, isop Pilaminometed , cyclopropylaminomethyl, cyclobutylaminomethyl, cyclopentylaminomethyl, cyclohexylaminomethyl, methoxycarbonylaminomethyl, ethoxycarbonylaminomethyl, tert-butyloxycarbonylaminomethyl, 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 ⁷ and R ⁸ together with the carbon atom to which they are bonded form a double bond, optionally substituted with R ²² and R ²³ according to formula (I'') below wherein m is 0, n is 0, 1, 2 , 3, 4, 5, 6,

R ²¹ is fluorine,

R ²² and R ²³ independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1- methylbutyl, 2methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, ethenyl, 1-propenyl, 1-methylethenyl, 1-butenyl, phenyl, or

R ²² and R ²³ together with the carbon atom to which they are attached form a 3-10 membered monocyclic or bicyclic ring which is saturated and Q is one of the Q-1-Q-345 moieties below:

- 11 042986

______ _X °x/x _o z\ ^ο^/χθ^ X'°^^oDx Q-l Q-2 Q-3 Q-4 Q-5

_o___-\ _η /\ζχ X / ^Ο ^Χ _ο Χχ^ .0___^χ Ρχ^Χ XU Q-6 Q-7 Q-8 Q-9 Q-10

,0^,,/χΛ LIx/<ci ^θ^^χο^χ^ ^°^°ΑζΧ _Β 0.___ x) Q-ll Q-12 Q-13 Q-14 Q-15

Cl 0___ _n /X\ L1 ^^Cl ^0-x ₀ /\^ ^{F z} °^X _a /Ο^/χ,/X. XI _F Q-16 Q-17 Q-18 Q-19 Q-20

Cl /O^r/X^c and ^0___>s _o /\/ ^o x/ _X x^O^y Q-21 Q-22 Q-23 Q-24 Q-25

^o^x^o^x ^0—^oA Q-26 Q-27 Q-28 Q-29 Q-30

^Ox/Xg”^ z"^ ₀ Q-31 Q-32 Q-33 Q-34 Q-3 5

*Xq'—'— ^x sA Q-36 Q-37 Q-3 8 Q-3 9 Q-40

/θχ/ΧΟ^ ⁵ ^o^^x^cr ⁰ ^ Q-41 Q-42 Q-43 Q-44 Q-45

^°x>^s^ ^CF3 ^X/Xg ^ ⁵ ^o^^s ^CF ' 'X _O ^^^S^X|^ ^F Q-46 Q-47 Q-48 Q-49 Q-50

^OxUxq-^ χ°χχ^ο^ /°y^ Q-51 Q-52 Q-53 Q-54 Q-55

^o^x^cr' o^2^o^x Q-56 Q-57 Q-58 Q-59 Q-60

'XqUx/Xo^ ---U _Q / ^o^x^o^ Q-61 Q-62 Q-63 Q-64 Q-65

^ο-^^χ'θχ M—----°'^x _o x Q-66 Q-67 Q-68 Q-69 Q-70

/X χ°χΧ° _xo ^C° /°xX /°xX° Q-71 Q-72 Q-73 Q-74 Q-75

_X °xx / ⁰ ^ ⁰ _x oX^ /°yQ /°уС° Q-76 Q-77 Q-78 Q-79 Q-80

/°xX X°xxC ^S ,°xX} ^S=O X Q-81 Q-82 Q-83 Q-84 Q-85

- 12 042986

- 13 042986

Q-156 Q-157 Q-158 Q-159 Q-160

H H H F Q-161 Q-162 Q-163 Q-164 Q-165

HCl H F H F H F Q-166 Q-167 Q-168 Q-169 Q-170

^A^ H H _z / ^N X^O-'^% Q-171 Q-172 Q-173 Q-174 Q-175

H H Xn^^o^z Q-176 Q-177 Q-178 Q-179 Q-180

H H H /Ά^Χ/ H I ^zA-^zA H Q-181 Q-182 Q-183 Q-184 Q-185

H H A% Q-186 Q-187 Q-188 Q-189 Q-190

H X^o'^ ³ H χ ¹ ^^' ^n^^o ^CF3 H ^N^X^t/^ ⁵ H h Q-191 Q-192 Q-193 Q-194 Q-195

H H ^n^x ^Z4 s' ^CF3 A^'χ^-' ^{02 '35} H H H

Q-196 Q-197 Q-198 Q-199 Q-200

“^0 zA. ^H \/ Q-201 Q-202 Q-203 Q-204 Q-205

^x fxt h I Q-206 Q-207 Q-208 Q-209 Q-210

H H --- H H h^ ⁴ ^ ⁴ Q-211 Q-212 Q-213 Q-214 Q-215

H H Xj^^zx^q^^JO H Q-216 Q-217 Q-218 Q-219 Q-220

H r—\ X ^N Xz^O ^H Γ^λ N >0° h rA NX° H χ ^Ν χ/^0 ^? Η i--- N xxy° Q-221 Q-222 Q-223 Q-224 Q-225

h ch N Jx^° h N>L/° and rf X ^N XzA(/ ^H GL N >^° Q-226 Q-227 Q-228 Q-229 Q-230

hi-y X ^N XzA _s ^ h ⁿ GA H r—\ NA ^S=O h i--to X ^N xX^s; o'° Q-231 Q-232 Q-233 Q-234 Q-235

- 14 042986

ⁿ ch R N 1 st χ^χ/*^ 'o n Άλ. al) n Άλ ν >χ/° AND Q-236 Q-237 Q-238 Q-239 Q-240

Η Η Η Η Q-241 Q-242 Q-243 Q-244 Q-245

^Η ιΆ ^Η ίΆ Η χΝχ/LA Ή Q-246 Q-247 Q-248 Q-249 Q-250

Η Η Η Q-251 Q-252 Q-253 Q-254 Q-255

n ίΆ And h H ^s n P's Q-256 Q-257 Q-258 Q-259 Q-260

L0 0 ^H ιΆ >χΛ,% 'xXT° 'Tf° H Ά?ο Q-261 Q-262 Q-263 Q-264 Q-265

η / ^Ν \/χ o ^{0 H} /^x/^ ^s r ^ox o O ^χχθ'° o ΐί^χΟ ⁸ ^ ⁰ H AZ's Q-266 Q-267 Q-268 Q-269 Q-270

H H ✓ Νχ^-χ 1---01 H H 'o H Q-271 Q-272 Q-273 Q-274 Q-275

H H Ιχ^Ο H H χΝχχχ/ \/° H A. Q-276 Q-277 Q-278 Q-279 Q-280

H H H H H Ν^^χχ χ^χχχ/ \/S Q-281 Q-282 Q-283 Q-284 Q-285

H V 0 H ^x XX H ^x XX H ^x XX H ^¢) Q-286 Q-287 Q-288 Q-289 Q-290

H H H H χ ^Ν χχ( J 'X^ XX=° xx° x^° ^(3 ο' Ό o '0 '0 Q-291 Q-292 Q-293 Q-294 Q-295

H H H H H Q-296 Q-297 Q-298 Q-299 Q-300

Q-301 Q-302 Q-303 Q-304 Q-305

- 15 042986

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

R ¹ is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 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, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, methoxy-n-propyl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4fluorophenyl, 2,4-difluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5dichlorophenyl, 3,4-dichlorophenyl, 3,5- dichlorophenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiophen-2yl, thiophen-3-yl, furan-2-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, phenylethyl, 1-(4-methylphenyl)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, (2fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3,5-difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2 ,6difluorophenyl)methyl, (4-chlorophenyl)methyl, (3-chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl, (2,5-dichlorophenyl)methyl , methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, n-propylthiomethyl, 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 to 10-membered monocyclic or bicyclic ring, or

R ⁵ and R ⁶ together with the carbon atom to which they are bonded form a double bond, optionally substituted with R ²² and R ²³ according to formula (I') below

R ⁷ and R ⁸ 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, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl- 3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1- methyl-2pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, 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, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3, 5-difluorophenyl, 2,4,5trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5dichlorophenyl, 2,6-dichlorophenyl, 2,3- dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, pyridin-2-yl, pyridin-3-yl, 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-(3-chlorophenyl)ethyl, 1-(2chlorophenyl)ethyl, benzyl, (4-fluorophenyl)methyl, (3-fluorophenyl) methyl, (2-fluorophenyl)methyl, (2,4difluorophenyl)methyl, (3,5-difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6-difluorophenyl)methyl, (2,4,5trifluorophenyl) methyl, (2,4,6-trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3-chlorophenyl)methyl, (2chlorophenyl)methyl, (2,4-dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl, (2,5-dichlorophenyl)methyl, (2,6dichlorophenyl)methyl, (2,4,5-trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, n-propylthiomethyl, isopropylthiomethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, 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 ⁷ and R ⁸ together with the carbon atom to which they are bonded form a double bond, optionally substituted with R ²² and R ²³ according to formula (I'') below

in which m is 0, n is 0, 1, 2, 3,

R ²¹ is fluorine,

R ²² and R ²³ independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1- methylbutyl, 2methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, ethenyl, 1-propenyl, 1-methylethenyl, 1-butenyl, phenyl, or

R ²² and R ²³ together with the carbon atom to which they are attached form a 3 to 10 membered monocyclic or bicyclic ring which is saturated and Q is one of the Q-1-Q-345 moieties indicated higher.

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

R ¹ is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,

R ² is hydrogen, methyl, ethyl,

R ³ is fluorine, chlorine, bromine,

R ⁴ is fluorine, chlorine, bromine,

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, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, npropyloxyethyl, methoxy-n-propyl, phenyl, pyridine-2- yl, pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, furan-2-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, phenylethyl, benzyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, n-propylthiomethyl, 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 to 10-membered monocyclic or bicyclic ring, or

R ⁵ and R ⁶ together with the carbon atom to which they are bonded form a double bond, optionally substituted with R ²² and R ²³ according to formula (I') below

R ⁷ and R ⁸ 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, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl- 3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1- methyl-2pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 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-propyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, methoxy-npropyl, pyridine- 2-yl, pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, furan-2-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, benzyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, npropylthiomethyl, isopropylthiomethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, 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 ⁷ and R ⁸ together with the carbon atom to which they are bonded form a double bond, optionally substituted with R ²² and R ²³ according to formula (I'') below

- 18 042986

in which m is 0, n is 0, 1, 2, 3,

R ²¹ is fluorine,

R ²² and R ²³ independently represent hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 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, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, ethenyl, 1-propenyl, 1-methylethenyl, 1-butenyl, phenyl, or

R ²² and R ²³ together with the carbon atom to which they are attached form a 3-10 membered monocyclic or bicyclic ring which is saturated and Q is one of the following moieties: Q-1, Q-2, Q-3 , Q-6, Q-7, Q-8, Q-10, Q-11, Q-18, Q-23, Q-24, Q-26, Q-27, Q-28, Q-30, Q -31, Q-32, Q-36, Q-41, Q-42, Q-46, Q-48, Q-51, Q-52, Q-71, Q-72, Q-73, Q-74 , Q-79, Q-80, Q-81, Q-82, Q89, Q-91, Q-92, Q-93, Q-94, Q-95, Q-106, Q-108, Q-115 , Q-117, Q-118, Q-121, Q-123, Q-126, Q-127, Q-132, Q-142, Q-151, Q-152, Q-153, Q-156, Q -157, Q-158, Q-176, Q-177, Q-180, Q-181, Q-216, Q-221, Q-224, Q-229, Q-239, Q-241, Q-242 , Q-243, Q-271, Q-273, Q-275, Q-276, Q-277, Q-285, Q-301, Q-302, Q-308, Q-311, Q-312, Q -331, Q-333, Q-334, Q-335, Q-336, Q-340, Q-341.

The definitions of the above radicals, given in general terms or listed in the preferred aspects, apply both to the final 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 in the form of combinations between these preferred ranges.

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

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, the 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, 1,3-dimethylbutylsulfonyl, 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 )-, (Ci -C ₆ )- or (C 1 -C ₄ )alkylthio, for example (but not limited to) (C 1 -C ₆ )alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1.1 -dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3 -methylpentylthio, 4-methylpentylthio, 1,1dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1 ,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio.

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 (without limitation) (Cr C ₆ )alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1 ,1dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2methylpentylsulfinyl, 3-methylpentylsulfinyl inyl, 4-methylpentylsulfinyl . ,2trimethylpropylsulfinyl, 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 )-, (C ₃ -C ₆ )- or (C ₃ C ₄ )alkynylsulfinyl.

- 20 042986

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 )-, (C ₃ -C ₆ )- or (C ₃ C ₄ )alkynylsulfonyl.

Alkoxy means an alkyl radical linked via an oxygen atom, for example (but not limited to) (C1-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, for example (C ₂ -C ₁₀ )-, (C ₂ -C ₆ )- or (C ₂ -C ₄ )alkenyloxy or (C ₃ -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-C ₁₀ ) -, (C ₁ -C ₆ )- or (C 1 -C ₄ )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 are alkenyl and alkynyl radicals linked to the backbone via -C(=O)-, for example (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-C ₁₀ )- , (Ci-C ₆ )- or (C1C ₄ )alkoxycarbonyl. The number of carbon atoms refers in this case to the alkyl radical in the alkoxycarbonyl group. Similarly, alkenyloxycarbonyl and alkynyloxycarbonyl, unless otherwise defined elsewhere, in accordance with the present invention are alkenyl and alkynyl radicals linked to the backbone via -O-C(=O)-, for example (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-C ₁₀ )-, (C1-C ₆ )- 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 , alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bisalkylaminoalkoxy, tris-[alkyl]silyl, bis-[alkyl]arylsilyl, bis-[alkyl]alkylsilyl, tris- 21 042986

[alkyl]silylalkynyl, arylalkynyl, heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bisalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl , cycloalkylaminocarbonyl, bisalkylaminocarbonyl, heteroarylalkoxy, arylalkoxy.

The heterocyclic radical (heterocyclyl) 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 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-1H-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-dihydropyridin-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; 4,5dihydro-1H-pyrazol-1-, or 3-, or 4-, or 5-yl; 2,3-dihydro-1H-pyrazole-1-, or 2-, or 3-, or 4-, or 5yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazol-1-, or 2-, or 3-, or 4-yl; 2,5dihydro-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-dihydropyrazin-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;

- 22 042986

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; 1,2dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidin-2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or 6-yl; 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1-, or 2-, or 3-piperazinyl; 1,2,3,6-tetrahydropyrazin-1-, or 2-, or 3-, or 5-, or 6-yl; 1,2,3,4-tetrahydropyrazin-1-, or 2-, or 3-, or 4-, or 5-, or 6-yl; 1,2-dihydropyrazin-1-, or 2-, or 3-, or 5-, or 6-yl; 1,4-dihydropyrazin-1- or 2- or 3-yl; 2,3-dihydropyrazin-2-, or 3-, or 5-, or 6-yl; 2,5-dihydropyrazin-2- or 3-yl; 1,3-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 4yl; 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-dithiin3- or 4-yl; 1,3-dithian-2- or 4- or 5-yl; 4H-1,3-dithiin-2-, or 4-, or 5-, or 6-yl; isoxazolidin-2-, or 3-, or 4-, or 5-yl; 2,3-dihydroisoxazol-2-, or 3-, or 4-, or 5-yl; 2,5-dihydroisoxazol-2-, or 3-, or 4-, or 5-yl; 4,5-dihydroisoxazol-3- or 4- or 5-yl; 1,3-oxazolidin-2-, or 3-, or 4-, or 5yl; 2,3-dihydro-1,3-oxazol-2-, or 3-, or 4-, or 5-yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5dihydro-1,3-oxazol-2- or 4- or 5-yl; 1,2-oxazinan-2-, or 3-, or 4-, or 5-, or 6-yl; 3,4-dihydro2H-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-1,3oxazin-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-dihydro2H-1,4-oxazin-2-, or 3-, or 4-, or 5-, or 6-yl; 3,6-dihydro-2H-1,4-oxazine-2-, or 3-, or 5-, or 6yl; 2H-1,4-oxazin-2-, or 3-, or 5-, or 6-yl; 4H-1,4-oxazin-2- or 3-yl; 1,2-oxazepan-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,4,5-tetrahydro-1,2-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,4,7-tetrahydro-1,2-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,6,7-tetrahydro-1,2oxazepin-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-dihydro1,2-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,5-dihydro-1,2-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,7-dihydro-1,2-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 4,5-dihydro1,2-oxazepin-3-, or 4-, or 5-, or 6-, or 7-yl; 4,7-dihydro-1,2-oxazepin-3-, or 4-, or 5-, or 6-, or 7-yl; 6,7-dihydro-1,2-oxazepin-3-, or 4-, or 5-, or 6-, or 7-yl; 1,2-oxazepin-3-, or 4-, or 5-, or 6-, or 7-yl; 1,3-oxazepan-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,4,5-tetrahydro-1,3-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,4,7-tetrahydro-1,3-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,6,7-tetrahydro-1,3-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,5,6,7-tetrahydro1,3-oxazepin-2-, or 4-, or 5-, or 6-, or 7-yl; 4,5,6,7-tetrahydro-1,3-oxazepin-2-, or 4-, or 5-, or 6-, or 7-yl; 2,3-dihydro-1,3-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,5-dihydro-1,3oxazepin-2-, or 4-, or 5-, or 6-, or 7-yl; 2,7-dihydro-1,3-oxazepin-2-, or 4-, or 5-, or 6-, or 7yl; 4,5-dihydro-1,3-oxazepin-2-, or 4-, or 5-, or 6-, or 7-yl; 4,7-dihydro-1,3-oxazepin-2-, or 4-, or 5-, or 6-, or 7-yl; 6,7-dihydro-1,3-oxazepin-2-, or 4-, or 5-, or 6-, or 7-yl; 1,3-oxazepin-2-, or 4-, or 5-, or 6-, or 7-yl; 1,4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,4,7-tetrahydro-1,4-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3,6,7-tetrahydro-1,4-oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 2,5,6,7tetrahydro-1,4-oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 4,5,6,7-tetrahydro-1,4-oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 2,3-dihydro-1,4-oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 2,5dihydro-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-1,4oxazepin-2-, or 3-, or 4-, or 5-, or 6-, or 7-yl; 6,7-dihydro-1,4-oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 1,4-oxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; isothiazolidin-2-, or 3-, or 4-, or 5-yl; 2,3-dihydroisothiazol-2-, or 3-, or 4-, or 5-yl; 2,5-dihydroisothiazol-2-, or 3-, or 4-, or 5-yl; 4,5-dihydroisothiazol-3- or 4- or 5-yl; 1,3-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; 3,4-dihydro-2H-1,3-thiazin-2-, or 3-, or 4-, or 5-, or 6-yl; 3,6-dihydro-2H-1,3-thiazin-2-, or 3-, or 4-, or 5-, or 6-yl; 5,6-dihydro-2H1,3-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-1,3thiazin-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 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

- 23 042986 dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2dioxazin-3-, or 5-, or 6-yl; 1,4,2-dioxazepan-2-, or 3-, or 5-, or 6-, or 7-yl; 6,7-dihydro-5H1,4,2-dioxazepin-3-, or 5-, or 6-, or 7-yl; 2,3-dihydro-7H-1,4,2-dioxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 2,3-dihydro-5H-1,4,2-dioxazepin-2-, or 3-, or 5-, or 6-, or 7-yl; 5H-1,4,2-dioxazepin3-, 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.

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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 then means, for example, a carbonyl group in a heterocyclic ring. As a result, lactones and lactams are preferably also covered. An oxo group may also be present at ring heteroatoms which may exist in different oxidation states, such as in the case of N and S, and in such a case form 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 means heteroaromatic compounds, i.e. fully unsaturated aromatic heterocyclic compounds, preferably 5-7-membered rings containing 1-4, preferably 1 or 2, identical or different heteroatoms, preferably O, S or N. The heteroaryls according to the invention are, for example, N-pyrrole -1-yl; SH-pyrrol-2-yl; SH-pyrrol-3-yl; furan-2-yl; furan-3

- 25 042986 silt; thien-2-yl; thien-3-yl, 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H- 1,2,3-triazol-2-yl, 2Н-1,2,3-triazol-4-yl, 1H-1,2,4-truαzol-1yl, 1Н-1,2,4-triazol-3- yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, azepinyl, pyridin2-yl, pyridin-3-yl, pyridin- 4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1.3, 5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,3- triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3 -yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol -4-yl, isothiazol-5-yl, 1,3-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, 1,2,3,4oxatriazole -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 carbon atoms are part of an additional aromatic ring, this results in the formation of fused heteroaromatic systems, such as benzofused or polyfused heteroaromatic substances. Preferred examples are quinolines (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl) ; isoquinolines (eg, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; pyridopyrazines; pyridopyrimidines; pyridopyridazines; pteridines; pyrimidopyrimidines. Examples of heteroaryl are also 5- or 6-membered benzo-fused rings from the group consisting of 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3yl, 1H-indol-4-yl, 1H-indol-5 -yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1 -benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6 -yl, 1-benzothiophen-7-yl, 1Hindazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H -indazol-7-yl, 2H-indazol-2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazole -7-yl, 2H-isoindol-2-yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2Nisoindol-6-yl ; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H- benzimidazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol- 7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol- 7-yl, 1,2-benzisoxazol-3yl, 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 respectively mean alkyl, alkenyl and alkynyl, partially or completely substituted by 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, eg CCl ₃ , CClF ₂ , CFCl ₂ , CF ₂ CClF ₂ , CF ₂ CClFCF ₃ ; polyhaloalkyl, eg CH ₂ CHFCl, CF ₂ CClFH, CF ₂ CBrFH, 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. CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3.

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.

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Haloalkoxy is, for example, OCF ₃ , OCHF2, OCH2F, OCF2CF3, OCH2CF3 and

OCH2CH2C1; 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 specified carbon atom range, i.e. includes radicals representing methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-butylpropyl or tert-butyl. Alkyl radicals in general form containing a greater range of carbon atoms, for example (C ₁ 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, 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 be optionally 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, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4- pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2methyl-2-butenyl, 3-methyl-2-butenyl, 1- methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3- methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3- pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4- methyl-4-pentenyl, 1,1dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl3- butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1- ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl2-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. (C2-C6) alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3 -pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl2-propynyl, 1-ethyl -2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl -3-pentynyl, 2-methyl-4-pentynyl, 3-methyl1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2 -butynyl, 1,1dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2butynyl, 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 are also included, e.g. bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, -yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2 .1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl and adamantan-2-yl, but also systems such as, for example, 1,1'-bi(cyclopropyl)-1-yl, 1,1'-bi(cyclopropyl)-2-yl. The expression (C ₃ 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 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 explanations for a substituted cycloalkyl apply 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 means 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 is a heteroaryl radical linked via an alkyl group, and heterocyclylalkyl is 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.

According to 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 (Ci-C ₈ )-, (C1 -C ₆ )- or (C 1 -C ₄ ) haloalkylthio, for example (without limitation), trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3.3, 3-prop-1-ylthio.

Halocycloalkyl and halocycloalkenyl means cycloalkyl or cycloalkenyl partially or completely 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-1

- 28 042986 yl, 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 )-, (6 ₁ -6 ₆ )- or (C ₁ -C ₄ )alkyl]silyl, for example (without limitation), trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, tri(isopropyl)silyl, tri(n-butyl) silyl, tri(1-methylprop-1-yl)silyl, tri(2-methylprop-1-yl)silyl, tri(1,1-dimethylethyl-1-yl)silyl, tri(2,2-dimethyleth-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. Fragments Q, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ²¹ in the general formula (I) in the schemes below have the meanings defined above, but only if illustrative are given, not restrictive definitions. The first key intermediate obtained for the synthesis of compounds of general formula (I) in accordance with the present invention is an optionally further 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 (e.g. sodium hydride or potassium t-butoxide) in a suitable polar aprotic solvent (e.g. N,K-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-1Hpyrimidine-2, 4-dione, by way of example and not limitation, 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl6-trifluoromethyl-1H-pyrimidine-2,4-dione (IIa) (see KR1345394 ; EP1122244; EP408382; WO2003/029226; WO2010/038953; US2011/0224083; KR2011/110420). In Scheme 1 below, R ¹ 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 in by way of example, and not limitation, is chlorine, and R ²¹ by way of example, and not limitation, is fluorine.

Scheme 1

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 ²¹ by way of example, and not limitation, is fluorine.

- 29 042986

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-2,4dione (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 NH ₂ , R ² by way of example and not limitation is hydrogen, R ³ by way of example and not limitation is fluorine, R ⁴ in by way of example, and not limitation, is chlorine, and R ²¹ by way of example, and not limitation, is fluorine.

Scheme 3

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 carrying out reaction with a suitable, optionally further substituted 2-haloalkylcarboxylate (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, optional additionally substituted 2-haloalkanocarboxylic acid to give the corresponding thioalkanocarboxylic acid intermediate (IV) using an appropriate base (e.g. potassium carbonate, cesium carbonate) and then reacting the corresponding intermediate (IV) with a suitable optionally further substituted hydroxyalkyl ether or hydroxyalkyl thioether using suitable coupling reagents (e.g. HOBt=1hydroxybenzotriazole, EDC=1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, HATU=O-(7azabenzotriazol-1-yl)-N,N,N ',N'-tetramethyluronium hexafluorophosphate, T3P = 2,4,6-tripropyl-1,3,5,2,4,6trioxatriphosphorinan-2,4,6-trioxide) and suitable bases (e.g. diisopropylethylamine, triethylamine) in an appropriate polar aprotic solvent (eg dichloromethane, chloroform). In Scheme 4 below, R ² and R ⁶ by way of example and not limitation are hydrogen, R ²¹ by way of example and not limitation is fluorine, n and m by way of example and not limitation are 0, and Q by way of example, and not limitation, is fragments Q-21 and Q-26.

Scheme 4

Selected detailed synthesis examples for compounds of general formula (I) according to the present invention are given below. The specified numbers of examples correspond to the numbering given in table. I.1-I.60 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 , CD ₃ OD 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,

- 30 042986 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 CH3, Et \u003d CH2CH3, t-Hex \u003d C (CH3) ₂ CH (CH3) ₂ , t-Bu \u003d C (CH3) 3, n-Bu \u003d straight butyl, nPr = straight propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl.

Synthesis Examples No. I.2-72. Tetrahydrofuran-3-ylmethyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)3,6-dihydropyrimidin-1(2H)-yl]phenyl }sulfanyl)butanoate

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. 2-Fluoro-4-chlorophenylisocyanate 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)-3amino-4,4,4-trifluorobut-2-enoate (14.2 g, 77.5 mmol) was added. The reaction mixture was stirred at room temperature for 1 h, 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 1N. 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)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (15.2 g, 50.2 mmol, 65%) was obtained, which was used on 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-2fluorophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (238 g, 770 mmol) in abs. N,Ndimethylformamide (800 ml) was added potassium carbonate (117 g, 850 mmol). After that, a solution of methyl iodide (120 g, 850 mmol) in abs. N,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( 1 H,3H)-dione (241 g, 747 mmol, 97% of theoretical) was obtained, which was converted in the next step without further purification. 3-(4-Chloro-2-fluorophenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4( 1 H,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 2chloro-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)pyrimidine-2,4(1H,3H)-dione (73.0 g, 206 mmol, 83% of theory) as a colorless solid. 2-Chlorobutanecarboxylic 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-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 a temperature of 50° C. for 1 hour and, after cooling to room temperature, mixed with water and

- 31 042986 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- dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoic acid (2.0 g, 80% of theory) as a colorless solid. ¹ H-NMR (CDCU 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 ( 90 mg, 0.20 mmol), 1-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, tetrahydro-3-furanmethanol (27 mg, 0.28 mmol) and triethylamine (0.04 ml, 0.27 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 tetrahydrofuran-3-ylmethyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl )-3,6dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoate (83 mg, 77% of theory) as a high viscosity colorless oil. ¹ H-NMR (CDCl ₃ δ, ppm) 7.47 (m, 1H), 7.37 (d, 1H), 6.35 (d, 1H), 4.13-3.89 (m, 2H) , 3.83-3.67(m, 4H), 3.55(s, 3H), 3.47-3.43(m, 1H), 2.53-2.40(m, 1H), 2 .02-1.90 (m, 2H), 1.89-1.79 (m, 1H), 1.59-1.49 (m, 1H), 1.07 (t, 3H).

No. I.2-91. Tetrahydro-2H-pyran-2-ylmethyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H )-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 (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, 2-(hydroxymethyl)tetrahydropyran (34 mg, 0.29 mmol) and triethylamine (0.04 ml, 0.29 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 tetrahydro-2H-pyran-2-ylmethyl-2({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4 -(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoate (38 mg, 31% of theory) as a high viscosity colorless oil. ¹ H-NMR (CDCl ₃ δ, ppm) 7.53 (m, 1H), 7.35 (m, 1H), 6.35 (m, 1H), 4.12-3.88 (m, 3H) , 3.76-3.71(m, 1H), 3.55(s, 3H), 3.47-3.32(m, 2H), 2.03-1.92(m, 1H), 1 .89-1.78 (m, 2H), 1.62-1.42 (m, 5H), 1.08 (t, 3H).

No. I.2-92. Tetrahydro-2H-pyran-3-ylmethyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4(trifluoromethyl)-3,6-dihydropyrimidin-1 (2H) -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 (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, 3-(hydroxymethyl)tetrahydropyran (34 mg, 0.29 mmol) and triethylamine (0.04 ml, 0.29 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 tetrahydro-2H-pyran-3-ylmethyl-2-({2-chloro-4fluoro-5-[3-methyl-2,6-dioxo-4- (trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoate (25 mg, 20% of theory) as a high viscosity colorless oil. 1H-NMR (CDCl ₃ δ, ppm) 7.52 (m, 1H), 7.37 (m, 1H), 6.35 (m, 1H), 4.03-3.97 (m, 1H), 3.96-3.87 (m, 1H), 3.85-3.77 (m, 1H), 3.723.68 (m, 1H), 3.55 (s, 3H), 3.41-3, 34 (m, 1H), 3.17-3.10 (m, 1H), 2.03-1.92 (m, 1H), 1.89-1.78 (m, 2H), 1.62- 32 042986

1.42 (m, 5H), 1.08 (t, 3H).

No. I.4-91. Tetrahydro-2H-pyran-2-ylmethyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1 (2H )-yl]phenyl}sulfanyl)-4-methylpentanoate

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. 1H-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 (120 mg, 0.26 mmol), 1-hydroxy-1H-benzotriazole (45 mg, 0.33 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (66 mg, 0.33 mmol) were dissolved in abs. dichloromethane in a heated round bottom flask under argon and, after stirring at room temperature for 5 minutes, 2-(hydroxymethyl)tetrahydropyran (39 mg, 0.33 mmol) and triethylamine (0.05 ml, 0.33 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 tetrahydro-2H-pyran-2-ylmethyl-2-({2-chloro-4-fluoro-5-[3-methyl-2,6dioxo-4- (trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-4-methylpentanoate (81 mg, 56% of theory) as a high viscosity colorless oil. ¹ H-NMR (CDCl ₃ δ, ppm) 7.53 (m, 1H), 7.35 (m, 1H), 6.35 (d, 1H), 4.08-3.98 (m, 1H) , 3.94-3.84 (m, 3H), 3.55 (s, 3H), 3.48-3.33 (m, 2H), 1.90-1.76 (m, 3H) 1, 71-1.63 (m, 1H), 1.57-1.43 (m, 5H), 1.28-1.17 (m, 1H), 0.96-0.93 (m, 6H), 0.90-0.84 (m, 1H).

No. I.6-221. 2-({2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin1(2H)-yl]phenyl}sulfanyl)-3-methyl -N-(tetrahydrofuran-2-ylmethyl)butanamide

2-Chloro-3-methylbutanecarboxylic acid (770 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)-3-methylbutanoic acid (0.47 g, 21% of theory) as a colorless solid. 1H-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), 2.25-2.17 (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 (100 mg, 0.22 mmol), 1hydroxy-1H-benzotriazole (39 mg, 0.29 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (65 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, 2(aminomethyl)tetrahydrofuran (29 mg, 0.29 mmol) and triethylamine (0.04 ml, 0.29 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) and

- 33 042986 received 2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl} sulfanyl)-3-methyl-N-(tetrahydrofuran-2-ylmethyl)butanamide (44 mg, 37% of theory) as a high viscosity colorless oil. SH-NMR (CDCl ₃ δ, ppm) 7.36 (m, 1H), 7.28 (m, 1H), 6.91-6.81 (m,

1H, NH), 6.34 (m, 1H), 3.90-3.61 (m, 3H), 3.58-3.56 (m, 1H), 3.54 (s, 3H), 3 .50-3.42 (m, 1H), 3.20-3.06 (m,

1H), 2.42-2.33 (m, 1H), 1.92-1.68 (m, 3H), 1.48-1.42/1.33-1.28 (m, 1H), 1.15 (d, 3H), 1.11 (d, 3H).

No. I.12-72. Tetrahydrofuran-3-ylmethyl-2-({2-chloro-4-fluoro-5-[3,5-dimethyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)- yl]phenyl}sulfanyl)butanoate

A solution of n-butyl lithium in hexane (2.5 M, 240 ml) was added to a solution of diisopropylamine (61.0 g, 603 mmol) cooled to -10°C in abs. tetrahydrofuran (300 ml). The resulting reaction mixture was stirred at a temperature of -10°C for 30 min and then cooled further to -78°C. This was followed by careful addition of ethyl propionate (51.0 g, 499 mmol). The reaction mixture was stirred at -78° C. for 1 h, 2,2,2-trifluoroethyl trifluoroacetate (147 g, 750 mmol) 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 thus obtained ethyl 4,4,4-trifluoro-2-methyl-3-oxobutanoate (62.0 g, 63% of theory) as a portion (49.5 g, 250 mmol) was dissolved without further purification in toluene (400 ml) in a round bottom flask and mixed with ammonium acetate (96.0 g, 1245 mmol) and acetic acid (15 ml). 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-(2Z)-3-amino-4,4,4-trifluoro-2-methylbut-2-enoate (31.0 g, 62% of theory). 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 resulting 2-fluoro-4-chlorophenylisocyanate 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-(2Z)-3-amino4,4,4-trifluoro-2-methylbut-2-enoate (14.2 g, 72.1 mmol) was added. The reaction mixture was stirred at room temperature for 1 h, 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 1N. 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-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)dione (15.5 g, 48.1 mmol, 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)pyrimidine-2,4(1H,3H)-dione (23.8 g, 73.8 mmol) in abs. N,N-dimethylformamide (80 ml) was added potassium carbonate (11.7 g, 84.7 mmol). After that, a solution of methyl iodide (12.0 g, 84.5 mmol) in abs. N,N-dimethylformamide (10 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 (200 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. 3-(4-Chloro-2-fluorophenyl)-1,5-dimethyl-6-(trifluoromethyl)pyrimidine-2,4(III,3H)-dione (24.1 g, 71.6 mmol, 97 % of theory), which was converted in the next step without further purification. 3-(4-Chloro-2-fluorophenyl)-1,5-dimethyl-6(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (10.0 g, 29.7 mmol) was then gradually added to the chlorosulfonic acid (200 ml) 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).

- 34 042986

The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. This provided 2-chloro-4-fluoro-5-[3,5-dimethyl-2,6-dioxo-4(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]benzenesulfonyl chloride (7.74 g , 17.8 mmol, 60% 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-[3,5-dimethyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin1(2H)-yl]sulfonyl chloride (10.0 g, 23.0 mmol) in a round bottom flask were added successively hydrochloric acid (50 ml), acetic acid (50 ml) and tin dichloride dihydrate (27.0 g, 120 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)-1,5dimethyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (7.6 g, 20.6 mmol, 89% of theory) as a colorless solid. 2-Chlorobutanecarboxylic acid (332 mg, 2.71 mmol) was dissolved in abs. acetonitrile under argon in a heated round bottom flask and then cesium carbonate (1.77 g, 5.42 mmol) and 3-(4-chloro-2-fluoro-5-sulfanylphenyl)-1,5-dimethyl-6-( trifluoromethyl)pyrimidine 2,4(1H,3H)-dione (1.0 g, 2.71 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-[3,5-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine1( 2H)-yl]-4-fluorophenyl}sulfanyl)butanoic acid (1.42 g, 80% of theory) as a colorless solid. ¹ H-NMR (CDC^ δ, ppm) 7.55 (d, 1H), 7.37 (d, 1H), 3.68 (m, 1H), 3.55 (s, 3H), 2.282.21 (m, 3H), 2.05-1.91 (m, 1H), 1.90-1.78 (m, 1H), 1.10 (t, 3H). 2-({2-Chloro-5-[3,5-dimethyl-2,6-dioxo-4(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-4-fluorophenyl}sulfanyl)butanoic acid (160 mg, 0.35 mmol), 1-hydroxy-1H-benzotriazole (62 mg, 0.46 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (88 mg, 0.46 mmol) were dissolved in abs. dichloromethane in a heated round bottom flask under argon and, after stirring at room temperature for 5 minutes, 3-(hydroxymethyl)tetrahydrofuran (47 mg, 0.46 mmol) and triethylamine (0.12 ml, 0.84 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 tetrahydrofuran-3-ylmethyl-2-({2-chloro-4-fluoro-5-[3,5-dimethyl-2,6-dioxo-4( trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)butanoate (171 mg, 75% of theory) as a high viscosity colorless oil. ¹ H-NMR (CDCl ₃ δ, ppm) 7.47 (m, 1H), 7.37 (d, 1H), 4.133.89 (m, 2H), 3.83-3.67 (m, 4H) , 3.55 (s, 3H), 3.49-3.43 (m, 1H), 2.53-2.44 (m, 1H), 2.26-2.21 (m, 3H), 2.021 .92 (m, 2H), 1.90-1.82 (m, 1H), 1.59-1.49 (m, 1H), 1.07 (t, 3H).

No. I.44-71. Tetrahydrofuran-2-ylmethyl-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl )(cyclopropyl)acetate

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-[3methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine- 1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetate (940 mg, 99% of theory) as a colorless solid. ¹ H-NMR (CDCl ₃ δ, ppm) 7.51 (d, 1H), 7.35 (d, 1H), 6.34 (s, 1H), 4.18-4.05 (m, 2H) , 3.53 (s, 3H), 3.13-3.10 (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)-3,6dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetate (160 mg, 0.33 mmol) was then dissolved in ethyl acetate and 6N 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

- 35 042986 and carefully 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. ¹ H-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), 1.32-1.24 (m, 1H), 0.77-0.69 (m, 2H), 0.52-0.38 (m, 2H). 2-({2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetic acid (120 mg, 0.27 mmol), 1-hydroxy-III-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, 2-(hydroxymethyl)tetrahydrofuran (35 mg, 0.35 mmol) and triethylamine (0.09 ml, 0.64 mmol) was 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 tetrahydrofuran-2-ylmethyl-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4(trifluoromethyl)-3 ,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)(cyclopropyl)acetate (81 mg, 54% of theory) as a high viscosity colorless oil. ¹ H-NMR (d ₆ δ, ppm) 7.83 (d, 1H), 7.72/7.68 (m, 1H), 6.62 (m, 1H), 4.06-3.99 ( m, 1H), 3.97-3.85 (m, 2H), 3.70-3.64 (m, 1H), 3.62-3.56 (m, 1H), 3.48-3, 34 (m, 4H), 1.90-1.68 (m, 3H) 1.53-1.40 (m, 1H), 1.30-1.13 (m, 1H), 0.69-0 .58 (m, 2H), 0.48-0.35 (m, 2H).

