TW202328150A - Substituted thiazolopyridines, salts thereof and their use as herbicidally active substances - Google Patents

Abstract

Substituted thiazolopyridines, salts thereof and their use as herbicidally active substances. The present invention relates to substituted thiazolopyridines of the general formula (I) or salts thereof,

Description

Substituted thiazolopyridines, their salts and their use as herbicidally active substances

The present invention relates to the technical field of crop protection agents, especially herbicides for selectively controlling broad-leaved weeds and grass weeds in crops of useful plants. In particular, the present invention relates to substituted thiazolopyridines and their salts, processes for their preparation and their use as herbicides.

In use, the hitherto known crop protection agents for the selective control of harmful plants in crops of useful plants or active compounds for the control of undesired vegetation sometimes have the following disadvantages: (a) they are not herbicidal against specific harmful plants Active or insufficiently active, (b) the range of harmful plants that can be controlled by the active compound is not broad enough, (c) its selectivity among useful plant crops is too low, and/or (d) it has a toxicologically unfavorable profile .

In addition, some active compounds which can be used as plant growth regulators for many useful plants cause undesirably low harvest yields in other useful plants or are incompatible with crop plants or only within narrow application rate ranges. Some known active compounds cannot be produced economically on an industrial scale due to the difficulty in obtaining precursors and reagents, or they have only insufficient chemical stability. In the case of other active compounds, the activity is highly dependent on environmental conditions, such as climate and soil conditions.

The herbicidal activity of these known compounds, especially at low application rates, and/or their compatibility with crop plants has yet to be improved.

Various documents describe substituted thiazolopyridines as having useful biological properties and uses. WO2017/009806 and WO2015/104688 demonstrate that substituted thiazolopyridines can inhibit interleukin-1 receptor-associated kinases (IRAK), especially IRAK4 and thus be useful in the treatment of diseases and conditions induced by IRAK4. In addition, WO2019/089580 discloses that substituted thiazolopyridines or pharmaceutically acceptable salts thereof can be used in methods for treating hematological disorders and solid malignant tumors by inhibiting IRAK4 and BCL-2 kinases.

WO2018/178947 relates to the preparation of substituted thiazolopyridines and their use in the treatment of acute myeloid leukemia. WO2017/153601 relates to substituted thiazolopyridines and their use as therapeutic agents for diseases involving amyloid accumulation, such as Parkinson's disease (Parkinson's disease). Additionally, WO 2010/135524 discloses substituted thiazolopyridine inhibitors of phosphatidylinositol 3-kinase (PI3Kα) useful against proliferative diseases.

Several documents (WO2016/087373, WO2014/125651, WO2013/018928, EP1000946, WO2012/086848 and JP2019/112369) describe that substituted thiazolopyridines and acceptable salts thereof can be used as effective pest control agents. In addition, WO2003/006470 and WO2017/110863 report that substituted thiazolopyridines can be potent fungicides.

WO2010/016846 describes that substituted thiazolopyridines and related compounds are capable of modulating TGR5. This modulation of TGR5 may represent a new opportunity for the treatment of patients with metabolic syndrome (syndrome X). Finally, the publication titled "Synthesis of Thiazolo[4,5- d ]pyridines" ( Synthesis , 2008 , 15 , 2337-2346) shows various methods for the preparation of compounds containing a thiazolopyridine core.

However, the substituted thiazolopyridines or salts thereof reported herein have not been previously described as herbicidally active compounds. Surprisingly, it has now been found that substituted thiazolopyridines or salts thereof are especially suitable as herbicides.

In use, the herbicides known hitherto for controlling harmful plants in crops of useful plants or for controlling undesired vegetation have the following disadvantages: (a) they have no or insufficient herbicidal activity against specific harmful plants, (b) The range of harmful plants that can be controlled with the active compounds is not sufficiently broad and/or (c) the selectivity of the herbicide in the crop plants and its compatibility with the crop plants is too low, thereby causing undesired damage and/or undesirable Desired smaller crop harvest yield.

Therefore, there is still a need for alternative herbicides for selective application in crops of plants or for use in non-arable land, especially highly active herbicides which can be used at low application rates and/or have good compatibility with crop plants. It would also be desirable to provide alternative chemically active compounds which can be used in an advantageous manner as herbicides or plant growth regulators.

It was therefore an object of the present invention to provide herbicidally active compounds which are highly effective against economically important harmful plants even at relatively low application rates and which can be used selectively in crop plants.

Surprisingly, it has now been found that compounds according to the general formula (I) or salts thereof meet these objectives.

Accordingly, the present invention provides substituted thiazolopyridines of general formula (I): or salts thereof: (I) wherein R ¹ represents (C ₃ -C ₈ )-cycloalkyl, (C ₃ -C ₈ )-cycloalkenyl, (C ₃ -C ₈ )-cycloalkoxy, aryl, heteroaryl , heterocyclyl, bicyclic or heterobicyclic residues, wherein each of the aforementioned 8 residues is unsubstituted or independently substituted by one or more residues selected from the group R ⁵ , R ² represents hydrogen, halogen, formyl, hydroxyl, mercapto, hydroxycarbonyl, aminocarbonyl, aminothiocarbonyl, (C ₁ -C ₈ )-alkyl, (C ₁ -C ₈ )-haloalkyl, (C ₂ -C ₈ )-alkenyl, (C ₂ -C ₈ )-haloalkenyl, (C ₂ -C ₈ )-alkynyl, (C ₂ -C ₈ )-haloalkynyl, (C ₁ -C ₈ )-alkoxy, (C ₁ -C ₈ )haloalkoxy, (C ₁ -C ₈ )-alkoxy-(C ₁ -C ₈ )-alkyl, (C ₁ -C ₈ )-Alkylthio, (C ₁ -C ₈ )-Haloalkylthio, (C ₁ -C ₈ )-Alkylsulfinyl, (C ₁ -C ₈ )-Haloalkylsulfinyl, (C ₁ -C ₈ )-Alkylsulfonyl, (C ₁ -C ₈ )-Haloalkylsulfonyl, (C ₁ -C ₈ )-Alkylcarbonyl, (C ₂ -C ₈ )-Alkenylcarbonyl, (C ₂ -C ₈ )-Alkynylcarbonyl, (C ₁ -C ₈ )-Haloalkylcarbonyl, (C ₂ -C ₈ )-Haloalkenylcarbonyl, (C ₂ -C ₈ )-Haloalkynyl Carbonyl, (C ₁ -C ₈ )-alkoxycarbonyl, (C ₃ -C ₈ )-cycloalkyl, (C ₃ -C ₈ )-cycloalkoxy, (C ₃ -C ₈ )-cycloalkane Thio, (C ₃ -C ₈ )-cycloalkylsulfinyl, (C ₃ -C ₈ )-cycloalkylsulfonyl, (C ₃ -C ₈ )-halocycloalkyl, (C ₃ -C ₈ )-halocycloalkoxy, (C ₃ -C ₈ )-halocycloalkylthio, (C ₃ -C ₈ )-halocycloalkylsulfinyl, (C ₃ - C ₈ )-halocycloalkylsulfonyl, (C ₃ -C ₈ )-cycloalkyl-(C ₁ -C ₈ )-alkyl, (C ₁ -C ₈ )-alkyl-(C ₃ -C ₈ )-cycloalkyl, (C ₃ -C ₈ )-cycloalkylcarbonyl, (C ₃ -C ₈ )-cycloalkyl-(C ₁ -C ₈ )-alkylcarbonyl, (C ₁ - C ₈ )-alkylaminocarbonyl, (C ₂ -C ₁₂ )-dialkylaminocarbonyl, (C ₁ -C ₈ )-alkylaminosulfonyl, (C ₂ -C ₁₂ )-di Alkylaminosulfonyl or (C ₃ -C ₁₂ )-trialkylsilyl, R ³ represents hydrogen, halogen, cyano, (C ₁ -C ₈ )-alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₂ -C ₈ )-alkenyl, (C ₂ -C ₈ )-haloalkenyl, (C ₁ -C ₈ )-alkoxy, (C ₁ -C ₈ )haloalkoxy , (C ₁ -C ₈ )-Alkylthio, (C ₁ -C ₈ )-Haloalkylthio, (C ₃ -C ₈ )-Cycloalkyl, (C ₃ -C ₈ )-Halocycloalkyl , (C ₃ -C ₈ )-cycloalkoxy or (C ₃ -C ₈ )-halocycloalkoxy, R ⁴ represents hydrogen, halogen, cyano, mercapto, hydroxycarbonyl, (C ₁ - C ₈ )-alkoxycarbonyl, aminocarbonyl, aminothiocarbonyl, (C ₁ -C ₈ )-alkylaminocarbonyl, (C ₂ -C ₁₂ )-dialkylaminocarbonyl, (C ₂ -C ₈ )-alkenylaminocarbonyl, N- (C ₂ -C ₈ )-alkenyl- N- (C ₁ -C ₈ )-alkylaminocarbonyl, (C ₁ -C ₈ )-halogenated alkyl radical, (C ₃ -C ₈ )-cycloalkyl, (C ₃ -C ₈ )-halocycloalkyl, (C ₁ -C ₈ )haloalkoxy, (C ₃ -C ₈ )-cycloalkoxy radical, (C ₃ -C ₈ )-halocycloalkoxy, (C ₁ -C ₈ )-alkoxy-(C ₁ -C ₈ )-alkyl, (C ₃ -C ₁₂ )-trioxane Silyl, or represents unsubstituted or optionally substituted benzyl by one or more residues selected from group R ⁵ , or represents optionally substituted by one or more residues selected from cyano, (C ₁ -C ₈ )-Alkylcarbonyl, (C ₁ -C ₈ )-Haloalkylcarbonyl, Hydroxycarbonyl, (C ₁ -C ₈ )-Alkoxycarbonyl, Aminocarbonyl, (C ₁ -C ₈ )-Alkylamine ylcarbonyl, (C ₂ -C ₁₂ )-dialkylaminocarbonyl, (C ₂ -C ₈ )-alkenylaminocarbonyl and N -(C ₂ -C ₈ )-alkenyl- N -(C ₁ -C ₈ )-Alkylaminocarbonyl substituted (C ₁ -C ₈ )-alkyl, or represents optionally one or more selected from hydroxycarbonyl, (C ₁ -C ₈ )-alkoxy Alkylcarbonyl, aminocarbonyl, (C ₁ -C ₈ )-alkylaminocarbonyl, (C ₂ -C ₁₂ )-dialkylaminocarbonyl, (C ₂ -C ₈ )-alkenylaminocarbonyl and (C ₁ -C ₈ )-alkoxy substituted by _the residue of N- (C ₂ -C 8 )-alkenyl-N-(C ₁ -C ₈ )-alkylaminocarbonyl, or representing One or more selected from hydroxycarbonyl, (C ₁ -C ₈ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₈ )-alkylaminocarbonyl, (C ₂ -C ₁₂ )-dioxane Residues of aminocarbonyl, (C ₂ -C ₈ )-alkenylaminocarbonyl and N -(C ₂ -C ₈ )-alkenyl- N -(C ₁ -C ₈ )-alkylaminocarbonyl Substituted (C ₁ -C ₈ )-alkylthio, or represented by one or more selected from hydroxycarbonyl, (C ₁ -C ₈ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₈ ) -Alkylaminocarbonyl, (C ₂ -C ₁₂ )-dialkylaminocarbonyl, (C ₂ -C ₈ )-alkenylaminocarbonyl and N- (C ₂ -C ₈ )-alkenyl- N -(C ₁ -C ₈ )-alkylaminocarbonyl substituted (C ₁ -C ₈ )-alkylamino group, or represented by one or more selected from hydroxycarbonyl, (C ₁ -C ₈ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₈ )-alkylaminocarbonyl, (C ₂ -C ₁₂ )-dialkylaminocarbonyl, (C ₂ -C ₈ )-alkenyl Aminocarbonyl and (C ₂ -C ₁₂ )-dialkylamino substituted by residues of N- (C ₂ -C ₈ )-alkenyl- N- (C ₁ -C ₈ )-alkylaminocarbonyl , or represent (C ₁ -C ₈ )-haloalkylthio, (C ₃ -C ₈ )-cycloalkylthio, (C ₃ -C ₈ )-halocycloalkylthio, (C ₁ -C ₈ ) -Alkylsulfinyl, (C ₁ -C ₈ )-haloalkylsulfinyl, (C ₃ -C ₈ )-cycloalkylsulfinyl, (C ₃ -C ₈ )-halogenated ring Alkylsulfinyl, (C ₁ -C ₈ )-alkylsulfonyl, (C ₁ -C ₈ )-haloalkylsulfonyl, (C ₃ -C ₈ )-cycloalkylsulfonyl or (C ₃ -C ₈ )-Halocycloalkylsulfonyl, and R ⁵ represents halogen, formyl, hydroxyl, hydroxycarbonyl, nitro, cyano, amino, aminocarbonyl, aminothiocarbonyl , (C ₁ -C ₈ )-Alkyl, (C ₁ -C ₈ )-Haloalkyl, (C ₂ -C ₈ )-Alkenyl, (C ₂ -C ₈ )-Haloalkenyl, (C ₂ -C ₈ )-alkynyl, (C ₂ -C ₈ )-haloalkynyl, (C ₁ -C ₈ )-alkoxy, (C ₁ -C ₈ )-haloalkoxy, (C ₁ -C ₈ )-Alkylthio, (C ₁ -C ₈ )-Haloalkylthio, (C ₁ -C ₈ )-Alkylsulfinyl, (C ₁ -C ₈ )-Haloalkylsulfinyl, ( C ₁ -C ₈ )-Alkylsulfonyl, (C ₁ -C ₈ )-Haloalkylsulfonyl, (C ₁ -C ₈ )-Alkylcarbonyl, (C ₁ -C ₈ )-Haloalkylcarbonyl , (C ₂ -C ₈ )-alkenylcarbonyl, (C ₂ -C ₈ )-halogenated alkenylcarbonyl, (C ₂ -C ₈ )-alkynylcarbonyl, (C ₂ -C ₈ )-halogenated alkyne ylcarbonyl, (C ₁ -C ₈ )-alkoxycarbonyl, (C ₁ -C ₈ )-haloalkoxycarbonyl, (C ₃ -C ₈ )-cycloalkyl, (C ₃ -C ₈ )-halogen Cycloalkyl, (C ₃ -C ₈ )-cycloalkoxy, (C ₃ -C ₈ )-halocycloalkoxy, (C ₃ -C ₈ )-cycloalkylthio, (C ₃ - C ₈ )-halocycloalkylthio, (C ₃ -C ₈ )-cycloalkylsulfinyl, (C ₃ -C ₈ )-halocycloalkylsulfinyl, (C ₃ -C ₈ )-cycloalkylsulfonyl, (C ₃ -C ₈ )-halocycloalkylsulfonyl, (C ₃ -C ₈ )-cycloalkyl-(C ₁ -C ₈ )-alkyl, (C ₁ -C ₈ )-Alkyl-(C ₃ -C ₈ )-Cycloalkyl, (C ₁ -C ₈ )-Alkoxycarbonyl-(C ₁ -C ₈ )-Alkyl, Hydroxycarbonyl- (C ₁ -C ₈ )-Alkyl, (C ₃ -C ₈ )-Cycloalkylcarbonyl, (C ₃ -C ₈ )-Cycloalkyl-(C ₁ -C ₈ )-Alkylcarbonyl, (C ₁ -C ₈ )-Alkylamino, (C ₂ -C ₁₂ )-Dialkylamino, (C ₁ -C ₈ )-Alkylaminocarbonyl, (C ₂ -C ₁₂ )-Dialkyl Aminocarbonyl, (C ₁ -C ₈ )-Alkylaminosulfonyl, (C ₂ -C ₁₂ )-Dialkylaminosulfonyl or (C ₃ -C ₁₂ )-Trialkylsilyl .

Compounds of general formula (I) can be obtained by adding a suitable inorganic or organic acid to a basic group (such as amine, alkylamine, dialkylamine, hexahydropyridyl, morpholinyl or pyridyl) (such as mineral acids such as HCl, HBr, _{H2SO4 , H3PO4 ,} or _HNO3 ; or organic acids such as carboxylic acids (such as formic, acetic, propionic, oxalic, lactic, or salicylic acids) or sulfonic acids (e.g. p-toluenesulfonic acid)) to form salts. In such cases, the salts will include the conjugate base of the acid as the anion. Suitable substituents in deprotonated form, such as sulfonic acids, certain sulfonamides or carboxylic acids, are capable of forming internal salts with groups which are themselves protonatable, such as amine groups. Salts may also be formed by the action of bases on the compounds of general formula (I). Suitable bases are, for example, organic amines (such as trialkylamines, morpholine, hexahydropyridine and pyridine) and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates (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 metal salts, especially alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts) or ammonium salts, salts with organic amines or quaternary ammonium salts ( For example a cation of formula [NR ^a R ^b R ^c R ^d ] ⁺ , wherein R ^a to R ^d is each independently an organic group, especially an alkyl, aryl, arylalkyl or alkylaryl). Also suitable are alkyl columbites and alkyl cobaltium oxide salts, for example (C ₁ -C ₄ )-trialkyl cobaltium and (C ₁ -C ₄ )-trialkyl cobaltium oxide salts.

The substituted thiazolopyridines of the general formula (I) of the present invention can exist in various tautomeric structures depending on external conditions (such as pH, solvent and temperature), and all structures are covered by the general formula (I).

The compound of formula (I) and its salts used in the present invention are also referred to as "compound of general formula (I)" hereinafter.

The present invention preferably provides compounds of general formula (I), wherein R ¹ represents (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, (C ₃ -C ₆ )-cyclo Alkoxy, aryl, heteroaryl, heterocyclyl, bicyclic or heterobicyclic residues, wherein each of the aforementioned 8 residues is unsubstituted or independently selected from one or more radicals The residue of group R ⁵ is substituted, R ² represents hydrogen, halogen, formyl, hydroxyl, mercapto, hydroxycarbonyl, aminocarbonyl, aminothiocarbonyl, (C ₁ -C ₆ )-alkyl, ( C ₁ -C ₆ )-haloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-haloalkenyl, (C ₂ -C ₆ )-alkynyl, (C ₂ -C ₆ )-haloalkynyl, (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )haloalkoxy, (C ₁ -C ₆ )-alkoxy-(C ₁ -C ₆ ) -Alkyl, (C ₁ -C ₆ )-Alkylthio, (C ₁ -C ₆ )-Haloalkylthio, (C ₁ -C ₆ )-Alkylsulfinyl, (C ₁ -C ₆ ) -Haloalkylsulfinyl, (C ₁ -C ₆ )-Alkylsulfonyl, (C ₁ -C ₆ )-Haloalkylsulfonyl, (C ₁ -C ₆ )-Alkylcarbonyl, (C ₂ -C ₆ )-alkenylcarbonyl, (C ₂ -C ₆ )-alkynylcarbonyl, (C ₁ -C ₆ )-haloalkylcarbonyl, (C ₂ -C ₆ )-halogenylcarbonyl, (C ₂ -C ₆ )-haloalkynylcarbonyl, (C ₁ -C ₆ )-alkoxycarbonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-cycloalkylthio, (C ₃ -C ₆ )-cycloalkylsulfinyl, (C ₃ -C ₆ )-cycloalkyl-sulfonyl, (C ₃ -C ₆ )-halogenated cycloalkyl, (C ₃ -C ₆ )-halogenated cycloalkoxy, (C ₃ -C ₆ )-halogenated cycloalkylthio, (C ₃ -C ₆ )-halogenated ring Alkylsulfinyl, (C ₃ -C ₆ )-halocycloalkylsulfonyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-Alkyl-(C ₃ -C ₆ )-Cycloalkyl, (C ₃ -C ₆ )-Cycloalkylcarbonyl, (C ₃ -C ₆ )-Cycloalkyl-(C ₁ -C ₆ )-Alkylcarbonyl, (C ₁ -C ₆ )-Alkylaminocarbonyl, (C ₂ -C ₁₀ )-Dialkylaminocarbonyl, (C ₁ -C ₆ )-Alkyl-aminosulfonyl Acyl, (C ₂ -C ₁₀ )-dialkylaminosulfonyl or (C ₃ -C ₁₀ )-trialkylsilyl, R ³ represents hydrogen, halogen, cyano, (C ₁ -C ₆ )-Alkyl, (C ₁ -C ₆ )-Haloalkyl, (C ₂ -C ₆ )-Alkenyl, (C ₂ -C ₆ )-Haloalkenyl, (C ₁ -C ₆ )-Alkoxy radical, (C ₁ -C ₆ )haloalkoxy, (C ₁ -C ₆ )-alkylthio, (C ₁ -C ₆ )-haloalkylthio, (C ₃ -C ₆ )-cycloalkyl, ( C ₃ -C ₆ )-halogenated cycloalkyl, (C ₃ -C ₆ )-cycloalkoxy or (C ₃ -C ₆ )-halogenated cycloalkoxy, R ⁴ represents hydrogen, halogen, cyano , mercapto, hydroxycarbonyl, (C ₁ -C ₆ )-alkoxycarbonyl, aminocarbonyl, aminothiocarbonyl, (C ₁ -C ₆ )-alkylaminocarbonyl, (C ₂ -C ₁₀ )-Dialkylamino-carbonyl, (C ₂ -C ₆ )-alkenylaminocarbonyl, N- (C ₂ -C ₆ )-alkenyl- N- (C ₁ -C ₆ )-alkyl Aminocarbonyl, (C ₁ -C ₆ )-haloalkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-halocycloalkyl, (C ₁ -C ₆ )haloalkoxy radical, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-halocycloalkoxy, (C ₁ -C ₆ )-alkoxy-(C ₁ -C ₆ )- Alkyl, (C ₃ -C ₁₀ )-trialkylsilyl, or represents benzyl which is unsubstituted or optionally substituted by one or more residues selected from group R ⁵ , or represents optionally substituted by one or more selected from cyano, (C ₁ -C ₆ )-alkylcarbonyl, (C ₁ -C ₆ )-haloalkylcarbonyl, hydroxycarbonyl, (C ₁ -C ₆ )-alkoxycarbonyl, amino Carbonyl, (C ₁ -C ₆ )-alkylaminocarbonyl, (C ₂ -C ₁₀ )-dialkylamino-carbonyl, (C ₂ -C ₆ )-alkenylaminocarbonyl and N- (C ₂ -C ₆ )-alkenyl- N- (C ₁ -C ₆ )-alkylaminocarbonyl substituted (C ₁ -C ₆ )-alkyl, or represents optionally one or more From hydroxycarbonyl, (C ₁ -C ₆ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₆ )-alkylaminocarbonyl, (C ₂ -C ₁₀ )-dialkylaminocarbonyl, _{The (} C _{1 _} _ _{_ _ _} -C ₆ )-alkoxy, or represents optionally one or more selected from hydroxycarbonyl, (C ₁ -C ₆ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₆ )-alkyl Aminocarbonyl, (C ₂ -C ₁₀ )-dialkylaminocarbonyl, (C ₂ -C ₆ )-alkenylaminocarbonyl and N- (C ₂ -C ₆ )-alkenyl- N- (C ( _{C 1} -C ₆ )-alkylthio substituted by the residue of ₁ -C ₆ )-alkylaminocarbonyl, or represented by one or more groups selected from hydroxycarbonyl, (C ₁ -C ₆ )-alkoxy Alkylcarbonyl, aminocarbonyl, (C ₁ -C ₆ )-alkylaminocarbonyl, (C ₂ -C ₁₀ )-dialkylaminocarbonyl, (C ₂ -C ₆ )-alkenylaminocarbonyl and ₍ C ₁ -C ₆ )-alkylamino substituted by the residue of N- (C ₂ -C 6 )-alkenyl-N-(C ₁ -C ₆ )-alkylaminocarbonyl, or represented by a or more selected from hydroxycarbonyl, (C ₁ -C ₆ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₆ )-alkylaminocarbonyl, (C ₂ -C ₁₀ )-dialkyl Aminocarbonyl, (C ₂ -C ₆ )-alkenylaminocarbonyl and N -(C ₂ -C ₆ )-alkenyl- N -(C ₁ -C ₆ )-alkylaminocarbonyl residue substitution (C ₂ -C ₁₀ )-dialkylamino, or (C ₁ -C ₆ )-haloalkylthio, (C ₃ -C ₆ )-cycloalkylthio, (C ₃ -C ₆ )- Halocycloalkylthio, (C ₁ -C ₆ )-Alkylsulfinyl, (C ₁ -C ₆ )-Haloalkylsulfinyl, (C ₃ -C ₆ )-Cycloalkylsulfinyl Acyl group, (C ₃ -C ₆ )-halocycloalkylsulfinyl group, (C ₁ -C ₆ )-alkylsulfonyl group, (C ₁ -C ₆ )-haloalkylsulfonyl group, ( C ₃ -C ₆ )-cycloalkylsulfonyl or (C ₃ -C ₆ )-halogenated cycloalkylsulfonyl, and R ⁵ represents halogen, formyl, hydroxyl, hydroxycarbonyl, nitro, cyano group, amino, aminocarbonyl, aminothiocarbonyl, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-haloalkenyl, (C ₂ -C ₆ )-alkynyl, (C ₂ -C ₆ )-haloalkynyl, (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy, (C ₁ -C ₆ )-alkylthio, (C ₁ -C ₆ )-haloalkylthio, (C ₁ -C ₆ )-alkylsulfinyl, (C ₁ -C ₆ )-haloalkylsulfinyl, (C ₁ -C ₆ )-alkylsulfonyl, (C ₁ -C ₆ )-haloalkylsulfinyl, (C ₁ -C ₆ )-alkane ylcarbonyl, (C ₁ -C ₆ )-haloalkylcarbonyl, (C ₂ -C ₆ )-alkenyl-carbonyl, (C ₂ -C ₆ )-haloalkenylcarbonyl, (C ₂ -C ₆ )- Alkynylcarbonyl, (C ₂ -C ₆ )-haloalkynylcarbonyl, (C ₁ -C ₆ )-alkoxycarbonyl, (C ₁ -C ₆ )-haloalkoxycarbonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-halocyclo-alkyl, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-halocycloalkoxy, ( C ₃ -C ₆ )-cycloalkylthio, (C ₃ -C ₆ )-halocycloalkylthio, (C ₃ -C ₆ )-cycloalkylsulfinyl, (C ₃ -C ₆ ) -Halocycloalkylsulfinyl, (C ₃ -C ₆ )-cycloalkylsulfonyl, (C ₃ -C ₆ )-halocycloalkylsulfinyl, (C ₃ -C ₆ ) -cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-(C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-alkoxy Carbonyl-(C ₁ -C ₆ )-Alkyl, Hydroxycarbonyl-(C ₁ -C ₆ )-Alkyl, (C ₃ -C ₆ )-Cycloalkylcarbonyl, (C ₃ -C ₆ )-Cycloalkane -(C ₁ -C ₆ )-alkylcarbonyl, (C ₁ -C ₆ )-alkylamino, (C ₂ -C ₁₀ )-dialkylamino, (C ₁ -C ₆ )-alkane Aminocarbonyl, (C ₂ -C ₁₀ )-dialkylaminocarbonyl, (C ₁ -C ₆ )-alkylaminosulfonyl, (C ₂ -C ₁₀ )-dialkylaminosulfonyl Acyl or (C ₃ -C ₁₀ )-trialkylsilyl.

