[(1,4,5-trisubstituted 1H-pyrazol-3-yl)sulfanyl]acetic acid derivatives and salts thereof and use thereof as active herbicidal ingredients

Abstract

The present invention relates to the technical field of plant protection agents, in particular to the technical field of herbicides for controlling weeds and grasses in the cultivation of useful plants. In particular, the present invention relates to novel substituted [(1,4,5-trisubstituted-1H-pyrazol-3-yl)sulfanyl]acetic acid derivatives of formula (I) or agrochemically acceptable salts thereof, methods for their preparation and their use as herbicides.

Description

[0001] The present invention relates to the technical field of crop protection products, in particular to the technical field of herbicides for controlling broad-leaved weeds and weed grasses in crops of useful plants.

[0002] Specifically, the present invention relates to novel substituted [(1,4,5-trisubstituted 1H-pyrazol-3-yl)sulfanyl]acetic acid derivatives of formula (I) or agrochemically acceptable salts thereof, a preparation method thereof and use thereof as herbicides.

[0003] Crop protection products for controlling harmful plants in crops of useful plants or active ingredients for controlling unwanted vegetation known to date sometimes have disadvantages when used: namely (a) no or insufficient herbicidal activity against specific harmful plants, (b) the range of harmful plants that can be controlled by the active ingredients is not wide enough, (c) the selectivity in crops of useful plants is too low and / or (d) there are toxicologically unfavorable characteristics. In addition, some active ingredients that can be used as plant growth regulators for many useful plants lead to an undesirable reduction in the harvest yield of other useful plants or are only compatible with crop plants within a narrow application rate range, if at all. Due to difficult to obtain precursors and reagents, or simply their insufficient chemical stability, some known active ingredients cannot be produced economically on an industrial scale. In the case of other active ingredients, the activity is too dependent on environmental conditions, such as weather and soil conditions.

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

[0005] EP1122244 describes 2-({4-[5-(4-tert-butyl-3-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-2-chloro-4-fluorophenoxy]-1,5-dimethyl-1H-pyrazol-3-yl}sulfanyl)propionic acid derivatives as herbicides. WO2018 / 080859 describes [(1,5-disubstituted 1H-pyrazol-3-yl)sulfanyl]acetic acid derivatives having fungicidal properties. Russian Chemical Bulletin 2010, 59(9), 1786-1790 and Yakugaku Zasshi 1971, 91(3), 311-323 disclose the synthesis of [(1,5-dimethyl-4-nitro-1H-pyrazol-3-yl)sulfanyl]acetic acid derivatives and 1,2,3,4-tetrasubstituted 3-pyrazoline-5-thione derivatives. Ethyl {[4-nitro-1-phenyl-5-(1H-tetrazol-5-yl)-1H-pyrazol-3-yl]sulfanyl}acetate CAS [1360702-86-8], ethyl {[5-(dichloromethyl)-4-nitro-1-phenyl-1H-pyrazol-3-yl]sulfanyl}acetate CAS [1360691-01-5], methyl {[5-(dichloromethyl)-4-nitro-1-phenyl-1H-pyrazol-3-yl]sulfanyl}acetate CAS [1360690-82-9] and methyl {[5-(5-methyl-1,3,4-oxadiazol-2-yl)-4-nitro-1-phenyl-1H-pyrazol-3-yl]sulfanyl}acetate CAS [1360690-60-3] are mentioned without giving a reference.

[0006] In contrast, there has been no description to date of using [(1,4,5-trisubstituted 1H-pyrazol-3-yl)sulfanyl]acetic acid derivatives or salts thereof, which carry one of the phenyl or heteroaryl groups having defined substitutions on the pyrazole, as active herbicidal ingredients. It has now surprisingly been found that substituted [(1,4,5-trisubstituted 1H-pyrazol-3-yl)sulfanyl]acetic acid derivatives or salts thereof, which carry one of the phenyl or heteroaryl groups having defined substitutions on the pyrazole, as active herbicidal ingredients, are particularly suitable as herbicides.

[0007] The present invention therefore provides a substituted [(1,4,5-trisubstituted 1H-pyrazol-3-yl)sulfanyl]acetic acid derivative of formula (I) or an agrochemically acceptable salt thereof,

[0008]

[0009] in:

[0010] Q 1 is phenyl or heteroaryl,

[0011] wherein the phenyl and heteroaryl groups are unsubstituted or are each independently substituted by m groups selected from the group consisting of hydrogen, halogen, cyano, isocyano, nitro, hydroxyl, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halogenated cycloalkyl, (C 1 -C 6 )-haloalkoxy, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C1 -C 6 )-alkoxy, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 4 )-Alkyl-S(O) n , (C 1 -C 4 )-Haloalkyl-S(O) n 、CHO、(C 1 -C 4 )-alkoxycarbonyl and NH 2 (amino),

[0012] Q 2 is phenyl,

[0013] which is unsubstituted or substituted independently in each case by m groups selected from the group consisting of hydrogen, halogen, cyano, isocyano, NO 2 , (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxy, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halogenated cycloalkyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 1 -C 6 )-alkoxy, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 4 )-Alkyl-S(O) n , (C 1 -C 4 )-Haloalkyl-S(O) n 、CHO、(C 1 -C 4 )-alkoxycarbonyl and NH 2 (amino),

[0014] Z is a group

[0015]

[0016] and

[0017]

[0018] Y is halogen, cyano, isocyano, NO 2 NH 2 (amino), (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-cyanoalkyl, (C 1 -C 6 )-hydroxyalkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, CHO, (C 3 -C 6 )-halogenated cycloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 4 )-Alkyl-S(O) n , (C 1 -C 4 )-Haloalkyl-S(O) n , (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkenyl and (C 2 -C 6 )-haloalkenyl,

[0019] W is oxygen or sulfur,

[0020] R 1 For hydrogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halogenated cycloalkyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkenyl and (C 2 -C 6 )-haloalkenyl,

[0021] R 2 For hydrogen, (C 1 -C 10 )-alkyl and (C 3 -C 10 )-cycloalkyl,

[0022] wherein the alkyl and cycloalkyl are unsubstituted or are each independently substituted by m groups selected from the group consisting of halogen, cyano, isocyano, nitro, NH 2 (amino), (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxy, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 1 -C 6 )-alkoxy, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 4 )-Alkyl-S(O) n 、CHO、(C 1 -C 4 )-alkoxycarbonyl, heterocyclic-(C 1 -C 4 )-alkyl, heteroaryl-(C 1 -C 4 )-alkyl and aryl-(C1 -C 4 )-alkyl, wherein the aryl, heterocyclyl and heteroaryl are unsubstituted or each independently substituted by m selected from halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl group,

[0023] R 3 For hydrogen and (C 1 -C 12 )-alkyl,

[0024] R 4 for hydrogen, cyano, nitro, (C 1 -C 12 )-alkyl, (C 1 -C 10 )-haloalkyl, (C 2 -C 10 )-alkenyl, (C 3 -C 10 )-alkynyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-Haloalkoxy-(C 1 -C 10 )-alkyl, (C 1 -C 4 )-Alkyl-S(O) n -(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Haloalkyl-S(O) n -(C 1 -C 4 )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 10 )-halogenated cycloalkyl, hydroxy-(C 1 -C 10 )-alkylcarbonyl, amino-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkoxycarbonyl-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-Cyanoalkyl, S(O)n R 5 , OR 5 、SO 2 NR 6 R 7 , CO 2 R 8 , COR 8 NR 6 R 8 NR 6 COR 8 NR 6 CO 2 R 8 NR 6 SO 2 R 8 , aryl, heteroaryl and heterocyclic groups,

[0025] which are unsubstituted or are independently substituted by m groups selected from the group consisting of hydrogen, halogen, cyano, nitro, OR 5 、S(O) n R 5 、SO 2 NR 6 R 7 , CO 2 R 8 ,CONR 6 R 8 , COR 6 NR 6 R 8 NR 6 COR 8 NR 6 CONR 8 R 8 NR 6 CO 2 R 8 NR 6 SO 2 R 8 NR 6 SO 2 NR 6 R 8 , C(R 6 )=NOR 8 ;

[0026] or

[0027] R 3 and R 4 together with the nitrogen atom to which they are bound, form a fully saturated or partially saturated 3- to 10-membered monocyclic or bicyclic ring, which is optionally interrupted by heteroatoms and optionally has further substitutions,

[0028] R5 For hydrogen, (C 1 -C 8 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 8 )-haloalkyl and aryl, R 6 for hydrogen and R 5 ,

[0029] R 7 For hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 4 )-alkenyl, (C 3 -C 4 )-alkynyl and (C 1 -C 10 )-alkylcarbonyl-(C 1 -C 6 )-alkyl,

[0030] R 8 For hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 4 )-alkenyl and (C 3 -C 4 )-alkynyl,

[0031] m is 0, 1, or 2,

[0032] and

[0033] n is 0, 1, or 2,

[0034] The compounds ethyl {[4-nitro-1-phenyl-5-(1H-tetrazol-5-yl)-1H-pyrazol-3-yl]sulfanyl}acetate CAS [1360702-86-8] and methyl {[5-(5-methyl-1,3,4-oxadiazol-2-yl)-4-nitro-1-phenyl-1H-pyrazol-3-yl]sulfanyl}acetate CAS [1360690-60-3] are excluded.

[0035] Compounds of general formula (I) can be prepared by adding a suitable inorganic or organic acid (e.g., an inorganic acid (e.g., HCl, HBr, H 2 SO 4 , H 3PO 4 or HNO 3 ), or an organic acid (e.g., a carboxylic acid such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or a sulfonic acid, such as p-toluenesulfonic acid)) to form a salt. In such a case, these salts contain the conjugate base of the acid as an anion. Suitable substituents in deprotonated form such as sulfonic acids (especially sulfonamides) or carboxylic acids can form inner salts with groups that can be protonated themselves, such as amino groups. Salts can also be formed by the action of a base on a compound of general formula (I). Suitable bases are, for example, organic amines (e.g., trialkylamines, morpholine, piperidine and pyridine), as well as hydroxides, carbonates and bicarbonates of ammonium, alkali metals or alkaline earth metals, especially sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, such as a metal salt, especially an alkali metal salt or an alkaline earth metal salt, especially a sodium salt and a potassium salt, or an ammonium salt, a salt with an organic amine or a quaternary ammonium salt, for example, having the formula [NR a R b R c R d ] + A salt of a cation, wherein R a To R d Each is independently an organic group, in particular an alkyl, aryl, arylalkyl or alkylaryl group. Also suitable are alkylsulfonium and alkylsulfonium oxide salts, such as (C 1 -C 4 )-trialkylsulfonium and (C 1 -C 4 )-trialkylsulfonium oxide salts.

[0036] Depending on external conditions such as pH, solvent and temperature, the substituted [(1,4,5-trisubstituted 1H-pyrazol-3-yl)sulfanyl]acetic acid derivatives of the general formula (I) of the present invention may exist in various tautomeric structures, all of which are encompassed by the general formula (I).

[0037] The compounds of formula (I) and their salts used according to the invention are referred to hereinafter as "compounds of general formula (I)".

[0038] The present invention Best Provided are compounds of formula (I), wherein

[0039] Q 1 For group Q 1 -1.1 to Q 1 -6.5

[0040]

[0041]

[0042] Q2 is phenyl,

[0043] which is unsubstituted or substituted independently in each case by m groups selected from the group consisting of hydrogen, halogen, cyano, isocyano, NO 2 , (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxy, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halogenated cycloalkyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 1 -C 6 )-alkoxy, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 4 )-Alkyl-S(O) n , (C 1 -C 4 )-Haloalkyl-S(O) n 、CHO、(C 1 -C 4 )-alkoxycarbonyl and NH 2 (amino),

[0044] Z is a group

[0045]

[0046] and

[0047]

[0048] Y is halogen, cyano, isocyano, NO 2 NH 2 (amino), (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-cyanoalkyl, (C 1 -C 6 )-hydroxyalkyl, (C 1-C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, CHO, (C 3 -C 6 )-halogenated cycloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 4 )-Alkyl-S(O) n , (C 1 -C 4 )-Haloalkyl-S(O) n , (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkenyl and (C 2 -C 6 )-haloalkenyl,

[0049] W is oxygen or sulfur,

[0050] R 1 For hydrogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halogenated cycloalkyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkenyl and (C 2 -C 6)-haloalkenyl,

[0051] R 2 For hydrogen, (C 1 -C 10 )-alkyl and (C 3 -C 10 )-cycloalkyl,

[0052] wherein the alkyl and cycloalkyl are unsubstituted or are each independently substituted by m groups selected from the group consisting of halogen, cyano, isocyano, nitro, NH 2 (amino), (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxy, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 1 -C 6 )-alkoxy, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 4 )-Alkyl-S(O) n 、CHO、(C 1 -C 4 )-alkoxycarbonyl, heterocyclic-(C 1 -C 6 )-alkyl, heteroaryl-(C 1 -C 4 )-alkyl and aryl-(C 1 -C 4 )-alkyl, wherein the aryl, heterocyclyl and heteroaryl are unsubstituted or each independently substituted by m selected from halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl group,

[0053] R 3 For hydrogen and (C 1 -C 10 )-alkyl,

[0054] R 4 for hydrogen, cyano, nitro, (C 1 -C 10 )-alkyl, (C 1-C 10 )-haloalkyl, (C 2 -C 10 )-alkenyl, (C 3 -C 10 )-alkynyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-Haloalkoxy-(C 1 -C 10 )-alkyl, (C 1 -C 4 )-Alkyl-S(O) n -(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Haloalkyl-S(O) n -(C 1 -C 4 )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 10 )-halogenated cycloalkyl, hydroxy-(C 1 -C 10 )-alkylcarbonyl, amino-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkoxycarbonyl-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-Cyanoalkyl, S(O) n R 5 , OR 5 、SO 2 NR 6 R 7 , CO 2 R 8 , COR 8 NR 6 R 8 NR 6 COR 8 NR 6 CO 2 R 8 NR 6 SO 2 R 8 , aryl, heteroaryl and heterocyclic groups,

[0055] which are unsubstituted or are independently substituted by m groups selected from the group consisting of hydrogen, halogen, cyano, nitro, OR 5 、S(O) n R 5 、SO 2 NR 6 R 7 , CO 2 R 8 ,CONR 6 R 8 , COR 6 NR 6 R 8 NR 6 COR 8 NR 6 CONR 8 R 8 NR 6 CO 2 R 8 NR 6 SO 2 R 8 NR 6 SO 2 NR 6 R 8 , C(R 6 )=NOR 8 ;

[0056] or R 3 and R 4 together with the nitrogen atom to which they are bound, form a fully saturated or partially saturated 3- to 10-membered monocyclic or bicyclic ring, which is optionally interrupted by heteroatoms and optionally has further substitutions,

[0057] R 5 For hydrogen, (C 1 -C 8 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 8 )-haloalkyl and aryl,

[0058] R 6 for hydrogen and R 5 ,

[0059] R 7 For hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 4 )-alkenyl, (C3 -C 4 )-alkynyl and (C 1 -C 6 )-alkylcarbonyl-(C 1 -C 4 )-alkyl,

[0060] R 8 For hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 4 )-alkenyl and (C 3 -C 4 )-alkynyl,

[0061] R 9 is hydrogen, halogen, cyano, isocyano, nitro, hydroxyl, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxy, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 1 -C 6 )-alkoxy, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 4 )-Alkyl-S(O) n 、CHO、(C 1 -C 4 )-alkoxycarbonyl and NH 2 (amino),

[0062] m is 0, 1, and 2,

[0063] n is 0, 1 and 2.

[0064] The present invention More preferred Provided are compounds of formula (I), wherein

[0065] Q 1 For group Q 1 -1.1 to Q 1 -6.3,

[0066]

[0067]

[0068] Q 2 is phenyl,

[0069] which is unsubstituted or substituted independently in each case by m groups selected from the group consisting of hydrogen, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxy, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 4 )-Alkyl-S(O) n and (C 1 -C 4 )-Haloalkyl-S(O) n ,

[0070] Z is a group

[0071]

[0072] and

[0073]

[0074] Y is halogen, cyano, isocyano, NO 2 , (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 4 )-Alkyl-S(O) n , (C 1 -C 4)-Haloalkyl-S(O) n , (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkenyl and (C 2 -C 6 )-haloalkenyl,

[0075] W is oxygen,

[0076] R 1 For hydrogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkenyl and (C 2 -C 6 )-haloalkenyl,

[0077] R 2 For hydrogen, (C 1 -C 6 )-alkyl and (C 3 -C 6 )-cycloalkyl,

[0078] wherein the alkyl and cycloalkyl are unsubstituted or each independently substituted by m groups selected from the group consisting of halogen, cyano, nitro, NH 2 (amino), (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxy, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C1 -C 6 )-alkoxy, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 4 )-Alkyl-S(O) n 、CHO、(C 1 -C 4 )-alkoxycarbonyl, heterocyclic-(C 1 -C 4 )-alkyl, heteroaryl-(C 1 -C 4 )-alkyl and aryl-(C 1 -C 4 )-alkyl, wherein the aryl, heterocyclyl and heteroaryl are unsubstituted or each independently substituted by m selected from halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl group,

[0079] R 3 For hydrogen and (C 1 -C 6 )-alkyl,

[0080] R 4 for hydrogen, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-Haloalkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-Alkyl-S(O) n -(C 1 -C 4 )-alkyl and (C 1 -C 4 )-Haloalkyl-S(O) n -(C 1 -C4 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halogenated cycloalkyl, hydroxy-(C 1 -C 6 )-alkylcarbonyl, amino-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, S(O) n R 5 , OR 5 、SO 2 NR 6 R 7 , CO 2 R 8 , COR 8 NR 6 R 8 NR 6 COR 8 NR 6 CO 2 R 8 NR 6 SO 2 R 8 ; aryl, heteroaryl and heterocyclic groups,

[0081] which are unsubstituted or are independently substituted by m groups selected from the group consisting of hydrogen, halogen, cyano, nitro, OR 5 、S(O) n R 5 、SO 2 NR 6 R 7 , CO 2 R 8 ,CONR 6 R 8 , COR 6 NR 6 R 8 NR 6 COR 8 NR 6 CONR 8 R 8 NR 6 CO 2 R 8 NR 6 SO 2 R 8 NR 6 SO2 NR 6 R 8 , C(R 6 )=NOR 8 ;

[0082] or R 3 and R 4 together with the nitrogen atom to which they are bound, form a fully saturated or partially saturated 3- to 10-membered monocyclic or bicyclic ring, which is optionally interrupted by heteroatoms and optionally has further substitutions,

[0083] R 5 For hydrogen, (C 1 -C 8 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 8 )-haloalkyl and aryl,

[0084] R 6 for hydrogen and R 5 ,

[0085] R 7 For hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 4 )-alkenyl and (C 3 -C 4 )-alkynyl,

[0086] R 8 For hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 4 )-alkenyl, (C 3 -C 4 )-alkynyl and (C 1 -C 10 )-alkylcarbonyl-(C 1 -C 6 )-alkyl,

[0087] R 9 is hydrogen, halogen, cyano, isocyano, nitro, hydroxyl, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C6 )-haloalkoxy, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 1 -C 6 )-alkoxy, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 4 )-Alkyl-S(O) n 、CHO、(C 1 -C 4 )-alkoxycarbonyl and NH 2 (amino),

[0088] m is 0, 1, and 2,

[0089] n is 0, 1 and 2.

