Azole pesticidal compounds

Abstract

The present invention relates to compounds of formula (I) and N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof, wherein the variables are defined according to the description. These compounds of formula (I), the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to methods for controlling invertebrate pests by using these compounds, and to plant propagation material, and to agricultural and veterinary compositions comprising said compounds. # imgabs0 #

Description

[0001] Invertebrate pests (particularly insects, arachnids, and nematodes) destroy growing and harvested crops and infest wooden homes and commercial buildings, causing enormous economic losses to the food supply and property.Therefore, there is a continuing need for new agents to combat invertebrate pests.

[0002] For example, carbamylated and thiocarbamylated oxime derivatives are known for pesticidal use in patent publication WO 2016 / 156076, semicarbazone and thiosemicarbazone derivatives are known for pesticidal use in patent publication WO 2016 / 116445, and pyrazolo-pesticidal compounds are known for pesticidal use in patent publication WO 2021 / 013561.

[0003] Due to the ability of target pests to develop resistance to pesticides, there is a continuing need to identify additional compounds suitable for combating invertebrate pests such as insects, arachnids and nematodes. Furthermore, there is a need for new compounds that have high pesticidal activity and that exhibit a broad spectrum of activity against a large number of different invertebrate pests, especially against difficult-to-control insects, arachnids and nematodes.

[0004] It was therefore an object of the present invention to identify and provide compounds which exhibit high pesticidal activity and have a broad spectrum of activity against invertebrate pests.

[0005] It has been found that these objects can be achieved by substituted bicyclic compounds of formula I as depicted and defined below, including their stereoisomers, their salts (especially their agriculturally or veterinarily acceptable salts), their tautomers and their N-oxides.

[0006] In a first aspect, the present invention relates to compounds of formula I

[0007]

[0008] in

[0009] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-;

[0010] R 5 is H, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkyl-C1-C6-alkoxy, C1-C6-alkyl-C3-C6-cycloalkyl, phenyl, 5- or 6-membered heteroaryl, -CH2-phenyl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or halogen, wherein these alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen or CN;

[0011] A is N or CR A ;

[0012] R A is H, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, halogen, CN or NR 6 R 7 , wherein the alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0013] R 2 is H or C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen, CN or C1-C6-alkoxy;

[0014] B 1 Is N or CR B1 ;

[0015] B 2 Is N or CR B2 ;

[0016] B 3 Is N or CR B3 ;

[0017] B 4 It's CR B4 ;

[0018] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0019] D is part DA or DB,

[0020]

[0021] R 3 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0022] R 4 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN; or

[0023] B is a 5- or 6-membered carbocyclic group, wherein one or two CH2 moieties of the carbocyclic group may be replaced by a carbonyl, O or S, wherein the carbocyclic group is unsubstituted or replaced by R h replace;

[0024] Ar 1 is phenyl or a 5- or 6-membered heteroaryl group, which is unsubstituted or replaced by R Ar1 Replace, where

[0025] R Ar1 is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f 、

[0026] C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、S(=O) m R e , -N=S(=O)-(C1-C6-alkyl)2 or SO2NR b R c replace;

[0027] R 6 and R 7 are identical or different H, C1-C6-alkyl, C3-C6-cycloalkyl, phenyl, -CH2-phenyl, 5- or 6-membered heteroaryl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl, wherein these alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN, C1-C6-alkyl or C1-C6-alkoxy;

[0028] Ar 2 is phenyl or a 5- or 6-membered heteroaryl group, which is unsubstituted or replaced by R Ar2 Replace, where

[0029] R Ar2is halogen, CN, -SCN, -SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyloxy-C1-C4-alkyl, wherein these alkyl, alkoxy, alkenyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or replaced by halogen or CN; C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c replace;

[0030] R a 、R b and R c are identical or different H, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, -C(=O)-C1-C6-alkyl, wherein these alkyl, alkenyl and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0031] R d is H or C1-C6-alkyl;

[0032] R e is C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl, cycloalkyl moieties are unsubstituted or substituted by halogen;

[0033] m is 0, 1, or 2;

[0034] R f is halogen, OH, CN, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyloxy-C1-C4-alkyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted by halogen;

[0035] R h is halogen, C1-C6-alkyl or C1-C6-alkoxy;

[0036] and N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

[0037] In addition, the present invention also relates to processes and intermediates for preparing compounds of formula I and active compound combinations comprising them. In addition, the present invention relates to agricultural or veterinary compositions comprising compounds of formula I, and the use of compounds of formula I or compositions comprising them for combating or controlling invertebrate pests and / or for protecting crops, plants, plant propagation materials and / or growing plants from attack and / or infestation by invertebrate pests. The present invention also relates to methods for applying compounds of formula I. The present invention also relates to methods for protecting crops, plants, plant propagation materials and / or growing plants from attack or infestation by invertebrate pests, the method comprising contacting or treating these crops, plants, plant propagation materials and growing plants or the soil, material, surface, space, area or water in which these crops, plants, plant propagation materials are stored or the plants are grown with an effective amount of pesticidal compounds of at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);

[0038] Furthermore, the present invention relates to seeds comprising a compound of formula I, wherein the compound of formula I includes N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

[0039] Compounds of formula I can be prepared by the procedures as given in the following schemes by appropriate modification of the starting compounds.

[0040] The compounds of formula (I) can be prepared by organic chemistry methods (e.g., by the methods described in Schemes 1 to 24 below in the description of the synthesis of the Examples). Unless otherwise indicated, in Schemes 1 to 24, the group Ar 1 , A, B 1 、B 2 、B 3 、B 4 , D, Q, X, R A 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R h and Ar 2 As defined above for formula (I).

[0041] where D is

[0042] The compounds of formula (I) (where R 4 When it is not H, it is a compound of formula (Ia):

[0043]

[0044]

[0045] In one embodiment of Scheme 1, a compound of formula (Ia-2) is reacted directly with a compound of formula (E1) in the presence of an inorganic base to form a compound of formula (Ia). The isocyanate compound of formula (Ia-2) can be generated in situ from an amine of formula (Ia-1) by using one of the common reagents (such as phosgene, diphosgene, triphosgene, or carbonyldiimidazole) in a mixed solvent system (step 1) and in the presence of a base, as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0046] According to another embodiment of Scheme 1, isocyanate compounds of formula (Ia-2) are generated via Curtis rearrangement of acyl azide (Ia-4) (e.g., by analogy with the method described in WO2014 / 204622). Acid azides of formula (Ia-4) can be prepared from the corresponding carboxylic acid precursors of formula (Ia-3) by treatment with ethyl chloroformate and sodium azide in the presence of an amine base (e.g., triethylamine) or with diphenylphosphoryl azide in the presence of an amine base (e.g., triethylamine).

[0047] Compounds of formula (I) (compounds of formula (Ia) among them) can also be prepared by analogy with the method described in WO 2021 / 011722 or the method described in Scheme 2:

[0048]

[0049] According to the method depicted in Scheme 2, the amine of formula (Ia-1) can be treated with an activating agent (such as 4-nitrophenyl chloroformate) in the presence of a polar aprotic solvent (preferably tetrahydrofuran) to generate an activated carbamate intermediate (Ia-1'), which in turn reacts with a compound of formula (E1) in the presence of an organic base (such as DIPEA) to form a compound of formula (Ia). The compound of formula (E1) can be prepared by analogy with the method described in WO 2021 / 011722.

[0050] Option 3:

[0051]

[0052] As depicted in Scheme 3, compounds of formula (E1) can be treated with an activating agent (such as 4-nitrophenyl chloroformate) in the presence of a polar aprotic solvent (preferably tetrahydrofuran) and an inorganic base (such as cesium carbonate or potassium carbonate) to generate an activated carbamate intermediate (E1-1), which in turn reacts with an amine of formula (Ia-1) in the presence of an inorganic base (such as cesium carbonate or potassium carbonate) to form a compound of formula (Ia).

[0053] The compounds of formula (I) (where R 4 When it is H, it is a compound of formula (Ia'):

[0054]

[0055] As depicted in Scheme 4, compounds of formula (Ia') can be prepared by treating an arylthiourea of ​​formula (E2) with an isocyanate of formula (Ia-2) in an aprotic solvent in the presence of an inorganic base such as cesium carbonate. Compounds of formula (E2) can be prepared by analogy with the method described in WO2021 / 011722.

[0056] Compounds of formula (E1-I), (E1-II), (E1-III) and (E1-IV) can be prepared by analogy with the method described in J. Med. Chem. 2010, 53(10), 4198-4211 or the method described in Scheme 5:

[0057]

[0058] In the above reactions, the compound of formula (E1-Ia) can be converted into various cyclized analogs of formula (E1-I), (E1-II), (E1-III) and (E1-IV). The compounds of formula (E1-I) and (E1-II) can be prepared by treating the compound of formula (E1-Ia) with unsubstituted or mono- or disubstituted 2-chloroacetyl chloride and 3-chloropropionyl chloride in two steps, as described in J. Med. Chem. 2010, 53(10), 4198-4211. The compounds of formula (E1-IIIa) and (E1-IVa) can be prepared by treating the compound of formula (E1-Ia) with unsubstituted or mono- or disubstituted 2-chloroacetaldehyde and 3-chloro-propionaldehyde in two steps, as mentioned in J. Het. Chem. 2006, 43(6), 1523-1531. Compounds of formula (E1-III) and (E1-IV) can be prepared by treating compounds of formula (E1-IIIa) and (E1-IVa) with potassium thiocyanate in an aprotic solvent such as acetone in the presence of an inorganic base such as cesium carbonate.

[0059] Compounds of formula (Ia-I), (Ia-II), (Ia-III) and (Ia-IV) can be prepared from compounds of formula (Ia') by analogy with the method described in WO 2021 / 011722 or the method described in Scheme 6:

[0060]

[0061]

[0062] Compounds of formula (Ia', Scheme 6) can be converted to various cyclized analogs of formula (Ia-I), (Ia-II), (Ia-III) and (Ia-IV). Cyclization can be carried out by treating the compound of formula (Ia') with an α-haloester (such as methyl bromoacetate or methyl bromopropionate) to form an unsubstituted or R-substituted compound. h This is achieved by mono- or di-substituted compounds of formula (Ia-I) and (Ia-II).

[0063] The unsubstituted or R-substituted compounds can be prepared by treating the compound of formula (Ia') with an vicinal dihalide. h Mono- or disubstituted compounds of formula (Ia-III) and (Ia-IV). For steps XVIII and XIX, sodium acetate is preferably used in a protic solvent (such as ethanol) at a temperature in the range of about 20°C to about 70°C. For steps XX and XXI, an inorganic base (such as potassium carbonate) is preferably used in a solvent (such as ACN or 2-butanone) at a temperature between about 0°C and about 80°C. All of the above reactions can be carried out by analogy with the method described in WO 2021 / 011722.

[0064] Compounds of formula (Ia-1) can be prepared by analogy with the method described in Scheme 7:

[0065]

[0066] Where A is N or CR A ;X is Hal

[0067] Where A is CR A ; X is OTf

[0068]

[0069] Compounds of formula (Ia-1) can be prepared using different synthetic routes as depicted in Scheme 7. Step XXII can be carried out starting from an appropriate arylboronic acid precursor (1) via a Suzuki cross-coupling reaction as described in Tetrahedron, 2009, 65(37), 7817-7824 or WO 2018 / 075937.