The present invention preferably provides compounds of general formula (I), wherein R ¹ represents (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, (C ₃ -C ₆ )-ring Alkoxy, aryl, heteroaryl, heterocyclyl, bicyclic or heterobicyclic residues, wherein each of the aforementioned 8 residues is unsubstituted or independently selected from one or more radicals The residue of group R ⁵ is substituted, R ² represents hydrogen, halogen, formyl, hydroxyl, mercapto, hydroxycarbonyl, aminocarbonyl, aminothiocarbonyl, (C ₁ -C ₄ )-alkyl, ( C ₁ -C ₄ )-haloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₂ -C ₄ )-haloalkenyl, (C ₂ -C ₄ )-alkynyl, (C ₂ -C ₄ )-haloalkynyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )haloalkoxy, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ ) -Alkyl, (C ₁ -C ₄ )-Alkylthio, (C ₁ -C ₄ )-Haloalkylthio, (C ₁ -C ₄ )-Alkylsulfinyl, (C ₁ -C ₄ ) -haloalkyl-sulfinyl, (C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ )-haloalkylsulfonyl, (C ₂ -C ₄ )-alkylcarbonyl, ( C ₂ -C ₄ )-alkenylcarbonyl, (C ₂ -C ₄ )-alkynylcarbonyl, (C ₁ -C ₄ )-haloalkylcarbonyl, (C ₂ -C ₄ )-halogenylcarbonyl, ( C ₂ -C ₄ )-haloalkynylcarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkoxy , (C ₃ -C ₆ )-cycloalkylthio, (C ₃ -C ₆ )-cycloalkylsulfinyl, (C ₃ -C ₆ )-cycloalkyl-sulfonyl, (C ₃ - C ₆ )-halocycloalkyl, (C ₃ -C ₆ )-halocycloalkoxy, (C ₃ -C ₆ )-halocycloalkylthio, (C ₃ -C ₆ )-halo Cycloalkylsulfinyl, (C ₃ -C ₆ )-halocycloalkylsulfonyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkyl-(C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkylcarbonyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ - C ₄ )-Alkylcarbonyl, (C ₁ -C ₄ )-Alkylaminocarbonyl, (C ₂ -C ₈ )-Dialkylaminocarbonyl, (C ₁ -C ₆ )-Alkylamino- Sulfonyl, (C ₂ -C ₈ )-dialkylaminosulfonyl or (C ₃ -C ₈ )-trialkylsilyl, R ³ represents hydrogen, halogen, cyano, (C ₁ -C ₄ )-Alkyl, (C ₁ -C ₄ )-Haloalkyl, (C ₂ -C ₄ )-Alkenyl, (C ₂ -C ₄ )-Haloalkenyl, (C ₁ -C ₄ )-Alkane Oxygen, (C ₁ -C ₄ )haloalkoxy, (C ₁ -C ₄ )-alkylthio, (C ₁ -C ₄ )-haloalkylthio, (C ₃ -C ₄ )-cycloalkyl, (C ₃ -C ₄ )-halogenated cycloalkyl, (C ₃ -C ₄ )-cycloalkoxy or (C ₃ -C ₄ )-halogenated cycloalkoxy, R ⁴ represents hydrogen, halogen, cyano thiol, hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, aminocarbonyl, aminothiocarbonyl, (C ₁ -C ₄ )-alkylaminocarbonyl, (C ₂ - C ₈ )-dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl, N- (C ₂ -C ₄ )-alkenyl- N- (C ₁ -C ₄ )-alkyl Aminocarbonyl, (C ₁ -C ₄ )-haloalkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-halocycloalkyl, (C ₁ -C ₄ )haloalkoxy radical, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-halocycloalkoxy, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )- Alkyl, (C ₃ -C ₈ )-trialkylsilyl, or benzyl which is unsubstituted or optionally substituted by one or more residues selected from group R ⁵ , or which is optionally represented by a or more selected from cyano, (C ₁ -C ₄ )-alkylcarbonyl, (C ₁ -C ₄ )-haloalkylcarbonyl, hydroxycarbonyl, (C ₁ -C ₄ )-alkoxy-carbonyl, amine Alkylcarbonyl, (C ₁ -C ₄ )-alkylaminocarbonyl, (C ₂ -C ₈ )-dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl and N -(C ₂ -C ₄ )-alkenyl- N- (C ₁ -C ₄ )-alkylaminocarbonyl substituted (C ₁ -C ₄ )-alkyl, or represents optionally one or more From hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₄ )-alkylaminocarbonyl, (C ₂ -C ₈ )-dialkylamino-carbonyl , (C ₂ -C ₄ )-alkenylaminocarbonyl and N- (C ₂ -C ₄ )-alkenyl- N- (C ₁ -C ₄ )-alkylaminocarbonyl residues substituted (C ₁ -C ₄ )-alkoxy, or represents optionally one or more selected from hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₄ )-alk Aminocarbonyl, (C ₂ -C ₈ )-dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl and N -(C ₂ -C ₄ )-alkenyl- N- ( (C ₁ -C ₄ )-alkylthio substituted by the residue of C ₁ -C ₄ )-alkylaminocarbonyl, or represented by one or more groups selected from hydroxycarbonyl, (C ₁ -C ₄ )-alk Oxycarbonyl, aminocarbonyl, (C ₁ -C ₄ )-alkylamino-carbonyl, (C ₂ -C ₈ )-dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylamino Carbonyl and N- (C ₂ -C ₄ )-alkenyl- N- (C ₁ -C ₄ )-alkylaminocarbonyl residues substituted (C ₁ -C ₄ )-alkylamino, or representing One or more selected from hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₄ )-alkylaminocarbonyl, (C ₂ -C ₈ )-di Residues of alkylaminocarbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl and N- (C ₂ -C ₄ )-alkenyl- N- (C ₁ -C ₄ )-alkylaminocarbonyl (C ₂ -C ₈ )-dialkylamino group substituted by radical, or represent (C ₁ -C ₄ )-haloalkylthio, (C ₃ -C ₆ )-cycloalkylthio, (C ₃ -C ₆ )-halocycloalkylthio, (C ₁ -C ₄ )-alkylsulfinyl, (C ₁ -C ₄ )-haloalkylsulfinyl, (C ₃ -C ₆ )-cycloalkyl Sulfinyl, (C ₃ -C ₆ )-Halocycloalkylsulfinyl, (C ₁ -C ₄ )-Alkylsulfonyl, (C ₁ -C ₄ )-Haloalkylsulfonyl , (C ₃ -C ₆ )-cycloalkylsulfonyl or (C ₃ -C ₆ )-halocycloalkyl-sulfonyl, and R ⁵ represents halogen, formyl, hydroxyl, hydroxycarbonyl, nitro group, cyano, amino, aminocarbonyl, aminothiocarbonyl, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₂ -C ₄ )-alkenyl , (C ₂ -C ₄ )-haloalkenyl, (C ₂ -C ₄ )-alkynyl, (C ₂ -C ₄ )-haloalkynyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy, (C ₁ -C ₄ )-alkylthio, (C ₁ -C ₄ )-haloalkylthio, (C ₁ -C ₄ )-alkylsulfinyl , (C ₁ -C ₄ )-haloalkylsulfinyl, (C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ )-haloalkylsulfinyl, (C ₁ -C ₄ )-Alkylcarbonyl, (C ₁ -C ₄ )-Haloalkylcarbonyl, (C ₂ -C ₄ )-Alkenyl-carbonyl, (C ₂ -C ₄ )-Haloalkenylcarbonyl, (C ₂ -C ₄ )-alkynylcarbonyl, (C ₂ -C ₄ )-halogenated alkynylcarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, (C ₁ -C ₄ )-halogenated alkoxycarbonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-halocyclo-alkyl, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-halocycloalkoxy radical, (C ₃ -C ₆ )-cycloalkylthio, (C ₃ -C ₆ )-halocyclo-alkylthio, (C ₃ -C ₆ )-cycloalkylsulfinyl, (C ₃ -C ₆ )-halocycloalkylsulfinyl, (C ₃ -C ₆ )-cycloalkyl-sulfonyl, (C ₃ -C ₆ )-halocycloalkylsulfinyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkyl-(C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₄ )-alkoxycarbonyl-(C ₁ -C ₄ )-alkyl, hydroxycarbonyl-(C ₁ -C ₄ )-alkyl, (C ₃ -C ₆ )-cycloalkylcarbonyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₄ )-alkylcarbonyl, (C ₁ -C ₄ )-alkylamino, (C ₂ -C ₈ )-dialkylamino, (C ₁ - C ₄ )-Alkylaminocarbonyl, (C ₂ -C ₈ )-Dialkylaminocarbonyl, (C ₁ -C ₄ )-Alkylaminosulfonyl, (C ₂ -C ₈ )-Di Alkylaminosulfonyl or (C ₃ -C ₈ )-trialkylsilyl.

The present invention especially provides compounds of general formula (I), wherein ^R represents phenyl, furyl, pyrrolyl, thienyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, thiazolyl, isothiazolyl, thiadi Azolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, cyclopentenyl, cyclohexenyl or oxabicycloheptyl residues, wherein the aforementioned and each of the 20 residues is unsubstituted or independently substituted by one or more residues selected from the group R ⁵ , R ² represents hydrogen, halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₂ -C ₄ )-haloalkenyl, (C ₂ -C ₄ )-alkynyl, (C ₂ - C ₄ )-haloalkynyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )haloalkoxy, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-Alkyl, (C ₁ -C ₄ )-Alkylthio, (C ₁ -C ₄ )-Haloalkylthio, (C ₁ -C ₄ )-Alkylsulfinyl, (C ₁ -C ₄ )-haloalkylsulfinyl, (C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ )-haloalkylsulfonyl, (C ₁ -C ₄ )-alkylcarbonyl, ( C ₁ -C ₄ )-haloalkylcarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkoxy, ( C ₃ -C ₆ )-halocycloalkyl, (C ₃ -C ₆ )-halocycloalkoxy, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₄ )-alkyl or (C ₁ -C ₄ )-alkyl-(C ₃ -C ₆ )-cycloalkyl, R ³ represents hydrogen, halogen, cyano, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )haloalkoxy, (C ₃ -C ₄ )-cycloalkyl or (C ₃ -C ₄ )-halogen Cycloalkyl, R ⁴ represents hydrogen, halogen, cyano, mercapto, hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, aminocarbonyl, aminothiocarbonyl, (C ₁ -C ₄ )-Alkylaminocarbonyl, (C ₂ -C ₈ )-dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl, N- (C ₂ -C ₄ )-alkenyl - N -(C ₁ -C ₄ )-Alkylaminocarbonyl, (C ₁ -C ₄ )-Haloalkyl, (C ₃ -C ₆ )-Cycloalkyl, (C ₃ -C ₆ )-Halo Cycloalkyl, (C ₁ -C ₄ )haloalkoxy, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-halocycloalkoxy, (C ₁ -C ₄ ) -alkoxy-(C ₁ -C ₄ )-alkyl, or represents benzyl which is unsubstituted or optionally substituted by one or more residues selected from the group R ⁵ , or represents optionally one or Multiple selected from cyano, (C ₁ -C ₄ )-alkyl-carbonyl, (C ₁ -C ₄ )-haloalkylcarbonyl, hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, amino Carbonyl, (C ₁ -C ₄ )-alkylaminocarbonyl, (C ₂ -C ₈ )-dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl and N -(C ₂ -C ₄ )-alkenyl- N- (C ₁ -C ₄ )-alkylaminocarbonyl substituted (C ₁ -C ₄ )-alkyl, or represents optionally one or more selected from Hydroxycarbonyl, (C ₁ -C ₄ )-Alkoxycarbonyl, Aminocarbonyl, (C ₁ -C ₄ )-Alkylaminocarbonyl, (C ₂ -C ₈ )-Dialkylaminocarbonyl, ( _{( C} 1 _{_ _} _ _{_ _ _} -C ₄ )-alkoxy, or represents optionally one or more selected from hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₄ )-alkyl Aminocarbonyl, (C ₂ -C ₈ )-dialkylamino-carbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl and N -(C ₂ -C ₄ )-alkenyl- N- ( (C ₁ -C ₄ )-alkylthio substituted by the residue of C ₁ -C ₄ )-alkylaminocarbonyl, or represented by one or more groups selected from hydroxyl-carbonyl, (C ₁ -C ₄ )- Alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₄ )-alkylaminocarbonyl, (C ₂ -C ₈ )-dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylamino Carbonyl and N- (C ₂ -C ₄ )-alkenyl- N- (C ₁ -C ₄ )-alkylaminocarbonyl residues substituted (C ₁ -C ₄ )-alkylamino, or representing One or more selected from hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₄ )-alkylamino-carbonyl, (C ₂ -C ₈ )- Dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl and N -(C ₂ -C ₄ )-alkenyl- N -(C ₁ -C ₄ )-alkylaminocarbonyl Residue substituted (C ₂ -C ₈ )-dialkylamino, or represents (C ₁ -C ₄ )-haloalkylthio, (C ₁ -C ₄ )-alkylsulfinyl, (C ₁ -C ₄ )-Haloalkylsulfinyl, (C ₁ -C ₄ )-Alkylsulfonyl or (C ₁ -C ₄ )-Haloalkylsulfonyl, and R ⁵ represents halogen, nitro, cyano group, hydroxyl group, amino group, (C ₁ -C ₄ )-alkyl group, (C ₁ -C ₄ )-haloalkyl group, (C ₁ -C ₄ )-alkoxy group, (C ₁ -C ₄ )-haloalkyl group Oxygen, (C ₁ -C ₄ )-Alkylthio, (C ₁ -C ₄ )-Haloalkylthio, (C ₁ -C ₄ )-Alkylsulfinyl, (C ₁ -C ₄ )- Haloalkylsulfinyl, (C ₁ -C ₄ )-Alkylsulfonyl, (C ₁ -C ₄ )-Haloalkylsulfonyl, (C ₁ -C ₄ )-Alkyl-carbonyl, (C ₁ -C ₄ )-haloalkylcarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, (C ₁ -C ₄ )-haloalkoxycarbonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-halocycloalkyl, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-halocycloalkoxy, (C ₃ -C ₆ )-cycloalkane Thio, (C ₃ -C ₆ )-halocycloalkylthio, (C ₃ -C ₆ )-cycloalkylsulfinyl, (C ₃ -C ₆ )-halocycloalkylsulfinyl group, (C ₃ -C ₆ )-cycloalkylsulfonyl, (C ₃ -C ₆ )-halocycloalkylsulfonyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ - C ₄ )-Alkyl, (C ₁ -C ₄ )-Alkyl-(C ₃ -C ₆ )-Cycloalkyl, (C ₁ -C ₄ )-Alkoxycarbonyl-(C ₁ -C ₄ ) -Alkyl, hydroxycarbonyl-(C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkylamino or (C ₂ -C ₈ )-dialkylamino.

The present invention more specifically provides a compound of general formula (I), wherein ^R represents phenyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, oxazolyl, thienyl Diazolyl, isothiazolyl, cyclopenten-1-yl, cyclohexen-1-yl or 7-oxabicyclo[4.1.0]heptane-1-yl, wherein the aforementioned 9 residues Each of them is unsubstituted or optionally substituted by one or more residues selected from the group R ⁵ , R ² represents hydrogen, halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₂ -C ₄ )-haloalkenyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )haloalkane Oxygen, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-halocycloalkane radical, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₄ )-alkyl or (C ₁ -C ₄ )-alkyl-(C ₃ -C ₆ )-cycloalkyl, R ³ is hydrogen, halogen or (C ₁ -C ₄ )-alkyl, R ⁴ represents hydrogen, halogen, cyano, mercapto, (C ₁ -C ₄ )-alkyl, (C ₃ -C ₆ )-ring Alkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkylthio, (C ₁ -C ₄ )-Alkylsulfinyl, (C ₁ -C ₄ )-Haloalkylsulfinyl, (C ₁ -C ₄ )-Alkylsulfinyl or (C ₁ -C ₄ )-haloalkylsulfonyl, and R ⁵ represents halogen, cyano, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy , (C ₁ -C ₄ )-halo-alkoxy, (C ₃ -C ₆ )-cycloalkyl or (C ₁ -C ₄ )-alkyl-(C ₃ -C ₆ )-cycloalkyl .

The present invention more specifically provides a compound of general formula (I), wherein R ¹ represents phenyl, 2-thienyl, 3-thienyl, oxazolyl or thiadiazolyl, wherein one of the aforementioned 5 residues Each is unsubstituted or optionally substituted by one or more residues selected from the group R ⁵ , R ² represents hydrogen, halogen, (C ₁ -C ₄ )-alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl or (C ₃ -C ₆ )-cycloalkyl -(C ₁ -C ₄ )-alkyl, R ³ is hydrogen, R ⁴ represents hydrogen or mercapto, and R ⁵ represents halogen, (C ₁ -C ₄ )-alkyl or (C ₁ -C ₄ ) -alkoxy.

The present invention especially provides compounds of general formula (I), wherein ^R represents phenyl, 2-fluorophenyl, 3-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2-bromo-6-fluorobenzene base, 2-ethylphenyl, 2-methoxyphenyl, 2-fluoro-3-methylphenyl, 2,3-dimethylphenyl, 2,4-difluorophenyl, 2,5 -Difluorophenyl, 2,4,5-trifluorophenyl, 3-chloro-2-fluorophenyl, 2-thienyl, 3-fluoro-2-thienyl, 3-bromo-2-thienyl, 3-Methyl-2-thienyl, 2-bromo-3-thienyl, 4-methyl-2-thienyl, 3-thienyl, 4-fluoro-3-thienyl, 2,4-dimethyl -3-thienyl, 3,5-dimethyl-1,2-oxazol-4-yl or 4-methylthiadiazol-5-yl, R ² represents hydrogen, fluorine, chlorine, bromine, methyl , ethyl, allyl, methoxy, ethoxy, methoxymethyl or cyclopropylmethyl, R ³ represents hydrogen, and R ⁴ represents hydrogen or mercapto.

The present invention more particularly provides compounds of general formula (I), wherein ^R represents phenyl, 2-fluorophenyl, 3-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2-methoxybenzene Base, 2-fluoro-3-methylphenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,4,5-trifluorophenyl, 3-chloro-2-fluorobenzene Base, 2-thienyl, 2-bromo-3-thienyl, 3-fluoro-2-thienyl, 3-bromo-2-thienyl, 3-methyl-2-thienyl, 4-methyl-2 -thienyl or 3-thienyl, R ² represents hydrogen, fluorine, bromine, methyl, ethyl, allyl, methoxy, ethoxy or cyclopropylmethyl, R ³ represents hydrogen, and R ⁴ Represents hydrogen or mercapto.

The definitions of the radicals listed above in general terms or preferred ranges apply to the end products of the general formula (I) and correspondingly to the starting materials or intermediates required for the preparation in each case. These group definitions can be combined with each other as needed, that is, combinations between predetermined preferred ranges are included.

Mainly for reasons of higher herbicidal activity, better selectivity and/or better producibility, the compounds of the above-mentioned general formula (I) of the present invention or their salts or their use according to the invention are of particular interest, Wherein individual groups have one of the preferred meanings specified or specified below, or especially one or more of the preferred meanings specified or specified below for those groups appear in combination.

With respect to the compounds of the present invention, the terms used above and further below are clarified. These terms are well known to those skilled in the art and have, inter alia, the definitions set forth below:

Unless defined differently, the designation of a chemical group is generally understood to mean the attachment to the backbone or other part of the molecule via the last-mentioned structural element, i.e. for example in the case of (C ₂ -C ₈ )-alkenyloxy Via an oxygen atom and in (C ₁ -C ₈ )-alkoxy-(C ₁ -C ₄ )-alkyl or (C ₁ -C ₈ )-alkoxycarbonyl-(C ₁ -C ₈ )-alk In the case of a group, each passes through a carbon atom of the alkyl group.

According to the invention, "alkylsulfonyl" (alone or as part of a chemical group) means a straight-chain or branched alkylsulfonyl group preferably having 1 to 8 or 1 to 6 carbon atoms, For example (but not limited to) (C ₁ -C ₆ )-alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethyl-sulfonyl, Butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutyl Sulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethyl-propylsulfonyl, 1,2-dimethylpropylsulfonyl base, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methyl-pentylsulfonyl, 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-methyl-propylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.

According to the invention, "alkylthio" (alone or as part of a chemical group) denotes a straight-chain or branched S-alkyl group, preferably having 1 to 8 or 1 to 6 carbon atoms, for example (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-dimethyl propylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3 -Methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethyl-butyl thiol, 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.

According to the present invention, unless defined differently elsewhere, "alkylsulfinyl (alkyl-S(=O)-)" means an alkyl group attached to the backbone via -S(=O)-, for example ( 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 Acyl groups such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl Sulfonyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylsulfinyl butylbutylsulfinyl, 3-methylbutyl-sulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2, 2-Dimethylpropylsulfinyl, 1-ethylpropyl-sulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethyl butylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2, 2-trimethylpropylsulfinyl, 1-ethyl-1-methyl-propylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.

"Alkoxy" means an alkyl group bonded through an oxygen atom, such as (but not limited to) (C ₁ -C ₆ )-alkoxy, such as methoxy, ethoxy, propoxy, 1-methyl Ethoxy, Butoxy, 1-Methylpropoxy, 2-Methylpropoxy, 1,1-Dimethylethoxy, Pentyloxy, 1-Methylbutoxy, 2-Methylpropoxy Methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethyl Propoxy, Hexyloxy, 1-Methylpentyloxy, 2-Methyl-pentyloxy, 3-Methylpentyloxy, 4-Methylpentyloxy, 1,1-Dimethylbutoxy base, 1,2-dimethylbutoxy, 1,3-dimethyl-butoxy, 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-methyl-propoxy. Alkenyloxy denotes an alkenyl group attached via an oxygen atom, and alkynyloxy denotes an alkynyl group attached via an oxygen atom, for example (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.

"Cycloalkoxy" means a cycloalkyl group attached through an oxygen atom and cycloalkenyloxy means a cycloalkenyl group attached through an oxygen atom.

According to the present invention, unless defined differently elsewhere, "alkylcarbonyl" (alkyl-C(=O)-) represents an alkyl group attached to the backbone via -C(=O)-, for example (C ₁ - C ₁₀ )-, (C ₁ -C ₆ )- or (C ₁ -C ₄ )-alkylcarbonyl. Here, the number of carbon atoms refers to the alkyl group in the alkylcarbonyl group.

Similarly, unless defined differently elsewhere, "alkenylcarbonyl" and "alkynylcarbonyl" in the present invention represent alkenyl and alkynyl respectively attached to the backbone via -C(=O)-, for example (C ₂ -C ₁₀ )-, (C ₂ -C ₆ )- or (C ₂ -C ₄ )-alkenylcarbonyl and (C ₂ -C ₁₀ )-, (C ₂ -C ₆ )- or (C ₂ -C ₄ )-Alkynylcarbonyl. Here, the number of carbon atoms refers to an alkenyl or alkynyl group in alkenylcarbonyl or alkynylcarbonyl.

Unless defined differently elsewhere, "alkoxycarbonyl (alkyl-OC(=O)-)" represents an alkyl group attached to the backbone via -OC(=O)-, for example (C ₁ -C ₁₀ ) -, (C ₁ -C ₆ )- or (C ₁ -C ₄ )-alkoxycarbonyl. Here, the number of carbon atoms refers to the alkyl group in the alkoxycarbonyl group. Similarly, unless defined differently elsewhere, "alkenyloxycarbonyl" and "alkynyloxycarbonyl" in the present invention represent alkenyl and alkynyl respectively attached to the backbone via OC(=O)-, for example (C ₂ -C ₁₀ )-, (C ₂ -C ₆ )- or (C ₂ -C ₄ )-alkenyloxycarbonyl and (C ₃ -C ₁₀ )-, (C ₃ -C ₆ )- or (C ₃ -C ₄ )-Alkynyloxycarbonyl. Here, the number of carbon atoms refers to an alkenyl or alkynyl group in alkenyloxycarbonyl or alkynyloxycarbonyl.