[0090] The present invention Even more preferred Provided are compounds of formula (I), wherein

[0091] Q 1 For group Q 1 -1.1 to Q 1 -6.3,

[0092]

[0093] Q 2 is phenyl,

[0094] which is unsubstituted or substituted, independently in each case, by m groups selected from hydrogen, fluorine, chlorine and bromine,

[0095] Z is a group

[0096]

[0097] and

[0098]

[0099] Y is fluorine, chlorine, bromine, cyano, NO 2 , (C 1 -C 2 )-alkyl, (C 1 -C 2 )-haloalkyl, (C 1 -C 2 )-alkylcarbonyl, (C 1 -C 2 )-alkoxy, (C1 -C 2 )-haloalkoxy, (C 1 -C 2 )-Alkyl-S(O) n and (C 1 -C 2 )-Haloalkyl-S(O) n ,

[0100] W is oxygen,

[0101] R 1 For hydrogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl and (C 1 -C 6 )-alkoxy,

[0102] R 2 For hydrogen, (C 1 -C 6 )-alkyl and (C 3 -C 6 )-cycloalkyl,

[0103] wherein the alkyl and cycloalkyl are unsubstituted or each independently substituted by m groups selected from the group consisting of halogen, cyano, nitro, NH 2 (amino), (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxy, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 1 -C 6 )-alkoxy, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 4 )-Alkyl-S(O) n 、CHO、(C 1 -C 4 )-alkoxycarbonyl, heterocyclic-(C 1 -C 4 )-alkyl, heteroaryl-(C 1 -C 4 )-alkyl and aryl-(C1 -C 4 )-alkyl, wherein the aryl, heterocyclyl and heteroaryl are unsubstituted or each independently substituted by m selected from halogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl group,

[0104] R 3 For hydrogen and (C 1 -C 6 )-alkyl,

[0105] R 4 for hydrogen, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-Haloalkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-Alkyl-S(O) n -(C 1 -C 4 )-alkyl and (C 1 -C 4 )-Haloalkyl-S(O) n -(C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halogenated cycloalkyl, hydroxy-(C 1 -C 6 )-alkylcarbonyl, amino-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, S(O) n R 5 , OR5 、SO 2 NR 6 R 7 , CO 2 R 8 , COR 8 NR 6 R 8 NR 6 COR 8 NR 6 CO 2 R 8 NR 6 SO 2 R 8 ; aryl, heteroaryl and heterocyclic groups,

[0106] which are unsubstituted or are independently substituted by m groups selected from the group consisting of hydrogen, halogen, cyano, nitro, OR 5 、S(O) n R 5 、SO 2 NR 6 R 7 , CO 2 R 8 ,CONR 6 R 8 , COR 6 NR 6 R 8 NR 6 COR 8 NR 6 CONR 8 R 8 NR 6 CO 2 R 8 NR 6 SO 2 R 8 NR 6 SO 2 NR 6 R 8 , C(R 6 )=NOR 8 ;

[0107] or R 3 and R 4 together with the nitrogen atom to which they are bound, form a fully saturated or partially saturated 3- to 10-membered monocyclic or bicyclic ring, which is optionally interrupted by heteroatoms and optionally has further substitutions,

[0108] R 5 For hydrogen, (C 1 -C 8 )-alkyl, (C3 -C 6 )-cycloalkyl, (C 1 -C 8 )-haloalkyl and aryl,

[0109] R 6 for hydrogen and R 5 ,

[0110] R 7 For hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 4 )-alkenyl, (C 3 -C 4 )-alkynyl and (C 1 -C 10 )-alkylcarbonyl-(C 1 -C 6 )-alkyl,

[0111] R 8 For hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 4 )-alkenyl and (C 3 -C 4 )-alkynyl,

[0112] R 9 is hydrogen, halogen, cyano, isocyano, nitro, hydroxyl, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxy, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 1 -C 6 )-alkoxy, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 4 )-Alkyl-S(O) n 、CHO、(C 1 -C4 )-alkoxycarbonyl and NH 2 (amino),

[0113] m is 0, 1, and 2,

[0114] n is 0, 1 and 2.

[0115] The present invention Especially preferred Provided are compounds of formula (I), wherein

[0116] Q 1 For group Q 1 -1.1 to Q 1 -5.7

[0117]

[0118] Q 2 is phenyl,

[0119] which is unsubstituted or substituted, independently in each case, by m groups selected from hydrogen, fluorine, chlorine and bromine,

[0120] Z is a group

[0121]

[0122] and

[0123]

[0124] Y is fluorine, chlorine, bromine, cyano, NO 2 , methyl, CF 3 and OCF 3 ,

[0125] W is oxygen,

[0126] R 1 are hydrogen, methyl and ethyl,

[0127] R 2 is hydrogen, methyl, ethyl, allyl, propargyl and PhCH 2 ,

[0128] R 3 For hydrogen,

[0129] R 4 For (C 1 -C 6 )-alkyl, S(O) n R 5 , OR 5 、SO 2 NR 6 R 7 , CO 2 R8 , COR 8 ,

[0130] which are unsubstituted or are in each case independently of one another substituted by m selected from hydrogen, OR 5 、S(O) n R 5 、SO 2 NR 6 R 7 , CO 2 R 8 , COR 6 NR 6 CO 2 R 8 substituted by a group

[0131] R 5 Methyl, ethyl, CF 3 , CH 2 CF 3 ,

[0132] R 6 for hydrogen and R 5 ,

[0133] R 7 is hydrogen, methyl, ethyl and ethyl-2-acetyl,

[0134] R 8 For methyl and ethyl,

[0135] R 9 is hydrogen, fluorine, chlorine, bromine, cyano, hydroxyl, methyl, ethyl, OCH 3 CF 3 and OCF 3 ,

[0136] m is 0, 1, and 2,

[0137] n is 0, 1 and 2.

[0138] The above general or preferred radical definitions apply both to the end products of the general formula (I) and to the starting materials or intermediates required for the preparation in each case. These radical definitions can be combined with one another as desired, ie including combinations between the given preferred ranges.

[0139] Of particular interest, primarily for reasons of greater herbicidal activity, better selectivity and / or better preparability, are the compounds of the general formula (I) or their salts according to the invention or their use according to the invention in which the individual radicals have one of the preferred meanings already specified or specified below, or in particular those in which one or more of the preferred meanings already specified or specified below occur in combination.

[0140] With respect to the compounds of the invention, the terms used above and further used below will be explained. These are familiar to the skilled person and have in particular the definitions explained below:

[0141] Unless otherwise defined, the names of chemical groups are generally to be understood as meaning that the connection to the backbone or the rest of the molecule is via the last mentioned structural element of the relevant chemical group, i.e., for example in (C 2 -C 8 In the case of )-alkenyloxy, via the oxygen atom, while in the case of heterocyclyl-(C 1 -C 8 )-alkyl or R 12 O(O)C-(C 1 -C 8 )-alkyl, in each case via a carbon atom of the alkyl radical.

[0142] According to the present invention, "alkylsulfonyl" - alone or as part of a chemical group - refers to a straight-chain or branched alkylsulfonyl group, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (but not limited to) (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 sulfonyl, 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, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.

[0143] According to the invention, “heteroarylsulfonyl” is understood to mean optionally substituted pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally substituted polycyclic heteroarylsulfonyl, here in particular optionally substituted quinolylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.

[0144] According to the present invention, "alkylthio" - alone or as part of a chemical group - refers to a straight-chain or branched S-alkyl group, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (C 1 -C 10 )-、(C 1 -C 6 )-or(C 1 -C 4 )-alkylthio, such as (but not limited to) (C 1 -C 6 )-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3- methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio.

[0145] According to the invention, "cycloalkylthio" denotes a cycloalkyl group which is bonded via a sulfur atom.

[0146] According to the present invention, "alkylsulfinyl (alkyl-S(=O)-)", unless otherwise defined elsewhere, means an alkyl group bonded to the backbone via -S(=O)-, such as (C 1 -C 10 )-、(C 1 -C 6 )-or(C 1 -C 4 )-alkylsulfinyl, such as (but not limited to) (C 1 -C 6)-alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methyl Pentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.

[0147] "Alkoxy" refers to an alkyl group attached through an oxygen atom, for example (but not limited to) (C 1 -C 6 )-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy. Alkenyloxy represents an alkenyl group attached via an oxygen atom, and alkynyloxy represents an alkynyl group attached via an oxygen atom, such as (C 2 -C 10 )-、(C 2 -C 6 )-or(C 2 -C 4 )-alkenyloxy and (C 3 -C 10 )-、(C 3 -C 6 )-or(C 3-C 4 )-alkynyloxy.

[0148] "Cycloalkoxy" means a cycloalkyl group attached through an oxygen atom.

[0149] According to the present invention, "alkylcarbonyl" (alkyl-C(=O)-), unless defined differently elsewhere, represents an alkyl group bonded to the backbone via -C(=O)-, such as (C 1 -C 10 )-、(C 1 -C 6 )-or(C 1 -C 4 The number of carbon atoms here relates to the alkyl group in the alkylcarbonyl group.

[0150] "Alkoxycarbonyl (alkyl-OC(=O)-)", unless defined differently elsewhere, is an alkyl group bonded to the backbone via -OC(=O)-, such as (C 1 -C 10 )-、(C 1 -C 6 )-or(C 1 -C 4 )-alkoxycarbonyl. The number of carbon atoms here refers to the alkyl group in the alkoxycarbonyl group. Similarly, according to the present invention, "alkenyloxycarbonyl" and "alkynyloxycarbonyl", unless defined differently elsewhere, represent alkenyl and alkynyl groups bonded to the skeleton via -OC(=O)-, respectively, such as (C 2 -C 10 )-、(C 2 -C 6 )-or(C 2 -C 4 )-alkenyloxycarbonyl and (C 3 -C 10 )-、(C 3 -C 6 )-or(C 3 -C 4 The carbon number here refers to the alkenyl or alkynyl group in the alkenyloxycarbonyl or alkynyloxycarbonyl group.

[0151] According to the present invention, the term "alkylcarbonyloxy" (alkyl-C(=O)-O-), unless defined differently elsewhere, represents an alkyl group bonded to the backbone via the oxygen of the carbonyloxy group (-C(=O)-O-), such as (C 1 -C 10 )-、(C 1 -C 6 )-or(C 1 -C 4The number of carbon atoms here relates to the alkyl group in the alkylcarbonyloxy group.

[0152] The term "aryl" denotes an optionally substituted monocyclic, bicyclic or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10, ring carbon atoms, for example phenyl, naphthyl, anthracenyl, phenanthrenyl, etc., preferably phenyl.

[0153] The term "optionally substituted aryl" also includes polycyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenyl, where the bonding site is on the aromatic system. In systematic terms, the term "optionally substituted phenyl" also generally encompasses "aryl". Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkyloxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, dialkylaminoalkoxy, tri[alkyl]silyl, di[alkyl]arylsilyl, Bis[alkyl]alkylsilyl, tris[alkyl]silylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bialkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, bialkylaminocarbonyl, heteroarylalkoxy, arylalkoxy.

[0154] Heterocyclic groups (heterocyclic radicals) contain at least one saturated, unsaturated, partially saturated or heteroaromatic heterocyclic ring (= wherein at least one carbon atom has been replaced by a heteroatom, preferably a carbocyclic ring selected from N, O, S, P) and can be unsubstituted or substituted, in the case of substitution, the bonding site is located on the ring atom. If the heterocyclic radical group or heterocyclic ring is optionally substituted, it can be fused with other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclic radicals, polycyclic systems are also included, such as 8-azabicyclo [3.2.1] octyl, 8-azabicyclo [2.2.2] octyl or 1-azabicyclo [2.2.1] heptyl. Optionally substituted heterocyclic radicals also include spirocyclic systems, such as 1-oxa-5-azaspiro [2.3] hexyl. Unless defined differently, the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and in the heterocyclic ring one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms which are preferably selected from N, O and S, but no two oxygen atoms should be directly adjacent, for example to 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-pyrrol-1- or -2- or -3-yl, 2,5-dihydro-1H-pyrrol-1- or -2- or -3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3 ,4,5-tetrahydropyridine-2-or-3-or-4-or-5-yl or -6-yl; 1,2,3,6-tetrahydropyridine-1-or-2-or-3-or-4-or-5-or-6-yl; 1,2,3,4-tetrahydropyridine-1-or-2-or-3-or-4-or-5-or-6-yl; 1,4-dihydropyridine-1-or-2-or-3-or-4-yl; 2,3-dihydropyridine-2-or-3-or-4-or-5-or-6-yl; 2,5-dihydropyridine-2-or-3-or-4-or-5-or-6-yl, 1-or 2-or 3-or 4-azepanyl; 2,3,4,5-tetrahydro-1H-azepanyl -1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydro-1H-azepine -1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-1H-azepine -1- or -2- or -3- or -4-yl; 3,4,5,6-tetrahydro-2H-azepine -2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-1H-azepine -1- or -2- or -3- or -4-yl; 2,5-dihydro-1H-azepine -1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,7-dihydro-1H-azepine -1- or -2- or -3- or -4-yl; 2,3-dihydro-1H-azepine -1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 3,4-dihydro-2H-azepine -2- or -3- or -4- or -5- or -6- or -7-yl; 3,6-dihydro-2H-azepine -2- or -3- or -4- or -5- or -6- or -7-yl; 5,6-dihydro-2H-azepine -2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-3H-azepine -2- or -3- or -4- or -5- or -6- or -7-yl; 1H-azepine -1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2H-azepine -2- or -3- or -4- or -5- or -6- or -7-yl; 3H-azepine -2- or -3- or -4- or -5- or -6- or -7-yl; 4H-aza -2- or -3- or -4- or -5- or -6- or -7-yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or -3- or -4- or -5-yl; 2,5-dihydrofuran-2- or -3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2- or -3- or -4- or -5-yl; H-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-oxacycloheptanyl; 2,3,4,5-tetrahydrooxacycloheptanyl -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydrooxadenosine -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydrooxadenosine -2- or -3- or -4-yl; 2,3-dihydrooxa -2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydrooxadenosine -2- or -3- or -4-yl; 2,5-dihydrooxa -2- or -3- or -4- or -5- or -6- or -7-yl; oxa -2- or -3- or -4- or -5- or -6- or -7-yl; 2- or 3-tetrahydrothienyl; 2,3-dihydrothien-2- or -3- or -4- or -5-yl; 2,5-dihydrothien-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; 2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 4H-thiopyran-2- or -3- or -4-yl. Preferred 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridine, oxirane, thiirane, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxetane-2-yl. Further examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic groups having two heteroatoms selected from N, O and S, for example, 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1- or 2 - or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; hexahydropyridazine-1- or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl -yl; 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl; 4,5-dihydropyridazine-3- or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3- or 4-yl; 1,6-dihydropyridazine-1- or 3- or 4- or 5- or 6-yl; hexahydropyrimidin-1- or 2- or 3- or 4-yl; 1,4,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidin-1- or 2 - or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidin-2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or 6-yl; 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl;1,2,3,6-tetrahydropyrazine-1- or 2- or 3- or 5- or 6-yl; 1,2,3,4-tetrahydropyrazine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazine-1- or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazine-1- or 2- or 3-yl; 2,3-dihydropyrazine-2- or 3- or 5- or 6-yl 6-yl; 2,5-dihydropyrazine-2- or 3-yl; 1,3-dioxol-2- or 4- or 5-yl; 1,3-dioxol-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-dithiolane-3- or 4-yl; 3H-1,2-dithiolane-3- or 4- or 5-yl; 1,3-dithiolane-2- or 4-yl; 1,3-dithiolane-2- or 4-yl; 1,2-dithiane-3- or 4-yl; 3,4-dihydro-1,2-dithiane-3- or 4- or 5- or 6-yl; 3,6-dihydro-1,2-dithiane-3- or 4-yl; 1,2-dithiane-3- or 4-yl; 1,3-dithiane-2- or 4- or 5-yl; 4H-1,3-dithiane-2- or 4- or 5- or 6-yl; isoxathia oxazolidin-2-, 3-, 4- or 5-yl; 2,3-dihydroisoxazol-2-, 3-, 4- or 5-yl; 2,5-dihydroisoxazol-2-, 3-, 4- or 5-yl; 4,5-dihydroisoxazol-3-, 4- or 5-yl; 1,3-oxazolidin-2-, 3-, 4- or 5-yl; 2,3-dihydro-1,3-oxazol-2-, 3- or 4- or 5-yl 4- or 5-yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 1,2-oxazinane-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1 ,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 6H-1,2-oxazine-3- or 4- or 5- or 6-yl; 4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 1,3-oxazinane-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,3-oxazine-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl; 2H-1,3-oxazine-2- or 4- or 5- or 6-yl; 6H-1,3-oxazine-2- or 4- or 5- or 6-yl; 4H-1,3-oxazine-2- or 4- or 5- or 6-yl; morpholin-2- or 3- or 4-yl; 3,4-dihydro- Hydrogen-2H-1,4-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 4H-1,4-oxazine-2- or 3-yl; 1,2-oxazepane-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,2-oxazepine; -2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,2-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,2-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,2-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,2-oxazepine -3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,2-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,2-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,2-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,2-oxazepine -3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,2-oxazepine -3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,2-oxazepine -3- or 4- or 5- or 6- or 7-yl; 1,2-oxazepine -3- or 4- or 5- or 6- or 7-yl; 1,3-oxazepane-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,3-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,3-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,3-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,3-oxazepine -2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,3-oxazepine -2- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,3-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,3-oxazepine -2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,3-oxazepine -2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,3-oxazepine -2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,3-oxazepine -2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepine -2- or 4- or 5- or 6- or 7-yl; 1,3-oxazepine -2- or 4- or 5- or 6- or 7-yl; 1,4-oxazepane-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,4-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,4-oxazepine -2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,4-oxazepine -2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,4-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,4-oxazepine -2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-1,4-oxazepine -2- or 3- or 5- or 6- or 7-yl; 2,7-dihydro-1,4-oxazepine -2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-1,4-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,4-oxazepine -2- or 3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,4-oxazepine -2- or 3- or 5- or 6- or 7-yl; 1,4-oxazepine -2- or 3- or 5- or 6- or 7-yl; 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-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-thiazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-thiazin-2- or 4- or 5- or 6-yl; 2H-1,3-tetrahydro-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. Further examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic radicals having 3 heteroatoms selected from N, O and S, for example, 1,4,2-dioxazolidin-2- or 3- or 5-yl; 1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazepane-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-1,4,2-dioxazepane -3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-1,4,2-dioxazepine -2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-1,4,2-dioxazepine -2- or 3- or 5- or 6- or 7-yl; 5H-1,4,2-dioxazepine -3- or 5- or 6- or 7-yl; 7H-1,4,2-dioxazepine -3- or 5- or 6- or 7-yl. Examples of structures of optionally further substituted heterocycles are also listed below:

[0155]

[0156]

[0157] The heterocycles listed above are preferably replaced, for example, by hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkyloxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trialkylsilylalkynyl, nitro, amino, cyano, haloalkoxy The invention may be substituted with: alkyl, halogenated alkylthio, alkylthio, thiohydrin, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, heteroaryloxy, dialkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl and arylalkoxycarbonylalkylaminocarbonyl.

[0158] When the base structure is substituted with "one or more radicals" selected from a list of radicals (=radical) or a generally defined group of radicals, this includes in each case simultaneous substitution by a plurality of identical and / or structurally different radicals.