No. I.48-82. Tetrahydrothiophen-3-ylmethyl-3-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl] phenyl}sulfanyl)-2,2-dimethylpropanoate

3-Chloropivalic acid (778 mg, 5.64 mmol) was dissolved in abs. acetonitrile (30 mL) under argon in a heated round bottom flask and then potassium carbonate (1.64 g, 11.28 mmol) and 3-(4chloro-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 45° 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 3-({2-chloro-4fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine- 1(2H)-yl]phenyl}sulfanyl)-2,2dimethylpropanoic acid (2.35 g, 87% of theory) as a colorless solid. ¹ HNMR (CDCl3 δ, ppm) 7.49 (d, 1H), 7.37 (d, 1H), 6.39 (s, 1H), 3.57 (s, 3H), 3.02 (s, 2H), 1.29(s, 6H). 3-({2Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-2,2 -dimethylpropanoic acid (200 mg, 0.44 mmol), 1-hydroxy-III-benzotriazole (77 mg, 0.57 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (110 mg, 0.57 mmol ) was dissolved in abs. dichloromethane in a heated round bottom flask under argon and, after stirring at room temperature for 5 minutes, tetrahydrothiophen-3-ylmethanol (68 mg, 0.57 mmol) and triethylamine (0.15 ml, 1.06 mmol) were added. The resulting reaction mixture was stirred at room temperature for 3 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 tetrahydrothiophen-3-ylmethyl-3-({2-chloro-4fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)- 3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-2,2dimethylpropanoate (128 mg, 52% of theory) as a high viscosity colorless oil. ¹ H-NMR (CDCl3 δ, ppm) 7.34 (d, 1H), 7.30 (d, 1H), 6.36 (m, 1H), 4.12-4.08 (m, 1H), 4.06-4.00 (m, 1H), 3.56 (s, 3H), 3.12 (s, 2H), 2.93-2.85 (m, 3H) 2.64-2.58 (m, 1H), 2.56-2.48 (m, 1H), 2.13-2.09 (m, 1H), 1.78-1.69 (m, 1H), 1.32 (s , 6H).

No. I.48-92. Tetrahydro-2H-pyran-3-ylmethyl-3-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H )-yl]phenyl}sulfanyl)-2,2-dimethylpropanoate

3-({2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-2 ,2-dimethylpropanoic acid (200 mg, 0.44 mmol), 1-hydroxy-III-benzotriazole

- 36 042986 (77 mg, 0.57 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (110 mg, 0.57 mmol) were dissolved in abs. dichloromethane in a heated round-bottom flask under argon and, after stirring at room temperature for 5 minutes, tetrahydro-2H-pyran-3-ylmethanol (66 mg, 0.57 mmol) and triethylamine (0.15 ml, 1.06 mmol). The resulting reaction mixture was stirred at room temperature for 3 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 tetrahydro-2H-pyran-3-ylmethyl-3({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4 -(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)-2,2-dimethylpropanoate (149 mg, 61% of theory) as a high viscosity colorless oil. ¹ H-NMR (CDCl3 δ, ppm) 7.34 (d, 1H), 7.31 (m, 1H), 6.36 (m, 1H), 4.02-3.95 (m, 1H), 3.92-3.70 (m, 3H), 3.56 (s, 3H), 3.43-3.37 (m, 1H), 3.27-3.19 (m, 1H), 3. 11 (s, 2H), 1.99-1.91 (m, 1H), 1.84-1.77 (m, 1H), 1.66-1.59 (m, 2H), 1.33- 1.27 (m, 1H), 1.31 (s, 6H).

No. I.60-71. Tetrahydrofuran-2-ylmethyl-2-({2-chloro-5-[5-ethyl-3-methyl-2,6-dioxo-4-(trifluoromethyl)3,6-dihydropyrimidin-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-3-oxobutanoate thus obtained (67% of theory) was dissolved without further purification in toluene in a round-bottomed flask 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-amino4,4,4-trifluoro-2-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 completion of the addition, 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. 2-Fluoro-4-chlorophenylisocyanate was used in the next step without further purification. Sodium hydride (60% dispersion in mineral oil) was suspended in abs. N,N-dimethylformamide and ethyl-(22)-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 1N. 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-dimethylformamide. After that, a solution of methyl iodide (1.2 eq.) was added in abs. N,N-dimethylformamide 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 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)pyrimidine-2,4(1H,3H)-dione (97% of theory) was obtained, which was converted to next step without further purification. 3-(4Chloro-2-fluorophenyl)-5-ethyl-1-methyl-6-(trifluoromethyl)pyrimidine-2,4( 1 H,3H)-dione then gradually to

- 37 042986 was 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-fluoro-5-[5-ethyl-3-methyl-2,6-dioxo-4(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]benzenesulfonyl chloride (54% theoretical), which was used in the next step without further purification. To the initial load in the form of 2chloro-4-fluoro-5-[5-ethyl-3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-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-2-fluoro-5-sulfanylphenyl)-5-ethyl-1-methyl-6-(trifluoromethyl)pyrimidine-

2,4(1H,3H)-dione (84% of theory) as a colorless solid. 2Chloropropanecarboxylic 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-2fluoro-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)-3,6-dihydropyrimidine -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-dimethyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]4-fluorophenyl}sulfanyl) propanoic acid (110 mg, 0.24 mmol), 1-hydroxy-1H-benzotriazole (42 mg, 0.31 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (60 mg, 0.31 mmol) dissolved in abs. dichloromethane in a heated round bottom flask under argon and, after stirring at room temperature for 5 minutes, 2-(hydroxymethyl)tetrahydrofuran (32 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 tetrahydrofuran-2-ylmethyl-2-({2-chloro-5-[5-ethyl3-methyl-2,6-dioxo-4-(trifluoromethyl)- 3,6-dihydropyrimidin-1(2H)-yl]-4-fluorophenyl}sulfanyl)propanoate (58 mg, 43% of theory) as a high viscosity colorless oil. 1H-NMR (CDCl ₃ δ, ppm) 7.56-7.52 (m, 1H), 7.38-7.33 (m, 1H), 4.18-3.88 (m, 4H), 3 .83-3.68 (m, 2H), 3.54 (s, 3H), 2.74-2.68 (m, 2H), 2.01-1.82 (m, 3H), 1.64 -1.50 (m, 4H), 1.13 (t, 3H).

By analogy with the above preparation examples, which were indicated in the appropriate place, and taking into account the general details for the preparation of substituted N-heterocyclyl- and N-heteroaryltetrahydropyrimidinones, 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).

Table I.1. Preferred compounds of formula (I.1) are compounds I.1-1-I.1345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.1-1-I.1-345 from table. I.1 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

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Table 1

No. Q 1 Q-1 2 Q-2 3 Q-3 4 Q-4 5 Q-5 6 Q-6 7 Q-7 8 Q-8 9 Q-9 10 Q-10 AND Q-11 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

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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-3 8 39 Q-39 40 Q-40 41 Q-41 42 Q-42 43 Q-43 44 Q-44 45 Q-45 46 Q-46 47 Q-47 48 Q-48 49 Q-49 50 Q-50 51 Q-51

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52 Q-52 53 Q-53 54 Q-54 55 Q-55 56 Q-56 57 Q-57 58 Q-58 59 Q-59 60 Q-60 61 Q-61 62 Q-62 63 Q-63 64 Q-64 65 Q-65 66 Q-66 67 Q-67 68 Q-68 69 Q-69 70 Q-70 71 Q-71 72 Q-72 73 Q-73 74 Q-74 75 Q-75 76 Q-76 77 Q-77 78 Q-78 79 Q-79 80 Q-80 81 Q-81 82 Q-82

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Table I.2. Preferred compounds of formula (I.2) are compounds I.2-1-I.2345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.2-1-I.2-345 from table. I.2 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.3. Preferred compounds of formula (I.3) are compounds I.3-1-I.3345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.3-1-I.3-345 from table. I.3 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.4. Preferred compounds of formula (I.4) are compounds I.4-1-I.4345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.4-1-I.4-345 from table. I.4 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.5. Preferred compounds of formula (I.5) are compounds I.5-1-I.5345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.5-1-I.5-345 from table. I.5 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.6. Preferred compounds of formula (I.6) are compounds I.6-1-I.6345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.6-1-I.6-345 from table. I.6 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.7. Preferred compounds of formula (I.7) are compounds I.7-1-I.7345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.7-1-I.7-345 from table. I.7 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.8. Preferred compounds of formula (I.8) are compounds I.8-1-I.8345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.8-1-I.8-345 from table. I.8 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.9. Preferred compounds of formula (I.9) are compounds I.9-1-L9345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.9-1-I.9-345 from table. I.9 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

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Table I.10. Preferred compounds of formula (I.10) are compounds I.10-11.10-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.10-1-I.10-345 from table. I.10 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.11. Preferred compounds of formula (I.11) are compounds I.11-1I.11-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.11-1-I.11-345 from table. I.11 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.12. Preferred compounds of formula (I.12) are compounds I.12-1I.12-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.12-1-I.12-345 from table. I.12 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.13. Preferred compounds of formula (I.13) are compounds I.13-1I.13-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.13-1-I.13-345 from table. I.13 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.14. Preferred compounds of formula (I.14) are compounds I.14-1I.14-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.14-1-I.14-345 from table. I.14 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.15. Preferred compounds of formula (I.15) are compounds I.15-1I.15-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.15-1-I.15-345 from table. I.15 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.16. Preferred compounds of formula (I.16) are compounds I.16-1I.16-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.16-1-I.16-345 from table. I.16 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

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Table I.17. Preferred compounds of formula (I.17) are compounds I.17-1I.17-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.17-1-I.17-345 from table. I.17 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.18. Preferred compounds of formula (1.18) are compounds I.181-I.18-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.18-1-I.18-345 from table. 1.18 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.19. Preferred compounds of formula (I.19) are compounds I.19-1I.19-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.19-1-I.19-345 from table. I.19 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.20. Preferred compounds of formula (I.20) are compounds I.20-1I.20-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.20-1-I.20-345 from table. I.20 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.21. Preferred compounds of formula (I.21) are compounds I.21-1I.21-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.21-1-I.21-345 from table. I.21 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.22. Preferred compounds of formula (I.22) are compounds I.22-1I.22-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.22-1-I.22-345 from table. I.22 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.23. Preferred compounds of formula (I.23) are compounds I.23-1I.23-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.23-1-I.23-345 from table. I.23 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.24. Preferred compounds of formula (I.24) are compounds I.24-1I.24-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.24-1-I.24-345 from table. I.24 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

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Table I.25. Preferred compounds of formula (I.25) are compounds I.25-1I.25-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.25-1-I.25-345 from table. I.25 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.26. Preferred compounds of formula (I.26) are compounds I.26-1I.26-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.26-1-I.26-345 from table. I.26 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.27. Preferred compounds of formula (I.27) are compounds I.27-1I.27-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.27-1-I.27-345 from table. I.27 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.28. Preferred compounds of formula (I.28) are compounds I.28-1I.28-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.28-1-I.28-345 from table. I.28 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.29. Preferred compounds of formula (I.29) are compounds I.29-1I.29-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.29-1-I.29-345 from table. I.29 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.30. Preferred compounds of formula (I.30) are compounds I.30-1I.30-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.30-1-I.30-345 from table. I.30 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.31. Preferred compounds of formula (I.31) are compounds I.31-1I.31-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.31-1-I.31-345 from table. I.31 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

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Table I.32. Preferred compounds of formula (I.32) are compounds I.32-1I.32-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.32-1-I.32-345 from table. I.32 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.33. Preferred compounds of formula (I.33) are compounds I.33-1I.33-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.33-1-I.33-345 from table. I.33 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.34. Preferred compounds of formula (I.34) are compounds I.34-1I.34-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.34-1-I.34-345 from table. I.34 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.35. Preferred compounds of formula (I.35) are compounds I.35-1I.35-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.35-1-I.35-345 from table. I.35 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.36. Preferred compounds of formula (I.36) are compounds I.36-1I.36-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.36-1-I.36-345 from table. I.36 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.37. Preferred compounds of formula (I.37) are compounds I.37-1I.37-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.37-1-I.37-345 from table. I.37 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.38. Preferred compounds of formula (I.38) are compounds I.38-1I.38-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.38-1-I.38-345 from table. I.38 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.39. Preferred compounds of formula (I.39) are compounds I.39-1I.39-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.39-1-I.39-345 from table. I.39 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

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Table I.40. Preferred compounds of formula (I.40) are compounds I.40-1I.40-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.40-1-I.40-345 from table. I.40 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.41. Preferred compounds of formula (I.41) are compounds I.41-1I.41-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.41-1-I.41-345 from table. I.41 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.42. Preferred compounds of formula (I.42) are compounds I.42-1I.42-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.42-1-I.42-345 from table. I.42 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.43. Preferred compounds of formula (I.43) are compounds I.43-1I.43-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.43-1-I.43-345 from table. I.43 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.44. Preferred compounds of formula (I.44) are compounds I.44-1I.44-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.44-1-I.44-345 from table. I.44 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.45. Preferred compounds of formula (I.45) are compounds I.45-1I.45-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.45-1-I.45-345 from table. I.45 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.46. Preferred compounds of formula (I.46) are compounds I.46-1I.46-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.46-1-I.46-345 from table. I.46 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

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Table I.47. Preferred compounds of formula (I.47) are compounds I.47-1I.47-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.47-1-I.47-345 from table. I.47 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.48. Preferred compounds of formula (I.48) are compounds I.48-1I.48-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.48-1-I.48-345 from table. I.48 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.49. Preferred compounds of formula (I.49) are compounds I.49-1I.49-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.49-1-I.49-345 from table. I.49 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.50. Preferred compounds of formula (I.50) are compounds I.50-1I.50-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.50-1-I.50-345 from table. I.50 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.51. Preferred compounds of formula (I.51) are compounds I.51-1I.51-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.51-1-I.51-345 from table. I.51 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.52. Preferred compounds of formula (I.52) are compounds I.52-1I.52-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.52-1-I.52-345 from table. I.52 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.53. Preferred compounds of formula (I.53) are compounds I.53-1I.53-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.53-1-I.53-345 from table. I.53 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.54. Preferred compounds of formula (I.54) are compounds I.54-1I.54-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.54-1-I.54-345 from table. I.54 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

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Table I.55. Preferred compounds of formula (I.55) are compounds I.55-1I.55-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.55-1-I.55-345 from table. I.55 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.56. Preferred compounds of formula (I.56) are compounds I.56-1I.56-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.56-1-I.56-345 from table. I.56 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.57. Preferred compounds of formula (I.57) are compounds I.57-1I.57-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.57-1-I.57-345 from table. I.57 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.58. Preferred compounds of formula (I.58) are compounds I.58-1I.58-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.58-1-I.58-345 from table. I.58 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.59. Preferred compounds of formula (I.59) are compounds I.59-1I.59-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.59-1-I.59-345 from table. I.59 are thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

Table I.60. Preferred compounds of formula (I.60) are compounds I.60-1I.60-345, in which Q has the definitions from table. 1, which are given in the corresponding line. Compounds I.60-1-I.60-345 from table. I.60 is thus determined by the value of the corresponding entries No. 1-345 for Q from Table. 1.

NMR data for selected examples.

a) Traditional interpretation of NMR.

Example No. I.12-91.

¹ H-NMR (CDCls δ, ppm) 7.52 (m, 1H), 7.34 (m, 1H), 4.12-4.08 (m, 1H), 4.06-3.89 (m , 2H), 3.77-3.72 (m, 1H), 3.54 (s, 3H), 3.51-3.34 (m, 2H), 2.24-2.20 (m, 3H ), 2.03-1.93 (m, 1H), 1.90-1.79 (m, 2H), 1.58-1.47 (m, 3H), 1.31-1.23 (m , 2H), 1.07 (t, 3H).

Example No. I.12-221.

¹ H-NMR (CDCl ₃ δ, ppm) 7.33 (m, 1H), 7.19 (m, 1H), 6.72 (br. m, 1H, NH), 3.91-3.77 ( m, 1H), 3.75-3.69 (m, 1H), 3.67-3.62 (m, 2H), 3.55 (s, 3H), 3.51-3.40 (m, 1H), 3.21-3.08 (m, 1H), 2.24-2.20 (m, 3H), 2.09-2.02 (m, 1H), 1.96-1.70 ( m, 4H), 1.49/1.33 (m, 1H), 1.12 (t, 3H).

Example No. I.14-71.

1H-NMR (CDCl ₃ δ, ppm) 7.51 (m, 1H), 7.34 (m, 1H), 4.16-4.10 (m, 1H), 4.07-3.85 (m , 3H), 3.81-3.67(m, 2H), 3.54(s, 3H), 2.24-2.21(m, 3H), 1.96-1.80(m, 4H ), 1.78-1.74 (m, 1H), 1.69-1.65 (m, 1H), 1.53-1.48 (m, 1H), 0.97-0.93 (m , 6H).

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Example No. I.48-127.

'll-NMR (CDCl ₃ δ, ppm) 7.48 (m, 1H), 7.32 (m, 1H), 6.29 (m, 1H), 4.19-4.14 (m, 1H) , 3.92-3.70 (m, 3H),

3.59-3.54 (m, 1H), 3.53 (s, 3H), 3.11 (s, 2H), 1.84-1.75 (m, 2H), 1.66-1, 59 (m, 2H), 1.31 (s, 6H).

Example No. I.54-241.

¹ H-NMR (CDCl3 δ, ppm) 7.33-7.27 (m, 2H), 6.73 (br. m, 1H, NH), 4.07-4.03 (m, 2H), 3 .98-3.94(m, 1H), 3.54(s, 3H), 3.52-3.48(m, 1H), 3.43-3.38(m, 1H), 3.13 (s, 2H), 2.26-2.23 (m, 2H), 1.88-1.82 (m, 1H), 1.631.48 (m, 4H), 1.39-1.31 (m , 2H), 1.30 (s, 6H).

b) List of peaks in the NMR method.

1H NMR data for selected examples are shown as 1H NMR peak lists. For each signal peak, the δ value in ppm is given first, followed by 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 ^;................; δ _i (intensity i); ......; δ _n (intensity _n ).

The intensity of the distinct signals correlates with the height of the signals in the printed example of the NMR spectrum in cm and shows the real relationship of the signal intensity values. In the case of wide signals, several peaks or the center of the signal and its relative intensity compared to the most intense signal in the spectrum can be shown. To calibrate the chemical shifts of ^{the 1} H NMR spectra, 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 1H-NMR. Additional details for 1H NMR peak listings can be found in Research Disclosure Database #564025.

Example No. I.1-1.

1 H-NMR (400.0 MHz, d ₆ -DMSO): δ = 7.8581 (5.0); 7.8343 (5.1); 7.7555 (4.4); 7.7521 (4.6); 7.7365 (4.4); 7.7330 (4.5); 6.6090 (7.8); 6.6018 (7.3); 4.1623(1.3); 4.1529(1.4); 4.1477 (1.6); 4.1380 (1.6); 4.1326 (3.0); 4.1234 (3.1); 4.1174 (3.8); 4.1082 (3.2); 4.0965(2.2); 4.0861 (5.0); 4.0805 (6.1); 4.0760 (2.8); 4.0679 (4.8); 4.0629 (4.0); 4.0503 (2.0); 4.0461 (1.8); 4.0371 (0.7); 3.4700 (0.7); 3.4611 (1.1); 3.4410 (4.1); 3.4218 (22.0); 3.4092 (3.6); 3.4059 (2.9); 3.3896 (0.9); 3.3861 (0.9); 3.3670 (0.6); 3.3580 (1.4); 3.3420 (1.3); 3.3090 (340.3); 3.2586 (0.6); 3.1931 (66.1); 2.6739 (1.5); 2.6692 (2.1); 2.6648 (1.5); 2.5225 (11.0); 2.5092 (126.4); 2.5047 (249.2); 2.5002 (330.8); 2.4956 (234.6); 2.4912 (107.9); 2.3315 (1.5); 2.3270 (2.0); 2.3225 (1.4); 2.0719 (0.6); 1.4280 (16.0); 1.4108 (15.6); 1.2356 (1.4); 0.0079 (1.2); -0.0002 (23.5); -0.0086 (0.8).

Example No. I.1-2.

¹ H-NMR (400.0 MHz, CDCl3): δ = 7.5397 (3.3); 7.5341 (3.2); 7.5209 (3.4); 7.5153 (3.2); 7.3790 (3.7); 7.3772 (3.6); 7.3563 (3.7); 7.3545(3.6); 7.2715 (0.6); 7.2691 (0.8); 7.2601(121.6); 6.9961 (0.7); 6.3470 (6.9); 4.2477 (0.6); 4.2422 (0.6); 4.2387 (0.7); 4.2330 (0.7); 4.2315 (0.8); 4.2259 (0.7); 4.2223 (0.7); 4.2179 (1.4);

4.2125 (1.4); 4.2091 (1.3); 4.2035 (1.5); 4.2017 (1.7); 4.1961 (1.6); 4.1926 (1.3); 4.1871 (1.3); 4.1659 (2.0);

4.1570(2.4); 4.1520(2.2); 4.1432 (2.2); 4.1363 (1.0); 4.1272 (1.0); 4.1225 (1.1); 4.1135 (1.0); 3.9568 (0.8);

3.9541 (0.8); 3.9390 (2.9); 3.9362 (3.0); 3.9211 (3.0); 3.9184 (3.0); 3.9033 (0.8); 3.9006 (0.8); 3.5776 (0.6);

3.5754 (0.6); 3.5685 (0.8); 3.5663 (0.9); 3.5638 (0.9); 3.5615 (1.0); 3.5525 (14.7); 3.5493 (16.0); 3.5466 (7.3); 3.5400 (2.0); 3.5377 (2.0); 3.5352 (2.1); 3.5330 (2.0); 3.5240 (3.9); 3.5150 (2.9); 3.5075 (2.5); 3.4986 (2.5);

3.4955 (1.2); 3.4916 (2.0); 3.4883 (2.3); 3.4789 (1.2); 3.4741(6.2); 3.4708 (7.4); 3.4566 (6.5); 3.4533 (7.1);

3.4391 (2.2); 3.4358 (2.3); 1.5468 (4.2); 1.5375 (11.9); 1.5344 (11.9); 1.5196 (10.7); 1.5165 (11.0); 1.1773 (6.8); 1.1744 (7.2); 1.1598 (13.9); 1.1569 (14.6); 1.1422(6.7); 1.1394 (6.9); 0.0080 (1.5); 0.0063 (0.6); 0.0055 (0.6); 0.0046 (0.7); -0.0002 (45.4); -0.0051 (0.8); -0.0059 (0.6); -0.0068 (0.5); -0.0085 (1.3).

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Example No. I.1-6.

1 H-NMR (400.0 MHz, CDCl ₃ ): δ = 7.5328 (0.9); 7.5276 (0.9); 7.5181 (0.6); 7.5140 (0.9); 7.5088 (0.8);

7.3395 (0.9); 7.3367 (0.9); 7.3198 (2.1); 7.3173 (2.5); 7.3063 (2.3); 7.2982 (1.1); 7.2942 (2.2); 7.2800 (0.7);

7.2592 (78.8); 6.3060 (1.7); 4.4956 (2.9); 4.1932 (0.6); 4.1876 (0.6); 4.1792 (0.5); 3.9513 (0.6); 3.9463 (0.7);

3.9334 (0.7); 3.9284 (0.8); 3.6000 (0.6); 3.5914 (0.6); 3.5860 (0.6); 3.5774 (0.5); 3.5692 (0.6); 3.5607 (0.7);

3.5527 (0.6); 3.5442 (0.6); 3.5181(3.4); 3.5148 (2.7); 1.5387 (3.1); 1.5363 (3.9); 1.5328 (16.0); 1.5209 (2.8); 1.5187 (2.8); 0.0080 (0.9); -0.0002 (28.4); -0.0085 (1.0).

Example No. I.1-23.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5409 (1.6); 7.5320 (1.5); 7.5220 (1.6); 7.5197 (0.5); 7.5132 (1.5); 7.3815 (1.8); 7.3797 (1.7); 7.3587 (1.8); 7.3569 (1.7); 7.2606 (50.8); 6.3467 (2.5); 6.3433 (2.6); 4.2511 (0.5); 4.2372 (0.6); 4.2307 (0.6); 4.2284 (0.6); 4.2212 (1.0); 4.2144 (0.8); 4.2119 (0.6); 4.2053 (0.6); 4.1845 (0.7);

4.1756 (0.8); 4.1745 (0.9); 4.1706 (0.8); 4.1616 (0.8); 3.9293 (1.3); 3.9244 (1.4); 3.9114 (1.3); 3.9065 (1.4);

3.6225 (0.7); 3.6192 (0.8); 3.6135 (0.7); 3.6100 (0.9); 3.6087 (0.9); 3.6052 (0.8); 3.5994 (0.7); 3.5962 (0.7);

3.5904 (1.1); 3.5861 (1.0); 3.5817 (2.0); 3.5794 (1.3); 3.5758 (2.1); 3.5720 (2.5); 3.5687(2.6); 3.5644 (2.6);

3.5622 (3.1); 3.5579 (3.1); 3.5522 (7.2); 3.5492 (7.2); 3.5460 (3.2); 3.5093 (2.8); 3.5079 (2.9); 3.5019 (1.6);

3.4986 (1.4); 3.4952 (2.2); 3.4860 (1.3); 3.3571 (15.3); 3.3552 (16.0); 1.5520 (13.3); 1.5348 (5.1); 1.5322 (5.3); 1.5169 (5.0); 1.5143 (5.2); 0.0080 (0.6); -0.0002 (19.0); -0.0085 (0.6).

Example No. I.1-26.

1H-NMR (400.0 MHz, CDCl3): δ = 7.4990 (1.2); 7.4958 (1.2); 7.4803 (1.2); 7.4771 (1.2); 7.3772 (2.2); 7.3545(2.2); 7.2599 (53.8); 6.3496 (3.4); 4.1628 (0.9); 4.1463 (1.9); 4.1422 (0.6); 4.1298 (1.7); 4.1261 (1.0);

4.1135 (0.5); 3.8961 (1.1); 3.8940 (1.1); 3.8783 (1.1); 3.8761 (1.1); 3.5553 (5.0); 3.5522(5.2); 3.5491 (2.1);

3.3709(2.2); 3.3551 (4.7); 3.3394 (2.2); 3.2888 (16.0); 1.8226(1.1); 1.8197 (0.7); 1.8179 (0.7); 1.8067 (1.7);

1.8035 (1.0); 1.7909 (1.1); 1.7873 (0.7); 1.5428 (2.4); 1.5304 (4.5); 1.5290 (4.6); 1.5125 (4.4); 1.5112 (4.4);

0.0080 (0.7); -0.0002 (21.3); -0.0085 (0.6).

Example No. I.1-27.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5187 (1.0); 7.4987(2.9); 7.4955 (2.9); 7.4799 (3.0); 7.4767 (2.9);

7.3753 (5.5); 7.3525 (5.4); 7.2598 (178.1); 6.9958 (1.0); 6.3486 (8.0); 4.2021 (0.6); 4.1857 (1.3); 4.1749 (2.0);

4.1694 (0.8); 4.1585 (3.8); 4.1521(1.3); 4.1490 (1.2); 4.1422 (2.1); 4.1361 (2.4); 4.1329 (2.3); 4.1200 (1.3);

4.1168 (1.2); 4.1089 (0.8); 4.1057 (0.8); 3.9141 (0.7); 3.9104 (0.7); 3.8963 (2.4); 3.8924 (2.4); 3.8784 (2.4);

3.8746 (2.4); 3.8605 (0.7); 3.8567 (0.7); 3.5549 (12.8); 3.5519 (13.0); 3.4574 (3.1); 3.4399 (9.7); 3.4223 (10.0); 3.4127 (5.1); 3.4048 (3.6); 3.3969 (10.8); 3.3811 (5.2); 1.8436 (0.7); 1.8277 (2.5); 1.8247 (1.8); 1.8118 (3.6); 1.8086(2.6); 1.7959 (2.4); 1.7923 (1.7); 1.7798 (0.6); 1.5391 (48.0); 1.5282 (11.1); 1.5271 (11.2); 1.5104 (10.8); 1.5093 (10.8); 1.1833 (8.1); 1.1657 (16.0); 1.1483 (7.7); 0.0080 (2.6); -0.0002 (68.8); -0.0085 (1.9).

Example No. I.1-30.

1H-NMR (400.0 MHz, CDCl3): δ = 7.4874 (2.6); 7.4843 (2.6); 7.4687 (2.6); 7.4656 (2.6); 7.3539 (0.9); 7.3482 (5.1); 7.3367 (1.8); 7.3324 (3.3); 7.3297 (3.5); 7.3254 (5.4); 7.3144 (8.6); 7.3083 (7.4); 7.2897 (2.2); 7.2858 (1.7); 7.2828 (1.2); 7.2753 (1.1); 7.2679 (2.5); 7.2589 (80.3); 6.3305 (4.0); 6.3262 (4.0); 4.4641 (13.0); 4.2120 (0.7); 4.2013 (1.0); 4.1992 (1.0); 4.1846 (2.0); 4.1775 (1.0); 4.1731 (1.0); 4.1687 (1.2); 4.1615 (1.9);

4.1571 (1.8); 4.1455 (1.2); 4.1410 (0.9); 4.1343 (0.6); 4.1299 (0.6); 3.8943 (0.5); 3.8880 (0.5); 3.8765 (1.8);

3.8701 (1.9); 3.8586 (1.9); 3.8523 (2.0); 3.8409 (0.6); 3.8345 (0.5); 3.5320 (5.7); 3.5290 (5.9); 3.5252 (3.6);

3.5209 (5.8); 3.5179 (5.8); 3.4740 (3.5); 3.4584 (7.6); 3.4428 (3.7); 1.8671 (1.3); 1.8640 (1.5); 1.8588 (1.2);

1.8513 (1.9); 1.8482 (2.1); 1.8429 (1.7); 1.8355 (1.3); 1.8325 (1.4); 1.8266 (1.1); 1.5396 (16.0); 1.5037(9.4); 1.4858 (9.2); 0.0080 (0.9); -0.0002 (28.4); -0.0085 (1.1).

Example No. I.1-41.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5027 (2.8); 7.4969 (2.7); 7.4839 (2.8); 7.4781 (2.6); 7.3968 (4.7); 7.3741 (4.7); 7.2601 (75.4); 6.3476 (4.2); 6.3359 (4.5); 4.2864 (0.5); 4.2768 (0.5); 4.2691 (0.6); 4.2625 (1.2); 4.2552 (1.3); 4.2456 (1.4); 4.2380 (1.4); 4.2290 (0.7); 4.2205 (1.2); 4.2074 (1.4); 4.1987 (0.9); 4.1762 (0.5);

4.0936 (0.6); 4.0891 (0.7); 4.0858 (0.7); 4.0806 (0.8); 4.0758 (0.6); 4.0721 (0.5); 4.0648 (1.2); 4.0602 (1.4);

4.0571 (1.3); 4.0518 (1.7); 4.0462 (1.1); 4.0433 (1.1); 4.0392 (1.0); 4.0184 (1.3); 4.0158 (1.3); 4.0114 (1.2);

4.0080 (1.3); 4.0012 (1.3); 3.9991 (1.3); 3.9936 (2.0); 3.9819 (0.8); 3.9746 (3.3); 3.9569 (3.0); 3.9393 (1.0);

3.5485 (9.6); 3.5456 (13.2); 3.5424 (9.5); 1.5641 (16.0); 1.5510 (10.5); 1.5489 (10.7); 1.5331 (9.8); 1.5311 (10.0); 0.0080 (1.0); -0.0002 (28.5); -0.0084 (1.1).

Example No. I.1-48.

1H-NMR (400.0 MHz, CDCl3): δ = 7.4827 (3.6); 7.4756 (3.6); 7.4640 (3.7); 7.4569 (3.6); 7.3941 (6.3); 7.3714 (6.3); 7.2601 (69.5); 6.3516 (6.0); 6.3465 (6.1); 4.1836 (0.6); 4.1683 (0.9); 4.1641 (0.9); 4.1556(1.4); 4.1514 (1.6); 4.1401 (2.1); 4.1361 (2.3); 4.1247 (2.4); 4.1206 (1.8); 4.1188 (1.7); 4.1091 (2.3); 4.1033 (2.1);

4.0938 (1.6); 4.0881 (1.4); 4.0810 (0.9); 4.0753 (0.9); 4.0600 (0.5); 3.9536 (0.9); 3.9482 (0.9); 3.9357 (3.1);

3.9304 (3.2); 3.9179 (3.2); 3.9126 (3.3); 3.9001 (0.9); 3.8948 (0.9); 3.5521 (16.0); 2.8422 (2.3); 2.8233 (4.3);

2.8052(2.6); 1.9510 (0.9); 1.9339 (2.6); 1.9170 (3.7); 1.9006(2.5); 1.8826 (0.7); 1.5430 (9.4); 1.5355 (14.1);

1.5333 (14.2); 1.5177 (13.0); 1.5155 (13.3); 0.0080 (1.4); -0.0002 (41.0); -0.0085 (1.3).

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Example No. I.1-51.

1 H-NMR (400.0 MHz, CDCl ₃ ): δ 7.5376 (1.7); 7.5324 (1.7); 7.5189 (1.8); 7.5132 (3.6); 7.4940 (2.3); 7.3769 (3.6); 7.3724 (2.8); 7.3541 (3.6); 7.3496 (2.8); 7.2609 (45.7); 6.3468 (6.2); 4.1354 (0.6); 4.1307 (0.7);

4.1257 (0.7); 4.1207 (0.6); 4.1067 (0.9); 4.1020 (0.9); 4.0969 (0.9); 4.0920 (0.9); 4.0259 (2.8); 4.0221 (3.5);

4.0150 (1.9); 4.0108 (2.8); 4.0085 (2.3); 3.9867 (1.0); 3.9839 (1.1); 3.9722 (1.1); 3.9693 (1.6); 3.9581 (0.8);

3.9552 (0.9); 3.9512 (2.2); 3.9428 (2.0); 3.9333 (2.2); 3.9267 (1.6); 3.9246 (1.6); 3.9155 (0.7); 3.5506 (12.7);

3.4955 (0.6); 3.4856 (0.6); 3.4804 (0.8); 3.4702 (0.8); 3.4648 (0.7); 3.4548 (0.6); 3.4459 (0.6); 3.4315 (0.9);

3.4301 (0.9); 3.4179 (0.8); 3.4157 (0.9); 3.4020 (0.5); 3.3119 (11.2); 3.3079 (11.9); 3.2969 (16.0); 3.2954 (15.9); 3.2888 (1.2); 1.5673 (3.6); 1.5440 (12.3); 1.5261 (12.0); 1.0981 (9.4); 1.0819 (11.4); 1.0685(4.4); 1.0647 (4.6); 0.0080 (0.5); -0.0002 (18.6); -0.0085 (0.6).

Example No. I.1-71.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5648 (2.1); 7.5583 (2.1); 7.5460 (2.2); 7.5394 (2.2); 7.5304 (3.9); 7.5195 (0.7); 7.5116 (3.9); 7.3735 (5.1); 7.3507 (5.1); 7.3107 (0.6); 7.2687 (0.6); 7.2679 (0.6); 7.2671 (0.7);

7.2663 (0.9); 7.2654 (1.1); 7.2646 (1.4); 7.2606 (89.1); 7.2542 (1.4); 7.2533 (1.2); 7.2525 (1.0); 7.2517 (0.9);

7.2509 (0.9); 7.2501 (0.8); 7.2493 (0.7); 7.2485 (0.7); 7.2477 (0.6); 7.2469 (0.6); 7.2461 (0.6); 7.2453 (0.6);

7.2445 (0.5); 7.2437 (0.5); 6.9965 (0.5); 6.3436 (7.1); 4.1548 (1.0); 4.1460 (1.3); 4.1445 (1.2); 4.1358 (1.2);

4.1270(1.3); 4.1180 (1.8); 4.1082 (1.5); 4.0605 (0.9); 4.0522 (1.6); 4.0444 (1.5); 4.0346 (2.2); 4.0286 (2.3);

4.0216 (2.0); 4.0178 (2.8); 4.0117 (2.3); 4.0080 (2.6); 4.0015 (2.7); 3.9908 (3.0); 3.9877 (3.0); 3.9805 (1.7);

3.9784 (1.9); 3.9755 (2.6); 3.9722 (1.7); 3.9676 (0.9); 3.9632 (1.9); 3.9593 (3.6); 3.9476 (1.2); 3.9441 (1.5);

3.9412 (3.5); 3.9235 (3.8); 3.9057 (3.1); 3.8879 (0.9); 3.8365 (0.5); 3.8324 (0.5); 3.8292 (0.5); 3.8274 (0.6);

3.8196 (0.8); 3.8154 (1.6); 3.8117 (1.7); 3.8063 (1.2); 3.8033 (0.7); 3.7989 (1.6); 3.7946 (1.8); 3.7912 (1.9);

3.7892 (1.7); 3.7826 (0.8); 3.7783 (0.7); 3.7748 (0.9); 3.7571 (0.6); 3.7533 (0.7); 3.7421 (1.2); 3.7372 (1.5);

3.7242 (1.6); 3.7214 (1.9); 3.7194 (1.9); 3.7086 (0.7); 3.7033 (1.4); 3.6985 (0.8); 3.5505 (14.1); 3.5475 (16.0); 3.5442 (9.5); 1.9589 (0.6); 1.9549 (0.6); 1.9512 (0.6); 1.9468 (0.8); 1.9422 (0.9); 1.9390 (0.8); 1.9294 (1.1);

1.9257 (1.2); 1.9212 (1.1); 1.9124 (0.8); 1.9085 (1.6); 1.9018 (1.3); 1.8974 (1.1); 1.8883 (1.6); 1.8853 (1.4);

1.8821 (1.6); 1.8801 (1.6); 1.8729 (1.5); 1.8701 (2.0); 1.8665 (2.0); 1.8622 (1.6); 1.8578 (1.6); 1.8534 (2.0);

1.8497 (2.3); 1.8459 (1.6); 1.8368 (1.8); 1.8323 (1.6); 1.8281 (1.0); 1.8237 (0.9); 1.8190 (1.1); 1.8110 (0.7);

1.8023 (0.7); 1.5444 (7.3); 1.5401 (14.1); 1.5367 (8.6); 1.5265 (8.0); 1.5222 (14.2); 1.5189 (8.9); 1.5093 (1.5); 1.5068 (1.5); 1.5008 (1.4); 1.4894 (1.1); 1.4827 (0.8); 1.4718 (0.6); 0.0079 (1.0); -0.0002 (34.7); -0.0051 (0.8); -0.0060 (0.7); -0.0068 (0.6); -0.0085 (1.3).

Example No. I.1-72.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5183 (2.8); 7.4878 (2.2); 7.4839 (4.0); 7.4690 (2.2); 7.4652 (4.0);

7.3851 (4.2); 7.3789 (0.5); 7.3624 (4.3); 7.3095 (0.6); 7.2780 (0.8); 7.2772 (0.8); 7.2755 (1.0); 7.2748 (1.1);

7.2740 (1.1); 7.2731 (1.3); 7.2724 (1.4); 7.2715 (1.6); 7.2707 (1.9); 7.2699 (2.3); 7.2692(2.6); 7.2684 (2.9);

7.2675 (3.4); 7.2667 (4.1); 7.2659 (5.1); 7.2651(6.2); 7.2594 (494.5); 7.2481 (1.6); 7.2474 (1.5); 7.2466 (1.3);

7.2458 (1.0); 7.2450 (1.0); 7.2442 (0.9); 7.2434 (0.8); 7.2426 (0.8); 7.2418 (0.7); 7.2402 (0.6); 7.2379 (0.7);

7.2313 (0.5); 7.2290 (0.6); 7.2100 (1.2); 6.9954 (2.9); 6.3491 (8.5); 4.1065 (0.7); 4.0954 (0.7); 4.0900 (0.8);

4.0790 (1.4); 4.0684 (1.0); 4.0629 (1.1); 4.0584 (0.7); 4.0516 (1.1); 4.0423 (0.6); 4.0379 (0.6); 4.0315 (1.2);

4.0271 (1.3); 4.0153 (1.2); 4.0108 (1.2); 3.9912 (1.8); 3.9716 (1.8); 3.9643 (0.9); 3.9524 (1.2); 3.9496 (1.3);

3.9452 (1.3); 3.9331 (1.4); 3.9280 (2.1); 3.9250 (2.5); 3.9191 (2.7); 3.9100 (1.8); 3.9068 (2.3); 3.9014 (2.9);

3.8890 (0.6); 3.8833 (0.7); 3.8324 (0.7); 3.8116 (1.8); 3.7979 (1.8); 3.7776 (1.1); 3.7698 (1.4); 3.7521(1.9);

3.7476 (1.7); 3.7351 (2.1); 3.7304 (2.9); 3.7165 (2.2); 3.7129 (2.3); 3.6993 (1.3); 3.6927 (1.3); 3.6723 (0.5);

3.5527 (15.6); 3.5498 (16.0); 3.4694 (1.4); 3.4561 (2.8); 3.4470 (1.4); 3.4425 (1.8); 3.4340 (2.5); 3.4205 (1.3); 2.4781 (0.7); 2.4607 (1.1); 2.4446 (1.1); 2.4253 (0.8); 2.0052 (0.5); 1.9926 (0.6); 1.9854 (0.6); 1.9719 (1.1);

1.9592 (1.0); 1.9530 (1.0); 1.9404 (1.1); 1.9271 (0.6); 1.9206 (0.6); 1.7155 (0.6); 1.5875 (4.4); 1.5610(2.2);

1.5356 (17.2); 1.5178 (16.6); 1.4932 (0.5); 0.1462 (0.6); 0.0080 (6.1); 0.0064 (2.8); -0.0002 (180.8); -0.0067 (2.5); -0.0085 (5.4); -0.1495 (0.6).