The term "aryl" denotes an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, especially 6 to 10, ring carbon atoms, for example phenyl, naphthyl, anthracenyl , phenanthrenyl and the like, preferably phenyl.

The term "optionally substituted aryl" also covers polycyclic ring systems such as tetrahydronaphthyl, indenyl, indenyl, fenyl, biphenyl, wherein the point of bonding is on the aromatic system. In systematic terminology, "aryl" is generally also encompassed by the term "optionally substituted phenyl". Preferred aryl substituents herein are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, aryl Alkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkane Oxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, dialkylamino- Alkoxy, Reference-[alkyl]silyl, Di-[alkyl]arylsilyl, Di-[alkyl]alkylsilyl, Reference-[alkyl]silylalkynyl, Arylalkynyl , heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxyl, nitro, cyano, amino, alkylamino, dialkyl Amine, alkylcarbonylamine, cycloalkylcarbonylamino, arylcarbonyl-amine, alkoxycarbonylamine, alkoxycarbonylalkylamine, arylalkoxycarbonylalkylamine, Hydroxy-carbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, di-alkyl-aminocarbonyl, heteroarylalkoxy, arylalkoxy.

A heterocyclic group (heterocyclyl) containing at least one heterocyclic ring (= carbocyclic ring in which at least one carbon atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P), which The ring system is saturated, unsaturated, partially saturated or heteroaromatic and can be unsubstituted or substituted (in which case the site of bonding is on a ring atom). If a heterocyclyl or heterocycle is optionally substituted, it may be fused to another carbocycle or heterocycle. In the case of optionally substituted heterocyclic groups, polycyclic ring 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 heterocyclyl also includes spiro ring systems, eg 1-oxa-5-aza-spiro[2.3]hexyl. Unless otherwise defined, heterocycles preferably contain 3 to 9 ring atoms, especially 3 to 6 ring atoms and in heterocycles contain one or more, preferably 1 to 4, especially 1, 2 or 3 A heteroatom preferably from the group N, O and S, however, two of the oxygen atoms must not be directly adjacent to each other, for example (with a 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-pyrrole-1-or-2-or-3-or- 4-or-5-yl; 2,5-dihydro-1H-pyrrol-1-or-2-or-3-yl, 1-or 2-or 3-or 4-hexahydropyridyl; 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- Base; 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-nitrogen-1-or-2-or-3-or-4-or-5-or-6-or-7-yl; 2,3,4,7 -Tetrahydro-1H-nitrogen-1-or-2-or-3-or-4-or-5-or-6-or-7-yl; 2,3,6,7-tetrahydro-1H- Nitrogen-1-or-2-or-3-or-4-yl; 3,4,5,6-tetrahydro-2H-nitrogen-2-or-3-or-4-or-5-or -6-or -7-yl; 4,5-dihydro-1H-nitrogen-1-or-2-or-3-or-4-yl; 2,5-dihydro-1H-nitrogen-1 -or-2-or-3-or-4-or-5-or-6-or-7-yl; 2,7-dihydro-1H-nitrogen-1-or-2-or-3-or -4-yl; 2,3-dihydro-1H-nitrogen-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 3,4-two Hydrogen-2H-nitrogen-2-or-3-or-4-or-5-or-6-or-7-yl; 3,6-dihydro-2H-nitrogen-2-or-3-or -4-or-5-or-6-or-7-yl; 5,6-dihydro-2H-nitrogen-2-or-3-or-4-or-5-or-6-or-7 -base; 4,5-dihydro-3H-nitrogen-2-or-3-or-4-or-5-or-6-or-7-yl; 1H-nitrogen-1-or-2- Or -3- or -4- or -5- or -6- or -7-yl; 2H-nitrogen -2- or -3- or -4- or -5- or -6- or -7-yl ; 3H-nitrogen-2-or-3-or-4-or-5-or-6-or-7-yl; 4H-nitrogen-2-or-3-or-4-or-5-or -6-or-7-yl, 2-or 3-oxolanyl (= 2- or 3-tetrahydrofuryl); 2,3-dihydrofuran-2-or-3-or-4-or-5 -yl; 2,5-dihydrofuran-2- or -3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4 -Dihydro-2H-pyran-2-or-3-or-4-or-5-or-6-yl; 3,6-dihydro-2H-pyran-2-or-3-or-4 -or-5-or-6-yl; 2H-pyran-2-or-3-or-4-or-5-or-6-yl; 4H-pyran-2-or-3-or-4 -yl, 2-or-3-or-4-oxepeptyl; 2,3,4,5-tetrahydroxane-2-or-3-or-4-or-5-or-6 -or-7-yl; 2,3,4,7-tetrahydroxyl-2-or-3-or-4-or-5-or-6-or-7-yl;2,3,6, 7-tetrahydro-oxo-2-or-3-or-4-yl; 2,3-dihydro-oxo-2-or-3-or-4-or-5-or-6-or-7 -yl; 4,5-dihydroxyl-2-or-3-or-4-yl; 2,5-dihydroxyl-2-or-3-or-4-or-5-or-6 - or -7-yl; Oxygen-2- or -3- or -4- or -5- or -6- or -7-yl; 2- or 3-tetrahydrothienyl; 2,3-dihydro Thiophene-2-or-3-or-4-or-5-yl; 2,5-dihydrothiophen-2-or-3-yl; tetrahydro-2H-thiopyran-2-or-3-or- 4-yl; 3,4-dihydro-2H-thiopyran-2-or-3-or-4-or-5-or-6-yl; 3,6-dihydro-2H-thiopyran-2- Or-3-or-4-or-5-or-6-yl; 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 heterocyclic ring systems (for example) 1- or 2-aziridinyl, oxiranyl, thiiridine, 1- or 2- or 3-azetidinyl, 2 - or 3-epoxypropylene, 2- or 3-thietanyl, 1,3-dioxiranyl-2-yl. Other examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic groups having two heteroatoms from the group of N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl ;4,5-dihydro-3H-pyrazol-3-or-4-or-5-yl; 4,5-dihydro-1H-pyrazole-1-or-3-or-4-or-5 -yl; 2,3-dihydro-1H-pyrazole-1-or-2-or-3-or-4-or-5-yl; 1-or-2-or-3-or-4-imidazole Pyridyl; 2,3-dihydro-1H-imidazol-1-or-2-or-3-or-4-yl; 2,5-dihydro-1H-imidazol-1-or-2-or-4 -or-5-yl; 4,5-dihydro-1H-imidazol-1-or-2-or-4-or-5-yl;hexahydropyridazine-1-or-2-or-3-or -4-yl; 1,2,3,4-tetrahydropyridazine-1- or -2- or -3- or -4- or -5- or -6-yl; 1,2,3,6- Tetrahydropyridazine-1-or-2-or-3-or-4-or-5-or-6-yl; 1,4,5,6-tetrahydropyridazine-1-or-3-or- 4-or-5-or-6-yl; 3,4,5,6-tetrahydropyridazine-3-or-4-or-5-yl; 4,5-dihydropyridazine-3-or- 4-yl; 3,4-dihydropyridazin-3-or-4-or-5-or-6-yl; 3,6-dihydropyridazin-3-or-4-yl; 1,6- Dihydropyridazin-1-or-3-or-4-or-5-or-6-yl; Hexahydropyrimidin-1-or-2-or-3-or-4-yl; 1,4,5 ,6-tetrahydro-pyrimidine-1-or-2-or-4-or-5-or-6-yl; 1,2,5,6-tetrahydropyrimidine-1-or-2-or-4- Or -5- or -6-yl; 1,2,3,4-tetrahydropyrimidin-1- or -2- or -3- or -4- or -5- or -6-yl; 1,6- Dihydropyrimidine-1-or-2-or-4-or-5-or-6-yl; 1,2-dihydropyrimidine-1-or-2-or-4-or-5-or-6- 2,5-dihydropyrimidin-2-or-4-or-5-yl; 4,5-dihydropyrimidin-4-or-5-or-6-yl; 1,4-dihydro-pyrimidine -1- or -2- or -4- or -5- or -6-yl; 1- or -2- or -3-hexahydropyrazinyl; 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-dihydropyrazin-2-or-3-or-5-or-6-yl; 2,5-dihydropyrazin-2-or-3-yl;1 ,3-dioxol-2-or-4-or-5-yl; 1,3-dioxol-2-or-4-yl; 1,3-dioxane- 2-or-4-or-5-yl; 4H-1,3-dioxine-2-or-4-or-5-or-6-yl; 1,4-dioxane-2 -or-3-or-5-or-6-yl; 2,3-dihydro-1,4-dioxine-2-or-3-or-5-or-6-yl; 1 ,4-Dioxin-2-or-3-yl; 1,2-dithiol-3-or-4-yl; 3H-1,2-dithiol-3-or-4- Or-5-yl; 1,3-dithiol-2-or-4-yl; 1,3-dithiol-2-or-4-yl; 1,2-dithian-3-or- 4-yl; 3,4-dihydro-1,2-dithiene-3-or-4-or-5-or-6-yl; 3,6-dihydro-1,2-dithiene- 3- or -4-yl; 1,2-dithian-3- or -4-yl; 1,3-dithian-2- or -4- or -5-yl; 4H-1,3- Dithienyl-2-or-4-or-5-or-6-yl; Isoxazolidine-2-or-3-or-4-or-5-yl; 2,3-dihydroisoxazole -2- or -3- or -4- or -5-yl; 2,5-dihydroisoxazol-2- or -3- or -4- or -5-yl; 4,5-dihydroiso Oxazol-3- or -4- or -5-yl; 1,3-oxazolidine-2- or -3- or -4- or -5-yl; 2,3-dihydro-1,3- Oxazol-2- or -3- or -4- or -5-yl; 2,5-dihydro-1,3-oxazol-2- or -4- or -5-yl; 4,5-di Hydrogen-1,3-oxazol-2-or-4-or-5-yl; 1,2-oxazolane-2-or-3-or-4-or-5-or-6-yl;3 ,4-dihydro-2H-1,2-oxazine-2-or-3-or-4-or-5-or-6-yl; 3,6-dihydro-2H-1,2-oxazine -2-or-3-or-4-or-5-or-6-yl; 5,6-dihydro-2H-1,2-oxazine-2-or-3-or-4-or-5 -or-6-yl; 5,6-dihydro-4H-1,2-oxazin-3-or-4-or-5-or-6-yl; 2H-1,2-oxazin-2- Or -3-or -4-or -5-or -6-yl; 6H-1,2-oxazin-3-or-4-or-5-or-6-yl; 4H-1,2-oxa oxazin-3-or-4-or-5-or-6-yl; 1,3-oxane-2-or-3-or-4-or-5-or-6-yl;3,4- Dihydro-2H-1,3-oxazin-2-or-3-or-4-or-5-or-6-yl; 3,6-dihydro-2H-1,3-oxazin-2- Or -3-or-4-or-5-or-6-yl; 5,6-dihydro-2H-1,3-oxazin-2-or-4-or-5-or-6-yl; 5,6-dihydro-4H-1,3-oxazin-2-or-4-or-5-or-6-yl; 2H-1,3-oxazin-2-or-4-or-5 -or-6-yl; 6H-1,3-oxazin-2-or-4-or-5-or-6-yl; 4H-1,3-oxazin-2-or-4-or-5 -or-6-yl; morpholin-2-or-3-or-4-yl; 3,4-dihydro-2H-1,4-oxazin-2-or-3-or-4-or- 5-or-6-yl; 3,6-dihydro-2H-1,4-oxazin-2-or-3-or-5-or-6-yl; 2H-1,4-oxazin-2 -or-3-or-5-or-6-yl; 4H-1,4-oxazin-2-or-3-yl; 1,2-oxazepane-2-or-3-or -4- or -5- or -6- or -7-yl; 2,3,4,5-tetrahydro-1,2-oxazone-2- or -3- or -4- or -5- Or -6-or -7-yl; 2,3,4,7-tetrahydro-1,2-oxazone-2-or-3-or-4-or-5-or-6-or-7 -yl; 2,3,6,7-tetrahydro-1,2-oxaza-2- or -3- or -4- or -5- or -6- or -7-yl; 2,5, 6,7-tetrahydro-1,2-oxaza-2-or-3-or-4-or-5-or-6-or-7-yl; 4,5,6,7-tetrahydro- 1,2-oxazapine-3-or-4-or-5-or-6-or-7-yl; 2,3-dihydro-1,2-oxazapine-2-or-3-or -4- or -5- or -6- or -7-yl; 2,5-dihydro-1,2-oxazone-2- or -3- or -4- or -5- or -6- Or -7-yl; 2,7-dihydro-1,2-oxaza-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-two Hydrogen-1,2-oxazapine-3-or-4-or-5-or-6-or-7-yl; 4,7-dihydro-1,2-oxazapine-3-or-4 -or-5-or-6-or-7-yl; 6,7-dihydro-1,2-oxaza-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-oxazone-2- or -3- or -4- or -5- or -6- Or -7-yl; 2,3,4,7-tetrahydro-1,3-oxaza-2- or -3- or -4- or -5- or -6- or -7-yl; 2 ,3,6,7-tetrahydro-1,3-oxaza-2-or-3-or-4-or-5-or-6-or-7-yl; 2,5,6,7- Tetrahydro-1,3-oxazapine-2-or-4-or-5-or-6-or-7-yl; 4,5,6,7-tetrahydro-1,3-oxazapine- 2-or-4-or-5-or-6-or-7-yl; 2,3-dihydro-1,3-oxazone-2-or-3-or-4-or-5-or -6- or -7-yl; 2,5-dihydro-1,3-oxaza-2- or -4- or -5- or -6- or -7-yl; 2,7-dihydro -1,3-oxazone-2-or-4-or-5-or-6-or-7-yl; 4,5-dihydro-1,3-oxazone-2-or-4- Or -5- or -6- or -7-yl; 4,7-dihydro-1,3-oxaza-2- or -4- or -5- or -6- or -7-yl; 6 ,7-dihydro-1,3-oxaza-2-or-4-or-5-or-6-or-7-yl; 1,3-oxaza-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-oxazizane-2-or-3-or-4-or-5-or-6-or-7-yl; 2,3,4,7-tetrahydro-1,4 -Oxazapine-2-or-3-or-4-or-5-or-6-or-7-yl; 2,3,6,7-tetrahydro-1,4-oxazapine-2- Or -3-or-5-or-6-or-7-yl; 2,5,6,7-tetrahydro-1,4-oxaza-2-or-3-or-5-or-6 -or-7-yl; 4,5,6,7-tetrahydro-1,4-oxaza-2-or-3-or-4-or-5-or-6-or-7-yl; 2,3-dihydro-1,4-oxaza-2-or-3-or-5-or-6-or-7-yl; 2,5-dihydro-1,4-oxaza- 2-or-3-or-5-or-6-or-7-yl; 2,7-dihydro-1,4-oxazone-2-or-3-or-5-or-6-or -7-yl; 4,5-dihydro-1,4-oxaza-2- or -3- or -4- or -5- or -6- or -7-yl; 4,7-dihydro -1,4-oxazone-2-or-3-or-4-or-5-or-6-or-7-yl; 6,7-dihydro-1,4-oxazone-2- Or -3- or -5- or -6- or -7-yl; 1,4-oxaza-2- or -3- or -5- or -6- or -7-yl; Isothiazolidine- 2-or-3-or-4-or-5-yl; 2,3-dihydroisothiazol-2-or-3-or-4-or-5-yl;2,5-dihydroisothiazole- 2- or -3- or -4- or -5-yl; 4,5-dihydroisothiazol-3- or -4- or -5-yl; 1,3-thiazolidine-2- or -3- Or -4-or -5-yl; 2,3-dihydro-1,3-thiazol-2-or-3-or-4-or-5-yl; 2,5-dihydro-1,3- Thiazol-2-or-4-or-5-yl; 4,5-dihydro-1,3-thiazol-2-or-4-or-5-yl; 1,3-thiazinane-2-or -3-or-4-or-5-or-6-yl; 3,4-dihydro-2H-1,3-thiazine-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-thiazine-2-or-4-or-5-or-6-yl; 5,6-dihydro-4H-1,3-thiazine-2-or-4-or-5-or-6 -yl; 2H-1,3-thiazine-2-or-4-or-5-or-6-yl; 6H-1,3-thiazine-2-or-4-or-5-or-6 -yl; 4H-1,3-thiazin-2-or-4-or-5-or-6-yl. Other examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic groups having 3 heteroatoms from the group of N, O and S, such as 1,4,2-dioxazolidine-2- or - 3-or-5-yl; 1,4,2-dioxazol-3-or-5-yl; 1,4,2-dioxazolane-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-dioxazapine-3-or-5-or-6-or-7-yl; 2,3-dihydro-7H-1,4,2-dioxazapine-2-or-3- Or -5-or -6-or -7-yl; 2,3-dihydro-5H-1,4,2-dioxazone-2-or-3-or-5-or-6-or- 7-yl; 5H-1,4,2-dioxazapine-3-or-5-or-6-or-7-yl; 7H-1,4,2-dioxazapine-3-or- 5-or-6-or-7-yl. Structural examples of further optionally substituted heterocycles are also listed below: .

The heterocycles listed above are preferably substituted by, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkane radical, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl , heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl , alkynyl, alkynylalkyl, alkylalkynyl, paraalkylsilylalkynyl, nitro, amine, cyano, haloalkoxy, haloalkylthio, alkylthio, mercapto, hydroxyalkyl , pendant oxy, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclicthio, heteroaryloxy, di Alkylamino, Alkylamino, Cycloalkylamino, Hydroxycarbonylalkylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonyl-Alkylamino, Alkoxycarbonylalkyl (Alkyl)amino, aminocarbonyl, alkylaminocarbonyl, dialkylamino-carbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkyl-aminocarbonyl , Arylalkoxycarbonylalkylaminocarbonyl.

When the base structure is substituted by "one or more substituents" from the list of radicals (=group) or generally defined radical groups, this includes in each case at the same time a plurality of identical and/or structurally different group substitution.

In the case of partially or fully saturated nitrogen heterocycles, this group can be attached to the rest of the molecule via carbon or via nitrogen.

Suitable substituents for substituted heterocyclic groups are the substituents otherwise specified below, and additionally also pendant oxy and pendant thio. A pendant oxy group as a substituent on a ring carbon atom is then, for example, a carbonyl group in a heterocycle. Therefore, lactones and lactams are preferably also included. Pendant oxy groups can also be present on ring heteroatoms, which can exist in different oxidation states (for example in the case of N and S), and in which case they form in the heterocycle, for example, the divalent group -N( O)-, -S(O)- (also abbreviated as SO) and -S(O) ₂ - (also abbreviated as SO ₂ ). In the case of -N(O)- and -S(O)- groups, both enantiomers in each case are included.

According to the present invention, the expression "heteroaryl" means a heteroaromatic compound, i.e. a fully unsaturated aromatic heterocyclic compound, preferably having 1 to 4, preferably 1 or 2 identical or different heteroatoms , preferably a 5 to 7 membered ring of O, S or N. Inventive heteroaryl systems (eg) 1H-pyrrol-1-yl, 1H-pyrrol-2-yl, 1H-pyrrol-3-yl, furan-2-yl, furan-3-yl, thiophen-2-yl , Thiophene-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-triazole -4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4 -Oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl , 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, azinyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl , pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-3-yl, pyrazin-4-yl, 1,3 ,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1 ,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2, 6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl Base, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl, 1,3-thiazole- 4-yl, 1,3-thiazol-5-yl, oxyxyl, thioxyl, 1,2,4-triazolone and 1,2,4-diazoxyl, 2H-1,2, 3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3, 4-thiatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl. The heteroaryl groups of the present invention may also be substituted by one or more of the same or different groups. If two adjacent carbon atoms are part of another aromatic ring, the system is a fused heteroaromatic system, eg benzo-fused or polyannealed heteroaromatics. A preferred example is quinoline (such as quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6 -yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; phenoline; 1,5-naphthyridine; 1,6-naphthyridine; Pyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; pyridopyrazine; pyridopyrimidine; pyridopyrazine; pteridine; pyrimidopyrimidine. Examples of heteroaryl are also 5- or 6-membered benzofused rings from the following groups: 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-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-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-benzimidazole-1-yl, 1H-benzimidazole-2 -yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H-benzimidazol-7-yl, 1,3-benzox Azol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzene Oxazol-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzo Thiazol-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 -base.

The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. If the term is applied to a group, "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom.

According to the invention, "alkyl" denotes a straight-chain or branched open-chain, saturated hydrocarbon group, which is optionally mono- 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, especially methoxy, methyl, fluoroalkyl, cyano , nitro, fluorine, chlorine, bromine or iodine.

The prefix "two" includes combinations of the same or different alkyl groups, such as dimethyl or methyl (ethyl) or ethyl (methyl).

"Haloalkyl", "haloalkenyl" and "haloalkynyl" respectively represent alkyl, alkenyl and alkynyl partially or completely substituted by the same or different halogen atoms, such as monohaloalkyl, such as CH ₂ CH ₂ Cl, _CH2CH2Br , _CHClCH3 , _CH2Cl , _CH2F ; perhaloalkyl, such as _{CCl3 , CCIF2} , _{CFCl2 , CF2CCIF2 , CF2CClFCF3} ; polyhaloalkyl, such as _CH2 CHFCl, _CF2CCIFH , _CF2CBrFH , _CH2CF3 ; _the term perhaloalkyl also encompasses the term perfluoroalkyl.

"Haloalkoxy" means, for example, OCF ₃ , OCHF ₂ , OCH ₂ F, OCF ₂ CF ₃ , OCH ₂ CF ₃ and OCH ₂ CH ₂ Cl; this definition applies correspondingly to haloalkenyl and other halogen substituents group.

The expression "(C ₁ -C ₄ )-alkyl" referred to herein is, for example, a shorthand notation for straight-chain or branched-chain alkyl groups having from 1 to 4 carbon atoms according to the range stated for the carbon atoms , that is to say methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. Typical alkyl groups having a larger number of carbon atoms (eg "(C ₁ -C ₆ )-alkyl") correspondingly also cover straight-chain or branched chain alkyl groups having a larger number of carbon atoms, ie according to the examples Also alkyl groups having 5 and 6 carbon atoms.

Unless specifically stated otherwise, in the case of hydrocarbyl groups such as alkyl, alkenyl and alkynyl groups (including those included in composite groups), those preferably have, for example, 1 to 6 carbon atoms or have 2 to 6 carbon atoms. carbon atoms (in the case of unsaturated groups) of the lower carbon skeleton. Alkyl (contained in complex groups such as alkoxy, haloalkyl, etc.) is, for example, methyl, ethyl, n- or i-propyl, n-, i-, tert- or 2-butanyl base, 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 are defined as possibly unsaturated radicals corresponding to alkyl in which at least one double or triple bond is present. Preferred are groups having one double bond or triple bond.

The term "alkenyl" also especially includes straight-chain or branched open-chain hydrocarbon groups having more than one double bond (such as 1,3-butadienyl and 1,4-pentadienyl), but also includes Allenyl or accumulated polyenyl with one or more accumulated double bonds (such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentadienyl alkenyl). Alkenyl denotes, for example, vinyl optionally substituted by other alkyl groups, such as (but not limited to) (C ₂ -C ₆ )-alkenyl, for example vinyl, 1-propenyl, 2-propenyl, 1-propenyl Methyl vinyl, 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 Alkenyl, 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 Base-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl Base, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl -3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl , 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl -2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2 -butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl Base-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butene Base, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2- Methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term "alkynyl" also especially includes straight-chain or branched open-chain hydrocarbon groups having more than one triple bond or having one or more triple bonds and one or more double bonds, such as 1,3-butatrienyl or 3-penten-1-yn-1-yl. (C ₂ -C ₆ )-Alkynyl means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methynyl Base-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 Alkynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl Base-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl Base-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.

The term "cycloalkyl" denotes a carbocyclic saturated ring system having preferably 3 to 8 ring carbon atoms (e.g. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl), which is optionally further preferably composed of Hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amine, alkylamino, dialkylamino, alkoxy Substituted by alkylcarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl groups, ring systems with substituents are included, and substituents with double bonds on cycloalkyl groups are also included, for example alkylene (eg methylene). In the case of optionally substituted cycloalkyl groups, polycyclic aliphatic systems are also included, such as bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[ 2.1.0]pentane-1-yl, bicyclo[1.1.1]pentane-1-yl, bicyclo[2.1.0]pentane-2-yl, bicyclo[2.1.0]pentane-5-yl, Bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octane-2-yl, bicyclo[3.2.1]octane-2-yl, bicyclo[3.2. 2] Nonan-2-yl, adamantan-1-yl and adamantan-2-yl, and also include such as 1,1'-bis(cyclopropyl)-1-yl, 1,1'-bis( Cyclopropyl)-2-yl and other systems. The term "(C ₃ -C ₇ )-cycloalkyl" is a shorthand notation for a cycloalkyl group having 3 to 7 carbon atoms corresponding to the specified carbon atom range.

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

"Cycloalkenyl" means a carbocyclic, non-aromatic, partially unsaturated ring system having preferably 4-8 carbon atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentyl Alkenyl, 2-cyclopentenyl, 3-cyclopentenyl or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1 ,4-Cyclohexa-dienyl also contains a substituent with a double bond in the cycloalkenyl, such as an alkylene group (eg, methylene). In the case of optionally substituted cycloalkenyl, the interpretations for substituted cycloalkyl apply correspondingly.