[0070] Alternatively, the compound of formula (Ia-1) can be prepared by reducing the nitro compound of formula (IIIa-1) using a reducing agent such as SnCl2 in acidic medium, as shown in step XXIII.

[0071] Alternatively, the compound of formula (Ia-1) can also be prepared by reacting the compound of formula (IVa-1) with ammonia in the presence of a metal catalyst or a salt thereof, preferably copper or a salt thereof, as described in Chem. Commun., 2009, 3035-3037.

[0072] Alternatively, the compound of formula (Ia-1) can be prepared from the compound of formula (IVa-1) in two steps. In step XXV, the compound of formula (IVa-1) is treated with tert-butyl carbamate in the presence of a metal catalyst or a salt thereof (preferably palladium or a salt thereof) to form a compound of formula (IVa-2), followed by Boc deprotection using trifluoroacetic acid or dilute hydrochloric acid in step XXVI to form the desired compound. All of these reactions are performed as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0073] Compounds of formula (IIIa-1) can be prepared by analogy with the method described in Scheme 8:

[0074]

[0075] Where A is N or CR A ;X is Hal

[0076] Where A is CR A ; X is OTf

[0077] Step XXVII can be carried out via a Suzuki cross-coupling reaction starting from an arylboronic acid precursor (3), as described in Tetrahedron, 2009, 65(37), 7817-7824 or WO 2018 / 075937.

[0078] Compounds of formula (IVa-1) can be prepared by analogy with the method described in Scheme 9:

[0079]

[0080] Where A is N or CR A ;X is Hal

[0081] Where A is CR A ; X is OTf

[0082] Step XXVIII can be carried out via a Suzuki cross-coupling reaction starting from an arylboronic acid precursor (4), as described in Tetrahedron, 2009, 65(37), 7817-7824 or WO 2018 / 075937.

[0083] Compounds of formula (IVa-1) (where Q is -C(=O)-N(R 5 )-, A is N or CR A And R 5 When it is H, it is a compound of formula (IVa-1-1):

[0084]

[0085] The compound of formula (IVa-1-1) can be prepared from the compound of formula (IVa-1-1a) in six steps. Step XXIX comprises bromination by reacting the compound of formula (IVa-1-1a) with bromine in the presence of a weak base (such as sodium acetate) and a protic solvent (such as ethanol and water). Step XXX comprises alkylation by reacting with a corresponding commercially available alkyl halide, preferably an iodide or bromide, in the presence of a base (such as cesium carbonate) and a polar aprotic solvent (such as DMF), as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March. Step XXXI comprises introducing a protecting group such as 2,4-dimethoxybenzylamine. Step XXXII can be carried out starting from an arylboronic acid precursor (4) via a Suzuki cross-coupling reaction, as described in WO 2018 / 075937. Step XXXIII involves deprotecting the compound of formula (IVa-1-1e) by reacting the compound of formula (IVa-1-1e) with 5N hydrochloric acid. Step XXXIV involves amide formation by reacting the compound of formula (IVa-1-1f) with Ar 1-COOH reacts in the presence of a suitable coupling reagent (such as HATU) and a base (such as DIPEA). All of these steps can be carried out as described in March's Advanced Organic Chemistry [March high organic chemistry] the 6th edition, Michael B.Smith and Jerry March. It is also possible to synthesize a compound of formula (IVa-1-1) by treating a compound of formula (IVa-1-1f) with commercially available benzoyl chloride in the presence of a base, as described in March's Advanced Organic Chemistry [March high organic chemistry] the 6th edition, Michael B.Smith and Jerry March. Alternatively, it is also possible to synthesize a compound of formula (IVa-1-1) by treating a compound of formula (IVa-1-1f) with POCl or SOCl from the corresponding benzoic acid in situ to generate benzoyl chloride, then in the presence of a base, as described in March's Advanced Organic Chemistry [March high organic chemistry] the 6th edition, Michael B.Smith and Jerry March.

[0086] Compounds of formula (IVa-1) (where Q is -C(=O)-N(R 5 )-, A is CR A , R A is H or C1-C6-alkyl or C3-C6-cycloalkyl or CN or C1-C6-alkoxy and R 5 When it is H, it is a compound of formula (IVa-1-1A):

[0087]

[0088] The PCR product can be prepared by reacting with R as described in WO 2018 / 069222. 2 -NHNH2 reaction to prepare compounds of formula (IVa-1-1A) from commercially available benzoyl acetonitrile derivatives (IVa-1-1g). Common intermediates of formula (IVa-1-1A) can be prepared via amide formation by reacting a compound of formula (IVa-1-1h) with Ar 1-COOH reacts in the presence of a suitable coupling reagent (such as HATU) and a base (such as DIPEA). Compounds of formula (IVa-1-1A) can also be synthesized by treating compounds of formula (IVa-1-1h) with commercially available benzoyl chloride in the presence of a base, as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March. Alternatively, compounds of formula (IVa-1-1A) can also be synthesized by in situ generation of benzoyl chloride from the corresponding benzoic acid with POCl or SOCl, followed by treatment with a compound of formula (IVa-1-1h) in the presence of a base, as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0089] Compounds of formula (IVa-1) (where Q is -C(=O)-N(R 5 )-, A is N and R 5 When it is H, it is a compound of formula (IVa-1-1B):

[0090]

[0091] The compound of formula (IVa-1-1B) can be prepared from commercially available benzonitrile (5) in four steps. Step XXXVII can be carried out as described in Green Chemistry, 2013, 15(8), 2252-2260. Step XXXVIII can be carried out as described in US2007 / 0078141. Step XXXIX involves triazole ring formation by heating a benzonitrile having R in a polar protic solvent such as methanol. 2 The compound of formula (IVa-1-1j) of NHNH2 can be prepared by amide formation of the common intermediate of formula (IVa-1-1B) by reacting a compound of formula (IVa-1-1k) with Ar 1-COOH reacts in the presence of a suitable coupling reagent (such as HATU) and a base (such as DIPEA). Compounds of formula (IVa-1-1B) can also be synthesized by treating compounds of formula (IVa-1-1k) with commercially available benzoyl chloride in the presence of a base, as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March. Alternatively, compounds of formula (IVa-1-1B) can also be synthesized by in situ generation of benzoyl chloride from the corresponding benzoic acid with POCl or SOCl, followed by treatment with a compound of formula (IVa-1-1k) in the presence of a base, as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0092] Compounds of formula (IVa-1) (where Q is -N(R)) can be prepared by analogy with the method described in Scheme 13. 5 )-C(=O)-, A is CR A , R A is H or C1-C6-alkyl or C3-C6-cycloalkyl or CN or C1-C6-alkoxy and R 5 When it is H, it is a compound of formula (IVa-1-2):

[0093]

[0094] The compound of formula (IVa-1-2c) can be prepared in two steps from a suitable starting point 2,4-dioxo-4-aryl-butyric acid ethyl ester derivative (IVa-1-2a, commercially available) as described in Chem. Central Journal, 2016, 10(40), 1-6. The compound of formula (IVa-1-2c) can be prepared from the ester intermediate (IVa-1-2b) by hydrolysis with a suitable base (such as LiOH, NaOH) as mentioned in WO 2011 / 050245. Common intermediates of formula (IVa-1-2) can be prepared via amide formation by reacting a compound of formula (IVa-1-2c) with Ar 1 -NH2 reacts in the presence of a suitable coupling reagent (such as HATU) and a base (such as DIPEA).

[0095] Compounds of formula (IVa-1) (where A is CR) can be prepared by analogy with the method described in Scheme 14. A or N, Q is -N(R 4 )-C(=O)- and R5 When it is H, it is a compound of formula (IVa-1-3):

[0096]

[0097] The compound of formula (IVa-1-3) can be prepared from the compound of formula (IVa-1-3a) in six steps. Step XLIV comprises halogenation and step XLV comprises amide formation by reacting the compound of formula (IVa-1-3b) with Ar 1 -NH2 is reacted in the presence of a suitable coupling reagent (such as HATU) and a base (such as DIPEA), and step XLVI comprises a Suzuki cross-coupling of a compound of formula (IIa-4) with a 4-halo-phenylboronic acid derivative. All of these steps can be performed as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0098] Compounds of formula (IVa-1) (where Q is -C(=O)-N(R 5 )-, A is CR A , R A is Cl and R 5 When it is H, it is a compound of formula (IVa-1-4):

[0099]

[0100] Compounds of formula (IVa-1-4) can be prepared from compounds of formula (IVa-1-1h) in two steps. Step XLVII involves chlorination using N-chlorosuccinimide in a polar aprotic solvent such as ACN as described in WO 2014 / 078325. Step XLVIII involves an amide coupling as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0101] Compounds of formula (IVa-1) (where Q is -C(=O)-N(R 5 )-,R A It is NR 6 R 7 And R 5 When it is H, it is a compound of formula (IVa-1-5):

[0102]

[0103] The compound of formula (IVa-1-5) can be prepared from the compound of formula (IVa-1-4) in one step. The amination of the compound of formula (IVa-1-4) (where R 7 or R 6 is C1-C6-alkyl or C3-C6-cycloalkyl, -CH2-phenyl or -CH2-5- or 6-membered heteroaryl or 1,oxolane-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl) can be carried out by reacting with the corresponding commercially available alkylamine or benzylamine in the presence of a base (such as TEA) and a polar aprotic solvent (such as DMF) to obtain the compound of formula (IVa-1-5). The compound of formula (IVa-1-5) (where R 7 or R 6 is phenyl or 5- or 6-membered heteroaryl ring) can be prepared from the compound of formula (IVa-1-4) by a metal-catalyzed reaction with the corresponding aryl halide or 5- or 6-membered heteroaryl halide (preferably iodide or bromide), as described in Chinese J. Chem. [Chinese Chemical Journal] 2012, 30(10), 2356-2362. The compound of formula (IVa-1-5) (where R 7 and R 6 are H) can be prepared from the compound of formula (IVa-1-4) using ammonia in the presence of a metal catalyst or its salt (preferably copper or its salt), as described in Chem. Commun. [Chemical Communications], 2009, 3035-3037.

[0104] The compound of formula (IVa-1) can be prepared by analogy to the method described in Scheme 17 (in the case where Q is -N(R 4 )-C(=O)-, R<00001​​​​​​​​​-NH2 reacts in the presence of a suitable coupling reagent (such as HATU) and a base (such as DIPEA).