[0159] In the case of a partially or fully saturated nitrogen heterocycle, this may be linked to the remainder of the molecule via the carbon or via the nitrogen.

[0160] Suitable substituents for substituted heterocyclic groups are the substituents specified further below, as well as oxo and thio. Oxo groups as substituents on ring carbon atoms are, for example, carbonyl groups in heterocyclic rings. Therefore, lactones and lactams are preferably also included. Oxo groups may also occur on ring heteroatoms, which may be present in different oxidation states, for example in the case of N and S, and in this case form, for example, divalent -N(O)-, -S(O)- (also referred to as SO) and -S(O) in the heterocyclic ring. 2 -(Also referred to as SO 2 In the case of -N(O)- and -S(O)- groups, both enantiomers are included in each case.

[0161] According to the invention, the expression "heteroaryl" stands for heteroaromatic compounds, i.e. fully unsaturated aromatic heterocyclic compounds, preferably 5- to 7-membered rings with 1 to 4, preferably 1 or 2, identical or different heteroatoms (preferably O, S or N). Heteroaryl according to the invention is, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl; 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1 H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, aza yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1,3,5-triazine-2-yl, 1,2,4-triazine-3-yl, 1,2,4-triazine-5-yl, 1,2,4-triazine-6-yl, 1,2,3-triazine-4-yl, 1,2,3-triazine-5-yl, 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, oxazol- The heteroaryl groups of the invention may also be substituted by one or more identical or different groups. If two adjacent carbon atoms are part of another aromatic ring, the system is a fused heteroaromatic system, such as a benzofused or polyannelated heteroaromatic compound. 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 (e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazines; pyridopyrazines; pyridopyrimidines; pyridopyridazines; pteridines; pyrimidopyrimidines.Also exemplary of heteroaryl are 5- or 6-membered benzofused rings selected from 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophene-2-yl, 1-benzothiophene-3-yl, 1-benzothiophene-4-yl, -yl, 1-benzothiophene-5-yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazol-2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazol-7-yl, 2H-isoindol-2-yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H- Isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl, 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H-benzimidazol-7-yl, 1,3-benzooxazol-2-yl, 1,3-benzooxazol-4-yl, 1,3-benzooxazol-5-yl, 1,3-benzooxazol-6-yl, 1,3-benzoxazol-7-yl, 1,3-benzothiazol-2-yl, 1,3-Benzothiazol-4-yl, 1,3-Benzothiazol-5-yl, 1,3-Benzothiazol-6-yl, 1,3-Benzothiazol-7-yl, 1,2-Benzisoxazol-3-yl, 1,2-Benzisoxazol-4-yl, 1,2-Benzisoxazol-5-yl, 1,2-Benzisoxazol-6-yl, 1,2-Benzisoxazol-7-yl, 1,2-Benzisothiazol-3-yl, 1,2-Benzisothiazol-4-yl, 1,2-Benzisothiazol-5-yl, 1,2-Benzisothiazol-6-yl, 1,2-Benzisothiazol-7-yl.

[0162] The term "halogen" denotes, for example, fluorine, chlorine, bromine or iodine. If the term is applied to a radical, "halogen" denotes, for example, a fluorine, chlorine, bromine or iodine atom.

[0163] According to the invention, "alkyl" refers to a straight or branched open-chain saturated hydrocarbon radical, which is optionally monosubstituted or polysubstituted and in the latter case is referred to as "substituted alkyl". Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferably methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine. The prefix "bis" also includes combinations of different alkyl groups, for example methyl(ethyl) or ethyl(methyl).

[0164] "Haloalkyl", "haloalkenyl" and "haloalkynyl" refer to alkyl, alkenyl and alkynyl groups, respectively, which are partially or fully substituted with the same or different halogen atoms. For example, monohaloalkyl such as CH 2 CH 2 Cl, CH 2 CH 2 Br, CHClCH 3 , CH 2 Cl, CH 2 F; perhalogenated alkyl such as CCl 3 ,CClF 2 CFCl 2 CF 2 CClF 2 CF 2 CClFCF 3 ; Polyhaloalkyl such as CH 2 CHFCl, CF 2 CClFH、CF 2 CBrFH、CH 2 CF 3 ; The term perhaloalkyl also encompasses the term perfluoroalkyl.

[0165] "Partially fluorinated alkyl" means a straight or branched saturated hydrocarbon mono- or poly-substituted by fluorine, wherein the fluorine atom in question may be present as a substituent on one or more different carbon atoms of the straight or branched hydrocarbon chain, for example CHFCH 3 , CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F. CHFCF 2 CF 3 .

[0166] "Partially fluorinated haloalkyl" means a straight or branched saturated hydrocarbon substituted by different halogen atoms (with at least one fluorine atom), wherein any other halogen atoms optionally present are selected from fluorine, chlorine or bromine, iodine. The corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight or branched hydrocarbon chain. Partially fluorinated haloalkyl also includes complete substitution of straight or branched halogens including at least one fluorine atom.

[0167] "Haloalkoxy" is, for example, OCF 3 , OCHF 2 、OCH 2 F. OCF 2 CF 3 、OCH 2 CF 3 and OCH 2 CH 2 Cl; this applies correspondingly to haloalkenyl and other halogen-substituted groups.

[0168] The expression "(C 1 -C 4 "(C-alkyl)" is a shorthand for a straight or branched alkyl group having 1 to 4 carbon atoms, depending on the range mentioned for the carbon atoms, i.e., encompasses methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl groups. General alkyl groups with a larger specified range of carbon atoms, such as "(C-alkyl)" are also known. 1 -C 6 )-alkyl", accordingly also encompasses straight-chain or branched alkyl groups with a higher number of carbon atoms, i.e. according to this example also encompasses alkyl groups with 5 and 6 carbon atoms.

[0169] Unless otherwise specified, lower carbon skeletons are preferred, for example having 1 to 6 carbon atoms, or in the case of unsaturated groups, having 2 to 6 carbon atoms, in the case of hydrocarbon groups such as alkyl, alkenyl and alkynyl groups, included in composite groups. Alkyl groups included in composite groups such as alkoxy, haloalkyl, etc. are, for example, methyl, ethyl, n-propyl or isopropyl, n-, iso-, tert- or 2-butyl, pentyl, hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl, heptyl such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl groups are defined as possible unsaturated groups corresponding to alkyl groups, in which at least one double bond or triple bond is present. Groups with one double bond or triple bond are preferred.

[0170] In particular, the term "alkenyl" also includes straight or branched open-chain hydrocarbon groups having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, and also includes allenyl or cumulenyl groups having one or more cumulant double bonds, such as 1,2-propadienyl, 1,2-butadienyl and 1,2,3-pentatrienyl. Alkenyl represents, for example, vinyl which may be optionally substituted by further alkyl groups, such as (but not limited to) (C 2 -C 6)-alkenyl such as vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl , 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

[0171] In particular, the term "alkynyl" also includes straight or branched open-chain hydrocarbon groups having more than one triple bond, or having one or more triple bonds and one or more double bonds, such as 1,3-butatrienyl or 3-penten-1-yn-1-yl. (C 2 -C 6)-Alkynyl represents, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, , 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.

[0172] The term "cycloalkyl" refers to a carbocyclic saturated ring system preferably having 3 to 8 ring carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which optionally has further substitutions, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, dialkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, this includes ring systems with substituents, and also includes substituents with double bonds on the cycloalkyl group, such as alkylene groups such as methylene. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems are also included, for example bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantane-1-yl and adamantane-2-yl, and also include, for example, systems such as 1,1′-di(cyclopropyl)-1-yl, 1,1′-di(cyclopropyl)-2-yl. The term “(C 3 -C 7 )-cycloalkyl" is an abbreviation for cycloalkyl having 3 to 7 carbon atoms, corresponding to the specified range of carbon atoms.

[0173] In the case of substituted cycloalkyl, spirocycloaliphatic systems are also included, for example spiro[2.2]pentan-1-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-1-yl, spiro[3.3]hept-2-yl.

[0174] "Cycloalkenyl" means a carbocyclic, nonaromatic, partially unsaturated ring system having preferably 4 to 8 carbon atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, also including substituents having double bonds on the cycloalkenyl radical, for example alkylene radicals such as methylene. In the case of optionally substituted cycloalkenyl, the statements for substituted cycloalkyl apply accordingly.

[0175] The term "alkylene" also refers to (C 1 -C 10 )-alkylene forms represent radicals of straight-chain or branched open-chain hydrocarbon radicals linked via double bonds. The possible bonding sites of alkylene are naturally only those positions on the basic structure where two hydrogen atoms can be replaced by double bonds; a radical is, for example, =CH 2 , =CH-CH 3 =C(CH 3 )-CH 3 =C(CH 3 )-C 2 H 5 or =C(C 2 H 5 )-C 2 H 5 Cycloalkylene represents a carbocyclic group which is bonded via a double bond.

[0176] "Alkoxyalkyl" represents an alkoxy group bonded via an alkyl group, while "alkoxyalkoxy" represents an alkoxyalkyl group bonded via an oxygen atom, for example, but not limited to, methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propoxy.

[0177] "Alkylthioalkyl" represents an alkylthio group bonded via an alkyl group, while "alkylthioalkylthio" represents an alkylthioalkyl group bonded via an oxygen atom.

[0178] "Arylalkoxyalkyl" represents an aryloxy group bonded via an alkyl group, while "heteroaryloxyalkyl" represents a heteroaryloxy group bonded via an alkyl group.

[0179] "Haloalkoxyalkyl" represents a haloalkoxy group bonded via an alkyl group, while "haloalkylthioalkyl" represents a haloalkylthio group bonded via an alkyl group.

[0180] "Arylalkyl" represents an aryl group bonded via an alkyl group, "heteroarylalkyl" represents a heteroaryl group bonded via an alkyl group, and "heterocyclylalkyl" represents a heterocyclyl group bonded via an alkyl group.

[0181] “Cycloalkylalkyl” represents a cycloalkyl group bonded via an alkyl group, for example, but not limited to, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl.

[0182] According to the invention, "haloalkylthio" - by itself or as a component of a chemical group - represents a straight-chain or branched S-haloalkyl group, preferably having 1 to 8 or having 1 to 6 carbon atoms, such as (C 1 -C 8 )-、(C 1 -C 6 )-or(C 1 -C 4 )-haloalkylthio, such as (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.

[0183] “Halocycloalkyl” and “halocycloalkenyl” respectively denote cycloalkyl or cycloalkenyl groups which are partially or fully substituted by the same or different halogen atoms such as F, Cl and Br or by haloalkyl groups such as trifluoromethyl or difluoromethyl, for example 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclobut-1-yl, 1-trifluoromethylcycloprop-1-yl, 2-trifluoromethylcycloprop-1-yl, 1-chlorocycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl.

[0184] According to the invention, "trialkylsilyl" - by itself or as a component of a chemical group - represents a straight-chain or branched Si-alkyl group, preferably having 1 to 8 or having 1 to 6 carbon atoms, such as tri[(C 1 -C 8 )-、(C 1 -C 6 )-or(C 1 -C 4)-alkyl] silyl, for example (but not limited to) 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-dimethyleth-1-yl)silyl, tri(2,2-dimethyleth-1-yl)silyl.

[0185] If a compound can form tautomers whose structures are not formally covered by the general formula (I) by hydrogen displacement, these tautomers are still covered by the definition of the compounds of the general formula (I) according to the present invention, unless it is a specific tautomer that is under consideration. For example, many carbonyl compounds can exist in both the keto form and the enol form, both of which are covered by the definition of the compounds of the general formula (I).

[0186] Depending on the nature of the substituents and the way they are connected, the compounds of general formula (I) may be in the form of stereoisomers. Possible stereoisomers defined by their specific three-dimensional form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by general formula (I). For example, if there are one or more alkenyl groups, diastereomers (Z and E isomers) may occur. For example, if there are one or more asymmetric carbon atoms, enantiomers and diastereomers may occur. Stereoisomers can be obtained from the mixture obtained by the usual separation methods. Chromatographic separation can be carried out on an analytical scale to find enantiomeric excess or diastereomeric excess, or on a preparative scale to produce samples for biological testing. Stereoisomers can also be selectively prepared by using stereoselective reactions using optically active raw materials and / or auxiliary agents. The present invention therefore also relates to all stereoisomers included in general formula (I) but not shown in their specific stereoisomeric form, and mixtures thereof.

[0187] If the compound is obtained as a solid, it can also be purified by recrystallization or digestion. If individual compounds (I) cannot be obtained in a satisfactory manner by the routes described below, they can be prepared by derivatization of other compounds (I).

[0188] Suitable separation methods, purification methods and methods for separating the stereoisomers of the compounds of the general formula (I) are methods generally known to the person skilled in the art from analogous situations, for example by 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 usually be separated by chromatographic separation, for example on a chiral solid phase. Suitable methods for preparative quantities or on an industrial scale are methods such as crystallization, for example of the crystallization of diastereomeric salts, which can be obtained from diastereomeric mixtures using optically active acids and, if appropriate, optically active bases (if acidic groups are present).

[0189] Synthesis of substituted pyrazoles of general formula (I).

[0190]

[0191] The substituted pyrazoles of the general formula (I) of the present invention can be prepared by known methods. The synthetic routes adopted and studied start from commercially available or easily prepared amines, appropriately substituted aldehydes and commercially available chemicals such as malonic acid derivatives and nitromethane. In the following scheme, part Q of the general formula (I) 1 , Q 2 , Y, W, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , m, n and o have the definitions given above, except where illustrative but non-limiting definitions are given.

[0192] The compound of the general formula (Ia) of the present invention is synthesized by amide coupling of an acid of the general formula (II) with an amine of the general formula (III) in the presence of an amide coupling reagent (e.g., T3P, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide, N,N′-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazole chloride or 2-chloro-1-methylpyridinium iodide) (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymer-supported reagents, such as polymer-supported dicyclohexylcarbodiimide, are also suitable for this coupling reaction. The reaction is preferably carried out in a suitable solvent (e.g., dichloromethane, acetonitrile, N,N-dimethylformamide or ethyl acetate) at a temperature range of 0°C to 80°C and in the presence of a base (e.g., triethylamine, N,N-diisopropylethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene) (see Scheme 1). For T3P peptide coupling conditions, see Organic Process Research & Development 2009, 13, 900-906.

[0193]

[0194] Solution 1

[0195] The acid of general formula (II) can be synthesized by hydrolysis of a compound of general formula (IV) by methods known to those skilled in the art or analogously to methods known to those skilled in the art (Scheme 2). The hydrolysis can be carried out in the presence of a base or a Lewis acid. The base can be a hydroxide salt of an alkali metal (e.g., lithium, sodium or potassium), and the hydrolysis reaction is preferably carried out at a temperature ranging from room temperature to 120°C.

[0196]

[0197] Where R′=(C 1 -C 4 )-alkyl.

[0198] Solution 2

[0199] Compounds of general formula (IV) can be synthesized by alkylating compounds of general formula (V) with halides of general formula (VI) in the presence of a base (see Scheme 3). The base can be a carbonate of an alkali metal (e.g., lithium, sodium, potassium or cesium), and the hydrolysis reaction is preferably carried out in a suitable solvent (e.g., dichloromethane, acetonitrile, N,N-dimethylformamide or ethyl acetate) at a temperature range of room temperature to 150° C. See J. Med. Chem. 2011, 54 (16), 5820-5835 and WO 2010 / 010154.

[0200]

[0201] Where R′=(C 1 -C 4 )-alkyl.

[0202] Wherein X = halogen.

[0203] Solution 3

[0204] Scheme 4 describes the synthesis of compounds of general formula (V) by reaction of pyrazolones of general formula (VII) in the presence of a thionating agent such as phosphorus pentasulfide or Lawesson's reagent in a suitable solvent such as toluene.

[0205]

[0206] Solution 4

[0207] Scheme 5 describes the synthesis of compounds of general formula (VII) by reaction of pyrazoles of general formula (VIII) with halosuccinimides of general formula (IX) in a suitable solvent such as DMF.

[0208]

[0209] Wherein X = halogen.

[0210] Solution 5

[0211] 3-Hydroxypyrazoles (VIII) can be prepared analogously to methods known from the literature from substituted 3-azinylpropiolic acid derivatives and phenylhydrazine (Scheme 8; e.g.: Adv. Synth. Catal. 2014, 356, 3135-3147) or from substituted azinylacrylic acid derivatives and phenylhydrazine (Scheme 8; e.g.: J. Heterocyclic Chem., 49, 130 (2012)).

[0212] The compound of general formula (X) is synthesized by amide coupling of an acid of general formula (XII) with an arylhydrazine or heteroarylhydrazine of general formula (XI) in the presence of an amide coupling reagent (e.g., T3P, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide, N,N′-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride or 2-chloro-1-methylpyridinium iodide) (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymer-bound reagents, such as polymer-bound dicyclohexylcarbodiimide, are also suitable for this coupling reaction. The reaction is preferably carried out in a suitable solvent (e.g., dichloromethane, tetrahydrofuran, acetonitrile, N,N-dimethylformamide or ethyl acetate) at a temperature range of 0°C to 80°C and in the presence of a base (e.g., triethylamine, N,N-diisopropylethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene) (see Scheme 8). For T3P peptide coupling conditions, see Organic Process Research & Development 2009, 13, 900-906.

[0213] The synthesis of 3-hydroxypyrazole of general formula (VIII) is carried out by reacting a compound of general formula (X) in the presence of a copper halide such as copper (I) iodide, copper (I) bromide or an acid such as methanesulfonic acid. The reaction is preferably carried out in a suitable solvent (e.g., 1,2-dichloroethane, acetonitrile, N,N-dimethylformamide, n-propanol or ethyl acetate) at a temperature range of 0°C to 120°C. Preferably, the reaction is carried out in N,N-dimethylformamide.

[0214]

[0215] Solution 6

[0216] Alternatively, compounds of general formula (VIII) can be synthesized via amide coupling of an acid of general formula (XIV) with an aryl or heteroaryl hydrazine of general formula (XI) in the presence of an amide coupling reagent (e.g., T3P, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide, N,N′-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride or 2-chloro-1-methylpyridinium iodide). The reaction is preferably carried out in a temperature range of 0° C. to 80° C. in a suitable solvent (e.g., dichloromethane, acetonitrile, N,N-dimethylformamide or ethyl acetate) and in the presence of a base (e.g., triethylamine, N,N-diisopropylethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene) (see Scheme 7).

[0217] The 3-hydroxypyrazole of general formula (VIII) is synthesized by reacting a compound of general formula (XIII) in the presence of an iron halide such as iron (III) chloride. The reaction is preferably carried out in a suitable solvent (such as 1,2-dichloroethane, acetonitrile, N,N-dimethylformamide or ethyl acetate) at a temperature range of 0°C to 120°C.

[0218]

[0219] Solution 7

[0220] The compound of general formula (XVI) can be synthesized by N-arylation of 3-hydroxypyrazole of general formula (XVIII) with aryl halide of general formula (XVII) in the presence of copper halide such as copper (I) iodide. The reaction is preferably carried out in a suitable solvent (such as acetonitrile or N,N-dimethylformamide) and in the presence of a base (such as triethylamine or cesium carbonate) in the temperature range of 0°C to 120°C (see Scheme 8). The compound of general formula (XVIII) can be prepared by similar methods known to those skilled in the art (Chem. Med. Chem. 2015, 10, 1184-1199).