According to the present 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 1 to 6 carbon atoms, For example (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.

"Halocycloalkyl" and "halocycloalkenyl" respectively mean partially or completely composed of the same or different halogen atoms (such as F, Cl and Br) or haloalkyl (such as trifluoromethyl or difluoromethyl) ) substituted cycloalkyl and cycloalkenyl, such as 1-fluorocycloprop-1-yl, 2-fluoro-cycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclopropan-1-yl, But-1-yl, 1-trifluoromethylcyclopropan-1-yl, 2-trifluoromethylcyclopropan-1-yl, 1-chlorocyclopropan-1-yl, 2-chlorocyclopropan-1- base, 2,2-dichlorocyclopropan-1-yl, 3,3-difluorocyclobutyl.

According to the invention, "trialkylsilyl" (by itself or as part of a chemical group) represents a straight-chain or branched Si-alkane, preferably having 1 to 8 or 1 to 6 carbon atoms. group, such as tri[(C ₁ -C ₈ )-, (C ₁ -C ₆ )- or (C ₁ -C ₄ )-alkyl]silyl, such as (but not limited to) trimethylsilyl, trimethylsilyl, Ethylsilyl, tri(n-propyl)silyl, tri(isopropyl)silyl, tri(n-butyl)silyl, tri(1-methylprop-1-yl)silyl, tri(2 -methylprop-1-yl)silyl, tris(1,1-dimethyleth-1-yl)silyl, tris(2,2-dimethyleth-1-yl)silyl.

If a compound can form, via hydrogen displacement, tautomers whose structures are not formally covered by general formula (I), these tautomers are still covered by the definition of inventive compounds of general formula (I), unless it is considered specific tautomers. For example, many carbonyl compounds can exist in the keto form as well as in the enol form, both forms being covered by the definition of compounds of general formula (I).

Depending on the nature of the substituents and their mode of attachment, the compounds of general formula (I) may exist in the form of stereoisomers. The general formula (I) covers all possible stereoisomers defined according to specific three-dimensional forms, such as enantiomers, diastereomers, Z and E isomers. If, for example, one or more alkenyl groups are present, diastereoisomers (Z and E isomers) may occur. Enantiomers and diastereomers may occur if, for example, one or more asymmetric carbon atoms are present. Stereoisomers may be obtained from mixtures obtained by preparation by usual separation methods. Chromatographic separations can be accomplished on an analytical scale to find enantiomeric or diastereomeric excesses, or on a preparative scale to generate test samples for biological assays. Stereoisomers can likewise be prepared selectively by employing stereoselective reactions and using optically active starting materials and/or auxiliaries. The invention thus also relates to all stereoisomers covered by general formula (I) but not shown in their specific stereoisomeric forms and mixtures thereof.

If the compound is obtained in solid form, purification by recrystallization or digestion is also possible. If individual compounds of general formula (I) cannot be obtained in a satisfactory manner by the routes described below, they can be prepared by derivatizing other compounds of general formula (I).

Suitable separation methods, purification methods and methods for the separation of stereoisomers of the compounds of general formula (I) are methods generally known to the person skilled in the art from analogous situations, for example by physical processes such as crystallization, chromatographic methods, especially tube column chromatography and HPLC (high pressure liquid chromatography), distillation (under reduced pressure as appropriate), extraction and other methods), any remaining mixture. Processes suitable for preparative quantities or on an industrial scale use, for example, optically active acids and, if appropriate (provided the presence of acidic groups) optically active bases to render, for example, diastereomeric diastereomers obtainable from mixtures of diastereoisomers. Isomer salt crystallization.

Synthesis of substituted thiazolopyridines of general formula (I).

The substituted thiazolopyridines of general formula (I) of the present invention can be prepared using known procedures. The synthetic routes used and tested start with either commercially available or readily synthesized substituted thiazoles or substituted pyridines. In the following reaction schemes, the radicals R ¹ , R ² , R ³ and R ⁴ of the general formula (I) have the meanings defined above, unless an exemplary but non-limiting definition is given. A first synthetic route to substituted thiazolopyridines of general formula (I) proceeds via optionally substituted Boc-protected aminothiazoles (II) (Scheme 1). For this, the substituted carboxylateaminothiazole is protected (e.g. with _Boc2O and DMAP = 4-dimethylaminopyridine, where Boc = tert-butyloxycarbonyl) and then treated with a suitable affinity Reduction of a nuclear reagent such as lithium aluminum hydride or methylmagnesium chloride to the corresponding alcohol (IV). Subsequent oxidation of the alcohol to the corresponding carbonyl using a suitable oxidizing agent such as manganese dioxide affords the optionally substituted Boc-protected aminothiazole (V). In order to complete the synthesis of compounds of general formula (I), optionally substituted aminothiazoles (V) protected by Boc and optionally substituted phosphonium salts (refer to Org. Lett. , 1999 , 1 , 1579-1581 ) in the presence of a base (e.g. potassium tert-butoxide) followed by acid-mediated Boc removal under acidic conditions (e.g. TFA = trifluoroacetic acid) in a suitable polar-aprotic solvent (e.g. dichloromethane) Protection and cyclization (refer to Org. Lett. , 2016 , 18 , 1562-1565). During the synthesis of compound (VII), the corresponding trans and cis isomers and mixtures of isomers in different ratios can be isolated. In Reaction Scheme 1 below, ^R1 has the meaning defined above. R ² , R ³ and R ⁴ , for example but not limited to, represent hydrogen.

Reaction Scheme 1. Alternatively, the synthesis of substituted thiazolopyridines of general formula (I) can be accomplished via a Friedländer style reaction of substituted aminothiazoles (VIII) with substituted ketones (Reaction Figure 2). Following this method, deprotection of Boc-protected thiazoles (V) in the presence of weak acids in suitable solvents such as silica gel and EtOAc, where Boc = tert-butyloxycarbonyl, affords substituted aminothiazoles ( VIII). This compound is then subjected to a cyclization reaction with a substituted ketone in the presence of a suitable base such as potassium hydroxide in a suitable solvent such as methanol to provide compounds of general formula (I) (cf. US1998/5723413). In Reaction Scheme 2 below, R ¹ and R ² have the meanings defined above. R ³ and R ⁴ (for example but not limited to) represent hydrogen.

Scheme 2. Substituted thiazolopyridines of general formula (I) can also be synthesized from substituted hydroxypyridines (Scheme 3). Using this method, a substituted hydroxypyridine (X) is nitrated (for example with sulfuric and nitric acids) and then palladium-catalyzed cross-coupling reaction using a suitable palladium complex (for example Pd(dppf)Cl ₂ ), an appropriate base ( such as potassium carbonate) and a suitable aprotic solvent such as toluene, 1,4-dioxane or DME=dimethoxyethane) to acid (refer to WO2015/123133). Then the free hydroxyl group of compound (XIII) is reacted with N , N -dimethylthiocarbamoyl chloride in the presence of a suitable base (for example DBU=1,8-diazabicycloundec-7-ene), Subsequent Newmann-quart rearrangement facilitated by heating in a suitable solvent (eg, xylene) to provide pyridine (XV) (cf. Bioorg. Med. Chem. , 2013 , 21 , 6804- 6820). Reduction of the nitro group to the amine group in the presence of a suitable reagent system such as iron powder and ammonium chloride followed by removal of the formamide group affords the disulfide (XVII). Reagents that can achieve formamide deprotection include mixtures of potassium hydroxide, lithium hydroxide and lithium aluminum hydride (refer to Chem. Eur. J. , 2018 , 24 , 4864-487; WO2016/120403). Finally, a cyclization using an appropriate reaction partner (e.g. triethyl orthoformate) in the presence of a suitable acid catalyst (e.g. p -TsOH = p-toluenesulfonic acid) completes the synthetic route to give the compound of general formula (I) (Refer to WO2018/203235). In Reaction Scheme 3 below, R ¹ , R ² and R ³ have the meanings defined above and X=halogen. R ⁴ , by way of example and without limitation, represents hydrogen.

Reaction Scheme 3. The synthesis of substituted thiazolopyridines of general formula (I) is further illustrated starting from substituted aminopyridines (Reaction Scheme 4). For this, a palladium-catalyzed cross-coupling reaction uses a suitable palladium complex (such as Pd(dppf)Cl ₂ ), a suitable base (such as potassium carbonate) and a suitable aprotic solvent (such as toluene, 1,4-dioxane or DME = dimethoxyethane) to couple the halide aminopyridine (XIX) to acid. The resulting product (XX) is then dihalogenated using an appropriate reagent (eg NBS= N -bromosuccinimide or NCS= N -chlorosuccinimide) in a polar solvent such as acetonitrile to provide compound (XXI). The cyclization reaction is then carried out using potassium ethyl xanthate at high temperature in a suitable solvent (such as DMF = N , N -dimethylformamide) to synthesize bicyclic rings (Ia, R ² = Br, R ⁴ = SH). Reduction of this compound using a metal such as Zn or Fe in a protic solvent such as an organic acid such as acetic acid or in a mixture containing a protic reagent yields an unsubstituted thiazolo moiety (I, R ⁴ =H). Alternatively, alkylation of the sulfur atom is carried out using an alkylating agent (e.g. iodomethane) in the presence of a suitable base (e.g. potassium carbonate) followed by a suitable oxidizing reagent (e.g. m -CPBA = m-chloroperbenzoic acid) Oxidation to provide sulfide (Ic, R ² = Br, R ⁴ = SO ₂ Me) (cf. WO2017/9806; WO2006/53166). Displacement of the phenyl group using a suitable nucleophile (eg sodium borohydride) followed by an appropriate palladium complex (eg Pd(dppf)Cl ₂ ), a suitable base (eg potassium carbonate) and a suitable aprotic solvent (eg toluene, 1, 4-dioxane or DME = dimethoxyethane) to Acids undergo a palladium cross-coupling reaction to provide compounds of general formula (I). In Reaction Scheme 4 below, ^R1 and ^R2 have the meanings defined above. R ³ and R ⁴ (for example but not limited to) represent hydrogen.

Scheme 4. Substituted thiazolopyridines of general formula (I) can also be synthesized via cyclization of substituted ketoenamines and substituted aminothiazoles (Scheme 5). Following this synthetic route, ketones (IX) are treated at reflux with suitable reagents such as N , N -dimethylformamide dimethyl acetal to afford substituted ketoenamines (XXIII). Subsequent cyclization of ketoenamines (XXIII) and substituted aminothiazoles (XXIV) under acidic conditions using a suitable co-solvent such as HCl in 1,4-dioxane provides the general formula (I ) compounds. In Reaction Scheme 5 below, R ¹ and R ² have the meanings defined above. R ³ and R ⁴ (for example but not limited to) represent hydrogen.

Reaction Scheme 5 Selected detailed synthetic examples of compounds of general formula (I) of the present invention are given below. The numbering of the examples mentioned corresponds to the numbering scheme in Reaction Schemes 1 to 5 and Table 1. ¹ H NMR spectroscopy data reported for the chemical examples set forth in the following sections were performed on a Bruker instrument at 600 MHz, 400 MHz or 300 MHz using _CDCl3 or _d6 -DMSO as solvent and tetramethylsilane (δ = 0.00 ppm) was obtained as an internal standard. The listed symbols have the meaning given below: br = broad; s = singlet, d = doublet, t = triplet, dd = doublet of doublets, ddd = doublet (doublet of doublets), m = multiplet peak, q = quartet, qu = quintet, sext = sext, sept = septet, dq = double quartet, dt = double triplet.

Synthetic example: No. XXa: 6-(2-fluoro-3-chlorophenyl)pyridin-2-amine At room temperature, to 6-bromopyridin-2-amine (10.00 g, 56.88 mmol, 1.00 equivalent), 2-fluoro-3-chlorophenyl A stirred mixture of acid (11.86 g, 65.98 mmol, 1.16 equiv) and Na ₂ CO ₃ (12.06 g, 113.76 mmol, 2.00 equiv) in 1,4-dioxane (70 mL) and water (70 mL) To the mixture was added Pd(dppf) _Cl2 (1.67 g, 2.28 mmol, 0.04 equiv). The resulting mixture was stirred at 80 °C for 3 h. The reaction mixture was cooled to room temperature, diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous _Na2SO4 , filtered and concentrated under reduced pressure _. The remaining residue was purified by flash column chromatography on silica gel eluting with hexane/EtOAc (gradient) to provide compound XXa (10.12 g, 80% yield). ¹ H NMR (400 MHz, CDCl ₃ ): δ _H 7.81-7.77 (m, 1H), 7.54-7.50 (dd, 1H), 7.42-7.38 (m, 1H), 7.18-7.11 (m, 2H), 6.52 -6.50 (d, 1H), 4.59-4.45 (br. s, 2H).

No. XXIa: 3,5-Dibromo-6-(2-fluoro-3-chlorophenyl)pyridin-2-amine To a stirred solution of compound XXa (10.12 g, 45, 45 mmol, 1.0 equiv) in acetonitrile (140 mL) was carefully added N -bromosuccinimide (17.79 g, 99.99 mmol, 2.2 equiv. ). The resulting mixture was warmed to room temperature and stirred for 4 h. The reaction mixture was diluted with water and the resulting solid was removed by filtration, washed with water and then dried under reduced pressure to afford Compound XXIa (16.75 g, 95% yield) as a dark orange solid. ¹ H NMR (400 MHz, CDCl ₃ ): δ _H 7.93 (s, 1H), 7.48-7.45 (m, 1H), 7.28-7.24 (m, 1H), 7.19-7.15 (m, 1H), 5.10-5.00 (br. s, 2H).

No. Ia: 6-bromo-5-(2-fluoro-3-chlorophenyl)[1,3]thiazolo[4,5-b]pyridine-2-thiol To a stirred solution of compound XXIa (16.75 g, 44.03 mmol, 1.0 equiv) in DMF (120 mL) was added O-ethyldithiocarbonate potassium salt (16.01 g, 97 mmol, 2.2 equivalent). The resulting mixture was heated at reflux for 9 h. The reaction mixture was cooled to room temperature, poured onto ice water and acidified using 2 N HCl. The resulting precipitate was filtered, washed with water and then dried under reduced pressure to provide Compound Ia (15.76 g, 95% yield). ¹ H NMR (400 MHz, CDCl ₃ ): δ _H 9.78 (br. s, 1H), 8.02 (s, 1H), 7.54-7.51 (m, 1H), 7.31-7.15 (m, 2H).

I-029: 6-Bromo-5-(2-fluoro-3-chlorophenyl)[1,3]thiazolo[4,5-b]pyridine To a stirred solution of Compound la (15.76 g, 39.85 mmol, 1.0 equiv) in acetic acid (130 mL) was added iron powder (33.39 g, 597.82 mmol, 15 equiv) carefully in portions at room temperature. The resulting reaction mixture was stirred at 100 °C for 5.5 h. The reaction mixture was cooled to 60 °C and iron powder was removed by filtration. The filtrate was diluted with water and the resulting precipitate was isolated by filtration, washed with water. _The filter cake was dissolved in _CH2Cl2 and then washed with water. The organic layer was dried over anhydrous MgSO ₄ , filtered and dried under reduced pressure. The resulting residue was purified via flash column chromatography on silica gel eluting with hexane/EtOAc (gradient) to provide compound 1-029 (4.13 g, 30% yield).

I-031: 5-(2-Fluoro-3-chlorophenyl)-6-methyl-[1,3]thiazolo[4,5-b]pyridine At room temperature and under an argon atmosphere, compound I-029 (2.87 g, 6.27 mmol, 1.0 equivalents), methyl To a stirred mixture of acid (1.55 g, 25.06 mmol, 4.0 equiv) and potassium phosphate (2.66 g, 12.53 mmol, 2.0 equiv) in anhydrous PhMe (60 mL) was added palladium(II) acetate (141 mg, 0.63 mmol, 0.1 equiv) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (795 mg, 1.88 mmol, 0.3 equiv). The resulting mixture was stirred at reflux for 3.5 h. The reaction mixture was cooled to room temperature, diluted with water (100 mL) and PhMe (20 mL), followed by the addition of ammonium pyrrolidine dithiocarbamate (451 mg, 2.75 mmol, 0.44 equiv). The mixture was stirred at room temperature for 1 h, the organic layer was washed with saturated aqueous NaHCO ₃ , dried over anhydrous MgSO ₄ , filtered and concentrated under reduced pressure.

The resulting residue was purified via flash column chromatography on silica gel eluting with hexane/EtOAc (gradient) to provide compound 1-031 (765 mg, 43% yield).

No. XXb: 6-(2-Ethylphenyl)pyridin-2-amine At room temperature, to 6-bromopyridin-2-amine (6.00 g, 34.13 mmol, 1.00 equivalent), 2-ethylphenyl A stirred mixture of acid (10.55 g, 68.26 mmol, 2.00 eq) and Na ₂ CO ₃ (9.43 g, 68.26 mmol, 2.00 eq) in 1,4-dioxane (60 mL) and water (60 mL) To the mixture was added Pd(dppf) _Cl2 (1.25 g, 1.71 mmol, 0.05 equiv). The resulting mixture was stirred at 80 °C for 2 h. The reaction mixture was diluted with water and extracted well with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous _Na2SO4 , filtered and concentrated under reduced pressure _. The resulting residue was purified via flash column chromatography on silica gel eluting with hexane/EtOAc (gradient) to provide compound XXb (4.59 g, 68% yield). ¹ H NMR (400 MHz, CDCl ₃ ): δ _H 7.50-7.47 (m, 1H), 7.33-7.21 (m, 4H), 6.73-6.71 (d, 1H), 6.48-6.46 (d, 1H), 4.50 -4.41 (br. s, 2H), 2.75-2.69 (q, 2H), 1.14-1.10 (t, 3H).

No. XXIb: 3,5-dibromo-6-(2-ethylphenyl)pyridin-2-amine To a stirred solution of compound XXb (4.59 g, 22.46 mmol, 1.0 equiv) in MeCN (140 mL) was added N-bromosuccinimide (8.79 g, 49.40 mmol, 2.2 equiv) carefully at 0 °C. The resulting mixture was warmed to room temperature and stirred for 4 h. The reaction mixture was diluted with water and the resulting solid was removed by filtration. The filtered solid was washed well with water and dried to afford compound XXIb (6.35 g, 79% yield) as a light orange solid. ¹ H NMR (400 MHz, CDCl ₃ ): δ _H 7.91 (s, 1H), 7.38-7.30 (m, 2H), 7.28-7.23 (m, 1H), 7.17-7.15 (d, 1H), 5.10-5.02 (br. s, 2H), 2.57-2.49 (br. q, 2H), 1.14-1.10 (t, 3H).

No. Ib: 6-Bromo-5-(2-ethylphenyl)[1,3]thiazolo[4,5-b]pyridine-2-thiol To a stirred solution of compound XXIb (8.89 g, 22.35 mmol, 1.0 equiv) in DMF (90 mL) was added O-ethyldithiocarbonate potassium salt (22.16 g, 134.08 mmol, 6.0 equivalent). The resulting mixture was heated at reflux for 10 days. The reaction mixture was cooled to room temperature, poured onto ice water and acidified using 2 N HCl. The resulting precipitate was filtered, washed with water and then dried under reduced pressure to provide compound Ib (6.34 g, 81% yield). ¹ H NMR (400 MHz, CDCl ₃ ): δ _H 9.67 (br. s, 1H), 8.01 (s, 1H), 7.44-7.40 (m, 1H), 7.37-7.35 (d, 1H), 7.32-7.27 (m, 1H), 7.19-7.17 (m, 1H), 2.53-2.42 (br. m, 2H), 1.12-1.08 (t, 3H).

I-015: 6-Bromo-5-(2-ethylphenyl)[1,3]thiazolo[4,5-b]pyridine To a stirred solution of compound Ib (6.34 g, 15.88 mmol, 1.0 equiv) in acetic acid (35 mL) was added iron powder (11.09 g, 198.53 mmol, 12.5 equiv) carefully in portions at room temperature. The resulting mixture was stirred at 100 °C for 8 h. The reaction mixture was cooled to 60 °C and iron powder was removed by filtration. The filtrate was diluted with water and the resulting precipitate was isolated by filtration, washed with water. _The filter cake was dissolved in _CH2Cl2 and then washed with water. The organic layer was dried over anhydrous MgSO ₄ , filtered and dried under reduced pressure. The resulting residue was purified via flash column chromatography on silica gel eluting with hexane/EtOAc (gradient) to provide compound 1-015 (4.83 g, 95% yield).

I-014: 5-(2-Ethylphenyl)-6-methyl-[1,3]thiazolo[4,5-b]pyridine At room temperature and under an argon atmosphere, to compound I-015 (2.00 g, 6.27 mmol, 1.0 equivalents), methyl To a stirred mixture of acid (705 mg, 12.53 mmol, 2.0 equiv) and potassium phosphate (5.32 g, 25.06 mmol, 4.0 equiv) in anhydrous PhMe (10 mL) was added palladium(II) acetate (141 mg, 0.63 mmol, 0.1 equiv) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (514 mg, 1.25 mmol, 0.2 equiv). The resulting mixture was stirred at reflux for 8 h. The reaction mixture was cooled to room temperature, diluted with water and PhMe, followed by the addition of ammonium pyrrolidine dithiocarbamate (451 mg, 2.75 mmol, 0.44 equiv). The resulting mixture was stirred at room temperature for 1 h, the organic layer was washed with saturated aqueous NaHCO ₃ , dried over anhydrous MgSO ₄ , filtered and concentrated under reduced pressure. The resulting residue was purified via flash column chromatography on silica gel eluting with hexane/EtOAc (gradient) to provide compound 1-014 (1.5 g, 89% yield).

No. XXIIIa: 2-fluoro-1-phenyl-3-(dimethylamino)prop-2-en-1-one A mixture of 2-fluoro-1-phenylethanone (280 mg, 2.00 mmol) in DMF.DMA (2 mL) was stirred at 120 °C for 1.5 h at room temperature. The resulting mixture was cooled to room temperature and concentrated under reduced pressure to provide compound XXIIIa which was used directly in the next step without further purification.

No. I-011: 6-fluoro-5-phenyl-thiazolo[4,5-b]pyridine and No. I-012: 6-chloro-5-phenyl-thiazolo[4,5-b] pyridine To a stirred mixture of tert-butyl 1,3-thiazol-4-ylcarbamate (400 mg, 2.00 mmol) in 4 M HCl/dioxane (4 mL) was added compound at room temperature XXIIIa. The resulting mixture was stirred at reflux for 5 h. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was diluted with EtOAc, washed with saturated aqueous NaHCO ₃ and brine. The organic layer was dried over anhydrous _Na2SO4 , _filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with petroleum ether/EtOAc to provide compound 1-011 (39 mg, 8% yield) and compound 1-012 (14 mg, 3% yield ).

No. XXIIIb: 2-ethoxy-1-(2-fluorophenyl)-3-(dimethylamino)prop-2-en-1-one A mixture of 2-ethoxy-1-(2-fluorophenyl)ethanone (273 mg, 1.50 mmol) in DMF.DMA (2.4 ml) was stirred at 120°C for 4 h. The resulting mixture was cooled to room temperature and concentrated under reduced pressure to provide compound XXIIIb which was used directly in the next step without further purification.

No. I-033: 6-ethoxy-5-(2-fluorophenyl)-thiazolo[4,5-b]pyridine To a stirred mixture of tert-butyl 1,3-thiazol-4-ylcarbamate (300 mg, 1.50 mmol) in 4 M HCl/dioxane (3 mL) was added compound at room temperature XXIIIb. The resulting mixture was stirred at reflux for 5 h. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was diluted with EtOAc, washed with saturated aqueous NaHCO ₃ and brine. The organic layer was dried over anhydrous _Na2SO4 , _filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with petroleum ether/EtOAc to provide compound 1-033 (50 mg, 12% yield).

No. XXIIIc: 1-(3-fluoro-2-thienyl)-3-(dimethylamino)-2-methyl-prop-2-en-1-one A mixture of 1-(3-fluoro-2-thienyl)propan-1-one (474 mg, 3.00 mmol) in DMF.DMA (2 mL) was stirred at 100 °C for 3 h. The resulting mixture was cooled to room temperature and concentrated under reduced pressure to provide compound XXIIIc which was used directly in the next step without further purification.

No. I-034: 5-(3-Fluoro2-thienyl)-6-methyl-thiazolo[4,5-b]pyridine To a stirred mixture of tert-butyl 1,3-thiazol-4-ylcarbamate (600 mg, 3.00 mmol) in 4 M HCl/dioxane (10 mL) was added compound at room temperature XXIIIc. The resulting mixture was stirred at reflux for 4 h. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was diluted with EtOAc, washed with saturated aqueous NaHCO ₃ and brine. The organic layer was dried over anhydrous _Na2SO4 , _filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with petroleum ether/EtOAc to provide compound 1-034 (410 mg, 55% yield).