Example No. I.1-73.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5193 (0.8); 7.4895 (0.9); 7.4869 (1.1); 7.4844 (1.8); 7.4795 (3.2);

7.4708 (1.0); 7.4682 (1.1); 7.4657 (1.8); 7.4607 (3.2); 7.3851 (4.5); 7.3814 (1.9); 7.3624 (4.4); 7.3585 (1.9);

7.2750 (0.5); 7.2742 (0.6); 7.2734 (0.6); 7.2726 (0.7); 7.2718 (0.8); 7.2710 (0.8); 7.2702 (0.9); 7.2694 (1.0);

7.2686 (1.1); 7.2677 (1.3); 7.2670 (1.5); 7.2661 (1.8); 7.2603 (139.3); 6.9964 (0.8); 6.3486 (9.3); 4.1031 (0.5);

4.0985 (0.5); 4.0877 (0.8); 4.0760 (0.9); 4.0713 (0.8); 4.0590 (1.0); 4.0521 (0.6); 4.0406 (0.6); 4.0361 (0.7);

4.0325 (0.5); 4.0250 (1.7); 4.0092 (2.1); 3.9949 (2.6); 3.9840 (0.8); 3.9767 (2.3); 3.9683 (0.7); 3.9637 (1.1);

3.9579 (1.5); 3.9530 (1.1); 3.9498 (1.2); 3.9450 (0.9); 3.9362 (2.8); 3.9314 (2.1); 3.9271 (1.5); 3.9245 (1.8);

3.9225 (2.5); 3.9182 (3.5); 3.9094 (1.8); 3.9066 (2.2); 3.9046 (2.8); 3.9004 (3.4); 3.8940 (1.0); 3.8896 (1.2);

3.8857 (1.9); 3.8828 (1.4); 3.8679 (0.6); 3.6971 (0.6); 3.6843 (0.6); 3.6787 (0.8); 3.5981 (0.8); 3.5911 (0.7);

3.5848 (0.9); 3.5765 (1.0); 3.5686 (0.7); 3.5534 (15.6); 3.5505 (16.0); 3.3818 (0.6); 3.3786 (0.6); 3.3674 (1.0); 3.3627 (0.7); 3.3595 (0.6); 3.3543 (0.8); 3.3448 (0.8); 3.3404 (0.6); 3.3313 (0.6); 2.5282 (0.5); 2.5223 (0.6);

2.5073 (0.7); 2.4890 (0.6); 1.7064 (0.7); 1.6903 (0.8); 1.6868 (0.7); 1.6746 (1.1); 1.6702 (0.6); 1.6580 (0.6);

1.5762 (0.9); 1.5595 (7.6); 1.5442 (1.5); 1.5322 (15.1); 1.5144 (14.7); 1.2426(6.2); 1.2399 (3.3); 1.2275 (6.1);

- 60 042986

1.2248 (3.3); 1.2021 (8.5); 1.1992 (5.0); 1.1869 (8.4); 1.1839 (4.9); 1.0629 (0.6); 1.0432 (0.6); 1.0403 (0.5);

0.0079 (1.6); -0.0002 (54.8); -0.0085 (1.6).

Example No. I.1-81.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5311 (2.7); 7.5180 (2.7); 7.5118 (4.1); 7.4916 (1.8); 7.3745 (5.4); 7.3517 (5.4); 7.3093 (1.6); 7.2594 (297.8); 7.2136 (0.9); 6.9955 (1.6); 6.3558 (5.1); 6.3475 (5.4); 4.1135 (1.2);

4.0857 (2.7); 4.0666 (2.5); 4.0176 (2.3); 4.0013 (2.4); 3.9901 (2.4); 3.9772 (1.4); 3.9613 (0.9); 3.9427 (0.6);

3.9253 (1.6); 3.9068 (2.0); 3.8960 (1.8); 3.8879 (2.1); 3.8777 (1.6); 3.8699 (1.8); 3.5557 (16.0); 3.5111 (1.5);

3.4935 (2.1); 3.4817 (1.6); 2.8256 (2.4); 2.8090 (2.1); 2.7901(2.6); 1.9569 (5.4); 1.9482 (5.7); 1.6795 (1.9);

1.6640 (1.8); 1.6533 (1.6); 1.5497 (49.4); 1.5290 (13.9); 0.1467 (0.6); -0.0002 (129.8); -0.1494(0.7).

Example No. I.1-82.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5179 (1.1); 7.4941(2.9); 7.4756 (3.0); 7.3892 (3.7); 7.3666 (3.6); 7.2595 (165.1); 6.9954 (0.9); 6.3516 (6.1); 4.1319 (0.5); 4.1180 (0.8); 4.1045(1.1); 4.0908(1.3); 4.0744 (0.8);

4.0547 (1.6); 4.0419 (2.1); 4.0245(2.2); 3.9976 (1.4); 3.9690 (0.6); 3.9377 (1.6); 3.9213 (2.5); 3.9036 (1.9);

3.8870 (0.5); 3.5556 (16.0); 2.8500 (3.8); 2.8339 (6.8); 2.8171(5.2); 2.5355 (1.4); 2.5181 (1.8); 2.4916 (1.3);

2.4363 (0.9); 2.4180 (1.5); 2.4008 (1.3); 2.3827 (0.9); 2.0651 (1.0); 2.0502 (1.3); 2.0365 (1.4); 2.0204 (1.1);

1.6453 (1.4); 1.5544 (27.5); 1.5408 (13.6); 1.5226 (10.6); -0.0002 (71.3).

Example No. I.1-89.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5182 (2.0); 7.5134 (2.7); 7.5047(2.6); 7.4945 (2.7); 7.4861 (2.6); 7.3909 (5.0); 7.3682 (4.8); 7.3098 (0.6); 7.2595(347.3); 7.2263 (0.5); 7.2100 (0.7); 6.9954 (1.8); 6.3503 (4.3); 6.3446 (4.4); 4.7259 (1.4); 4.7202 (1.6); 4.7104 (2.8); 4.7062 (3.1); 4.6949 (1.7); 4.6906 (2.9); 4.6866 (1.8);

4.6753 (1.4); 4.3843 (2.1); 4.3689 (4.1); 4.3591 (1.5); 4.3534 (2.2); 4.3467 (2.7); 4.3435 (2.6); 4.3281 (1.4);

4.3121 (0.9); 4.3031 (0.8); 4.2948 (0.8); 4.2837 (1.6); 4.2749 (1.8); 4.2674 (1.7); 4.2584 (1.8); 4.2433 (1.7);

4.2392 (1.7); 4.2276 (1.8); 4.2236 (1.8); 4.2153 (0.8); 4.1956 (0.8); 3.9493 (0.6); 3.9346 (2.0); 3.9311 (2.4);

3.9168 (2.2); 3.9132 (2.2); 3.8990 (0.7); 3.5515 (12.5); 3.5487 (12.5); 3.1880 (1.0); 3.1724 (1.5); 3.1563 (0.9); 1.5667 (5.0); 1.5452 (16.0); 1.5274 (14.7); 1.2669 (0.8); 0.8820 (1.0); 0.1460 (0.6); 0.0080 (4.0); -0.0002 (126.5); -0.0084 (3.8); -0.1496 (0.6).

Example No. I.1-91.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5528 (1.1); 7.5434 (1.2); 7.5330 (2.3); 7.5265 (2.1); 7.5181 (1.8); 7.5083 (1.4); 7.3756 (1.9); 7.3656 (2.5); 7.3526 (2.2); 7.3431 (2.1); 7.3130 (0.8); 7.2595 (197.6); 7.2135 (1.0);

6.9954 (1.1); 6.3487 (7.2); 4.0925 (0.8); 4.0837 (0.9); 4.0641 (1.5); 4.0550 (1.8); 4.0285 (0.9); 4.0203 (0.9);

4.0092 (0.9); 3.9982 (1.5); 3.9819 (1.4); 3.9662 (2.0); 3.9615 (2.1); 3.9529(2.9); 3.9434 (3.2); 3.9258 (3.2);

3.9072 (2.1); 3.5538 (16.0); 3.4639 (0.8); 3.4354 (0.8); 3.3991 (1.7); 3.3722 (2.0); 3.3463 (0.9); 1.8363 (1.4);

1.5449 (26.8); 1.5223 (8.9); 1.5142 (7.9); 1.4866 (6.0); 1.4542 (2.1); 1.2517 (1.0); 1.2373 (1.0); -0.0002 (85.0).

Example No. I.1-92.

1H-NMR (400.0 MHz, CDCl3): δ= 7.5181 (1.6); 7.4892 (2.8); 7.4703 (2.8); 7.3852 (4.0); 7.3621(3.6); 7.2594 (272.3); 7.2084 (0.7); 7.1515 (0.6); 6.9953 (1.5); 6.3492 (7.7); 4.0194 (0.7); 4.0045 (0.7); 3.9914 (1.0);

3.9773 (1.1); 3.9379 (1.5); 3.9261 (2.0); 3.9099 (3.0); 3.8903 (3.0); 3.8588 (1.2); 3.8120 (3.2); 3.7833 (3.1);

3.5527 (16.0); 3.3939 (1.0); 3.3671 (1.5); 3.1633 (1.2); 3.1414 (2.0); 3.1126 (1.0); 1.8568 (1.1); 1.7483 (1.2);

1.7243 (1.3); 1.5854 (4.1); 1.5751 (4.6); 1.5470 (45.8); 1.5325 (14.5); 1.5145 (11.1); 1.2355 (1.0); 0.1470 (0.6);

-0.0002 (115.4); -0.1493 (0.5).

Example No. I.1-94.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5301 (1.6); 7.5254 (1.6); 7.5186 (1.7); 7.5162 (1.8); 7.5114 (1.7); 7.5067 (1.7); 7.4975 (1.7); 7.3653 (3.8); 7.3425 (3.8); 7.3095 (0.6); 7.2783 (0.5); 7.2759 (0.6); 7.2751 (0.7);

7.2743 (0.7); 7.2735 (0.8); 7.2727 (0.8); 7.2719 (1.0); 7.2711 (1.0); 7.2703 (1.2); 7.2695 (1.3); 7.2687 (1.5);

7.2679 (1.7); 7.2671 (1.9); 7.2663 (2.1); 7.2655 (2.5); 7.2647 (3.0); 7.2639 (4.0); 7.2630 (5.6); 7.2598 (228.0); 7.2549 (3.3); 7.2541 (2.4); 7.2533 (1.7); 7.2525 (1.2); 7.2517 (0.8); 7.2509 (0.6); 7.2501 (0.6); 7.2493 (0.6);

7.2485 (0.6); 6.9957 (1.3); 6.3491 (5.8); 5.0568 (0.6); 5.0518 (1.1); 5.0464 (0.7); 5.0407 (0.9); 5.0358 (1.2);

5.0297 (0.7); 5.0255 (0.9); 3.9219 (0.9); 3.9155 (0.9); 3.9040 (1.0); 3.8976 (1.1); 3.8943 (0.7); 3.8761 (2.1);

3.8581 (2.2); 3.8401 (0.6); 3.5522 (10.4); 3.4128 (0.6); 3.3966 (2.0); 3.3869 (1.3); 3.3813 (1.3); 3.3698 (3.4);

3.3545 (2.0); 3.3453 (0.6); 3.3407 (1.3); 3.3370 (1.8); 3.3297 (1.0); 3.3273 (1.0); 3.3063 (10.9); 3.3039 (11.5); 3.2975 (16.0); 3.2950 (15.8); 3.2905 (1.5); 3.2856 (1.3); 3.2800 (1.1); 3.2755 (1.2); 3.2635 (0.7); 3.2589 (0.8); 3.2534 (0.7); 3.2486 (0.8); 2.0223 (0.6); 1.5634 (6.4); 1.5379 (5.7); 1.5356 (6.0); 1.5319 (4.4); 1.5296 (4.3);

1.5200 (5.6); 1.5177 (5.8); 1.5140 (4.2); 1.5118 (4.0); 1.2572 (0.5); 1.2408 (0.8); 1.2244 (0.6); 1.1974 (5.6);

1.1937 (5.8); 1.1812(5.5); 1.1775 (5.7); 1.1180 (7.3); 1.1018 (7.3); 0.2376 (0.6); 0.1262 (0.8); 0.0079 (2.9);

0.0063 (1.0); 0.0054 (1.1); 0.0046 (1.3); -0.0002 (93.0); -0.0052 (1.4); -0.0060 (1.1); -0.0068 (0.9); -0.0085 (2.6).

Example No. I.1-115.

1H-NMR (400.0 MHz, CDCl3): δ = 7.8084 (0.6); 7.5230 (4.8); 7.5183 (2.4); 7.5153 (4.8); 7.5092 (0.9); 7.5042 (4.8); 7.4965 (4.6); 7.4017 (9.3); 7.3790 (9.4); 7.3597 (0.9); 7.3085 (1.1); 7.2595 (339.3); 6.9955 (1.9); 6.3673 (0.7); 6.3552 (7.8); 6.3496 (7.6); 5.3758 (0.6); 5.3679 (1.4); 5.3647(1.7); 5.3599 (1.6); 5.3519 (2.9); 5.3471 (3.1); 5.3389 (1.6); 5.3345 (1.9); 5.3313 (1.6); 5.3233 (0.8); 4.8455 (2.8); 4.8293 (4.9); 4.8127 (4.3);

- 61 042986

4.7994 (1.6); 4.5397 (1.6); 4.5271 (3.1); 4.5249 (3.1); 4.5204 (1.6); 4.5147 (1.8); 4.5077 (2.9); 4.4915 (3.0);

4.4811 (2.9); 4.4713 (2.2); 4.4591 (1.4); 3.9656 (1.2); 3.9558 (1.1); 3.9476 (3.7); 3.9380 (3.9); 3.9298 (3.8);

3.9201 (4.0); 3.9121 (1.1); 3.9023 (1.2); 3.5543 (16.0); 3.5495 (13.0); 2.0790 (0.9); 2.0688 (1.2); 2.0047 (3.4);

1.5836 (3.5); 1.5508 (25.8); 1.5329 (25.1); 0.3306 (0.6); 0.1573 (0.6); 0.0080 (3.5); -0.0002 (134.8); -0.0085 (4.5).

Example No. I.1-117.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5259 (0.6); 7.5186 (0.6); 7.5072 (0.6); 7.4956 (0.6); 7.4870 (0.6);

7.4826 (0.6); 7.4769 (0.6); 7.4684 (0.6); 7.4640 (0.6); 7.4392 (1.1); 7.4329 (0.7); 7.4163 (1.0); 7.4104 (0.7);

7.2597 (104.1); 6.9957 (0.6); 6.3581 (1.0); 6.3453 (1.6); 6.3306 (1.0); 5.2985 (8.4); 3.9819 (0.6); 3.9787 (0.6); 3.9687 (0.6); 3.9641 (0.7); 3.9613 (0.9); 3.9508 (0.6); 3.9441 (1.0); 3.9357 (1.0); 3.9211 (0.8); 3.5511 (5.3);

3.5487 (5.1); 2.8421 (0.5); 2.1697 (1.1); 2.0958 (0.5); 2.0862 (0.6); 1.5467 (2.1); 1.5352 (16.0); 1.5292 (3.0);

1.5218 (3.5); 1.5174 (2.1); 0.0080 (1.3); -0.0002 (40.8); -0.0085 (1.4).

Example No. I.1-123.

1 H-NMR (400.0 MHz, CDCl ₃ ): δ = 7.5966 (0.8); 7.5854 (0.8); 7.5779 (0.9); 7.5665 (0.9); 7.5255 (0.9); 7.5216 (1.2); 7.5183 (1.8); 7.5071 (0.9); 7.5031 (1.0); 7.3788 (1.7); 7.3703 (1.2); 7.3561 (1.7); 7.3477 (1.1); 7.2930 (0.6); 7.2593 (294.4); 6.9954 (1.6); 6.3536(2.2); 6.3470 (2.8); 3.9044 (0.7); 3.8941 (0.7); 3.8865 (0.7);

3.8762 (0.8); 3.8534 (0.7); 3.8459 (0.8); 3.8353 (0.7); 3.8282 (0.8); 3.5519 (7.0); 3.0675 (0.6); 3.0488 (0.7);

3.0371 (0.9); 3.0189 (0.6); 2.8549 (1.9); 2.8464 (1.3); 2.8428 (1.2); 2.8346 (1.9); 2.8257(1.3); 2.8052 (1.0);

2.7905 (0.5); 2.7743 (0.6); 1.5551 (3.6); 1.5477 (4.5); 1.5367 (16.0); 1.5134 (4.3); 1.2655 (1.1); 0.8988 (0.6);

0.8819 (1.6); 0.8641 (0.6); 0.0079 (3.7); -0.0002 (107.4); -0.0085 (4.1).

Example No. I.1-126.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5920 (2.0); 7.5867 (1.9); 7.5736 (1.9); 7.5181 (2.0); 7.5107 (1.2); 7.4945 (2.0); 7.4761 (1.4); 7.3759 (3.3); 7.3532(3.6); 7.2594 (316.3); 7.2141 (0.7); 6.9955 (1.8); 6.3441 (10.1); 4.7357 (1.6); 3.9424 (2.3); 3.9244 (3.0); 3.9096 (1.8); 3.6768 (1.3); 3.6471 (2.2); 3.6068 (2.5); 3.5905 (3.6); 3.5715 (4.9); 3.5506 (16.0); 3.5289 (6.2); 3.4839 (0.8); 3.4396 (0.9); 3.4249 (0.6); 1.8265 (1.6); 1.8031 (1.6); 1.7739 (2.0); 1.7149 (1.4); 1.5630 (9.0); 1.5470 (55.4); 1.5208 (10.0); 0.1458 (0.7); -0.0002 (137.6); -0.1497 (0.7).

Example No. I.1-132.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5182 (1.4); 7.5010 (2.2); 7.4896 (2.3); 7.4827 (2.3); 7.4715 (2.1); 7.3819 (3.6); 7.3591(3.8); 7.3124 (1.6); 7.2594 (213.2); 7.2153 (1.1); 6.9956 (1.1); 6.3504 (7.4); 4.7940 (1.4);

4.7811 (1.5); 3.9550 (1.0); 3.9373 (3.0); 3.9193 (3.0); 3.9020 (1.0); 3.5544 (16.0); 2.7431 (0.8); 2.7181 (1.9);

2.6910 (2.2); 2.5674 (2.0); 2.5412(2.4); 2.5096 (1.5); 2.1702 (0.5); 2.0291 (1.2); 2.0198 (1.1); 2.0070 (1.5);

1.9725 (0.9); 1.9404 (1.3); 1.9205 (1.1); 1.8450 (0.7); 1.8253 (1.3); 1.8131 (1.0); 1.8012 (1.2); 1.7709 (0.8);

1.7230 (1.2); 1.5587 (29.7); 1.5392 (14.2); 1.5214 (12.4); 0.0528 (0.7); -0.0002 (92.1); -0.0454 (0.6).

Example No. I.1-142.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5184 (1.3); 7.4905 (2.1); 7.4812 (2.2); 7.4720 (2.2); 7.4627(2.2); 7.4273 (2.2); 7.4205(2.2); 7.4048 (2.2); 7.3979 (2.2); 7.3096 (0.6); 7.2595(226.6); 7.2254 (0.8); 6.9955 (1.3); 6.3472 (3.7); 6.3422(3.6); 5.2984 (12.2); 4.9774 (1.2); 3.9975 (0.6); 3.9796 (2.0); 3.9769 (1.9); 3.9617 (2.0);

3.9590 (1.9); 3.9440 (0.6); 3.5489 (10.1); 3.0588 (0.6); 3.0466 (0.6); 3.0242 (1.4); 3.0099 (1.1); 3.0000 (1.1);

2.9869 (1.0); 2.9305 (0.9); 2.8930 (1.2); 2.8673 (0.5); 2.8547 (0.5); 2.2702 (0.8); 2.2610(1.2); 2.2445 (1.8);

2.2342 (1.8); 2.2057 (0.6); 2.1947 (1.0); 2.1836 (1.5); 2.1695 (4.0); 2.1586 (1.3); 1.5737 (6.8); 1.5695 (6.8);

1.5558 (7.3); 1.5516 (7.4); 1.5356 (16.0); 0.0079 (3.3); -0.0002 (88.9); -0.0085 (3.5).

Example No. I.1-151.

1H-NMR (400.0 MHz, CDCl3): δ = 7.3604 (2.4); 7.3586 (2.3); 7.3379 (2.4); 7.3361 (2.3); 7.2630 (22.6); 7.2368 (1.9); 7.2187 (1.9); 7.2114 (1.9); 7.1932 (1.9); 6.7339 (0.5); 6.3406(3.2); 6.3333 (3.2); 3.8154 (1.4);

3.8079 (1.4); 3.7973 (1.4); 3.7897 (1.4); 3.5487 (4.7); 3.5456 (6.0); 3.5422 (6.1); 3.5390 (4.8); 3.4893 (1.0);

3.4764 (1.1); 3.4388 (0.6); 3.4239 (0.5); 3.4159 (0.8); 3.4098 (0.8); 3.4057 (0.6); 3.3974 (0.6); 3.3916 (0.6);

3.3854 (0.6); 3.3806 (1.2); 3.3668 (1.6); 3.3581 (0.7); 3.3563 (0.7); 3.3499 (1.1); 3.3469 (1.0); 3.3411 (1.3);

3.3251 (1.2); 3.3223 (0.9); 3.3112 (1.7); 3.3082 (1.5); 3.3053 (1.0); 3.2987 (1.5); 3.2917 (1.1); 3.2482 (16.0); 3.2424 (15.6); 2.9549 (1.0); 2.8831 (0.8); 1.6180 (1.5); 1.6002 (5.8); 1.5967 (6.0); 1.5820 (5.8); 1.5785 (5.9); -0.0002 (8.3).

Example No. I.1-180.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5182 (3.6); 7.3517 (1.1); 7.3442(2.5); 7.3320 (3.1); 7.3156 (5.2); 7.3092 (4.5); 7.2941 (7.2); 7.2903(7.2); 7.2766 (4.7); 7.2593(628.6); 7.2325 (0.6); 7.1698 (1.8); 7.1518 (2.0); 7.1418 (2.0); 7.1237 (1.9); 6.9953 (4.0); 6.3321 (3.4); 6.3235 (3.2); 4.4545 (5.6); 4.4451 (5.7); 3.7489 (1.6);

3.7334 (1.6); 3.7120 (0.6); 3.5363 (5.1); 3.5335 (5.1); 3.5249 (5.1); 3.5221 (4.8); 3.4862 (0.8); 3.4815 (1.0);

3.4687 (1.5); 3.4567 (1.7); 3.4430 (0.9); 3.4358 (0.9); 3.3465 (1.6); 3.3321 (2.2); 3.3165 (1.8); 3.3014 (0.8);

1.7126 (1.6); 1.5514 (16.0); 1.5474 (13.1); 1.5331 (7.9); 1.5291 (7.2); 0.1460 (0.9); 0.0846 (0.7); 0.0496 (1.2);

0.0079 (8.1); -0.0002 (232.9); -0.0084 (8.3); -0.1497 (0.9).

Example No. I.1-181.

1 H-NMR (400.0 MHz, d6-DMSO): δ = 8.2272 (0.6); 7.8121 (1.4); 7.7883 (1.5); 7.6150 (0.8); 7.6036 (0.8);

- 62 042986

7.5961 (0.8); 7.5847 (0.7); 6.6143 (1.5); 6.6049 (1.4); 3.9203 (0.7); 3.9036 (0.7); 3.4277 (2.8); 3.4247 (2.8);

3.3787 (6.5); 3.2158 (1.0); 3.1992 (1.0); 2.6693 (0.6); 2.5556 (0.6); 2.5509 (0.6); 2.5227 (2.1); 2.5181 (2.9);

2.5093 (32.0); 2.5048 (66.7); 2.5002 (92.3); 2.4956 (64.0); 2.4910 (29.3); 2.4733 (0.9); 2.4629 (1.4); 2.4550 (1.8); 2.4461 (0.9); 2.4369 (0.5); 2.3270 (0.5); 2.0451 (0.9); 2.0405 (0.9); 2.0278 (16.0); 1.3933 (2.6); 1.3760 (2.6); -0.0002 (6.3).

Example No. I.1-221.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5185 (2.2); 7.3604 (2.6); 7.3575(2.7); 7.3494 (3.2); 7.3467 (3.0);

7.3378 (2.8); 7.3349 (2.9); 7.3268 (3.1); 7.3241 (3.1); 7.3201 (2.5); 7.3018 (2.4); 7.2921 (2.9); 7.2738 (3.6);

7.2596 (403.9); 7.2444 (4.0); 7.2280 (2.2); 7.2096 (3.0); 7.2023 (2.4); 7.1844(2.3); 6.9957(2.3); 6.7335 (1.3)

6.3348 (9.2);

3.8317 (3.4);

3.7778 (1.0);

3.6533 (1.5);

3.4698 (1.0);

3.4187 (0.9);

3.1970 (0.9);

3.1156 (1.0);

1.9298 (0.6);

1.8082 (1.4);

6.3301 (4.8); 3.8860 (0.8); 3.8797 (0.9); 3.8700 (1.1); 3.8612 (1.2); 3.8429 (2.0);

3.8244 (3.9); 3.8191 (2.9); 3.8138 (3.5); 3.8062(3.6); 3.8010 (2.7); 3.7948 (2.4);

3.7717 (0.6); 3.7507 (0.9); 3.7377 (1.5); 3.7199 (1.3); 3.7048 (1.1); 3.6884 (2.2);

3.6347 (0.7); 3.5429 (16.0); 3.5118 (0.6); 3.5035 (0.8); 3.4956 (1.0); 3.4879 (0.8);

3.4614 (1.2); 3.4534 (1.5); 3.4446 (1.2); 3.4384 (0.8); 3.4337 (0.7); 3.4292 (0.7);

3.4143 (0.8); 3.4090 (1.1); 3.4042 (0.9); 3.3993 (0.8); 3.3951 (0.7); 3.2932 (0.6);

3.1830 (0.9); 3.1690 (0.7); 3.1652 (0.7); 3.1486 (0.7); 3.1339 (1.0); 3.1289 (0.7);

3.1103 (0.7); 3.0983 (1.1); 3.0865 (0.6); 3.0818 (0.8); 3.0760 (0.6); 3.0637 (0.6);

1.9133 (0.8); 1.8966 (1.1); 1.8768 (2.0); 1.8632 (3.2); 1.8466 (3.6); 1.8299 (2.3);

1.7885 (1.3); 1.7699 (1.1); 1.7455 (1.2); 1.7376 (1.4); 1.7212 (1.4); 1.6105 (7.7);

3.8370 (1.7);

3.7881 (1.3);

3.6706 (2.5);

3.4779 (0.8);

3.4229 (0.8);

3.2111 (0.7);

3.1209 (0.7);

2.0049 (6.1);

1.8193 (1.7);

1.6056 (7.9);

1.5925 (11.0); 1.5887 (11.1); 1.5758 (7.3); 1.5709 (7.2); 1.4915 (0.6); 1.4743 (0.8); 1.4493 (2.0); 1.4435 (1.6);

1.4361 (0.7); 1.4257(1.1); 1.3507 (0.5); 1.3390 (0.8); 1.3301 (0.8); 1.3212 (0.9); 1.3120 (0.9); 0.1461 (0.6);

0.0080 (4.6); -0.0002 (146.7); -0.0085 (5.7); -0.1497 (0.5).

Example No. I.1-222.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5209 (0.6); 7.4303 (4.1); 7.4120 (4.0); 7.3730 (3.7); 7.3694 (3.3); 7.3505 (3.8); 7.3468 (3.2); 7.2621 (97.4); 6.9980 (0.5); 6.3663 (4.8); 6.3577 (4.0); 3.7016 (16.0); 3.6618 (5.5); 3.6482 (10.5); 3.5606 (8.9); 3.5500 (11.6); 3.4938 (1.6); -0.0002 (27.1).

Example No. I.1-224.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5181 (9.0); 7.3541 (3.7); 7.3396 (3.5); 7.3365 (4.1); 7.3316 (3.8);

7.3172 (3.5); 7.3142 (3.4); 7.3090 (1.3); 7.2936 (2.5); 7.2887 (1.2); 7.2755 (5.9); 7.2592 (1610.0); 7.2327 (3.2); 7.2269 (2.2); 7.2085 (1.3); 7.2006 (0.9); 7.1809 (2.7); 7.1631 (2.5); 7.1547(2.9); 7.1370 (2.9); 7.1095 (0.7);

6.9952 (9.0); 6.8058 (1.0); 6.7098 (0.9); 6.3363 (9.4); 6.3286 (5.2); 3.8605 (2.1); 3.8521 (2.2); 3.8421 (2.4);

3.8374 (2.3); 3.8336 (2.8); 3.8246 (2.1); 3.8192 (2.3); 3.8089(3.9); 3.7915 (3.8); 3.7876 (3.1); 3.7750 (2.4);

3.7700 (2.2); 3.7545 (1.0); 3.6924 (0.9); 3.6748 (1.8); 3.6607 (1.8); 3.6396 (1.5); 3.5446 (14.4); 3.5383 (14.2); 3.5351 (9.6); 3.3360 (1.0); 3.3205 (1.0); 3.3068 (1.9); 3.2910 (2.0); 3.2862 (1.7); 3.2725(2.2); 3.2572 (4.7);

3.2414 (2.7); 3.2322 (2.1); 3.2278 (2.0); 3.2192 (2.0); 3.2144 (2.1); 3.1979 (1.1); 3.1937 (1.2); 3.1852 (1.1);

3.1806(1.2); 2.0047 (1.0); 1.9330 (1.0); 1.9132(1.2); 1.8977 (1.5); 1.8794 (1.6); 1.8615 (1.5); 1.6739 (1.8);

1.6553 (2.8); 1.6470 (2.2); 1.6265 (10.7); 1.6216 (9.6); 1.6083 (10.7); 1.6039 (13.5); 1.6007 (10.3); 1.5864 (8.9);

1.5824 (8.7); 1.5378 (51.6); 1.4866 (1.7); 1.4655 (1.3); 1.1149 (15.4); 1.1110 (16.0); 1.0587 (13.3); 1.0517 (13.3); 0.1460 (1.9); 0.0340 (0.9); 0.0079 (17.2); -0.0002 (597.4); -0.0085 (18.7); -0.1498 (2.1).

Example No. I.1-227.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5182 (1.1); 7.4992 (1.8); 7.4891 (1.8); 7.4803 (1.8); 7.4705 (1.8); 7.3781 (3.4); 7.3553 (3.2); 7.3148 (0.6); 7.2595 (177.5); 7.2132 (0.8); 6.9955 (1.0); 6.3498 (5.8); 4.8970 (1.0); 4.8868 (1.3); 4.8764 (1.1); 3.9641 (0.8); 3.9461 (2.5); 3.9284 (2.6); 3.9113 (0.9); 3.8431 (1.1); 3.8164 (2.1); 3.7886 (1.4); 3.5528 (13.3); 3.5149 (1.7); 3.4911(2.5); 3.4626 (1.4); 1.8719 (0.8); 1.8465 (1.0); 1.7559(1.1); 1.6113 (16.0); 1.5405 (10.3); 1.5227(10.4); 1.4937 (1.2); 1.4743 (1.0); 1.4598 (0.8); -0.0002 (76.1).

Example No. I.1 -241.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5185 (1.4); 7.3553 (5.1); 7.3328 (5.1); 7.3093 (1.3); 7.2733 (7.2); 7.2596(233.2); 7.2135 (1.0); 7.1941 (2.1); 7.1763 (0.9); 6.9955 (1.3); 6.9223 (0.7); 6.7481 (1.3); 6.3368 (7.6); 3.9230 (1.2); 3.8965 (1.4); 3.8472 (1.8); 3.8266 (3.2); 3.8086 (2.7); 3.7907 (1.7); 3.5429 (16.0); 3.4835 (0.8); 3.4256 (0.9); 3.3906 (1.6); 3.3627 (1.3); 3.2808 (1.3); 3.1977 (0.9); 3.1730 (1.0); 3.0580 (0.6); 3.0462 (0.9); 3.0268 (1.2); 3.0120 (1.2); 2.9457 (0.6); 2.9137 (0.8); 1.7080 (6.4); 1.5959 (11.4); 1.5777 (11.1); 1.4638 (7.3); 1.1952 (0.7); 1.1670 (0.6); 1.0793 (0.8); 0.0495 (0.6); -0.0002 (98.6); -0.1489 (0.5).

Example No. I.1-271.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5210 (0.9); 7.3722 (9.6); 7.3690 (4.8); 7.3497 (9.7); 7.3466 (4.6);

7.2766 (0.5); 7.2693 (1.4); 7.2620 (147.4); 7.2554 (4.4); 7.2435 (4.0); 7.2372 (4.0); 7.2254 (3.9); 7.2132 (4.0);

7.1951 (3.9); 7.1748 (3.5); 7.1568 (3.5); 6.9980 (0.8); 6.5734 (0.9); 6.5584 (1.5); 6.5408 (1.8); 6.3483 (8.5);

6.3410 (6.4); 6.3339 (5.7); 4.4303 (0.6); 4.4219 (1.3); 4.4098 (1.9); 4.4031 (2.4); 4.3969 (2.2); 4.3908 (2.4);

4.3835 (1.7); 4.3721 (1.1); 3.8823 (0.7); 3.8748 (0.6); 3.8596 (1.2); 3.8422 (1.4); 3.8348 (1.4); 3.8239 (1.0);

3.8166 (1.0); 3.8112 (1.0); 3.8070 (1.0); 3.8037 (1.0); 3.7930 (3.4); 3.7890 (3.5); 3.7855 (3.1); 3.7783 (6.0);

3.7752 (4.5); 3.7708 (3.8); 3.7672 (3.7); 3.7651 (3.2); 3.7626 (3.3); 3.7600 (5.3); 3.7546 (5.6); 3.7524 (4.6);

3.7439 (4.3); 3.7411 (6.8); 3.7388 (8.2); 3.7304 (6.1); 3.7240(3.6); 3.7175 (6.1); 3.7117 (2.5); 3.7063 (3.1);

- 63 042986

3.7032(2.4); 3.6975 (1.9); 3.6934 (1.1); 3.6816 (0.6); 3.5687 (1.6); 3.5617 (2.0); 3.5548 (9.0); 3.5517 (12.3);

3.5486 (14.4); 3.5456 (15.3); 3.5434 (14.7); 3.5403 (16.0); 3.5382 (13.9); 3.5351 (10.5); 3.5250 (1.3) (1.2) (0.8) (1.6) (1.2) (1.0) (1.7)

3.5090 (1.5)

2.2220 (0.6)

2.1590 (1.6)

2.1043 (0.6)

1.6738 (1.2)

3.5015 (2.6) 2.2159 (0.7) 2.1558 (1.7) 2.0051 (8.9) 1.6712 (1.2)

3.4930 (1.5)

2.2099 (1.3)

2.1534 (1.6)

1.8061 (2.2)

1.6680 (1.2)

3.4850 (1.2)

2.2035 (0.8)

2.1434 (1.3)

1.7015 (0.7)

1.6596 (1.8)

3.4773 (2.0)

2.1924 (1.8)

2.1408 (1.7)

1.6931 (0.8)

1.6517 (1.5)

3.4693 (1.1)

2.1764 (1.9)

2.1381 (1.2)

1.6870 (0.8)

1.6493 (1.5)

2.2303 (0.7)

2.1742 (2.2)

2.1225 (1.7)

1.6847 (0.8)

1.6455 (1.6)

1.6387 (1.6); 1.6330 (1.4); 1.6263 (1.5); 1.6186 (1.2); 1.6119 (0.8); 1.5956 (11.7); 1.5925 (13.2);

3.5180 2.2264 2.1705 2.1201

1.6791 1.6408

1.5857 (14.8); 1.5840 (14.9); 1.5775 (12.1); 1.5743 (13.0); 1.5676 (14.1); 1.5659 (13.9); 0.0080 (1.7); -0.0002 (62.9);

-0.0085 (1.8).

Example No. I.1-275.

1 H-NMR (400.0 MHz, d6-DMSO): δ = 8.5920 (2.3); 8.5750 (2.3); 8.5121 (4.5); 8.4952 (4.7); 8.1667 (0.6)

7.8379 (7.0) 7.5547 (4.2) 5.4346 (0.5) 3.9138 (1.3) 3.7251 (2.5) 3.3302 (3.4)

3.2018 (2.9) 3.0921 (2.8) 2.8463 (1.5) 2.7265 (1.6)

7.8300 (6.0); 7.8257(6.2); 7.8140 (7.1); 7.8062 (5.9); 7.8020 (5.9); 7.6412 (9.2);

7.5359 (4.3); 7.4605 (4.5); 7.4419 (4.6); 6.6232 (9.5); 6.6102 (10.1); 6.5991 (10.2);

4.3828 (3.4); 4.3662 (3.1); 4.3485 (1.6); 4.2309 (0.5); 4.1917 (0.5); 3.9383 (1.0) 3.9037 (4.5); 3.8967(3.9); 3.8869 (5.0); 3.8793 (4.0); 3.8693 (5.0); 3.8500 (3.9) 3.4269 (33.0); 3.3945 (1.9); 3.3840 (2.0); 3.3738 (2.8); 3.3625 (2.5); 3.3508(2.8); 7.6223(9.2); 6.5745 (8.9)

3.3196 (1.8)

3.1903 (2.6)

3.0827 (1.6)

2.8361 (1.5)

2.7196 (1.5)

3.3108 (1.9)

3.1639 (1.4)

3.0714 (0.8)

2.8301 (1.4)

2.7108 (1.4)

3.2959 (2.0)

3.1433 (3.1)

3.0642 (0.8)

2.8190 (1.4)

2.7020 (1.4)

3.2766 (1.8)

3.1237 (3.0)

2.8798 (1.6)

2.7602 (1.6)

2.6788 (0.8)

3.2354 (2.3); 3.2227 (2.6) 3.1134 (3.3); 3.1059 (2.2) 2.8707 (1.8); 2.8628 (1.6) 2.7527 (1.6); 2.7450 (1.7)

2.6742 (1.6); 2.6695 (2.3)

3.9211 (3.6) 3.8326 (1.3) 3.3403 (3.0)

3.2111 (2.8)

3.0988 (2.1) 2.8523 (1.7)

2.7359 (1.5)

2.6648 (1.6)

2.5505 (1.4); 2.5230 (8.0); 2.5183 (11.2); 2.5096(132.9); 2.5050(280.5); 2.5004 (387.5); 2.4959 (269.5) 2.4913 (124.7); 2.4557 (1.6); 2.4511 (1.6); 2.3934 (0.8); 2.3764 (1.1); 2.3577 (1.6); 2.3320 (3.4); 2.3271 (3.7) 2.3226 (3.5); 2.3182 (3.2); 2.2996 (2.5); 2.2921 (1.7); 2.2854 (2.1); 2.2764 (1.7); 2.2583 (1.2); 2.2431 (0.6) 2.0721 (10.6); 2.0646 (0.7); 2.0447 (1.5); 2.0253 (1.5); 2.0161(1.6); 1.9936 (1.8); 1.9812 (2.3); 1.9618 (2.7)

1.9444 (2.3); 1.9253 (1.6); 1.9099 (1.2); 1.4221 (11.9); 1.4080 (13.9); 1.4047 (15.9); 1.4000 (16.0); 1.3956 (15.4); 1.3908 (13.6); 1.3826 (14.2); 1.3783 (13.0); 1.2705 (0.5); 1.2527 (1.2); 1.2349 (0.7); 1.1612 (1.1); 1.1435 (0.6); 0.0080 (4.7); -0.0002 (168.4); -0.0085 (5.5).

Example No. I.1-276.