[0221] 5-iodopyrazoles of general formula (XV) are synthesized by reacting compounds of general formula (XVI) in the presence of a base (such as lithium diisopropylamide) and iodine. The reaction (Scheme 8) is preferably carried out in a suitable solvent such as diethyl ether and tetrahydrofuran at a temperature ranging from -78°C to -60°C.

[0222]

[0223] Where X = chlorine, bromine and iodine.

[0224] Wherein R = Bn (benzyl).

[0225] Solution 8

[0226] The compound of general formula (XIX) can be prepared by reacting a compound of formula (XV) with Q in a suitable solvent. 1 -M(XX), adding a suitable amount of a transition metal catalyst, in particular a palladium catalyst (e.g. palladium diacetate or bis(triphenylphosphine)palladium(II) dichloride) or a nickel catalyst (e.g. nickel(II) acetylacetonate or bis(triphenylphosphine)nickel(II) chloride), preferably at elevated temperature in an organic solvent such as 1,2-dimethoxyethane (Scheme 9). The "M" group represents, for example, Mg-X, Zn-X, Sn((C 1 -C 4 )-alkyl) 3 , Li, Cu or B(OR b )(OR c ), where R b and Rc The groups are independently, for example, hydrogen, (C 1 -C 4 )-alkyl, or, if the group R b and R c are bonded to each other, then together they are ethylene or propylene. Generally suitable are the cross-coupling methods described in RD Larsen, Organometallics in Process Chemistry 2004 Springer Verlag; I. Tsuji, Palladium Reagents and Catalysts 2004 Wiley; and M. Beller, C. Bolm, Transition Metals for Organic Synthesis 2004 VCH-Wiley. Other suitable synthesis methods are described in Chem. Rev. 2006, 106, 2651; Platinum Metals Review, 2009, 53, 183; Platinum Metals Review 2008, 52, 172; and Acc. Chem. Res. 2008, 41, 1486.

[0227] 3-Hydroxypyrazoles of general formula (VIII) can be synthesized by reacting compounds of general formula (XIX) in the presence of a Bronsted acid such as trifluoromethanesulfonic acid. The reaction is preferably carried out in a suitable solvent such as dichloromethane at a temperature ranging from 0°C to 120°C (Scheme 9).

[0228]

[0229] Wherein R = Bn (benzyl).

[0230] Solution 9

[0231] Compounds of general formula (XXII) can be prepared by alkylation of compounds of general formula (XXIII) with halides of general formula (VI) in the presence of a base by methods known to those skilled in the art or analogously to methods known to those skilled in the art (see Scheme 10). The base can be a carbonate of an alkali metal (e.g., lithium, sodium, potassium or cesium), and the reaction is preferably carried out in a suitable solvent (e.g., dichloromethane, acetonitrile, N,N-dimethylformamide or ethyl acetate) at a temperature ranging from room temperature to 150°C.

[0232] Compounds of general formula (XXI) can be prepared by diazotization or Sandmeyer reaction with compounds of general formula (XXII) using conventional organic and inorganic nitrites (such as 1,1-dimethylethyl nitrite, tert-butyl nitrite or isoamyl nitrite) in the presence of available reagents (such as a mixture of copper (I) bromide / chloride and copper (II) or iodine) (Scheme 10). The reaction is preferably carried out at room temperature and in a temperature range of 0°C to 120°C in a suitable solvent such as dichloromethane, acetonitrile, N,N-dimethylformamide or diiodomethane. Scheme 10 describes the synthesis of compounds of general formula (XXI) by reaction of pyrazoles of general formula (XXII) with halogenated succinimides of general formula (IX) in a suitable solvent such as DMF.

[0233] The compound of general formula (IV) can be prepared by reacting a compound of formula (XXI) with Q in a suitable solvent. 1 -M(XX), adding a suitable amount of a transition metal catalyst, in particular a palladium catalyst (e.g. palladium diacetate or bis(triphenylphosphine)palladium(II) dichloride) or a nickel catalyst (e.g. nickel(II) acetylacetonate or bis(triphenylphosphine)nickel(II) chloride), preferably at elevated temperature in an organic solvent such as 1,2-dimethoxyethane (Scheme 9). The "M" group represents, for example, Mg-X, Zn-X, Sn((C 1 -C 4 )-alkyl) 3 , Li, Cu or B(OR b )(OR c ), where R b and R c The groups are independently, for example, hydrogen, (C 1 -C 4 )-alkyl, or, if the group R b and R care bonded to each other, then together they are ethylene or propylene. Generally suitable are the cross-coupling methods described in RD Larsen, Organometallics in Process Chemistry 2004 Springer Verlag; I. Tsuji, Palladium Reagents and Catalysts 2004 Wiley; and M. Beller, C. Bolm, Transition Metals for Organic Synthesis 2004 VCH-Wiley. Other suitable synthesis methods are described in Chem. Rev. 2006, 106, 2651; Platinum Metals Review, 2009, 53, 183; Platinum Metals Review 2008, 52, 172; and Acc. Chem. Res. 2008, 41, 1486.

[0234]

[0235] Where R′=(C 1 -C 4 )-alkyl.

[0236] Wherein X = halogen.

[0237] Solution 10

[0238] Scheme 11 describes the synthesis of compounds of formula (XXIII) by reaction of pyrazolone of formula (XXIV) in the presence of a thionating agent (e.g. phosphorus pentasulfide or Lawesson's reagent) in a suitable solvent such as toluene. Compounds of formula (XXIV) are commercially available or can be prepared in analogy to methods known to those skilled in the art.

[0239]

[0240] Solution 11

[0241] Compounds of general formula (IV) can be prepared by reacting 3-aminopyrazoles of general formula (XXVI) with disulfides of general formula (XXV) in the presence of an organic nitrite (e.g. 1,1-dimethylethyl nitrite, tert-butyl nitrite or isoamyl nitrite) in the presence of a metal such as copper (see Scheme 12). The reaction is preferably carried out in a suitable solvent such as dichloromethane, acetonitrile, N,N-dimethylformamide or 1,2-dichloroethane at a temperature ranging from room temperature to 120°C.

[0242]

[0243] Where R′=(C1 -C 4 )-alkyl.

[0244] Wherein X = halogen.

[0245] Solution 12

[0246] Acids of general formula (XXVI) can be synthesized by methods known to those skilled in the art or analogously to methods known to those skilled in the art by reacting compounds of general formula (XXVII) in the presence of a Lewis acid such as trifluoroacetic acid (Scheme 13). The reaction is preferably carried out at a temperature ranging from room temperature to 140°C.

[0247]

[0248] Where R′=(C 1 -C 4 )-alkyl.

[0249] Solution 13

[0250] The compound of general formula (XXVII) is synthesized by Curtius reaction of an acid of general formula (XXIX) with an azide of general formula (XXVIII). The reaction is preferably carried out in a suitable solvent (e.g. tert-butyl alcohol) and in the presence of a base (e.g. triethylamine, N,N-diisopropylethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene) at a temperature range of 0°C to 100°C (see Scheme 14).

[0251]

[0252] Solution 14

[0253] Acids of general formula (XXIX) can be synthesized by hydrolysis of compounds of general formula (XXX) by methods known to those skilled in the art or analogously to methods known to those skilled in the art (Scheme 15). The hydrolysis can be carried out in the presence of a base or a Lewis acid. The base can be a hydroxide salt of an alkali metal (e.g., lithium, sodium or potassium), and the hydrolysis reaction is preferably carried out at a temperature ranging from room temperature to 120°C.

[0254]

[0255] Where R′=(C 1 -C 4 )-alkyl.

[0256] Solution 15

[0257] Scheme 16 describes the synthesis of compounds of general formula (XXX) by reaction of pyrazoles of general formula (XXXI) with halosuccinimides of general formula (IX) in a suitable solvent such as DMF.

[0258]

[0259] Wherein X = halogen.

[0260] Scheme 16

[0261] Compounds of the general formula (XXXI) are synthesized via condensation of diketoesters of the general formula (XXXIII) with arylhydrazines or heteroarylhydrazines of the general formula (XI) in the presence of a Bronsted acid (e.g. acetic acid or hydrogen chloride) in a suitable solvent (e.g. methanol, ethanol, isopropanol, n-butanol, tetrahydrofuran, dioxane, toluene or chlorobenzene) (Scheme 17). The reaction is preferably carried out at a temperature in the range of 0° C. to 150° C. Compounds of the general formula (XI) and (XXXIII) are commercially available or can be prepared analogously to methods known to those skilled in the art.

[0262]

[0263] Where R′=(C 1 -C 4 )-alkyl.

[0264] Solution 17

[0265] Compounds of general formula (XXXIV) can be prepared, for example, by reacting a compound of formula (VII) with a metal cyanide M-CN (XXXV) in a suitable solvent, adding a suitable amount of a transition metal catalyst, in particular a palladium catalyst (e.g. tetrakis(triphenylphosphine)palladium(0) or palladium diacetate or bis(triphenylphosphine)palladium(II) dichloride) or a nickel catalyst (e.g. nickel(II) acetylacetonate or bis(triphenylphosphine)nickel(II) chloride), preferably at elevated temperature in an organic solvent (e.g. 1,2-dimethoxyethane or N,N-dimethylformamide) (Scheme 18). The "M" group represents, for example, magnesium, zinc, lithium or sodium. Suitable cross-coupling methods are those described in R.D. Larsen, Organometallics in Process Chemistry 2004 Springer Verlag; I. Tsuji, Palladium Reagents and Catalysts 2004 Wiley; and M. Beller, C. Bolm, Transition Metals for Organic Synthesis 2004 VCH-Wiley. Other suitable synthesis methods are described in Chem. Rev. 2006, 106, 2651; Platinum Metals Review, 2009, 53, 183; Platinum Metals Review 2008, 52, 172; and Acc. Chem. Res. 2008, 41, 1486.

[0266]

[0267] Scheme 18

[0268] Compounds of general formula (XXXVI) and (XXXVII) can be prepared by reacting a compound of formula (IV) in the presence of an oxidizing agent such as mCPBA (3-chloroperbenzoic acid) in a suitable solvent such as dichloromethane or 1,2-dichloroethane (Scheme 19). The reaction is preferably carried out at a temperature ranging from -30°C to 100°C.

[0269]

[0270] Where R′=(C 1 -C 4 )-alkyl.

[0271] Solution 19

[0272] Scheme 20 describes the synthesis of compounds of general formula (IV) by reaction of pyrazoles of general formula (XXXVIII) with halosuccinimides of general formula (IX) in a suitable solvent such as DMF.

[0273]

[0274] Where R′=(C 1 -C 4 )-alkyl.

[0275] Solution 20

[0276] Selected detailed synthesis examples of compounds of the general formula (I) of the present invention are given below. The chemical examples described in the following sections are reported. 1 H NMR, 13 C-NMR and 19 F-NMR spectral data ( 1 H NMR is 400 MHz, and 13 C-NMR is 150 MHz, and 19 F-NMR was 375 MHz, solvent was CDCl 3 , CD 3 OD or d 6 =-DMSO, internal standard: tetramethylsilane δ=0.00 ppm) were obtained on a Bruker instrument and the signals listed have the meanings given below: br=broad; s=singlet, d=doublet, t=triplet, dd=double of doublets, ddd=double of doublets, m=multiplet, q=quartet, quint=quintet, sext=sextet, sept=septet, dq=double of quartets, dt=double of triplets. In the case of diastereomeric mixtures, the significant signals of each of the two diastereomers are reported or the characteristic signals of the major diastereomer are reported. The abbreviations used for chemical groups have, for example, the following meanings: Me=CH 3 , Et=CH 2 CH 3 , t-Hex=C(CH 3 ) 2 CH(CH 3 ) 2 , t-Bu=C(CH 3 ) 3 , n-Bu=unbranched butyl, n-Pr=unbranched propyl, i-Pr=branched propyl, c-Pr=cyclopropyl, c-Hex=cyclohexyl.

[0277] Synthesis Example:

[0278] Synthesis Example No. I-005:

[0279] Synthesis stage 1: (3Z)-4-(3,4-difluorophenyl)-4-hydroxy-2-oxobut-3-enoic acid ethyl ester

[0280]

[0281] Under nitrogen atmosphere, 1M trimethyl-N-(trimethylsilyl)silane amide (silanaminide) lithium solution (33.63ml, 33.63mmol, 1.05 equivalent) in THF was dissolved in ether (80ml) and cooled to -78°C with a dry ice bath. A solution of 1-(3,4-difluorophenyl)ethanone (5.0g, 35.02mmol, 1.0 equivalent) in ether (20ml) was added dropwise to the solution over 10 minutes. The resulting reaction mixture was stirred at -78°C for 3 hours and then at room temperature overnight. Subsequently, the suspension was cooled to 0 to 4°C with an ice bath, 1M hydrochloric acid was added thereto and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted three times with 100ml of ethyl acetate each time. The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. The desired (3Z)-4-(3,4-difluorophenyl)-4-hydroxy-2-oxobut-3-enoic acid ethyl ester product was isolated as a white solid (8.00 g, 97% of theory). 1 H-NMR (400MHz, CDCl 3 δ,ppm)15.05(bs,1H),7.87-7.77(m,2H),7.33-7.29(m,1H),7.00(s,1H),4.41(q,2H),1.42(t,3H).

[0282] Synthesis stage 2: 5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester

[0283]

[0284] By (3Z) -4- (3,4- difluorophenyl) -4- hydroxy -2- oxo but -3- enoic acid ethyl ester (2.0g, 7.81mmol, 1.0 equivalent) and (2- fluorophenyl) hydrazine hydrochloride (1: 1) (1.90g, 11.71mmol, 1.5 equivalent) suspended in 1.25M hydrogen chloride / ethanol (30ml) and heated to boiling 4 hours. The reaction mixture is neutralized with saturated sodium bicarbonate solution, and then extracted with dichloromethane three times, each 50ml. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. By column chromatography (ethyl acetate / heptane gradient) to the final purification of the obtained crude product, 5- (3,4- difluorophenyl) -1- (2- fluorophenyl) -1H- pyrazole -3- ethyl formate (3.02g, 98% of theoretical value) in the form of yellow oil is isolated. 1 H-NMR (400MHz, CDCl 3δ,ppm)7.57-7.53(m,1H),7.47-7.41(m,1H),7.29-7.25(m,1H),7.13-7.01(m,4H),6.97-6.93(m,1H),4.46(q,2H),1.43(t,3H).

[0285] Synthesis stage 3: 4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester

[0286]

[0287] Ethyl 5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazole-3-carboxylate (2.38 g, 6.87 mmol, 1.0 equiv) was dissolved in acetic acid (20 ml) and bromine (1.10 g, 6.87 mmol, 1.0 equiv) was added at room temperature. The resulting reaction mixture was stirred at room temperature for 2 hours and then more bromine (0.55 g, 3.43 mmol, 0.5 equiv) was added. The reaction was stirred at room temperature overnight and then ice water (150 ml) was added to produce a precipitate. The precipitate was dissolved in dichloromethane (100 ml) and extracted with saturated sodium thiosulfate solution. The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. Final purification of the crude product obtained by column chromatography (ethyl acetate / heptane gradient) isolates ethyl 4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazole-3-carboxylate (2.4 g, 78% of theory) in the form of a white solid. 1 H-NMR (400MHz, CDCl 3 δ,ppm)7.51-7.45(m,1H),7.44-7.39(m,1H),7.27-7.22(m,1H),7.17-6.98(m,4H),4.49(q,2H),1.44(t,3H).

[0288] Synthesis stage 4: 4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazole-3-carboxylic acid

[0289]

[0290] 4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (2.08g, 4.88mmol, 1.0 equivalent) and lithium hydroxide (350.6mg, 14.64mmol, 3.0 equivalent) were dissolved in a mixture of THF and water (18ml, THF: water = 7: 2) and heated to boiling for 6 hours. After cooling, the solution was acidified with 2M hydrochloric acid and extracted twice with ethyl acetate (50ml). The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. 4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazole-3-carboxylic acid (1.51g, 77% of theoretical value) was isolated as a white solid. 1 H-NMR (400MHz, CDCl 3 δ,ppm)7.52-7.42(m,1H),7.29-7.26(m,1H),7.48(m,1H),7.19-7.08(m,3H),7.03-7.00(m,1H).

[0291] Synthesis stage 5: tert-butyl [4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazol-3-yl]carbamate

[0292]

[0293] 4-Bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazole-3-carboxylic acid (1.02 g, 2.57 mmol, 1.0 equiv) and triethylamine (0.90 ml, 6.42 mmol, 2.5 equiv) were dissolved in tert-butyl alcohol (15 ml), and diphenylphosphorus azide (0.55 ml, 2.57 mmol, 1.0 equiv) was added at room temperature. The reaction was stirred at 60°C for 4 hours, during which gas evolution occurred. After cooling to room temperature, saturated sodium bicarbonate solution (10 ml) was added to the reaction solution, and the mixture was extracted twice with ethyl acetate (50 ml). The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. Final purification of the crude product obtained by column chromatography (ethyl acetate / heptane gradient) isolated tert-butyl [4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazol-3-yl]carbamate (625 mg, 51% of theory) in the form of a white solid. 1 H-NMR (400MHz, CDCl 3 δ,ppm)7.52-7.48(m,1H),7.38-7.32(m,1H),7.21(dt,1H),7.15-7.09(m,2H),7.05-6.97(m,2H),6.48(bs,1H),1.56(s,9H).

[0294] Synthesis stage 6: 4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazol-3-amine

[0295]

[0296] By [4- bromo-5- (3,4- difluorophenyl) -1- (2- fluorophenyl) -1H- pyrazole -3- bases] tert-butyl carbamate (625mg, 1.34mmol, 1.0 equivalent) and trifluoroacetic acid (0.21ml, 2.67mmol, 2.0 equivalent) dissolved in dichloromethane (20ml) and heated to boiling for 2 hours. After cooling, the reaction mixture was diluted with saturated sodium bicarbonate solution (10ml), and then extracted twice with DCM (50ml). Isolate 4- bromo-5- (3,4- difluorophenyl) -1- (2- fluorophenyl) -1H- pyrazole -3- amine (480mg, 99% of theoretical value) in the form of a white solid. 1 H-NMR (400MHz, CDCl 3 δ,ppm)7.96(bs,2H),7.46-7.36(m,2H),7.26-7.23(m,1H),7.18-7.10(m,3H),7.08-7.00(m,1H).

[0297] Synthesis stage 7: Ethyl {[4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazol-3-yl]sulfanyl}acetate (Example No. I-002)

[0298]

[0299] 4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazole-3-amine (223 mg, 0.61 mmol, 1.0 eq.), diethyl 2,2'-disulfanediyldiacetate (0.22 ml, 1.21 mmol, 2 eq.) and copper powder (7.70 mg, 0.12 mmol, 0.2 eq.) were suspended in 1,2-dichloroethane (10 ml) and heated to 60 ° C for 15 minutes. Subsequently, tert-butyl nitrite (0.22 ml, 1.21 mmol, 2.0 eq.) was added dropwise and the reaction mixture was heated to 80 ° C for 4 hours. After cooling, the reaction mixture was diluted with water (10 ml) and dichloromethane (30 ml), and then extracted twice with DCM (50 ml). The phases were separated using a phase separator. Final purification of the crude product obtained by column chromatography (ethyl acetate / heptane gradient) isolated ethyl {[4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazol-3-yl]sulfanyl}acetate (129 mg, 44% of theory) in the form of a white solid. 1 H-NMR (400MHz, CDCl 3 δ,ppm)7.44-7.34(m,2H),7.26-7.20(m,1H),7.13-7.02(m,3H),6.99-6.96(m,1H),4.22(q,2H),3.89(s,2H),1.24(t,3H).