[0107] Compounds of formula (IIa) (where Q is -C(=O)-N(R 5 )-, A is CR A , X is Br and R 5 When it is H, it is a compound of formula (IIa-1):

[0108]

[0109] The compound of formula (IIa-1) can be prepared from the compound of formula (IVa-1-1d) in two steps. Step LIII involves deprotecting the compound of formula (IVa-1-1d) by reacting the compound of formula (IVa-1-1d) with 5N hydrochloric acid or TFA in 1,4-dioxane. Step LIV involves amide formation by reacting the compound of formula (IIa-1-1a) with Ar 1 -COOH reacts in the presence of a suitable coupling reagent (such as HATU) and a base (such as DIPEA). It is also possible to synthesize the compound of formula (IIa-1) by treating the compound of formula (IIa-1-1a) with commercially available benzoyl chloride in the presence of a base. Alternatively, it is also possible to synthesize the compound of formula (IIa-1) by treating the compound of formula (IIa-1-1a) with POCl or SOCl from the corresponding benzoic acid in situ to generate benzoyl chloride, then in the presence of a base, with the compound of formula (IIa-1-1a). All of these steps can be carried out as described in March's Advanced Organic Chemistry [March high organic chemistry] 6th edition, Michael B.Smith and Jerry March.

[0110] Alternatively, the compound of formula (IIa-1) can also be prepared in three steps from commercially available substituted ethyl cyanoacetate (6) via the common intermediate (IIa-1-1a). The compound of formula (IIa-1-1a) can be prepared from formula (6) by analogy with the method described in WO 2014 / 78323.

[0111] Compounds of formula (IIa) (where Q is -C(=O)-N(R 5 )-, A is CR A , X is OTf and R 5 When it is H, it is a compound of formula (IIa-2):

[0112]

[0113] Compounds of formula (IIa-2) can be prepared from common intermediates (IIa-1-1b) by analogy with the methods described in WO 2014 / 78323.

[0114] Compounds of formula (IIa) (where Q is -C(=O)-N(R 5 )-, A is N and R 5 When it is H, it is a compound of formula (IIa-3):

[0115]

[0116] The compound of formula (IIa-3) can be prepared from the compound of formula (IVa-1-1d) in two steps. Step LX involves deprotecting the compound of formula (IVa-1-1d) by reacting the compound of formula (IVa-1-1d) with 5N hydrochloric acid or TFA in 1,4-dioxane. Step LXI involves amide formation by reacting the compound of formula (IIa-3-1a) with Ar 1 -COOH reacts in the presence of a suitable coupling reagent (such as HATU) and a base (such as DIPEA). It is also possible to synthesize the compound of formula (IIa-3) by treating the compound of formula (IIa-3-1a) with commercially available benzoyl chloride in the presence of a base. Alternatively, it is also possible to synthesize the compound of formula (IIa-3) by treating the compound of formula (IIa-3-1a) with POCl or SOCl from the corresponding benzoic acid in situ to generate benzoyl chloride, then in the presence of a base, to treat the compound of formula (IIa-3-1a). All of these steps can be carried out as described in March's Advanced Organic Chemistry [March high organic chemistry] 6th edition, Michael B.Smith and Jerry March.

[0117] By analogy with the method described in Scheme 21, the compound of formula (IIa) (where Q is -N(R 5 )-C(=O)-, A is CR A , X is OTf and R 5 When it is H, it is a compound of formula (IIa-5):

[0118]

[0119] The compound of formula (IIa-5) can be prepared in five steps from commercially available substituted diethyl malonate (7). Step LXII can be carried out as described in Org. Lett. [Organic Chemistry Communications], 2014, 16(23), 6120-6123. The compound of formula (IIa-5-1b) can be prepared from formula (IIa-5-1a) by analogy with the method described in US2019 / 0127358. Step LXIV can be carried out as described in WO 2018 / 125961. The last two steps involve hydrolysis with a suitable base (such as LiOH, NaOH) as mentioned in WO 2011 / 050245, followed by reaction of the compound of formula (IIa-5-1d) with Ar 1 -NH2 reacts in the presence of a suitable coupling reagent (such as HATU) and a base (such as DIPEA) to form an amide.

[0120] Compounds of formula (Ia-1) (where Q is -C(=O)-N(R 5 )-,R 5 is C1-C6-alkyl or C3-C6-cycloalkyl or -CH2-phenyl or -CH2-5 or 6-membered heteroaryl or 1,3-dioxolan-2-ylmethyl or phenyl or 5 or 6-membered heteroaryl, it is a compound of formula (Ia-1-1)):

[0121]

[0122] The compound of formula (Ia-1-1a) (wherein R 5 is C1-C6-alkyl or C3-C6-cycloalkyl or -CH2-phenyl or -CH2-5 or 6-membered heteroaryl or 1,3-dioxolan-2-ylmethyl) to prepare compounds of formula (Ia-1-1) analogously to what is described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March. Compounds of formula (Ia-1-1) (wherein R 5is phenyl or a 5- or 6-membered heteroaryl ring), as described in Chinese J. Chem. 2012, 30(10), 2356-2362. Alternatively, the compound of formula (Ia-1-1) can be prepared from the compound of formula (IIIa-1-1a) in two steps. Step LXVIII can be performed similarly to step LXVII and step LXIX involves reduction using a reducing agent such as SnCl2 in ethanol or Fe and NH4Cl in a mixture of ethanol, THF and water.

[0123] Compounds of formula (Ia-1) (where Q is -N(R 5 )-C(=O)-,R 5 is C1-C6-alkyl or C3-C6-cycloalkyl or -CH2-phenyl or -CH2-5 or 6-membered heteroaryl or 1,3-dioxolan-2-ylmethyl or phenyl or 5 or 6-membered heteroaryl, it is a compound of formula (Ia-1-2)):

[0124]

[0125] Compounds of formula (Ia-1-2) can be prepared from compounds of formula (Ia-1-2a) or compounds of formula (IIIa-1-2a) using the reaction conditions disclosed under Scheme 16.

[0126] Compounds of formula (Ia-1) can be prepared by analogy with the method described in Scheme 24 (in B 2 or B 3 When it is Hal, it is a compound of formula (Ia-1-3):

[0127]

[0128] Compounds of formula (Ia-1-3) can be prepared by treating compounds of formula (Ia-1-3a) with an electrophilic halogenating agent such as NXS (X = Cl, Br, I, etc.) in a polar aprotic solvent such as ACN, similar to what is described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0129] Individual compounds of Formula I may also be prepared by derivatization of other compounds of Formula I or intermediates thereof.

[0130] If a mixture of isomers is obtained during synthesis, separation is generally not necessary, since the individual isomers may in some cases be converted into one another during post-processing for use or during application (e.g. under the action of light, acids or bases). Such conversions may also occur after use, for example in the case of plant treatment, in the treated plant or in the harmful fungi to be controlled.

[0131] The skilled person will readily appreciate that the preferences for the substituents given herein in conjunction with compound I, and in particular also the preferences given in the following table for the corresponding substituents, apply correspondingly to the intermediates. The substituents therefore in each case, independently of one another or more preferably in combination, have the meanings as defined herein.

[0132] Unless otherwise indicated, the term "compound according to the invention" or "compound of the present invention" or "compound of formula (I)" refers to

[0133] Compounds of formula I.

[0134] The term "compound according to the invention" or "compound of formula I" includes compounds as defined herein and stereoisomers, salts, tautomers or N-oxides thereof. The term "compound according to the invention" is to be understood as equivalent to the term "compound according to the invention" and therefore also includes stereoisomers, salts, tautomers or N-oxides thereof.

[0135] The term "composition according to the invention" or "composition of the invention" encompasses a composition as defined above comprising at least one compound of formula I according to the invention. The composition of the invention is preferably an agricultural or veterinary composition.

[0136] Depending on the substitution pattern, the compound according to the present invention can have one or more chiral centers, in which case they exist as mixtures of enantiomers or diastereomers. The present invention provides single pure enantiomers or pure diastereomers and mixtures thereof of the compound according to the present invention, as well as the use according to the present invention of the pure enantiomers or pure diastereomers or mixtures thereof of the compound according to the present invention. Suitable compounds according to the present invention also include all possible geometric stereoisomers (cis / trans isomers) and mixtures thereof. Cis / trans isomers can exist with respect to olefins, carbon-nitrogen double bonds or amide groups. The term "stereoisomer" encompasses optical isomers, such as enantiomers or diastereomers (the latter exist due to having more than one chiral center in the molecule), and geometric isomers (cis / trans isomers). The present invention relates to every possible stereoisomer of the compound of Formula I, i.e. single enantiomers or diastereomers, and mixtures thereof.

[0137] The compounds according to the invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or exhibit different biological properties such as activity. The present invention relates to amorphous and crystalline compounds according to the invention, mixtures of different crystalline states of the corresponding compounds according to the invention, and amorphous or crystalline salts thereof.

[0138] The term "tautomer" encompasses isomers derived from compounds of formula I by H atom displacement involving at least one H atom located on a nitrogen, oxygen or sulfur atom. Examples of tautomeric forms are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms, and the like.

[0139] The term "stereoisomer" encompasses optical isomers, such as enantiomers or diastereomers (the latter existing due to more than one chiral center in a molecule), and geometric isomers (cis / trans isomers).

[0140] Depending on the substitution pattern, the compounds of formula I may have one or more chiral centers, in which case they exist as mixtures of enantiomers or diastereomers. The present invention provides the pure enantiomers or diastereomers of compound I and mixtures thereof, as well as the use according to the invention of the pure enantiomers or diastereomers of compound I or mixtures thereof. Suitable compounds of formula I also include all possible geometric stereoisomers (cis / trans isomers) and mixtures thereof.

[0141] The term N-oxide relates to a form of compound I in which at least one nitrogen atom is present in oxidized form (as NO). More precisely, it relates to any compound of the invention having at least one tertiary nitrogen atom oxidized to an N-oxide moiety. The N-oxide of compound I can be obtained by oxidation of, for example, a ring nitrogen atom of an N-heterocycle, such as that present in Ar or R, with a suitable oxidizing agent (such as a peroxycarboxylic acid or other peroxide). 11 The compounds of the present invention can be prepared by using the pyridine or pyrimidine ring in the ring or the imino-nitrogen present in the central tricyclic core. A person skilled in the art knows whether and at which positions the compounds of the present invention can form N-oxides.

[0142] The salts of the compounds of formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a conventional manner, for example, by reacting the compound with an acid of the anion in question, if the compound of formula I has a basic functional group, or by reacting an acidic compound of formula I with a suitable base.

[0143] Suitable agriculturally or veterinarily acceptable salts are especially salts or acid addition salts of those cations of the following acids, the cations and anions of which are known and accepted in the art for forming agriculturally or veterinarily acceptable salts, respectively, and which do not have any adverse effect on the action of the compounds according to the invention. Suitable cations are in particular alkali metal (preferably lithium, sodium and potassium) ions, alkaline earth metal (preferably calcium, magnesium and barium) ions and transition metal (preferably manganese, copper, zinc and iron) ions, and also ammonium (NH 4+ ) and substituted ammonium in which 1 to 4 hydrogen atoms are replaced by C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or -CH2-phenyl. Examples of substituted ammonium ions include methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, in addition to phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium. Suitable veterinarily acceptable acid addition salts (e.g., salts formed from compounds of formula I containing a basic nitrogen atom, such as an amino group) include salts with inorganic acids, such as hydrochlorides, sulfates, phosphates and nitrates, and salts with organic acids, such as acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methanesulfinic acid, methanesulfonic acid and succinic acid.