1H-NMR (400.0 MHz, CDCI3): δ = 7.5187 (2.0); 7.3627 (5.7); 7.3403 (5.8); 7.2595 (306.4); 7.2057 (2.1); 7.1626 (0.8); 6.9952 (1.7); 6.7496 (1.8); 6.3370 (6.7); 3.8891 (2.5); 3.8386 (2.5); 3.8230 (3.1); 3.8049 (2.1); 3.6435 (3.6); 3.6145 (4.8); 3.5373 (16.0); 3.3089 (1.8); 3.2946 (1.7); 3.2802 (1.6); 1.7587 (15.0); 1.6054 (14.6); 1.5873 (14.5); 1.5571 (4.4); 1.5387 (3.5); 1.4486 (1.1); 0.1441 (0.7); -0.0002 (130.4); -0.0539 (1.0); -0.1484 (0.7).

Example No. I.1-331.

1H-NMR (400.0 MHz, CDCl·,): δ = 7.5183 (1.7); 7.3706 (4.3); 7.3484 (4.4); 7.3141 (1.1); 7.2596 (282.3)

7.2140 (2.3); 7.1995 (1.7); 6.9957 (1.6); 6.8010 (0.8); 6.6923 (1.2); 6.3433 (7.3); 3.8646(0.8)

3.8303 (3.0); 3.8127 (1.8); 3.7504 (1.0); 3.7183 (2.9); 3.6879 (4.4); 3.6618 (5.9); 3.6412(4.8)

3.5485 (16.0); 3.4991 (2.0); 3.4750 (1.5); 3.4477 (1.1); 3.4087 (1.2); 3.3932 (1.5); 3.3579 (1.2) 3.2593 (0.9); 3.2501 (0.8); 3.2338 (1.1); 3.2245 (1.1); 3.1960 (0.7); 3.1528 (1.5); 3.1435(1.4)

3.1015 (1.4); 3.0899 (1.6); 3.0704 (1.2); 3.0578 (1.1); 3.0387 (0.9); 3.0236 (0.7); 3.0060(0.6)

1.6064 (8.8); 1.6010 (10.0); 1.5886 (8.8); 1.5828 (9.5); 0.1462 (0.6); -0.0002 (122.0); -0.1489 (0.6).

3.8471 (2.3)

3.5946 (1.6)

3.3487 (1.1)

3.1229 (2.2)

1.7893 (6.1) (4.1) (3.4) (1.4) (1.7) (1.3) (1.7) (3.4) (0.6) (0 ,5)

Example No. I.1-333.

Diastereomer 1 - 1H-NMR (400.0 MHz, CDCI3): δ = 7.5190 (1.6); 7.3798 (4.2); 7.3780 (4.1) 7.3700 (3.4); 7.3574 (4.2); 7.3557(4.2); 7.3517(4.2); 7.3478 (3.4); 7.3097 (0.5); 7.2944 (0.6) 7.2601 (295.8); 7.2436 (3.2); 7.2070 (3.0); 7.1892 (5.6); 7.1714 (2.7); 6.9961 (1.6); 6.8738 (0.9)

6.3514 (4.9)

4.4388 (2.0)

4.1426 (1.1)

4.0883 (2.0)

4.0160 (2.2)

3.8470 (2.6)

6.3468 (5.3)

4.4325 (1.8)

4.1362 (1.1)

4.0736 (1.1)

4.0092 (1.9)

3.8286 (4.2)

6.3364 (5.3)

4.4269 (2.6)

4.1253 (1.3)

4.0673 (1.0)

4.0040 (2.4)

3.8103 (3.0)

6.3287 (5.5)

4.4138 (2.6)

4.1176 (2.6)

4.0576 (1.9)

3.9983 (2.6)

3.7986 (2.4)

4.4755 (0.8)

4.4071 (2.4)

4.1127 (1.7)

4.0488 (2.7)

3.9879 (1.0)

3.7945 (2.2)

4.4676 (0.8)

4.3991 (1.5)

4.1004 (1.5)

4.0385 (3.2)

3.9798 (0.9)

3.7801 (2.2)

4.4566 (1.5)

4.3891 (1.2) 4.0970 (1.4)

4.0288 (3.1)

3.9693 (0.8)

3.7624 (0.7)

3.6259 (0.7); 3.6022 (0.9); 3.5851 (1.0); 3.5710 (1.2); 3.5431 (16.0); 3.5373 (11.9); 3.5340 (11.1) (10.2); 3.4965 (0.7); 3.4826 (0.9); 3.4646 (0.7); 3.4513 (0.6); 3.4384 (0.8); 3.4198 (0.8) (0.9) (5.8) (0.5) (1.0) (1.5) (2.4)

3.3776 (0.9)

3.1626 (5.5)

2.7364 (0.5)

2.0227 (0.8)

1.8949 (1.4)

3.3590 (1.1)

3.1540 (6.1)

2.1212 (0.5)

1.9712 (0.7)

1.8809 (0.9)

3.3431 (1.4)

3.1444 (7.2)

2.1105 (0.9)

1.9511 (2.0)

1.7487 (0.7)

3.3256 (1.2)

3.1374 (5.5)

2.0909 (1.3)

1.9380 (1.9)

1.7432 (0.8)

3.3094 (0.8) 3.1306 (1.9) 2.0842 (1.3)

1.9324 (2.5) 1.7389 (2.5)

3.2903 (0.6) 3.1242 (1.5) 2.0726 (1.6) 1.9187 (1.8)

1.7311 (0.7)

3.4066 (0.6) 3.1851 (0.6) 3.1190 (2.5) 2.0604 (1.5)

1.9137 (2.0) 1.7256 (0.8)

7.3740 7.2810 6.8310

4.4489 4.3804 4.0938

4.0241 3.8650 3.6491

3.5315 3.3967 3.1672 3.0880 2.0350

1.9002

1.7214

1.6147 (15.3); 1.6015 (14.0); 1.5965 (16.4); 1.5835 (12.5); 1.2552 (3.3); 0.8819 (0.8); 0.0079 (2.6);

- 64 042986

-0.0002 (85.0); -0.0085 (2.7). Diastereomer 2 - 1H-NMR (400.0 MHz, CDC13): δ = 7.5186 (2.9); 7.3809 (3.6);

7.3775 (5.4); 7.3715 (3.4); 7.3585 (4.0); 7.3552 (5.6); 7.3493 (3.2); 7.3092 (3.5); 7.2908 (2.0); 7.2718 (6.8); 7.2597 (481.0); 7.2514 (4.8); 7.2326 (4.2); 7.2097 (5.5); 7.2038 (4.6); 7.1857 (4.3); 7.1652 (3.0); 6.9957 (2.8); 6.7862 (0.8); 6.7723 (1.0); 6.7067 (0.9); 6.3508 (4.7); 6.3464 (4.8); 6.3390 (5.0); 6.3320 (5.0); 4.4773 (0.7);

4.4690 (0.6); 4.4508(1.5); 4.4382 (1.8); 4.4291 (1.9); 4.4190 (1.6); 4.4111 (2.7); 4.4014 (2.2); 4.3937 (1.6);

4.3843 (1.6); 4.1443 (0.8); 4.1373 (0.8); 4.1267 (0.9); 4.1187 (1.8); 4.1020 (0.9); 4.0945 (1.5); 4.0896 (1.4);

4.0750 (0.8); 4.0683 (1.0); 4.0591 (2.2); 4.0489 (2.0); 4.0428 (3.4); 4.0314 (3.9); 4.0193 (2.7); 4.0104 (2.4);

3.9995 (2.0); 3.9944 (1.1); 3.9901 (0.9); 3.9758 (0.8); 3.8401 (0.7); 3.8220 (2.0); 3.8062 (2.6); 3.7892 (3.1);

3.7723 (3.4); 3.7545 (2.5); 3.7362 (0.7); 3.6119 (0.6); 3.5977 (1.0); 3.5767 (1.3); 3.5459 (16.0); 3.5430 (14.9); 3.5008 (2.9); 3.4831 (2.8); 3.4656 (1.5); 3.4478 (0.7); 3.4289 (1.0); 3.4112 (0.9); 3.3963 (0.9); 3.3832 (1.0);

3.3644 (1.1); 3.3552(1.1); 3.3425 (1.3); 3.3364 (1.3); 3.3299 (1.0); 3.3234 (1.3); 3.3078 (0.9); 3.2887 (0.8);

3.1848 (0.6); 3.1660 (5.5); 3.1625 (5.6); 3.1534 (5.7); 3.1449 (7.7); 3.1381 (5.1); 3.1301 (1.8); 3.1234 (1.7);

3.1195 (2.5); 3.0883 (0.7); 2.3954 (2.0); 2.1167 (0.7); 2.0980 (1.0); 2.0844 (1.3); 2.0686 (1.5); 2.0607(1.4);

2.0487 (1.4); 2.0379 (1.3); 1.9693 (0.8); 1.9500 (1.8); 1.9307 (2.0); 1.9128 (2.0); 1.8938 (1.3); 1.8775 (0.8);

1.6103 (12.0); 1.5992 (9.6); 1.5970 (10.1); 1.5921 (12.8); 1.5811(8.9); 1.5789 (8.7); 1.5496 (1.3); 1.5314 (1.0); 1.4320 (2.1); 1.2562 (0.6); 1.2290 (2.0); 1.2114 (3.9); 1.1939 (2.0); 0.1463 (0.7); 0.0494 (0.9); 0.0079 (6.5);

-0.0002 (188.2); -0.0085 (6.4); -0.0502 (2.2); -0.1494 (0.8).

Example No. I.1-334.

1H-NMR (400.0 MHz, CDCI3): δ = 7.5183 (1.9); 7.3597 (5.2); 7.3375 (5.3); 7.3091 (1.8); 7.2595 (311.0); 7.2334 (4.5); 7.2164 (1.4); 6.9954 (1.8); 6.7778 (1.7); 6.3373 (6.4); 6.3278 (3.1); 4.1573 (1.2); 4.1084 (1.2);

3.9764 (1.3); 3.9557 (1.9); 3.9383 (1.2); 3.9031 (1.0); 3.8821 (1.9); 3.8522 (2.1); 3.8340 (2.4); 3.8226 (1.8);

3.5404 (16.0); 3.5145 (1.2); 3.4614 (0.8); 3.4369 (1.0); 3.4265 (1.3); 3.4126 (1.2); 3.4037 (1.6); 3.3817 (3.6);

3.3689 (3.4); 3.3271 (0.6); 3.3128 (1.3); 3.2985 (1.4); 3.2775 (1.0); 3.2640 (0.9); 1.6105 (13.7); 1.5923 (13.9); 1.5386 (73.1); 1.4280 (13.7); 1.3900 (12.4); 1.2875 (9.3); 1.2784 (11.6); 0.1466 (0.7); 0.0494 (0.8); -0.0002 (132.0); -0.1499 (0.6).

Example No. I.1-335.

¹ H-NMR (400.0 MHz, CDCl3): δ = 7.5863 (2.0); 7.5816 (0.7); 7.5732 (0.8); 7.5689 (2.5); 7.5675 (2.6);

7.5627 (0.8); 7.5542 (0.7); 7.5502 (2.0); 7.3850 (3.3); 7.3753 (1.2); 7.3622 (3.3); 7.3525 (1.1); 7.2615 (54.0); 6.3544(3.6); 6.3474 (4.5); 5.7911 (0.6); 5.7802 (0.6); 5.7643 (0.5); 5.7500 (0.5); 5.1598 (1.4); 5.1576 (1.2);

5.1524 (1.1); 5.1477(1.6); 5.1192(2.6); 5.0780 (0.6); 4.7494 (0.6); 4.7371 (0.7); 4.7318 (1.0); 4.7196 (1.0);

4.7143 (0.7); 4.7019 (0.6); 4.0587 (1.4); 4.0542 (1.4); 4.0418 (1.5); 4.0373 (1.4); 3.9475 (0.5); 3.9349 (0.8);

3.9310 (0.8); 3.9182 (0.5); 3.8959 (0.7); 3.8917 (0.7); 3.8870 (0.6); 3.8820 (0.7); 3.8780 (0.5); 3.8286 (0.7);

3.8230 (0.9); 3.8178 (0.9); 3.8120 (0.7); 3.7770 (0.6); 3.7719 (0.5); 3.5565 (6.8); 3.5535 (8.6); 3.5500 (8.2);

3.4250 (1.0); 3.4231 (1.0); 3.4071 (0.9); 3.4048 (1.0); 3.3993 (1.6); 3.3974 (1.6); 3.3814 (1.5); 3.3792 (1.4);

3.3394 (1.4); 3.3341 (1.4); 3.3271 (2.0); 3.3220 (1.6); 3.3135 (1.1); 3.3107 (1.1); 3.3085 (1.1); 3.3015 (1.0);

3.2961 (0.9); 3.2897 (0.5); 3.2776 (15.6); 3.2742 (16.0); 3.2616 (4.1); 3.2572 (4.1); 1.5084 (1.4); 1.5033 (1.5); 1.4911 (1.5); 1.4859 (1.6); 1.4682(5.3); 1.4634 (5.4); 1.4514 (5.4); 1.4465 (5.3); 1.4347 (0.8); 1.3881 (0.7); 1.2161 (2.7); 1.1990 (2.6); 1.1092(5.3); 1.1003 (5.5); 1.0918 (5.4); 1.0828 (5.3); 0.0080 (0.6); -0.0002 (20.4);

-0.0085 (0.6).

Example No. I.1-340.

1 H-NMR (400.0 MHz, CDCI3): δ = 7.5183 (5.2); 7.4046 (3.2); 7.3992 (3.2); 7.3960 (3.0); 7.3929 (2.9);

7.3822 (3.4);

7.2881 (5.1);

6.6946 (1.2);

3.8137 (1.9);

3.7314 (0.6);

3.3430 (2.1);

3.0363 (1.6);

2.9179 (1.0);

2.7949 (1.3);

2.5846 (1.2);

2.3785 (1.5);

7.3769 (3.4); 7.3735 (3.1); 7.3708 (2.9); 7.3530 (2.9); 7.3349 (3.1); 7.3171 (2.8); 7.2990 (3.0);

7.2700 (8.4); 7.2595 (876.8); 7.2497 (2.1); 7.2441 (0.9); 7.2330 (0.6); 7.2100 (0.9); 6.9954 (5.0);

6.6696 (1.3); 6.5432 (1.4); 6.5145 (1.4); 6.3435 (8.1); 6.3390 (5.4); 6.3287 (4.0); 3.8262 (1.7);

3.8079 (1.9); 3.7957 (2.1); 3.7790 (2.4); 3.7677 (2.3); 3.7608(2.2); 3.7496 (2.3); 3.7427 (0.7); 3.5503 (11.8); 3.5475 (12.2); 3.5326 (9.3); 3.3944 (2.4); 3.3731 (1.9); 3.3677 (3.1); 3.3643 (3.2); 3.3318 (2.1); 3.1469 (1.9); 3.1343 (1.7); 3.1171 (1.5); 3.1071 (1.5); 3.0927 (1.3); 3.0665 (2.3);

3.0246 (1.1); 3.0164 (1.4); 3.0079 (1.0); 2.9969 (1.4); 2.9862 (0.8); 2.9373 (0.8); 2.9285 (0.9);

2.9089 (1.6); 2.9012(1.2); 2.8899 (1.1); 2.8812 (1.1); 2.8229 (0.8); 2.8146 (0.8); 2.8055 (1.0);

2.7860 (0.9); 2.7771 (1.2); 2.7691 (0.8); 2.7493 (1.0); 2.7016 (0.8); 2.6179 (0.7); 2.6021 (1.0);

2.5704 (0.8); 2.4438 (1.5); 2.4228 (2.1); 2.4119 (1.9); 2.4038 (1.5); 2.3997 (1.4); 2.3930 (1.6);

2.3173 (0.6); 2.2968 (0.8); 2.2843 (1.2); 2.2624 (1.0); 2.2504 (0.7); 2.0052 (0.7); 1.7338 (2.9);

1.6305 (9.5); 1.6169 (9.6); 1.6119 (16.0); 1.5989 (8.5); 1.5934 (8.8); 0.1460 (1.7); 0.0080 (15.6); -0.0002 (517.3); -0.0085 (15.6); -0.0497 (0.8); -0.1497 (1.8).

Example No. I.1-341.

¹ H-NMR (400.0 MHz, CDCl3): δ = 7.5177 (9.7); 7.5104 (2.9); 7.4971 (6.4); 7.4916 (2.7); 7.4134 (6.0); 7.3908 (6.1); 7.2923 (1.7); 7.2590 (1346.6); 7.2089 (1.9); 6.9950 (7.2); 6.3591 (7.7); 6.3446 (8.8); 3.9555 (3.5); 3.9379 (5.0); 3.9204 (3.4); 3.8697 (3.4); 3.8499 (4.0); 3.8317 (1.8); 3.7377 (2.0); 3.7261 (2.1); 3.7174 (2.5); 3.7044 (2.8); 3.6964 (2.4); 3.6913 (2.3); 3.6744 (4.0); 3.6577 (3.8); 3.6486 (5.0); 3.6431(4.9); 3.6356 (3.4); 3.6200 (3.5); 3.5529 (16.0); 1.9935 (1.6); 1.9741 (1.6); 1.7158 (1.6); 1.5591(15.5); 1.5565 (12.9); 1.5413 (15.1); 1.5387 (12.6); 0.0080 (14.4); -0.0002 (499.6); -0.0085 (14.4); -0.1498 (1.6).

- 65 042986

Example No. I.2-71.

Diastereomer 1 - 1H-NMR (400.0 MHz, CDCl ₃ ): δ = 7.5532 (1.4); 7.5465 (1.4); 7.5344 (1.4); 7.5278 (1.4); 7.5181 (2.5); 7.5138 (1.6); 7.4985 (1.4); 7.4951 (1.5); 7.3611 (3.9); 7.3383 (3.9); 7.2594 (306.1); 7.2465 (0.6); 6.9954 (1.7); 6.3443 (6.1); 6.3392 (2.3); 4.1684 (0.7); 4.1596 (0.7); 4.1545 (0.7); 4.1460 (0.8); 4.1405 (0.8); 4.1317 (1.1); 4.1269 (0.9); 4.1183 (0.9); 4.0813 (0.6); 4.0681 (0.8); 4.0623 (1.2); 4.0500 (1.3); 4.0444 (1.2); 4.0351 (0.8); 4.0284 (1.3); 4.0174 (1.0); 4.0129 (1.5); 4.0004 (1.3); 3.9922 (2.1); 3.9861 (1.7); 3.9767 (1.3); 3.9701 (1.0); 3.9649 (1.0); 3.9583 (1.1); 3.9490 (0.7); 3.9422 (0.7); 3.8278 (0.5); 3.8149 (0.6); 3.8109 (1.5); 3.8075 (1.2); 3.7942 (1.3); 3.7903 (1.8); 3.7737 (0.9); 3.7654 (0.9); 3.7469 (1.4); 3.7347 (1.6); 3.7308 (1.8); 3.7181 (1.7); 3.7146 (2.4); 3.7114 (1.4); 3.6982 (1.1); 3.6946 (1.0); 3.5519 (9.2); 3.5488 (10.6); 3.5461 (6.8); 2.0048(2.5); 1.9846 (1.0); 1.9818 (1.1); 1.9648 (1.4); 1.9463 (1.3); 1.9348 (0.8); 1.9304 (0.8); 1.9134 (0.8); 1.9051 (0.8); 1.9012 (1.0); 1.8922 (0.9); 1.8845 (1.5); 1.8687 (2.1); 1.8663 (2.1); 1.8569 (1.6); 1.8519 (2.1); 1.8480 (2.1); 1.8314 (1.5); 1.8150 (0.8); 1.5660 (2.0); 1.5426 (1.2); 1.5368 (1.0); 1.5230 (0.9); 1.5129 (0.7); 1.5058 (0.9); 1.4938 (0.7); 1.4889 (0.7); 1.0816 (7.2); 1.0631 (16.0); 1.0447 (6.6); 0.3307 (0.6); 0.2375 (0.6); 0.1263 (0.7); 0.0080 (3.8); -0.0002 (127.1); -0.0085 (3.8). Diastereomer 2 - 1H-NMR (400.0 MHz,

CDCl3): δ = 7.5535 (1.6); 7.5469 (1.6); 7.5346 (1.7); 7.5281 (1.6); 7.5177 (1.3); 7.5142 (1.3); 7.4990 (1.2); 7.4955 (1.3); 7.3612 (3.9); 7.3384 (3.9); 7.2606 (53.4); 6.3440 (6.8); 6.3390 (2.2); 4.1679 (0.7); 4.1591 (0.8);

4.1541 (0.8); 4.1456 (0.8); 4.1400 (1.0); 4.1312 (1.1); 4.1266 (1.0); 4.1180 (1.0); 4.0812 (0.5); 4.0681 (0.7);

4.0622 (1.0); 4.0590 (0.9); 4.0502 (1.4); 4.0430 (1.2); 4.0345 (1.1); 4.0284 (1.0); 4.0174 (1.1); 4.0130 (1.3);

4.0008 (1.2); 3.9923 (2.0); 3.9863 (1.9); 3.9773 (1.4); 3.9703 (1.1); 3.9651 (1.2); 3.9584 (1.2); 3.9492 (0.7);

3.9424 (0.7); 3.8272 (0.6); 3.8142 (0.7); 3.8102 (1.6); 3.8066 (1.2); 3.7935 (1.5); 3.7895 (1.8); 3.7729 (0.9);

3.7661 (0.8); 3.7463 (1.3); 3.7343 (1.6); 3.7310 (2.0); 3.7251 (1.0); 3.7183 (2.2); 3.7147 (2.5); 3.7115 (1.6);

3.7071 (0.8); 3.6982 (1.5); 3.6947 (1.3); 3.5515 (10.1); 3.5485 (11.4); 2.0002 (0.8); 1.9844 (1.1); 1.9817 (1.2); 1.9646 (1.6); 1.9462 (1.4); 1.9341 (0.8); 1.9303 (0.9); 1.9263 (0.8); 1.9170 (0.6); 1.9130 (1.0); 1.9082 (0.8);

1.9049 (0.9); 1.9007 (1.0); 1.8924 (1.1); 1.8838 (1.5); 1.8738 (1.4); 1.8686 (2.2); 1.8662 (1.9); 1.8568 (1.8);

1.8518 (2.3); 1.8480 (2.0); 1.8384 (1.4); 1.8355 (1.7); 1.8222 (0.8); 1.8174 (0.9); 1.5559 (11.0); 1.5425 (0.6); 1.5369 (0.5); 1.5236 (0.7); 1.5144 (0.6); 1.5057 (0.9); 1.4967 (0.6); 1.4890 (0.7); 1.2565 (0.5); 1.0817 (7.4);

1.0632 (16.0); 1.0448 (6.8); 0.0692 (2.1); 0.0080 (0.7); -0.0002 (22.2); -0.0085 (0.6).

Example No. I.2-73.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5451 (1.5); 7.5341 (1.5); 7.5263 (1.6); 7.5189 (0.9); 7.5150 (3.3); 7.5103 (2.0); 7.4961 (1.9); 7.4916 (1.9); 7.3631 (3.0); 7.3521(3.6); 7.3403 (3.1); 7.3293 (3.6); 7.2601 (108.8); 6.9961 (0.6); 6.3483 (8.6); 4.1122 (0.7); 4.1076 (0.8); 4.1032 (0.8); 4.0987 (0.8); 4.0833 (1.2); 4.0787 (1.3);

4.0743 (1.3); 4.0698 (1.3); 4.0652 (0.6); 4.0476 (0.5); 4.0364 (1.1); 4.0268 (1.1); 4.0187 (1.2); 4.0091 (1.3);

4.0058 (1.4); 3.9998 (1.3); 3.9929 (1.3); 3.9888 (2.1); 3.9835 (2.2); 3.9794 (1.4); 3.9772 (1.0); 3.9709 (0.8);

3.9641 (0.6); 3.9600 (1.2); 3.9544 (1.1); 3.9506 (0.6); 3.9332 (1.3); 3.9288 (1.2); 3.9100 (1.0); 3.9050 (1.2);

3.8996 (1.3); 3.7563 (1.0); 3.7536 (1.0); 3.7498 (1.0); 3.7368 (2.1); 3.7334 (2.2); 3.7298 (1.2); 3.7195 (1.0);

3.7169 (1.1); 3.7132 (1.0); 3.5531 (14.1); 3.5188 (0.5); 3.4630 (0.7); 3.4543 (0.5); 3.4467 (0.7); 3.4412 (0.6); 3.4375 (0.6); 3.4326 (0.6); 3.3960 (1.0); 3.3897 (1.2); 3.3680 (1.4); 3.3627 (1.5); 3.3414 (0.7); 3.3348 (0.6);

2.0144 (0.6); 1.9964 (1.1); 1.9790 (1.5); 1.9609 (1.7); 1.9427 (1.0); 1.8932 (0.6); 1.8896 (0.6); 1.8752 (1.1);

1.8582 (1.5); 1.8547 (1.2); 1.8402 (2.1); 1.8224 (1.5); 1.8052(1.2); 1.5470 (43.7); 1.5035(2.2); 1.4856 (4.2); 1.4529(1.2); 1.4432 (1.0); 1.2545 (0.9); 1.2422 (0.8); 1.2325 (0.6); 1.2238 (0.8); 1.2136 (0.7); 1.0753 (7.5); 1.0569 (16.0); 1.0384 (6.9); 0.0080 (1.2); -0.0002 (39.9); -0.0085 (1.2).

Example No. I.2-81.

1H-NMR (400.0 MHz, CDCl3): δ = 8.0511 (1.1); 8.0299 (1.3); 7.6910 (0.9); 7.6701 (1.3); 7.5891 (0.7); 7.5868 (0.7); 7.5718 (0.8); 7.5694 (0.9); 7.5509 (0.6); 7.5486 (0.6); 7.5188 (1.1); 7.5132 (2.4); 7.5112 (2.6);

7.4944 (4.4); 7.4925 (4.6); 7.4826 (0.6); 7.4755 (2.1); 7.4737 (2.2); 7.4512 (0.8); 7.4487 (0.8); 7.4338 (0.6);

7.4303 (0.9); 7.4275 (0.7); 7.4128 (0.5); 7.4102 (0.6); 7.3630 (7.3); 7.3403 (7.6); 7.3342 (0.7); 7.2924 (0.5);

7.2599(156.9); 6.9959 (0.9); 6.3558 (3.8); 6.3528 (3.7); 6.3457 (5.1); 6.2805 (0.8); 6.2266 (9.4); 4.1334 (1.0); 4.1134 (1.4); 4.1057 (2.1); 4.0936 (0.8); 4.0863(2.9); 4.0778 (1.2); 4.0665 (1.2); 4.0594 (1.3); 4.0249 (1.5);

4.0097 (2.5); 3.9979 (2.3); 3.9936 (1.6); 3.9815 (2.5); 3.9707 (1.0); 3.9663 (1.0); 3.9540 (0.9); 3.7273 (0.9);

3.7242 (1.0); 3.7109 (1.1); 3.7074 (1.8); 3.7037 (1.2); 3.7001(1.1); 3.6926 (1.3); 3.6873 (1.1); 3.6836 (1.2);

3.6795 (1.3); 3.6766 (1.4); 3.6726 (1.2); 3.6630 (1.0); 3.6561 (1.0); 3.5578 (10.1); 3.5521 (11.4); 3.5489 (10.3); 3.5189 (2.6); 3.5030 (1.6); 3.4862 (1.2); 3.4750 (0.9); 2.8589 (0.7); 2.8473 (1.1); 2.8412 (1.1); 2.8346 (1.6);

2.8249 (1.5); 2.8221 (1.6); 2.8066 (1.8); 2.7900 (2.2); 2.7737 (1.3); 2.7646 (1.0); 2.7481 (0.5); 2.0165 (0.9);

1.9983 (1.7); 1.9851 (2.2); 1.9816 (3.3); 1.9776 (2.2); 1.9614 (4.9); 1.9510 (4.8); 1.9460 (4.5); 1.9427 (3.9);

1.9275 (1.8); 1.9165 (1.1); 1.8943 (1.0); 1.8860 (0.8); 1.8757 (1.4); 1.8680 (1.3); 1.8572 (1.3); 1.8499 (1.2);

1.8407 (1.0); 1.8329 (0.9); 1.8222 (0.5); 1.6925 (0.8); 1.6797 (1.3); 1.6644 (1.4); 1.6512(1.2); 1.6371 (0.9);

1.5488 (14.4); 1.2557 (1.2); 1.0842 (8.0); 1.0659 (16.0); 1.0475 (7.2); 0.0080 (1.9); -0.0002 (66.2); -0.0085 (2.3).

Example No. I.2-221.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5187 (2.0); 7.4538 (0.6); 7.4308 (0.6); 7.3512 (2.0); 7.3489 (2.1); 7.3403 (2.1); 7.3387 (2.1); 7.3285 (2.1); 7.3262 (2.2); 7.3213 (2.0); 7.3180 (2.3); 7.3162(2.2); 7.3102 (0.9);

- 66 042986

7.3030 (1.9); 7.2936 (1.8); 7.2888 (0.8); 7.2879 (0.8); 7.2872 (0.8); 7.2863 (0.8); 7.2856 (0.8); 7.2839 (0.9);

7.2832 (1.0); 7.2824 (1.0); 7.2816 (1.0); 7.2808 (1.0); 7.2800 (1.0); 7.2792 (1.2); 7.2784 (1.2); 7.2776 (1.4);

7.2753 (3.0); 7.2737 (2.0); 7.2729 (1.9); 7.2721 (2.0); 7.2712 (2.0); 7.2704 (2.2); 7.2696 (2.5); 7.2689 (2.7);

7.2681 (2.9); 7.2672 (3.3); 7.2664 (3.9); 7.2656 (4.6); 7.2648 (5.7); 7.2640 (7.2); 7.2598 (352.2); 7.2535 (2.7);

7.2527 (2.1); 7.2519 (1.5); 7.2511 (0.9); 7.2503 (0.6); 7.2185 (1.6); 7.2104 (0.6); 7.2004 (1.5); 7.1961 (1.6);

7.1782(1.4); 6.9958 (2.0); 6.7325 (0.8); 6.3583 (0.7); 6.3328 (5.3); 3.8618 (0.6); 3.8482 (0.7); 3.8311 (0.8);

3.8240 (1.0); 3.8051 (1.4); 3.7881 (1.4); 3.7722 (0.5); 3.7458 (0.6); 3.7332 (1.0); 3.7177 (0.7); 3.7154 (0.8);

3.7002 (0.6); 3.6795 (1.5); 3.6695 (1.2); 3.6636 (2.4); 3.6519 (1.5); 3.6425 (2.8); 3.6350 (0.9); 3.6257 (1.4);

3.5603 (1.4); 3.5570 (1.7); 3.5438 (9.0); 3.5406 (10.4); 3.5378 (9.4); 3.5347 (6.0); 3.5133 (0.6); 3.5050 (0.7);

3.4976 (0.6); 3.4791 (0.5); 3.4725 (0.6); 3.4635 (0.9); 3.4559 (0.9); 3.4499 (0.8); 3.4245 (0.5); 3.4215 (0.5);

3.4155 (0.8); 3.4098 (0.5); 3.2038 (0.6); 3.1865 (0.6); 3.1697 (0.5); 3.1527 (0.5); 3.1382 (0.7); 3.1325 (0.6);

3.1255 (0.6); 3.1197 (0.9); 3.1141 (0.5); 3.1068 (0.5); 3.1017 (0.7); 3.0982 (0.5); 3.0854 (0.7); 2.4455 (3.9);

2.0791 (0.8); 2.0624 (1.4); 2.0439 (2.3); 2.0257 (1.9); 2.0087 (1.4); 1.9402 (0.7); 1.9296 (1.0); 1.9220 (1.3);

1.9128 (1.2); 1.9036 (1.4); 1.8947 (1.5); 1.8864 (1.4); 1.8765 (1.7); 1.8680 (1.6); 1.8594 (2.0); 1.8509 (1.5);

1.8399 (2.0); 1.8273 (1.3); 1.8224 (1.3); 1.8120 (1.0); 1.8018 (0.7); 1.7819 (0.6); 1.5445 (16.0); 1.4716 (0.5);

1.4503 (0.5); 1.4411 (0.8); 1.4225 (0.7); 1.3328 (0.7); 1.3199 (0.6); 1.3106 (0.8); 1.3015 (0.8); 1.2930 (0.6);

1.2843 (0.9); 1.2560 (2.5); 1.1214 (5.6); 1.1029 (11.4); 1.0846 (5.1); 0.8802 (0.6); 0.0144 (0.5); 0.0136 (0.6);

0.0127 (0.6); 0.0120 (0.7); 0.0112 (0.8); 0.0103 (0.9); 0.0080 (4.4); 0.0064 (1.7); 0.0056 (1.8); 0.0048 (2.2);

0.0039 (2.8); -0.0002 (135.1); -0.0050 (2.4); -0.0058 (1.8); -0.0067 (1.5); -0.0084 (3.9); -0.0106 (0.6).

Example No. I.2-224.

1H-NMR (400.0 MHz, CDCl3): δ = 7.3473 (2.3); 7.3458 (2.3); 7.3312 (2.2); 7.3290 (2.3); 7.3248 (2.5);

7.3233 (2.4); 7.3088 (2.1); 7.3067 (2.2); 7.2817 (1.9); 7.2610 (80.2); 7.2385 (1.8); 7.1814 (1.6); 7.1635 (1.7);

7.1584 (1.8); 7.1405 (1.6); 6.7717 (0.5); 6.3343 (6.0); 6.3274 (3.4); 3.8225 (1.1); 3.8052 (1.5); 3.7995 (0.9);

3.7946 (1.0); 3.7892 (1.9); 3.7824 (1.9); 3.7775 (1.9); 3.7706 (1.1); 3.7649 (1.1); 3.7606 (1.2); 3.7565 (1.0);

3.7499 (0.5); 3.7028 (0.8); 3.6990 (0.8); 3.6855 (1.7); 3.6684 (1.9); 3.6646(2.6); 3.6545 (1.2); 3.6474 (3.5);

3.6368 (0.6); 3.6301 (1.9); 3.5453 (8.9); 3.5423 (8.2); 3.5392 (8.2); 3.5364 (9.0); 3.5336 (6.4); 3.3588 (0.7);

3.3422 (0.7); 3.3248 (1.1); 3.3082 (1.0); 3.2649 (4.4); 3.2501 (4.4); 3.2218 (1.0); 3.2168 (1.1); 3.2089 (1.1);

3.2041 (1.0); 3.1878 (0.6); 3.1829 (0.7); 3.1749 (0.6); 3.1701 (0.6); 2.0897 (0.6); 2.0854 (0.5); 2.0727 (1.0);

2.0689 (1.0); 2.0545 (1.6); 2.0503 (1.6); 2.0361 (1.4); 2.0337 (1.3); 2.0319 (1.3); 2.0193 (0.9); 2.0151 (1.0);

1.9572 (0.6); 1.9498 (0.7); 1.9387 (1.2); 1.9314 (1.4); 1.9203 (1.3); 1.9126 (1.6); 1.9096 (1.7); 1.9019 (1.3);

1.8913 (1.8); 1.8848 (1.2); 1.8743 (1.7); 1.8665 (1.0); 1.8569 (1.4); 1.8529 (1.0); 1.8482 (0.8); 1.8406 (1.0);

1.8271 (0.7); 1.8218 (0.7); 1.6718 (0.8); 1.6539 (1.7); 1.6460 (1.6); 1.6305 (1.6); 1.6245 (1.7); 1.6150 (0.9);

1.6095 (1.2); 1.6018 (0.6); 1.5986 (0.7); 1.5935 (0.7); 1.5744 (16.0); 1.5553 (0.6); 1.5438 (1.3); 1.5309 (0.9);

1.5236 (1.0); 1.5101 (0.8); 1.4876 (0.8); 1.4724 (0.7); 1.3039 (0.5); 1.2845 (0.8); 1.2647 (2.6); 1.1361 (3.6);

1.1170 (9.2); 1.1141 (10.9); 1.1100 (10.4); 1.1028(8.9); 1.0846 (3.5); 1.0525(9.5); 1.0452(9.4); 0.8987 (1.3); 0.8818 (4.3); 0.8641 (1.7); 0.0691 (0.9); 0.0079 (1.0); -0.0002 (33.6); -0.0085 (1.1).

Example No. I.2-336.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5184 (1.9); 7.3794 (0.6); 7.3726 (1.2); 7.3652 (4.9); 7.3499 (1.9); 7.3428 (3.2); 7.3286 (3.6); 7.3066 (3.8); 7.2596 (324.2); 7.1146 (0.7); 7.0983 (2.1); 7.0928 (2.2); 7.0807 (1.6); 7.0750 (1.6); 6.9955 (1.6); 6.8893 (0.8); 6.8643 (0.9); 6.3413 (4.9); 6.3341 (2.6); 6.3186 (2.8); 4.5861 (0.6);

4.5598 (0.8); 4.5393 (0.7); 4.4760 (0.7); 4.2233 (0.8); 4.2053 (1.1); 4.1806 (1.1); 4.1571 (1.0); 4.1387 (0.9);

3.8751 (1.1); 3.8576 (2.1); 3.8501 (1.0); 3.8399 (1.1); 3.8356 (1.2); 3.8310 (1.2); 3.8078 (1.6); 3.7945 (1.6);

3.7773 (0.9); 3.7583 (1.0); 3.7466 (0.9); 3.7381 (1.0); 3.7283 (1.2); 3.7109 (1.6); 3.7060 (1.6); 3.6939 (0.8);

3.6887 (0.7); 3.6235 (0.7); 3.6044 (0.7); 3.5917 (0.8); 3.5737 (0.8); 3.5468 (8.0); 3.5438 (7.8); 3.5325 (4.1);

3.5297(4.2); 2.0958 (0.5); 2.0775 (0.8); 2.0600 (1.1); 2.0434 (1.5); 2.0182 (1.9); 2.0006 (2.6); 1.9818 (1.9);

1.9636 (0.6); 1.9265 (0.5); 1.9089 (0.8); 1.8943 (1.2); 1.8761 (1.6); 1.8559 (1.6); 1.8361 (1.4); 1.6563 (0.7);

1.5420 (16.0); 1.3768 (0.9); 1.2551(1.6); 1.1528 (3.4); 1.1340 (7.0); 1.1157 (3.3); 1.1018 (3.9); 1.0833 (8.1); 1.0650 (3.7); 1.0483 (0.7); 1.0253 (0.7); 0.9935 (0.6); 0.3306 (0.8); 0.2374 (0.8); 0.1569 (0.6); 0.1262 (0.7); 0.0688 (3.7); 0.0079 (3.7); -0.0002 (128.2); -0.0085 (4.4).