The compounds cited below were obtained analogously to the examples of preparation cited above and at the appropriate points, taking into account the general details relating to the preparation of thiazolopyridines. . Table 1: Examples of preferred compounds of general formula (I) (I) instance number R ¹ R ² R ³ R ⁴ I-001 2,4-Difluorophenyl Br h h I-002 2-Chlorophenyl Br h SH I-003 4-fluoro-3-thienyl Me h h I-004 3,5-Dimethyl-1,2-oxazol-4-yl h h h I-005 4-methyl-2-thienyl Et h h I-006 3-methyl-2-thienyl Et h h I-007 4-Methylthiadiazol-5-yl h h h I-008 Ph Br h h I-009 2-fluorophenyl Allyl h h I-010 2-fluorophenyl Methoxymethyl h h I-011 Ph f h h I-012 Ph Cl h h I-013 Ph OMe h h I-014 2-Ethylphenyl Me h h I-015 2-Ethylphenyl Br h h I-016 2-methoxyphenyl Br h h I-017 2,3-Dimethylphenyl Br h h I-018 3-fluorophenyl Br h h I-019 2-thienyl Et h h I-020 2-thienyl Me h h I-021 3-thienyl Me h h I-022 3-thienyl Et h h I-023 2-fluorophenyl OMe h h I-024 2-Bromophenyl h h h I-025 2-Bromophenyl Me h h I-026 2-fluorophenyl Cyclopropylmethyl h h I-027 2-fluorophenyl f h h I-028 2,3-Dimethylphenyl Me h h I-029 3-Chloro-2-fluorophenyl Br h h I-030 2-fluoro-3-methylphenyl Me h h I-031 3-Chloro-2-fluorophenyl Me h h I-032 2,4-Dimethyl-3-thienyl Me h h I-033 2-fluorophenyl OEt h h I-034 3-fluoro-2-thienyl Me h h I-035 2-Bromo-6-fluorophenyl h h h I-036 3-Bromo-2-thienyl Me h h I-037 2-Bromo-3-thienyl h h h I-038 2,5-Difluorophenyl Br h h I-039 2,4,5-Trifluorophenyl Br h h I-040 2,5-Difluorophenyl Me h h I-041 2,4,5-Trifluorophenyl Me h h

Spectral data for selected table examples: The spectral data presented below for selected table examples were either interpreted by ^{conventional1H} -NMR or evaluated by the NMR peak list method.

a) Conventional ¹ H-NMR interpretation I-001: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.33 (s, 1H), 8.64 (s, 1H), 7.54-7.48 (m, 1H), 7.05- 7.00 (m, 1H), 6.97-6.92 (m, 1H). I-002: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.68 (s, 1H), 8.02 (s, 1H), 7.52-7.49 (m, 1H), 7.44-7.38 (m, 2H), 7.34 -7.31 (m, 1H). I-003: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.29 (s, 1H), 8.24 (s, 1H), 7.48 (t, 1H), 6.86 (dd, 1H), 2.48 (d, 3H ). I-004: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.35 (s, 1H), 8.40 (d, 1H), 7.46 (d, 1H), 6.86 (dd, 1H), 2.68 (s, 3H ), 2.54 (s, 3H). I-005: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.22 (s, 1H), 8.19 (s, 1H), 7.38 (d, 1H), 7.05 (t, 1H), 3.08 (q, 2H ), 2.33 (d, 3H), 1.38 (t, 3H). I-006: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.26 (s, 1H), 8.26 (s, 1H), 7.32 (d, 1H), 6.94 (d, 1H), 2.78 (q, 2H ), 2.14 (s, 3H), 1.20 (t, 3H). I-007: ¹ H-NMR (600 MHz, CDCl ₃ ) δ _H 9.41 (s, 1H), 8.49 (d, 1H), 7.75 (d, 1H), 3.07 (s, 3H). I-009: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.36 (s, 1H), 8.34 (s, 1H), 7.51-7.44 (m, 2H), 7.28 (m, 1H), 7.19 (t , 1H), 5.85 (m, 1H), 5.13 (m, 1H), 5.03 (m, 1H), 3.47 (m, 2H). I-010: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.32 (s, 1H), 8.58 (s, 1H), 7.55 (m, 1H), 7.46 (m, 1H), 7.30 (m, 1H ), 7.17 (m, 1H), 4.51 (s, 2H), 3.38 (s, 3H). I-011: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.28 (s, 1H), 8.13-8.09 (m, 3H), 7.55-7.46 (m, 3H). I-012: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.32 (s, 1H), 8.44 (s, 1H), 7.83 (m, 2H), 7.53-7.46 (m, 3H). I-013: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.12 (s, 1H), 8.03 (m, 2H), 7.83 (s, 1H), 7.50-7.43 (m, 3H), 3.96 (s , 3H). I-014: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.24 (s, 1H), 8.21 (s, 1H), 7.38-7.34 (m, 2H), 7.29-7.25 (m, 1H), 7.20 -7.18 (d, 1H), 2.51-2.42 (br m, 2H), 2.25 (s, 3H), 1.08-1.05 (t, 3H). I-016: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.28 (s, 1H), 8.58 (s, 1H), 7.47-7.43 (m, 1H), 7.38-7.36 (m, 1H), 7.11 -7.17 (m, 1H), 7.02-7.00 (d, 1H), 3.80 (s, 3H). I-019: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.24 (s, 1H), 8.22 (s, 1H), 7.55 (dd, 1H), 7.48 (dd, 1H), 7.15 (dd, 1H ), 3.10 (q, 2H), 1.39 (t, 3H). I-020: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.23 (s, 1H), 8.17 (d, 1H), 7.64 (dd, 1H), 7.48 (dd, 1H), 7.16 (dd, 1H ), 2.75 (d, 3H). I-021: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.23 (s, 1H), 8.19 (d, 1H), 7.73 (dd, 1H), 7.63 (dd, 1H), 7.42 (dd, 1H ), 2.64 (d, 3H). I-022: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.25 (s, 1H), 8.24 (s, 1H), 7.65 (dd, 1H), 7.50 (dd, 1H), 7.41 (dd, 1H ), 2.95 (q, 2H), 1.29 (t, 3H). I-023: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.13 (s, 1H), 7.83 (s, 1H), 7.63 (m, 1H), 7.43 (m, 1H), 7.27 (m, 1H ), 7.15 (m, 1H), 3.94 (s, 3H). I-024: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.36 (s, 1H), 8.40 (d, 1H), 7.77 (d, 1H), 7.72-7.70 (m, 2H), 7.45 (m , 1H), 7.30 (m, 1H), 7.15 (m, 1H). I-025: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.26 (s, 1H), 8.23 (d, 1H), 7.68 (m, 1H), 7.44 (m, 1H), 7.37 (m, 1H ), 7.30 (m, 1H), 2.32 (d, 3H). I-026: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.27 (s, 1H), 8.52 (s, 1H), 7.51-7.40 (m, 2H), 7.27 (m, 1H), 7.15 (m , 1H), 2.62 (d, 2H), 0.92 (m, 1H), 0.55 (m, 2H), 0.14 (m, 2H). I-027: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.30 (s, 1H), 8.13 (d, 1H), 7.76 (m, 1H), 7.49 (m, 1H), 7.32 (m, 1H ), 7.21 (m, 1H). I-029: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.34 (s, 1H), 8.65 (s, 1H), 7.55-7.51 (m, 1H), 7.43-7.39 (m, 1H), 7.25 -7.21 (m, 1H). I-030: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.25 (s, 1H), 8.22 (s, 1H), 7.32-7.28 (m, 1H), 7.27-7.22 (m, 1H), 7.18 -7.14 (m, 1H), 2.35 (s, 3H). I-031: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.27 (s, 1H), 8.25 (s, 1H), 7.53-7.48 (m, 1H), 7.44-7.40 (m, 1H), 7.25 -7.21 (m, 1H), 2.40 (s, 3H). I-032: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.30 (s, 1H), 8.30 (s, 1H), 6.81 (dd, 1H), 2.28 (s, 3H), 2.22 (s, 3H ), 1.96 (d, 3H). I-033: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.18 (s, 1H), 7.83 (d, 1H), 7.63 (m, 1H), 7.44 (m, 1H), 7.27 (m, 1H ), 7.15 (m, 1H), 4.17 (q, 2H), 1.41 (t, 3H). I-034: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.25 (s, 1H), 8.22 (d, 1H), 7.36 (dd, 1H), 6.89 (d, 1H), 2.57 (d, 3H ). I-035: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.39 (s, 1H), 8.45 (d, 1H), 7.53-7.50 (m, 2H), 7.29 (m, 1H), 7.18 (m , 1H). I-040: ¹ H-NMR (400 MHz, CDCl ₃ ) δ _H 9.27 (s, 1H), 8.24 (s, 1H), 7.28-7.23 (m, 1H), 7.15-7.11 (m, 1H), 2.42 (s, 3H).

b) NMR peak list method The ¹ H-NMR data of the selected examples are written in the form of a ¹ H-NMR peak list. For each signal peak, the delta value (in ppm) and signal intensity (in parentheses) are listed. A semicolon delimiter is used between the delta value-signal strength pairs.

An example peak list thus has the _following form: δ ₁ (intensity ₁ ); δ ₂ (intensity ₂ ); . . . ; _{δ i} (intensity _i ); . . . The iso-signals are related to the height (in cm) in printed examples of NMR spectra and show the true relationship of signal intensities. A self-broadening signal may exhibit several peaks or middle portions of the signal and their relative intensities compared to the strongest signal in the spectrum. To calibrate the chemical shifts of the ¹ H spectra, tetramethylsilane and/or solvent chemical shifts were used, especially in the case of spectra measured in DMSO. Therefore, in the NMR peak list, the tetramethylsilane peak may appear, but does not necessarily appear. The ¹ H-NMR peak list is similar to a classical ¹ H-NMR spectrum and therefore generally contains all peaks, which are listed in the classical NMR interpretation. In addition, it may exhibit classical ¹ H-NMR-like signals of the solvent, stereoisomers of the target compound (which are also the target of the present invention) and/or peaks of impurities. To show compound signals in the δ range of solvent and/or water, common peaks for solvents (eg DMSO peak and water peak in DMSO-D ₆ ) are shown in these ¹ H-NMR peak lists and usually have an average of high strength. Peaks for stereoisomers of the target compound and/or peaks for impurities typically have, on average, a lower intensity than peaks for the target compound (eg, >90% purity). Such stereoisomers and/or impurities may be typical for a particular preparation. Therefore, its peaks can help to identify the reproducibility of its preparation method through "by-product fingerprints". An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD-simulation, and using empirically estimated expected values) can isolate the peaks of the target compounds, using additional intensity filters if necessary. This separation will be similar to picking the relevant peaks in ^classical1H -NMR interpretation. Additional details of NMR data elucidation and peak listings can be found in publication Research Disclosure Database No. 564025, "Citation of NMR Peaklist Data within Patent Applications". I-008: ¹ H-NMR (400.6 MHz, CDCl ₃ ): δ= 9.3197 (3.8); 8.6434 (13.7); 8.0097 (1.5); 7.7813 (7.2); 7.7633 (8.4); 7.6377 (1.4); 7.6284 ( 1.2); 7.6228 (1.2); 7.4942 (9.2); 7.4780 (16.0); 7.4479 (1.3); 7.4267 (1.0); 7.4098 (1.0); 7.3814 (1.6); 7.2604 (30.3); 8); 5.0270 ( 2.0); 1.6013 (1.0); -0.0002 (44.8); -0.0084 (1.9) I-015: ¹ H-NMR (400.6 MHz, CDCl ₃ ): δ= 7.3518 (0.7); 7.3482 (0.9); 7.3322 (2.0); 7.3291 (1.9); 7.3133 (9.4); 7.3055 (2.6); 7.3012 ( 7.2864 (1.2); 7.2598 (41.3); 7.2505 (1.3); 7.2368 (2.1); 7.2322 (1.8); 7.2192 (1.2); 7.2148 (1.2); ); 7.1384 ( 1.7); 5.2994 (3.2); 4.5593 (3.0); 2.5119 (1.0); 1.6515 (0.7); 1.5699 (2.0); 1.2989 (0.9); 1.2816 (1.0); ; 1.1980 ( 1.0); 1.1908 (0.8); 1.1777 (0.7); 1.1700 (0.7); 1.1524 (0.6); 1.1455 (1.4); 1.1372 (7.5); 1.1281 (1.8); ); 1.0854 ( 0.7); 0.0082 (1.6); -0.0002 (60.1); -0.0081 (2.1) I-017: ¹ H-NMR (400.6 MHz, CDCl ₃ ): δ= 10.3995 (0.6); 9.3281 (5.0); 8.6233 (5.4); 7.3467 (0.7); 7.2623 (6.1); 7.2472 (2.3); 7.2214 ( 1.4); 7.2028 (2.4); 7.1839 (1.3); 7.1335 (2.3); 7.1147 (1.5); 4.9886 (1.3); 2.9693 (1.2); 2.8952 (1.2); ); 2.2006 ( 0.5); 2.0975 (9.5); 2.0471 (16.0); -0.0002 (7.8) I-018: ¹ H-NMR (400.6 MHz, CDCl ₃ ): δ= 9.3382 (3.2); 8.6565 (16.0); 8.0177 (13.5); 7.5730 (3.6); 7.5538 (5.0); 7.5059 (3.3); 7.4838 ( 6.0); 7.4698 (3.2); 7.4642 (5.8); 7.4503 (5.7); 7.4446 (5.8); 7.4397 (4.3); 7.4356 (5.4); 7.3700 (2.0); 7.3449 (1.9); 0); 7.2528 ( 1.6); 7.2469 (1.1); 7.2285 (0.7); 7.1929 (3.0); 7.1711 (5.2); 7.1655 (4.4); 7.1517 (2.4); ; 1.5607 ( 1.0); 1.2553 (7.5); 0.8797 (1.3); 0.1454 (1.1); 0.0146 (0.8); 0.0080 (8.6); -0.0002 (251.2); -0.0084 (6.8); -0.0136 (1.1); 0 ); -0.1496 (1.0) I-028: ¹ H-NMR (400.6 MHz, CDCl ₃ ): δ= 9.3289 (0.8); 9.3112 (6.5); 9.3015 (1.1); 8.6204 (7.6); 8.0239 (4.4); 7.4535 (0.5); 7.4364 ( 0.9); 7.3777 (0.7); 7.3569 (1.3); 7.3361 (0.7); 7.2695 (0.6); 7.2648 (1.6); 7.2639 (1.5); 7.2597 (81.7); ); 7.2446 ( 1.4); 7.2334 (0.5); 7.2213 (1.2); 7.2023 (2.0); 7.1828 (1.3); 7.1688 (0.8); 7.1507 (1.1); ; 7.0325 ( 0.5); 6.9962 (0.5); 6.6333 (2.8); 6.6123 (2.7); 5.2992 (7.4); 4.1487 (0.7); 4.1308 (2.1); 4.1130 (2.2); ); 3.6542 ( 1.1); 3.5866 (1.8); 3.5693 (0.8); 2.9229 (1.2); 2.3519 (9.7); 2.3183 (4.7); 2.2933 (0.7); ); 2.0450 ( 13.2); 2.0259 (5.6); 1.9733 (1.6); 1.9663 (2.3); 1.9579 (1.6); 1.8002 (0.7); 1.6519 (0.7); 1.6092 (0.7); 1.5793 (0.7); 5); 1.3044 ( 1.6); 1.2771 (5.3); 1.2644 (7.8); 1.2594 (10.8); 1.2415 (3.8); 1.1488 (0.6); 0.8989 (4.4); 0.8820 (16.0); 0.8643 (5.9); 0); 0.0062 ( 1.3); 0.0047 (1.6); -0.0002 (119.6); -0.0061 (0.9); -0.0085 (3.8) I-036: ¹ H-NMR (400.6 MHz, CDCl ₃ ): δ= 8.5698 (0.8); 8.5640 (0.8); 8.1830 (1.9); 8.1811 (1.9); 7.5374 (0.6); 7.5328 (0.8); 7.5231 ( 2.0); 7.5198 (1.2); 7.5097 (2.0); 7.4734 (2.5); 7.4604 (2.7); 7.4197 (2.3); 7.4065 (2.5); 7.2608 (47.6); ); 7.1278 ( 0.9); 7.1149 (0.9); 7.1074 (2.6); 7.0944 (2.5); 7.0906 (0.8); 7.0799 (2.6); 7.0772 (0.8); 7.0667 (2.3); ; 5.1936 ( 0.5); 5.1780 (0.6); 3.9826 (0.6); 3.9032 (16.0); 3.8944 (0.7); 3.8811 (0.6); 3.6658 (0.5); 2.4674 (6.5); ); 1.5459 ( 12.5); 1.5329 (2.0); 1.4311 (0.5); 1.3616 (0.6); 1.3364 (2.5); 1.3332 (1.6); 1.3191 (2.6); 1.2991 (2.8); ); 1.2303 ( 1.6); 1.2122 (1.1); 1.1767 (0.5); 0.9686 (1.4); 0.9500 (2.6); 0.9314 (1.3); 0.8965 (0.9); ; 0.0080 ( 2.1); -0.0002 (71.4); -0.0085 (3.0) I-037: ¹ H-NMR (400.6 MHz, CDCL ₃ ): Δ = 9.3400 (16.0); 8.4210 (9.2); 8.4158 (10.6); 8.3949 (11.6); 8.0732 (0.7); 8.0672 (10.2); 8.0521 ( 0.8); 8.0463 (9.3); 8.0175 (1.2); 8.0126 (1.0); 7.6267 (11.6); 7.6124 (13.0); 7.4058 (1.2); 7.3848 (1.1); 0.8); 7.2617 ( 29.4); 3.9294 (7.0); 2.0454 (1.9); 1.6145 (1.5); 1.2771 (0.7); 1.2593 (1.6); 1.2415 (0.6); 0.0699 (0.6); 0.0079 (1.3); 2);- 0.0085 (1.5) I-038: ¹ H-NMR (400.6 MHz, CDCl ₃ ): δ= 9.3387 (13.5); 8.6497 (16.0); 7.2614 (22.3); 7.2552 (1.1); 7.2530 (1.2); 7.2497 (1.1); 7.2448 ( 1.0); 7.2429 (1.0); 7.2381 (2.0); 7.2360 (1.3); 7.2337 (1.9); 7.2292 (1.1); 7.2244 (1.0); ; 7.1740 ( 1.9); 7.1714 (2.1); 7.1682 (3.5); 7.1619 (1.8); 7.1577 (4.2); 7.1532 (4.0); 7.1499 (2.0); 7.1443 (2.0); ; 5.0318 ( 0.5); 4.1309 (1.0); 4.1131 (1.0); 2.0455 (4.9); 1.3335 (1.1); 1.2842 (1.6); 1.2773 (1.5); 1.2594 (3.5); ; 0.0080 ( 0.8); -0.0002 (30.4); -0.0085 (0.9) I-039: ¹ H-NMR (400.6 MHz, CDCl ₃ ): δ= 9.3529 (3.1); 8.6541 (3.1); 7.3853 (0.7); 7.3678 (0.7); 7.2637 (6.3); 7.0720 (0.8); 7.0558 ( 0.8); 2.0996 (16.0); -0.0002 (8.6) I-041: ¹ H-NMR (400.6 MHz, CDCl ₃ ): δ= 9.2781 (10.7); 9.2721 (0.7); 9.2579 (4.4); 8.2476 (6.0); 8.2457 (6.3); 8.2239 (2.4); 8.2220 ( 2.5); 7.4317 (1.1); 7.4153 (1.2); 7.4098 (1.2); 7.4064 (1.3); 7.3934 (1.2); 7.3900 (1.3); 7.3845 (1.2); ); 7.2105 ( 0.8); 7.1956 (0.8); 7.1874 (0.8); 7.1724 (0.8); 7.0794 (1.1); 7.0634 (1.2); 7.0565 (1.4); 7.0546 (1.4); ; 7.0318 ( 1.2); 7.0157 (1.2); 7.0101 (0.6); 6.9946 (0.6); 6.9858 (0.6); 6.9706 (0.5); 2.8954 (0.9); 2.8873 (0.6); 2.4165 (12.6); 0); 2.4116 ( 14.5); 2.4101 (15.5); 2.3466 (4.2); 2.3418 (4.3); 2.0454 (0.8); 1.5871 (4.8); 1.2594 (0.6); .0)

The present invention additionally provides one or more compounds of general formula (I) and/or salts thereof (as defined above, preferably in one of the embodiments identified as preferred or particularly preferred), especially one or more compounds of formula Compounds of (I-001) to (I-041) and/or salts thereof (in each case as defined above) as herbicides and/or plant growth regulators preferably in useful plants and/or ornamental plants use in crops.

The present invention additionally provides a method for controlling harmful plants and/or regulating plant growth, characterized in that an effective amount of - one or more compounds of general formula (I) and/or salts thereof (as defined above, preferably in one of the preferred or particularly preferred embodiments identified), especially one or more compounds of formula (I- 001) to (I-041) compounds and/or salts thereof (in each case as defined above), or - the composition of the invention as defined below, Application to (harmful) plants, (harmful) plant seeds, soil or cultivated areas in or on which (harmful) plants grow.

The present invention also provides a method for controlling undesired plants, preferably in a crop of useful plants, characterized in that an effective amount of - one or more compounds of general formula (I) and/or salts thereof (as defined above, preferably in one of the preferred or particularly preferred embodiments identified), especially one or more compounds of formula (I- 001) to (I-041) compounds and/or salts thereof (in each case as defined above), or - the composition of the invention as defined below, Application to undesired vegetation (e.g. harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), seeds of undesired plants (i.e. plant seeds such as grains, seeds or vegetative reproductive organs such as tubers or The young part of the shoot with the bud), the soil in or on which undesired vegetation grows (such as the soil of arable or non-cultivated land) or the cultivated area (ie the area where the growth of undesired vegetation).

The present invention additionally also provides a method for regulating the growth of plants, preferably useful plants, characterized in that an effective amount of - one or more compounds of general formula (I) and/or salts thereof (as defined above, preferably in one of the preferred or particularly preferred embodiments identified), especially one or more compounds of formula (I- 001) to (I-041) compounds and/or salts thereof (in each case as defined above), or - the composition of the invention as defined below, Application to plants, plant seeds (that is to say plant seeds, such as grains, seeds or vegetative reproductive organs, such as tubers or shoot parts with buds), soil in or on which plants grow (for example, soil on arable or non-arable land ) or cultivated area (that is, the area where plants grow).

In this context, the compounds according to the invention or the compositions according to the invention can be applied, for example, by pre-sowing (if appropriate also by incorporation into the soil), pre-emergence or post-emergence processes. Specific examples of some representative monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds of the present invention are set forth below, without intending to limit the particular species listed.

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

The general formula (I) compound of the present invention and/or its salt are suitable for controlling the monocotyledonous and dicotyledonous harmful plants of following genus: monocotyledonous harmful plant belongs to : goat grass (Aegilops), ice grass (Agropyron), clip grass ( Agrostis), Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Dog Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa , Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Millet (Panicum), Paspalum (Paspalum), Phalaris (Phalaris), Timothy (Phleum), Xiahe (Poa), Rottboellia (Rottboellia), Sagittaria (Sagittaria), Scirpus (Scirpus), Setaria (Setaria) , Sorghum (Sorghum). Dicotyledonous harmful plant genera : Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia ), Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium , Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha ), Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus ( Ranunculus), Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Golden noon flower ( Sida), mustard seed (Sinapis), nightshade (Solanum), chicory (Sonchus), pointed flower (Sphenoclea), chickweed (Stellaria), dandelion (Taraxacum), scorpion (Thlaspi), clover (Trifolium), castor (Urtica), Veronica, Viola, Xanthium.

When the compound of the present invention is applied to the soil surface (pre-emergence method) before harmful plants (grass weeds and/or broad-leaved weeds) germinate, the emergence of seedlings of grass weeds or broad-leaved weeds can be completely prevented Or the weed grows until it reaches the cotyledon stage, but then stops growing and eventually dies completely after three to four weeks have passed.

If the active compound is applied to the green parts of the plants after emergence, growth ceases after the treatment and the harmful plants remain in the growth stage at the time of application, or they die completely after a certain time, thus harmful to weeds of crop plants In this way the competition is eliminated very early and in a sustained manner.

Although the compounds of the present invention show outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, depending on the structure of the respective compounds of the present invention and their application rates, crop plants of economically important crops (such as dicotyledonous crops of the genus Arachis) , Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Sweet Potato, Lactuca, Flax (Linum), tomato (Lycopersicon), Miscanthus (Miscanthus), tobacco (Nicotiana), bean (Phaseolus), pea (Pisum), nightshade, broad bean (Vicia) or monocotyledonous plants of the genus Allium (Allium), pineapple (Ananas), Asparagus, Oats (Avena), Barley (Hordeum), Rice (Oryza), Millet (Panicum), Sugarcane (Saccharum), Rye (Secale), Sorghum, Triticale (triticale), Wheat (triticum), Maize (Zea)) is only slightly damaged or not damaged at all. For these reasons, the compounds according to the invention are very suitable for the selective control of undesired vegetative growth in plant crops such as agriculturally useful plants or ornamental plants.

In addition, the compounds according to the invention (depending on their specific structure and the applied rate at which they are deployed) have outstanding growth-regulating properties in crop plants. They intervene with a regulatory effect in the plant's own metabolism and can thus be used to control plant components and facilitate harvesting (for example by triggering dehydration and growth retardation). In addition, they are also suitable for the general control and inhibition of undesired vegetative growth without killing the plants in the process. Inhibition of vegetative growth plays an important role in many monocot and dicot crops because, for example, it can reduce or completely prevent lodging.

By virtue of their herbicidal and plant growth-regulating properties, the active compounds can also be used for controlling harmful plants in crops of genetically modified plants or plants modified by customary mutagenesis. In general, transgenic plants are characterized by certain advantageous properties, such as resistance to certain insecticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases (such as certain insects or microorganisms, such as fungi, bacteria or virus) resistance. Other specific characteristics relate to, for example, the quantity, quality, storability, composition and specific components of the harvested material. For example, there are known transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition in the harvested material.

Preferably for transgenic crops, economically important transgenic crops of useful plants and ornamental plants (for example crops of cereals such as wheat, barley, rye, oats, millet, japonica rice and maize or other sugar beet, cotton, soybean , rape, potato, tomato, pea and other plant crops) using the compound of the present invention and/or its salt.