[0144] Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. These can be formed by reacting compounds of formula I with acids of the corresponding anions, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

[0145] The organic moieties mentioned in the definitions of the variables above, like the term halogen, are collectively referred to as separate lists of individual members. n -C m The possible number of carbon atoms in the group is indicated in each case.

[0146] The term halogen denotes in each case F, Br, Cl or I, in particular F, Cl or Br.

[0147] As used herein and in the alkyl portion of alkoxy, alkylthio, etc., the term "alkyl" refers to a saturated straight-chain or branched hydrocarbon radical having 1 to 2 ("C1-C2-alkyl"), 1 to 3 ("C1-C3-alkyl"), 1 to 4 ("C1-C4-alkyl"), or 1 to 6 ("C1-C6-alkyl") carbon atoms. C1-C2-alkyl is CH3 or C2H5. C1-C3-alkyl is additionally propyl and isopropyl. C1-C4-alkyl is additionally butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), or 1,1-dimethylethyl (tert-butyl). C1-C6-Alkyl is furthermore also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl.

[0148] As used herein, the term "haloalkyl", which is also denoted as "partially or fully halogenated alkyl", refers to straight-chain or branched alkyl groups having 1 to 2 ("C1-C2-haloalkyl"), 1 to 3 ("C1-C3-haloalkyl"), 1 to 4 ("C1-C4-haloalkyl") or 1 to 6 ("C1-C6-haloalkyl") carbon atoms (as mentioned above), wherein some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: In particular, C1-C2-haloalkyl is such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, or pentafluoroethyl. C1-C3-haloalkyl is furthermore, for example, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl, etc. Examples of C1-C4-haloalkyl, in addition to those mentioned for C1-C3-haloalkyl, are 4-chlorobutyl and the like.

[0149] As used herein, the term "alkylene" (or alkanediyl) refers in each case to an alkyl radical as defined above, in which one hydrogen atom at any position of the carbon backbone is replaced by another binding site, thus forming a divalent moiety. Alkylene preferably has 1 to 6 carbon atoms (C1-C6-alkylene), 2 to 6 carbon atoms (C2-C6-alkylene), in particular 1 to 4 carbon atoms (C1-C4-alkylene) or 2 to 4 carbon atoms (C2-C4-alkylene). Examples of alkylene groups are methylene (CH2), 1,1-ethanediyl, 1,2-ethanediyl, 1,3-propylenediyl, 1,2-propylenediyl, 2,2-propylenediyl, 1,4-butanediyl, 1,2-butanediyl, 1,3-butanediyl, 2,3-butanediyl, 2,2-butanediyl, 1,5-pentanediyl, 2,2-dimethylpropylene-1,3-diyl, 1,3-dimethyl-1,3-propylenediyl, 1,6-hexanediyl, and the like.

[0150] As used herein, the term "alkenyl" refers to a monounsaturated straight or branched hydrocarbon radical having 2 to 3 ("C2-C3-alkenyl"), 2 to 4 ("C2-C4-alkenyl"), or 2 to 6 ("C2-C6-alkenyl") carbon atoms and a double bond at any position, for example, C2-C3-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, or 1-methylethenyl; C2-C4-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, or 2-methyl-2-propenyl;C2-C6-alkenyl, such as 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl , 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl, etc.;

[0151] As used herein, the term "alkynyl" refers to a straight or branched hydrocarbon group having 2 to 3 ("C2-C3-alkynyl"), 2 to 4 ("C2-C4-alkynyl"), or 2 to 6 ("C2-C6-alkynyl") carbon atoms and one or two triple bonds at any position, for example, C2-C3-alkynyl, such as ethynyl, 1-propynyl, or 2-propynyl; C2-C4-alkynyl, such as ethynyl, 1-propynyl, or 2-propynyl; propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, etc.; C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, Alkynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, etc.

[0152] As used herein, the term "cycloalkyl" refers to a monocyclic, bicyclic, or polycyclic saturated hydrocarbon radical, particularly having 3 to 6 ("C3-C6-cycloalkyl"), 3 to 5 ("C3-C5-cycloalkyl"), or 3 to 4 ("C3-C4-cycloalkyl") carbon atoms. Examples of monocyclic radicals having 3 to 4 carbon atoms include cyclopropyl and cyclobutyl. Examples of monocyclic radicals having 3 to 5 carbon atoms include cyclopropyl, cyclobutyl, and cyclopentyl. Examples of monocyclic radicals having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of monocyclic radicals having 3 to 8 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atoms include bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.

[0153] As used herein, the term "cycloalkoxy" refers to a cycloalkyl radical as defined above, in particular a monocyclic cycloalkyl radical, in particular having 3 to 6 ("C3-C6-cycloalkoxy"), or 3 to 5 ("C3-C5-cycloalkoxy"), or 3 to 4 ("C3-C4-cycloalkoxy") carbon atoms, which is bound to the remainder of the molecule via an oxygen atom.

[0154] The term "cycloalkyl-C1-C4-alkyl" refers to a C3-C8-cycloalkyl group ("C3-C8-cycloalkyl-C1-C4-alkyl") as defined above, preferably a C3-C6-cycloalkyl group ("C3-C6-cycloalkyl-C1-C4-alkyl"), more preferably a C3-C4-cycloalkyl group ("C3-C4-cycloalkyl-C1-C4-alkyl") (preferably a monocyclic cycloalkyl group), which is bound to the remainder of the molecule via a C1-C4-alkyl group as defined above. Examples of C3-C4-cycloalkyl-C1-C4-alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl and cyclobutylpropyl. Examples of C3-C6-cycloalkyl-C1-C4-alkyl, in addition to those mentioned for C3-C4-cycloalkyl-C1-C4-alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.

[0155] The term "C1-C2-alkoxy" is a C1-C2-alkyl group as defined above attached via an oxygen atom. The term "C1-C3-alkoxy" is a C1-C3-alkyl group as defined above attached via an oxygen atom. The term "C1-C4-alkoxy" is a C1-C4-alkyl group as defined above attached via an oxygen atom. The term "C1-C6-alkoxy" is a C1-C6-alkyl group as defined above attached via an oxygen atom. The term "C1-C 10 -alkoxy" is a C1-C2-alkyl group as defined above attached via an oxygen atom 10-alkyl radical. C1-C2-Alkoxy is OCH3 or OC2H5. C1-C3-Alkoxy is further exemplified by n-propoxy and 1-methylethoxy (isopropoxy). C1-C4-Alkoxy is further exemplified by butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). C1-C6-Alkoxy is furthermore, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy. C1-C8-Alkoxy is furthermore, for example, heptoxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. 10 -Alkoxy is furthermore, for example, nonyloxy, decyloxy and positional isomers thereof.

[0156] The term "C1-C2-haloalkoxy" is a C1-C2-haloalkyl group as defined above attached via an oxygen atom. The term "C1-C3-haloalkoxy" is a C1-C3-haloalkyl group as defined above attached via an oxygen atom. The term "C1-C4-haloalkoxy" is a C1-C4-haloalkyl group as defined above attached via an oxygen atom. The term "C1-C6-haloalkoxy" is a C1-C6-haloalkyl group as defined above attached via an oxygen atom. C1-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5. C1-C3-haloalkoxy is furthermore, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy or 1-(CH2Br)-2-bromoethoxy. C1-C4-haloalkoxy is furthermore, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C1-C6-Haloalkoxy is furthermore, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

[0157] As used herein, the term "C1-C6-alkoxy-C1-C4-alkyl" refers to a straight-chain or branched alkyl group as defined above having 1 to 4 carbon atoms in which one hydrogen atom is replaced by a C1-C6-alkoxy group. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl, 1-isobutoxyethyl, 1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1-methoxypropyl , 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl, 1-isobutoxypropyl, 1-tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl, 2-sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl, 3-tert-butoxypropyl, etc.

[0158] As used herein, the term "alkoxyalkoxy" refers to an alkoxyalkyl radical as defined above, in particular a C1-C6-alkoxy-C1-C4-alkyl radical, which is bound to the remainder of the molecule via an oxygen atom. Examples thereof are OCH2-OCH3, OCH2-OC2H5, n-propoxymethoxy, OCH2-OCH(CH3)2, n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH2-OC(CH3)3, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, and the like.

[0159] The substituent "oxo" replaces CH2 with a C(=O) group.

[0160] The term "aryl" refers to phenyl and bicyclic or polycyclic carbocycles having at least one fused phenylene ring, which are bound to the rest of the molecule. Examples of bicyclic or polycyclic carbocycles having at least one phenylene ring include naphthyl, tetrahydronaphthyl, indanyl, indenyl, anthracenyl, fluorenyl, and the like.

[0161] The term "aryl-C1-C4-alkyl" relates to a C1-C4-alkyl group as defined above in which one of the hydrogen atoms has been replaced by an aryl radical, in particular a phenyl radical. Specific examples of aryl-C1-C4-alkyl groups include -CH2-phenyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenyl-1-propyl and 2-phenyl-2-propyl.

[0162] The term "aryloxy-Ci-C4-alkyl" relates to a C1-C4-alkyl group as defined above in which one hydrogen atom has been replaced by an aryloxy radical, in particular a phenoxy radical. Specific examples of aryloxy-Ci-C4-alkyl groups include phenoxymethyl, 1-phenoxyethyl, 2-phenoxyethyl, 1-phenoxypropyl, 2-phenoxypropyl, 3-phenoxy-1-propyl and 2-phenoxy-2-propyl.

[0163] The term "aryl-C1-C4-carbonyl" relates to an aryl radical as defined above, in particular a phenyl radical, which is bound to the remainder of the molecule via a carbonyl group. Specific examples of arylcarbonyl groups include benzoyl, 1-naphthoyl and 2-naphthoyl.

[0164] The term "heteroaryl" relates to an aromatic heterocyclic radical or heterocycle having 5 or 6 ring atoms (5- or 6-membered heteroaryl) and being monocyclic or having 8, 9 or 10 ring atoms and being bicyclic. A heteroaryl radical will generally have at least one ring atom selected from O, S and N, in the case of N, which may be an imino-nitrogen or amino-nitrogen radical carrying hydrogen or a radical different from hydrogen. A heteroaryl radical may have 1, 2, 3 or 4 further nitrogen atoms as ring members, which further nitrogen atoms are imino-nitrogens. Examples of 5- or 6-membered heteroaryl groups include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-Imidazol-1-yl, 1,3,4-triazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl and 1,3,5-triazin-2-yl. Examples of 8-, 9-, or 10-membered heteroaryl groups include, for example, quinolinyl, isoquinolinyl, cinnolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuranyl, benzothienyl, benzo[b]thiazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, imidazo[1,2-a]pyridin-2-yl, thieno[3,2-b]pyridin-5-yl, imidazo-[2,1-b]-thiazol-6-yl, and 1,2,4-triazolo[1,5-a]pyridin-2-yl. Examples of N-bound 5-, 6-, 7-, or 8-membered saturated heterocyclic groups or heterocycles include: pyrrolidin-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, isoxazolidin-2-yl, thiazolidin-3-yl, isothiazolidin-2-yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-4-yl, azepan-1-yl, and the like.