Example No. I.4-71.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5634 (0.6); 7.5592 (0.7); 7.5499 (1.9); 7.5440 (2.2); 7.5407 (1.1); 7.5311 (2.0); 7.5251 (1.8); 7.5193 (0.9); 7.5117 (1.6); 7.5058 (1.6); 7.4930 (1.5); 7.4871 (1.6); 7.3673 (2.1);

7.3637 (4.8); 7.3550 (1.1); 7.3443 (2.2); 7.3409 (4.8); 7.3323 (1.2); 7.2742 (0.5); 7.2726 (0.6); 7.2702 (0.8);

7.2694 (0.9); 7.2669 (1.4); 7.2604(126.2); 6.9964 (0.7); 6.3424 (8.0); 6.3372 (3.0); 6.3242 (0.6); 4.1500 (0.9); 4.1408 (1.0); 4.1335 (1.0); 4.1243 (1.3); 4.1217 (1.3); 4.1126 (1.4); 4.1053 (1.2); 4.0962 (1.4); 4.0509 (0.6);

4.0430 (0.8); 4.0346 (1.2); 4.0275 (1.5); 4.0194 (1.1); 4.0159 (1.5); 4.0116 (1.5); 4.0079 (2.0); 3.9987 (2.3);

3.9928 (0.9); 3.9889 (1.2); 3.9847 (2.2); 3.9727 (1.5); 3.9667 (0.5); 3.9583 (1.1); 3.9552 (0.9); 3.9467 (1.3);

3.9380 (1.8); 3.9306 (1.8); 3.9224 (1.4); 3.9148 (2.3); 3.9099 (1.3); 3.9023 (1.4); 3.8971 (2.0); 3.8945 (2.4);

3.8867 (1.2); 3.8803 (1.1); 3.8767 (2.3); 3.8630 (1.2); 3.8597 (1.9); 3.8562 (1.2); 3.8423 (1.2); 3.8387 (1.1);

3.8315 (0.5); 3.8230 (0.7); 3.8174 (1.0); 3.8146 (0.8); 3.8062 (0.8); 3.8008 (1.4); 3.7971 (1.7); 3.7896 (0.6);

3.7849 (1.5); 3.7801 (2.1); 3.7767 (1.2); 3.7689 (0.9); 3.7633 (1.3); 3.7471 (0.8); 3.7375 (0.5); 3.7269 (1.0);

- 67 042986

3.7229 (0.7); 3.7148 (1.2); 3.7122 (1.2); 3.7091 (1.1); 3.7056 (0.9); 3.6993 (0.8); 3.6938 (1.0); 3.6880 (0.5);

3.5492 (11.8); 3.5463 (13.6); 3.5431 (9.6); 1.9568 (0.5); 1.9484 (0.6); 1.9402 (0.8); 1.9352 (0.9); 1.9269 (0.9);

1.9231 (0.9); 1.9182 (1.2); 1.9065 (1.4); 1.8948 (2.2); 1.8898 (1.7); 1.8860 (1.8); 1.8764 (2.5); 1.8695(2.2);

1.8602(2.6); 1.8523 (2.0); 1.8449 (2.8); 1.8311 (1.6); 1.8272(2.6); 1.8147(1.4); 1.8106 (1.5); 1.8061 (1.0);

1.7979 (1.2); 1.7942 (1.4); 1.7813 (1.3); 1.7781 (1.4); 1.7616 (1.2); 1.7454 (0.7); 1.7142 (0.8); 1.7090 (0.9);

1.7065 (0.9); 1.7025 (0.9); 1.6964 (0.8); 1.6915 (1.2); 1.6853 (1.2); 1.6813 (0.8); 1.6736 (1.0); 1.6686 (1.1);

1.6638 (0.7); 1.6588 (0.9); 1.6561 (0.9); 1.6523 (1.0); 1.6391 (0.6); 1.6354 (0.6); 1.5558 (4.6); 1.5296 (0.6);

1.5180 (0.7); 1.5064 (0.6); 1.5004 (1.0); 1.4885 (0.8); 1.4801 (1.0); 1.4711 (0.8); 1.4631 (0.7); 1.4536 (0.6);

0.9687 (2.0); 0.9578 (9.4); 0.9542 (9.8); 0.9445 (16.0); 0.9399 (9.8); 0.9287 (12.7); 0.9117 (1.3); 0.9091 (1.2); 0.8879 (1.7); 0.8720 (1.7); 0.8627 (1.0); 0.8540 (1.1); 0.8495 (2.1); 0.8382 (1.3); 0.8340 (1.9); 0.0079 (1.7); -0.0002 (54.9); -0.0085 (1.5).

Example No. I.4-72.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5197 (1.0); 7.4709 (2.4); 7.4659 (2.6); 7.4522 (2.4); 7.4471 (2.6); 7.3790 (4.7); 7.3563 (4.8); 7.3396 (0.9); 7.2722 (0.5); 7.2714 (0.5); 7.2706 (0.6); 7.2698 (0.7); 7.2690 (0.8); 7.2682 (0.9); 7.2674 (1.0); 7.2666 (1.2); 7.2658 (1.5); 7.2650 (1.9); 7.2608 (110.5); 7.2536 (0.5); 6.9968 (0.6); 6.3465 (8.9); 6.3365 (1.2); 4.0936 (0.8); 4.0818 (0.8); 4.0771 (0.8); 4.0663 (1.2); 4.0548 (1.0); 4.0500 (1.0);

4.0377 (0.9); 3.9838 (1.4); 3.9798 (1.3); 3.9676 (2.8); 3.9632 (1.5); 3.9501 (1.5); 3.9482 (1.6); 3.9209 (0.6);

3.8988 (1.2); 3.8944 (1.2); 3.8851 (1.0); 3.8785 (1.9); 3.8747 (1.5); 3.8723 (1.6); 3.8684 (1.4); 3.8618 (1.5);

3.8561 (2.3); 3.8508 (1.7); 3.8473 (1.8); 3.8396 (1.4); 3.8346 (1.2); 3.8216 (1.1); 3.8111 (1.0); 3.8004 (1.8);

3.7862 (1.7); 3.7799 (1.2); 3.7658(1.2); 3.7619 (1.2); 3.7445 (1.7); 3.7399 (1.5); 3.7345 (1.0); 3.7309 (1.6);

3.7268 (2.1); 3.7233 (2.3); 3.7138 (1.5); 3.7067 (2.0); 3.6950 (1.2); 3.6904 (1.1); 3.6876 (1.1); 3.5500 (14.8); 3.5470 (15.8); 3.4470 (0.9); 3.4318 (1.0); 3.4270 (1.8); 3.4128 (1.9); 3.4053 (1.3); 3.3910 (1.3); 2.4534 (0.5); 2.4354 (0.8); 2.4168 (0.8); 2.3998 (0.5); 1.9800 (0.7); 1.9728 (0.5); 1.9598 (1.0); 1.9478 (0.9); 1.9399 (0.9);

1.9277 (1.1); 1.9153 (0.8); 1.9087 (0.6); 1.8989 (1.0); 1.8831 (1.3); 1.8774 (1.0); 1.8657 (1.4); 1.8614 (1.3);

1.8505 (1.4); 1.8441 (1.2); 1.8283 (1.5); 1.7724 (0.6); 1.7558 (1.1); 1.7388 (1.4); 1.7227 (1.3); 1.7069 (0.8);

1.6879 (1.5); 1.6716 (1.8); 1.6549 (1.5); 1.6385 (1.3); 1.6205 (0.7); 1.5600 (11.4); 1.5376 (1.2); 1.5212 (1.0);

1.5042 (1.0); 1.4891 (0.7); 1.4331 (1.4); 0.9720 (2.4); 0.9569 (15.4); 0.9511 (16.0); 0.9414 (13.9); 0.9350 (15.2); 0.9193 (1.0); 0.9150 (1.0); 0.8954 (2.1); 0.8795 (2.0); 0.8708 (0.8); 0.8653 (0.9); 0.8580 (2.1); 0.8492 (1.0); 0.8422 (2.0); 0.0079 (1.3); -0.0002 (47.2); -0.0085 (1.3).

Example No. I.4-221.

1H-NMR (400.6 MHz, CDCl3): δ = 7.3505 (0.9); 7.3476 (1.0); 7.3399 (1.7); 7.3381 (1.3); 7.3279 (1.0); 7.3251 (1.1); 7.3216 (1.0); 7.3174 (1.1); 7.3154 (1.2); 7.3128 (1.0); 7.2944 (1.0); 7.2720 (0.5); 7.2714 (0.6); 7.2706 (0.6); 7.2697 (0.7); 7.2689 (0.8); 7.2682 (0.8); 7.2673 (0.9); 7.2623 (69.0); 7.2439 (0.7); 7.2257 (0.8); 7.2214 (0.8); 7.2033 (0.8); 6.3397 (1.4); 6.3341 (2.5); 6.3307 (1.6); 3.8158 (0.5); 3.7995 (0.7); 3.7941 (0.6);

3.7769 (1.1); 3.7600 (1.2); 3.7547 (0.8); 3.7440 (0.6); 3.7408 (0.8); 3.6741 (0.5); 3.6558 (0.7); 3.5512 (2.2);

3.5483 (2.9); 3.5461 (2.8); 3.5430 (2.5); 3.5386 (2.9); 3.5356 (3.5); 3.5328 (2.6); 2.0082 (0.7); 1.8773 (0.8);

1.8654(1.2); 1.8613 (1.2); 1.8497 (1.4); 1.8447 (1.4); 1.8360 (1.3); 1.8280 (1.4); 1.8199 (1.1); 1.8101 (0.9);

1.8012 (0.6); 1.7131 (0.5); 1.7064 (0.6); 1.6949 (0.6); 1.6927 (0.6); 1.6882 (0.7); 1.6824 (0.6); 1.6674 (0.6);

1.5855 (16.0); 1.2584 (0.6); 0.9780 (3.7); 0.9652 (5.5); 0.9621 (5.8); 0.9515 (2.8); 0.9494 (3.0); 0.9468 (2.6); -0.0002 (4.5).

Example No. I.5-71.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5347 (1.6); 7.5249 (1.6); 7.5192 (1.8); 7.5158 (1.8); 7.5121 (1.2); 7.5061 (1.6); 7.5009 (1.1); 7.4932 (0.9); 7.4719 (2.0); 7.4678 (0.9); 7.4625 (0.8); 7.4532 (2.0); 7.4492 (0.9); 7.4438 (0.8); 7.3494 (4.6); 7.3266 (4.7); 7.2601 (137.4); 6.9960 (0.8); 6.3397 (11.1); 6.3345 (3.8); 4.1565 (0.8); 4.1514 (0.6); 4.1476 (0.8); 4.1396 (0.8); 4.1309 (1.2); 4.1232 (0.8); 4.1193 (1.1); 4.1117 (1.0); 4.1027 (1.2);

4.0703 (0.7); 4.0634 (0.7); 4.0545 (1.2); 4.0514 (1.3); 4.0458 (1.5); 4.0373 (2.4); 4.0299 (2.0); 4.0214 (2.1);

4.0130 (1.3); 4.0038 (0.8); 3.9943 (1.6); 3.9863 (1.0); 3.9814 (1.7); 3.9773 (1.4); 3.9672 (1.9); 3.9531(1.9);

3.9480 (1.6); 3.9399 (1.0); 3.9373 (1.2); 3.9325 (1.5); 3.9246 (1.4); 3.9197 (1.0); 3.9120 (0.7); 3.9091 (0.8);

3.9042 (1.1); 3.8206 (0.7); 3.8036 (1.9); 3.7998 (1.9); 3.7830 (2.4); 3.7664 (1.1); 3.7340 (3.2); 3.7125 (5.7);

3.7063 (3.4); 3.6934 (2.8); 3.6901 (2.2); 3.6864 (3.2); 3.5468 (16.0); 2.0360 (0.9); 2.0193 (1.2); 2.0066 (1.2); 1.9894 (0.8); 1.9567 (0.6); 1.9376 (1.0); 1.9246 (1.2); 1.9180 (1.2); 1.9055 (1.8); 1.8937 (1.6); 1.8846 (1.4);

1.8781 (2.0); 1.8601 (2.2); 1.8430(2.2); 1.8302 (1.8); 1.8258 (1.5); 1.8128 (1.1); 1.8089 (1.1); 1.7986 (0.8);

1.7914 (0.8); 1.7830 (0.7); 1.7652 (0.6); 1.6167 (0.6); 1.5999 (0.8); 1.5814 (1.3); 1.5602 (8.8); 1.5350 (1.3);

1.5141 (1.2); 1.4979 (1.4); 1.4886 (1.2); 1.4816 (1.1); 1.4702 (0.7); 1.3924 (0.5); 1.3735 (0.8); 1.3514 (1.2);

1.3326 (1.4); 1.3169 (1.1); 1.3110(1.1); 1.2983 (1.1); 1.2767 (0.9); 1.2565 (1.3); 1.1424(6.4); 1.1386 (7.1); 1.1255 (6.3); 1.1217 (6.8); 1.0625 (7.0); 1.0456 (6.7); 0.9503 (3.6); 0.9441 (7.1); 0.9318 (7.1); 0.9256 (13.7); 0.9133 (3.3); 0.9071 (5.6); 0.8542 (0.5); 0.0080 (1.7); -0.0002 (55.0); -0.0084 (1.8).

Example No. I.5-72.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5188 (1.0); 7.4487 (1.2); 7.4439 (2.0); 7.4387 (2.5); 7.4346 (1.2); 7.4300 (1.5); 7.4252 (2.0); 7.4199 (2.5); 7.3650 (4.1); 7.3422 (4.1); 7.2598 (168.6); 6.9959 (0.9); 6.3440 (8.0); 4.1024 (0.7); 4.0935 (0.7); 4.0860 (0.8); 4.0759 (1.5); 4.0664 (1.0); 4.0588 (1.0); 4.0495 (1.0); 4.0001 (0.9);

- 68 042986

3.9952 (1.0); 3.9840 (1.1); 3.9786 (2.0); 3.9758 (2.2); 3.9566 (1.5); 3.9078 (0.7); 3.9030 (0.7); 3.8884 (0.7);

3.8830 (0.8); 3.8765 (0.7); 3.8612 (0.6); 3.8563 (0.6); 3.8242 (0.9); 3.8095 (1.3); 3.8036 (2.1); 3.7893 (2.2);

3.7833 (1.5); 3.7693 (2.3); 3.7501 (1.6); 3.7367 (1.9); 3.7333 (1.8); 3.7289 (1.9); 3.7159 (2.2); 3.7062 (1.8);

3.6947(2.6); 3.6891 (2.6); 3.6847 (3.3); 3.6745 (2.2); 3.6688 (1.7); 3.6643(2.2); 3.5470 (16.0); 3.4565 (1.1);

3.4390 (1.8); 3.4241 (1.7); 3.4180 (1.5); 3.4026 (1.3); 2.4742 (0.7); 2.4577 (1.0); 2.4398 (1.1); 2.4227 (0.7);

2.0161 (0.8); 2.0051 (1.1); 1.9987 (1.3); 1.9888 (1.4); 1.9793 (1.3); 1.9679 (1.6); 1.9553 (1.2); 1.9484 (1.1);

1.9348 (1.1); 1.9245 (0.7); 1.5912 (0.7); 1.5526 (6.1); 1.5288 (2.5); 1.5141 (1.6); 1.4977 (1.1); 1.3756 (0.6);

1.3573 (0.6); 1.3416 (0.6); 1.3294 (0.8); 1.3111 (1.1); 1.2900 (1.0); 1.2770 (0.9); 1.2558 (1.9); 1.1431(11.4);

1.1261 (11.0); 1.0483 (6.6); 1.0315 (6.4); 0.9594 (3.3); 0.9472 (6.0); 0.9409 (7.3); 0.9288 (11.8); 0.9224 (3.5); 0.9102 (4.7); 0.0690 (0.8); 0.0080 (2.1); -0.0002 (70.1); -0.0085 (2.4).

Example No. I.5-91.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5349 (1.3); 7.5212 (1.6); 7.5187 (1.7); 7.5160 (1.5); 7.5079 (1.0); 7.5023 (1.5); 7.4891 (1.0); 7.4794 (2.6); 7.4685 (1.7); 7.4607(2.6); 7.4498 (1.7); 7.3498 (2.9); 7.3388 (3.3); 7.3271 (3.0); 7.3159 (3.3); 7.3087 (0.6); 7.2927 (0.6); 7.2598 (206.5); 7.2220 (0.6); 7.2094 (1.0); 6.9958 (1.1); 6.3446 (8.4); 4.1110 (0.7); 4.1078 (0.7); 4.1004 (0.9); 4.0912 (0.9); 4.0823 (1.0); 4.0789 (1.0); 4.0707 (1.2);

4.0627 (1.0); 4.0431 (0.5); 4.0348 (0.5); 4.0259 (0.5); 4.0170 (1.0); 4.0144 (1.1); 4.0057(1.2); 3.9970 (1.2);

3.9885 (1.4); 3.9832 (1.2); 3.9734 (1.7); 3.9674 (2.3); 3.9629 (0.9); 3.9552 (1.6); 3.9499 (1.4); 3.9445 (1.3);

3.9383 (1.4); 3.9351 (1.4); 3.9265 (2.1); 3.9210 (1.9); 3.9062 (1.4); 3.8987 (1.5); 3.8896 (1.6); 3.7220(2.4);

3.7155 (3.0); 3.7004 (3.1); 3.6958 (3.0); 3.5497 (16.0); 3.5190 (0.8); 3.4460 (0.9); 3.4202 (1.0); 3.3835 (1.6);

3.3761 (1.4); 3.3563 (1.8); 3.3489 (1.5); 3.3358 (0.7); 3.3279 (0.9); 2.0371 (0.8); 2.0200 (1.1); 2.0100 (1.2);

1.8310 (1.5); 1.8004 (1.4); 1.7770 (0.7); 1.6047 (0.8); 1.5481 (14.7); 1.4797 (5.5); 1.4415 (1.4); 1.4095 (0.7); 1.3876 (0.6); 1.3680 (0.8); 1.3496 (1.2); 1.3314 (1.2); 1.3095 (1.1); 1.2908 (1.1); 1.2755 (1.0); 1.2568 (1.6);

1.2354 (1.1); 1.2219 (1.0); 1.1340 (9.4); 1.1171(9.3); 1.0628 (4.5); 1.0571 (4.2); 1.0460 (4.4); 1.0402 (4.0);

0.9437 (4.9); 0.9285 (8.0); 0.9253 (9.4); 0.9226 (8.3); 0.9098 (4.0); 0.9067 (4.2); 0.0080 (3.1); -0.0002 (80.3); -0.0058 (1.7); -0.0085 (2.8).

Example No. I.5-221.

1H-NMR (400.0 MHz, CDCl3): δ = 7.3403 (3.2); 7.3303 (3.8); 7.3177 (3.4); 7.3080 (5.6); 7.2896 (2.1); 7.2762 (2.7); 7.2614 (66.2); 7.1829(1.9); 7.1648 (2.1); 7.1591 (2.0); 7.1410 (2.0); 6.8890 (0.7); 6.8741 (0.8); 6.8567 (1.0); 6.8420 (1.1); 6.8286 (0.8); 6.8164 (0.8); 6.3342 (4.8); 6.3287 (9.1); 3.8612 (1.0); 3.8482 (0.9);

3.8269 (0.6); 3.8193 (1.1); 3.8018 (2.5); 3.7931 (1.7); 3.7840(2.9); 3.7756 (1.5); 3.7661 (1.3); 3.7571 (0.7);

3.7409 (1.0); 3.7280 (1.5); 3.7127 (1.5); 3.7022 (1.4); 3.6961 (1.3); 3.6822 (1.6); 3.6632 (5.7); 3.6549 (3.1);

3.6476 (5.6); 3.6400 (2.6); 3.6299 (1.6); 3.6102 (0.8); 3.5420 (10.4); 3.5330 (13.0); 3.5171 (0.9); 3.5123 (0.8); 3.5081 (0.8); 3.5003 (0.8); 3.4957 (0.8); 3.4912 (0.8); 3.4826 (0.9); 3.4778 (0.9); 3.4689 (1.4); 3.4611 (1.6);

3.4532 (1.4); 3.4462 (1.0); 3.4351 (0.8); 3.4266 (1.1); 3.4192 (1.0); 3.4119 (1.0); 3.4035 (0.5); 3.2025 (0.6);

3.1883 (1.2); 3.1723 (1.2); 3.1540(1.1); 3.1379 (1.0); 3.1236 (0.6); 3.1083 (0.7); 3.1032 (0.7); 3.0964 (0.7);

3.0906 (1.0); 3.0844 (0.6); 3.0733 (1.0); 3.0622 (0.6); 3.0563 (0.8); 3.0502 (0.5); 3.0430 (0.5); 2.1401 (0.9);

2.1337 (1.2); 2.1241 (1.4); 2.1177 (1.6); 2.1115 (1.4); 2.1016 (1.3); 2.0950 (1.0); 2.0853 (0.6); 1.9187 (0.6);

1.9060 (0.9); 1.9016 (0.9); 1.8847 (1.4); 1.8655 (2.0); 1.8606(2.2); 1.8506(2.2); 1.8437 (2.4); 1.8315 (2.7);

1.8255 (2.7); 1.8142 (2.0); 1.7950 (1.4); 1.7767 (1.2); 1.7579 (0.9); 1.7356 (1.1); 1.7255 (1.5); 1.7171 (1.8);

1.7013 (2.1); 1.6916 (1.7); 1.6825 (2.0); 1.6725 (1.5); 1.6539 (0.9); 1.5910 (7.0); 1.4842 (0.6); 1.4623 (0.8);

1.4549 (0.8); 1.4447 (0.9); 1.4363 (1.3); 1.4276 (0.6); 1.4180 (1.0); 1.3861 (0.8); 1.3739 (1.0); 1.3680 (1.1);

1.3514 (1.6); 1.3453 (1.3); 1.3335 (1.8); 1.3162 (1.6); 1.2987 (1.5); 1.2805(1.1); 1.2577 (1.4); 1.1228 (11.1); 1.1147 (11.3); 1.1059 (11.2); 1.0977 (10.5); 1.0780 (1.2); 1.0703 (0.6); 1.0599 (1.5); 1.0408 (0.8); 0.9614 (8.3); 0.9431 (16.0); 0.9246 (7.2); 0.0079 (1.4); -0.0002 (26.5); -0.0076 (1.1).

Example No. I.6-71.

Diastereomer 1 - 1H-NMR (400.0 MHz, CDCl ₃ ): δ = 7.5305 (2.5); 7.5216 (2.6); 7.5117 (2.5); 7.5029 (2.4); 7.4791(1.9); 7.4750 (2.0); 7.4604 (1.9); 7.4564 (1.9); 7.3733 (0.7); 7.3510 (6.3); 7.3282 (6.4); 7.3159 (1.4); 7.3100 (1.4); 7.2932 (1.5); 7.2604 (113.3); 6.9964 (0.6); 6.3411 (10.3); 6.3363 (3.9); 6.3192 (0.6); 4.7508 (0.6); 4.7392 (0.5); 4.1649 (1.3); 4.1559 (1.5); 4.1472 (1.4); 4.1369 (2.0); 4.1277(1.9); 4.1192 (1.6); 4.1102 (1.8); 4.0775 (1.3); 4.0589 (2.1); 4.0522 (1.7); 4.0426 (3.1); 4.0352 (2.2); 4.0266 (2.3); 4.0181 (1.4); 4.0096 (1.6); 3.9945 (2.2); 3.9785 (2.6); 3.9650 (1.6); 3.9613 (1.5); 3.9554 (2.2); 3.9479 (2.2); 3.9395 (1.3); 3.9317 (1.5); 3.9275 (1.4); 3.9197 (1.4); 3.9114 (1.0); 3.9035 (1.1); 3.8478 (0.6); 3.8278 (1.1); 3.8233 (1.2); 3.8105 (1.5); 3.8063 (2.6); 3.8025 (2.3); 3.7897 (2.4); 3.7854 (2.9); 3.7734 (1.0); 3.7688 (1.6); 3.7473 (1.1); 3.7289 (1.6); 3.7199 (1.6); 3.7139 (2.1); 3.7024 (1.3); 3.6959 (1.5); 3.6815 (0.6); 3.6719 (0.6); 3.6156 (3.4); 3.5942 (3.9); 3.5896 (3.5); 3.5848 (3.4); 3.5684 (3.8); 3.5637 (3.9); 3.5480 (16.0); 2.2721 (0.5); 2.2567 (0.8); 2.2408 (1.4); 2.2234 (1.9); 2.2057 (1.8); 2.1886 (1.1); 1.9616 (1.0); 1.9439 (1.5); 1.9293 (1.7); 1.9225 (1.6); 1.9103 (2.1); 1.8983 (2.0); 1.8934 (2.1); 1.8810 (2.6); 1.8623 (2.3); 1.8489 (2.3); 1.8317 (1.8); 1.8193 (0.9); 1.8148(1.1); 1.7980 (0.5); 1.5731 (6.5); 1.5505 (1.5); 1.5394 (1.3); 1.5187 (1.4); 1.5104 (1.2); 1.5020 (1.4); 1.4926 (1.1); 1.4851(1.1); 1.4735 (0.7); 1.2566 (1.4); 1.1983 (2.5); 1.1813 (3.0); 1.1681 (14.0); 1.1512 (12.4); 1.1261 (1.8); 1.0874 (15.4); 1.0707 (14.6); 0.9742 (1.1); 0.9653 (1.1); 0.9567 (1.2); 0.9515 (1.3); 0.9450 (1.3); 0.9343 (1.0); 0.9278 (1.1); 0.8902 (1.1); 0.8844 (1.1); 0.8731 (1.2); 0.8673 (1.5); 0.8525 (1.0); 0.0691 (2.2); 0.0495

- 69 042986 (0.6); 0.0080 (2.2); -0.0002 (47.6); -0.0085 (1.4). Diastereomer 2 - 1H-NMR (400.0 MHz, CDCl ₃ ): δ = 7.5306 (1.0); 7.5218 (1.0); 7.5190 (0.8); 7.5118 (1.0); 7.5030 (0.8); 7.4792 (0.7); 7.4751 (0.7); 7.4605 (0.7); 7.4563 (0.7); 7.3511 (2.4); 7.3283 (2.6); 7.3159 (0.8); 7.2930 (0.9); 7.2600 (87.8); 6.3414 (3.8); 6.3366 (1.4); 4.1561 (0.5); 4.1371 (0.7); 4.1277 (0.6); 4.1193 (0.6); 4.1103 (0.7); 4.0776 (0.5); 4.0592 (0.8); 4.0522 (0.6); 4.0428 (1.1); 4.0354 (0.8); 4.0265 (0.9); 4.0096 (0.6); 3.9946 (0.8); 3.9786 (1.0); 3.9650 (0.6); 3.9556 (0.8); 3.9481 (0.8); 3.9396 (0.5); 3.9318 (0.5); 3.9277 (0.5); 3.8063 (1.0); 3.8025 (0.9); 3.7898 (0.9); 3.7856 (1.1); 3.7688 (0.6); 3.7288 (0.6); 3.7137 (0.8); 3.6958 (0.6); 3.6156 (1.3); 3.5942(1.4); 3.5896 (1.2); 3.5849 (1.2); 3.5685 (1.3); 3.5637 (1.4); 3.5482 (6.0); 2.2407 (0.5); 2.2235 (0.7); 2.2056 (0.7); 1.9436 (0.5); 1.9304 (0.6); 1.9098 (0.7); 1.8987 (0.8); 1.8936 (0.8); 1.8812 (1.0); 1.8653 (0.9); 1.8490 (0.9); 1.8317 (0.7); 1.5451 (16.0); 1.5117 (0.6); 1.5019 (0.6); 1.2561 (0.5); 1.1978 (0.8); 1.1810 (1.0); 1.1682(5.2); 1.1512 (4.7); 1.1424 (1.0); 1.1254 (0.8); 1.0875 (5.8); 1.0708 (5.5); 0.9504 (0.5); 0.8669 (0.6); 0.0079 (1.6); -0.0002 (36.7); -0.0085 (1.3).

Example No. I.6-72.

1H-NMR (400.0 MHz, CDCl3): δ = 7.4494 (0.8); 7.4422 (0.9); 7.4313 (0.9); 7.4234 (0.8); 7.3668 (1.7);

7.3440 (1.6); 7.2600 (52.6); 7.2486 (4.5); 6.3444(2.9); 3.9972 (0.5); 3.9828 (1.0); 3.9637 (0.6); 3.8045 (0.8);

3.7905 (0.9); 3.7701 (0.8); 3.7381 (0.8); 3.7293 (0.9); 3.7169 (0.8); 3.6896 (0.6); 3.5670 (1.2); 3.5476 (7.5);

3.4456 (0.7); 3.4240 (0.7); 2.4434 (0.5); 2.2053 (0.6); 2.1849 (0.6); 1.5447 (16.0); 1.5014 (0.5); 1.1698(5.2);

1.1530 (4.8); 1.0714 (4.6); 1.0548 (4.6); 0.8641 (0.6); -0.0002 (21.5).

Example No. I.8-1.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5183 (1.0); 7.4509 (1.8); 7.4325 (1.8); 7.3573 (1.8); 7.3347 (1.8); 7.2595 (177.5); 6.9955 (1.0); 6.3526 (2.7); 4.2560 (1.9); 4.2480 (0.9); 4.2444 (1.7); 4.2404 (1.0); 4.2326 (2.0); 3.6814 (7.7); 3.5542 (5.0); 3.5493 (1.9); 3.5426 (1.7); 3.5390 (1.0); 3.5309 (1.9); 3.3345 (15.6); 1.5447 (16.0); 0.0079 (2.0); -0.0002 (66.1); -0.0085 (1.8).

Example No. I.8-71.

1H-NMR (400.0 MHz, CDCl3): δ = 7.4556 (3.8); 7.4533 (3.8); 7.4373 (3.8); 7.4350 (3.8); 7.3539 (6.5); 7.3313 (6.4); 7.2612 (22.7); 6.3513 (5.6); 6.3468 (5.7); 4.1694 (1.5); 4.1634 (3.1); 4.1439 (3.9); 4.1371 (2.3); 4.0831 (1.2); 4.0732 (1.3); 4.0661 (1.8); 4.0598 (1.6); 4.0562 (1.7); 4.0501 (4.1); 4.0468 (4.1); 4.0413 (1.6);

4.0389 (1.7); 4.0333 (0.9); 4.0239 (2.5); 4.0222 (2.5); 4.0071 (1.2); 4.0052 (1.1); 3.8570 (1.4); 3.8399 (2.5);

3.8359 (2.4); 3.8232 (1.6); 3.8189 (3.6); 3.8026 (1.6); 3.7669 (1.6); 3.7492 (2.3); 3.7335 (2.0); 3.7284 (1.7);

3.7129 (0.9); 3.6874 (14.5); 3.6848(15.2); 3.6468 (0.6); 3.5553 (11.1); 3.5523 (16.0); 3.5491 (11.7); 1.9827 (0.5); 1.9758 (0.6); 1.9653 (0.9); 1.9541 (0.9); 1.9444 (1.1); 1.9392 (0.8); 1.9325 (1.2); 1.9248 (1.1); 1.9182 (1.0); 1.9142(1.3); 1.9027 (1.5); 1.8991 (1.5); 1.8941 (1.0); 1.8839 (2.8); 1.8790 (1.5); 1.8666 (2.8); 1.8631 (2.1); 1.8534 (0.9); 1.8492 (1.3); 1.8460 (1.4); 1.8370 (0.5); 1.8286 (0.7); 1.5678 (0.6); 1.5579 (5.6); 1.5515 (1.4); 1.5424 (0.8); 1.5380 (0.8); 1.5339 (1.0); 1.5300 (1.1); 1.5206 (0.8); 1.5167 (0.8); 1.5024 (0.6); 1.2561 (0.7); 0.0080 (1.0); -0.0002 (28.3); -0.0084 (1.0).

Example No. I.8-72.

1H-NMR (400.0 MHz, CDCl3): δ = 7.4132 (1.8); 7.4110 (1.8); 7.3949 (1.8); 7.3927 (1.8); 7.3672 (3.1); 7.3446 (3.1); 7.2602 (33.7); 6.3546 (4.8); 4.1376 (0.7); 4.1212 (0.8); 4.1106(1.2); 4.0943 (1.2); 4.0203 (1.6); 4.0007 (1.7); 3.9932 (1.1); 3.9736 (1.1); 3.8260 (0.9); 3.8125 (1.0); 3.8055 (0.7); 3.7916 (0.6); 3.7776 (1.2);

3.7596 (1.4); 3.7554 (1.6); 3.7378 (2.2); 3.7194 (1.3); 3.7015 (1.1); 3.6804 (0.7); 3.6561 (11.2); 3.5559 (7.3);

3.5529 (7.3); 3.5036 (1.2); 3.4900 (1.3); 3.4813 (1.1); 3.4679 (1.0); 2.5140 (0.6); 2.0444 (0.8); 1.9916 (0.6);

1.9711 (0.6); 1.9581 (0.5); 1.5876 (0.5); 1.5705 (0.7); 1.5534 (0.7); 1.5403 (16.0); 1.2590 (0.9); 0.8818 (1.1);

0.0079 (1.4); -0.0002 (42.1); -0.0085 (1.5).

Example No. I.8-271.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5191 (1.1); 7.3651 (7.4); 7.3428 (7.2); 7.2603 (202.8); 7.2103 (1.2); 7.1112 (4.1); 7.0928 (6.0); 7.0745 (3.8); 6.9962 (1.1); 6.7496 (1.2); 6.7299 (1.2); 6.3497 (6.8); 6.3426 (6.4);

5.2988 (5.1); 4.9359 (1.3); 4.4655 (1.2); 4.4591 (1.3); 4.4534 (1.3); 4.4469 (1.2); 3.8564 (0.7); 3.8523 (0.7);

3.8345(2.2); 3.8162(2.5); 3.7981 (1.2); 3.7939 (1.2); 3.7863 (2.1); 3.7804 (2.2); 3.7728 (2.1); 3.7669 (2.4);

3.7625 (4.8); 3.7563 (2.9); 3.7487 (4.9); 3.7420 (4.7); 3.7272 (3.7); 3.7195 (1.6); 3.7054 (1.5); 3.6196 (15.1);

3.6167 (16.0); 3.5822(2.6); 3.5759 (2.2); 3.5517 (10.6); 3.5484 (11.9); 3.5446 (12.3); 3.5413 (10.3); 2.2411 (1.0); 2.2232 (1.7); 2.2200 (1.2); 2.2079 (1.3); 2.2054 (1.3); 2.2019 (1.7); 2.1902 (2.0); 2.1868 (1.5); 2.1842 (1.2); 2.1721(1.3); 2.1688 (1.9); 2.1509 (1.1); 2.0053 (0.5); 1.7305 (0.7); 1.7228 (0.8); 1.7173 (0.8); 1.7117 (1.1); 1.7036 (1.1); 1.6971 (1.0); 1.6897 (1.0); 1.6841 (0.8); 1.6779 (0.7); 1.6699 (0.6); 1.5550 (4.8); 1.2554 (1.8); 0.0689 (14.7); 0.0080 (2.4); -0.0002 (85.2); -0.0085 (2.4); -0.0501 (0.6).

Example No. I.12-71.

1 H-NMR (400.0 MHz, CDCl ₃ ): δ = 7.5355 (0.6); 7.5317 (0.6); 7.5176 (0.6); 7.5129 (0.5); 7.3540 (1.2); 7.3311 (1.2); 7.2598 (43.5); 4.1310 (0.6); 4.0497 (0.6); 4.0064 (0.7); 3.9911 (0.6); 3.9883 (0.5); 3.9809 (0.5);

3.7488 (0.6); 3.7325 (1.0); 3.7156 (1.0); 3.6957 (0.6); 3.5474 (3.2); 3.5421 (3.5); 3.5370 (1.9); 2.2520 (1.0);

2.2405 (2.6); 2.2290 (2.5); 2.2175 (0.9); 1.9789 (0.5); 1.9605 (0.6); 1.9435 (0.5); 1.9129 (0.5); 1.8807 (0.7);

1.8627 (0.8); 1.8516 (0.8); 1.8460 (0.7); 1.8335 (0.6); 1.5402 (16.0); 1.0789 (2.0); 1.0605 (3.8); 1.0421(1.7);

0.0075 (1.4); -0.0002 (15.4); -0.0084 (0.6).

- 70 042986

Example No. I.12-72.

1 H-NMR (400.0 MHz, CDCl ₃ ): δ = 7.4641 (0.9); 7.4595 (0.9); 7.4454 (0.8); 7.4407 (0.8); 7.3689 (1.3); 7.3462 (1.2); 7.2599 (46.1); 5.2985 (1.5); 3.9504 (0.6); 3.8097 (0.6); 3.7957 (0.6); 3.7761 (0.7); 3.7589 (0.6);

3.7545 (0.6); 3.7381 (0.9); 3.7304 (0.5); 3.7251 (0.8); 3.7209 (1.2); 3.7092 (1.0); 3.7043 (1.0); 3.6886 (0.6);

3.5533 (1.8); 3.5482 (4.1); 3.5427 (4.1); 3.5373 (1.6); 3.4568 (0.7); 3.4347 (0.5); 2.2518 (1.3); 2.2404(3.5);

2.2288 (3.5); 2.2173 (1.2); 1.9843 (0.5); 1.9679 (0.7); 1.9642 (0.7); 1.9495 (0.8); 1.9290 (0.6); 1.8624 (0.6);

1.8458 (0.6); 1.5585 (0.7); 1.5414 (16.0); 1.0712(2.2); 1.0528 (4.3); 1.0344 (1.9); 0.0078 (1.1); -0.0002 (17.5); -0.0085 (0.7).

Example No. I.14-72.

1H-NMR (400.0 MHz, CDCl3): δ = 7.2595 (57.5); 6.2266 (1.7); 3.5467 (1.2); 3.5415 (1.1); 2.2410 (1.0); 2.2292 (1.0); 1.5330 (16.0); 1.4813 (0.6); 0.9650 (0.7); 0.9536 (1.4); 0.9485 (1.0); 0.9399 (1.9); 0.9250 (1.3); 0.0078 (0.8); -0.0002 (22.0); -0.0080 (1.0).

Example No. I.14-91.

1H-NMR (400.0 MHz, CDCl3): δ = 7.2594 (42.0); 3.5396 (0.5); 1.5350 (16.0); 0.9566 (0.6); 0.9511 (0.6); 0.9406 (0.7); 0.9350 (0.6); -0.0002 (14.2); -0.0084 (0.6).

Example No. I.42-71.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5184 (0.9); 7.3265 (2.4); 7.3038 (2.4); 7.2907 (2.2); 7.2758 (0.6); 7.2720 (2.6); 7.2686 (1.1); 7.2678 (1.1); 7.2670 (1.3); 7.2662 (1.4); 7.2595 (171.6); 7.2092 (1.3); 6.9956 (1.0);

6.3599 (3.3); 4.0376 (2.5); 4.0274 (1.6); 4.0230 (1.9); 3.5622 (4.7); 3.5595 (4.8); 3.3916 (0.6); 3.3884 (0.6);

3.1374 (3.5); 3.1325 (3.4); 1.5744 (0.7); 1.5387(15.2); 1.5151 (0.7); 1.5038 (1.4); 1.4951 (1.1); 1.4631 (0.5);

1.3242 (16.0); 1.2841 (0.6); 1.2701 (1.1); 1.2567 (0.5); 1.2341 (0.8); 1.2195 (0.7); 1.2097 (0.8); 1.2059 (1.2);

0.0080 (2.0); -0.0002 (71.0); -0.0085 (2.2); -0.0506 (0.6).

Example No. I.42-72.

1H-NMR (400.0 MHz, CDCl3): δ = 7.3060 (3.0); 7.2836 (3.0); 7.2690 (0.5); 7.2599 (81.8); 6.9494(2.9);

6.9312 (2.9); 6.3268 (4.4); 4.0856 (0.6); 4.0680 (0.6); 4.0582 (1.0); 4.0423 (1.0); 3.9787 (0.9); 3.9756 (0.9);

3.9594 (1.0); 3.9560 (0.9); 3.9518 (0.6); 3.9486 (0.6); 3.9324 (0.6); 3.9290 (0.6); 3.7782 (0.8); 3.7636 (0.8);

3.7578 (0.6); 3.7437 (0.5); 3.7096 (0.9); 3.7063 (0.8); 3.6889 (1.5); 3.6734 (1.0); 3.6663 (0.9); 3.5364 (6.2);

3.5334 (6.5); 3.3840 (0.8); 3.3698 (0.8); 3.3630 (0.7); 3.3494 (0.7); 2.4233 (0.5); 2.2017 (16.0); 2.1577 (14.4); 1.5484 (1.4); 1.4985 (0.6); 1.4827 (0.6); 1.4668 (0.6); 1.2560 (2.7); 0.8802 (0.6); 0.8531 (0.6); 0.0080 (1.0); -0.0002 (35.4); -0.0085 (1.0).

Example No. I.48-71.

1H-NMR (400.0 MHz, CDCl3): δ = 7.3292 (2.2); 7.3067 (3.9); 7.2888 (2.0); 7.2608 (27.8); 6.3583 (3.2);

4.1147 (0.8); 4.1055(1.2); 4.0965 (0.6); 4.0888 (1.0); 4.0831(1.6); 4.0740 (0.8); 4.0704 (0.6); 4.0394 (0.9);

4.0211 (1.0); 4.0081 (0.9); 3.8519 (0.8); 3.8481 (0.8); 3.8311 (1.3); 3.8147 (0.6); 3.7679 (0.7); 3.7508 (0.6);

3.5589 (4.3); 3.1366 (3.6); 3.1328 (3.8); 1.8940 (0.9); 1.8895 (0.6); 1.8774 (0.8); 1.8735 (0.8); 1.8565 (0.6);

1.5567 (2.0); 1.3283 (16.0); 1.2700 (0.8); 1.2410 (0.6); 1.2195 (0.6); 1.2103 (0.6); 1.2058 (0.8); -0.0002 (10.8).

Example No. I.48-72.