[0300] Synthesis stage 8: {[4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazol-3-yl]sulfanyl}acetic acid (Example No. I-005)

[0301]

[0302] Ethyl {[4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazol-3-yl] sulfanyl}acetic acid (83 mg, 0.18 mmol, 1.0 equiv) and lithium hydroxide (12.6 mg, 0.53 mmol, 3.0 equiv) were dissolved in a mixture of THF and water (9 ml, THF: water = 7: 2) and heated to boiling for 6 hours. After cooling, the solution was acidified with 2M hydrochloric acid and extracted twice with ethyl acetate (50 ml). The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. Ethyl {[4-bromo-5-(3,4-difluorophenyl)-1-(2-fluorophenyl)-1H-pyrazol-3-yl] sulfanyl}acetic acid (56 mg, 68% of theoretical value) was isolated as a white solid. 1 H-NMR (400MHz, CDCl 3δ,ppm)7.45-7.35(m,2H),7.27-7.22(m,1H),7.18-7.09(m,3H),7.01-6.97(m,3H),3.86(s,2H).

[0303] Synthesis Example No. I-008:

[0304] Synthesis stage 1: Ethyl {[4-bromo-1-(2,3-difluorophenyl)-5-phenyl-1H-pyrazol-3-yl]sulfonyl}acetate

[0305]

[0306] Ethyl {[4-bromo-1-(2,3-difluorophenyl)-5-phenyl-1H-pyrazol-3-yl]sulfanyl}acetate (115 mg, 0.25 mmol, 1.0 equiv) was dissolved in dichloromethane (5 ml). 3-Chloroperoxybenzoic acid (114 mg, 0.51 mmol, 2.0 equiv, purity 77%) was added to the solution. The resulting reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane (30 ml) and extracted with saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. The final purification of the crude product by column chromatography (ethyl acetate / heptane gradient) isolated ethyl {[4-bromo-1-(2,3-difluorophenyl)-5-phenyl-1H-pyrazol-3-yl]sulfonyl}acetate (90 mg, 55% of theoretical value, purity 80%) in the form of a colorless solid. 1 H-NMR (400MHz, CDCl 3 δ,ppm)7.71-7.63(m,2H),7.58-7.32(m,6H),4.76(s,2H),4.12(q,2H),1.13(t,3H).

[0307] Synthesis Example No. II-001:

[0308] Synthesis stage 1: 1H-pyrazole-3-ol

[0309]

[0310] (2E)-3-methoxy methyl acrylate (20.00 g, 172.24 mmol, 1.0 equivalent) was dissolved in methanol (15 ml), and hydrazine hydrate (1: 1) (8.38 ml, 172.24 mmol, 1 equivalent) was added dropwise, and the reaction mixture was heated until boiling. Subsequently, the reaction mixture was heated to boiling for 2 hours and then concentrated under reduced pressure. The crude product was used in the next synthesis stage without further purification. 1H-pyrazole-3-ol (15.30 g, 95% of theoretical value) was isolated in the form of a yellow oil. 1 H-NMR (400MHz, CDCl 3 δ,ppm)9.85(bs,1H),7.35(d,1H),5.43(d,1H).

[0311] Synthesis stage 2: 1-(3-hydroxy-1H-pyrazol-1-yl)ethanone

[0312]

[0313] 1H-pyrazole-3-ol (15.30 g, 181.97 mmol, 1.0 equivalent) was dissolved in pyridine (100 ml). A mixture of acetic anhydride (19.00 ml, 201.37 mmol) and pyridine (10 ml) was added dropwise to the solution over 30 minutes. The resulting reaction mixture was heated to a temperature of 100° C. for 2 hours. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was stirred with ether (50 ml), during which it crystallized. 1-(3-hydroxy-1H-pyrazole-1-yl)ethanone (18.00 g, 78% of theoretical value) was isolated as a light yellow solid. 1 H-NMR (400MHz, CDCl 3 δ,ppm)10.98(bs,1H),8.12(d,1H),6.01(d,2H),2.47(s,3H).

[0314] Synthesis stage 3: 3-(Benzyloxy)-1H-pyrazole

[0315]

[0316] 1-(3-Hydroxy-1H-pyrazol-1-yl)ethanone (18.00 g, 142.73 mmol, 1.0 equiv), (bromomethyl)benzene (16.98 ml, 142.73 mmol, 1.0 equiv) and potassium carbonate (19.73 g, 142.73 mmol, 1.0 equiv) were suspended in butane-2-one (200 ml) and heated to boiling for 3 hours. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in THF (150 ml) and methanol (150 ml), and 6 M sodium hydroxide solution (24 ml) was added. The reaction mixture was stirred at room temperature for 1 hour, and then the solvent was concentrated under reduced pressure. The residue was dissolved in dichloromethane (150 ml) and washed twice with water (50 ml). The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. The crude product was used in the next synthesis stage without further purification. 3-(Benzyloxy)-1H-pyrazole (19.82 g, 75% of theory) was isolated in the form of a yellow oil. 1 H-NMR (400MHz, CDCl 3 δ,ppm)10.55(bs,1H),7.43-7.23(m,6H),5.74(d,1H),5.20(s,2H).

[0317] Synthesis stage 4: 3-(Benzyloxy)-1-(2-fluorophenyl)-1H-pyrazole

[0318]

[0319] 3-(Benzyloxy)-1H-pyrazole (2.74 g, 15.73 mmol, 1.0 eq), 1-fluoro-2-iodobenzene (1.83 ml, 15.73 mmol, 1 eq), copper (I) iodide (299 mg, 1.57 mmol, 0.10 eq), potassium carbonate (5.43 g, 39.31 mmol, 2.50 eq) and N,N'-dimethylethane-1,2-diamine (0.87 ml, 7.88 mmol, 0.10 eq) were suspended in toluene (25 ml) and heated to 115°C for 5 hours. The solvent was removed under reduced pressure and the residue was extracted with dichloromethane (50 ml) and water (20 ml). The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. Final purification of the crude product obtained by column chromatography (ethyl acetate / heptane gradient) isolated 3-(benzyloxy)-1-(2-fluorophenyl)-1H-pyrazole (2.09 g, 49% of theory, purity 80%) in the form of a yellow solid. 1 H-NMR (400MHz, CDCl 3δ,ppm)7.91-7.85(m,2H),7.51-7.49(m,2H),7.42-7.32(m,3H),7.25-7.16(m,3H),5.95(d,1H),5.32(s,2H).

[0320] Synthesis stage 5: 3-(Benzyloxy)-1-(2-fluorophenyl)-5-iodo-1H-pyrazole

[0321]

[0322] 3-(Benzyloxy)-1-(2-fluorophenyl)-1H-pyrazole (4.81 g, 17.92 mmol, 1.0 eq.) was dissolved in THF (140 ml) and cooled to -78°C using an ice bath (dry ice / acetone). A 2M solution of lithium diisopropylamide in THF was added dropwise to the cooled solution over 10 minutes, and the mixture was stirred at this temperature for a further 30 minutes. Iodine (4.55 g, 17.92 mmol, 1 eq.) dissolved in THF (10 ml) was then added dropwise over 10 minutes. Thereafter, the reaction mixture was warmed to room temperature overnight and extracted with water (300 ml) and ethyl acetate (250 ml). The organic phase was washed with saturated sodium thiosulfate solution (75 ml). Subsequently, the organic phase was dried over magnesium sulfate and the solvent removed under reduced pressure. Final purification of the crude product obtained by column chromatography (ethyl acetate / heptane gradient) isolated 3-(benzyloxy)-1-(2-fluorophenyl)-5-iodo-1H-pyrazole (5.20 g, 73% of theory) in the form of a brown oil. 1 H-NMR (400MHz, CDCl 3 δ,ppm)7.90-7.84(m,2H),7.52-7.47(m,2H),7.41-7.31(m,2H),7.25-7.15(m,3H),5.94(s,1H),5.31(s,2H).

[0323] Synthesis stage 6: 5-[3-(Benzyloxy)-1-(2-fluorophenyl)-1H-pyrazol-5-yl]-2-fluoropyridine

[0324]

[0325] 3-(Benzyloxy)-1-(2-fluorophenyl)-5-iodo-1H-pyrazole (2.20 g, 5.58 mmol, 1.0 equiv), (6-fluoropyridin-3-yl)boric acid (1.18 mg, 8.37 mmol, 1.5 equiv) and cesium carbonate (7.27 mg, 22.32 mmol, 4 equiv) were suspended in a solvent mixture consisting of toluene (56 ml), ethanol (16 ml) and water (8 ml), and degassed and inflated with argon three times in succession. To this suspension was added bis(di-tert-butyl(4-dimethylaminophenyl)phosphino)palladium(II) chloride. The reaction mixture was then heated to boiling for 2 hours. The solvent was removed under reduced pressure, and the residue was extracted with dichloromethane (750 ml) and water (30 ml). The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. Final purification of the crude product obtained by column chromatography (ethyl acetate / heptane gradient) isolated 5-[3-(benzyloxy)-1-(2-fluorophenyl)-1H-pyrazol-5-yl]-2-fluoropyridine (1.01 g, 45% of theory) in the form of a yellow solid. 1 H-NMR (400 MHz, DMSO-d 6 δ,ppm)8.15(d,1H),7.81-7.77(m,1H),7.63-7.59(m,1H),7.54-7.48( m,3H),7.43-7.30(m,5H),7.22-7.19(m,1H),6.44(s,1H),5.24(s,2H).

[0326] Synthesis stage 7: 5-[3-(Benzyloxy)-4-bromo-1-(2-fluorophenyl)-1H-pyrazol-5-yl]-2-fluoropyridine

[0327]

[0328] 5-[3-(Benzyloxy)-1-(2-fluorophenyl)-1H-pyrazol-5-yl]-2-fluoropyridine (870 mg, 1.92 mmol, 1.0 equivalent, purity 80%) was dissolved in DMF (10 ml), and 1-bromopyrrolidine-2,5-dione (0.51 g, 2.87 mmol, 1.5 equivalent) was added at room temperature. The resulting reaction mixture was stirred overnight at room temperature and then mixed with ice water (50 ml) to produce a precipitate. The precipitate was dissolved in dichloromethane (100 ml) and extracted with a saturated sodium thiosulfate solution. The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. The final purification of the resulting crude product by column chromatography (ethyl acetate / heptane gradient) isolated 5-[3-(benzyloxy)-4-bromo-1-(2-fluorophenyl)-1H-pyrazol-5-yl]-2-fluoropyridine (847 mg, 99% of theoretical value) in the form of a white solid. 1H-NMR (400 MHz, DMSO-d 6 δ,ppm)8.20(d,1H),7.96-7.91(m,1H),7.61(dt,1H),7.52-7.27(m,9H),5.33(s,2H).

[0329] Synthesis stage 8: 4-bromo-1-(2-fluorophenyl)-5-(6-fluoropyridin-3-yl)-1H-pyrazol-3-ol

[0330]

[0331] 5-[3-(Benzyloxy)-4-bromo-1-(2-fluorophenyl)-1H-pyrazol-5-yl]-2-fluoropyridine (811 mg, 1.83 mmol, 1.0 equiv) was dissolved in dichloromethane (25 ml), and trifluoromethanesulfonic acid (0.33 ml, 3.67 mmol, 2.0 equiv) was added at room temperature. The resulting reaction mixture was stirred at room temperature for 2 hours and then extracted with saturated sodium bicarbonate solution (20 ml). The aqueous phase was extracted twice with dichloromethane (25 ml). The organic phases were combined, dried over magnesium sulfate and the solvent was removed under reduced pressure. The crude product was used in the next synthesis stage without further purification. 4-bromo-1-(2-fluorophenyl)-5-(6-fluoropyridin-3-yl)-1H-pyrazole-3-ol (700 mg, 92% of theoretical value, purity 90%) was isolated as a white solid. 1 H-NMR (400MHz, CDCl 3 δ,ppm)9.51(bs,1H),8.12(d,1H),7.76(dt,1H),7.48-7.43(m,1H),7.4 1-7.38(m,1H),7.27-7.24(m,1H),7.08-7.06(m,1H),6.96-6.94(m,1H).

[0332] Synthesis stage 8: 4-bromo-1-(2-fluorophenyl)-5-(6-fluoropyridin-3-yl)-1H-pyrazole-3-thiol

[0333]

[0334] 4-Bromo-1-(2-fluorophenyl)-5-(6-fluoropyridin-3-yl)-1H-pyrazol-3-ol (930 mg, 2.64 mmol, 1.0 eq.) was suspended in toluene (20 ml) and phosphorus pentasulfide (2.35 g, 5.28 mmol, 2.0 eq.) was added at room temperature. The resulting reaction mixture was heated to boiling for 6 hours (evolving gas). After cooling to room temperature, the precipitate was filtered off and extracted with toluene (50 ml) under stirring. The toluene phases were combined and the solvent was removed under reduced pressure. The crude product was used in the next synthesis stage without further purification. 4-Bromo-1-(2-fluorophenyl)-5-(6-fluoropyridin-3-yl)-1H-pyrazole-3-thiol (515 mg, 52% of theory) was isolated as a yellow solid. 1 H-NMR (400MHz, CDCl 3 δ,ppm)

[0335] Synthesis stage 9: Ethyl {[4-bromo-1-(2-fluorophenyl)-5-(6-fluoropyridin-3-yl)-1H-pyrazol-3-yl]sulfanyl}acetate (Example No. II-001)

[0336]

[0337] 4-Bromo-1-(2-fluorophenyl)-5-(6-fluoropyridin-3-yl)-1H-pyrazole-3-thiol (515 mg, 1.40 mmol, 1.0 eq.) and sodium acetate (172 mg, 2.10 mmol, 1.5 eq.) were suspended in ethanol (10 ml), and then ethyl bromoacetate (0.17 ml, 1.54 mmol, 1.1 eq.) was added. The resulting reaction mixture was heated to boiling for 3 hours. After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was extracted with dichloromethane (50 ml) and water (10 ml), then stirred with toluene (50 ml). The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. Final purification of the crude product obtained by column chromatography (ethyl acetate / heptane gradient) resulted in the isolation of ethyl {[4-bromo-1-(2-fluorophenyl)-5-(6-fluoropyridin-3-yl)-1H-pyrazol-3-yl]sulfanyl}acetate (21 mg, 3% of theory) in the form of a white solid. 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)8.10(d,1H),7.72(dt,1H),7.48-7.42(m,1H),7.41-7.37(m,1H),7.27-7.23 (m,1H),7.07-7.03(m,1H),6.97-6.92(m,1H),4.22(q,2H),3.90(s,2H),1.25(t,3H).

[0338] Analogously to the preparation examples listed above and described at the appropriate points, and taking into account the general details relating to the preparation of substituted pyrazoles, the compounds listed below were obtained:

[0339] Table I:

[0340]

[0341]

[0342]

[0343] Table II:

[0344]

[0345]

[0346]

[0347] Table III:

[0348]

[0349] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> Y <![CDATA[Q 2 ]]> m <![CDATA[(R 9 ) o ]]> III-001 H E Br 2-F-Ph 0 H III-002 H H Br Ph 0 H III-003 H E Br Ph 0 H III-004 H E Br 2,3-DiF-Ph 0 H III-005 H H Br 2,3-DiF-Ph 0 H

[0350] Table IV:

[0351]

[0352] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> Y <![CDATA[Q 2 ]]> m <![CDATA[(R 9 ) o ]]> IV-001 H E Br 2-F-Ph 0 4-Cl

[0353] Table V:

[0354]

[0355] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> Y <![CDATA[Q 2 ]]> m <![CDATA[(R 9 ) o ]]> V-001 H E Br 2-F-Ph 0 4-Me V-002 H H Br 2-F-Ph 0 4-Me

[0356] Table VI:

[0357]

[0358] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> Y <![CDATA[Q 2 ]]> m <![CDATA[(R 9 ) o ]]> VI-001 H E Br 2-F-Ph 0 H VI-002 H H Br 2-F-Ph 0 H

[0359] Table VII:

[0360]

[0361] Example No. <![CDATA[R 1 ]]> Y <![CDATA[Q 1 ]]> <![CDATA[Q 2 ]]> m <![CDATA[R 3 ]]> <![CDATA[R 4 ]]> VII-001 H Cl 3,4-DiF-Ph 2-F-Ph 0 H <![CDATA[CH 2 WHAT 2 CH 3 ]]> VII-002 H Cl 3,4-DiF-Ph 2-F-Ph 0 Me <![CDATA[CH 2 WHAT 2 CH 3 ]]> VII-003 H Br 3,4-DiF-Ph 2-F-Ph 0 H <![CDATA[CH 2 CO 2 CH 2 CH 3 ]]> VII-004 H <![CDATA[NO 2 ]]> 3,4-DiF-Ph 2-F-Ph 0 H <![CDATA[CH 2 WHAT 2 CH 3 ]]> VII-005 H Br Ph 2-F-Ph 0 H <![CDATA[CH 2 WHAT 2 CH 3 ]]> VII-006 H Br 3-Pyridyl 2-F-Ph 0 H <![CDATA[CH 2 CH 2 CO 2 CH 3 ]]> VII-007 H Br 3-Pyridyl 2-F-Ph 0 H <![CDATA[CH 2 WHAT 2 CH 3 ]]> VII-008 H Br 3-Pyridyl 2-F-Ph 0 Me <![CDATA[CH 2 WHAT 2 CH 3 <!-- 42 --> ]]> VII-009 H Br 5-F-3-pyridyl 2-F-Ph 0 H <![CDATA[CH 2 WHAT 2 CH 3 ]]> VII-010 H Br 5-F-3-pyridyl 2-F-Ph 0 H <![CDATA[CH 2 CH 2 CO 2 CH 3 ]]> VII-011 H Br 3,4-DiF-Ph 2-F-Ph 0 Me <![CDATA[CH 2 WHAT 2 CH 3 ]]>

[0362] Table VIII:

[0363]

[0364] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> Y <![CDATA[Q 2 ]]> m <![CDATA[(R 9 ) o ]]> VIII-001 H E Br 2-F-Ph 0 2-Cl

[0365] Spectral data for selected table examples:

[0366] Selected detailed synthesis examples of compounds of general formula (I) of the present invention are exemplified below. 1 H NMR, 13 C-NMR and 19 F-NMR spectral data ( 1 H NMR is 400 MHz, and 13 C-NMR is 150 MHz, and 19 F-NMR was 375 MHz, solvent was CDCl 3 , CD 3 OD or d 6 =-DMSO, internal standard: tetramethylsilane δ=0.00 ppm) were obtained on a Bruker instrument and the signals listed have the meanings given below: br=broad; s=singlet, d=doublet, t=triplet, dd=double of doublets, ddd=double of doublets, m=multiplet, q=quartet, quint=quintet, sext=sextet, sept=septet, dq=double of quartets, dt=double of triplets. In the case of diastereomeric mixtures, the significant signals of each of the two diastereomers are reported or the characteristic signals of the major diastereomer are reported. The abbreviations used for chemical groups have, for example, the following meanings: Me=CH 3 , Et=CH 2 CH 3 , t-Hex=C(CH 3 ) 2 CH(CH 3 ) 2 , t-Bu=C(CH 3 ) 3 , n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl.