[0165] The term "heteroaryl-Ci-C4-alkyl" relates to a Ci-C4-alkyl group as defined above in which one of the hydrogen atoms has been replaced by a heteroaryl radical, in particular a pyridyl radical. Specific examples of heteroaryl-Ci-C4-alkyl groups include 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, 1-(2-pyridyl)ethyl, 2-(2-pyridyl)ethyl, 1-(3-pyridyl)ethyl, 2-(3-pyridyl)ethyl, 1-(4-pyridyl)ethyl, 2-(4-pyridyl)ethyl, and the like.

[0166] The term "heteroaryloxy-Ci-C4-alkyl" relates to a C1-C4-alkyl group as defined above in which one hydrogen atom has been replaced by a heteroaryloxy group, in particular a pyridyloxy group. Specific examples of heteroaryloxy-Ci-C4-alkyl include 2-pyridyloxymethyl, 3-pyridyloxymethyl, 4-pyridyloxymethyl, 1-(2-pyridyloxy)ethyl, 2-(2-pyridyloxy)ethyl, 1-(3-pyridyloxy)ethyl, 2-(3-pyridyloxy)ethyl, 1-(4-pyridyloxy)ethyl, 2-(4-pyridyloxy)ethyl, and the like.

[0167] The term "heteroaryl-C1-C4-carbonyl" relates to a heteroaryl group as defined above, in particular a C-bound heteroaryl group, for example 2-, 3- or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 1-, 2- or 3-pyrrolyl, 2- or 4-pyrimidinyl, pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl, which is bound to the remainder of the molecule via a carbonyl group.

[0168] If not otherwise stated, the term "substituted" means substituted by 1, 2 or up to the maximum possible number of substituents. If not otherwise stated, if there are more than one substituents as defined in the compounds of formula I, they are independent of each other and may be the same or different.

[0169] With respect to the variables, examples of compounds of formula I are,

[0170] In a preferred embodiment, B 1 、B 2 and B 3 At most two of them can be N;

[0171] In another embodiment, B 1 It's CR B1 , B 2 It's CR B2 , and B 3 It's CR B3 ;

[0172] In another embodiment, B 1 It's N, B 2 It's CR B2 , and B 3 It's CR B3 ;

[0173] In another embodiment, B 1 It's CR B1 , B 2 is N, and B 3 It's CR B3 ;

[0174] In another embodiment, B1 It's CR B1 , B 2 is N, and B 3 It is N;

[0175] In another embodiment, B 1 It's N, B 2 is N, and B 3 It's CR B3 ;

[0176] In another embodiment, B 1 It's CR B1 , and B 2 Is N or CR B2 , B 3 Is N or CR B3 ;

[0177] In another embodiment, B 3 It's CR B3 , and B 1 Is N or CR B2 , B 2 Is N or CR B3 ;

[0178] In one embodiment, A is N;

[0179] In another embodiment, A is CR A .

[0180] In one embodiment, R A is H, halogen, CN, C1-C6-alkyl, C1-C6-alkoxy or C3-C6-cycloalkyl, wherein these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0181] In another embodiment, R A is H, halogen, CN, C1-C6-alkyl or C3-C6-cycloalkyl;

[0182] In another embodiment, R A is H, CN or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen or CN;

[0183] In another embodiment, R A is H, CN or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen or CN;

[0184] In another embodiment, R A is CN or C1-C6-alkyl, which is unsubstituted or substituted by halogen or CN;

[0185] In another embodiment, R A It is CN;

[0186] In another embodiment, R A is C1-C6-alkyl, which is unsubstituted;

[0187] In another embodiment, R A is C1-C6-alkyl, which is substituted by halogen or CN;

[0188] In another embodiment, R A is C3-C6-cycloalkyl, which is unsubstituted or substituted by halogen or CN;

[0189] In another embodiment, R A is a C3-C6-cycloalkyl group, which is unsubstituted;

[0190] In another embodiment, R A is C3-C6-cycloalkyl, which is substituted by halogen or CN;

[0191] In another embodiment, R A is H or halogen;

[0192] In another embodiment, R A It is H;

[0193] In another embodiment, R A It is a halogen;

[0194] In another embodiment, R A is H, CH3 or CN;

[0195] In another embodiment, R A is CH3 or CN;

[0196] In another embodiment, R A It is NR 6 R 7 ;

[0197] In another embodiment, A is N, C(C1-C6-alkyl), or C(CN);

[0198] In another embodiment, A is N, C(CH3) or C(CN);

[0199] In one embodiment, R 6 and R 7are identical or different H, C1-C6-alkyl, phenyl, -CH2-phenyl, 5- or 6-membered heteroaryl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl, wherein these alkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN or C1-C6-alkyl.

[0200] In one embodiment, R 6 and R 7 are the same or different H, phenyl, -CH2-phenyl, 5- or 6-membered heteroaryl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl, wherein these phenyl and heteroaryl moieties are unsubstituted or substituted by halogen or CN,

[0201] In another embodiment, R 6 and R 7 are identical or different H, phenyl, -CH2-phenyl, 5- or 6-membered heteroaryl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl, wherein these phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN or C1-C6-alkyl;

[0202] In another embodiment, R 6 and R 7 are identical or different H, -CH2-5 or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl, wherein these phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN or C1-C6-alkyl;

[0203] In another embodiment, R 6 is H, and R 7 is -CH2-5 or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl, wherein these alkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN or C1-C6-alkyl;

[0204] In another embodiment, R 6 and R 7 are independently selected from Rx-1 to Rx-7 as shown in Table Rx.

[0205] Table Rx:

[0206]

[0207] In another embodiment, R 6 and R 7are independently selected from Rx-1, Rx-2, Rx-7 and Rx-8. 2 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0208] In one embodiment, R 2 is H, C1-C6-alkyl or C3-C6-cycloalkyl;

[0209] In another embodiment, R 2 is H or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen or CN;

[0210] In another embodiment, R 2 is H or C3-C6-cycloalkyl, wherein these cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0211] In another embodiment, R 2 is C1-C6-alkyl, which is unsubstituted or substituted by halogen or CN;

[0212] In another embodiment, R 2 is C1-C6-alkyl, which is unsubstituted;

[0213] In another embodiment, R 2 is C1-C6-alkyl, which is substituted by halogen or CN;

[0214] In another embodiment, R 2 is C3-C6-cycloalkyl, which is unsubstituted or substituted by halogen or CN;

[0215] In another embodiment, R 2 is a C3-C6-cycloalkyl group, which is unsubstituted;

[0216] In another embodiment, R 2 is C3-C6-cycloalkyl, which is substituted by halogen or CN;

[0217] In another embodiment, R 2 It is H, CH3, C2H5, n-C3H7, isopropyl, cyclopropyl, CH2F, CHF2 or CF3.

[0218] In another embodiment, R 2 is H, CH3, C2H5, isopropyl or cyclopropyl;

[0219] In another embodiment, R 2 is H or CH3;

[0220] In another embodiment, R 2 It is H;

[0221] In another embodiment, R 2 It is CH3;

[0222] In another embodiment, R 2 It is C2H5;

[0223] In another embodiment, R 2 is isopropyl;

[0224] In another embodiment, R 2 It is cyclopropyl;

[0225] In one embodiment, R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0226] In another embodiment, R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl or C1-C6-alkoxy, where these alkyl and alkoxy moieties are unsubstituted or substituted by halogen;

[0227] In another embodiment, R B1 、R B2 、R B3 and R B4 are independently H, halogen or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen;

[0228] In another embodiment, R B1 、R B2 、R B3 and R B4 are independently H, Cl, Br, F, CN, CH3, C2H5, n-C3H7, isopropyl, cyclopropyl, CF3, CH2F, OCH3 or OCHF2;

[0229] In another embodiment, R B1 、R B2 、R B3 and R B4 are independently H, Cl, Br, F, CN, CH3, isopropyl, OCH3 or OCHF2;

[0230] In another embodiment, R B1 、R B2 、R B3 and R B4 are independently H, Cl, F, CN, CH3 or OCH3;

[0231] In another embodiment, R B1 and R B4 are independently H, Cl or CH3;

[0232] In another embodiment, R B2 and R B3 are independently H, Cl, Br, F, CN, CH3, isopropyl, cyclopropyl, OCH3 or OCHF2;

[0233] In another embodiment, R B2 and R B3 are independently H, Cl, F, Br, CN, CH3 or OCH3;

[0234] In one embodiment, Q is -C(=O)-N(R 5 )-.

[0235] In another embodiment, Q is -N(R 5 )-C(=O)-.

[0236] In one embodiment, R 5 is H, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkyl-C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0237] In another embodiment, R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0238] In another embodiment, R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted;

[0239] In another embodiment, R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are substituted by halogen or CN;

[0240] In another embodiment, R 5 is H, CH3, C2H5 or -CH2-CN;

[0241] In another embodiment, R 5 is H, CH3 or C2H5;

[0242] In another embodiment, R 5 is H or CH3;

[0243] In one embodiment, D is DA;

[0244] In one embodiment, R 3 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0245] In another embodiment, R 3 is H or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen or CN;

[0246] In another embodiment, R 3 is H or C3-C6-cycloalkyl, wherein these cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0247] In another embodiment, R 3 It is H;

[0248] In another embodiment, R 3 is H, and DA exists in either of the following tautomeric forms D3 and D4;

[0249]

[0250] In one embodiment, R 4 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkyl, -O-(C=O)-C1-C6-alkoxy or CN;

[0251] In another embodiment, R 4 is H or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkyl, -O-(C=O)-C1-C6-alkoxy or CN;

[0252] In another embodiment, R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0253] In another embodiment, R 4is H or C3-C6-cycloalkyl, wherein these cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0254] In another embodiment, R 4 is H or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted;

[0255] In another embodiment, R 4 It is H;

[0256] In another embodiment, R 4 is H, and DA exists in either of the following tautomeric forms D1 and D2;

[0257]

[0258] In another embodiment, D is DB, wherein B is a 5- or 6-membered carbocyclic group, wherein one or two CH2 moieties of the carbocyclic group may be replaced by a carbonyl group, wherein the carbocyclic group is unsubstituted or replaced by R h replace;

[0259] In another embodiment, D is DB, wherein B is a 5- or 6-membered carbocyclic group, wherein one CH2 portion of the carbocyclic group may be replaced by a carbonyl group, wherein the carbocyclic group is unsubstituted or replaced by R h replace;

[0260] In another embodiment, D is DB, wherein B is a 5- or 6-membered carbocyclic group, wherein one CH2 portion of the carbocyclic group may be replaced by a carbonyl group;

[0261] In another embodiment, D is DB, wherein B is a 5- or 6-membered carbocyclic group, wherein one CH2 portion of the carbocyclic group is replaced by a carbonyl group;

[0262] In another embodiment, D is DB selected from D5 to D7, and wherein the carbocyclic group of D5 to D7 is unsubstituted or substituted with 1 or 2 substituents R h replace,

[0263]

[0264] In another embodiment, D is a group selected from the group consisting of D5 to D7 moieties, which are unsubstituted or substituted with 1 or 2 substituents R h replace,

[0265]

[0266] In another embodiment, D is DB selected from D5 to D7, and wherein the carbocyclic group of the D5 to D7 moieties is unsubstituted;

[0267] In another embodiment, D is DB selected from D5 to D7, and wherein the carbocyclic group of D5 to D7 is replaced by 1 or 2 substituents R h replace;

[0268] In another embodiment, D is selected from DA, D5, D6 and D7 as defined herein;

[0269] In another embodiment, D is selected from DA, D5, D6 and D7, wherein the carbocyclic groups of D5, D6 and D7 are unsubstituted or substituted with 1 or 2 substituents R h replace;

[0270] In another embodiment, D is DA or D5, wherein D5 is unsubstituted or substituted with 1 substituent R h replace;

[0271] In another embodiment, D is selected from DA or D5, wherein the carbocyclic group of D5 is replaced by one substituent R h replace;

[0272] In another embodiment, D is selected from DA or D5, wherein the carbocyclic group of D5 is unsubstituted;

[0273] In another embodiment, D is D5, wherein the carbocyclic group of D5 is unsubstituted or substituted with one substituent R h replace;

[0274] In one embodiment, Ar 1 is phenyl, which is unsubstituted or replaced by R Ar1 replace.