1H-NMR (400.0 MHz, CDCl3): δ = 7.3382 (1.7); 7.3155 (1.7); 7.2963 (1.6); 7.2779 (1.7); 7.2651 (0.6);

7.2642 (0.8); 7.2601 (41.8); 6.3600 (2.5); 4.0840 (0.6); 4.0677 (0.6); 4.0569 (0.9); 4.0405 (0.9); 3.9738 (1.0);

3.9542 (1.0); 3.9467 (0.6); 3.9271 (0.6); 3.8456 (0.6); 3.8327 (0.9); 3.8156 (0.6); 3.8116 (1.0); 3.7938 (0.6);

3.7425 (0.7); 3.7235 (0.5); 3.5614 (4.0); 3.5586 (4.0); 3.5467 (0.6); 3.5384 (0.5); 3.1124 (5.6); 3.0120 (0.6);

1.3111 (16.0); 1.2929 (1.9); 1.2705 (0.7); 1.2196 (0.6); 1.2080 (0.7); 0.0079 (0.5); -0.0002 (16.4); -0.0085 (0.5).

Example No. I.48-73.

1H-NMR (400.0 MHz, CDCl3): δ = 7.3371 (0.6); 7.3145 (0.6); 7.2942 (0.7); 7.2755 (1.0); 7.2593 (74.0); 6.3593 (1.3); 3.5591 (2.1); 3.1085 (2.5); 1.5314 (16.0); 1.3083 (7.0); 1.2623 (1.1); 1.2471 (0.9); 1.2224 (1.5); 1.2071(1.6); 0.0080 (1.0); -0.0002 (28.2); -0.0084 (1.1).

Example No. I.48-81.

1H-NMR (400.0 MHz, CDCl3): δ = 7.3323 (1.9); 7.3094 (1.9); 7.3040 (1.5); 7.2856 (1.5); 7.2664 (0.6);

7.2656 (0.7); 7.2648 (0.8); 7.2639 (1.1); 7.2598 (65.4); 6.3605 (2.7); 4.1032 (0.8); 4.0835 (0.7); 4.0760 (1.1);

4.0563 (1.2); 4.0142(1.2); 3.9978 (1.3); 3.9870 (0.6); 3.9705 (0.7); 3.5633 (4.1); 3.5603 (4.3); 3.1239 (3.7);

3.1224(3.9); 2.8527 (0.6); 2.8378 (0.6); 2.0039 (0.8); 1.9975 (0.7); 1.9929 (1.1); 1.9892 (1.4); 1.9831 (0.8);

1.9807 (0.8); 1.9772 (0.7); 1.9739 (0.9); 1.7617 (0.5); 1.5482 (1.5); 1.3181 (16.0); 0.0080 (0.8); -0.0002 (25.8); -0.0085 (0.7).

Example No. I.48-82.

1H-NMR (400.0 MHz, CDCl3): δ = 7.3366 (1.2); 7.2593 (67.6); 7.2564 (64.9); 7.2508 (34.0); 6.3598 (1.6); 4.0843 (0.7); 4.0355 (0.6); 3.5596 (3.8); 3.1158 (2.7); 2.8813 (1.0); 2.8630 (1.4); 2.5976 (0.6); 2.1008 (0.6); 1.5306 (16.0); 1.5277 (15.3); 1.5221 (8.1); 1.3151 (7.9); -0.0002 (24.0); -0.0031 (23.2); -0.0087 (12.6).

Example No. I.48-91.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5184 (0.9); 7.3265 (2.4); 7.3038 (2.4); 7.2907(2.2); 7.2758 (0.6); 7.2720 (2.6); 7.2686 (1.1); 7.2678 (1.1); 7.2670 (1.3); 7.2662 (1.4); 7.2595 (171.6); 7.2092 (1.3); 6.9956 (1.0); 6.3599 (3.3); 4.0376 (2.5); 4.0274 (1.6); 4.0230 (1.9); 3.5622 (4.7); 3.5595 (4.8); 3.3916 (0.6); 3.3884 (0.6);

- 71 042986

3.1374 (3.5); 3.1325 (3.4); 1.5744 (0.7); 1.5387(15.2); 1.5151 (0.7); 1.5038 (1.4); 1.4951 (1.1); 1.4631 (0.5);

1.3242 (16.0); 1.2841 (0.6); 1.2701 (1.1); 1.2567 (0.5); 1.2341 (0.8); 1.2195 (0.7); 1.2097 (0.8); 1.2059(1.2); 0.0080 (2.0); -0.0002 (71.0); -0.0085 (2.2); -0.0506 (0.6).

Example No. I.48-93.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5183 (0.7); 7.3344 (1.5); 7.3117 (1.6); 7.2861 (1.7); 7.2594(115.4); 6.9954 (0.6); 6.3597 (2.6); 3.9796 (0.6); 3.9694 (0.6); 3.9501 (0.7); 3.9418 (0.7); 3.9197 (2.6); 3.9036(2.6);

3.5617 (4.0); 3.5591 (3.9); 3.4026 (0.6); 3.3973 (0.7); 3.3731 (1.2); 3.3681 (1.2); 3.3437 (0.6); 3.3387 (0.6);

3.1160 (5.2); 2.0436 (1.1); 1.6081 (0.6); 1.5766 (0.8); 1.5325 (15.9); 1.3793 (0.6); 1.3676 (0.6); 1.3464 (0.6);

1.3345 (0.7); 1.3177 (16.0); 1.2897 (0.5); 1.2765 (0.5); 1.2587 (1.3); 0.0080 (1.7); -0.0002 (44.1); -0.0085 (1.4).

Example No. I.48-121.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5182 (0.5); 7.3372 (1.1); 7.3281 (0.6); 7.3234 (0.6); 7.3145 (1.1); 7.3051 (0.6); 7.2594 (86.1); 6.3602 (1.6); 3.8787 (0.6); 3.8738 (0.6); 3.8675 (0.6); 3.8352 (0.5); 3.5596 (2.7); 3.1196 (1.0); 3.1166 (1.0); 3.1113 (1.1); 3.1080 (1.0); 3.0915 (0.6); 1.5312 (16.0); 1.3010 (7.9); 1.2943 (2.5); 1.2586 (0.5); 1.2026 (2.0); 0.8819 (0.6); 0.0079 (1.0); -0.0002 (33.9); -0.0085 (1.4).

Example No. I.48-221.

1H-NMR (400.0 MHz, CDCl3): δ = 7.3103 (0.9); 7.2876 (1.0); 7.2594 (77.1); 6.3567 (1.2); 3.5597 (1.8); 3.5569 (1.8); 3.1559 (0.5); 3.1446 (0.5); 3.1241 (0.5); 1.5359 (16.0); 1.3178 (3.1); 1.3132 (2.1); 1.3074 (1.7); 0.0079 (1.1); -0.0002 (28.7); -0.0085 (1.0).

Example No. I.49-71.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5196 (0.7); 7.4294 (4.1); 7.4269 (4.4); 7.4107 (4.2); 7.4082 (4.4); 7.3731 (8.2); 7.3501 (8.2); 7.2728 (0.5); 7.2721 (0.6); 7.2712 (0.6); 7.2705 (0.7); 7.2696 (0.8); 7.2689 (0.9); 7.2680 (1.0); 7.2672 (1.2); 7.2664 (1.4); 7.2656 (1.7); 7.2648(2.2); 7.2607 (122.4); 6.9966 (0.7); 6.3693 (1.3); 6.3586 (6.3); 6.3546(6.2); 4.1857 (1.4); 4.1770 (1.7); 4.1735 (1.1); 4.1709 (1.0); 4.1651 (1.1); 4.1626 (1.2);

4.1579 (1.7); 4.1492(2.6); 4.1461 (1.4); 4.1436 (1.2); 4.1376 (1.8); 4.1353 (1.8); 4.1282 (0.5); 4.1207 (0.7);

4.1113 (1.5); 4.1039 (1.7); 4.0943 (1.6); 4.0863 (1.8); 4.0792 (1.3); 4.0690 (0.8); 4.0621 (0.6); 4.0365 (2.1);

4.0203 (3.9); 4.0090 (1.4); 4.0034 (1.9); 3.9925 (2.8); 3.9756 (1.4); 3.8871 (0.8); 3.8832 (0.7); 3.8700 (1.6);

3.8662 (2.5); 3.8627 (1.2); 3.8535 (1.0); 3.8492 (3.0); 3.8455 (2.0); 3.8325 (1.1); 3.8284 (1.0); 3.7965 (1.0);

3.7927 (0.9); 3.7764 (2.0); 3.7586 (1.8); 3.7422 (0.6); 3.7042 (1.1); 3.6887 (1.7); 3.6835 (1.4); 3.6719 (1.5);

3.6682 (1.8); 3.6514 (1.2); 3.5631 (11.1); 3.5600 (16.0); 3.5569 (11.6); 2.7333 (1.6); 2.7185 (1.7); 2.6938(2.6); 2.6790 (2.6); 2.5796 (3.0); 2.5764 (1.6); 2.5589 (2.8); 2.5557 (1.5); 2.5401 (1.8); 2.5370 (1.0); 2.5194 (1.7);

2.5163 (0.9); 2.0187 (0.7); 2.0140 (0.8); 2.0016 (1.3); 1.9944 (0.9); 1.9896 (0.8); 1.9808 (1.7); 1.9730 (0.8);

1.9683 (1.3); 1.9512 (1.2); 1.9363 (0.7); 1.9331 (0.8); 1.9246 (1.1); 1.9163 (1.4); 1.9072 (3.1); 1.9034 (1.8);

1.9001 (1.7); 1.8907 (2.8); 1.8871 (2.4); 1.8728 (1.4); 1.8699 (2.1); 1.8524 (0.8); 1.6316 (0.5); 1.6236 (0.8);

1.6134 (1.1); 1.6096 (0.9); 1.6015 (1.1); 1.5919 (1.5); 1.5833 (1.2); 1.5743 (1.3); 1.5572 (8.3); 1.3735 (16.0);

1.3566 (15.6); 1.2562 (0.9); 0.0080 (1.5); -0.0002 (47.8); -0.0085 (1.3).

Example No. I.49-72.

1H-NMR (400.0 MHz, CDCl3): δ = 7.4106 (1.7); 7.4041 (2.3); 7.4005 (2.0); 7.3919 (1.8); 7.3854 (2.5);

7.3803 (6.7); 7.3573 (6.1); 7.2683 (0.5); 7.2674 (0.6); 7.2666 (0.7); 7.2658 (0.9); 7.2650 (1.2); 7.2642 (1.6);

7.2608 (84.6); 7.2544 (0.8); 7.2536 (0.6); 7.2528 (0.5); 6.3611 (5.5); 4.1353 (0.6); 4.1308 (0.6); 4.1189 (0.7);

4.1145 (1.5); 4.1082 (1.0); 4.1036 (1.0); 4.0983 (1.0); 4.0917 (1.0); 4.0874 (2.4); 4.0712 (1.5); 4.0250 (1.1);

4.0216 (1.1); 4.0054 (1.2); 4.0011 (1.5); 3.9971 (1.5); 3.9770 (1.4); 3.9697 (0.8); 3.9531 (0.7); 3.9496 (0.7);

3.8716 (0.9); 3.8576 (1.0); 3.8508 (2.0); 3.8366 (3.3); 3.8302 (1.5); 3.8170 (3.7); 3.7955 (1.9); 3.7629 (1.2);

3.7437(2.6); 3.7244 (2.0); 3.7051 (0.9); 3.6919 (1.1); 3.6751 (1.5); 3.6715 (1.4); 3.6548 (1.6); 3.6393 (1.1);

3.5730 (2.8); 3.5637 (9.4); 3.5603 (14.9); 3.5571 (10.6); 3.5533 (4.2); 3.5372 (2.2); 2.7027 (0.6); 2.6980 (0.8); 2.6926 (0.6); 2.6879 (0.6); 2.6835 (0.8); 2.6775 (0.6); 2.6633 (1.0); 2.6587 (1.3); 2.6533 (1.1); 2.6486 (1.0);

2.6439 (1.3); 2.6383 (0.9); 2.5794 (0.9); 2.5615 (1.1); 2.5423 (2.0); 2.5389 (2.5); 2.5354 (1.4); 2.5219 (1.4);

2.5184 (2.1); 2.5147 (1.2); 2.5030 (0.8); 2.4996 (1.3); 2.4961 (0.8); 2.4827 (0.8); 2.4791 (1.3); 2.4754 (0.8);

2.0520 (0.8); 2.0389 (1.1); 2.0296 (0.8); 2.0201(1.2); 2.0070 (0.8); 1.6590 (0.7); 1.6413 (1.1); 1.6271 (1.4);

1.6074 (1.4); 1.5925 (1.1); 1.5748 (2.4); 1.3725 (16.0); 1.3555 (15.6); 1.2557 (0.8); 0.0080 (1.0); -0.0002 (35.6); -0.0085 (1.0).

Example No. I.49-91.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5192 (1.1); 7.4199 (3.9); 7.4168 (3.7); 7.4122 (0.8); 7.4012 (3.9);

7.3981 (3.6); 7.3894 (0.6); 7.3718 (6.7); 7.3489 (6.7); 7.2748 (0.5); 7.2740 (0.6); 7.2732 (0.6); 7.2717 (0.8);

7.2708 (0.9); 7.2701 (1.0); 7.2692 (1.1); 7.2685 (1.3); 7.2677 (1.4); 7.2668 (1.7); 7.2660 (2.0); 7.2652 (2.5);

7.2644 (3.2); 7.2603 (192.6); 7.2539 (1.5); 7.2514 (0.5); 6.9963 (1.1); 6.4032 (0.6); 6.3602 (5.9); 6.3561 (6.0);

5.9753 (1.4); 4.1184(1.2); 4.1100 (1.4); 4.0981 (0.7); 4.0894 (2.4); 4.0810 (2.5); 4.0781 (1.9); 4.0691(1.6);

4.0522(2.6); 4.0355 (2.7); 4.0323 (1.6); 4.0302 (1.5); 4.0231 (0.9); 4.0147 (1.5); 4.0127 (1.5); 4.0064 (1.5);

4.0009 (1.7); 3.9951 (1.4); 3.9859 (1.4); 3.9714 (1.3); 3.9671 (1.3); 3.9612 (1.2); 3.7055 (1.0); 3.6905 (1.5);

3.6735 (1.4); 3.6694 (1.6); 3.6529 (1.1); 3.5949 (0.9); 3.5917 (1.0); 3.5642 (10.4); 3.5610 (15.2); 3.5576 (11.4); 3.5298 (1.1); 3.5210 (1.0); 3.5036 (1.0); 3.4972 (0.7); 3.4451 (1.1); 3.4407 (1.0); 3.4174 (1.9); 3.4127 (1.5);

3.3889 (0.9); 2.7355 (1.2); 2.7226(1.2); 2.6957 (2.0); 2.6813 (1.9); 2.5817 (2.3); 2.5607(2.2); 2.5422 (1.5);

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2.5213 (1.4); 1.8716 (1.1); 1.8589 (0.9); 1.8426 (0.9); 1.7458 (1.0); 1.7284 (1.0); 1.5951 (1.4); 1.5627 (4.3);

1.5527 (4.0); 1.5347 (4.4); 1.5247 (3.8); 1.5179 (4.0); 1.5098 (3.1); 1.4869 (1.8); 1.4780 (1.5); 1.4685 (0.7);

1.4474 (0.5); 1.3679 (16.0); 1.3510 (15.7); 1.3238 (1.0); 1.3092 (0.9); 1.2951 (0.8); 1.2846 (0.7); 1.2558 (1.6);

0.0080 (2.6); 0.0064 (0.9); 0.0056 (1.0); 0.0048 (1.2); 0.0039 (1.5); -0.0002 (78.4); -0.0067 (0.7); -0.0084 (2.1).

Example No. I.54-71.

1H-NMR (400.0 MHz, CDCl3): 1H-NMR (400.0 MHz, CDCI3): δ = 7.3208 (1.3); 7.2979 (1.7); 7.2912 (1.7); 7.2726 (2.6); 7.2593(70.2); 4.0864 (0.7); 3.5567 (1.6); 3.5515 (1.5); 3.1329 (1.5); 3.1297 (1.5); 2.2606 (0.5); 2.2492 (1.4); 2.2378 (1.5); 2.2262 (0.5); 1.5330 (16.0); 1.3269 (6.7); -0.0002 (24.8); -0.0084 (0.8).

Example No. I.54-82.

1H-NMR (400.0 MHz, CDCl3): δ = 7.5183 (0.5); 7.3313 (1.4); 7.3086 (1.5); 7.2883 (1.4); 7.2697 (1.9);

7.2594 (89.8); 5.2984 (0.6); 4.0886 (0.6); 4.0728 (0.6); 4.0707 (0.6); 4.0401 (0.6); 4.0245 (0.6); 3.5636 (1.1);

3.5585 (3.1); 3.5531 (3.2); 3.5477 (1.2); 3.1156 (4.8); 2.9201 (0.6); 2.9102 (0.6); 2.8940 (0.6); 2.8830 (1.3);

2.8686 (1.5); 2.8636(1.5); 2.8492 (1.3); 2.6274 (0.6); 2.6084 (0.7); 2.5822 (0.7); 2.2619 (0.8); 2.2504 (2.7);

2.2389 (2.9); 2.2274 (1.0); 1.5303 (16.0); 1.3159 (14.4); 0.0080 (1.1); -0.0002 (35.1); -0.0085 (1.4).

Example No. I.54-221.

Diastereomer 1 - 1H-NMR (400.0 MHz, CDCl ₃ ): δ = 7.3038 (3.1); 7.2871 (1.2); 7.2813 (2.5); 7.2599 (71.2); 5.2983 (2.7); 3.9383 (0.5); 3.8513 (0.7); 3.8472 (0.6); 3.8308 (0.9); 3.7432 (0.9); 3.7266 (0.6); 3.7227 (0.6); 3.5559 (4.7); 3.5505 (4.9); 3.5451 (1.9); 3.1943 (0.6); 3.1787 (0.8); 3.1742 (0.7); 3.1486 (1.5); 3.1439 (1.6); 3.1151 (1.5); 3.1107 (1.4); 3.0847 (0.6); 3.0805 (0.6); 2.2599 (1.2); 2.2485 (3.9); 2.2369 (4.1); 2.2254 (1.4); 1.9451 (0.5); 1.9179 (0.8); 1.9023 (1.2); 1.8833 (1.3); 1.8662 (0.8); 1.5497 (16.0); 1.3156 (8.3); 1.3076 (7.1); 1.2954 (0.5); 1.1850 (0.5); 0.0080 (0.8); -0.0002 (26.3); -0.0084 (0.9). Diastereomer 2 - 1H-NMR (400.0

MHz, CDCl3): δ = 7.3105 (0.7); 7.3038 (5.6); 7.2870 (2.3); 7.2837 (2.7); 7.2812 (4.5); 7.2601 (82.6); 6.1429 (0.8);

(1,2);

(0.6);

(0.7);

(0.6);

(2.8);

(7.7);

5.2984 (6.5); 3.9465 (0.9);

3.8349 (0.9); 3.8307 (1.8);

3.5608 (3.0); 3.5558 (8.8);

3.5125 (0.7); 3.5083 (0.7);

3.1941 (1.1); 3.1899 (0.6);

3.1438 (3.0); 3.1151 (2.8);

2.2253 (2.6); 2.0434 (1.8);

3.9382 (0.9);

3.8144 (0.9);

3.5504 (9.1);

3.5058 (0.6);

3.1786 (1.5);

3.1106 (2.6);

1.9626 (0.7);

3.9292

3.7606

3.5450

3.4999

3.1742 3.0848 1.9452 (0.9);

(0.9);

(3.6);

(0.6);

(1.4);

(1.0);

(1.0);

3.9207 3.7433 3.5344

3.4972

3.1637 3.0803 1.9332 (0.9);

(1.7);

(0.6);

(0.6);

(0.6);

(1,1);

(0.8);

3.8682 (0.7); 3.8512 (1.4);

3.7266 (1.1); 3.7230 (1.1);

3.5236 (0.6); 3.5210 (0.6);

3.2110 (0.6); 3.2072 (0.6);

3.1596 (0.9); 3.1552 (0.6);

2.2598(2.2); 2.2484 (7.3);

1.9178 (1.6); 1.9022 (2.4);

3.8472

3.7062

3.5152

3.1983

3.1485

2.2368

1.8833 (2.5); 1.8663 (1.5); 1.5585 (9.3); 1.5390 (0.9); 1.5198 (0.7); 1.3155 (16.0); 1.3075 (12.5); 1.2764 (0.7); 1.2585 (1.5); 1.2407 (0.6); 0.0080 (1.0); -0.0002 (30.8); -0.0083 (1.2).

Example No. I.60-72.

1H-NMR (400.0 MHz, CDCl·,): δ = 7.4902 (1.0); 7.4720 (1.0); 7.3788 (1.2); 7.3563 (1.2); 7.2601 (25.5);

3.9388 (0.6); 3.9266 (0.7); 3.9208 (0.6); 3.9086 (0.7); 3.9023 (0.6); 3.8099 (0.7); 3.7955 (0.7); 3.7748 (0.8);

3.7559 (0.8); 3.7347 (0.9); 3.7166 (0.8); 3.5418 (3.1); 3.5362 (3.0); 3.4569 (0.6); 3.4343 (0.5); 2.7202 (0.7);

2.7131 (0.8); 2.7030 (0.8); 2.6947 (0.7); 1.5374 (16.0); 1.5144 (3.9); 1.1448 (1.8); 1.1265 (3.4); 1.1080 (1.6);

-0.0002 (31.4); -0.0083 (1.2).

Example No. I.60-91.

1H-NMR (400.0 MHz, CDCI3): δ = 7.5351 (0.7); 7.3697 (0.8); 7.3570 (0.8); 7.3456 (0.8); 7.3351 (0.9); 7.2601 (21.1); 7.2584 (18.4); 4.0615 (0.5); 3.9939 (0.7); 3.9325 (1.0); 3.5401 (3.4); 3.3978 (0.5); 3.3753 (0.6); 2.7173 (0.9); 1.8352 (0.5); 1.5375 (16.0); 1.5185 (2.7); 1.5086 (2.4); 1.4872 (1.8); 1.2587 (0.6); 1.1470 (1.7); 1.1285 (2.9); 1.1109 (1.3); -0.0002 (25.4); -0.0019 (21.9).

Example No. I.60-221.

1H-NMR (400.0 MHz, CDCI3): δ = 7.3528 (0.6); 7.3419 (0.5); 7.3300 (0.6); 7.3202 (0.5); 7.2603 (26.0); 3.8155 (0.6); 3.7989 (0.6); 3.5293 (2.0); 3.5237 (1.3); 2.0449 (1.4); 1.6044 (1.6); 1.5879 (2.1); 1.5706 (1.7); 1.5435 (16.0); 1.2771 (0.5); 1.2592 (1.1); 1.1388 (0.6); 1.1257(1.3); 1.1216(1.2); 1.1075 (0.7); 0.8819 (0.6); 0.0080 (0.9); -0.0002 (30.9); -0.0085 (1.6).

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 preferred or especially preferred, in particular one or more compounds of formula (1.1) -(1.60) 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 (1.1)-(1.60) 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 of (harmful) plants , the soil in which or on which (harmful) plants grow, or the cultivated area.

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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.60) 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 unwanted crop plants), seeds of unwanted plants (i.e. seeds of plants, e.g. grains, seeds or organs of vegetative propagation such as tubers or parts of shoots with buds), soil in which or on which unwanted plants grow (e.g. arable land or non-arable land), or crop area (i.e. area in which 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.60) 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 i.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. e. the area in which the 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, in the pre-planting stage (perhaps even by application to the soil), pre-emergence and/or post-emergence. 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.

Monocotyledons of the genus Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. Dicotyledonous 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), the emergence of shoots of weeds and/or shoots of broadleaf weeds is completely prevented, or the weeds grow until they reach the cotyledon stage, but then they stop growing and eventually die permanently after three to four weeks.

If the active ingredients are applied post-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 period of time so that competition from weeds that are harmful to crops plants are thus eliminated very early and for a long time.

Although the compounds of the present invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, cultivated plants of economically important crops, for example 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,

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Triticum, Zea, will be damaged only slightly, 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 influence 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 general control and suppression of unwanted vegetative growth without destroying 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 respect to transgenic crops, preference is given to the use of the compounds of the present invention and/or their salts 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 crops of useful plants that are or have been recombinantly resistant 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 species, 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) can also preferably be used as herbicides in crops of useful plants that are or have been recombinantly resistant 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

- 75 042986 properties. 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, it is possible, for example, to perform base substitutions, remove part of the sequences, or add natural or synthetic sequences. 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 or 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 suppression 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 (HPPD), or 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, modified or specifically an expanded range of weeds that can be controlled, modified application rates that can be used for application, preferably good compatibility with herbicides to which the transgenic crop is resistant, and effects on the growth and yield of transgenic crops.

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 application to 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 contemplates the use of one or more compounds of formula (I) or salts thereof or a composition according to the present invention (as defined below) (in a method) for the control of harmful plants or for the regulation of plant growth, wherein 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.

- 76 042986

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. The present invention therefore also provides herbicidal compositions and plant growth control compositions containing compounds of formula (I) and/or salts thereof.

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 microgranule form, 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 Adducts], 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 evenly 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, polyglycol ether sulfates of fatty alcohols, 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.

- 77 042986 solvents, with the addition of one or more ionic and / or non-ionic 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 , 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, pages 147ff; Perry's Chemical Engineer's Handbook, 5th ed., McGraw-Hill, New York 1973, p. 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 Scientific Publications, Oxford, 1968, p. 101-103.

The agrochemical preparations, preferably the herbicidal or plant growth regulating compositions of the present invention preferably contain in total 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 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 wt.%, the balance up to 100 wt.% consists of traditional components of the composition. 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 wt.%, preferably from 2 to 50 wt.% of the active ingredient. In the case of water-dispersible granules, the active ingredient content 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 wt.%, preferably from 10 to 80 wt.%.

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 as their preparations (compositions) with other pesticide substances, for example insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example in the form finished composition or in the form of tank mixtures. Combined compositions can be obtained in this case based on the above compositions, taking into account the physical properties and

- 78 042986 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, the action of which is based on the inhibition of, for example, acetolactate synthase, acetyl-CoA-carboxylase, cellulose synthases, enolpyruvylshikimate-3-phosphate synthases, glutamine synthetases, p-hydroxyphenylpyruvate dioxygenases, phytoene desaturases, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.

Of particular interest is the selective control of harmful plants in crops of useful 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 applied herbicides/pesticides, for example in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet/sorghum), sugar beet, sugarcane, 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 corresponding 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, 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 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. 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-soua-carboxylase, cellulososyntase, enolpirivikim-3-phosphatase, glutaminsyntase, p-hydroxyphenilpyuruvatexygenase, phytoenesiac, photosystems II or 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 or their common name in English, in accordance with the norms 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, and all isomeric forms, such as stereoisomers and optical isomers, even if not explicitly stated.

Components for forming a combination applicable with the compounds of 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, phydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, or protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 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, and all isomeric forms, such as stereoisomers and optical isomers, even if not explicitly stated.

Examples of such herbicidal components for the formation of the mixture are acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxidim, alloxydim-sodium, ametrin, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid , amitrol, ammonium sulfamate, anilophos, asulam, atrazine, azaphenidin, azimsulfuron, beflubutamide, benazoline, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclone, benzofenap, bicyclopyrone, bifenox, bilanafos , bilanafos-sodium, bispyribac , bispyribac-sodium, bromacyl, bromobutide, bromophenoxime, bromoxynil, bromoxynyl-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacyl, butamiphos, butenachlor, butralin, butroxydim, butylate, cafenstrol, carbetamide, carfentrazone, carfen trazon- ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazone, chlorimuron, chlorimuron-ethyl, chlorphthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cynidone, cinidone-ethyl, cinmethylin, cinosulfuron, claci phos, cletodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumiluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxidim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4D-butotyl, -butyl, -dimethylammonium,

-diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium,

-triisopropanolammonium and -trolamine, 2,4-DB, 2,4-OB-6util, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dimron), dalapon, dazomet, n-decanol, desmedifam, detosyl pyrazolate ( DTP), dicamba, dichlobenyl, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4dimethyl-1,2 -Oxazolidin-3-O, dichlorprop, dichlorprop-r, diklofop, diclofop-methyl, dikonfop-romethyl, diclosulam, diphenovokvat, diplufenican, diplufenzopir, diplufenzopir-natrium, disteephuron, dimipipetamlore, dimetametrin, dimetenamid, dimetenamida, dimetenamida, dimetenamida, dimetenamida, dimetenamida, dimetenamida, dimetenamida, dimetenamida, dimetenamida Dr., dimetrisufuron , dinitramine, dinoterb, diphenamide, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, etalfluralin, etametsulfuron, etametsulfuron-methyl, etiosin, etofumesate, ethoxyphene, ethoxyphen-ethyl, ethoxysulfuron, etobenzanide, F-9600 , F-5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5dihydro-5-oxo-1H-tetrazol-1-yl]phenylethanesulfonamide, F-7967, i.e. 3-[7-Chloro-5-fluoro-2(trifluoromethyl)-1 H-benzimidazol-4-yl] -1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1 H,3H)-dione, fenoxaprop , fenoxaprop-R, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrion, fentrazamid, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop- P , fluazifop-butyl, fluazifop-Rbutyl, flucarbazone, flucarbazone-sodium, flusetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine, fluometuron, flurenol, flurenol-butyl, -di methylammonium and -methyl , fluoroglycofen, fluoroglycophen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, flutiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, ammonium glufosinate , glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, i.e. . O-(2,4-dimethyl-6-nitrophenyl)-O-ethylisopropylphosphoramidothioate, galauxifen, galauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxifop, haloxifop-R, haloxifop-ethoxyethyl, haloxifop-P-ethoxyethyl, haloxifop-methyl, haloxyfop-P-methyl, hexazinon, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4dichlorophenoxy)acetate, imazametabenz, imazametabenz-methyl, imazamox, imazamox-ammonium, imazapik, - 80 042986 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)-1-methyl-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, mecoprop-sodium and -butotyl, mecoprop-R, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, metabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, metabenzthiazuron, methiopyrsulfuron, methiozolin, methylisothiocyanate, metobromuron, metolachlor, S-metolachlor, methosulam, methoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, i.e. Ν-[3-χλορ-4-(1methylethyl)-phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazone, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxacyclomefone, oxotrione (lancotrione), oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxulam, pentachlorophenol, pentoxazone, petoxamide, petroleum oils, phenmedifam, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxidim, prometon , promethrin, propachlor, propanil, propaquizafop, propazine, profam, propisochlor, propoxycarbazone, propoxycarbazone sodium, propyrisulfuron, propizamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotol, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl , pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxime, pyributicarb, pyridafol, pyridate, pyrifthalide, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobacsodium, pyroxasulfone, piroxulam, quinclorac, quinmerac, kv inoclamin, quizalofop, quizalofopethyl, quizalofop- P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, setoxydim, siduron, simazine, symetrin, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chloro-4(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i. e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-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, thifensulfuron-methyl, thiobencarb, thiafenacil, tolpyralate, topramesone, tralkoxydim, triafamone, triallat, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron sodium, trifludimoxazine, triflura lin, triflusulfuron, triflusulfuron- methyl, tritosulfuron, urea sulfate, vernolate, ZJ-0862, i.e. 3,4-dichloroN-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline and the following compounds:

Examples of plant growth regulators as possible components for the formation of a mixture are acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1enyl)propionic acid, daminoside, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dicalium, -disodium and MOHO(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide , indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2(1-naphthyl)acetamide , 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazen, thidiazuron, triacontanol, trinexapak, trinexapak-ethyl, cytodef, uniconazole, uniconazole-R.

Also components for forming a combination with compounds of formula (I) in accordance with the present invention may include, 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,

- 81 042986 ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) (mefenpyrdiethyl) and related compounds as described in WO-A -91/07874;

S1 ^b ) derivatives of dichlorophenylpyrazolecarboxylic acid (S1 ), 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-diphenyl-2-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-quinolineoxyacetate (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, as well as (5-chloro-8-quinolinoxy)acetic acid (S2-10), hydrates and their salts, for example their salts 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 (5-chloro-8-quinolinoxy)malonic acid type (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. dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S32), R-28725 (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), benoxacor (4dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), PPG-1292 (N-allyl-N-[(1,3-dioxolan2-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 (3dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) from Nitrokemia or Monsanto (S3-7), TI -35 (1dichloroacetylazepane) from TRI-Chemical RT (S3-8), Diclonon (dicyclonone) or BAS145138 or LAB145138 (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) (S310) and the (R) isomer of each them (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 represents (C 1 -C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, where the last 2 radicals are substituted v _A with substituents from the group consisting of halogen, (C ₁ -C ₄ )alkoxy, (C 1 - C ₆ )haloalkoxy and (C1-C ₄ )alkylthio, and, in the case of cyclic radicals, also (C ₁ -C ₄ )alkyl and (C ₁ -C ₄ )haloalkyl;

RA ² is halo, (C ₁ -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 RB ¹ , RB ² independently represent hydrogen, (C1-C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, (C ₃ - 82 042986

C ₆ ) alkenyl, (C3-C ₆ ) alkynyl,

RB3 is halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )haloalkyl or (C ₁ -C ₄ )alkoxy and m _B is 1 or 2, for example, compounds in which

RB ¹ = cyclopropyl, RB ² = hydrogen and (RB3) = 2-OMe (cyprosulfamide, S4-1),

RB ¹ = cyclopropyl, RB ² = hydrogen and (RB3) = 5-Cl-2-OMe (S4-2),

RB ¹ = ethyl, RB ² = hydrogen, and (RB3) = 2-OMe (S4-3),

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

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

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

in which RC ¹ , RC ² independently represent hydrogen, (C1-C ₈ )alkyl, (C ₃ -C ₈ )cycloalkyl, (C ₃ C ₆ )alkenyl, (C ₃ -C ₆ )alkynyl,

RC ³ is halogen, (C ₁ -C ₄ )alkyl, (C 1 -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, CF3;

mD is 1 or 2;

RD is hydrogen, (C _g C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, (C ₂ -C ₆ )alkenyl, (C ₂ -C ₆ )alkynyl, (C3 -C6)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 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, thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3 ( 2-thienyl)-1,2-dihydroquinoxalin-2-one as described in WO-A-2005/112630;

S7) compounds from the class of diphenylmethoxyacetic acid derivatives (S7), for example methyldiphenylmethoxyacetate (CAS Registry No. 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 halogen, (C ₁ -C ₄ )alkyl, (C ₁ -C ₄ )haloalkyl, (C ₁ -C ₄ )alkoxy, (C _r C ₄ )haloalkoxy,

RD ² is hydrogen or (C ₁ -C ₄ )alkyl,

RD ³ is hydrogen, (C ₁ -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 no 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 (registration

- 83 042986 CAS number 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 ) wherein RE ¹ is halogen, (C ₁ -C ₄ )alkyl, methoxy, nitro, cyano, CF ₃ , OCF ₃ , YE, ZE are independently O or S, n _E is is an integer from 0 to 4,

RE ² is (C ₁ -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 dressings, 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) ( S11-2), 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 millet/sorghum seeds 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,

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]decane4-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 their herbicidal action against weeds, also exhibit an antidote action against cultivated plants such as rice, for example dimepiperate or MY-93 (S-1-methyl-1-phenylethylpiperidine-1-carbothioate), which are 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 are known as antidotes 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 number 5409106-4), which is known as an antidote for certain herbicide damage in rice;

- 84 042986

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

as described in WO-A-2008/131861 and WO-A-2008/131860, wherein RH ¹ is a (C1-C ₆ ) haloalkyl radical and RH ² is hydrogen or halogen, and

RH ³ , RH ⁴ are independently 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 a group consisting of halogen, hydroxyl, cyano, (C1-C ₄ )alkoxy, (C1C ₄ )haloalkoxy, (C ₁ -C ₄ )alkylthio, (C1-C ₄ )alkylamino, di[(C1-C ₄ )alkyl ]amino, [(C ₁ -C ₄ )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 to 6 membered saturated or unsaturated carbocyclic ring, or (C ₄ -C ₆ )cycloalkenyl fused on one side of the ring with a 4-6 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, (C ₁ -C ₄ )alkoxy, (C1C ₄ )haloalkoxy, (C1-C ₄ )alkylthio, (C1-C ₄ )alkylamino, di[ (C 1 -C ₄ )alkyl]amino, [(C 1 -C ₄ )alkoxy]carbonyl, [(C ₁ -C ₄ )haloalkoxy]carbonyl, (C ₃ -C ₆ )cycloalkyl which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or

RH ³ is (C1-C4)alkoxy, (C2-C4)alkenyloxy, (C2-C6)alkynyloxy, or (C2C4)haloalkoxy, and

RH ⁴ is hydrogen or (C1-C ₄ )alkyl or

RH ³ and RH ⁴ together with the directly bonded nitrogen atom represent a 4-8 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-C ₄ )alkyl, (C1-C ₄ ) haloalkyl, (C1-C ₄ )alkoxy, (C1C ₄ )haloalkoxy, and (C1- _C4 )alkylthio;

S16) active ingredients which are used primarily as herbicides, but which also have an antidote effect on cultivated plants, e.g. (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R ,S)-2-(4-chloro-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-(4chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1(ethoxycarbonyl)ethyl-3,6-dichloro-2 -methoxybenzoate (lactidichloro-ethyl).

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.60) and/or their salts, are cloquintoset-mexil, cyprosulfamide, fenchlorazole-ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumiluron, S4-1 and S4-5, and particularly preferred antidotes are cloquintoset-mexil, cyprosulfamide, isoxadifen-ethyl 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 loam soil in plastic or wood fiber pots, covered with earth and grown under controlled growth conditions in a greenhouse. The test plants were treated at the single leaf stage 2-3 weeks after planting. 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-A15 below shows the efficacy values of selected compounds of general formula (I)

- 85 042986 in accordance with the table. I.1-I.60 against various noxious plants and the application rate corresponding to 80 g/ha or below, which was obtained using the above test method.