Preferably, the compounds according to the invention are employed as herbicides in crops of useful plants which are resistant or have been rendered recombinantly resistant to the phytotoxic effects of herbicides. the

By virtue of their herbicidal and plant growth-regulating properties, the active compounds can also be used for controlling harmful plants in crops of genetically modified plants which are known or are yet to be developed. In general, transgenic plants are characterized by certain advantageous properties, such as resistance to certain insecticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases (such as certain insects or microorganisms, such as fungi, bacteria or virus) resistance. Other specific characteristics relate to, for example, the quantity, quality, storability, composition and specific components of the harvested material. For example, there are known transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition in the harvested material. Other specific properties may be tolerance or resistance to abiotic stress factors such as heat, cold, drought, salinity and ultraviolet radiation.

Preferably, economically important transgenic crops of useful plants and ornamental plants (such as crops of cereals such as wheat, barley, rye, oats, triticale, millet, japonica rice, cassava and corn or other sugar beet, cotton, soybean , rape, potato, tomato, pea and other plant crops) the compound of general formula (I) or its salt of the present invention is used.

Preferably, the compounds of the general formula (I) can be used as herbicides in crops of useful plants which are resistant or have been rendered resistant by recombinant means to the phytotoxic effects of herbicides. the

Conventional means of producing novel plants having improved properties compared to existing plants include, for example, traditional farming methods and the generation of mutants. Alternatively, novel plants with altered properties can be produced by means of recombinant methods.

A large number of biological techniques by which novel transgenic plant molecules with improved properties can be generated are known to those skilled in the art. For such recombinant manipulations, nucleic acid molecules allowing mutagenesis or sequence changes by recombinant DNA sequences can be introduced into plastids. By means of standard methods, it is possible, for example, to perform base exchanges, to remove partial sequences or to add natural or synthetic sequences. To join DNA fragments to each other, adapters or adapters can be added to the fragments.

For example, plant cells with reduced gene product activity can be generated by expressing at least one corresponding antisense RNA, sense RNA for co-suppression, or by expressing at least one specific cleavage as mentioned above Suitably constructed ribozymes for transcripts of gene products.

For this purpose, firstly DNA molecules can be used which cover the entire coding sequence of the gene product (including any flanking sequences which may be present) as well as only parts of the coding sequence which in this case need to be long enough to be present in the cell. antisense effect) DNA molecules. DNA sequences that have a high degree of homology to the coding sequence of the gene product but do not lead to complete identity can also be used.

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

Transgenic plant cells can be regenerated by known techniques to produce whole plants. In principle, the transgenic plants can be plants of any desired plant species, ie not only monocots but also dicots.

Thus, it is possible to obtain transgenic plants whose properties have been altered by overexpressing, suppressing or suppressing homologous (=natural) genes or gene sequences or expressing heterologous (=foreign) genes or gene sequences.

Preferably, the compounds (I) of the present invention are used in transgenic crops resistant to: growth regulators such as dicamba; or inhibition of essential plant enzymes such as acetyl lactate synthase (ALS), EPSP synthesis enzymes, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD)); or from sulfonylureas, glyphosate (glyphosate), glufosinate (glufosinate) or benzene Formylisoxazoles and herbicides of the group of similar active compounds.

When the active compounds according to the invention are used in transgenic crops, not only the effects on harmful plants observed in other crops occur, but also generally in specific transgenic crops have specific applied effects, such as a change or in particular a broadening of the range Controllable weeds, changing the application rate available for application, preferably good combination with herbicides resistant to transgenic crops and affecting the growth and yield of transgenic crop plants.

The present invention thus 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 plants or ornamental plants, optionally transgenic crop plants.

Preferably, it is used in cereals, preferably corn, wheat, barley, rye, oats, millet or japonica rice etc. by pre-emergence or post-emergence methods.

Preferably, it is also used in soybean by pre-emergence or post-emergence methods.

The use according to the invention for controlling harmful plants or regulating plant growth also includes the case in which the active compound of general formula (I) or a salt thereof is not formed from a precursor substance ("prodrug") until after application to the plant, in plants or in soil.

The present invention also provides the use (in a method) of one or more compounds of general formula (I) or salts thereof or compositions of the invention (as defined below) for controlling harmful plants or for regulating plant growth, which use comprises An effective amount of one or more compounds of the general formula (I) or salts thereof is applied to plants (harmful plants (if appropriate) and useful plants), plant seeds, the soil in or on which the plants grow or the cultivated area.

The present invention also provides a herbicidal and/or plant growth regulating composition, characterized in that the composition comprises (a) one or more compounds of general formula (I) and/or salts thereof (as defined above, preferably in one of the embodiments identified as preferred or preferred), especially one or more compounds of formula ( Compounds of I-001) to (I-041) and/or salts thereof (in each case as defined above), and (b) one or more other substances selected from groups (i) and/or (ii): (i) One or more other agrochemical active substances preferably selected from the group consisting of: insecticides, acaricides, nematicides, other herbicides (i.e. not corresponding to the general formula defined above (I)), fungicides, safeners, fertilizers and/or other growth regulators, (ii) One or more formulation adjuvants commonly used in crop protection. the Herein, the other agrochemical active substances of component (i) of the composition of the present invention are preferably selected from "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 The group of substances mentioned.

The herbicidal or plant growth regulating composition of the present invention preferably comprises one, two, three or more formulation adjuvants (ii) commonly used in crop protection selected from the group consisting of: surfactants, emulsifiers , dispersants, film formers, thickeners, inorganic salts, dedusting agents, solid carriers at 25°C and 1013 mbar (preferably adsorptive granular inert materials), wetting agents, antioxidants, Stabilizers, buffer substances, antifoaming agents, water, organic solvents (preferably organic solvents miscible with water in any ratio at 25° C. and 1013 mbar).

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

Compounds of general formula (I) and/or salts thereof can be formulated in various ways requiring 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, for spreading and Soil-applied granules, granules in particulate form (GR), spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and wax.

Such individual formulation types and formulation auxiliaries (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 ed., Darland Books, Caldwell N.J.; H.v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd ed. ed., Interscience, N.Y. 1963; McCutcheon, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt , "Grenzflächenaktive Äthylenoxidaddukte" [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie" [Chemical Technology], Vol. 7, C. Hanser Verlag Munich, 4th edition , 1986.

Wettable powders are preparations which can be dispersed uniformly in water and which, in addition to diluents or inert substances and active compounds, also include ionic and/or nonionic surfactants (wetting agents, dispersing agents), such as polyoxy Ethylated Alkylphenols, Polyoxyethylated Fatty Alcohols, Polyoxyethylated Fatty Amines, Fatty Alcohol Polyglycol Ether Sulfates, Alkane Sulfonates, Alkylbenzene Sulfonates, Lignosulfonic Acid Sodium, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or alternatively sodium oleylmethyl taurate. To produce wettable powders, the herbicidally active compounds are, for example, finely ground in customary apparatus (eg hammer mills, blower mills and air-jet mills) and mixed simultaneously or subsequently with formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the active compound in an organic solvent (such as butanol, cyclohexanone, dimethylformamide, xylene, or another relatively high-boiling aromatic compound or hydrocarbon) or In the organic solvent mixture, and add one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium alkylarylsulfonates, such as 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 (e.g. sorbitan fatty acid esters or polyoxyethylene sorbitan esters, e.g. polyoxyethylene sorbitan fatty acid esters).

Dedusting products are obtained by grinding the active compound with finely divided solids, such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates can be based on water or oil. It can be prepared, for example, by wet-milling by means of a commercial bead mill, optionally adding surfactants as, for example, already listed above for the other formulation types.

Emulsions such as oil-in-water emulsions (e.g., oil-in-water emulsions ( EW)).

Active compound concentrates can be applied to carriers such as sand, kaolinite or granules by spraying the active compound onto absorbent granular inert materials or by applying the active compound concentrates to carriers such as sand, kaolinite or granules with the aid of adhesives such as polyvinyl alcohol, sodium polyacrylate or mineral oil. like inert material) to produce granules on the surface. The suitable active compounds can also be granulated in the customary manner to produce fertilizer granules, if desired in the form of mixtures containing fertilizers.

Water-dispersible granules are generally produced by customary processes such as spray drying, fluid bed granulation, pan granulation, mixing with high-speed mixers and extrusion without the use of solid inert materials.

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

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

The agricultural chemical formulation, preferably the herbicidal or plant growth regulating composition of the present invention preferably comprises a total amount of 0.1% by weight to 99% by weight, preferably 0.5% by weight to 95% by weight, especially preferably 1% by weight to 90% by weight, particularly preferably 2% to 80% by weight, of active compounds of general formula (I) and their salts.

In wettable powders, the active compound concentration is, for example, about 10% to 90% by weight, the remainder of 100% by weight consisting of customary formulation components. In emulsifiable concentrates, the active compound concentration may be from about 1% to 90% by weight and preferably from 5% to 80% by weight. Formulations in dust form comprise 1% to 30% by weight of active compound, preferably usually 5% to 20% by weight of active compound; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% by weight. % by weight to 50% by weight of active compound. In the case of water-dispersible granules, the active compound content depends partly on whether the active compound is in liquid or solid form and which granulation assistants, fillers etc. are used. In water-dispersible granules, for example, the active compound content is between 1% and 95% by weight, preferably between 10% and 80% by weight.

In addition, the active compound formulations mentioned include, if appropriate, the respective customary tackifiers, wetting agents, dispersants, emulsifiers, penetrating agents, preservatives, antifreeze agents and solvents, extenders, carriers and dyes, disinfectants, Foaming agents, evaporation inhibitors and reagents affecting pH and viscosity. Examples of formulation aids are described inter alia in "Chemistry and Technology of Agrochemical Formulations", edited by D.A. Knowles, Kluwer Academic Publishers (1998).

The compounds of general formula (I) or their salts can be used as they are or in combination with other insecticidally active compounds (such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or Growth regulators) are used in the form of preparations (formulations) in combination, for example in the form of finished formulations or in the form of tank mixes. Combination formulations may be prepared based on the formulations mentioned above, taking into account the physical properties and stability of the active compounds to be combined.

Active compounds which can be employed in mixture formulations or tank mixes in combination with the compounds of the general formula (I) according to the invention are, for example, based on, for example, acetyl lactate synthase, acetyl-CoA carboxylase, cellulose synthase , enolpyruvate shikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoene dehydrogenase, photosystem I, photosystem II, protoporin Compounds known to be active in the inhibition of phylinogen oxidase, such as, for example, 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.

Particular attention is paid to the selective control of harmful plants in crops of useful plants and ornamental plants. Although the compounds of the general formula (I) according to the invention have shown very good to sufficient selectivity in a large number of crops, in principle, in some crops and especially also in admixture with other less selective herbicides, Phytotoxicity may occur on crop plants. In this connection, combinations of compounds of the general formula (I) according to the invention comprising compounds of the general formula (I) or combinations thereof with other herbicides or insecticides and safeners are of particular interest. Safeners used in detoxifying effective amounts reduce the use of, for example, economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, Phytotoxic side effects of herbicides/insecticides in good ground cereals).

The weight ratio of herbicide (mixture) to safener generally depends on the herbicide application rate and the efficacy of the safener in question and can vary within wide limits (for example between 200:1 and 1:200, preferably 100 :1 to 1:100, especially in the range of 20:1 to 1:20). Similar to compound (I) or mixtures thereof, safeners can be formulated with other herbicides/pesticides and provided and employed as finished formulations or tank mixes with herbicides.

At the time of application, commercially available herbicides or herbicide/safener formulations, for example in wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, are diluted, if appropriate, in the customary manner. circumstances. Dust-form formulations, granules for soil application or granules for spreading and sprayable solutions are generally not diluted further with other inert substances before application. the

The application amount of the compound of general formula (I) and/or its salt is affected to some extent by external conditions (such as temperature, humidity, etc.). Herein, the applied amount may vary within wide limits. When applied as a herbicide to control harmful plants, the total amount of the compound of general formula (I) and/or its salt is preferably in the range of 0.001 kg/ha to 10.0 kg/ha, preferably 0.005 kg/ha to 5 kg/ha, more preferably in the range of 0.01 kg/ha to 1.5 kg/ha, especially preferably in the range of 0.05 kg/ha to 1 kg/ha. This applies to pre-emergence as well as post-emergence applications. the

The compounds of general formula (I) and/or their salts are used as plant growth regulators (for example as crop plants (as mentioned above, preferably cereal plants such as wheat, barley, rye, triticale, millet , japonica rice or corn) when the total application rate is preferably in the range of 0.001 kg/ha to 2 kg/ha, preferably in the range of 0.005 kg/ha to 1 kg/ha, especially In the range of 10 g/ha to 500 g/ha, very particularly in the range of 20 g/ha to 250 g/ha. This applies to pre-emergence as well as post-emergence applications. the

Can be applied as a culm stabilizer at various plant growth stages. Preferably, the application is carried out at the onset of longitudinal growth, for example after the tillering stage.

Alternatively, application as a plant growth regulator may also be by treatment of the seed, including various techniques for seed dressing and seed coating. Here, the application rate depends on the specific technology and can be determined in preliminary tests. the

Active compounds which can be employed in combination with the compounds of general formula (I) according to the invention in the compositions according to the invention (for example in mixed formulations or tank mixes) are, for example, based on (for example) acetyl lactate synthase, acetyl- CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoene dehydrogenase, photosystem I. Compounds known to be active in the inhibition of photosystem II, protoporphyrinogen oxidase, such as, for example, Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and described in the Royal Soc. of Chemistry, 2012 and references cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active compounds, where the compounds are used under the "common names" of the International Organization for Standardization (ISO) or using the chemical Name or use code number to name. It always covers all application forms (eg acids, salts, esters but also all isomeric forms, eg stereoisomers and optical isomers), even if not explicitly mentioned.

Examples of such herbicidal mixed partners are: acetochlor, acifluorfen, methyl acifluorfen, acifluorfen sodium, aclonifen, acifluorfen Alachlor, allidochlor, alloxydim, sodium dichloride, ametryn, amicarbazone, amidochlor, sulfuron-methyl (amidosulfuron), 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, cyclo Propyralid Potassium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid-Dimethylammonium, Aminopyralid-2-Hydroxy(tripropyl)amine, Aminopyralid Amitrole, ammoniumsulfamate, anilofos, asulam, asulam potassium, asulam sodium, atrazine, azafenidin, tetrazolium Azimsulfuron, beflubutamid, (S)-(-)-flubutachlor, flubutachlor-M, benazolin, benazolin-ethyl ), bensulfuron-dimethylammonium, benfluralin potassium, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, Bensulide, bentazone, bentazone sodium, benzobicyclon, benzofenap, bicyclopyron, bifenox, dipropylamine Phosphate (bilanafos), bialafosine sodium, bipyrazone, bispyribac, bispyribac sodium, bixlozone, (bromacil), lithium benzotrione, benzene Sodium oxazone, bromobutide, bromofenoxim, bromoxynil, bromoxynil butyrate, bromoxynil potassium, bromoxynil heptanoate and bromoxynil octanoate, hydroxy Busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim , butylate, cafenstrole, cambendichlor, carbetamide, carfentrazone, carfentrazone-ethyl, fentrazone Chloramben, Metrazil Ammonium, Metrazil Glycolamine, Methazone, Sodium Metrazil, Sodium Metrazil, Chlorbromuron, Chlorfenac, Weedgrass Grammonium, Sodium, Chlorfenprop, Methyl Avenate, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal, chlorthal-dimethyl, monomethyl Tacgrass, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-ciclofen (ie (1R,2S,4S) -4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane), exo-(-)-cyclohexyl Ether (i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane ), cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clodinafop-propargyl, clomazone , clomeprop, clopyralid, methyl clopyralid, clopyralid-olamine, clopyralid potassium, clopyralid-tripodamine (clopyralid- tripomine), cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, grass Cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cyclooxydim, cyhalofop, cyhalofop (cyhalofop-butyl), cyprazine, 2,4-D (including its ammonium, butoxyethyl, -butyl, choline, diethylammonium, -dimethylammonium, -glycolamine, -2-propyl butyl ether, -dodecyl ammonium, 2-ethylhexyl, ethyl, 2-ethylhexyl, heptyl ammonium, isobutyl, isooctyl, isopropyl, isopropyl ammonium, Lithium, methyl heptyl ester, methyl, potassium, myristyl ammonium, triethyl ammonium, triisopropanol ammonium, 2-hydroxy (tripropyl) amine and triethanolamine salts), 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl, 2,4-DB potassium and 2,4-DB-sodium, diuron (daimuron, dymron), dalapon (dalapon), calcium dazomet, magnesium dazomet, sodium dazomet, dazomet, sodium dazomet, n-decyl alcohol, 7-deoxy-D-sedoheptulose, Desmedipham, detosyl-pyrazolate (DTP), dicamba and its salts (such as dicamba-diaminopropylmethylamine (biproamine), dicamba-N,N- Bis(3-Aminopropyl)methylamine, Dicamba-Butoxyethyl, Dicamba-Choline, Dicamba-Diethylene Glycolamine, Dicamba-Dimethylammonium, Dicamba-Diethanolamine Ammonium, Wheat Straw Dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl, dicamba-monoethanolamine, dicamba-olamine, dicamba potassium, dicamba sodium, dicamba-triethanolamine), 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, 2,4-dichlorprop, 2,4-dichlorprop-butoxyethyl, 2,4-dichlorprop Acid-Dimethylammonium, 2,4-Dipropionate-2-Ethylhexyl, 2,4-Dipropionate-Ethyl Ammonium, 2,4-Dipropionate-Isooctyl, 2,4-Dipropionate Acid-Methyl, Potassium 2,4-Dipropionate, Sodium 2,4-Dipropionate, 2,4-Dipropionate-P, 2,4-Dipropionate-P-Dimethylammonium, 2,4 -Diclopropionate-P-2-ethylhexyl ester, 2,4-Dipropionate-P potassium, 2,4-Dichlorpropionate sodium, dichlorophenoxypropionate (diclofop), diclofop (diclofop -methyl), dichlorophenoxypropionic acid-P, dichlorophenoxypropionic acid-P-methyl (diclofop-P-methyl), diclosulam, difenzoquat, formazan Oatquat Sulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr Sodium, Dimefuron, Dimepiperate, Dimesulfazet, Dimethyrone Dimethachlor, dimethamethryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb ), dimethophanol acetate, diphenamid, diquat, diquat-dibromid, diquat dihydrochloride, dithiopyr, Diuron, DNOC, DNOC-ammonium, DNOC potassium, DNOC sodium, endothal (endothal), endothal-diuron, endothal dipotassium, endothal disodium, epithil ( Epyrifenacil (S-3100), EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethametsulfuron ( Ethiozin), Ethofumesate, Ethoxyfen, Ethoxyfen-ethyl, Ethoxysulfuron, Etobenzanid, F-5231 (that is, N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]benzene group}ethanesulfonamide), F-7967 (that is, 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl- 6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione), fenoxaprop-p-p, fenoxaprop-p-P, ethyl fenoxaprop-p- ethyl), fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, tetrazolamide (fentrazamide), wheat straw fluoride (flamprop), isopropyl wheat straw fluoride, methyl wheat straw fluoride, isopropyl wheat straw fluorine-M, methyl wheat straw fluoride-M, flazasulfuron, florasulam ( florasulam), florpyrauxifen, benzyl fluazifop, fluazifop, butyl fluazifop, methyl fluazifop, fluazifop-P , Butyl fluazifop-P, flucarbazone, flucarbazone sodium, flucetosulfuron, fluchloralin, flufenacet, fluperazine flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin ), fluometuron, flurenol, flurenol-butyl, flurenol-dimethylammonium and flurenol-methyl , Fluoroglycofen, Fluoroglycofen-ethyl, Flupropanate, Sodium Fluoropropionate, Flupyrsulfuron, Fluorosulfuron- Flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-butoxypropyl, fluroxypyr-butometyl fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen sodium, formamide Foramsulfuron, foramsulfuron-methyl sodium salt, fosamine, woodphosinate-ammonium, glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate- Ammonium, L-glufosinate sodium, glufosinate-P sodium, glufosinate-P-ammonium, glyphosate, ammonium glyphosate, isopropyl ammonium glyphosate, diammonium glyphosate, diammonium glyphosate Ammonium methyl, potassium glyphosate, sodium glyphosate, sesquisodium glyphosate and glyphosate-trimethylsulfur salt, H-9201 (that is, O-ethylisopropylaminothiophosphoric acid O- (2,4-Dimethyl-6-nitrophenyl) ester), halauxifen, halauxifen-methyl, halosafen, chloropyrazole Halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop- ethoxyethyl), haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, Fluazoxyfop sodium, hexazinone, HNPC-A8169 (also known as (2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propane Prop-2-yn-1-yl acetate), HW-02 (i.e. 1-(dimethoxyphosphoryl) ethyl-(2,4-dichlorophenoxy)acetate), Heda Hydantocidin, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox, imazapic, imazapic Herbal ammonium, imazapyr, imazethapyr-isopropylammonium, imazaquin, imazaquin-ammonium, methyl imazethapyr, imazethapyr Niacin-ammonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, methyl iodosulfuron, iodosulfuron-methyl-sodium ), ioxynil, lithium ioxynil, ioxynil-octanoate, potassium ioxynil and sodium ioxynil, ipfencarbazone, isoproturon, isoproturon Isouron, isoxaben, isoxaflutole, karbutilate, KUH-043 (that is, 3-({[5-(difluoromethyl)- 1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2- Oxazole), Ketospiradox, Ketospira Potassium, Lactofen, Lancotrione, Lenacil, Linuron, MCPA, MCPA- Butoxyethyl, MCPA-butyl, MCPA-dimethylammonium, MCPA-diolamine, MCPA-2-ethylhexyl, MCPA-ethyl, MCPA-isobutyl, MCPA-isooctyl, MCPA- Isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-alcoholamine, MCPA potassium, MCPA sodium and MCPA-triethanolamine, MCPB, MCPB-methyl, MCPB-ethyl and MCPB sodium, 2 methyl 4 chloride Mecoprop, mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-butotyl Acid-2-ethylhexyl, 2-methyl-4-chloropropionate-ethyl, 2-methyl-4-chloropropionate-isooctyl, 2-methyl-4-chloropropionate-methyl, 2-methyl-4-chloropropionate-potassium, 2-methyl-4-chloropropionate Sodium 4-chloropropionate and mecoprop-P-triethanolamine, mecoprop-P, butoxyethyl-mecoprop-P-butotyl, mecoprop-P-butotyl 2-methyl-4-chloropropionate-dimethylammonium, 2-ethylhexyl ethyl 2-methyl-4-chloropropionate and potassium 2-methyl-4-chloropropionate, mefenacet, mefluidide, fluorine Sulfo-diolamine, trisulfuron potassium, mesosulfuron, mesosulfuron-methyl, mesosulfuron-methyl, mesotrione sodium salt, mesotrione, formazan methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methyl Methabenzthiazuron, Methiopyrsulfuron, Methiozolin, Methyl isothiocyanate, Metobromuron, Metolachlor, S-Pretilachlor , metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, green valley Monolinuron, monosulfuron, monosulfuron methyl, MT-5950 (that is, N-(3-chloro-4-(1-methylethyl)phenyl)-2- Methylpentamide), NGGC-011, napropamide, NC-310 (that is, 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxy pyrazole), NC-656 (ie 3-[(isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5- (trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide), neburon (neburon), nicosulfuron (nicosulfuron), nonanoic acid ( nonanoic acid, pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl ), oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, paraquat dichloride dichloride), dimethylsulfuric acid, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone , pethoxamid, petroleum, phenmedipham, ethyl phenmedipham, picloram, picloram-dimethylammonium, picloram-2-ethylhexyl ester, isooctyl poison Picloram, methyl picloram, picloram-olamine, picloram potassium, picloram-triethylammonium, picloram-2-hydroxy(tripropyl)amine, picloram-triethanolamine, picolinafen ), pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine ), profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, aniline (propham), propisochlor, propoxycarbazone, propoxycarbazone sodium, propyrisulfuron, propyzamide, prosulfocarb, Prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate) , Pyrazosulfuron, Pyrazosulfuron-ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-isopropyl, Propoxyfen ( pyribambenz-propyl), pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, formazan Pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrimiabac sodium, pyroxasulfone, pyroxsulam, quinclorac, quinclorac-dimethylammonium, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl , quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM201 (that is, 1-{2-chloro-3 -[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}hexahydropyridin-2-one), Rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulfone Sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249 (also known as 5-[2 -chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl ester), SYP-300 (that is, 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazine -6-yl]-3-propyl-2-sulfanyl-imidazolidine-4,5-dione), 2,3,6-TBA, TCA (trichloroacetic acid) and their salts (e.g. TCA-ammonium , TCA calcium, ethyl TCA, TCA magnesium, TCA sodium), tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, Terbucarb, terbumeton, terbutylazine, terbutryn, tetflupyrolimet, thaxtomin, thenylchlor ), thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, grass (thiobencarb), tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tricamba (tri -allate), triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, butoxyethyl Triclopyr-methyl, Triclopyr-methyl-choline, Triclopyr-ethyl, Triclopyr-triethylammonium, trietazine, trifloxysulfuron, trifluxysulfuron sodium, Terry Trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, aquamone ( vernolate), XDE-848, ZJ-0862 (i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline), 3-(2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1 (2H)-yl) Phenyl)-5-methyl-4,5-dihydroisoxazole-5-ethyl carboxylate, [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6- Dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]ethyl acetate, 3-chloro- 2-[3-(Difluoromethyl)isoxazolyl-5-yl]phenyl-5-chloropyrimidin-2-yl ether, 2-(3,4-dimethoxyphenyl)-4- [(2-Hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazin-3( 2H )-one, 2-({2-[(2-methyl Oxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazole-4- Base) (3,3,4-trimethyl-1,1-dioxo-2,3-dihydro-1-benzothiophen-5-yl)methanone, 1-methyl-4-[ (3,3,4-Trimethyl-1,1-dioxo-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-ylpropane- 1-sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl Base}-1-methyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate, 4-amino-3-chloro-5-fluoro-6 -(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid cyanomethyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole -6-yl)pyridine-2-carboxylic acid prop-2-yn-1-yl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) Pyridine-2-carboxylic acid methyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, 4-amino-3- Benzyl chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro -1H-indol-6-yl)pyridine-2-carboxylic acid ethyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indole-6- base) pyridine-2-carboxylic acid methyl ester, 6-(1-acetyl-7-fluoro-1H-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylic acid Methyl ester, 4-amino-3-chloro-6-[1-(2,2-dimethylpropionyl)-7-fluoro-1H-indol-6-yl]-5-fluoropyridine-2 -Methyl formate, 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl]pyridine-2-carboxylic acid Methyl ester, potassium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, potassium 4-amino-3-chloro-5- Fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate sodium, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6 -yl)pyridine-2-carboxylic acid butyl ester, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 3-(5-th Tributyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidine-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridine-2- Base] -4-hydroxyl-1-methylimidazolidine-2-one, 4-hydroxyl-1-methoxyl-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl] Imidazolidine-2-one, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylbenzene base) quinazoline-2,4(1H,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohexyl-1- En-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-( Lin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyrazine- 1-onium salts (with anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-1-ium salts (with Anions such as chloride, acetate or trifluoroacetate), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazin-1-ium salts (with anions such as chloride, acetate or Anions such as trifluoroacetate), 4-(pyridazin-3-yl)-1-(2-sulfoethyl)pyridazin-1-ium salts (with anions such as chloride, acetate or trifluoroacetate) ).