[0275] In another embodiment, Ar 1 is a 5- or 6-membered heteroaryl group which is unsubstituted or replaced by R Ar1 replace.

[0276] In further embodiments, Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridyl, preferably phenyl, which is unsubstituted or replaced by R Ar1 replace.

[0277] In one embodiment, R Ar1 is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f 、C(=O)-OR a NRb R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、-N=S(=O)-(C1-C6-alkyl)2、SO2NR b R c or S(=O) m R e replace;

[0278] In another embodiment, R Ar1 is halogen, SF5, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f 、

[0279] NR b R c 、C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e , -N=S(=O)-(C1-C6-alkyl)2 or S(=O) m R e replace;

[0280] In another embodiment, R Ar1 is halogen, SF5, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl and alkynyl moieties are unsubstituted or replaced by R f 、

[0281] or S(=O) m R e replace;

[0282] In another embodiment, R Ar1 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, wherein these alkyl and alkoxy moieties are unsubstituted or replaced by R f replace,

[0283] In another embodiment of the compound of Formula I, wherein

[0284] Ar 1is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridyl, preferably phenyl, which is unsubstituted or replaced by R Ar1 replace;

[0285] R Ar1 is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f 、C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、-N=S(=O)-(C1-C6-alkyl)2、SO2NR b R c or S(=O) m R e replace;

[0286] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0287] R d is H or C1-C6-alkyl;

[0288] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0289] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0290] m is 0, 1, or 2.

[0291] In another embodiment of the compound of Formula I, wherein

[0292] Ar 1 is phenyl, which is unsubstituted or replaced by R Ar1 replace;

[0293] RAr1 is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f 、C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、-N=S(=O)-(C1-C6-alkyl)2、SO2NR b R c or S(=O) m R e replace;

[0294] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0295] R d is H or C1-C6-alkyl;

[0296] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0297] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0298] m is 0, 1, or 2.

[0299] In another embodiment of the compound of Formula I, wherein

[0300] Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridyl, preferably phenyl, which is unsubstituted or replaced by R Ar1 replace;

[0301] R Ar1is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and C3-C6-heterocyclyl moieties are unsubstituted or replaced by R f 、

[0302] NR b R c 、C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e , -N=S(=O)-(C1-C6-alkyl)2 or S(=O) m R e replace;

[0303] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0304] R d is H or C1-C6-alkyl;

[0305] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0306] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0307] m is 0, 1, or 2.

[0308] In another embodiment, Ar 1 Selected from Table Ar 1 Ar 1 -1 to Ar 1 -30,

[0309] Table Ar 1 :

[0310]

[0311]

[0312] In another embodiment, Ar 1 Selected from Ar 1 -1 to Ar1 -14;

[0313] In another embodiment, Ar 1 Selected from Ar 1 -1 to Ar 1 -5;

[0314] In one embodiment, Ar 2 is phenyl, which is unsubstituted or replaced by R Ar2 replace;

[0315] In another embodiment, Ar 2 is a 5- or 6-membered heteroaryl group which is unsubstituted or replaced by R Ar2 replace;

[0316] In another embodiment, Ar 2 is phenyl, pyrimidinyl, thienyl, thiazolyl or pyridinyl, which is unsubstituted or replaced by R Ar2 replace.

[0317] In one embodiment, R Ar2 is halogen, CN, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyloxy-C1-C4-alkyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or replaced by halogen,

[0318] C(=O)-OR a NR b R c or C1-C6-alkylene-CN substitution;

[0319] In another embodiment, R Ar2 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, wherein these alkyl, alkoxy and cycloalkyl parts are unsubstituted or replaced by halogen,

[0320] or

[0321] NR b R c replace;

[0322] In another embodiment, R Ar2 is halogen, CN, C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen;

[0323] In another embodiment, R Ar2 is halogen or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen;

[0324] In another embodiment, R Ar2 is halogen or C1-C6-alkyl;

[0325] In another embodiment, R Ar2 It is a halogen;

[0326] In another embodiment, R Ar2 is C1-C6-alkyl;

[0327] In another embodiment, R Ar2 is halogen or CN.

[0328] In another embodiment, Ar 2 Selected from Ar shown in Table Ar2 2 -1 to Ar 2 -20,

[0329] Table Ar 2 :

[0330]

[0331] In another embodiment, Ar 2 Selected from Ar 2 -1 to Ar 2 -20;

[0332] In another embodiment, Ar 2 Selected from Ar 2 -1 to Ar 2 -6;

[0333] In one embodiment, R a 、R b and R c are identical or different H, C1-C6-alkyl, C2-C6-alkenyl, which are unsubstituted or substituted by halogen;

[0334] In another embodiment, R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0335] In one embodiment, R d It is H;

[0336] In another embodiment, R d It is C1-C6-alkyl.

[0337] In one embodiment, R e is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl;

[0338] In another embodiment, R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0339] In one embodiment, R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0340] In another embodiment, R f is halogen, OH, CN or C1-C6-alkyl.

[0341] In one embodiment, R h is halogen or C1-C6-alkyl;

[0342] In one embodiment, m is 0;

[0343] In another embodiment, m is 1;

[0344] In another embodiment, m is 2;

[0345] In another embodiment, m is 0 or 1;

[0346] In another embodiment, m is 1 or 2.

[0347] In another embodiment of the compound of Formula I, wherein

[0348] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-;

[0349] D is DA, D5, D6 or D7, preferably D5;

[0350] B 1 Is N or CR B1 , B 2 It's CR B2 , and B 3 It's CR B3 ;

[0351] R B1 、R B2 、R B3 and R B4are independently of one another H, halogen, CN, C1-C6-alkyl or C1-C6-alkoxy, where these alkyl and alkoxy moieties are unsubstituted or substituted by halogen;

[0352] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl;

[0353] R A is H, halogen, CN, C1-C6-alkyl or C3-C6-cycloalkyl;

[0354] R 2 is H or C1-C6-alkyl;

[0355] R 3 is H or C1-C6-alkyl;

[0356] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0357] Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridyl, preferably phenyl, which is unsubstituted or replaced by R Ar1 replace;

[0358] R Ar1 is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f 、C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、-N=S(=O)-(C1-C6-alkyl)2、SO2NR b R c or S(=O) m R e replace;

[0359] R a 、R b and R care identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0360] R d is H or C1-C6-alkyl;

[0361] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0362] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0363] m is 0, 1, or 2.

[0364] In another embodiment of the compound of Formula I, wherein

[0365] Q is -C(=O)-N(R 5 )-;

[0366] D is DB, preferably D5;

[0367] B 1 Is N or CR B1 , B 2 It's CR B2 , and B 3 It's CR B3 ;

[0368] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0369] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl;

[0370] R A is H, halogen, CN, C1-C6-alkyl or C3-C6-cycloalkyl;

[0371] R 2 is C1-C6-alkyl;

[0372] Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridyl, preferably phenyl, which is unsubstituted or replaced by R Ar1 replace;

[0373] R Ar1 is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and C3-C6-heterocyclyl moieties are unsubstituted or replaced by R f 、

[0374] NR b R c 、C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e , -N=S(=O)-(C1-C6-alkyl)2 or S(=O) m R e replace;

[0375] Ar 2 is phenyl, which is unsubstituted or replaced by R Ar2 replace;

[0376] R Ar2 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, wherein these alkyl, alkoxy and cycloalkyl parts are unsubstituted or replaced by halogen,

[0377] NR b R c replace;

[0378] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0379] R d is H or C1-C6-alkyl;

[0380] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0381] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0382] m is 0, 1, or 2.

[0383] In another embodiment, the compound of formula I is selected from the compounds of formulae A.1 to A.20;

[0384]

[0385]

[0386] In another embodiment, the compound of formula I is selected from the compounds of formulae A.1 to A.5;

[0387] In another embodiment, the compound of formula I is selected from the compounds of formula A.6 to A.10;

[0388] In another embodiment, the compound of formula I is selected from compounds of formula A.11 to A.15;

[0389] In another embodiment, the compound of formula I is selected from the compounds of formula A.16 to A.20;

[0390] In another embodiment, the compound of formula I is selected from the compounds of formula A.1 and A.6;

[0391] In another embodiment, the compound of formula I is selected from compounds of formula A.11 and A.16;

[0392] In another embodiment, the compound of formula I is selected from compounds of formula A.12 and A.17;

[0393] In another embodiment, the compound of formula I is selected from the compounds of formula A.15 and A.20;

[0394] In another embodiment, the compound of formula I is selected from the group consisting of compounds of formula A.1, A.6, A.16, A.17, and A.20; In another embodiment, the compound of formula I is selected from the group consisting of compounds of formula A.1, A.6, A.16, and A.20;

[0395] In another embodiment, the compound of formula I is selected from the compounds of formula A.1, A.6, A.11 and A.16;

[0396] In another embodiment, the compound of formula I is selected from the compounds of formula A.2, A.7, A.12 and A.17;

[0397] In another embodiment, the compound of formula I is selected from the compounds of formula A.3, A.8, A.13 and A.18;

[0398] In another embodiment, the compound of formula I is selected from the compounds of formula A.4, A.9, A.14 and A.19;

[0399] In another embodiment, the compound of formula I is selected from the compounds of formula A.5, A.10, A.15 and A.20;

[0400] In another embodiment, the compound of Formula I is A.1;

[0401] In another embodiment, the compound of Formula I is A.2;

[0402] In another embodiment, the compound of Formula I is A.3;

[0403] In another embodiment, the compound of formula I is A.4;

[0404] In another embodiment, the compound of formula I is A.5;

[0405] In another embodiment, the compound of formula I is A.6;

[0406] In another embodiment, the compound of Formula I is A.7;

[0407] In another embodiment, the compound of formula I is A.8;

[0408] In another embodiment, the compound of formula I is A.9;

[0409] In another embodiment, the compound of formula I is A.10;

[0410] In another embodiment, the compound of Formula I is A.11;

[0411] In another embodiment, the compound of formula I is A.12;

[0412] In another embodiment, the compound of formula I is A.13;

[0413] In another embodiment, the compound of formula I is A.14;