Table A1

Compound, Example No. Alopecurus myosuroides (Efficacy in %) Application rate [g/ha] 1.2-72 90 80 1.1-73 90 80 1.48-71 90 80 1.1-26 80 80 1.1-222 90 80 1.1-221 90 80 1.1-341 90 80 1.1-27 90 80 1.48-72 90 80 1.8-271 100 80 1.1-2 90 80 1.1-271 100 80 1.1-1 80 80 1.1-275 90 80 1.1-224 80 80 1.1-115 80 20 1.2-336 80 20 1.2-92 80 20 1.2-91 90 20 1.6-71 80 20 1.6-221 90 20 1.12-91 80 20 1.48-93 80 20 1.48-121 80 20 1.1-181 80 80 1.1-51 80 20

- 86 042986

Table A2

Compound, Example No. Echinochloa crus-galli (Efficacy %) Application rate [g/ha] 1.2-72 100 80 1.1-73 100 80 1.48-71 100 80 1.1-26 100 80 1.1-222 100 80 1.1-221 100 80 1.1-341 100 80 1.1-27 100 80

1.48-72 100 80 1.8-271 80 80 1.1-2 100 80 1.1-72 100 80 1.1-271 90 80 1.1-71 100 80 1.1-1 100 80 1.1-275 90 80 1.8-1 100 80 1.1-6 90 20 1.1-30 100 20 1.2-71 80 20 1.48-81 90 20 1.48-91 100 20 1.42-72 90 20 1.2-92 100 20 1.2-91 100 20 1.2-81 100 20 1.6-71 90 20 1.6-72 80 20 1.5-71 90 20 1.5-72 90 20 1.5-221 80 20 1.5-91 80 20 1.6-221 80 20 1.4-221 80 20 1.12-71 100 20 1.12-91 100 20 1.12-72 100 20 1.54-71 80 20 1.1-181 100 20 1.1-82 100 20 1.1-92 100 20 1.1-123 100 20 1.1-41 100 20 1.1-121 100 20 1.1-51 100 20 1.1-48 100 20

- 87 042986

Table A3

Compound, Example No. Setaria viridis (Efficacy in %) Application rate [g/ha] 1.2-72 100 80 1.1-73 100 80 1.48-71 100 80 1.1-26 100 80 1.1-222 100 80 1.1-221 100 80 1.1-341 100 80 1.1-27 100 80 1.48-72 100 80 1.8-271 100 80 1.1-2 100 80 1.1-72 100 80 1.1-271 100 80 1.1-71 100 80 1.1-1 100 80 1.1-275 100 80 1.1-335 100 80 1.8-1 100 80 1.1-224 100 80 1.1-115 100 20 1.2-71 90 20 1.1-6 100 20 1.1-30 100 20 1.2-73 90 20 1.42-72 100 20 1.2-336 100 20 1.2-92 100 20 1.2-91 100 20 1.2-81 100 20 1.6-71 100 20 1.6-72 90 20 1.5-71 90 20 1.5-72 80 20 1.5-221 100 20 1.5-91 90 20 1.6-221 100 20 1.4-221 100 20 1.12-91 80 20 1.14-72 100 20 1.54-71 100 20 1.54-241 100 20 1.48-92 100 20 1.1-181 100 20 1.1-151 100 20 1.1-82 80 20 1.1-241 100 20 1.1-334 90 20 1.1-126 100 20 1.1-92 100 20 1.1-276 100 20 1.1-123 100 20 1.1-41 100 20 1.1-121 100 20 1.1-51 100 20 1.1-48 100 20 1.1-340 80 80

- 88 042986

Table A4

Compound, Example No. Abutilon theophrasti (Efficacy in %) Application rate [g/ha] 1.2-72 100 80 1.1-73 100 80 1.48-71 100 80 1.1-26 100 80 1.1-222 100 80 1.1-221 100 80 1.1-341 100 80 1.1-27 100 80 1.48-72 100 80 1.8-271 100 80 1.1-2 100 80 1.1-72 100 80 1.1-271 100 80 1.1-71 100 80 1.1-1 100 80 1.1-275 100 80 1.1-335 100 80 1.8-1 100 80 1.1-224 100 80 1.1-333 100 80

- 89 042986

1.1-340 100 80 1.1-115 100 20 1.2-71 100 20 1.1-180 100 20 1.1-6 100 20 1.1-30 100 20 1.2-73 100 20 1.48-221 100 20 1.48-91 100 20 1.48-81 100 20 1.49-71 100 20 1.49-72 100 20 1.49-221 100 20 1.42-72 100 20 1.2-336 100 20 1.2-92 100 20 1.2-91 100 20 1.2-81 100 20 1.6-71 100 20 1.6-72 100 20 1.5-71 100 20 1.5-72 100 20 1.5-221 100 20 1.5-91 100 20 1.6-221 100 20 1.4-221 100 20 1.12-221 100 20 1.12-71 100 20 1.12-91 100 20 1.12-72 100 20 1.14-221 90 20 1.14-71 100 20 1.14-91 100 20 1.14-72 80 20 1.54-221 100 20 1.54-71 100 20 1.54-241 100 20 1.54-82 100 20 1.48-82 100 20 1.48-73 100 20 1.48-93 100 20 1.48-121 100 20 1.48-92 100 20 1.48-127 100 20 1.1-181 100 20 1.1-151 100 20 1.1-81 100 20 1.1-82 100 20 1.1-132 100 20 1.1-241 100 20 1.1-334 100 20 1.1-331 100 20 1.1-227 100 20 1.1-126 100 20 1.1-91 100 20 1.1-92 100 20 1.1-276 100 20 1.1-123 100 20 1.1-41 100 20 1.1-121 100 20 1.1-51 100 20 1.1-48 100 20

- 90 042986

Table A5

Compound, Example No. Amaranthus retroflexus (Efficiency in %) Application rate [g/ha] 1.2-72 100 80 1.1-73 100 80 1.48-71 100 80 1.1-26 100 80 1.1-222 100 80 1.1-221 100 80 1.1-341 100 80 1.1-27 100 80 1.48-72 100 80 1.8-271 100 80 1.1-2 100 80 1.1-72 100 80 1.1-271 100 80 1.1-71 100 80 1.1-1 100 80 1.1-275 100 80 1.1-335 100 80 1.8-1 100 80 1.1-224 100 80 1.1-333 100 80 1.1-115 100 20 1.2-71 100 20 1.1-180 100 20 1.1-6 100 20 1.1-30 100 20 1.2-73 100 20 1.48-221 90 20 1.48-91 100 20 1.48-81 100 20 1.49-71 100 20 1.49-72 100 20 1.49-221 100 20 1.42-72 100 20 1.2-336 100 20 1.2-92 100 20 1.2-91 100 20 1.2-81 100 20 1.6-71 100 20 1.6-72 100 20 1.5-71 100 20 1.5-72 100 20 1.5-221 100 20 1.5-91 100 20 1.6-221 100 20 1.4-221 100 20 1.12-221 100 20 1.12-71 100 20 1.12-91 100 20 1.12-72 100 20 1.14-221 100 20 1.14-71 100 20 1.14-91 100 20 1.14-72 100 20 1.54-221 100 20 1.54-71 100 20 1.54-241 100 20 1.54-82 100 20

- 91 042986

1.48-82 100 20 1.48-73 100 20 1.48-93 100 20 1.48-121 100 20 1.48-92 100 20 1.48-127 100 20 1.1-181 100 20 1.1-151 100 20 1.1-81 100 20 1.1-82 100 20 1.1-132 100 20 1.1-241 100 20 1.1-334 100 20 1.1-331 100 20 1.1-227 100 20 1.1-126 100 20 1.1-91 100 20 1.1-92 100 20 1.1-276 100 20 1.1-123 100 20 1.1-41 100 20 1.1-121 100 20 1.1-51 100 20 1.1-48 100 20

Table A6

Compound, Example No. Matricaria inodora (Efficacy in %) Application rate [g/ha] 1.2-72 100 80 1.1-73 100 80 1.48-71 100 80 1.1-26 100 80 1.1-222 100 80 1.1-221 100 80 1.1-341 100 80 1.1-27 100 80 1.48-72 100 80 1.8-271 100 80 1.1-2 100 80

- 92 042986

1.1-72 100 80 1.1-271 100 80 1.1-71 100 80 1.1-1 100 80 1.1-275 100 80 1.1-335 100 80 1.8-1 100 80 1.1-224 100 80 1.1-333 100 80 1.1-340 100 80 1.1-115 100 20 1.2-71 100 20 1.1-180 100 20 1.1-6 100 20 1.1-30 100 20 1.2-73 100 20 1.48-221 80 20 1.48-91 100 20 1.48-81 100 20 1.49-71 100 20 1.49-72 90 20 1.49-221 90 20 1.42-72 100 20 1.2-336 100 20 1.2-92 100 20 1.2-91 100 20 1.2-81 100 20 1.6-71 100 20 1.6-72 100 20 1.5-71 100 20 1.5-72 90 20 1.5-221 100 20 1.5-91 90 20 1.6-221 100 20 1.4-221 100 20 1.12-221 100 20 1.12-71 80 20 1.12-91 80 20 1.12-72 100 20 1.14-221 80 20 1.14-72 80 20 1.54-221 100 20 1.48-73 80 20 1.48-121 100 20 1.48-127 90 20 1.1-181 100 20 1.1-151 100 20 1.1-81 90 20 1.1-82 100 20 1.1-132 100 20 1.1-241 100 20 1.1-334 100 20 1.1-331 90 20 1.1-227 100 20 1.1-126 90 20 1.1-91 100 20 1.1-92 80 20 1.1-276 100 20 1.1-123 100 20 1.1-41 90 20 1.1-121 100 20 1.1-51 100 20 1.1-48 100 20

- 93 042986

Table A7

Compound, Example No. Polygonum convolvulus (Efficacy in %) Application rate [g/ha] 1.2-72 100 80 1.1-73 100 80 1.48-71 100 80 1.1-26 100 80 1.1-222 100 80 1.1-221 100 80 1.1-341 100 80 1.1-27 100 80 1.48-72 100 80 1.8-271 100 80 1.1-2 100 80 1.1-72 100 80 1.1-271 100 80 1.1-71 100 80 1.1-1 100 80 1.1-275 100 80 1.1-335 100 80 1.8-1 100 80 1.1-224 100 80 1.1-333 100 80 1.1-340 100 80 1.1-115 100 20 1.2-71 100 20 1.1-180 100 20 1.1-6 100 20 1.1-30 100 20 1.2-73 100 20 1.48-91 100 20 1.48-81 100 20 1.49-71 100 20 1.49-221 100 20 1.42-72 100 20 1.2-336 100 20 1.2-92 100 20 1.2-91 100 20 1.2-81 100 20 1.6-71 100 20 1.6-72 100 20 1.5-71 100 20 1.5-72 90 20 1.5-221 100 20 1.5-91 90 20 1.6-221 100 20 1.4-221 100 20 1.12-221 100 20 1.12-71 80 20 1.12-91 80 20 1.12-72 100 20 1.14-221 80 20 1.14-72 80 20 1.54-221 100 20 1.54-71 100 20 1.54-241 100 20 1.48-82 100 20 1.48-93 80 20 1.48-73 80 20 1.48-92 80 20

- 94 042986

1.48-121 100 20 1.48-127 90 20 1.1-181 100 20 1.1-151 100 20 1.1-81 90 20 1.1-82 100 20 1.1-132 100 20 1.1-241 100 20 1.1-334 90 20 1.1-227 100 20 1.1-91 100 20 1.1-92 100 20 1.1-276 100 20 1.1-123 100 20 1.1-41 100 20 1.1-121 100 20 1.1-51 100 20 1.1-48 100 20

Table A8

Compound, Example No. Stellaria media (Efficiency in %) Application rate [g/ha] 1.2-72 100 80 1.1-73 100 80 1.48-71 100 80 1.1-26 100 80 1.1-222 100 80 1.1-221 100 80 1.1-341 100 80 1.1-27 100 80 1.48-72 100 80 1.8-271 100 80 1.1-2 100 80 1.1-72 100 80 1.1-271 100 80 1.1-71 100 80 1.1-1 100 80 1.1-275 100 80 1.1-335 100 80 1.8-1 100 80

- 95 042986

1.1-224 80 80 1.1-115 100 20 1.2-71 100 20 1.1-180 90 20 1.1-6 90 20 1.1-30 90 20 1.2-73 100 20 1.48-221 100 20 1.48-91 100 20 1.48-81 100 20 1.49-71 100 20 1.49-221 90 20 1.42-72 90 20 1.2-92 100 20 1.2-91 80 20 1.2-81 100 20 1.6-71 100 20 1.6-72 90 20 1.5-71 80 20 1.5-221 90 20 1.6-221 80 20 1.4-221 80 20 1.12-221 80 20 1.12-71 100 20 1.12-91 100 20 1.12-72 100 20 1.54-221 80 20 1.54-71 80 20 1.54-241 80 20 1.48-93 100 20 1.48-73 100 20 1.48-92 100 20 1.48-121 80 20 1.48-127 100 20 1.1-181 100 20 1.1-151 100 20 1.1-82 80 20 1.1-132 80 20 1.1-241 100 20 1.1-334 90 20 1.1-331 80 20 1.1-126 100 20 1.1-276 100 20 1.1-123 100 20 1.1-121 100 20 1.1-51 80 20 1.1-48 100 20

-96042986

Table A9

Compound, Example No. Viola tricolor (Efficiency in %) Application rate [g/ha] 1.2-72 100 80 1.1-73 100 80 1.48-71 100 80 1.1-26 100 80 1.1-222 100 80 1.1-221 100 80 1.1-341 100 80 1.1-27 100 80 1.48-72 100 80 1.8-271 100 80 1.1-2 100 80 1.1-72 100 80 1.1-271 100 80 1.1-71 100 80 1.1-1 100 80 1.1-275 100 80 1.1-335 100 80 1.8-1 100 80 1.1-224 100 80 1.1-333 100 80 1.1-340 100 80 1.1-115 100 20 1.2-71 100 20 1.1-180 100 20 1.1-6 100 20 1.1-30 100 20 1.2-73 100 20 1.48-221 100 20 1.48-91 100 20 1.48-81 100 20 1.49-71 100 20

- 97 042986

1.49-72 100 20 1.42-72 100 20 1.2-336 100 20 1.2-92 100 20 1.2-91 100 20 1.2-81 100 20 1.6-71 100 20 1.6-72 100 20 1.5-71 100 20 1.5-72 100 20 1.5-221 100 20 1.5-91 100 20 1.6-221 100 20 1.4-221 100 20 1.12-221 100 20 1.12-71 100 20 1.12-91 100 20 1.12-72 100 20 1.14-221 100 20 1.14-91 100 20 1.14-72 100 20 1.54-71 100 20 1.54-82 90 20 1.48-73 100 20 1.48-93 100 20 1.48-121 100 20 1.48-92 100 20 1.48-127 100 20 1.1-181 100 20 1.1-151 100 20 1.1-81 100 20 1.1-82 100 20 1.1-132 100 20 1.1-241 100 20 1.1-334 100 20 1.1-331 100 20 1.1-227 80 20 1.1-126 100 20 1.1-91 100 20 1.1-92 100 20 1.1-276 100 20 1.1-123 100 20 1.1-41 100 20 1.1-51 100 20 1.1-48 100 20

-98042986

Table A10

Compound, Example No. Veronica persica (Efficiency in %) Application rate [g/ha] 1.2-72 100 80 1.1-73 100 80 1.48-71 100 80 1.1-26 100 80 1.1-222 100 80 1.1-221 100 80 1.1-341 100 80 1.1-27 100 80 1.48-72 100 80 1.8-271 100 80 1.1-2 100 80 1.1-72 100 80 1.1-271 100 80 1.1-71 100 80 1.1-1 100 80 1.1-275 100 80 1.1-335 100 80 1.8-1 100 80 1.1-224 100 80 1.1-333 80 80 1.1-115 100 20 1.2-71 100 20 1.1-180 100 20 1.1-6 100 20 1.1-30 100 20 1.2-73 100 20 1.48-221 100 20 1.48-91 100 20 1.48-81 100 20 1.49-71 100 20 1.49-72 100 20 1.49-221 100 20 1.42-72 100 20

- 99 042986

1.2-336 100 20 1.2-92 100 20 1.2-91 100 20 1.2-81 100 20 1.6-71 100 20 1.6-72 100 20 1.5-71 100 20 1.5-72 100 20 1.5-221 100 20 1.5-91 100 20 1.6-221 100 20 1.4-221 100 20 1.12-221 100 20 1.12-71 100 20 1.12-91 100 20 1.12-72 100 20 1.14-221 100 20 1.14-71 100 20 1.14-91 100 20 1.14-72 100 20 1.54-221 80 20 1.54-71 100 20 1.54-241 100 20 1.54-82 80 20 1.48-73 100 20 1.48-93 100 20 1.48-121 100 20 1.48-92 100 20 1.48-127 100 20 1.1-181 100 20 1.1-151 100 20 1.1-81 100 20 1.1-82 100 20 1.1-132 100 20 1.1-241 100 20 1.1-334 100 20 1.1-331 100 20 1.1-227 100 20 1.1-126 100 20 1.1-91 100 20 1.1-92 100 20 1.1-276 100 20 1.1-123 100 20 1.1-41 100 20 1.1-121 100 20 1.1-51 100 20 1.1-48 100 20

- 100 042986

Table A11

Compound, Example No. Pharbitis purpurea (Efficacy in %) Application rate [g/ha] 1.2-72 100 80 1.1-73 100 80 1.48-71 100 80 1.1-26 100 80 1.1-222 100 80 1.1-221 100 80 1.1-341 100 80 1.1-27 100 80 1.48-72 100 80 1.8-271 100 80 1.1-2 100 80 1.1-72 100 80 1.1-271 100 80 1.1-71 100 80 1.1-1 100 80 1.1-275 100 80 1.1-335 100 80 1.8-1 100 80 1.1-224 100 80 1.1-333 80 80 1.1-340 100 80 1.1-115 100 20 1.2-71 100 20 1.1-180 100 20 1.1-6 100 20 1.1-30 100 20 1.48-91 100 20 1.48-81 100 20 1.49-71 100 20 1.49-221 100 20

- 101 042986

1.42-72 100 20 1.2-336 100 20 1.2-92 100 20 1.2-91 100 20 1.2-81 100 20 1.6-71 100 20 1.6-72 100 20 1.5-71 100 20 1.5-72 100 20 1.5-221 100 20 1.5-91 100 20 1.6-221 100 20 1.4-221 100 20 1.12-71 100 20 1.12-91 100 20 1.14-221 100 20 1.14-71 100 20 1.14-91 80 20 1.14-72 80 20 1.54-221 100 20 1.54-71 100 20 1.48-73 100 20 1.48-93 100 20 1.48-121 100 20 1.48-127 90 20 1.1-151 100 20 1.1-82 100 20 1.1-132 100 20 1.1-227 100 20 1.1-126 100 20 1.1-91 100 20 1.1-92 100 20 1.1-123 100 20 1.1-41 100 20 1.1-121 100 20 1.1-51 100 20 1.1-48 100 20

Table A12

Compound, Example No. Hordeum murinum (Efficacy in %) Application rate [g/ha] 1.2-72 80 80 1.1-73 80 80 1.48-71 80 80 1.1-26 90 80 1.1-221 80 80 1.1-341 90 80 1.1-27 80 80 1.1-72 80 80 1.1-71 80 80 1.1-115 100 20 1.2-336 80 20 1.6-71 80 20 1.4-221 80 20 1.1-121 80 20 1.1-48 80 20

- 102 042986

Table A13

Compound, Example No. Avena fatua (Efficiency in %) Application rate [g/ha] 1.2-72 80 80 1.1-222 80 80 1.1-221 80 80 1.1-341 90 80 1.8-271 90 80 1.1-72 80 80 1.1-72 80 80 1.1-115 80 20 1.1-121 80 20

Table A14

Compound, Example No. Digitaria sanguinalis (Efficacy in %) Application rate [g/ha] 1.2-72 100 80 1.1-73 100 80 1.48-71 100 80 1.1-26 100 80 1.1-27 100 80 1.48-72 100 80 1.1-2 100 80 1.1-115 100 20 1.2-71 100 20 1.1-6 100 20 1.1-30 100 20 1.48-91 100 20 1.48-81 100 20 1.42-72 100 20 1.2-92 100 20 1.2-81 100 20 1.4-221 100 20 1.6-71 100 20 1.6-72 100 20 1.5-71 100 20 1.5-72 100 20 1.5-221 80 20 1.6-221 100 20 1.54-71 80 20 1.54-241 80 20 1.48-121 80 20 1.1-151 80 20 1.1-82 100 20 1.1-241 100 20 1.1-126 80 20 1.1-123 80 20 1.1-41 100 20 1.1-121 100 20 1.1-51 100 20 1.1-48 100 20

- 103 042986

Table A15

Compound, Example No. Lolium rigidum (Efficacy in %) Application rate [g/ha] 1.2-72 80 80 1.1-73 90 80 1.48-71 80 80 1.1-26 90 80 1.1-222 90 80

1.1-221 90 80 1.1-341 100 80 1.1-27 80 80 1.48-72 80 80 1.1-2 100 80 1.1-72 100 80 1.1-271 100 80 1.1-1 90 80 1.1-275 80 80 1.5-221 80 20 1.6-221 80 20 1.1-181 80 20 1.1-121 80 20

In table. A16-A20 below shows the compatibility values of selected compounds of General formula (I) in accordance with the table. I.1-I.60 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 %).

Table A16

Compound, Example No. Oryza sativa (Efficacy in %) Application rate [g/ha] 1.1-271 10 20 1.1-222 20 80 1.1-221 0 20 1.1-335 10 20 1.1-1 20 5 1.8-1 10 5 1.1-71 20 5 1.1-115 0 5 1.2-71 20 20 1.1-180 0 20 1.1-6 0 5 1.1-30 0 20 1.2-72 20 5 1.2-73 10 20 1.48-72 10 20 1.48-71 20 20

- 104 042986

1.48-221 10 20 1.49-71 10 20 1.49-72 10 20 1.49-221 10 20 1.2-336 0 5 1.12-221 20 20 1.12-71 0 20 1.12-91 0 20 1.12-72 20 20 1.14-221 10 20 1.14-71 0 20 1.14-91 0 20 1.14-72 0 20 1.54-221 20 20 1.54-71 0 5 1.54-241 0 20 1.54-82 0 20 1.48-72 0 5 1.48-73 0 20 1.48-93 0 20 1.48-121 0 20 1.48-92 10 20 1.48-127 0 20 1.1-333 0 80 1.1-181 10 80 1.1-224 10 20 1.1-275 20 20 1.1-340 10 20 1.1-341 10 5 1.1-151 20 20 1.1-81 0 20 1.1-82 10 20 1.1-132 0 20 1.1-241 10 20 1.1-334 10 20 1.1-331 10 20 1.1-227 0 20 1.1-126 0 20 1.1-91 10 20 1.1-92 0 20 1.1-276 10 5 1.1-26 10 5 1.1-27 10 5 1.1-23 10 5 1.1-73 5 20

- 105 042986

Table A17

Compound, Example No. Zea mays (Efficiency in %) Application rate [g/ha] 1.1-271 10 20 1.8-271 20 80 1.1-222 20 20 1.1-221 10 5 1.1-335 10 80 1.1-1 20 20 1.8-1 20 5 1.1-71 20 80 1.1-72 20 20 1.1-115 20 5 1.2-71 0 5 1.48-221 20 80 1.12-221 0 5 1.12-71 0 5 1.12-91 0 5 1.12-72 0 5 1.14-71 0 20 1.14-91 20 20 1.54-221 00 20 1.54-82 20 5 1.48-92 10 5 1.48-127 20 5 1.1-333 0 80 1.1-181 20 80 1.1-224 20 80 1.1-340 0 80 1.1-341 10 20 1.1-151 20 5 1.1-81 10 20 1.1-82 20 20 1.1-132 20 20 1.1-334 20 20 1.1-227 20 20 1.1-126 20 20 1.1-91 20 20 1.1-92 20 20

Table A18

Compound, Example No. Brassica napis (Efficiency in %) Application rate [g/ha] 1.1-271 20 5 1.2-71 20 5 1.12-221 0 5 1.54-241 0 5 1.54-82 0 5 1.48-82 20 5 1.48-121 20 5 1.1-333 0 20 1.1-224 20 20 1.1-340 10 20 1.1-341 0 5 1.1-81 10 5 1.1-82 0 5 1.1-227 0 5 1.1-126 10 5 1.1-91 10 5

- 106 042986

Table A19

Compound, Example No. Glycine max (Efficiency in %) Application rate [g/ha] 1.1-271 20 5 1.8-1 20 5 1.1-71 20 20 1.1-72 10 20 1.54-82 0 5 1.4-221 20 5 1.12-91 0 5 1.12-72 20 5 1.14-71 0 20 1.14-91 20 20

1.14-72 20 20 1.54-82 20 5 1.1-333 20 20 1.1-181 20 20 1.1-340 20 20 1.1-341 10 25 1.1-227 20 5

Table A20

Compound, Example No. Triticum aestivum (Efficacy in %) Application rate [g/ha] 1.1-271 20 20 1.1-222 20 80 1.1-221 20 20 1.1-335 20 80 1.1-1 20 5 1.1-71 20 80 1.1-72 0 20 1.2-71 20 20 1.1-180 20 20 1.1-30 20 20 1.2-72 20 80 1.48-72 20 20 1.48-71 20 20 1.48-91 20 5 1.48-81 20 20 1.49-71 20 20 1.42-72 20 20 1.2-92 20 5 1.2-91 20 5 1.2-81 20 20 1.6-71 20 20 1.6-72 20 5 1.5-71 10 20 1.5-72 20 20 1.5-221 20 20 1.5-91 10 20 1.12-221 20 20 1.12-71 0 5 1.12-91 0 5 1.12-72 0 20 1.14-221 20 20 1.14-71 0 20

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1.14-91 20 20 1.14-72 20 20 1.54-221 0 20 1.54-71 20 5 1.54-241 0 20 1.54-82 0 5 1.48-82 0 5 1.48-73 0 20 1.48-93 0 20 1.48-121 0 20 1.48-92 0 20 1.48-127 10 20 1.1-333 10 20 1.1-181 20 20 1.1-224 20 20 1.1-275 20 20 1.1-340 20 20 1.1-341 10 20 1.1-151 20 5 1.1-81 20 20 1.1-82 0 5 1.1-132 10 5 1.1-241 20 5 1.1-227 10 5 1.1-126 20 20 1.1-91 10 5 1.1-92 10 20 1.1-2 20 5 1.1-26 20 5 1.1-27 10 5 1.1-73 20 80 1.1-123 20 20 1.1-41 20 20 1.1-51 20 20 1.1-48 10 5

The results show that the compounds of general formula (I) according to the present invention, when treated after emergence, show adequate herbicidal efficacy against harmful plants such as, for example, Abutilon theophmsti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Digitaria sanguinalis, 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 0.02 to 0.08 kg of active substance per 1 ha.

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 1 ha.

B. Herbicidal action and compatibility with the crop 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-B16 below shows the effectiveness of the selected compounds of General formula (I) in accordance with the table. I.1-I.60 against various noxious plants and the application rate corresponding to 320 g/ha or less, which were obtained using the above test method.

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Table B1

Compound, Example No. Alopecurus myosuroides (Efficacy in %) Application rate [g/ha] 1.1-271 100 320 1.8-271 90 320 1.1-222 100 320 1.1-221 90 320 1.1-335 90 320 1.1-1 80 320 1.1-27 80 320 1.1-71 100 320 1.1-72 90 320 1.2-72 100 320 1.48-72 90 320 1.48-71 100 320 1.1-333 100 320 1.1-224 100 320 1.1-275 100 320 1.1-340 90 320 1.1-341 90 320 1.1-2 80 320 1.1-181 100 320

Table B2

Compound, Example No. Echinochloa crus-galli (Efficacy %) Application rate [g/ha] 1.1-271 100 320 1.8-271 80 320 1.1-222 100 320 1.1-221 100 320 1.1-335 100 320 1.1-1 100 320 1.8-1 100 320 1.1-71 100 320 1.1-72 100 320 1.2-72 100 320 1.48-72 100 320 1.48-71 100 320 1.1-333 100 320 1.1-224 100 320 1.1-275 100 320 1.1-340 100 320 1.1-341 100 320 1.1-2 100 320 1.1-26 100 320 1.1-27 100 320 1.1-23 100 320 1.1-73 100 320 1.2-71 100 80 1.1-181 100 320

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Table B3

Compound, Example No. Setaria viridis (Efficacy in %) Application rate [g/ha] 1.1-271 100 320 1.1-275 100 320 1.1-27 100 320 1.1-341 100 320 1.1-335 100 320 1.1-1 100 320 1.8-1 100 320 1.1-71 100 320 1.1-72 100 320 1.2-72 100 320 1.1-73 100 320 1.1-26 100 320 1.1-333 90 320 1.1-224 100 320 1.8-271 100 320 1.1-222 100 320 1.1-221 100 320 1.48-72 100 320 1.48-71 100 320 1.1-340 100 320 1.1-2 100 320 1.1-23 100 320 1.2-71 100 80 1.1-181 100 320 1.1-82 100 80

Table B4

Compound, Example No. Abutilon theophrasti (Efficacy in %) Application rate [g/ha] 1.1-271 100 320 1.1-275 100 320 1.1-27 100 320 1.1-341 100 320 1.1-335 100 320 1.1-1 100 320 1.8-1 100 320 1.1-71 100 320 1.1-72 100 320 1.2-72 100 320 1.1-73 100 320 1.1-26 100 320 1.1-333 100 320 1.1-224 100 320 1.8-271 100 320 1.1-222 100 320 1.1-221 100 320 1.48-72 100 320 1.48-71 100 320 1.1-340 100 320 1.1-2 100 320 1.1-23 100 320 1.2-71 100 80 1.1-181 100 320 1.1-81 100 80 1.1-82 100 80 1.1-132 100 80 1.1-227 100 80 1.1-126 100 80 1.1-91 100 80 1.1-92 100 80

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Table B5

Compound, Example No. Amaranthus retroflexus (Efficiency in %) Application rate [g/ha] 1.1-271 100 320 1.1-275 100 320 1.1-27 100 320 1.1-341 100 320 1.1-335 100 320 1.1-1 100 320 1.8-1 100 320 1.1-71 100 320 1.1-72 100 320 1.2-72 100 320 1.1-73 100 320 1.1-26 100 320 1.1-333 100 320 1.1-224 100 320 1.8-271 100 320 1.1-222 100 320 1.1-221 100 320 1.48-72 100 320 1.48-71 100 320 1.1-340 100 320 1.1-2 100 320 1.1-23 100 320 1.2-71 100 80 1.1-181 100 320 1.1-81 100 80 1.1-82 100 80 1.1-132 100 80 1.1-227 100 80 1.1-126 100 80 1.1-91 100 80 1.1-92 100 80

Table B6

Compound, Example No. Matricaria inodora (Efficacy in %) Application rate [g/ha] 1.1-271 100 320 1.1-275 100 320 1.1-27 100 320 1.1-341 100 320 1.1-335 100 320 1.1-1 100 320 1.8-1 100 320 1.1-71 100 320 1.1-72 100 320

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1.2-72 100 320 1.1-73 100 320 1.1-26 100 320 1.1-333 100 320 1.1-224 100 320 1.8-271 100 320 1.1-222 100 320 1.1-221 100 320 1.48-72 100 320 1.48-71 100 320 1.1-340 100 320 1.1-2 100 320 1.1-23 100 320 1.2-71 100 80 1.1-181 100 320 1.1-81 80 80 1.1-82 100 80 1.1-132 100 80 1.1-227 90 80 1.1-126 100 80 1.1-91 100 80 1.1-92 100 80

Table B7

Compound, Example No. Polygonum convolvulus (Efficacy in %) Application rate [g/ha] 1.1-271 320 100 1.1-275 320 100 1.1-27 320 100 1.1-341 320 100 1.1-335 320 100 1.1-1 320 100 1.8-1 320 100 1.1-71 320 100 1.1-72 320 100 1.2-72 320 100 1.1-73 320 100 1.1-26 320 100 1.1-333 320 100 1.1-224 320 90 1.8-271 320 100 1.1-222 320 100 1.1-221 320 100 1.48-72 320 100 1.48-71 320 100 1.1-340 320 100 1.1-2 320 100 1.1-23 320 100 1.2-71 100 80 1.1-81 100 80

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Table B8

Compound, Example No. Stellaria media (Efficiency in %) Application rate [g/ha] 1.1-271 100 320 1.1-275 100 320 1.1-27 100 320 1.1-341 100 320 1.1-335 100 320 1.1-1 100 320 1.8-1 100 320 1.1-71 100 320 1.1-72 100 320 1.2-72 100 320 1.1-73 100 320 1.1-26 100 320 1.1-333 100 320 1.1-224 100 320 1.8-271 90 320 1.1-222 100 320 1.1-221 100 320 1.48-72 100 320 1.48-71 100 320 1.1-340 100 320 1.1-2 100 320 1.2-71 100 80 1.1-181 100 320 1.1-82 100 80

Table B9

Compound, Example No. Viola tricolor (Efficiency in %) Application rate [g/ha] 1.1-271 100 320 1.1-275 100 320 1.1-27 100 320 1.1-341 100 320 1.1-335 100 320 1.1-1 100 320 1.8-1 100 320 1.1-71 100 320 1.1-72 100 320 1.2-72 100 320 1.1-73 100 320 1.1-26 100 320 1.1-333 100 320 1.1-224 100 320 1.8-271 100 320 1.1-222 100 320 1.1-221 100 320 1.48-72 100 320 1.48-71 100 320 1.1-340 100 320 1.1-2 100 320 1.1-23 100 320 1.2-71 100 80 1.1-181 100 320 1.1-81 100 80 1.1-82 100 80 1.1-132 90 80 1.1-227 80 80 1.1-91 100 80

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Table B10

Compound, Example No. Veronica persica (Efficiency in %) Application rate [g/ha] 1.1-271 100 320 1.1-275 100 320 1.1-27 100 320 1.1-341 100 320 1.1-335 100 320 1.1-1 100 320 1.8-1 100 320 1.1-71 100 320 1.1-72 100 320 1.2-72 100 320 1.1-73 100 320 1.1-26 100 320 1.1-333 100 320 1.1-224 100 320 1.8-271 100 320 1.48-72 100 320 1.48-71 100 320 1.1-340 100 320 1.1-2 100 320 1.2-71 100 80 1.1-181 100 320 1.1-81 80 80 1.1-82 100 80 1.1-91 100 80

Table B11

Compound, Example No. Pharbitis purpurea (Efficacy in %) Application rate [g/ha] 1.1-271 100 320 1.1-275 100 320 1.1-27 100 320 1.1-341 100 320 1.1-335 100 320 1.1-1 100 320 1.8-1 100 320 1.1-71 100 320 1.1-72 100 320 1.2-72 100 320 1.1-73 100 320 1.1-26 100 320 1.1-333 100 320 1.1-224 100 320 1.8-271 100 320 1.1-222 100 320 1.1-221 100 320 1.48-72 100 320 1.48-71 100 320 1.1-340 100 320 1.1-2 100 320 1.1-23 100 320 1.2-71 100 80 1.1-181 100 320 1.1-82 100 80

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Table B12

Compound, Example No. Hordeum murinum (Efficacy in %) Application rate [g/ha] 1.1-271 100 320 1.1-275 90 320 1.1-27 80 320 1.1-341 80 320 1.1-335 90 320 1.1-1 90 320 1.8-1 90 320 1.1-71 90 320 1.1-72 90 320 1.2-72 90 320 1.1-73 90 320 1.1-26 100 320 1.1-333 100 320 1.1-224 100 320 1.1-222 90 320 1.1-221 100 320 1.1-181 90 320

Table B13

Compound, Example No. Avena fatua (Efficiency in %) Application rate [g/ha] 1.1-271 100 320 1.8-271 90 320 1.1-222 100 320 1.1-221 100 320 1.1-335 100 320 1.1-1 90 320 1.8-1 80 320 1.1-71 90 320 1.1-72 100 320 1.2-72 80 320 1.48-72 80 320 1.48-71 80 320 1.1-333 100 320 1.1-224 100 320 1.1-275 100 320 1.1-340 80 320 1.1-341 90 320 1.1-2 90 320 1.1-26 80 320 1.1-73 90 320 1.1-181 100 320

Table B14

Compound, Example No. Digitaria sanguinalis (Efficacy in %) Application rate [g/ha] 1.1-26 100 80 1.1-27 100 80 1.2-72 100 80 1.48-72 100 80 1.48-71 100 80 1.1-73 100 80 1.1-2 100 80 1.2-71 100 80 1.1-82 80 80

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Table B15

Compound, Example No. Lolium rigidum (Efficacy in %) Application rate [g/ha] 1.1-271 100 320 1.1-275 90 320 1.1-27 90 320 1.1-341 100 320 1.1-335 100 320 1.1-1 80 320 1.8-1 90 320 1.1-71 90 320 1.1-72 100 320 1.2-72 90 320 1.1-73 100 320 1.1-26 90 320 1.1-333 100 320 1.1-224 100 320 1.1-222 100 320 1.1-221 100 320 1.48-72 80 320 1.48-71 90 320 1.1-340 100 320 1.1-2 90 320 1.1-181 100 80

Table B16

Compound, Example No. Cyperus esculentus (Efficacy in %) Application rate [g/ha] 1.1-271 80 320 1.1-224 90 320 1.1-222 100 320 1.1-221 100 320 1.1-275 80 320 1.1-1 100 320 1.8-1 90 320 1.1-71 80 320 1.1-72 80 320 1.1-333 80 320

In table. B17-B19 below shows the compatibility values of selected compounds of General formula (I) in accordance with the table. I.1-I.60 with crops at an application rate corresponding to 320 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 %).

Table B17

Compound, Example No. Oryza sativa (Efficacy %) Application rate [g/ha] 1.1-271 20 20 1.8-271 0 80 1.2-71 0 20 1.1-181 0 20 1.1-224 0 20 1.1-126 20 80 1.1-92 10 80

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Table B18

Compound, Example No. Zea mays (Efficiency in %) Application rate [g/ha] 1.1-271 0 20 1.8-271 20 80 1.1-222 20 20 1.1-221 0 20 1.1-335 20 20 1.1-1 20 20 1.1-71 0 80 1.1-72 20 80 1.2-71 10 80 1.2-72 10 80 1.48-72 0 320 1.48-71 20 320 1.1-333 20 80 1.1-181 0 20 1.1-224 0 20 1.1-340 0 80 1.1-341 0 80 1.1-81 0 80 1.1-82 0 80 1.1-227 0 80 1.1-132 0 80 1.1-126 0 80 1.1-91 0 80 1.1-92 0 80 1.1-2 0 20 1.1-26 10 80 1.1-27 0 80 1.1-23 10 80 1.1-73 0 80

Table B19

Compound, Example No. Glycine max (Efficiency in %) Application rate [g/ha] 1.1-271 10 20 1.1-222 10 20 1.1-71 0 80 1.1-72 20 80 1.2-71 0 80 1.2-72 20 20 1.48-72 10 320 1.48-71 0 20 1.1-333 0 80 1.1-181 20 80 1.1-224 0 20 1.1-340 20 80 1.1-81 0 80 1.1-132 20 80 1.1-126 10 80 1.1-91 20 80 1.1-26 0 20 1.1-27 20 80 1.1-23 0 80 1.1-73 0 80

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, Avenafatua, Cyperus esculentus, Digitaria sanguinalis, Echinocloa crus-galli, Hordeum murinum, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridis, Steliaria media, Veronica persica and Viola tricolor, at an application rate of 0.32 kg of active substance per 1 ha.

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The test crop plants Glycine max, Oryza sativa and Zea mays are affected only slightly, if at all, after the application of the compounds of general formula (I) in accordance with the present invention at an application rate of 0.02 to 0.32 kg ai/ha .