[0367] Through conventional 1 The spectral data listed below for selected tabular examples were interpreted by H NMR or evaluated via NMR peak listing.

[0368] conventional 1 H NMR interpretation

[0369] Synthesis Example No. I-001

[0370] 1 H-NMR (400MHz, CDCl 3,δ,ppm)7.42(m,2H),7.25(m,1H),7.12(m,2H),7.07(m,1H),4.20(q,2H),3.87(s,2H),1.24(t,3H).

[0371] Synthesis Example No. I-003

[0372] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)8.46(d,1H),8.27(d,1H),7.47(m,1H),7.39(m,2H),7.26(m,1H),7.05(m,1H),4.22(q,2H),3.90(s,2H),1.26(t,3H).

[0373] Synthesis Example No. I-004

[0374] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.35(m,3H),7.26(m,2H),7.12(m,3H),4.22(q,2H),3.90(s,2H),1.26(t,3H).

[0375] Synthesis Example No. I-006

[0376] 1 H-NMR (400 MHz, DMSO-d 6 ,δ,ppm)7.57(m,1H),7.45-7.28(m,7H),3.96(s,2H).

[0377] Synthesis Example No. I-007

[0378] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.44(m,2H),7.26(m,1H),7.12(m,3H),6.99(m,1H),4.40(s,2H),4.26(q,2H),1.27(t,3H).

[0379] Synthesis Example No. I-009

[0380] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)10.80(br s,1H),7.42(m,2H),7.25(m,1H),7.11(m,3H),3.87(s,2H).

[0381] Synthesis Example No. I-010

[0382] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.64(m,1H),7.47(m,4H),7.33(m,3H),4.55(q,2H),4.15(m,2H),1.16(t,3H).

[0383] Synthesis Example No. II-002

[0384] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)8.45(d,1H),8.27(d,1H),7.46(m,1H),7.42-7.36(m,2H),7.27(m,1H),7.05(m,1H),4.22(q,2H),3.90(s,2H),1.25(t,3H).

[0385] Synthesis Example No. III-002

[0386] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)9.23(s,1H),8.67(s,2H),7.40(m,3H),7.18(m,2H),3.90(s,2H).

[0387] Synthesis Example No. III-003

[0388] 1 H-NMR (400 MHz, DMSO-d 6 ,δ,ppm)9.23(s,1H),8.77(s,2H),7.43(m,3H),7.29(m,2H),4.13(q,2H),4.09(s,2H),1.16(t,3H).

[0389] Synthesis Example No. IV-001

[0390] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.44(m,2H),7.26(m,1H),7.16(m,1H),6.86(d,1H),6.81(d,1H),4.19(q,2H),3.86(s,2H),1.23(t,3H).

[0391] Synthesis Example No. V-001

[0392] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.43(m,1H),7.31(m,1H),7.29(m,1H),7.18(m,1H),7.10(s,1H),4.20(q,2H),3.87(s,2H),2.25(s,3H),1.24(t,3H).

[0393] Synthesis Example No. V-002

[0394] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.53(m,1H),7.43(m,1H),7.32(m,1H),7.21(m,1H),7.13(s,1H),3.86(s,2H),2.46(s,3H).

[0395] Synthesis Example No. II-003

[0396] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)8.50(d,1H),8.28(s,1H),7.53-7.39(m,3H),7.28(m,1H),7.09(m,1H),4.41(s,2H),4.24(m,2H),1.27(t,3H).

[0397] Synthesis Example No. II-004

[0398] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)11.09(br s,1H),8.25(s,1H),7.57-7.51(m,2H),7.46-7.42(m,1H),7.38(dd,1H),7.31-7.25(m,2H),4.07(q,2H),4.01(s,2H),1.10(t,3H).

[0399] Synthesis Example No. I-011

[0400] 1 H-NMR (400MHz, CDCl 3,δ,ppm)7.80(d,2H),7.57-7.48(m,2H),7.34-7.28(m,2H),7.05(d,2H),4.09(q,2H),3.97(s,2H),1.11(t,3H).

[0401] Synthesis Example No. II-005

[0402] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)8.50(d,1H),8.29(d,1H),7.47-7.39(m,3H),7.27(m,1H),7.10-7.05(m,1H),3.91(s,2H).

[0403] Synthesis Example No. II-006

[0404] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)11.09(br s,1H),8.29(d,1H),7.56-7.53(m,2H),7.50-7.44(m,2H),7.36-7.27(m,2H),3.96(s,2H).

[0405] Synthesis Example No. II-007

[0406] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)8.54(s,1H),8.31(s,1H),7.66(s,1H),7.49-7.36(m,2H),7.27 -7.23(m,1H),7.08-7.03(m,1H),4.21(q,2H),3.90(s,2H),1.26(t,3H).

[0407] Synthesis Example No. I-012

[0408] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.48-7.43(m,2H),7.27-7.26(m,1H),7.20-7.07(m,4H),4.21(q,2H),3.93(s,2H),1.26(t,3H).

[0409] Synthesis Example No. II-008

[0410] 1H-NMR (400MHz, CDCl 3 ,δ,ppm)8.54(s,1H),8.31(s,1H),7.66(s,1H),7.49-7.36(m,2H),7.27-7.23(m,1H),7.08-7.03(m,1H),3.92(s,2H).

[0411] Synthesis Example No. II-009

[0412] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)11.26(s,1H),8.71(m,2H),8.09(s,1H),7.66-7.59(m,1H),7.50-7.43(m, 1H),7.37-7.24(m,2H),7.08-7.03(m,1H),4.77(s,2H),3.95(q,2H),0.95(t,3H).

[0413] Synthesis Example No. II-010

[0414] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)11.26(s,1H),8.59(d,1H),8.01(d,1H),7.91(d,1H),7.61-7.56(m,1H),7.4 8-7.43(m,1H),7.32-7.24(m,2H),4.25-4.22(d,1H),4.03-3.96(m,3H),1.04(t,3H).

[0415] Synthesis Example No. I-013

[0416] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.46-7.35(m,2H),7.27-7.18(m,1H),7.17-7.02(m,2H),6.97-6.92(m,1H),4.22(q,2H),3.89(s,2H),1.24(t,3H).

[0417] Synthesis Example No. II-011

[0418] 1 H-NMR (400MHz, CDCl 3,δ,ppm)8.51(s,1H),8.28(s,1H),7.53-7.38(m,3H),7.32-7.26(m,1H),7.12-7.07(m,1H),4.40(d,2H),4.25(q,2H),1.27(t,3H).

[0419] Synthesis Example No. II-014

[0420] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.80(d,2H),7.57-7.48(m,2H),7.34-7.28(m,2H),7.05(d,2H),3.97(s,2H).

[0421] Synthesis Example No. III-004

[0422] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)9.22(s,1H),8.67(s,2H),7.25-7.22(m,3H),4.22(q,2H),3.91(s,2H),1.26(t,3H).

[0423] Synthesis Example No. I-015

[0424] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.42-7.36(m,2H),7.22(m,1H),7.16-6.95(m,4H),4.21-4.13(m,3H),1.62(d,3H),1.22(t,3H).

[0425] Synthesis Example No. VI-001

[0426] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)8.94(s,1H),8.68(m,1H),8.59(m,1H),7.55-7.46(m,2H),7.34-7.27(m,2H),4.10(q,2H),4.01(s,2H),1.12(t,3H).

[0427] Synthesis Example No. II-012

[0428] 1 H-NMR (400MHz, CDCl 3,δ,ppm)8.24(m,1H),7.60(dd,1H),7.46(dt,1H),7.37(m,1H),7.33(m, 1H),7.23(m,1H),7.05(dt,1H),4.21(q,2H),3.89(s,2H),1.25(t,3H).

[0429] Synthesis Example No. I-016

[0430] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.43(m,1H),7.25-6.95(m,3H),6.84(m,1H),4.38(s,2H),4.25(q,2H),1.27(t,3H).

[0431] Synthesis Example No. II-013

[0432] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)8.59(m,1H),8.32(m,1H),7.66(m,1H),7.53-7.44(m,2H),7.30(m,1H),7.10(m,1H),4.40(s,2H),4.25(q,2H),1.27(t,3H).

[0433] Synthesis Example No. I-019

[0434] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.25-7.22(m,2H),7.17-7.13(m,2H),7.10-7.05(m,2H),7.01-6.97(m,2H),4.22(q,2H),3.89(s,2H),1.26(t,3H).

[0435] Synthesis Example No. I-017

[0436] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)12.81(bs,1H),7.78(d,2H),7.59-7.48(m,2H),7.33-7.29(m,2H),7.07(d,2H),3.92(s,2H).

[0437] Synthesis Example No. I-020

[0438] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.25-7.23(m,2H),7.20-7.16(m,1H),7.07-6.95(m,4H),4.22(q,2H),3.89(s,2H),1.26(t,3H).

[0439] Synthesis Example No. I-021

[0440] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.41(m,1H),7.27(m,1H),7.24-7.20(m,2H),7.04-7.00(m,2H),4.20(q,2H),3.88(s,2H),1.25(t,3H).

[0441] Synthesis Example No. I-022

[0442] 1 H-NMR (400MHz, d 6 -DMSO, δ, ppm)7.71-7.12(m,7H),4.15(m,1H),1.52(d,3H).

[0443] Synthesis Example No. I-023

[0444] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.39-7.30(m,2H),7.24-7.20(m,2H),7.02-6.95(m,3H),6.79(d,1H),4.20(q,2H),3.87(s,2H),3.43(s,3H),1.25(t,3H).

[0445] Synthesis Example No. I-024

[0446] 1 H-NMR (400MHz, d 6 -DMSO, δ, ppm) 12.85 (bs, 1H), 7.75 (m, 1H), 7.64 (m, 1H), 7.58-7.45 (m, 2H), 7.37-7.28 (m, 3H), 4.02 (s, 2H).

[0447] Synthesis Example No. II-015

[0448] 1 H-NMR (400MHz, CDCl 3,δ,ppm)8.22(m,1H),7.49-7.38(m,4H),7.26(m,1H,7.05(dt,1H),4.20(q,2H),3.89(s,2H),1.24(t,3H).

[0449] Synthesis Example No. I-016

[0450] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)8.26(m,1H),7.60(dd,1H),7.45-7.40(m,2H),7.35(d,1H),7.26(m,1H),7.10(m,1H),3.89(s,2H).

[0451] Synthesis Example No. I-025

[0452] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.38(m,1H),7.31-7.21(m,3H),6.90(m,1H),6.80(m,1H),4.20(q,2H),3.88(s,2H),1.24(t,3H).

[0453] Synthesis Example No. I-026

[0454] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.42(m,1H),7.32-7.26(m,2H),7.15-7.08(m,2H9,6.96-6.93(m,1H),4.19(q,2H),3.87(s,2H),1.24(t,3H).

[0455] Synthesis Example No. I-027

[0456] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.39(m,1H),7.17-7.08(m,2H),6.98-6.93(m,2H),6.81(m,1H),4.20(q,2H),3.88(s,2H),1.25(t,3H).

[0457] Synthesis Example No. VII-001

[0458] 1 H-NMR (400MHz, CDCl 3,δ,ppm)7.55(bs,1H),7.47-7.39(m,2H),7.25(m,1H),7.17-7.06(m,3H),6.99(m,1H),4.05(d,2H),3.81(s,2H),3.71(s,3H).

[0459] Synthesis Example No. I-014

[0460] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.46-7.39(m,2H),7.25(m,1H),7.14-7.10(m,3H),6.97(m,1H),3.86(s,2H).

[0461] Synthesis Example No. VII-002

[0462] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.47-7.36(m,2H),7.25(m,1H),7.15-7.04(m,3H),6.97(m,1H),4.16(s,2H),4,10(s,2H),3.73(s,3H),3.18(s,3H).

[0463] Synthesis Example No. VIII-001

[0464] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.53-7.42(m,2H),7.28(m,1H),6.85(d,1H),4.20(q,2H),3.80(s,2H),1.25(t,3H).

[0465] Synthesis Example No. VII-003

[0466] 1 H-NMR (400MHz, CDCl 3 ,δ,ppm)7.52(bt,1H),7.47-7.36(m,2H),7.23(m,1H),7.18-7.04(m,3H),7.00(m,1H),4.17(q,2H),4.03(d,2H),3.82(s,2H),1.25(t,3H).

[0467] Synthesis Example No. VII-004

[0468] 1H-NMR (400MHz, CDCl 3 ,δ,ppm)7.47-7.41(m,2H),7.25-7.02(m,6H),4.05(d,2H),3.89(s,2H),3.72(s,3H).

[0469] NMR peak list method

[0470] The 1H NMR data of the selected examples are recorded in the form of 1H NMR peak lists. For each signal peak, the δ value in ppm is first listed, and then the signal intensity is listed in parentheses. The δ value / signal intensity number pairs of different signal peaks are listed separated by semicolons.

[0471] Thus, the peak list for the examples takes the following form:

[0472] δ 1 (strength 1 );δ 2 (strength 2 );……;δ i (strength i );……;δ n (strength n )

[0473] The intensity of the sharp signal is highly correlated with the signal in cm in the printed example of the NMR spectrum and shows the true ratio of the signal intensities. In the case of broad peak signals, several peaks or middle parts of the signal can be shown and their relative intensities compared to the strongest signal in the spectrum.

[0474] To calibrate the chemical shift of the 1H NMR spectra, we use the chemical shift of tetramethylsilane and / or the solvent, particularly in the case of spectra measured in DMSO. Therefore, in the NMR peak list, the tetramethylsilane peak may appear but does not necessarily appear.

[0475] The listing of 1H NMR peaks is similar to a conventional 1H NMR printout and therefore generally includes all peaks listed in a conventional NMR interpretation.

[0476] In addition, like conventional 1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compound (which likewise form part of the subject matter of the present invention) and / or impurity peaks.

[0477] When reporting signals for compounds within the delta range of solvent and / or water, our 1H NMR peak lists show common solvent peaks, such as DMSO-D 6 The DMSO peak and the water peak in the sample generally have high intensities on average.

[0478] Peaks of stereoisomers of a target compound and / or peaks of impurities typically have lower intensities on average compared to peaks of the target compound (eg, having a purity of >90%).

[0479] Such stereoisomers and / or impurities may be unique to a particular preparation method. Therefore, their peaks can help to refer to the "byproduct fingerprint" to identify the reproducibility of our preparation method.

[0480] If necessary, the expert who calculates the peaks of the target compound by known methods (MestreC, ACD simulation and predicted values ​​with empirical evaluation) can optionally use additional intensity filters to separate the peaks of the target compound. This separation is similar to picking relevant peaks in conventional 1H NMR interpretation.

[0481] More details of the 1H NMR peak list can be found in Research Disclosure Database No. 564025.

[0482]

[0483]

[0484]

[0485] The present invention also provides one or more compounds of the general formula (I) as defined above (preferably in one of the embodiments identified as preferred or particularly preferred) and / or their salts, in particular one or more compounds of formula (I.001) to (VII.002) and / or their salts, in each case as defined above, for use as herbicides and / or plant growth regulators, preferably in crops of useful plants and / or ornamental plants.

[0486] The present invention also provides a method for controlling harmful plants and / or regulating plant growth, characterized in that an effective amount of

[0487] - one or more compounds of the general formula (I) as defined above (preferably in one of the embodiments identified as preferred or particularly preferred) and / or their salts, in particular one or more compounds of the formulae (I.001) to (VII.002), in each case as defined above, and / or their salts, or

[0488] - A composition according to the invention as defined below.

[0489] The invention also provides a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) as defined above (preferably in one of the embodiments identified as preferred or particularly preferred) and / or their salts, in particular one or more compounds of the formula (I.001) to (VII.002) and / or their salts, in each case as defined above, or

[0490] - A composition according to the invention as defined below.

[0491] The invention further provides a method for regulating the growth of plants, preferably useful plants, characterized in that an effective amount of a phytonutrient solution is applied to the plants, the seeds of the plants (i.e. plant seeds, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the plants grow (e.g. soil of crop land or non-crop land) or the cultivated area (i.e. the area on which the plants are to grow)

[0492] - one or more compounds of the general formula (I) as defined above (preferably in one of the embodiments identified as preferred or particularly preferred) and / or their salts, in particular one or more compounds of the general formulae (I.001) to (VII.002), in each case as defined above, and / or their salts, or

[0493] - A composition according to the invention as defined below.

[0494] In this context, the compounds according to the invention or the compositions according to the invention can be applied, for example, by the pre-sowing (if appropriate also by incorporation into the soil), pre-emergence and / or post-emergence method. Specific examples of some representative monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds according to the invention are listed below, but the enumeration is not intended to be limited to specific species.

[0495] In the method for controlling harmful plants or regulating plant growth of the present invention, one or more compounds of general formula (I) and / or their salts are preferably used to control harmful plants or to regulate the growth of crops of useful plants or ornamental plants, wherein the useful plants or ornamental plants are preferably transgenic plants.

[0496] The compounds of the general formula (I) and / or their salts according to the present invention are suitable for controlling monocotyledonous and dicotyledonous harmful plants of the following genera:

[0497] Monocotyledonous harmful plants of the following genera: Aegilops, Icegrass, Bentgrass, Alopecurus, Pseudobengtrich, Avena, Brachiaria, Bromus, Terrestris, Commelina, Cyperus, Cyperus, Digitaria, Echinochloa, Water Chestnut, Millet, Teff, Panicum, Festuca, Fluttergrass, Heterospermum, Imperata, Duckbill, Leptochloa, Ryegrass, Rainforest, Panicum, Paspalum, Phalaris, Timothy, Poa, Cyperus, Sagittaria, Scrub, Setaria, and Sorghum.

[0498] Dicotyledonous harmful plants of the following genera: Abutilon, Amaranth, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Shepherd's Purse, Cardamom, Cassia, Cornflower, Lemon, Thistle, Convolvulus, Datura, Desmodium, Rumex, Sugarcane, Euphorbia, Mustela, Cyperus, Lagerstroemia, Hibiscus, Ipomoea, Chenopodium, Sesame, Nymphoides, Motherwort, Matricaria, Mentha, Indigo, Corn Grass, Forget-me-not, Poppy, Morning Glory, Plantago, Polygonum, Portulaca, Ranunculus, Radish, Shepherd's purse, Knotweed, Rumex, Salsola, Senecio, Sesbania, Rhizoma Coptidis, Brassica, Solanum, Sonchus, Cuneata, Chickweed, Taraxacum, Epstein, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0499] When the compounds of the present invention are applied to the soil surface before the emergence of harmful plants (grass weeds and / or broadleaf weeds) (pre-emergence method), the emergence of seedlings of grass weeds or broadleaf weeds is either completely prevented, or they continue to grow until they reach the cotyledon stage, but then stop growing and eventually die completely after the lapse of three to four weeks.

[0500] If the active ingredients are applied to the green parts of the plants after emergence, growth stops after the treatment and the harmful plants remain at the growth stage at the time of application or die completely after a certain time, so that in this way competition from weeds that are harmful to the crop plants is eliminated very early and in a permanent manner.