[0414] In another embodiment, the compound of formula I is A.15;

[0415] In another embodiment, the compound of formula I is A.16;

[0416] In another embodiment, the compound of formula I is A.17;

[0417] In another embodiment, the compound of formula I is A.18;

[0418] In another embodiment, the compound of formula I is A.19;

[0419] In another embodiment, the compound of formula I is A.20;

[0420] In another embodiment, the compound of formula I is selected from the compounds of formula A.1, A.6, A.11 and A.16, wherein

[0421] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0422] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0423] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0424] R 2 is H or C1-C6-alkyl, preferably CH3;

[0425] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0426] R 3 is H or C1-C6-alkyl;

[0427] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0428] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0429] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0430] In another embodiment, the compound of formula I is selected from the compounds of formula A.1 to A.5, wherein

[0431] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0432] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0433] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0434] R 2 is H or C1-C6-alkyl, preferably CH3;

[0435] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0436] R 3 is H or C1-C6-alkyl;

[0437] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0438] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0439] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0440] In another embodiment, the compound of formula I is selected from the compounds of formula A.6 to A.10, wherein

[0441] Q is -C(=O)-N(R 5 )-or-N(R 5)-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0442] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0443] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0444] R 2 is H or C1-C6-alkyl, preferably CH3;

[0445] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0446] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0447] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0448] In another embodiment, the compound of formula I is selected from the compounds of formula A.11 to A.15, wherein

[0449] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0450] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0451] R 2 is H or C1-C6-alkyl, preferably CH3;

[0452] RB1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0453] R 3 is H or C1-C6-alkyl;

[0454] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0455] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0456] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0457] In another embodiment, the compound of formula I is selected from the compounds of formula A.16 to A.20, wherein

[0458] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0459] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0460] R 2 is H or C1-C6-alkyl, preferably CH3;

[0461] R B1 、R B2 、R B3 and R B4are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0462] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0463] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0464] In another embodiment, the compound of formula I is selected from the compounds of formula A.1 and A.6, wherein

[0465] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0466] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0467] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0468] R 2 is H or C1-C6-alkyl, preferably CH3;

[0469] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0470] R 3 is H or C1-C6-alkyl;

[0471] R 4is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0472] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0473] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0474] In another embodiment, the compound of formula I is selected from the compounds of formula A.2 and A.7, wherein

[0475] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0476] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0477] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0478] R 2 is H or C1-C6-alkyl, preferably CH3;

[0479] R B1 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0480] R 3 is H or C1-C6-alkyl;

[0481] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0482] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0483] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0484] In another embodiment, the compound of formula I is selected from the compounds of formula A.3 and A.8, wherein

[0485] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0486] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0487] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0488] R 2 is H or C1-C6-alkyl, preferably CH3;

[0489] R B1 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0490] R 3 is H or C1-C6-alkyl;

[0491] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0492] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar1 -5;

[0493] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0494] In another embodiment, the compound of formula I is selected from the compounds of formula A.4 and A.9, wherein

[0495] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0496] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0497] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0498] R 2 is H or C1-C6-alkyl, preferably CH3;

[0499] R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0500] R 3 is H or C1-C6-alkyl;

[0501] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0502] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0503] Ar 2 Selected from Ar 2 -1 to Ar 2-20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0504] In another embodiment, the compound of formula I is selected from the compounds of formula A.5 and A.10, wherein

[0505] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0506] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0507] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0508] R 2 is H or C1-C6-alkyl, preferably CH3;

[0509] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0510] R 3 is H or C1-C6-alkyl;

[0511] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0512] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0513] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0514] In another embodiment, the compound of formula I is selected from A.1, wherein

[0515] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0516] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0517] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0518] R 2 is H or C1-C6-alkyl, preferably CH3;

[0519] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0520] R 3 is H or C1-C6-alkyl;

[0521] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0522] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0523] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0524] In another embodiment, the compound of Formula I is A.2, wherein

[0525] Q is -C(=O)-N(R5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0526] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0527] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0528] R 2 is H or C1-C6-alkyl, preferably CH3;

[0529] R B1 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0530] R 3 is H or C1-C6-alkyl;

[0531] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0532] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0533] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0534] In another embodiment, the compound of Formula I is A.3, wherein

[0535] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0536] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0537] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0538] R 2 is H or C1-C6-alkyl, preferably CH3;

[0539] R B1 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0540] R 3 is H or C1-C6-alkyl;

[0541] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0542] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0543] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0544] In another embodiment, the compound of Formula I is A.4, wherein

[0545] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0546] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0547] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0548] R 2 is H or C1-C6-alkyl, preferably CH3;

[0549] R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0550] R 3 is H or C1-C6-alkyl;

[0551] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0552] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0553] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0554] In another embodiment, the compound of Formula I is A.5, wherein

[0555] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0556] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0557] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0558] R 2 is H or C1-C6-alkyl, preferably CH3;

[0559] R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0560] R 3 is H or C1-C6-alkyl;

[0561] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0562] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0563] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0564] In another embodiment, the compound of Formula I is A.6, wherein

[0565] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0566] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0567] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0568] R 2 is H or C1-C6-alkyl, preferably CH3;

[0569] R B1 、R B2 、R B3 and R B4are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0570] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0571] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0572] In another embodiment, the compound of Formula I is A.7, wherein

[0573] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0574] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0575] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0576] R 2 is H or C1-C6-alkyl, preferably CH3;

[0577] R B1 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0578] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0579] Ar 2 Selected from Ar2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0580] In another embodiment, the compound of Formula I is A.8, wherein

[0581] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0582] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0583] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0584] R 2 is H or C1-C6-alkyl, preferably CH3;

[0585] R B1 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0586] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0587] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0588] In another embodiment, the compound of Formula I is A.9, wherein

[0589] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0590] R5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0591] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0592] R 2 is H or C1-C6-alkyl, preferably CH3;

[0593] R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0594] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0595] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0596] In another embodiment, the compound of Formula I is A.10, wherein

[0597] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0598] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0599] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0600] R 2 is H or C1-C6-alkyl, preferably CH3;

[0601] R B2 、R B3 and R B4are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0602] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0603] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0604] In another embodiment, the compound of Formula I is A.11, wherein

[0605] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0606] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0607] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0608] R 2 is H or C1-C6-alkyl, preferably CH3;

[0609] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0610] R 3 is H or C1-C6-alkyl;

[0611] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0612] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0613] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0614] In another embodiment, the compound of Formula I is A.12, wherein

[0615] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0616] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0617] R 2 is H or C1-C6-alkyl, preferably CH3;

[0618] R B1 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0619] R 3 is H or C1-C6-alkyl;

[0620] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0621] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0622] Ar2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0623] In another embodiment, the compound of Formula I is A.13, wherein

[0624] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0625] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0626] R 2 is H or C1-C6-alkyl, preferably CH3;

[0627] R B1 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0628] R 3 is H or C1-C6-alkyl;

[0629] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0630] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0631] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0632] In another embodiment, the compound of Formula I is A.14, wherein

[0633] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0634] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0635] R 2 is H or C1-C6-alkyl, preferably CH3;

[0636] R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0637] R 3 is H or C1-C6-alkyl;

[0638] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0639] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0640] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0641] In another embodiment, the compound of Formula I is A.15, wherein

[0642] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0643] R 5is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0644] R 2 is H or C1-C6-alkyl, preferably CH3;

[0645] R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0646] R 3 is H or C1-C6-alkyl;

[0647] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN;

[0648] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0649] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0650] In another embodiment, the compound of Formula I is A.16, wherein

[0651] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0652] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0653] R 2 is H or C1-C6-alkyl, preferably CH3;

[0654] R B1、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0655] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0656] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0657] In another embodiment, the compound of Formula I is A.17, wherein

[0658] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0659] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0660] R 2 is H or C1-C6-alkyl, preferably CH3;

[0661] R B1 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0662] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0663] Ar 2 Selected from Ar 2 -1 to Ar2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0664] In another embodiment, the compound of Formula I is A.18, wherein

[0665] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0666] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0667] R 2 is H or C1-C6-alkyl, preferably CH3;

[0668] R B1 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0669] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0670] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0671] In another embodiment, the compound of Formula I is A.19, wherein

[0672] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0673] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0674] R 2 is H or C1-C6-alkyl, preferably CH3;

[0675] R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0676] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0677] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0678] In another embodiment, the compound of Formula I is A.20, wherein

[0679] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0680] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0681] R 2 is H or C1-C6-alkyl, preferably CH3;

[0682] R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0683] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0684] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0685] In another embodiment, the compound of formula I is selected from the compounds of formulae I.1 to I.8,

[0686]

[0687] In another embodiment, the compound of formula I is selected from compounds of formula I.1 and I.2;

[0688] In another embodiment, the compound of formula I is selected from compounds of formula I.1 and I.3;

[0689] In another embodiment, the compound of formula I is selected from compounds of formula I.3 and I.4;

[0690] In another embodiment, the compound of formula I is selected from compounds of formula I.2 and I.4;

[0691] In another embodiment, the compound of formula I is selected from compounds of formula I.5 and I.6;

[0692] In another embodiment, the compound of formula I is selected from compounds of formula I.3 and I.7;

[0693] In another embodiment, the compound of formula I is selected from compounds of formula I.5 and I.7;

[0694] In another embodiment, the compound of formula I is selected from compounds of formula I.7 and I.8;

[0695] In another embodiment, the compound of formula I is selected from compounds of formula I.6 and I.8;

[0696] In another embodiment, the compound of formula I is a compound of formula I.1;

[0697] In another embodiment, the compound of formula I is a compound of formula I.2;

[0698] In another embodiment, the compound of formula I is a compound of formula I.3;

[0699] In another embodiment, the compound of formula I is a compound of formula I.4;

[0700] In another embodiment, the compound of formula I is a compound of formula I.5;

[0701] In another embodiment, the compound of formula I is a compound of formula I.6;

[0702] In another embodiment, the compound of formula I is a compound of formula I.7;

[0703] In another embodiment, the compound of formula I is a compound of formula I.8;

[0704] In another embodiment, the compound of formula I is selected from the group consisting of compounds of formulae I.1 to I.8, more preferably I.3 ​​and I.7, wherein

[0705] B 1 Is N or CR B1 , B 2 It's CR B2 , and B 3 It's CR B3 ;

[0706] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0707] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN;

[0708] R A is H, halogen, CN, C1-C6-alkyl or C3-C6-cycloalkyl;

[0709] R 2 is C1-C6-alkyl;

[0710] R 3 is H or C1-C6-alkyl;

[0711] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0712] Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridyl, preferably phenyl, which is unsubstituted or replaced by R Ar1 replace;

[0713] R Ar1is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and C3-C6-heterocyclyl moieties are unsubstituted or replaced by R f 、

[0714] NR b R c 、C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e , -N=S(=O)-(C1-C6-alkyl)2 or S(=O) m R e replace;

[0715] Ar 2 is phenyl, which is unsubstituted or replaced by R Ar2 replace;

[0716] R Ar2 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, wherein these alkyl, alkoxy and cycloalkyl parts are unsubstituted or replaced by halogen,

[0717] NR b R c replace;

[0718] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0719] R d is H or C1-C6-alkyl;

[0720] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0721] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0722] m is 0, 1, or 2.