Examples of plant growth regulators as possible mixing partners: Cleaving acid, acibenzolar, acibenzolar-S-methyl, 1-aminocyclopropan-1-ylcarboxylate Acids and their derivatives, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, bikinin, brassinolide, ethyl brassinolide Lactones, L-canavanic acid, catechins, chitooligosaccharides (CO; CO differs from LCO in that it lacks the characteristic pendant fatty acid chains of LCO. CO (sometimes called N-acetyl chitosan Tetraoligosaccharides) are also composed of GlcNAc residues, but have different properties that make them different from chitin molecules [(C ₈ H ₁₃ NO ₅ ) _n , CAS No. 1398-61-4] and chitosan molecules [(C ₅ H ₁₁ NO ₄ ) _n , side chain modification of CAS No. 9012-76-4]), chitin compound, chlormequat chloride, cloprop, cyclanilide ), 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, sodium formyl, n-decyl alcohol, dikegulac, sodium furoate , endothal (endothal), endothal dipotassium, endothal disodium and endothal-mono(N,N-dimethylalkylammonium), ethephon, flumetralin , flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, gibberellic acid, trinexamide (inabenfide), indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid, or Its derivatives (e.g. methyl jasmonate), lipo-chitooligosaccharides (LCO are sometimes called symbiotic nodulation (Nod) signals (or Nod factors) or Myc factors, which consist of β-1,4 linked The oligosaccharide backbone of N -acetyl-D-glucosamine ("GlcNAc") residues consists of an N-linked fatty acyl chain condensed at the non-reducing end. As understood in the art, each LCO differs in that The number of GlcNAc residues in the main chain, the length and saturation of the aliphatic acyl chain and the substitution of reducing and non-reducing sugar residues), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic acid Hydrazine, mepiquat chloride, mepiquat pentaboronic acid, 1-methylcyclopropene, 3'-methyl ionoic acid, 2-(1-naphthyl)acetamide, 1-naphthalene Glycoacetic acid, 2-naphthyloxyacetic acid, nitrophenolate-mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4 -Phenylbutyric acid, N-phenylphthalide, prohexadione, prohexadione calcium, prohydrojasmon, salicylic acid, methyl salicylate, strigod Strigolacton, Tecnazene, Thidiazuron, Triacontanol, Trinexapac, Trinexapac-ethyl, Tesdifor (tsitodef), uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl) -9H -purin-6-amine.

Suitable combination partners for the compounds of general formula (I) according to the invention also include, for example, the following safeners: S1) Compounds from the group of derivatives of heterocyclic carboxylic acids: S1 ^a ) Dichlorophenylpyrazoline- Compounds of the 3-formic acid type (S1 ^a ), preferably compounds such as: 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazole Line-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) ( "Mefenpyr-diethyl") and related compounds as described in WO-A-91/07874; S1 ^b ) derivatives of dichlorophenylpyrazole carboxylic acid (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 esters (S1-4) and related compounds as described in EP-A-333131 131 and EP-A-269806; S1 ^c ) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 ^c ), preferably compounds such as: 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S1-5), 1-(2-chlorophenyl) - methyl 5-phenylpyrazole-3-carboxylate (S1-6) and related compounds as described, for example, in EP-A-268554; S1 ^d ) compounds of the triazole carboxylic acid type (S1 ^d ), compared to Preferably compounds such as the following: fenchlorazole (ethyl ester) (ie 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole -3-ethyl carboxylate (S1-7)) and related compounds (as described in EP-A-174562 and EP-A-346620); S1 ^e ) 5-benzyl- or 5-phenyl-2-iso Compounds of the oxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (S1 ^e ), preferably compounds such as: 5-(2,4-di Chlorobenzyl)-2-isoxazoline-3-carboxylic acid ethyl ester (S1-8) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds (such as described in WO-A-91/08202) or 5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10) or 5,5-diphenyl-2-isoxazoline-3- Ethyl formate (S1-11) (“isoxadifen-ethyl”) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12 ) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13) (as described in patent application WO-A-95/07897) .

S2) Compounds from the group of 8-quinolinyloxy derivatives (S2): ^S2a ) Compounds of the 8-quinolinyloxyacetic acid type ( ^S2a ), preferably (5-chloro-8-quinolinyloxy base) 1-methylhexyl acetate ("cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolineoxy) 1,3-dimethylbutan-1- Base ester (S2-2), (5-chloro-8-quinolineoxy)acetic acid 4-allyloxybutyl ester (S2-3), (5-chloro-8-quinolineoxy)acetic acid 1-allyloxyprop-2-yl ester (S2-4), ethyl (5-chloro-8-quinolineoxy)acetate (S2-5), 5-chloro-8-quinolineoxy Methyl acetate (S2-6), (5-chloro-8-quinolineoxy) allyl acetate (S2-7), (5-chloro-8-quinolineoxy) acetic acid 2-(2- Propyleneiminooxy)-1-ethyl ester (S2-8), (5-chloro-8-quinolineoxy) acetic acid 2-oxopropan-1-yl ester (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 also (5-chloro-8-quinolinyloxy)acetic acid ( S2-10), their hydrates and salts (such as their lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, permeic or phosphonium salts) (as described in WO-A-2002/34048 ); S2 ^b ) Compounds of the (5-chloro-8-quinolineoxy) malonate type (S2 ^b ), preferably compounds such as: (5-chloro-8-quinolineoxy) propanedi Diethyl (5-chloro-8-quinolinyloxy)malonate, diallyl (5-chloro-8-quinolinyloxy)malonate, ethyl (5-chloro-8-quinolinyloxy)methylmalonate and related compounds (such as EP-A-0 582 198).

S3) Active compounds of the dichloroacetamide type (S3), which are usually used as pre-emergence safeners (soil-acting safeners), e.g. "Dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (from Stauffer, S3-2), "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (from Stauffer, S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(1,3-dioxolanyl-2-yl)methyl]dichloroacetamide) (from PPG Industries, S3-5) , "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (from Sagro-Chem, S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-azaspiro[4,5]decane) (from Nitrokemia or Monsanto, S3-7), "TI-35" (1-dichloroacetylazepane) (from TRI-Chemical RT, S3-8), "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) Also and its (R)-isomer (S3-11).

S4) Compounds from the class of amidessulfonamides (S4): ^S4a ) N-acylsulfamides of formula ( ^S4a ) and salts thereof, as described in WO-A-97/45016, Where R _A ¹ is (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, wherein the last _two groups are from halogen, (C ₁ -C ₄ )-alk Substituents of the group of oxy, (C ₁ -C ₆ )-haloalkoxy and (C ₁ -C ₄ )-alkylthio groups are substituted and in the case of cyclic groups also by (C ₁ -C ₄ ) -Alkyl and (C ₁ -C ₄ )-haloalkyl substitution; R _A ² is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, CF ₃ ; m _A is 1 or 2; v _A is 0, 1, 2 or 3; S4 ^b ) 4-(benzoylsulfamoyl) benzamide type compounds of formula (S4 ^b ) and salts thereof (such as WO -A-99/16744): wherein R _B ¹ and 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, R _B ³ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl or (C ₁ -C ₄ )-alkoxy and m _B is 1 or 2, such as those with the following characteristics: R _B ¹ = cyclopropyl, R _B ² = hydrogen and (R _B ³ ) = 2-OMe ("cyclopropanesulfamide", S4-1), R _B ¹ = cyclopropyl, R _B ² = hydrogen and (R _B ³ ) = 5-Cl-2-OMe (S4-2), R _B ¹ = ethyl, R _B ² = hydrogen and (R _B ³ ) = 2-OMe (S4-3), R _B ¹ = isopropyl, R _B ² = hydrogen and (R _B ³ ) = 5-Cl-2-OMe (S4-4) and R _B ¹ = isopropyl , R _B ² = hydrogen and (R _B ³ ) = 2-OMe (S4-5); S4 ^c ) compounds from the class of benzoylsulfamoylphenyl ureas of formula (S4 ^c ) (such as EP -A-365484): Where R _C ¹ and 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, R _C ³ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, CF ₃ and m _C is 1 or 2; for example 1- [4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl) Base) phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; S4 ^d ) Compounds of the N-phenylsulfonylterephthalamide type of formula ( ^S4d ) and their salts (which are known, for example, from CN 101838227): Where R _D ⁴ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, CF ₃ ; m _D is 1 or 2; R _D ⁵ is hydrogen, (C ₁ - C ₆ )-Alkyl, (C ₃ -C ₆ )-Cycloalkyl, (C ₂ -C ₆ )-Alkenyl, (C ₂ -C ₆ )-Alkynyl or (C ₅ -C ₆ )-Cyclo Alkenyl.

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

S6) Active compounds from the class of 1,2-dihydroquinoxalin-2-ones (S6), for example 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline- 2-keto, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thiophene base)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-di Hydroquinoxalin-2-ones (as described in WO-A-2005/112630).

S7) Compounds from the class of diphenylmethoxyacetic acid derivatives (S7), such as methyl diphenylmethoxyacetate (CAS registry number: 41858-19-9) (S7-1), diphenyl Ethyl methoxyacetate or diphenylmethoxyacetic acid (as described in WO-A-98/38856).

S8) a compound of formula (S8), as described in WO-A-98/27049, The symbols and indices are defined as follows: R _D ¹ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy, R _D ² is hydrogen or (C ₁ -C ₄ )-alkyl, R _D ³ is hydrogen, (C ₁ -C ₈ )-alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ )-alkynyl or aryl, wherein each of the above-mentioned carbon-containing groups is unsubstituted or consists of one or more, preferably up to three Free halogen and alkoxy groups are substituted by the same or different groups; or salts thereof, n _D is an integer from 0 to 2.

S9) Active compounds from the class of 3-(5-tetrazolylcarbonyl)-2-quinolinones (S9), for example 1,2-dihydro-4-hydroxy-1-ethyl-3-(5- Tetrazolylcarbonyl)-2-quinolinone (CAS registry number: 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)- 2-quinolinone (CAS registry number: 95855-00-8) (as described in WO-A-199/000020);

S10) Compounds of formula (S10 ^a ) or (S10 ^b ) as described in WO-A-2007/023719 and WO-A-2007/023764: wherein R _E ¹ is halogen, (C ₁ -C ₄ )-alkyl, methoxy, nitro, cyano, CF ₃ , OCF ₃ Y _E , Z _E are independently O or S, n _E is 0 to Integer of 4, R _E ² is (C ₁ -C ₁₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₃ -C ₆ )-cycloalkyl, aryl, benzyl, halo Benzyl, R _E ³ is hydrogen or (C ₁ -C ₆ )-alkyl.

S11) Active compounds of the oxyimino compound type (S11), which are called seed dressing agents, for example "Oxabetrinil" ((Z)-1,3-dioxolanyl-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), known as Safener for triticale/sorghum seed dressing against pretilachlor damage, "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolanyl-2-yl Methyl)oxime) (S11-2), known as triticale/sorghum seed dressing safener against pretilachlor damage, and "cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known to protect against pretilachlor damage Safener for triticale/sorghum seed dressing.

S12) Active compounds from the class of isothiol ketones (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate Esters (CAS Reg. No.: 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361.

S13) One or more compounds from the group (S13): "Naphthalic anhydride" (1,8-naphthalic anhydride) (S13-1), known as a corn seed dressing safener against thiocarbamate herbicide damage, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as the safener of pretilachlor in sown japonica rice, "flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as resistant to alachlor and pretilachlor Damaged triticale/sorghum seed dressing safener, "CL 304415" (CAS registration number: 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-chromen-4-acetic acid) (S13-4) (from American Cyanamid), known as a corn safener against imidazolinone damage, "MG 191" (CAS registry number: 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) (from Nitrokemia), which known as corn safener, "MG 838" (CAS registration number: 133993-74-5) (1-Oxa-4-azaspiro[4.5]decane-4-dithiocarboxylate 2-propenyl) (S13-6) (from Nitrokemia) "Disulfoton" (O,O-diethyl dithiophosphate S-2-ethylthioethyl ester) (S13-7), "Dietholate" (O,O-diethyl ester O-phenyl phosphorothioate) (S13-8), "Mephenate" (4-chlorophenyl methylcarbamate) (S13-9).

S14) Active compounds that have a safener effect on crop plants (such as japonica rice) in addition to their herbicidal action against weeds, such as "dimepiperate" or "MY-93" ( S -1-phenylethyl Hexahydropyridine-1-thiocarboxylate 1-methyl ester), known as a japonica rice safener against damage by the herbicide molinate, "daimuron" or "SK 23" (1- (1-methyl-1-phenylethyl)-3-p-tolylurea), known as a japonica rice safener against imazosulfuron (imazosulfuron) herbicide damage, "cumyluron (cumyluron) ” = “JC-940” (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), which is known to resist some Japonica rice safener for herbicide damage, "methoxyphenone" or "NK 049"(3,3'-dimethyl-4-methoxybenzophenone), which is known to resist some herbicide damage Japonica rice safener, "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) (from Kumiai, CAS Reg. No.: 54091-06-4), which is known as Japonica rice resistant to some herbicide damage Safener.

S15) Compound of formula (S15) or its tautomers: As described in WO-A-2008/131861 and WO-A-2008/131860 wherein R _H ¹ is (C ₁ -C ₆ )-haloalkyl and R _H ² is hydrogen or halogen, and R _H ³ , R _H ⁴ are each independently hydrogen, (C ₁ -C ₁₆ )-alkyl, (C ₂ -C ₁₆ )-alkenyl or (C ₂ -C ₁₆ )-alkynyl, wherein each of the latter three groups are unsubstituted or substituted by one or more groups from the following groups: halogen, hydroxy, 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 )-Alkane Oxy]carbonyl, [(C ₁ -C ₄ )-haloalkoxy]carbonyl, unsubstituted or substituted (C ₃ -C ₆ )-cycloalkyl, unsubstituted or substituted phenyl and unsubstituted Substituted or substituted heterocyclyl, or (C ₃ -C ₆ )-cycloalkyl, (C ₄ -C ₆ )-cycloalkenyl, fused on one side of the ring to 4 to 6 member saturated or unsaturated (C ₃ -C ₆ )-cycloalkyl of a saturated carbocycle or (C ₄ -C ₆ )-cycloalkenyl of a 4- to 6-membered saturated or unsaturated carbocycle fused on one side of the ring, wherein the latter 4 Each of the groups is unsubstituted or substituted with one or more groups from the following groups: halogen, hydroxy, 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 heterocyclyl, or R _H ³ is (C ₁ -C ₄ )-alkoxy, (C ₂ -C ₄ )-alkenyloxy, (C ₂ -C ₆ )-alkynyloxy or (C ₂ -C ₄ )-haloalkoxy and R _H ⁴ is hydrogen or (C ₁ -C ₄ )-alk group, or R _H ³ and R _H ⁴ together with the directly bonded nitrogen atom are 4 to 8 membered heterocyclic rings, which may contain other ring heteroatoms in addition to the nitrogen atom, preferably up to two from N, O and Other ring heteroatoms of the group S, which are unsubstituted or composed of one or more of halogen, cyano, nitro, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl , (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-halogenated alkoxy and (C ₁ -C ₄ )-alkylthio groups.

S16) Active compounds which are mainly used as herbicides and which 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 (2-methyl-4-chloropropionic acid), 4-(2,4-Dichlorophenoxy)butanoic acid (2,4-DB), (4-Chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-Chloro-o-tolyloxy)butanoic acid, 4-(4-Chlorophenoxy)butanoic acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor-ethyl).

The preferred safeners combined with the compound of general formula (I) of the present invention and/or its salt, especially with the compound of formula (I-001) to (I-041) and/or its salt are: cloquintocetam, cyclopropane Sulfonamide, Ethoxazole, Ethyl Difenoxafe, Mefenpyr, Triclopyr, Benuron, S4-1 and S4-5, and the best safeners are: Jieduquine, Cyprosulfamide, isoxadifen, and mefenpyr-ethyl.

Biological Examples: The following abbreviations are used in the examples and tables below: Pesticide plants tested : ABUTH: Abutilon theophrasti ALOMY: Alopecurus myosuroides AMARE Amaranthus retroflexus DIGSA: Chinese crabgrass (Digitaria sanguinalis) ECHCG: Echinochloa crus-galli KCHSC: Kochia scoparia LOLRI: Lolium rigidum MATIN: Matricaria inodora POAAN: Poa annua SETVI: Setaria viridis STEME: Chickweed (Stellaria media) VERPE: Arabian mother-in-law (Veronica persica)

A. Pre-emergence herbicide The seeds of the monocotyledonous and dicotyledonous weed plants were sown in sandy loam in plastic pots (double sowing, one monocotyledonous weedy plant and one dicotyledonous weedy plant per pot), and covered with soil. The compound of the invention (formulated as a wettable powder (WP) or emulsifiable concentrate (EC)) is applied to the surface of the covering soil in the form of an aqueous suspension or emulsion at an application rate of 600 liters of water/ha (converted) On, and add 0.5% additives. After treatment, the pots were placed in a greenhouse and kept under optimal growth conditions for the test plants.

Visual grading of damage to the test plants compared to the untreated control was carried out after about 3 weeks (herbicidal effect (in %): 100% effect = plant is dead, 0% effect = plant as control).

Tables A1 to A12 below show the effect of selected compounds of general formula (I) in table 1 on various harmful plants and the corresponding application rates of 1280 g/ha (obtained by the experimental procedure mentioned above). Table A1 instance number Dose [g/ha] ABUTH I-034 1280 90 I-001 1280 100 I-008 1280 90 I-011 1280 100 I-025 1280 90 I-040 1280 100 Table A2 instance number Dose [g/ha] ALOMY I-034 1280 100 I-001 1280 90 I-008 1280 90 I-009 1280 90 I-011 1280 100 I-013 1280 100 I-018 1280 90 I-019 1280 90 I-020 1280 90 I-021 1280 100 I-022 1280 90 I-023 1280 90 I-024 1280 100 I-025 1280 90 I-036 1280 90 I-037 1280 90 I-040 1280 90 Table A3 instance number Dose [g/ha] DIGSA I-001 1280 100 I-002 1280 90 I-005 1280 100 I-006 1280 100 I-008 1280 100 I-009 1280 100 I-011 1280 100 I-013 1280 100 I-016 1280 100 I-018 1280 100 I-019 1280 100 I-020 1280 100 I-021 1280 100 I-022 1280 100 I-023 1280 100 I-024 1280 100 I-025 1280 100 I-029 1280 90 I-030 1280 100 I-031 1280 90 I-033 1280 100 I-036 1280 100 I-037 1280 100 I-038 1280 100 I-040 1280 100 Table A4 instance number Dose [g/ha] ECHCG I-034 1280 100 I-001 1280 100 I-002 1280 90 I-005 1280 100 I-006 1280 100 I-008 1280 100 I-009 1280 100 I-011 1280 100 I-013 1280 100 I-019 1280 100 I-020 1280 100 I-021 1280 100 I-022 1280 100 I-023 1280 100 I-024 1280 100 I-025 1280 100 I-030 1280 90 I-031 1280 100 I-033 1280 100 I-036 1280 100 I-037 1280 100 I-038 1280 100 I-040 1280 100 I-041 1280 100 Table A5 instance number Dose [g/ha] KCHSC I-034 1280 90 I-001 1280 90 I-002 1280 90 I-006 1280 90 I-008 1280 100 I-009 1280 90 I-011 1280 90 I-013 1280 90 I-016 1280 90 I-018 1280 90 I-019 1280 90 I-020 1280 90 I-021 1280 90 I-022 1280 90 I-023 1280 100 I-024 1280 90 I-025 1280 90 I-030 1280 90 I-031 1280 90 I-036 1280 90 I-038 1280 90 I-040 1280 100 I-041 1280 90 Table A6 instance number Dose [g/ha] LOLRI I-034 1280 100 I-001 1280 100 I-005 1280 100 I-006 1280 100 I-008 1280 100 I-009 1280 100 I-011 1280 100 I-013 1280 100 I-018 1280 100 I-019 1280 100 I-020 1280 100 I-021 1280 100 I-022 1280 100 I-023 1280 100 I-024 1280 100 I-025 1280 100 I-031 1280 100 I-036 1280 100 I-040 1280 100 I-041 1280 90 Table A7 instance number Dose [g/ha] MATIN I-034 1280 90 I-001 1280 90 I-006 1280 90 I-008 1280 90 I-011 1280 90 I-013 1280 90 I-016 1280 90 I-018 1280 90 I-020 1280 90 I-021 1280 90 I-022 1280 90 I-023 1280 90 I-024 1280 90 I-025 1280 90 I-036 1280 100 I-037 1280 90 I-040 1280 90 Table A8 instance number Dose [g/ha] POAAN I-034 1280 100 I-001 1280 100 I-005 1280 100 I-006 1280 100 I-008 1280 100 I-009 1280 100 I-011 1280 100 I-013 1280 100 I-016 1280 100 I-018 1280 100 I-019 1280 100 I-020 1280 100 I-021 1280 100 I-022 1280 100 I-023 1280 100 I-024 1280 100 I-025 1280 100 I-029 1280 100 I-033 1280 100 I-036 1280 100 I-037 1280 100 I-038 1280 100 I-039 1280 100 I-040 1280 100 I-041 1280 100 Table A9 instance number Dose [g/ha] SETVI I-034 1280 100 I-001 1280 100 I-002 1280 90 I-005 1280 100 I-006 1280 100 I-008 1280 100 I-009 1280 100 I-011 1280 100 I-013 1280 100 I-016 1280 100 I-018 1280 100 I-019 1280 100 I-020 1280 100 I-021 1280 100 I-022 1280 100 I-023 1280 100 I-024 1280 100 I-025 1280 100 I-029 1280 100 I-030 1280 100 I-031 1280 100 I-033 1280 100 I-036 1280 100 I-037 1280 100 I-038 1280 100 I-040 1280 100 I-041 1280 100 Table A10 instance number Dose [g/ha] STEME I-001 1280 100 I-002 1280 90 I-006 1280 90 I-008 1280 90 I-009 1280 90 I-011 1280 90 I-013 1280 90 I-021 1280 90 I-023 1280 90 I-024 1280 90 I-025 1280 90 I-030 1280 90 I-031 1280 90 I-033 1280 90 I-036 1280 90 I-037 1280 90 I-040 1280 100 I-041 1280 90 Table A11 instance number Dose [g/ha] VERPE I-034 1280 90 I-001 1280 90 I-006 1280 90 I-008 1280 90 I-009 1280 90 I-011 1280 90 I-013 1280 90 I-018 1280 90 I-019 1280 90 I-020 1280 90 I-021 1280 90 I-022 1280 90 I-023 1280 90 I-025 1280 90 I-031 1280 90 I-036 1280 90 I-038 1280 90 I-040 1280 90 I-041 1280 90 Table A12 instance number Dose [g/ha] AMARE I-034 1280 90 I-001 1280 100 I-002 1280 90 I-006 1280 90 I-008 1280 90 I-009 1280 90 I-011 1280 90 I-013 1280 90 I-021 1280 90 I-022 1280 90 I-023 1280 90 I-024 1280 90 I-025 1280 90 I-030 1280 90 I-031 1280 90 I-036 1280 90 I-037 1280 90 I-038 1280 90 I-039 1280 90 I-040 1280 90 I-041 1280 90

As shown by the results, at the application rate of 1280 g active ingredient/ha, various general formula (I) compounds of the present invention have very good pre-emergence herbicidal efficacy on a wide range of harmful monocotyledonous and dicotyledonous plants, such weeds Lines (for example) velvetleaf (ABUTH), big ear wheatgrass (ALOMY), retroflexus amaranthus (AMARE), crabgrass (DIGSA), barnyardgrass (ECHCG), Kochia scoparia (KCHSC), rigid ryegrass (LOLRI) , light chamomile (MATIN), bluegrass (POAAN), foxtail (SETVI), chickweed (STEME) and Arabian mother-in-law (VERPE).