Claims (8)

1. Substituted thiophenyluracil of general formula (I) or its salt in which R ¹ represents (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 are independently hydrogen, halogen, (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)alkoxy(C1-C8)alkyl, (C1-C8)alkoxy(C1-C8)haloalkyl, (C1C8)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(C1C8)alkyl, (C1-C8)alkylthio(C1 -C8) alkyl, (C 1 -C8) haloalkylthio (C 1 -C8) alkyl, (C 1 -C8) alkylcarbonyl (C 1 C8) alkyl, C (O) OR ¹⁹ , C (O) NR ¹⁷ R ¹⁸ , C(O)R ¹⁹ , R ¹⁹ O(O)C-(C1-C ₈ )alkyl, R ¹⁷ R ¹⁸ N(O)C-(C1-C8)alkyl, R ¹⁷ R ¹⁸ 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 to 10-membered monocyclic or bicyclic ring, or R ⁵ and R ⁶ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I') below R ⁷ and R ⁸ 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, (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 , heterocyclyl, heterocyclyl (C1-C8) alkyl, (C1-C8) alkylthio (C1-C8) alkyl, (C1-C8) haloalkylthio (C1-C8) alkyl, C (O) OR ¹⁹ , C (O) NR ¹⁷ R ¹⁸ , C(O)R ¹⁹ , R ¹⁹ O(O)C-(C1-C ₈ )αalkyl, R ¹⁷ R ¹⁸ N(O)C-(C1-C8)alkyl, R ¹⁷ R ¹⁸ N-( C1-C ₈ )alkyl, 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 ⁷ and R ⁸ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I) below m is 0; n is 0, 1, 2, 3, 4, 5, 6; p is 1, 2, 3; X is O (oxygen), N (nitrogen), or NR ¹⁵ or NOR ¹⁶ moieties, wherein R ¹⁵ and R ¹⁶ in NR ¹⁵ and NOR ¹⁶ moieties are independently defined as defined below; Y represents O (oxygen) or S (sulfur), SO, SO ₂ ; R ¹⁰ and R ¹¹ are independently hydrogen, fluorine, cyano, (C1-C8) alkyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl (C1-C8) alkyl, (C2-C8) alkenyl, (C2 -C8)alkynyl, (C1-C10)haloalkyl, aryl, aryl(C1C8)alkyl, heteroaryl, heteroaryl(C1-C8)alkyl, (C4-C10)cycloalkenyl(C1-C8)alkyl, heterocyclyl, heterocyclyl(C1-C8 )alkyl, R ¹⁹ O-(C1-C ₈ )alkyl, R ²⁰ S-(C1-C8 )alkyl, R ²⁰ SO2-(C ₁ -C ₈ )alkyl, or R ¹⁰ and R ¹¹ together with the carbon atom to which they are attached, form a fully saturated or partially saturated 3-10-membered monocyclic or bicyclic ring; - 118 042986 R ¹² and R ¹³ independently represent hydrogen, fluorine, (C1-C8) alkyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl (C1-C8) alkyl, (C2-C8) alkenyl, (C2-C8 ) alkynyl, (C1-C1o) haloalkyl, (C2-C8) haloalkenyl, (C2-C8) haloalkynyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4-C10) halocycloalkenyl, (C1C8) 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 ¹⁹ O-(C1C8) alkyl, R ²⁰ S-(C1-C8) alkyl, R ²⁰ SO2-(C ₁ -C ₈ ) alkyl, R ¹⁷ R ¹⁸ N -(C ₁ -C ₈ )alkyl, or R ¹² and R ¹³ 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 R ¹⁴ is (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(C1C8)alkyl, aryl, aryl(C1-C8)alkyl, heteroaryl, heteroaryl(C1-C8)alkyl, heterocyclyl, heterocyclyl( C1C8) alkyl, (C1-C8) alkylthio (C1-C8) alkyl, (C1-C8) haloalkylthio (C1-C8) alkyl, R ¹⁷ R ¹⁸ N-(C1-C ₈ ) alkyl, cyano (C1-C8) alkyl, or R ¹⁰ and R ¹⁴ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or R ¹² and R ¹⁴ 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 ¹⁵ 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, (C1C ₈ ) alkoxycarbonyl, (C ₁ -C ₈ ) alkoxy, (C ₂ -C ₈ ) alkenyloxy, aryl (C 1 -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, halogen (C ₂ -C ₈ ) alkenyl, (C ₁ -C ₈ ) alkoxy (C ₁ -C ₈ ) alkyl, amino, (C 1-C ₈ ) alkylamino, bis-[(C 1-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 -C ₈ ) alkylsulfonyl, (C ₂ -C ₈ ) alkenyloxycarbonyl, (C ₂ -C ₈ ) alkynyloxycarbonyl, (C ₁ -C ₈ )alkylaminocarbonyl, (C ₃ C ₈ )cycloalkylaminocarbonyl, bis-[(C ₁ -C ₈ )alkyl]aminocarbonyl; R ¹⁶ 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 ¹⁹ O(O)C-(C1-C ₈ )alkyl, R ¹⁷ R ¹⁸ N(O)C(C ₁ -C ₈ )alkyl; R ¹⁷ and R ¹⁸ 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, (C2C8) haloalkynyl, (C3-C10) cycloalkyl, (C3-C10) halocycloalkyl, (C4-C10) cycloalkenyl, (C4C10) halocycloalkenyl, (C1-C8) alkoxy (C1-C8) alkyl, ( C1-C8) haloalkoxy(C1-C8) alkyl, (C1-C8) alkylthio(C1C8) alkyl, (C1-C8) haloalkylthio(C1-C8) alkyl, (C1-C8) alkoxy(C1-C8) haloalkyl, aryl , aryl (C1-C8) alkyl, heteroaryl, heteroaryl (C1-C8) alkyl, (C3-C8) cycloalkyl (C1-C8) alkyl, (C4-C10) cycloalkenyl (C1-C8) alkyl, COR ¹⁹ , SO2R ²⁰ , (C1-C ₈ )alkyl-HNO ₂ S-, (C ₃ -C ₈ )cycloalkyl-HNO ₂ S-, heterocyclyl, (C ₁ -C ₈ )alkoxycarbonyl-(C ₁ -C ₈ )alkyl, (C1 -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 ¹⁹ 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 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 ( C1-C ₈ )alkyl, (C ₃ 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 ²⁰ is hydrogen, (C1-C8) alkyl, (C2-C8) alkenyl, (C2-C8) alkynyl, (C1-C8) 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 -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, heterocyclyl (C1-C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl (C ₁ -C ₈ ) alkyl, (C ₄ -C ₁₀ ) cycloalkenyl (C 1 -C ₈ ) alkyl, NR ¹⁷ R ¹⁸ ; R ²¹ is fluoro and R ²² and R ²³ independently represent hydrogen, halogen, (C 1 -C ₈ )alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₂ C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, (C 1 -C ₈ ) haloalkyl, aryl, or R ²² and R ²³ together with the carbon atom to which they are bonded form a 3-10 membered monocyclic or bicyclic ring which is saturated, where aryl is a mono-, bi- or polycyclic aromatic system containing 6-14 carbon atoms in 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, - 119 042986 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 (C _g C ₇ )alkyl; R ² is hydrogen, (C ₁ -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-C7) haloalkyl, (C2-C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C7) halocycloalkyl, (C4-C7) cycloalkenyl, (C4-C7) halocycloalkenyl, (C 1 -C7) alkoxy . (C1-C7)alkyl, aryl, aryl(C1-C7)alkyl, heteroaryl, heteroaryl(C1-C7)alkyl, (C4-C7)cycloalkenyl(C1-C7)alkyl, heterocyclyl, heterocyclyl(C1-C7)alkyl, (C1C7) alkylthio (C 1 -C7) alkyl, (C 1 -C7) haloalkylthio (C 1 -C7) alkyl, (C 1 -C7) alkylcarbonyl (C 1 -C7) alkyl, C (O) OR ¹⁹ , C (O)NR ¹⁷ R ¹⁸ , C(O)R ¹⁹ , R ¹⁹ O(O)C-(CrC7)alkyl, R ¹⁷ R ¹⁸ N(O)C-(C1-C7)alkyl, R ¹⁷ R ¹⁸ N -(C _r 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 to 10-membered monocyclic or bicyclic ring, or R ⁵ and R ⁶ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I') below R ⁷ and R ⁸ independently represent hydrogen, halogen, (C ₁ -C ₇ )alkyl, (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 ) haloalkyl, (C ₂ -C ₇ ) haloalkenyl, (C ₂ -C ₇ ) haloalkynyl, (C ₃ -C ₇ ) halocycloalkyl, (C ₁ -C ₇ )alkoxy(C ₁ -C ₇ )alkyl, (C ₁ -C ₇ )alkoxy(C ₁ C ₇ )haloalkyl, (C ₁ -C ₇ )haloalkoxy(C ₁ -C ₇ )haloalkyl, (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, heterocyclyl (C ₁ -C ₇ )alkyl, (C ₁ C ₇ )alkylthio (C ₁ -C ₇ )alkyl, (C ₁ -C ₇ ) haloalkylthio (C ₁ -C ₇ )alkyl, C(O)OR ¹⁹ , C(O)NR ¹⁷ R ¹⁸ , C(O)R ¹⁹ , R ¹⁹ O(O)C-(C1-C7)alkyl, R ¹⁷ R ¹⁸ N(O)C-(C1-C7)alkyl, R ¹⁷ R ¹⁸ N-(C1- C7)alkyl, 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 ⁷ and R ⁸ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (D) below m is 0; n is 0, 1, 2, 3, 4, 5, 6; p is 1, 2, 3; X is O (oxygen), N (nitrogen), or NR ¹⁵ or NOR ¹⁶ moieties, wherein R ¹⁵ and R ¹⁶ in NR ¹⁵ and NOR ¹⁶ moieties are independently defined as defined below; Y represents O (oxygen) or S (sulfur), SO, SO ₂ ; R ¹⁰ and R ¹¹ are independently hydrogen, fluorine, cyano, (C1-C7) alkyl, (C3-C7) cycloalkyl, (C3-C7) cycloalkyl (C1-C7) alkyl, (C2-C7) alkenyl, (C2 -C7)alkynyl, (C1-C7)haloalkyl, aryl, aryl(C1C7)alkyl, heteroaryl, heteroaryl(C1-C7)alkyl, (C4-C7)cycloalkenyl(C1-C7)alkyl, heterocyclyl, heterocyclyl(C1-C7) )alkyl, R ¹⁹ O-(C1-C ₇ )alkyl, R ²⁰ S-(C1-C7)alkyl, R ²⁰ SO2-(C ₁ -C ₇ )alkyl, or R ¹⁰ and R ¹¹ 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 ¹² and R ¹³ are independently hydrogen, fluoro, (C1-C7)alkyl, (C3-C7)cycloalkyl, (C3C7)cycloalkyl(C1-C7)alkyl, (C2-C7)alkenyl, (C2-C7)alkynyl , (C1-C7) haloalkyl, (C2-C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C7) halocycloalkyl, (C4-C7) cycloalkenyl, (C4-C7) halocycloalkenyl, (C 1 -C7) alkoxy (C 1 -C7) haloalkyl, (C 1 -C7) haloalkoxy (C 1 -C7) haloalkyl, aryl, aryl (C 1 -C7) alkyl, heteroaryl, heteroaryl (C 1 -C 7) alkyl, (C 4 -C 10) cycloalkenyl (C1-C7)alkyl, heterocyclyl, heterocyclyl(C1C7)alkyl, R ¹⁹ O-(C1-C ₇ )alkyl, R ²⁰ S-(C1-C7) alkyl, R ²⁰ SO2-(C ₁ -C ₇ )alkyl , R ¹⁷ R ¹⁸ N-(C ₁ -C ₇ )alkyl, or R ¹² and R ¹³ 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 - 120 042986 R ¹⁴ is (C1-C7) alkyl, (C1-C7) haloalkyl, (C3-C7) cycloalkyl, (C3-C7) cycloalkyl (C1-C7) alkyl, (C2-C7) alkenyl, (C2-C7) alkynyl, (C1-C7)alkoxy(C1-C7)alkyl, (C1-C7)haloalkoxy(C1C7)alkyl, aryl, aryl(C1-C7)alkyl, heteroaryl, heteroaryl(C1-C7)alkyl, heterocyclyl, heterocyclyl( C1C7) alkyl, (C1-C7) alkylthio (C1-C7) alkyl, (C1-C7) haloalkylthio (C1-C7) alkyl, R ¹⁷ R ¹⁸ N-(C1-C ₇ ) alkyl, cyano (C ₁ -C ₇ ) alkyl, or R ¹⁰ and R ¹⁴ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or R ¹² and R ¹⁴ 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 ¹⁵ is hydrogen, (C 1 -C ₇ )alkyl, (C ₃ -C ₇ ) cycloalkyl, cyano(C 1 -C ₇ ) alkyl, (C ₃ C ₇ ) cycloalkyl (C ₁ -C ₇ ) alkyl, (C 1 -C ₇ )alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C ₃ C7) cycloalkylsulfonyl, heterocyclylsulfonyl, aryl (C1-C7) alkylsulfonyl, (C1-C7) alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C3-C7) cycloalkylcarbonyl, heterocyclylcarbonyl, (C1C 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, (C ₁ C ₇ )alkoxy(C ₁ -C ₇ )alkoxy(C ₁ -C ₇ )alkyl, heteroaryl( C ₁ -C ₇ ) alkylsulfonyl, heterocyclyl (C ₁ -C ₇ ) alkylsulfonyl, (C ₂ -C ₇ ) alkenyloxycarbonyl, (C ₂ -C ₇ ) alkynyloxycarbonyl, (C ₁ -C ₇ ) alkylaminocarbonyl, (C ₃ C ₇ )cycloalkylaminocarbonyl, bis-[(C ₁ -C ₇ )alkyl]aminocarbonyl; R ¹⁶ 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 ¹⁹ O(O)C-(C1-C ₇ )alkyl, R ¹⁷ R ¹⁸ N(O)C(C ₁ -C ₇ )alkyl; R ¹⁷ and R ¹⁸ are the same or different and are independently hydrogen, (C1C7) alkyl, (C2-C7) alkenyl, (C2-C7) alkynyl, (C1-C7) cyanoalkyl, (C1-C7) haloalkyl, (C2 -C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C7) cycloalkyl, (C3-C7) halocycloalkyl, (C4-C10) cycloalkenyl, (C4-C7) 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, (C4C7)cycloalkenyl(C1-C7)alkyl, COR ¹⁹ , SO2R ²⁰ , (С1-С ₇ )alkyl-HNO ₂ S-, (С ₃ -С ₇ ) cycloalkyl-HNO ₂ S-, heterocyclyl, (С1-С ₇ ) alkoxycarbonyl-(С 1 -С ₇ ) alkyl, (C 1 -C ₇ ) alkoxycarbonyl, aryl (C 1 -C ₇ ) 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(C1-C ₇ )alkyl; R ¹⁹ 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 ₇ ) cycloalkyl, (C ₃ -C ₇ ) halocycloalkyl, (C ₄ -C ₇ ) cycloalkenyl, (C ₄ -C ₇ ) 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 , (C3C7) cycloalkyl (C1-C7) alkyl, (C4-C7) cycloalkenyl (C1-C7) alkyl, (C1-C7) alkoxycarbonyl-(C1-C7) 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 ²⁰ is hydrogen, (C ₁ -C ₇ )alkyl, (C ₂ -C ₇ )alkenyl, (C ₂ -C ₇ )alkynyl, (C ₁ -C ₇ )cyanoalkyl, (C ₁ -C ₇ ) haloalkyl , (C ₂ -C ₇ ) haloalkenyl, (C ₂ -C ₇ ) haloalkynyl, (C ₃ -C ₇ ) cycloalkyl, (C ₃ C ₇ ) halocycloalkyl, (C ₄ -C ₇ ) cycloalkenyl, (C ₄ -C ₇ ) 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 - C7)alkyl, heterocyclyl(C1-C7)alkyl, (C3-C7)cycloalkyl(C1-C7)alkyl, (C4-C7)cycloalkenyl(C1-C7)alkyl, NR ¹⁷ R ¹⁸ ; And R ²¹ is fluoro and R ²² and R ²³ are independently hydrogen, halogen, (C1-C7) alkyl, (C3-C7) cycloalkyl, (C2-C7) alkenyl, (C2-C7) alkynyl, (C1-C7) haloalkyl, aryl, or R ²² and R ²³ together with the carbon atom to which they are attached form a 3-10 membered monocyclic or bicyclic ring which is saturated. 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-C6) haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) halocycloalkyl, (C1-C6) alkoxy, (C1-C6) alkoxy (C1-C6) alkyl, ( Cp C6)alkoxy(C1-C6)haloalkyl, (C1-C6)haloalkoxy(C1-C6)haloalkyl, (CpC6)haloalkoxy(CpC6)alkyl, aryl, aryl(C1-C6)alkyl, heteroaryl, heteroaryl(C1- C6)alkyl, heterocyclyl, heterocyclyl(C1C6)alkyl, (C1-C6)alkylthio(C1-C6)alkyl, (C1-C6)haloalkylthio(C1-C6')alkyl, (C1-C6)alkylcarbonyl(C1C6)alkyl, C(O)OR ¹⁹ , C(O)NR ¹⁷ R ¹⁸ , C(O)R ¹⁹ , R ¹⁹ O(O)C-(C1-C6)alkyl, R ¹⁷ R ¹⁸ N(O)C-(C1 -C6)alkyl, R ¹⁷ R ¹⁸ N(C1-C ₆ )alkyl, or - 121 042986 R ⁵ and R ⁶ 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 ⁵ and R ⁶ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I') below R ⁷ and R ⁸ are independently hydrogen, halogen, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6 ) alkynyl, (C1-C6) haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) halocycloalkyl, (C1-C6) alkoxy (C1-C6) alkyl, (C1-C6) alkoxy (C 1 -C6) haloalkyl, (C 1 -C6) haloalkoxy (C1-C6) haloalkyl, (C 1 -C6) haloalkoxy (C 1 -C6) alkyl, aryl, aryl (C 1 -C 6) alkyl, heteroaryl, heteroaryl (C1-C6)alkyl, heterocyclyl, heterocyclyl(C1-C6)alkyl, (C1-C6)alkylthio(C1-C6)alkyl, (C1-C6)haloalkylthio(C1-C6)alkyl, C(O)OR ¹⁹ , C(O)NR ¹⁷ R ¹⁸ , C(O)R ¹⁹ , R ¹⁹ O(O)C-(C1-C ₆ )alkyl, R ¹⁷ R ¹⁸ N(O)C-(C1-C6)alkyl, R ¹⁷ R ¹⁸ N-(C1-C ₆ )alkyl, or R ⁷ and R ⁸ together with the carbon atom to which they are bonded form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring, or R ⁷ and R ⁸ together with the carbon atom to which they are bonded form a double bond , optionally substituted with R ²² and R ²³ according to formula (I'') below m is 0; n is 0, 1, 2, 3, 4, 5, 6; p is 1, 2, 3; X is O (oxygen), N (nitrogen), or NR ¹⁵ or NOR ¹⁶ moieties, wherein R ¹⁵ and R ¹⁶ in NR ¹⁵ and NOR ¹⁶ moieties are independently defined as defined below; Y represents O (oxygen) or S (sulfur), SO, SO ₂ ; R ¹⁰ and R ¹¹ are independently hydrogen, fluorine, cyano, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (C1-C6) alkyl, (C2-C6) alkenyl, (C2 -C6)alkynyl, (C1-C6)haloalkyl, aryl, aryl(C1C6)alkyl, heteroaryl, heteroaryl(C1-C6)alkyl, (C4-C6)cycloalkenyl(C1-C6)alkyl, heterocyclyl, heterocyclyl(C1-C6 )alkyl, R ¹⁹ O-(C1-C ₆ )alkyl, R ²⁰ S-(C1-C6)alkyl, R ²⁰ SO2-(C ₁ -C ₆ )alkyl, or R ¹⁰ and R ¹¹ 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 ¹² and R ¹³ independently represent hydrogen, fluorine, (C1-C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, (C ₃ C ₆ )cycloalkyl(C1-C ₆ )alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C 1 -C ₆ ) haloalkyl, (C ₂ -C ₆ ) haloalkenyl, (C ₂ -C ₆ ) haloalkynyl, (C ₃ -C ₆ ) halocycloalkyl, (C ₄ -C ₆ ) cycloalkenyl, (C ₄ -C ₆ ) halocycloalkenyl, (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) haloalkyl, (C ₁ -C ₆ ) haloalkoxy (C ₁ -C ₆ ) haloalkyl, aryl , aryl(C1-C ₆ )alkyl, heteroaryl, heteroaryl(C1-C ₆ )alkyl, (C ₄ -C ₁₀ )cycloalkenyl(C1-C ₆ )alkyl, heterocyclyl, heterocyclyl(C1C ₄ )alkyl, R ¹⁹ O- (C1-C6)alkyl, R ²⁰ S-(C1-C6)alkyl, R ²⁰ SO2-(C1-C6)αlkyl, R ¹⁷ R ¹⁸ N-(C1-C6)alkyl, or R ¹² and R ¹³ 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 (C1-C6) alkyl, (C1-C6) haloalkyl, (C3-C6) cycloalkyl, (C3-C6) 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(C 1 -C6) alkyl, (C1 -C6) alkylthio (C 1 -C6) alkyl, (C 1 -C6) haloalkylthio (C 1 -C6) alkyl, R ¹⁷ R ¹⁸ N- (C 1 -C ₆ ) alkyl, cyano ( C1-C ₆ )alkyl, or R ¹⁰ and R ¹⁴ together with the carbon atoms to which they are attached form a fully saturated or partially saturated 3 to 10 membered monocyclic or bicyclic ring, or R ¹² and R ¹⁴ 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 ¹⁵ 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 C ₆ )cycloalkylsulfonyl, heterocyclylsulfonyl, aryl(C1-C ₆ )alkylsulfonyl, (C ₁ -C ₆ )alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C ₃ -C ₆ )cycloalkylcarbonyl, heterocyclylcarbonyl, (C1-C ₆ ) alkoxycarbonyl, (C ₁ -C ₆ ) alkoxy, (C ₂ -C ₆ ) alkenyloxy, aryl (C 1-C ₆ ) alkoxycarbonyl, (C ₁ -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 (C ₁ -C ₆ )alkyl, amino, (C1-C ₆ )alkylamino, bis-[(C1-C ₆ )alkyl]amino, (C1C ₆ )alkoxy(C1-C ₆ )alkoxy(C1-C ₆ ) alkyl, heteroaryl (C1-C ₆ )alkylsulfonyl, heterocyclyl (C1-C ₆ )alkyl- 122 042986 sulfonyl, (C ₂ -C ₆ ) alkenyloxycarbonyl, (C ₂ -C ₆ ) alkynyloxycarbonyl, (C 1-C6) alkylaminocarbonyl, ( C ₃ C ₆ cycloalkylaminocarbonyl, bis-[(C1-C ₆ )alkyl]aminocarbonyl; R ¹⁶ 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 ¹⁹ O(O)C-(C1-C ₆ )alkyl, R ¹⁷ R ¹⁸ N(O)C(C ₁ -C ₆ )alkyl; R ¹⁷ and R ¹⁸ are the same or different and are independently hydrogen, (C1C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) cyanoalkyl, (C1-C6) haloalkyl, (C2C6 ) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) cycloalkyl, (C3-C6) halocycloalkyl, (C4C10) cycloalkenyl, (C4-C6) halocycloalkenyl, (C1-C6) alkoxy (C1-C6) alkyl, ( C1-C6) haloalkoxy(C1C6)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-C6) cycloalkenyl (C1-C6) alkyl, COR ¹⁹ , SO2R ²⁰ , (C1- C ₆ )alkyl-HNO ₂ S-, (C ₃ -C ₆ ) cycloalkylHNO2S-, heterocyclyl, (C1-C6) alkoxycarbonyl-(C1-C6) alkyl, (C1-C6) alkoxycarbonyl, aryl (C1C6) alkoxycarbonyl-( C1-C6)alkyl, aryl(C1-C6)alkoxycarbonyl, heteroaryl(C1- _C6 )alkoxycarbonyl, (C2C6)alkenyloxycarbonyl, ( _C2 - _C6 )alkynyloxycarbonyl, heterocyclyl( _C1 - _C6 )alkyl; R ¹⁹ 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 ₆ ) cycloalkyl, (C ₃ C ₆ ) halocycloalkyl, (C ₄ -C ₆ ) cycloalkenyl, (C ₄ -C ₆ ) 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, (C ₃ C ₆ )cycloalkyl (C1-C ₆ )alkyl, (C ₄ -C ₆ )cycloalkenyl (C1-C ₆ )alkyl, (C1-C ₆ )alkoxycarbonyl-(C1-C ₆ )alkyl, (C ₂ -C ₆ )alkenyloxycarbonyl-(C1-C ₆ )alkyl, aryl(C1-C ₆ )alkoxycarbonyl-(C1-C ₆ )alkyl, hydroxycarbonyl(C1-C ₆ )alkyl, heterocyclyl, heterocyclyl( C1- _C6 )alkyl; R ²⁰ is hydrogen, (C1-C ₆ )alkyl, (C ₂ -C ₆ )alkenyl, (C ₂ -C ₆ )alkynyl, (C1-C ₆ )cyanoalkyl, (C1-C ₆ ) haloalkyl, (C ₂ -C ₆ ) haloalkenyl, (C ₂ -C ₆ ) haloalkynyl, (C ₃ -C ₆ ) cycloalkyl, (C ₃ C ₆ ) halocycloalkyl, (C ₄ -C ₆ ) cycloalkenyl, (C ₄ -C ₆ ) halocycloalkenyl , (C 1 -C ₆ )alkoxy(C 1 -C ₆ )alkyl, (C1-C ₆ )alkoxy(C1-C ₆ )haloalkyl, aryl, aryl(C1-C ₆ )alkyl, heteroaryl, heteroaryl(C1- C ₆ ) alkyl, heterocyclyl (C 1 -C ₆ ) alkyl, (C ₃ -C ₆ ) cycloalkyl (C 1 -C ₆ ) alkyl, (C ₄ -C ₆ ) cycloalkenyl (C 1 -C ₆ ) alkyl, NR ¹⁷ R ¹⁸ ; R ²¹ is fluoro and R ²² and R ²³ independently represent hydrogen, halogen, (C1-C ₆ )alkyl, (C ₃ -C ₆ )cycloalkyl, (C ₂ C ₆ )alkenyl, (C ₂ -C ₆ )alkynyl, (C1-C ₆ ) haloalkyl, aryl, or R ²² and R ²³ together with the carbon atom to which they are attached form a 3-10 membered monocyclic or bicyclic ring which is saturated. 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 represents 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, 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-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, 3,5-bis(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, 3bromopyrazin-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 - 124 042986 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, 3,5-difluoropyridin-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, or R ⁵ and R ⁶ 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 ⁵ and R ⁶ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I') below R ⁷ and R ⁸ independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1- methylbutyl, 2methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2dimethylbutyl, 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-2methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobut-1-yl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 3,3-difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, 2-fluorocycloprop-1-yl, 4fluorocyclohexyl, 4,4-difluorocyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1- methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl- 2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2- dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3methyl-2-pentenyl, 4-methyl-2- pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3- methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl- 2-butenyl, 1,2dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1 - 125 042986 butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1butenyl, 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, 1-ethyl-2 -methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl , 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl , 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl -4-pentynyl, 3-methyl-1-pentynyl, 3-methyl4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl -3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3butynyl, 2 -ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlordifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2 -fluoroethyl, fluoromethyl, difluoromethyl, 2,2difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl 3 -fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3 ,4,5-trifluorophenyl, 2chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl , 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-bromo4 -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-4bromophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-fluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4 -chlorophenyl, 2fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-methylphenyl, 3methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2 ,5-dimethylphenyl, 2,6-dimethylphenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,5-trimethylphenyl, 3,4,5-trimethylphenyl, 2,4,6 -trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,6dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2 ,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4-difluoromethoxyphenyl, 2-trifluoromethylphenyl , 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 3,5-bis-(trifluoromethyl)phenyl, 3trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl- 5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2trifluoromethylthiophenyl, 3-trifluoromethylthiophenyl, 4-trifluoromethylthiophenyl, 2-ethylphenyl, 3ethylphenyl, 4-ethylphenyl, 2-methoxycarbonylphenyl, 3-methoxycarbonylphenyl, 4-methoxycarbonylphenyl, 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-2-yl, pyrimidin-5-yl, pyrimidin-4-yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2-ylmethyl, 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, 1naphthylmethyl, quinolin-4-ylmethyl, quinolin-6-ylmethyl, quinolin- 8-ylmethyl, quinolin-2-ylmethyl, quinoxalin-2-ylmethyl, pyrazin-2-ylmethyl, 4-chloropyridin-2-yl, 3-chloropyridin-4-yl, 2-chloropyridin-3-yl, 2chloropyridin-4- yl, 2-chloropyridin-5-yl, 2,6-dichloropyridin-4-yl, 3-chloropyridin-5-yl, 3,5-dichloropyridin-2-yl, 3-chloro-5-trifluoromethylpyridin-2-yl, (4 -chloropyridin-2-yl)methyl, (3-chloropyridin-4-yl)methyl, (2-chloropyridin-3-yl)methyl, (2-chloropyridin-4-yl)methyl, (2-chloropyridin-5yl)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-2yl, 4-methylthiophen-2-yl, 3-methylthiophen-2-yl, 5-fluorothiophen-3- yl, 3,5-dimethylthiophen-2-yl, 3-ethylthiophen-2-yl, 4,5-dimethylthiophen-2-yl, 3,4-dimethylthiophen-2-yl, 4-chlorothiophen-2-yl, furan-2- yl, 5-methylfuran-2-yl, 5-ethylfuran-2-yl, 5-methoxycarbonylfuran-2-yl, 5-chlorofuran-2-yl, 5-bromofuran-2yl, 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-(4-methylphenyl)ethyl, 1-(3- methylphenyl)ethyl, 1(2-methylphenyl)ethyl, 1-(4-chlorophenyl)ethyl, 1-(3-chlorophenyl)ethyl, 1-(2-chlorophenyl)ethyl, benzyl, (4fluorophenyl)methyl, (3-fluorophenyl )methyl, (2-fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3,5difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6-difluorophenyl)methyl, (2,4,5 -trifluorophenyl)methyl, (2,4,6-trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3-chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4dichlorophenyl)methyl, (3,5-dichlorophenyl )methyl, (2,5-dichlorophenyl)methyl, (2,6-dichlorophenyl)methyl, (2,4,5 - 126 042986 trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, (4-bromophenyl)methyl, (3-bromophenyl)methyl, (2bromophenyl)methyl, (4-iodophenyl)methyl, (3-iodophenyl)methyl , (2-iodophenyl)methyl, (3-chloro-5trifluoromethylpyridin-2-yl)methyl, (2-bromo-4-fluorophenyl)methyl, (2-bromo-4-chlorophenyl)methyl, (3-bromo-4fluorophenyl) 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, (3-fluoro-4-bromophenyl)methyl, (3chloro-4-bromophenyl)methyl, (2-chloro-4-fluorophenyl)methyl, (3-chloro-4-fluorophenyl)methyl, ( 2-fluoro-3chlorophenyl)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, 3-trifluoromethyl-4-chlorophenyl, 3-chloro-4-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5-difluoropyridine -2-yl, (3,6dichloropyridin-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, (4methylphenyl)methyl, (3-methylphenyl)methyl, (2-methylphenyl)methyl, (4 -cyanophenyl)methyl, (3-cyanophenyl)methyl, (2-cyanophenyl)methyl, (2,4-diethylphenyl)methyl, (3,5-diethylphenyl)methyl, (3,4-dimethylphenyl)methyl, (3.5 -dimethoxyphenyl)methyl, 1-phenylethyl-1-yl, 1-(o-chlorophenyl)eth-1-yl, 1,3-thiazol-2-yl, 4methyl-1,3-thiazol-2-yl, 1, 3-thiazol-2-yl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, npropylthiomethyl, isopropylthiomethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, nbutyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl , benzyloxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, methyl(ethyl)aminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, allylaminocarbonyl, benzylaminocarbonyl, tert-butyloxycarbonylaminocarbonyl yl, hydroxycarbonylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, nbutyloxycarbonylmethyl, tert- butyloxycarbonylmethyl, allyloxycarbonylmethyl, benzyloxycarbonylmethyl, aminocarbonylmethyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, npropylaminocarbonylmethyl, isopropylaminocarbonylmethyl, dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, methyl(ethyl)aminocarbonylmethyl, cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl, cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl, allylaminocarbonylmethyl, benzylaminocarbonylmethyl, aminomethyl, 2-aminoeth-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, 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 ⁷ and R ⁸ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I) below m is 0; n is 0, 1, 2, 3, 4, 5, 6; R ²¹ is fluorine; R ²² and R ²³ independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1- methylbutyl, 2methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, ethenyl, 1-propenyl, 1-methylethenyl, 1-butenyl, phenyl, or R ²² and R ²³ together with the carbon atom to which they are attached form a 3-10 membered monocyclic or bicyclic ring which is saturated, and - 127 042986 Q is one of the Q-1-Q-345 fragments below: --- ___ Q-1 Q-2 Q-3 Q-4 Q-5 Ό ^/O ^°X1 _F Q-6 Q-7 Q-8 Q-9 Q-10 XX χθχ/^/χ/χ ^°^°^d _Br R and Q-ll Q-12 Q-13 Q-14 Q-15 Cl /O^q/vX X'Xi y___ ZθΧ^Ο^^γί ¹¹ F Q-16 Q-17 Q-18 Q-19 Q-20 XT ___ °— Q-21 Q-22 Q-23 Q-24 Q-25 Q-26 Q-27 Q-28 Q-29 Q-30 Z°xZ^s^ z°^ _s X R___-\.Z4^\ Ό Q-31 Q-32 Q-33 Q-34 Q-35 x _o ^ _s X Q-3 6 Q-3 7 Q-3 8 Q-3 9 Q-40 /θ^Ο' ⁰² ^ Q-41 Q-42 Q-43 Q-44 Q-45 __^ _s ^CF ₃ X ⁰ \^S ^zC2Fs ^0---^S' ⁰² ^ \ _o ^^s^Y ^F Q-46 Q-47 Q-48 Q-49 Q-50 z°^Xo^ ___ ΖθχΧ'Ο'' /θχΧο^ Q-51 Q-52 Q-53 Q-54 Q-55 ^o^x^cZ ^o^2^° ^x Q-56 Q-57 Q-58 Q-59 Q-60 ^0X^0^ \ _o Xo ^z Xo-X/'O'X Q-61 Q-62 Q-63 Q-64 Q-65 ^ _ο ^οΧι /°—^°—^0^ Z°x^-°—^0^ Q-66 Q-67 Q-68 Q-69 Q-70 - 128 042986 /°^C° /°^p° Q-71 Q-72 Q-73 Q-74 Q-75 /°^ς χ°γΌ _x °yC° Q-76 Q-77 Q-78 Q-79 Q-80 _x °^C ^s o ^°^C ^s=o Q-81 Q-82 Q-83 Q-84 Q-85 sax No. °\ Q-86 Q-87 Q-88 Q-89 Q-90 [^° Q-91 Q-92 Q-93 Q-94 Q-95 /oQ r^ ⁰ /θγ^ο^ Q-96 Q-97 Q-98 Q-99 Q-100 ζ°γ-ο/ Q-101 Q-102 Q-103 Q-104 Q-105 X°^O χ°^Ο [^5 X°X^\X^ X°x^>0 ^S /^0 X°xXV - 129 042986 Q-106 I Q-107 Q-108 Q-109 Q-110 x°aX^ II o ao Q-lll Q-112 Q-113 Q-114 Q-115 d'O Ό A xS=0 x p _Z °A\/ o r~~S=Q /O. As Q-116 Q-117 Q-118 Q-119 Q-120 χ°χχ\ Co χ°χχ\ Cq^ χ°χχ\ Cs eV '0 / ^0> ^\ > Q-121 Q-122 Q-123 Q-124 Q-125 X°VA χ'θχχΑ' A ⁰ Q-126 Q-127 Q-128 Q-129 Q-130 ΧθΆΑ A ^s ^Ο^χχχ A® Ά Q-131 Q-132 Q-133 Q-134 Q-135 I Χθ'γ'Α χΟχχχ/ τχ χθνΑ^ XX ^χΟ τΧ° Co ^z Q-136 Q-137 Q-138 Q-139 Q-140 X°VA O' '0 ✓ °χχ\ A ΧθΆ^Α 4 Χ°χχ\/ I s*° 0 χθχχ^ J Co Q-141 Q-142 Q-143 Q-144 Q-145 - 130 042986 .O___ J ^O.___ ^o___ Q-146 Q-147 Q-148 Q-149 Q-150 H H H H Λ Q-151 Q-152 Q-153 Q-154 Q-155 H H H H Q-156 Q-157 Q-158 Q-159 Q-160 H H J] ϊ ^H T Q-161 Q-162 Q-163 Q-164 Q-165 H Cl ^{/< Lo} and H F H F ' I ^l s. Q-166 Q-167 Q-168 Q-169 Q-170 n H H Q-171 Q-172 Q-173 Q-174 Q-175 H H H Q-176 Q-177 Q-178 Q-179 Q-180 H H / ^N ^s---' H h X^S^J Q-181 Q-182 Q-183 Q-184 Q-185 H H H Q-186 Q-187 Q-188 Q-189 Q-190 H _X <^ _o xCF3 H ^m^^ _O ' ^C|:z H H HF Q-191 Q-192 Q-193 Q-194 Q-195 H J^gxCFa H /N^sx^Fe ^N^X^r ⁰¹¹³ H Xn^x^s' ⁰²¹¹⁵ H HF Q-196 Q-197 Q-198 Q-199 Q-200 h | x^o- Q-201 Q-202 Q-203 Q-204 Q-205 Q-206 Q-207 Q-208 Q-209 Q-210 H H H H Q-211 Q-212 Q-213 Q-214 Q-215 H Xn^^x x/ Xn-^Xx x/0 H H Q-216 Q-217 Q-218 Q-219 Q-220 H ,—\ H r^X ^H rw Ν xU? ^H r^\ N^JJo Q-221 Q-222 Q-223 Q-224 Q-225 - 131 042986 n r^\/ hr~\ N Ay° Η rX N ly° n i—\ /MV H r^\ N JCt ⁰ Q-226 Q-227 Q-228 Q-229 Q-230 H H H 1—\ H r—\ 0f^s=o H Q-231 Q-232 Q-233 Q-234 Q-235 J Г>° Ό η AA / ^N X^O ^? η Άλ ν AE ⁰ n^C/° A Q-236 Q-237 Q-238 Q-239 Q-240 ^H KV H ✓N^jx^o n H H Q-241 Q-242 Q-243 Q-244 Q-245 ^H ίΆ / ^N VA ₀ > n AA h A^o ΑχΑΑ Q-246 Q-247 Q-248 Q-249 Q-250 n AA /AV n AAA. O H H Q-251 Q-252 Q-253 Q-254 Q-255 ^H ίΆ h A^s ir~S Q-256 Q-257 Q-258 Q-259 Q-260 ^H (Ά A^xAs^ II 0 h AA h A^s*° <AH° H A3) Q-261 Q-262 Q-263 Q-264 Q-265 ^H πΆ ό'Ό ^H A /N^JV/Sr ⁰ 'b p o H A?s Q-266 Q-267 Q-268 Q-269 Q-270 H H H H H / ΥΛ XX A^X\ V oA Ά A; 'o A° Q-271 Q-272 Q-273 Q-274 Q-275 H H ^x° H H Q-276 Q-277 Q-278 Q-279 Q-280 A^x^A Xs^ H H X^ ^s H HZ ^N Xo Q-281 Q-282 Q-283 Q-284 Q-285 H H H H H Α^χΑΑ / 1 Ari Ag g— A xA^o x^Aq 'xAo Vo Q-286 Q-287 Q-288 Q-289 Q-290 H H H H ^n^Aa ζ ^Ν νά J XsP ο' Ό L ^s=o 'b AXs=o '6 As*° '6 Vo ^Z Q-291 Q-292 Q-293 Q-294 Q-295 - 132 042986 n n n n Q-296 Q-297 Q-298 Q-299 Q-300 z ^N ^o-^ Q-301 Q-302 Q-303 Q-304 Q-305 1 1 1 Q-306 Q-307 Q-308 Q-309 Q-310 ^n^C° । ABOUT . About ¹ f^? Q-311 Q-312 Q-313 Q-314 Q-315 1 । Γ9 Q-316 Q-317 Q-318 Q-319 Q-320 ^x o I—k |XX| Q-321 Q-322 Q-323 Q-324 Q-325 % % I N JU ⁰ % '6 ^H θ Q-326 Q-327 Q-328 Q-329 Q-330vO h o-^ h o^X o Η Ο--Λ N JO° v Q-331 Q-332 Q-333 Q-334 Q-335 H r-\ X ^N xx^o ^? CFs ⁿ GL uuU ³ CF ₃ 4 V /// % Q-336 Q-337 Q-338 Q-339 Q-340 ^x o 'O ^H ? ^ΌH ° Q-341 Q-342 Q-343 Q-344 Q-345 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 represents 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, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, methoxy-n-propyl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4 - 133 042986 fluorophenyl, 2,4-difluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, pyridin-2-yl , pyridin-3-yl, pyridin-4-yl, thiophen-2yl, thiophen-3-yl, furan-2-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, phenylethyl, 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, (2fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3,5-difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6difluorophenyl)methyl, (4 -chlorophenyl)methyl, (3-chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4-dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl, (2,5-dichlorophenyl)methyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, n-propylthiomethyl, 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 to 10-membered monocyclic or bicyclic ring, or R ⁵ and R ⁶ together with the carbon atom to which they are bonded form a double bond optionally substituted with R ²² and R ²³ according to formula (I') below R ⁷ and R ⁸ 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, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl- 3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1- methyl-2pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, 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, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 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, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, pyridin-2-yl, pyridin-3- yl, pyridin-4-yl, thiophen-2yl, thiophen-3-yl, furan-2-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 1-(4-methylphenyl)ethyl, 1-(3methylphenyl) 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, (2,4difluorophenyl)methyl, (3,5-difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6-difluorophenyl)methyl, (2,4, 5trifluorophenyl)methyl, (2,4,6-trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3-chlorophenyl)methyl, (2chlorophenyl)methyl, (2,4-dichlorophenyl)methyl, (3,5-dichlorophenyl) methyl, (2,5-dichlorophenyl)methyl, (2,6dichlorophenyl)methyl, (2,4,5-trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methylthioethyl, n- propylthiomethyl, isopropylthiomethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl, 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 ⁷ and R ⁸ together with the carbon atom to which they are bonded form a double bond, optionally substituted with R ²² and R ²³ according to formula (I'') below - 134 042986 m equals 0; n is 0, 1, 2, 3; R ²¹ is fluorine; R ²² and R ²³ independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, ethenyl, 1-propenyl, 1-methylethenyl, 1-butenyl, phenyl, or R ²² and R ²³ together with the carbon atom to which they are attached form a 3-10 membered monocyclic or bicyclic ring which is saturated, and Q is one of the fragments Q-1-Q-345 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 their salts 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.