[0501] Although the compounds according to the invention show excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, such as dicotyledonous crops of the genera Arachis, Beta vulgaris, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine max, Cotton, Ipomoea, Lactuca, Flax, Tomato, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Bromeliaceae, Asparagus, Avena, Hordeum, Oryza, Millet, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea mays, are only slightly damaged or not damaged at all, depending on the structure of the corresponding compounds according to the invention and the amount of application. For these reasons, the compounds according to the invention are very suitable for selectively controlling the growth of unwanted plants in plant crops, such as agriculturally useful plants or ornamental plants.

[0502] In addition, the compounds according to the invention (depending on their specific structure and the applied rate) have outstanding growth regulating properties in crop plants. They intervene in the metabolism of the plant itself by means of regulatory effects and can therefore be used to influence plant components in a controlled manner and to promote the harvest, for example by inducing drought and dwarfing growth. In addition, they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plant in the process. The inhibition of vegetative growth plays an important role for many monocotyledonous and dicotyledonous crops, since, for example, this can reduce or completely prevent lodging.

[0503] Because of their weed control and plant growth regulating properties, active ingredients can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. Usually, transgenic plants are characterized by specific favorable properties, such as resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate to, for example, the quantity, quality, storability, composition and specific components of the harvested products. For example, transgenic plants with increased starch content or changed starch quality, or those with different fatty acid compositions in the harvested products.

[0504] As regards transgenic crops, preference is given to using the compounds according to the invention and / or their salts in economically important transgenic crops of useful and ornamental plants, for example crops of cereals such as wheat, barley, rye, oats, millet, rice and maize or else of beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.

[0505] Preference is also given to employing the compounds according to the invention as herbicides in crops of useful plants which are resistant or have been rendered resistant to the phytotoxic effects of herbicides by recombinant means.

[0506] Active ingredients can also be used to control harmful plants in crops of known or still undeveloped genetically modified plants due to their weed control and plant growth regulating properties. Usually, transgenic plants are characterized by specific favorable properties, such as resistance to certain pesticides, particularly certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific features relate to, for example, the quantity, quality, storability, composition and specific components of the harvested products. For example, transgenic plants with known starch content increases or starch quality changes, or those with different fatty acid compositions in the harvested products. Other special properties may be tolerance or resistance to abiotic stressors, such as heat, cold, drought, salinity and ultraviolet radiation.

[0507] The compounds of the general formula (I) according to the invention or their salts are preferably used in economically important transgenic crops of useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and corn, or crops of sugar beet, cotton, soybean, rape, potato, tomato, pea and other vegetables.

[0508] Preference is given to employing the compounds of the formula (I) as herbicides in crops of useful plants which are resistant or have been rendered resistant to the phytotoxic effects of herbicides by recombinant means.

[0509] Conventional methods for producing novel plants with modified properties compared to existing plants consist, for example, of conventional cultivation methods and the generation of mutants. Alternatively, novel plants with modified properties can be produced with the aid of recombinant methods.

[0510] A large number of molecular biological techniques are known to those skilled in the art, by which novel transgenic plants with improved properties can be produced. For such genetic manipulations, nucleic acid molecules that allow mutagenesis or sequence changes to be carried out by the recombination of the DNA sequence can be introduced into the plasmid. With standard methods, for example, base exchange, removal of partial sequences or addition of natural or synthetic sequences can be carried out. In order to connect the DNA fragments to each other, joints or connexons can be added to the fragments.

[0511] For example, plant cells in which the activity of a gene product is reduced can be generated by expressing at least one corresponding antisense RNA, a sense RNA for achieving co-suppression, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the gene product.

[0512] For this purpose, DNA molecules covering the entire coding sequence of the gene product (including any flanking sequences that may be present) can be used, as well as DNA molecules covering only parts of the coding sequence (wherein these parts must be long enough to have an antisense effect in the cell). DNA sequences that are highly homologous to the coding sequence of the gene product, but not identical thereto, can also be used.

[0513] When expressing nucleic acid molecules in plants, the synthesized protein can be located in any desired compartment of the plant cell. However, in order to achieve localization in a specific compartment, the coding region can be, for example, connected to a DNA sequence that will ensure localization in a specific compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). Nucleic acid molecules can also be expressed in organelles of plant cells.

[0514] The transgenic plant cells can be regenerated by known techniques to give rise to complete plants. In principle, the transgenic plants can be plants of any desired plant species, ie both monocotyledons and dicotyledons.

[0515] In this way, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or by expression of heterologous (=foreign) genes or gene sequences.

[0516] The compounds (I) according to the invention are preferably used in transgenic crops which are resistant to growth regulator herbicides such as dicamba or to herbicides which inhibit essential plant enzymes such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD) or to herbicides from the class of sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and similar active ingredients.

[0517] When the active ingredients of the invention are used in transgenic crops, not only the effects on harmful plants observed in other crops occur, but also often application-specific effects occur in specific transgenic crops, such as changing or clearly broadening the range of weeds that can be controlled, changing the application rates that can be used, preferably combining well with herbicides to which the transgenic crops are resistant, and influencing the growth and yield of transgenic crop plants.

[0518] The present invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or their salts as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crop plants.

[0519] Preference is given to using the pre-emergence or post-emergence method in cereals, here preferably maize, wheat, barley, rye, oats, millet or rice.

[0520] It is also preferred to use in soybeans by the pre-emergence or post-emergence method.

[0521] The use according to the invention for controlling harmful plants or for regulating plant growth also includes the case in which the active ingredients of the general formula (I) or their salts are not formed from precursor substances ("prodrugs") until after application on, in or in the soil.

[0522] The present invention also provides the use of one or more compounds of the general formula (I) or their salts or the compositions of the present invention (as defined below) (in a method) for controlling harmful plants or for regulating plant growth, which comprises applying an effective amount of one or more compounds of the general formula (I) or their salts to plants (harmful plants, optionally together with useful plants), plant seeds, soil or cultivated areas in which or on which plants grow.

[0523] The present invention also provides a weed control and / or plant growth regulating composition, characterized in that the composition comprises

[0524] (a) one or more compounds of the general formula (I) as defined above (preferably in one of the embodiments identified as preferred or particularly preferred) and / or their salts, in particular one or more compounds of the formulae (I.001) to (VII.002), in each case as defined above, and / or their salts,

[0525] and

[0526] (b) one or more other substances selected from group (i) and / or (ii):

[0527] (i) one or more other agrochemically active substances, preferably selected from insecticides, acaricides, nematicides, other herbicides (i.e. those not meeting the definition of general formula (I) above), fungicides, safeners, fertilizers and / or other growth regulators,

[0528] (ii) one or more formulation auxiliaries customary in crop protection.

[0529] The other agrochemically active substances of component (i) of the composition of the present invention are preferably selected from the substance groups mentioned in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0530] The herbicidal or plant growth regulating compositions according to the invention preferably comprise one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers which are solid at 25° C. and 1013 mbar (preferably adsorptive particulate inert materials), wetting agents, antioxidants, stabilizers, buffer substances, defoamers, water, organic solvents (preferably organic solvents which are miscible with water in any ratio at 25° C. and 1013 mbar).

[0531] The compounds of the general formula (I) of the present invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in customary formulations. The present invention therefore also provides herbicidal and plant growth regulating compositions comprising the compounds of the general formula (I) and / or their salts.

[0532] The compounds of general formula (I) and / or their salts can be formulated in various ways, depending on the desired biological and / or physicochemical parameters. Possible formulations include, for example, wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for broadcasting and soil application, granules in microgranular form (GR), spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV preparations, microcapsules and waxes.

[0533] These individual formulation types and formulation aids, such as inert materials, surfactants, solvents and other additives, are known to those skilled in the art and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd edition, Darland Books, Caldwell NJ, HvOlphen, "Introduction to Clay Colloid Chemistry", 2nd edition, J. Wiley & Sons, NY, C. Marsden, "Solvents Guide", 2nd edition, Interscience, NY 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ, Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964, " "[Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th Edition, 1986.

[0534] Wettable powders are preparations which are uniformly dispersible in water and which contain, in addition to the active ingredient, ionic and / or nonionic surfactants (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate, in addition to diluents or inert substances. To produce wettable powders, the active herbicidal ingredients are ground, for example in customary apparatus such as hammer mills, blower mills and jet mills, and simultaneously or subsequently mixed with formulation auxiliaries.

[0535] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent (e.g. butanol, cyclohexanone, dimethylformamide, xylene or a relatively high-boiling aromatic hydrocarbon or hydrocarbon or a mixture of organic solvents) and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are calcium salts of alkylarylsulfonic acids (e.g. calcium dodecylbenzenesulfonate), or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.

[0536] Dust products are obtained by grinding the active ingredient with finely divided solids, for example talc, natural clays (eg kaolin, bentonite and pyrophyllite) or diatomaceous earth.

[0537] Suspension concentrates can be water-based or oil-based. They can be produced, for example, by wet grinding with the aid of a commercial bead mill and optionally adding surfactants as have been listed above, for example, for other formulation types.

[0538] Emulsions, such as oil-in-water emulsions (EW), can be produced, for example, with the aid of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants as have been listed above, for example, for other formulation types.

[0539] Granules can be prepared by spraying the active ingredient onto a granular inert material capable of adsorption or by applying an active ingredient concentrate to the surface of a carrier material (such as sand, kaolin or granular inert material) with the aid of a binder (e.g. polyvinyl alcohol, sodium polyacrylate or mineral oil). Suitable active ingredients can also be granulated in the customary manner for the production of fertilizer granules - if desired as a mixture with fertilizers.

[0540] Water-dispersible granules are generally produced without solid inert material by customary methods such as spray drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion.

[0541] For the production of pan granules, fluidized bed granules, extruder granules and spray granules, see, for example, the processes in "Spray-Drying Handbook", 3rd edition, 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pp. 147 ff.; "Perry's Chemical Engineer's Handbook", 5th edition, McGraw-Hill, New York 1973, pp. 8-57.

[0542] For more details on the formulation of crop protection compositions, see, for example, GC Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th edition, Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

[0543] The agrochemical preparations of the present invention, preferably herbicidal or plant growth regulating compositions, preferably contain the active ingredients of the general formula (I) and their salts in a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, and particularly preferably 2 to 80% by weight.

[0544] In wettable powders, the active ingredient concentration is, for example, about 10% to 90% by weight, and the remainder to 100% by weight is composed of conventional formulation ingredients. In emulsifiable concentrates, the active ingredient concentration may be about 1% to 90% by weight, and preferably 5% to 80% by weight. The formulation in the form of a powder contains 1% to 30% by weight of the active ingredient, preferably usually 5% to 20% by weight of the active ingredient; the sprayable solution contains about 0.05% to 80% by weight, preferably 2% to 50% by weight of the active ingredient. In the case of water-dispersible granules, the active ingredient content depends in part on whether the active compound is present in liquid or solid form and the granulation aids, fillers, etc. used. In water-dispersible granules, the content of the active ingredient is, for example, between 1% to 95% by weight, preferably between 10% to 80% by weight.

[0545] In addition, the active ingredient preparation mentioned optionally comprises corresponding customary binders (stickers), wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents that influence pH and viscosity. Examples of formulation auxiliaries are particularly described in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998).

[0546] The compound of general formula (I) or its salt can be used as is or in the form of its preparation (formulation) in combination with other pesticide active substances such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators, for example in the form of finished formulations or tank mixes. Combination formulations can be produced on the basis of the above formulations taking into account the physical properties and stability of the active ingredients to be combined.

[0547] Combination partners for the compounds of the general formula (I) according to the invention which can be used in mixed formulations or tank mixes are, for example, based on known active ingredients that inhibit, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.

[0548] Of particular interest is the selective control of harmful plants in crops of useful plants and ornamental plants. Although the compounds of the general formula (I) of the present invention have shown very good to sufficient selectivity in many crops, in principle, in some crops, and particularly in the case of a mixture with other less selective herbicides, phytotoxicity to crop plants may occur. In this regard, the combination of the compound (I) of the present invention of particular interest is those comprising the compound of the general formula (I) or its combination with other herbicides or pesticides and safeners. The safener used in the detoxification effective amount reduces the phytotoxic side effects of the herbicides / pesticides used, for example in economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), beets, sugarcane, rapeseed, cotton and soybeans, preferably cereals.

[0549] The weight ratio of herbicide (mixture) to safener generally depends on the herbicide application rate and the efficacy of the safener under consideration and can vary within wide limits, for example in the range of 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. Similar to the compounds of general formula (I) or mixtures thereof, the safener can be formulated with other herbicides / pesticides and used with the herbicide as a finished formulation or tank mix.

[0550] For application, the commercially available herbicide preparations or herbicide-safener preparations are diluted, if necessary, in the customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of powders, granules for soil application or granules for spreading and sprayable solutions are usually not diluted further with other inert substances before application.

[0551] The application amount of the compound of general formula (I) and / or its salt is affected by external conditions such as temperature, humidity, etc. to a certain extent. The application amount can change within a wide range. For the application of the herbicide as a harmful plant control, the total amount of the compound of general formula (I) and its salt 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, and particularly preferably in the range of 0.05 to 1 kg / ha. This is applicable to both the application before emergence and the application after emergence.

[0552] When the compounds of the general formula (I) and / or their salts are used as plant growth regulators, for example as stalk stabilizers for crop plants (such as those mentioned above, preferably cereals such as wheat, barley, rye, triticale, millet, rice or corn), the total application rate is preferably in the range of 0.001 to 2 kg / ha, preferably in the range of 0.005 to 1 kg / ha, in particular in the range of 10 to 500 g / ha, very particularly preferably in the range of 20 to 250 g / ha. This applies both to pre-emergence applications and to post-emergence applications.

[0553] Application as a stalk stabilizer can be carried out at various stages of plant growth. For example, it is preferably applied after the tillering stage and at the beginning of longitudinal growth.

[0554] As an alternative, it can also be applied as a plant growth regulator by treating the seeds, which includes various techniques of seed dressing and seed coating. The application rate depends on the specific technique and can be determined in preliminary trials.

[0555] Combination partners of the compounds of the general formula (I) according to the invention that can be used as compositions according to the invention (e.g., mixed formulations or tank mixes) are, for example, known active ingredients based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein. Known herbicides or plant growth regulators that can be combined with the compounds according to the invention are, for example, the following, where the active ingredients are referred to by their "common name" or by chemical name or by code number according to the International Organization for Standardization (ISO). They always encompass all use forms, for example acids, salts, esters and all isomeric forms such as stereoisomers and optical isomers, even if these are not explicitly mentioned.

[0556] Examples of such herbicidal mixtures are:

[0557] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyrrolidone pyrimidine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, beflubutamide enazolin), benazolin-ethyl, benfluralin, benfuresate, bensulfuron, (bensulfuron-methyl), bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bifenox bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, bromoxynil-potassium, bromoxynil-heptanoate and bromoxynil-octanoate, busoxinone, butachlor,Butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sod ium), chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cyproconazole ( cinmethylin), cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloprop (cycloate), cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-d-dimethylammonium, 2,4-D-diolamine, 2,4-D-ethyl, 2,4-D-2-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropylammonium, 2,4-D-potassium,2,4-D-triisopropanol ammonium and 2,4-D-triethanolamine (2,4-d-trolamine), 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl ester, 2,4-DB-potassium and 2,4-DB-sodium, daimuron, dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2 -oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr sodium -sodium), dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, diinitramine, dinoterb, diphenamid, diquat, diquat-dibromide, dithiopyr, diquat- diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600,F-5231 is N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide, F-7967 is 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenqui notrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-p, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone sodium carbazone-sodium), flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyrate l), flurenol-dimethylammonium and flurenol-methyl, fluoroglycofen (fluoroglycofen-ethyl), flupropanate, flupyrsulfuron (flupyrsulfuron-methyl-sodium), fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl,Flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium , glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium and glyphosate-trimesium, H-9201, i.e. O-(2,4-dimethyl- 6-nitrophenyl)-O-ethylisopropylphosphoramidothioate (O-2,4-dimethyl-6-nitrophenyl)-O-ethylisopropylphosphoramidothioate), halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl )、haloxyfop-P-ethoxyethyl、haloxyfop-methyl、haloxyfop-P-methyl、hexazinone、HW-02 1-(dimethoxyphosphoryl)ethyl(2,4-dichlorophenoxy)acetate、imazamethabenz、imazamethabenz-methyl、imazamox、imazamox-ammonium、imazapic、Imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, methyl iodosulfuron iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, ioxynil-potassium and ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, 3-({[5-(difluoromethyl)-1-methyl 1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2-ethylhexyl, MCPA-isopropylammonium, MCPA-potassium and MCPA-sodium, MCPB, MCPB-methyl, MCPB-ethyl, MCPB-sodium, 2-methyl-4-chloropropionic acid (mecoprop), 2-methyl-4-chloropropionic acid sodium (mecop rop-sodium) and mecoprop-butotyl, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl and mecoprop-P-potassium, mefenacet,mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, metiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor , metosulam, metoxuron, metribuzin, metsulfuron (metsulfuron-methyl), molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950 (N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide), NGGC-011, napropamide, NC-310 (4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole), neburon, nicosulfuron, nonanoic acid, pelargonic acid (pelargonic acid acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, mineral oil, phenmedipham, picloram, picolinafen, pinoxaden,Piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, pr opoxycarbazone), propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron on), pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, 3-phenyl-4-hydroxy-6-chloropyridazine (pyridafol), pyridate, pyriftalid, pyriminobac, pyriminobacil (methyl) c-methyl), pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbacil terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, thifensulfuron-methyl opramezone), tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin,trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, ureasulfate, vernolate, XDE-848, ZJ-0862 (3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:

[0558]

[0559] Examples of plant growth regulators as possible admixture partners are:

[0560] acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride), cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, endothal-disodium and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid acid), inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, methyl jasmonate, maleic hydrazide, mepiquat chloride), 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthylacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0561] Combination partners useful for the compounds of the general formula (I) according to the invention also include, for example, the following safeners:

[0562] S1) Compounds from the group of heterocyclic carboxylic acid derivatives:

[0563] S1 a )Dichlorophenylpyrazoline-3-carboxylic acid type (S1 a ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (S1-1) ("pyrazoline-butyl") and related compounds as described in WO-A-91 / 07874;

[0564] S1 b )Dichlorophenylpyrazolecarboxylic acid derivatives (S1 b ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid ethyl ester (S1-2), 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylic acid ethyl ester (S1-3), 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylic acid ethyl ester (S1-4) and related compounds as described in EP-A-333131 and EP-A-269806;

[0565] 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)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds as described, for example, in EP-A-268554;

[0566] S1 d )Triazole carboxylic acid type compound (S1 d ), preferably compounds such as fenthiocarbamide (-ethyl ester), i.e. 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylic acid ethyl ester (S1-7) and related compounds as described in EP-A-174562 and EP-A-346620;

[0567] S1 e )5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type compounds (S1 e), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds as described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) ("isoxazoline") or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13), as described in patent application WO-A-95 / 07897.