B. Post-emergence herbicidal effect Seeds of monocotyledonous and dicotyledonous weed plants were sown in sandy loam in plastic pots (double sowing, one monocotyledonous weed plant and one dicotyledonous weed plant per pot), covered with soil and grown under controlled conditions grow under conditions. 2 to 3 weeks after sowing, the test plants are sprayed at the single leaf stage. The compounds of the invention (formulated as wettable powders (WP) or emulsifiable concentrates (EC)) are sprayed on green plant parts in the form of aqueous suspensions or emulsions at an application rate of 600 liters of water/ha (converted) , and add 0.5% additives. The test plants were placed in a greenhouse and kept under optimal growth conditions for about 3 weeks, and then the formulation effect (herbicidal effect (in %) was assessed visually compared to the untreated control: 100% effect = plant is dead, 0% effect = plant as control).

Tables B1 to B12 below show the effect of selected compounds of the general formula (I) in table 1 on various harmful plants and the corresponding application rates of 1280 g/ha (obtained by the experimental procedure mentioned above). Table B1 instance number Dose [g/ha] ABUTH I-034 1280 90 I-001 1280 100 I-006 1280 90 I-008 1280 90 I-016 1280 90 I-018 1280 90 I-024 1280 90 I-029 1280 90 I-031 1280 90 Table B2 instance number Dose [g/ha] ALOMY I-001 1280 90 I-006 1280 90 I-008 1280 90 I-009 1280 90 I-031 1280 90 Table B3 instance number Dose [g/ha] DIGSA I-001 1280 90 I-006 1280 90 I-008 1280 90 I-009 1280 90 I-011 1280 90 I-018 1280 90 I-019 1280 90 I-021 1280 90 I-022 1280 90 I-025 1280 90 I-036 1280 90 I-040 1280 90 I-041 1280 90 Table B4 instance number Dose [g/ha] ECHCG I-034 1280 90 I-001 1280 90 I-005 1280 90 I-006 1280 90 I-008 1280 100 I-009 1280 90 I-011 1280 90 I-018 1280 90 I-019 1280 90 I-020 1280 90 I-021 1280 90 I-022 1280 90 I-024 1280 90 I-036 1280 100 I-037 1280 90 I-040 1280 90 Form B5 instance number Dose [g/ha] KCHSC I-034 1280 90 I-001 1280 90 I-002 1280 90 I-006 1280 90 I-008 1280 90 I-009 1280 90 I-011 1280 90 I-016 1280 90 I-018 1280 90 I-019 1280 90 I-020 1280 90 I-021 1280 90 I-022 1280 90 I-023 1280 90 I-024 1280 90 I-025 1280 90 I-029 1280 90 I-030 1280 90 I-031 1280 90 I-040 1280 90 I-041 1280 90 Table B6 instance number Dose [g/ha] LOLRI I-034 1280 90 I-006 1280 90 I-008 1280 90 I-011 1280 90 I-021 1280 90 I-024 1280 100 I-030 1280 90 I-031 1280 90 I-036 1280 90 I-040 1280 90 Table B7 instance number Dose [g/ha] MATIN I-008 1280 90 I-034 1280 90 Table B8 instance number Dose [g/ha] POAAN I-034 1280 90 I-001 1280 90 I-005 1280 90 I-006 1280 90 I-008 1280 90 I-009 1280 90 I-011 1280 90 I-013 1280 90 I-016 1280 90 I-018 1280 90 I-019 1280 90 I-021 1280 90 I-022 1280 90 I-024 1280 90 I-025 1280 90 I-031 1280 90 I-033 1280 90 I-036 1280 90 I-037 1280 90 I-040 1280 90 Form B9 instance number Dose [g/ha] SETVI I-034 1280 90 I-001 1280 90 I-005 1280 90 I-006 1280 90 I-008 1280 90 I-011 1280 90 I-013 1280 90 I-019 1280 90 I-021 1280 90 I-022 1280 90 I-024 1280 90 I-029 1280 90 I-036 1280 90 Form B10 instance number Dose [g/ha] STEME I-034 1280 90 I-001 1280 90 I-006 1280 90 I-008 1280 90 I-009 1280 90 I-011 1280 90 I-016 1280 90 I-018 1280 90 I-019 1280 90 I-020 1280 90 I-021 1280 90 I-022 1280 90 I-023 1280 90 I-024 1280 100 I-025 1280 90 I-029 1280 90 I-030 1280 90 I-031 1280 90 I-036 1280 90 I-037 1280 90 I-040 1280 90 I-041 1280 90 Form B11 instance number Dose [g/ha] VERPE I-034 1280 100 I-001 1280 90 I-002 1280 90 I-005 1280 90 I-006 1280 90 I-008 1280 100 I-009 1280 90 I-016 1280 90 I-018 1280 90 I-019 1280 90 I-020 1280 90 I-021 1280 90 I-022 1280 90 I-025 1280 90 I-029 1280 90 I-036 1280 90 I-039 1280 90 I-041 1280 90 Form B12 instance number Dose [g/ha] AMARE I-001 1280 100 I-002 1280 90 I-005 1280 90 I-006 1280 100 I-008 1280 90 I-016 1280 100 I-018 1280 100 I-019 1280 90 I-020 1280 90 I-021 1280 90 I-022 1280 90 I-024 1280 90 I-025 1280 90 I-029 1280 90 I-030 1280 100 I-031 1280 100 I-036 1280 90 I-038 1280 90 I-041 1280 90

As shown by the results, under the application rate of 1280 g active ingredient/ha, various general formula (I) compounds of the present invention have very good post-emergence herbicidal efficacy on a wide range of harmful monocotyledonous and dicotyledonous plants, such weeds Lines (for example) velvetleaf (ABUTH), big ear wheatgrass (ALOMY), retroflexus amaranthus (AMARE), crabgrass (DIGSA), barnyardgrass (ECHCG), Kochia scoparia (KCHSC), rigid ryegrass (LOLRI) , light chamomile (MATIN), bluegrass (POAAN), foxtail (SETVI), chickweed (STEME) and Arabian mother-in-law (VERPE).

C. Pre-emergence herbicidal effect The seeds of the monocotyledonous and dicotyledonous weed plants were sown in sandy loam in plastic pots (double sowing, one monocotyledonous weedy plant and one dicotyledonous weedy plant per pot), and covered with soil. The compound of the invention (formulated as a wettable powder (WP) or emulsifiable concentrate (EC)) is applied to the surface of the covering soil in the form of an aqueous suspension or emulsion at an application rate of 600 liters of water/ha (converted) On, and add 0.5% additives. After treatment, the pots were placed in a greenhouse and kept under optimal growth conditions for the test plants. Visual grading of damage to the test plants compared to the untreated control was carried out after about 3 weeks (herbicidal effect (in %): 100% effect = plant is dead, 0% effect = plant as control).

Tables C1 to C12 below show the effect of selected compounds of the general formula (I) in table 1 on various harmful plants and the corresponding application rates of 320 g/ha (obtained by the experimental procedure mentioned above). Table C1 instance number Dose [g/ha] ABUTH I-001 320 100 I-040 320 100 Table C2 instance number Dose [g/ha] ALOMY I-008 320 90 I-011 320 100 Table C3 instance number Dose [g/ha] DIGSA I-001 320 90 I-005 320 90 I-006 320 100 I-008 320 100 I-009 320 100 I-011 320 100 I-013 320 100 I-018 320 100 I-019 320 100 I-020 320 100 I-021 320 100 I-022 320 100 I-023 320 100 I-024 320 100 I-025 320 100 I-026 320 90 I-036 320 100 I-038 320 100 I-040 320 100 Table C4 instance number Dose [g/ha] ECHCG I-034 320 100 I-001 320 100 I-005 320 100 I-006 320 100 I-008 320 100 I-009 320 90 I-011 320 100 I-013 320 100 I-020 320 100 I-021 320 100 I-022 320 100 I-023 320 100 I-024 320 100 I-036 320 100 I-037 320 90 I-038 320 100 I-040 320 100 Table C5 instance number Dose [g/ha] KCHSC I-034 320 90 I-001 320 90 I-006 320 90 I-008 320 90 I-009 320 90 I-011 320 90 I-013 320 90 I-018 320 90 I-020 320 90 I-021 320 90 I-023 320 90 I-025 320 90 I-036 320 90 I-038 320 90 I-040 320 90 I-041 320 90 Table C6 instance number Dose [g/ha] LOLRI I-034 320 100 I-001 320 100 I-006 320 100 I-008 320 100 I-009 320 100 I-011 320 100 I-013 320 100 I-019 320 90 I-020 320 100 I-021 320 100 I-022 320 100 I-023 320 100 I-024 320 100 I-025 320 90 I-040 320 100 Table C7 instance number Dose [g/ha] MATIN I-034 320 90 I-006 320 90 I-008 320 90 I-011 320 90 I-013 320 90 I-023 320 90 I-024 320 90 I-036 320 90 I-040 320 90 Table C8 instance number Dose [g/ha] POAAN I-034 320 100 I-001 320 100 I-005 320 100 I-006 320 100 I-008 320 100 I-009 320 100 I-011 320 100 I-013 320 100 I-016 320 100 I-018 320 100 I-019 320 100 I-020 320 100 I-021 320 100 I-022 320 100 I-023 320 100 I-024 320 100 I-025 320 100 I-026 320 90 I-033 320 100 I-036 320 100 I-037 320 100 I-038 320 100 I-040 320 100 I-041 320 100 Table C9 instance number Dose [g/ha] SETVI I-034 320 100 I-001 320 100 I-005 320 90 I-006 320 100 I-008 320 100 I-009 320 100 I-011 320 100 I-013 320 100 I-016 320 100 I-018 320 100 I-019 320 100 I-020 320 100 I-021 320 100 I-022 320 100 I-023 320 100 I-024 320 100 I-025 320 100 I-030 320 90 I-031 320 90 I-033 320 100 I-036 320 100 I-037 320 100 I-038 320 90 I-040 320 100 Table C10 instance number Dose [g/ha] STEME I-001 320 90 I-006 320 90 I-008 320 90 I-009 320 90 I-011 320 90 I-013 320 90 I-021 320 90 I-023 320 90 I-024 320 90 I-025 320 90 I-036 320 90 I-040 320 90 Table C11 instance number Dose [g/ha] VERPE I-006 320 90 I-008 320 90 I-009 320 90 I-011 320 90 I-013 320 90 I-025 320 90 I-036 320 90 Table C12 instance number Dose [g/ha] AMARE I-034 320 90 I-001 320 100 I-006 320 90 I-008 320 90 I-009 320 90 I-011 320 90 I-013 320 90 I-023 320 90 I-024 320 90 I-025 320 90 I-031 320 90 I-038 320 90 I-040 320 90 I-041 320 90

As shown in the results, under the application rate of 320 g active ingredient/ha, various general formula (I) compounds of the present invention have very good pre-emergence herbicidal efficacy on a wide range of harmful monocotyledonous and dicotyledonous plants, such weeds Lines (for example) velvetleaf (ABUTH), big ear wheatgrass (ALOMY), retroflexus amaranthus (AMARE), crabgrass (DIGSA), barnyardgrass (ECHCG), Kochia scoparia (KCHSC), rigid ryegrass (LOLRI) , light chamomile (MATIN), bluegrass (POAAN), foxtail (SETVI), chickweed (STEME) and Arabian mother-in-law (VERPE).

D. Post-emergence herbicidal effect Seeds of monocotyledonous and dicotyledonous weed plants were sown in sandy loam in plastic pots (double sowing, one monocotyledonous weed plant and one dicotyledonous weed plant per pot), covered with soil and grown under controlled conditions grow under conditions. 2 to 3 weeks after sowing, the test plants are sprayed at the single leaf stage. The compounds of the invention (formulated as wettable powders (WP) or emulsifiable concentrates (EC)) are sprayed on green plant parts in the form of aqueous suspensions or emulsions at an application rate of 600 liters of water/ha (converted) , and add 0.5% additives. The test plants were placed in a greenhouse and kept under optimal growth conditions for about 3 weeks, and then the formulation effect (herbicidal effect (in %) was assessed visually compared to the untreated control: 100% effect = plant is dead, 0% effect = plant as control).

Tables D1 to D10 below show the effect of selected compounds of general formula (I) in table 1 on various harmful plants and the corresponding application rates of 320 g/ha (obtained by the experimental procedure mentioned above). Table D1 instance number Dose [g/ha] ABUTH I-001 320 100 I-016 320 90 I-018 320 90 Table D2 instance number Dose [g/ha] DIGSA I-006 320 90 I-008 320 90 I-011 320 90 I-019 320 90 I-022 320 90 Table D3 instance number Dose [g/ha] ECHCG I-006 320 90 I-008 320 90 I-011 320 90 I-019 320 90 I-022 320 90 I-036 320 90 Table D4 instance number Dose [g/ha] KCHSC I-001 320 90 I-006 320 90 I-008 320 90 I-009 320 90 I-016 320 90 I-018 320 90 I-019 320 90 I-020 320 90 I-021 320 90 I-023 320 90 I-025 320 90 I-026 320 90 I-029 320 90 I-030 320 90 I-031 320 90 Form D5 instance number Dose [g/ha] LOLRI I-034 320 90 Form D6 instance number Dose [g/ha] POAAN I-006 320 90 I-008 320 90 I-018 320 90 I-019 320 90 I-021 320 90 I-022 320 90 I-024 320 90 I-040 320 90 Form D7 instance number Dose [g/ha] SETVI I-034 320 90 I-006 320 90 I-011 320 90 I-013 320 90 I-036 320 90 Form D8 instance number Dose [g/ha] STEME I-001 320 90 I-006 320 90 I-008 320 90 I-018 320 90 I-020 320 90 I-021 320 90 I-024 320 90 I-026 320 90 I-029 320 90 I-036 320 90 Form D9 instance number Dose [g/ha] VERPE I-034 320 90 I-001 320 90 I-006 320 90 I-008 320 90 I-026 320 90 I-036 320 90 Table D10 instance number Dose [g/ha] AMARE I-001 320 90 I-006 320 90 I-008 320 90 I-016 320 90 I-018 320 90 I-025 320 90 I-026 320 90 I-029 320 90 I-031 320 90 I-036 320 90 As shown by the results, under the application rate of 320 g active ingredient/ha, various general formula (I) compounds of the present invention have very good post-emergence herbicidal efficacy on a wide range of harmful monocotyledonous and dicotyledonous plants, such weeds Lines (for example) velvetleaf (ABUTH), retroflexus amaranthus (AMARE), crabgrass (DIGSA), barnyardgrass (ECHCG), Kochia scoparia (KCHSC), rigid ryegrass (LOLRI), bluegrass (POAAN), foxtail ( SETVI), chickweed (STEME) and Arabian mother-in-law (VERPE).

Claims (8)

A substituted thiazolopyridine of general formula (I) or a salt thereof, ( ¹ ) wherein R represents phenyl, furyl, pyrrolyl, thienyl, pyridyl, pyrimidyl, pyrazinyl, pyrazinyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl, iso Oxazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, cyclopentenyl, cyclohexenyl or oxabicycloheptyl residues, wherein each of the aforementioned 20 residues One is unsubstituted or substituted independently by one or more residues selected from the group R ⁵ , R ² represents hydrogen, halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )- Haloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₂ -C ₄ )-haloalkenyl, (C ₂ -C ₄ )-alkynyl, (C ₂ -C ₄ )-haloalkynyl , (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-Alkylthio, (C ₁ -C ₄ )-Haloalkylthio, (C ₁ -C ₄ )-Alkylsulfinyl, (C ₁ -C ₄ )-Haloalkylsulfinyl group, (C ₁ -C ₄ )-alkylsulfonyl group, (C ₁ -C ₄ )-haloalkylsulfonyl group, (C ₁ -C ₄ )-alkylcarbonyl group, (C ₁ -C ₄ )- Haloalkylcarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )- Halocycloalkyl, (C ₃ -C ₆ )-halocycloalkoxy, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₄ )-alkyl or (C ₁ -C ₄ )-alkyl-(C ₃ -C ₆ )-cycloalkyl, R ³ represents hydrogen, halogen, cyano, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, ( C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )haloalkoxy, (C ₃ -C ₄ )-cycloalkyl or (C ₃ -C ₄ )-halocycloalkyl, R ⁴ Represents hydrogen, halogen, cyano, mercapto, hydroxycarbonyl, (C ₁ -C ₄ )-alkoxy-carbonyl, aminocarbonyl, aminothiocarbonyl, (C ₁ -C ₄ )-alkylamine ylcarbonyl, (C ₂ -C ₈ )-dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl, N -(C ₂ -C ₄ )-alkenyl- N -(C ₁ -C ₄ )-Alkylaminocarbonyl, (C ₁ -C ₄ )-Haloalkyl, (C ₃ -C ₆ )-Cycloalkyl, (C ₃ -C ₆ )-Halocycloalkyl, (C ₁ -C ₄ )-haloalkoxy, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-halocycloalkoxy, (C ₁ -C ₄ )-alkoxy-( C ₁ -C ₄ )-Alkyl, or represents benzyl which is unsubstituted or optionally substituted by one or more residues selected from group R ⁵ , or represents optionally one or more residues selected from cyano , (C ₁ -C ₄ )-Alkylcarbonyl, (C ₁ -C ₄ )-Haloalkyl-carbonyl, Hydroxycarbonyl, (C ₁ -C ₄ )-Alkoxycarbonyl, Aminocarbonyl, (C ₁ - C ₄ )-alkyl-aminocarbonyl, (C ₂ -C ₈ )-dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl and N -(C ₂ -C ₄ )- Alkenyl- N- (C ₁ -C ₄ )-alkylaminocarbonyl substituted (C ₁ -C ₄ )-alkyl, or represents optionally one or more selected from hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₄ )-alkylaminocarbonyl, (C ₂ -C ₈ )-dialkylamino-carbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl and N- (C ₂ -C ₄ )-alkenyl- N- (C ₁ -C ₄ )-alkyl-aminocarbonyl residues substituted (C ₁ -C ₄ ) -alkoxy, or represents optionally one or more selected from hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₄ )-alkylaminocarbonyl, (C ₂ -C ₈ )-dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylamino-carbonyl and N -(C ₂ -C ₄ )-alkenyl- N -(C ₁ -C ₄ )-(C ₁ -C ₄ )-alkylthio substituted by the residue of an alkylaminocarbonyl group, or represented by one or more groups selected from hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, Aminocarbonyl, (C ₁ -C ₄ )-alkylaminocarbonyl, (C ₂ -C ₈ )-dialkylaminocarbonyl, (C ₂ -C ₄ )-alkenylaminocarbonyl and N -( C ₂ -C ₄ )-alkenyl- N- (C ₁ -C ₄ )-alkylaminocarbonyl substituted (C ₁ -C ₄ )-alkylamino, or represented by one or more selected from hydroxycarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, aminocarbonyl, (C ₁ -C ₄ )-alkylaminocarbonyl, (C ₂ -C ₈ )-dialkylaminocarbonyl _{( _} _ _{_ _} _ _{_ _} C ₂ -C ₈ )-dialkylamino, or (C ₁ -C ₄ )-haloalkylthio, (C ₁ -C ₄ )-alkylsulfinyl, (C ₁ -C ₄ )- Haloalkylsulfinyl, (C ₁ -C ₄ )-alkylsulfonyl or (C ₁ -C ₄ )-haloalkylsulfonyl, and R ⁵ represents halogen, nitro, cyano, hydroxyl, amine radical, (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 )-Haloalkylthio, (C ₁ -C ₄ )-Alkylsulfinyl, (C ₁ -C ₄ )-Haloalkylsulfinyl radical, (C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ )-haloalkyl-sulfonyl, (C ₁ -C ₄ )-alkylcarbonyl, (C ₁ -C ₄ ) -haloalkylcarbonyl, (C ₁ -C ₄ )-alkoxycarbonyl, (C ₁ -C ₄ )-haloalkoxycarbonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ ) -halocycloalkyl, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-halocycloalkoxy, (C ₃ -C ₆ )-cycloalkylthio, (C ₃ -C ₆ )-halocyclo-alkylthio, (C ₃ -C ₆ )-cycloalkylsulfinyl, (C ₃ -C ₆ )-halocycloalkylsulfinyl, (C ₃ -C ₆ )-cycloalkylsulfonyl, (C ₃ -C ₆ )-halocycloalkylsulfonyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₄ )- Alkyl, (C ₁ -C ₄ )-alkyl-(C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₄ )-alkoxycarbonyl-(C ₁ -C ₄ )-alkyl, Hydroxycarbonyl-(C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkylamino or (C ₂ -C ₈ )-dialkylamino. Such as claim item 1 general formula (I) compound and/or its salt, wherein ^R represents phenyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, oxa Azolyl, thiadiazolyl, isothiazolyl, cyclopenten-1-yl, cyclohexen-1-yl or 7-oxabicyclo[4.1.0]heptane-1-yl, wherein the aforementioned Each of the 9 residues is unsubstituted or optionally substituted by one or more residues selected from the group R ⁵ , R ² represents hydrogen, halogen, (C ₁ -C ₄ )-alkyl, ( C ₁ -C ₄ )-haloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₂ -C ₄ )-haloalkenyl, (C ₁ -C ₄ )-alkoxy, (C ₁ - C ₄ )haloalkoxy, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )- Halocycloalkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₄ )-alkyl or (C ₁ -C ₄ )-alkyl-(C ₃ -C ₆ )-cycloalkane R ³ is hydrogen, halogen or (C ₁ -C ₄ )-alkyl, R ⁴ represents hydrogen, halogen, cyano, mercapto, (C ₁ -C ₄ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )- Haloalkylthio, (C ₁ -C ₄ )-alkyl-sulfinyl, (C ₁ -C ₄ )-haloalkylsulfinyl, (C ₁ -C ₄ )-alkylsulfinyl or ( C ₁ -C ₄ )-haloalkylsulfonyl, and R ⁵ represents halogen, cyano, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy, (C ₃ -C ₆ )-cycloalkyl or (C ₁ -C ₄ )-alkyl-(C ₃ -C ₆ )-cyclo alkyl. Such as the compound of general formula (I) and/or its salt of claim 1, wherein R ¹ represents phenyl, 2-thienyl, 3-thienyl, oxazolyl or thiadiazolyl, wherein the aforementioned 5 kinds Each of the residues is unsubstituted or optionally substituted by one or more residues selected from the group R ⁵ , R ² represents hydrogen, halogen, (C ₁ -C ₄ )-alkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl or (C ₃ -C ₆ ) -cycloalkyl-(C ₁ -C ₄ )-alkyl, R ³ is hydrogen, R ⁴ represents hydrogen or mercapto, and R ⁵ represents halogen, (C ₁ -C ₄ )-alkyl or (C ₁ -C ₄ )-Alkoxy. Such as claim item 1 general formula (I) compound and/or its salt, wherein ^R represents phenyl, 2-fluorophenyl, 3-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2- Bromo-6-fluorophenyl, 2-ethylphenyl, 2-methoxyphenyl, 2-fluoro-3-methylphenyl, 2,3-dimethylphenyl, 2,4-difluoro Phenyl, 2,5-difluorophenyl, 2,4,5-trifluorophenyl, 3-chloro-2-fluorophenyl, 2-thienyl, 3-fluoro-2-thienyl, 3-bromo -2-thienyl, 3-methyl-2-thienyl, 2-bromo-3-thienyl, 4-methyl-2-thienyl, 3-thienyl, 4-fluoro-3-thienyl, 2 , 4-dimethyl-3-thienyl, 3,5-dimethyl-1,2-oxazol-4-yl or 4-methylthiadiazol-5-yl, R ² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, allyl ^, methoxy ^, ethoxy, methoxymethyl or cyclopropylmethyl, R represents hydrogen, and R represents hydrogen or mercapto. Such as claim item 1 general formula (I) compound and/or its salt, wherein ^R represents phenyl, 2-fluorophenyl, 3-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2- Methoxyphenyl, 2-fluoro-3-methylphenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,4,5-trifluorophenyl, 3-chloro- 2-fluorophenyl, 2-thienyl, 2-bromo-3-thienyl, 3-fluoro-2-thienyl, 3-bromo-2-thienyl, 3-methyl-2-thienyl, 4- Methyl-2-thienyl or 3-thienyl, R ² represents hydrogen, fluorine, bromine, methyl, ethyl, allyl, methoxy, ethoxy or cyclopropylmethyl, R ³ represents hydrogen , and R ⁴ represents hydrogen or mercapto. A use of one or more compounds of general formula (I) and/or salts thereof as claimed in claim 1, which are used as herbicides and/or plant growth regulators. A herbicidal and/or plant growth regulating composition, characterized in that the composition comprises one or more compounds of general formula (I) as claimed in claim 1 and/or salts thereof and one or more compounds selected from group (i) and/or Other substances of (ii): (i) One or more other agrochemical active substances selected from the group consisting of insecticides, acaricides, nematicides, other herbicides, fungicides, safeners, fertilizers and/or other growth regulators , (ii) One or more formulation adjuvants commonly used in crop protection. A method for controlling harmful plants or regulating plant growth, characterized in that an effective amount of One or more compounds of general formula (I) and/or salts thereof as claimed in item 1, or Such as the composition of claim 7, Apply to the plants, plant seeds, soil or cultivated area in or on which the plants grow.