[0568] S2) Compounds from the group of 8-quinolinyloxy derivatives (S2):

[0569] S2 a )8-quinolinyloxyacetic acid type compound (S2 a ), preferably (5-chloro-8-quinolinyloxy)acetic acid 1-methylhexyl ester ("quinoline-mexyl") (S2-1), (1,3-dimethylbutan-1-yl)(5-chloro-8-quinolinyloxy)acetate (S2-2), (5-chloro-8-quinolinyloxy)acetic acid 4-allyloxybutyl ester (S2-3), 1-allyloxyprop-2-yl(5-chloro-8-quinolinyloxy)acetate (S2-4), (5-chloro-8-quinolinyloxy)acetic acid ethyl ester (S2-5) , methyl (5-chloro-8-quinolinyloxy)acetate (S2-6), allyl (5-chloro-8-quinolinyloxy)acetate (S2-7), 2-(2-propyleneiminooxy)-1-ethyl (5-chloro-8-quinolinyloxy)acetate (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolinyloxy)acetate (S2-9) and related compounds as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366, and (5-chloro-8-quinolinyloxy)acetic acid (S2-10), hydrates and salts thereof, for example lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts thereof, as described in WO-A-2002 / 34048;

[0570] S2 b (5-chloro-8-quinolinyloxy)malonic acid type compound (S2 b ), preferably compounds such as diethyl (5-chloro-8-quinolyloxy)malonate, diallyl (5-chloro-8-quinolyloxy)malonate, methylethyl (5-chloro-8-quinolyloxy)malonate and related compounds as described in EP-A-0 582 198.

[0571] S3) Active ingredients of the dichloroacetamide type (S3), which are usually used as pre-emergence safeners (safeners acting on the soil), for example "dichloropropenamide" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" from Stauffer (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2), "R-28725" from Stauffer (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (S3-3), "benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), Industries' "PPG-1292" (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) (S3-5), Sagro-Chem's "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6), Nitrokemia's or Monsanto's "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-azaspiro [4.5] decane) (S3-7), "TI-35" (1-dichloroacetylazepane) (S3-8), "diclonon" (dicyclonon) 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) (S3-10), and its (R) isomer (S3-11).

[0572] S4) Compounds from the class of acylsulfonamides (S4):

[0573] S4 a ) formula (S4 a ) and their salts, as described in WO-A-97 / 45016,

[0574]

[0575] in:

[0576] R A 1 For (C 1 -C 6 )-alkyl, (C 3 -C 6)-cycloalkyl, wherein the last two groups are selected from halogen, (C 1 -C 4 )-alkoxy, (C 1 -C 6 )-haloalkoxy and (C 1 -C 4 )-alkylthio and in the case of cyclic groups are also selected from (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl v A Substituted by a substituent;

[0577] R A 2 For halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, CF 3 ;

[0578] m A is 1 or 2;

[0579] v A is 0, 1, 2, or 3;

[0580] S4 b ) formula (S4 b ) of the 4-(benzoylsulfamoyl)benzamide type and their salts, as described in WO-A-99 / 16744,

[0581]

[0582] in:

[0583] R B 1 , R B 2 are independently hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl,

[0584] R B 3 For halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4)-haloalkyl or (C 1 -C 4 )-alkoxy and

[0585] m B is 1 or 2,

[0586] For example,

[0587] R B 1 = cyclopropyl, R B 2 = hydrogen, and (R B 3 )=2-OMe("cyclopropanesulfonamide", S4-1),

[0588] R B 1 = cyclopropyl, R B 2 = hydrogen, and (R B 3 )=5-Cl-2-OMe(S4-2),

[0589] R B 1 =Ethyl, R B 2 = hydrogen, and (R B 3 )=2-OMe(S4-3),

[0590] R B 1 = isopropyl, R B 2 = hydrogen, and (R B 3 )=5-Cl-2-OMe(S4-4) and

[0591] R B 1 = isopropyl, R B 2 = hydrogen, and (R B 3 )=2-OMe(S4-5);

[0592] S4 c ) comes from formula (S4 c ) of the benzoylsulfamoylphenylurea class, as described in EP-A-365484,

[0593]

[0594] in:

[0595] R C1 , R C 2 are independently hydrogen, (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl,

[0596] R C 3 For halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, CF 3 and

[0597] m C is 1 or 2;

[0598] For example:

[0599] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,

[0600] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0601] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea;

[0602] S4 d ) formula (S4 d ) of the N-phenylsulfonyl terephthalamide type, which are known, for example, from CN 101838227,

[0603]

[0604] in:

[0605] R D 4 For halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, CF 3 ;

[0606] m D is 1 or 2;

[0607] R D 5 For hydrogen, (C1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 5 -C 6 )-cycloalkenyl.

[0608] S5) Active ingredients (S5) from the class of hydroxyaromatic compounds and aromatic-aliphatic carboxylic acid derivatives, for example ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001.

[0609] S6) Active ingredients (S6) from the class of 1,2-dihydroquinoxaline-2-ones, for example 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxaline-2-one, as described in WO-A-2005 / 112630.

[0610] S7) Compounds from the class of diphenylmethoxyacetic acid derivatives (S7), for example methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid, as described in WO-A-98 / 38856.

[0611] S8) A compound of formula (S8), as described in WO-A-98 / 27049,

[0612]

[0613] where the symbols and exponents are defined as follows:

[0614] R D 1 For halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C4 )-alkoxy, (C 1 -C 4 )-haloalkoxy,

[0615] R D 2 is hydrogen or (C 1 -C 4 )-alkyl,

[0616] R D 3 For hydrogen, (C 1 -C 8 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl or aryl, wherein each of the aforementioned carbon-containing groups is unsubstituted or substituted by one or more, preferably up to three, identical or different groups selected from halogen and alkoxy; or a salt thereof,

[0617] n D An integer from 0 to 2.

[0618] S9) Active ingredients (S9) from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones, for example 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999 / 000020.

[0619] S10 a ) or (S10 b )

[0620] As described in WO-A-2007 / 023719 and WO-A-2007 / 023764

[0621]

[0622] in:

[0623] R E 1 For halogen, (C 1 -C 4 )-alkyl, methoxy, nitro, cyano, CF 3 、OCF 3 ,

[0624] Y E , Z Eare independently O or S,

[0625] n E is an integer from 0 to 4,

[0626] R E 2 For (C 1 -C 16 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-cycloalkyl, aryl; benzyl, halogenated benzyl,

[0627] R E 3 is hydrogen or (C 1 -C 6 )-alkyl.

[0628] S11) Active ingredients of the oxyimino compound type known as seed dressing agents (S11), for example

[0629] "oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet / sorghum against damage by isopropylamine,

[0630] "fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a seed dressing safener for millet / sorghum against damage by isopropylamine, and

[0631] "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet / sorghum against damage by metolachlor.

[0632] S12) Active ingredients from the class of isothiochromanones (S12), for example methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998 / 13361.

[0633] S13) one or more compounds from the group (S13):

[0634] "naphthalic anhydride" (1,8-naphthalene dicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for corn against damage by thiocarbamate herbicides,

[0635] "fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for sown rice against pretilachlor,

[0636] "flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), known as a seed dressing safener for millet / sorghum against damage by alachlor and metolachlor,

[0637] "CL 304415" from American Cyanamid (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4), which is known as a safener for corn against damage by imidazolinones,

[0638] "MG 191" from Nitrokemia (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5), which is known as a safener for corn,

[0639] "MG 838" from Nitrokemia (CAS number 133993-74-5)

[0640] (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6),

[0641] "disulfoton" (O,O-diethyl S-2-ethylthioethyl dithiophosphate) (S13-7),

[0642] "Dietholate" (O,O-diethyl O-phenyl phosphorothioate) (S13-8),

[0643] "mephenate" (4-chlorophenylmethylcarbamate) (S13-9).

[0644] S14) Active ingredients which, in addition to their herbicidal action against harmful plants, also have a safener effect on crop plants such as rice, e.g.

[0645] "dimepiperate" or "MY-93" (S-1-methyl-1-phenylethylpiperidin-1-carbothioate), which is known as a safener for rice against damage by the herbicide molinate,

[0646] "daimuron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide imazosulfuron,

[0647] "cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087270), which is known as a safener for rice against damage by some herbicides,

[0648] "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides,

[0649] "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) (CAS Reg. No. 54091-06-4) from Kumiai, which is known as a safener in rice against damage by some herbicides.

[0650] S15) A compound of formula (S15) or a tautomer thereof

[0651]

[0652] As described in WO-A-2008 / 131861 and WO-A-2008 / 131860

[0653] in:

[0654] R H 1 For (C 1 -C 6 )-haloalkyl group, and

[0655] R H 2 is hydrogen or a halogen, and

[0656] R H 3 , R H 4 are independently hydrogen, (C 1 -C 16 )-alkyl, (C2 -C 16 )-alkenyl or (C 2 -C 16 )-alkynyl,

[0657] Each of the last three groups is unsubstituted or substituted by one or more selected from halogen, hydroxyl, cyano, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylamino, di[(C 1 -C 4 )-alkyl]amino, [(C 1 -C 4 )-alkoxy]carbonyl, [(C 1 -C 4 )-haloalkoxy]carbonyl, unsubstituted or substituted (C 3 -C 6 )-cycloalkyl, unsubstituted or substituted phenyl and unsubstituted or substituted heterocyclic groups,

[0658] or (C 3 -C 6 )-cycloalkyl, (C 4 -C 6 )-cycloalkenyl, one side of the ring is fused to a 4- to 6-membered saturated or unsaturated carbocyclic ring (C 3 -C 6 )-cycloalkyl or a 4- to 6-membered saturated or unsaturated carbocyclic ring fused to one side of the ring (C 4 -C 6 )-cycloalkenyl,

[0659] Each of the last four groups is unsubstituted or substituted by one or more selected from halogen, hydroxyl, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylamino, di[(C 1 -C 4)-alkyl]amino, [(C 1 -C 4 )-alkoxy]carbonyl, [(C 1 -C 4 )-haloalkoxy]carbonyl, unsubstituted or substituted (C 3 -C 6 )-cycloalkyl, unsubstituted or substituted phenyl and unsubstituted or substituted heterocyclic groups,

[0660] or

[0661] R H 3 For (C 1 -C 4 )-alkoxy, (C 2 -C 4 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy or (C 2 -C 4 )-haloalkoxy, and

[0662] R H 4 is hydrogen or (C 1 -C 4 )-alkyl, or

[0663] R H 3 and R H 4 Together with the directly attached nitrogen atom, it represents a four- to eight-membered heterocyclic ring which, in addition to the nitrogen atom, may also contain further ring heteroatoms, preferably up to two further ring heteroatoms selected from N, O and S, and which is unsubstituted or replaced by one or more radicals selected from halogen, cyano, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy and (C 1 -C 4 )-alkylthio groups.

[0664] S16) are active ingredients that are mainly used as herbicides but also have a safener effect on crop plants, such as (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 3,6-dichloro-2-methoxybenzoic acid 1-(ethoxycarbonyl)ethyl ester (lactidichlor-ethyl).

[0665] Preferred safeners for combination with the compounds of formula (I) and / or their salts according to the invention, in particular with the compounds of formulae (I.1) to (I.182) and / or their salts, are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester and isoxadifen-ethyl.

[0666] C. Biological Examples

[0667] 1. Pre-emergence weed control effect and crop plant compatibility

[0668] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are placed in sandy loam in wood fiber pots and covered with soil. The compound of the invention formulated in the form of a wettable powder (WP) or as an emulsion concentrate (EC) is then applied to the surface of the covered soil in an amount of water equal to 600 to 800 L / ha with the addition of 0.2% of a wetting agent as an aqueous suspension or emulsion.

[0669] After treatment, the pots were placed in a greenhouse and maintained under good test plant growth conditions. After a test period of 3 weeks, the damage to the test plants was scored visually by comparison with untreated controls (percentage (%) of herbicidal activity: 100% activity = plant dead, 0% activity = same as control plants).

[0670] Unwanted Plants / Weeds:

[0671]

[0672] 1. Pre-emergence effectiveness

[0673] As shown in the following results, the compounds of the present invention have good pre-emergence herbicidal efficacy against a wide spectrum of grass weeds and broadleaf weeds.

[0674] Table 1. Pre-emergence effects on ALOMY

[0675]

[0676]

[0677] Table 2. Pre-emergence effects on DIGSA

[0678]

[0679]

[0680] Table 3. Pre-emergence effects on ECHCG

[0681]

[0682]

[0683] Table 4. Pre-emergence effects on LOLRI

[0684]

[0685]

[0686] Table 5. Pre-emergence effects on POAAN

[0687]

[0688]

[0689] Table 6. Pre-emergence effects on SETVI

[0690]

[0691]

[0692]

[0693] Table 7. Pre-emergence effects on ABUTH

[0694] Example No. Dosage [g / ha] ABUTH [%] II-005 1280 90 II-007 1280 90 II-011 1280 90 II-013 1280 90 I-019 1280 90 I-014 1280 100 VII-009 1280 90

[0695] Table 8. Pre-emergence effects on AMARE

[0696]

[0697]

[0698] Table 9. Pre-emergence effects on KCHSC

[0699] Example No. Dosage [g / ha] KCHSC[%] II-005 1280 90 II-007 1280 100 II-011 1280 100 I-013 1280 90 II-013 1280 90 I-015 1280 100 I-016 1280 100 I-019 1280 100 I-014 1280 90 VII-002 1280 90 VII-007 1280 90 VII-010 1280 90

[0700] Table 10. Pre-emergence effects on MATIN

[0701]

[0702]

[0703] Table 11. Pre-emergence effects on STEME

[0704]

[0705]

[0706]

[0707] Table 12 Pre-emergence effects on VERPE

[0708]

[0709]

[0710] For example, compound Nos. II-005, II-007, II-011 and II-013 in Tables 1 to 12 each showed 90-100% efficacy against Alopecurus macrostachya, Digitaria sanguinalis, Echinochloa crusgalli, Lolium perenne and Setaria viridis at an application rate of 1280 g / ha.

[0711] The compounds according to the invention are therefore suitable for controlling unwanted plant growth by the pre-emergence method.

[0712] 2. Post-emergence weed control effect and crop plant compatibility

[0713] Seeds of monocotyledonous and dicotyledonous weeds and crop plants are placed in sandy loam in wood fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the single leaf stage. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then sprayed onto the green parts of the plants as aqueous suspensions or emulsions with the addition of 0.2% of a wetting agent at an application rate of water equal to 600 to 800 l / ha. After the test plants have been left in the greenhouse under optimal growth conditions for about 3 weeks, the action of the preparations is assessed visually in comparison with untreated controls (percentage (%) of herbicidal action: 100% activity = plant dead, 0% activity = same as control plants).

[0714] As shown in the results of Tables 13 to 24, the compounds of the present invention have good post-emergence herbicidal efficacy against a wide spectrum of grass weeds and broadleaf weeds.

[0715] Table 13. Post-emergence effects on ALOMY

[0716]

[0717]

[0718] Table 14. Post-emergence effects on DIGSA

[0719]

[0720]

[0721] Table 15. Post-emergence effects on ECHCG

[0722]

[0723]

[0724] Table 16. Post-emergence effects on LOLRI

[0725] Example No. Dosage [g / ha] LOLRI[%] II-005 1280 90 I-014 1280 90 VII-010 1280 90

[0726] Table 17. Post-emergence effects on POAAN

[0727]

[0728]

[0729]

[0730] Table 18. Post-emergence effects on SETVI

[0731]

[0732]

[0733] Table 19. Post-emergence effects on ABUTH

[0734]

[0735]

[0736] Table 20. Post-emergence effects on AMARE

[0737] Example No. Dosage [g / ha] AMARE[%] I-001 1280 90 I-002 1280 90 I-004 1280 90 I-005 1280 90 I-006 1280 100 I-009 1280 100 I-010 1280 90 I-012 1280 90 I-013 1280 100 II-001 1280 100 II-005 1280 90 II-007 1280 100 II-008 1280 90 II-011 1280 90 II-013 1280 90 IV-001 1280 90 V-001 1280 100 VI-001 1280 90

[0738] Table 21. Post-emergence effects on KCHSC

[0739] Example No. Dosage [g / ha] KCHSC[%] I-009 1280 100 I-006 1280 90 I-010 1280 90 I-001 1280 90 II-005 1280 90 I-012 1280 90 II-011 1280 100 I-013 1280 90 II-013 1280 90 I-015 1280 90 I-022 1280 90 I-016 1280 90 I-020 1280 90 I-019 1280 100 I-024 1280 90 I-027 1280 90 I-014 1280 100 VII-001 1280 90 VII-005 1280 100 III-005 1280 90 VII-011 1280 90 VII-008 1280 90 VII-007 1280 90 VII-006 1280 90 VII-010 1280 90 VII-009 1280 90

[0740] Table 22. Post-emergence effects on MATIN

[0741]

[0742]

[0743] Table 23. Post-emergence effects on STEME

[0744]

[0745]

[0746] Table 24. Post-emergence effects on VERPE

[0747]

[0748]

[0749]

[0750] For example, all compounds of the invention II-001, II-005, II-007 and II-013 in Tables 13 and 24 each showed an efficacy of 90-100% against Alopecurus mume, Digitaria sanguinalis, Setaria viridis and Echinochloa crusgalli at an application rate of 1280 g / ha, and are therefore suitable for controlling unwanted plant growth by the post-emergence method.

Claims

1. A compound of the general formula (I) or an agrochemically acceptable salt thereof, in: Q 1 is selected from the following groups Q 1 -1.1 to Q 1 -5.7 Q 2 is phenyl, wherein the phenyl group is unsubstituted or substituted independently in each case by o groups selected from hydrogen, fluorine, chlorine and bromine, Z is a group and Y is fluorine, chlorine, bromine, cyano, NO2, methyl, CF3 and OCF3, W is oxygen, R 1 are hydrogen, methyl and ethyl, R 2 is hydrogen, methyl, ethyl, allyl, propargyl and PhCH2, R 3 For hydrogen, R 4 is (C1-C6)-alkyl, S(O) n R 5 , OR 5 、SO2NR 6 R 7 、CO2R 8 or COR 8 , wherein the (C1-C6)-alkyl, S(O) n R 5 , OR 5 、SO2NR 6 R 7 、CO2R 8 or COR 8 is unsubstituted or is in each case independently of one another replaced by m selected from hydrogen, OR 5 、S(O) n R 5 、SO2NR 6 R 7 、CO2R 8 , COR 6 NR 6 CO2R 8 substituted by a group R 5 Methyl, ethyl, CF3, CH2CF3, R 6 for hydrogen and R 5 , R 7 is hydrogen, methyl, ethyl and ethyl-2-acetyl, R 8 For methyl and ethyl, R 9 is hydrogen, fluorine, chlorine, bromine, cyano, hydroxyl, methyl, ethyl, OCH3, CF3 and OCF3, m is 1, n is 0, 1, or 2, o is 0, 1, or 2.

2. An agrochemical composition comprising a) at least one compound of the general formula (I) as defined in claim 1 or an agrochemically acceptable salt thereof, and b) auxiliaries and additives customary in crop protection.

3. An agricultural chemical composition comprising a) at least one compound of the general formula (I) as defined in claim 1 or an agrochemically acceptable salt thereof, b) one or more active agrochemical ingredients other than component a), and optionally c) auxiliaries and additives customary in crop protection.

4. A method for controlling unwanted vegetation or regulating the growth of plants, wherein an effective amount of at least one compound of the general formula (I) as defined in claim 1 or an agrochemically acceptable salt thereof is applied to the plants, seeds or the area in which the plants grow.

5. Use of a compound of the general formula (I) or an agrochemically acceptable salt thereof as defined in claim 1 as a herbicide.

6. The use according to claim 5, wherein the compound of general formula (I) or an agrochemically acceptable salt thereof is used for controlling harmful plants.

7. The use according to claim 6, wherein the plant is a transgenic or non-transgenic crop plant.

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