[0723] In another embodiment, the compound of formula I is selected from the group consisting of compounds of formulae I.1 to I.8, more preferably I.3 ​​and I.7, wherein

[0724] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0725] R A is H, halogen, CN, C1-C6-alkyl or C3-C6-cycloalkyl, preferably CN or CH3;

[0726] R 2 is H or C1-C6-alkyl, preferably CH3;

[0727] B 1 Is N or CR B1 ;

[0728] B 2 Is N or CR B2 ;

[0729] B 3 Is N or CR B3 ;

[0730] B 4 It's CR B4 ;

[0731] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0732] R 3 is H or C1-C6-alkyl;

[0733] R 4 is H or C1-C6-alkyl;

[0734] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0735] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0736] In another embodiment, the compound of formula I is selected from the group consisting of compounds of formulae I.1 to I.8, more preferably I.3 ​​and I.7, wherein

[0737] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0738] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0739] R 2 is H or C1-C6-alkyl, preferably CH3;

[0740] B 1 Is N or CR B1 ;

[0741] B 2 Is N or CR B2 ;

[0742] B 3 Is N or CR B3 ;

[0743] B 4 It's CR B4 ;

[0744] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0745] R 3 is H or C1-C6-alkyl;

[0746] R 4 is H or C1-C6-alkyl;

[0747] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0748] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0749] In another embodiment, the compound of formula I is selected from compounds of formula I.3 and I.7, wherein

[0750] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0751] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0752] R 2 is H or C1-C6-alkyl, preferably CH3;

[0753] B 1 Is N or CR B1 ;

[0754] B 2 Is N or CR B2 ;

[0755] B 3 Is N or CR B3 ;

[0756] B 4 It's CR B4 ;

[0757] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0758] R 3 is H or C1-C6-alkyl;

[0759] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0760] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0761] Ar 2 Selected from Ar 2 -1 to Ar 2-20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0762] In another embodiment, the compound of formula I is selected from compounds of formula I.1 and I.2, wherein

[0763] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0764] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0765] R 2 is H or C1-C6-alkyl, preferably CH3;

[0766] B 1 Is N or CR B1 ;

[0767] B 2 Is N or CR B2 ;

[0768] B 3 Is N or CR B3 ;

[0769] B 4 It's CR B4 ;

[0770] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0771] R 3 is H or C1-C6-alkyl;

[0772] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0773] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0774] Ar2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0775] In another embodiment, the compound of formula I is selected from compounds of formula I.1 and I.3, wherein

[0776] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0777] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0778] R 2 is H or C1-C6-alkyl, preferably CH3;

[0779] B 1 Is N or CR B1 ;

[0780] B 2 Is N or CR B2 ;

[0781] B 3 Is N or CR B3 ;

[0782] B 4 It's CR B4 ;

[0783] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0784] R 3 is H or C1-C6-alkyl;

[0785] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0786] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar1 -5;

[0787] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0788] In another embodiment, the compound of formula I is selected from compounds of formula I.3 and I.4, wherein

[0789] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0790] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0791] R 2 is H or C1-C6-alkyl, preferably CH3;

[0792] B 1 Is N or CR B1 ;

[0793] B 2 Is N or CR B2 ;

[0794] B 3 Is N or CR B3 ;

[0795] B 4 It's CR B4 ;

[0796] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0797] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0798] Ar 2 Selected from Ar 2 -1 to Ar 2-20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0799] In another embodiment, the compound of formula I is selected from compounds of formula I.2 and I.4, wherein

[0800] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0801] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0802] R 2 is H or C1-C6-alkyl, preferably CH3;

[0803] B 1 Is N or CR B1 ;

[0804] B 2 Is N or CR B2 ;

[0805] B 3 Is N or CR B3 ;

[0806] B 4 It's CR B4 ;

[0807] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0808] R 3 is H or C1-C6-alkyl;

[0809] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0810] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0811] Ar2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0812] In another embodiment, the compound of formula I is a compound of formula 1.1, wherein

[0813] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0814] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0815] R 2 is H or C1-C6-alkyl, preferably CH3;

[0816] B 1 Is N or CR B1 ;

[0817] B 2 Is N or CR B2 ;

[0818] B 3 Is N or CR B3 ;

[0819] B 4 It's CR B4 ;

[0820] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0821] R 3 is H or C1-C6-alkyl;

[0822] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0823] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1-5;

[0824] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0825] In another embodiment, the compound of formula I is a compound of formula I.2, wherein

[0826] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0827] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0828] R 2 is H or C1-C6-alkyl, preferably CH3;

[0829] B 1 Is N or CR B1 ;

[0830] B 2 Is N or CR B2 ;

[0831] B 3 Is N or CR B3 ;

[0832] B 4 It's CR B4 ;

[0833] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0834] R 3 is H or C1-C6-alkyl;

[0835] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0836] Ar 1 Selected from Ar 1 -1 to Ar 1-30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0837] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0838] In another embodiment, the compound of formula I is a compound of formula I.3, wherein

[0839] B 1 Is N or CR B1 , B 2 It's CR B2 , and B 3 It's CR B3 ;

[0840] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0841] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN;

[0842] R A is H, halogen, CN, C1-C6-alkyl or C3-C6-cycloalkyl;

[0843] R 2 is C1-C6-alkyl;

[0844] Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridyl, preferably phenyl, which is unsubstituted or replaced by R Ar1 replace;

[0845] R Ar1 is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and C3-C6-heterocyclyl moieties are unsubstituted or replaced by R f 、

[0846] NR b R c 、C(=O)-NRb R c 、C(=O)-R d 、NHS(=O) m R e , -N=S(=O)-(C1-C6-alkyl)2 or S(=O) m R e replace;

[0847] Ar 2 is phenyl, which is unsubstituted or replaced by R Ar2 replace;

[0848] R Ar2 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, wherein these alkyl, alkoxy and cycloalkyl parts are unsubstituted or replaced by halogen,

[0849] NR b R c replace;

[0850] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0851] R d is H or C1-C6-alkyl;

[0852] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0853] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0854] m is 0, 1, or 2.

[0855] In another embodiment, the compound of formula I is a compound of formula I.3, wherein

[0856] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0857] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0858] R 2is H or C1-C6-alkyl, preferably CH3;

[0859] B 1 Is N or CR B1 ;

[0860] B 2 Is N or CR B2 ;

[0861] B 3 Is N or CR B3 ;

[0862] B 4 It's CR B4 ;

[0863] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0864] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0865] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0866] In another embodiment, the compound of formula I is a compound of formula I.4, wherein

[0867] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0868] R A is H, CN or C1-C6-alkyl, preferably CN or CH3;

[0869] R 2 is H or C1-C6-alkyl, preferably CH3;

[0870] B 1 Is N or CR B1 ;

[0871] B 2 Is N or CR B2 ;

[0872] B 3 Is N or CR B3 ;

[0873] B 4 It's CR B4 ;

[0874] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0875] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0876] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0877] In another embodiment, the compound of formula I is selected from compounds of formula I.5 and I.6, wherein

[0878] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0879] R 2 is H or C1-C6-alkyl, preferably CH3;

[0880] B 1 Is N or CR B1 ;

[0881] B 2 Is N or CR B2 ;

[0882] B 3 Is N or CR B3 ;

[0883] B 4 It's CR B4;

[0884] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0885] R 3 is H or C1-C6-alkyl;

[0886] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0887] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0888] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0889] In another embodiment, the compound of formula I is selected from compounds of formula I.5 and I.7, wherein

[0890] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0891] R 2 is H or C1-C6-alkyl, preferably CH3;

[0892] B 1 Is N or CR B1 ;

[0893] B 2 Is N or CR B2 ;

[0894] B 3 Is N or CR B3 ;

[0895] B 4 It's CR B4 ;

[0896] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0897] R 3 is H or C1-C6-alkyl;

[0898] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0899] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0900] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0901] In another embodiment, the compound of formula I is selected from compounds of formula I.7 and I.8, wherein

[0902] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0903] R 2 is H or C1-C6-alkyl, preferably CH3;

[0904] B 1 Is N or CR B1 ;

[0905] B 2 Is N or CR B2 ;

[0906] B 3 Is N or CR B3 ;

[0907] B 4 It's CR B4 ;

[0908] R B1 、RB2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0909] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0910] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0911] In another embodiment, the compound of formula I is selected from compounds of formula I.6 and I.8, wherein

[0912] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0913] R 2 is H or C1-C6-alkyl, preferably CH3;

[0914] B 1 Is N or CR B1 ;

[0915] B 2 Is N or CR B2 ;

[0916] B 3 Is N or CR B3 ;

[0917] B 4 It's CR B4 ;

[0918] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0919] R 3is H or C1-C6-alkyl;

[0920] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0921] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0922] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0923] In another embodiment, the compound of formula I is a compound of formula 1.5, wherein

[0924] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0925] R 2 is H or C1-C6-alkyl, preferably CH3;

[0926] B 1 Is N or CR B1 ;

[0927] B 2 Is N or CR B2 ;

[0928] B 3 Is N or CR B3 ;

[0929] B 4 It's CR B4 ;

[0930] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0931] R 3 is H or C1-C6-alkyl;

[0932] R 4 is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy;

[0933] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0934] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0935] In another embodiment, the compound of formula I is a compound of formula 1.6, wherein

[0936] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0937] R 2 is H or C1-C6-alkyl, preferably CH3;

[0938] B 1 Is N or CR B1 ;

[0939] B 2 Is N or CR B2 ;

[0940] B 3 Is N or CR B3 ;

[0941] B 4 It's CR B4 ;

[0942] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0943] R 3 is H or C1-C6-alkyl;

[0944] R 4is H or C1-C6-alkyl, which is unsubstituted or substituted by -O-(C=O)-C1-C6-alkoxy; /

[0945] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0946] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0947] In another embodiment, the compound of formula I is a compound of formula 1.7, wherein

[0948] B 1 Is N or CR B1 , B 2 It's CR B2 , and B 3 It's CR B3 ;

[0949] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0950] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN;

[0951] R 2 is C1-C6-alkyl;

[0952] Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridyl, preferably phenyl, which is unsubstituted or replaced by R Ar1 replace;

[0953] R Ar1 is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and C3-C6-heterocyclyl moieties are unsubstituted or replaced by R f 、

[0954] NR b R c 、C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e , -N=S(=O)-(C1-C6-alkyl)2 or S(=O) m R e replace;

[0955] Ar 2 is phenyl, which is unsubstituted or replaced by R Ar2 replace;

[0956] R Ar2 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, wherein these alkyl, alkoxy and cycloalkyl parts are unsubstituted or replaced by halogen,

[0957] NR b R c replace;

[0958] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0959] R d is H or C1-C6-alkyl;

[0960] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0961] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0962] m is 0, 1, or 2.

[0963] In another embodiment, the compound of formula I is a compound of formula 1.7, wherein

[0964] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0965] R 2 is H or C1-C6-alkyl, preferably CH3;

[0966] B 1 Is N or CR B1 ;

[0967] B 2 Is N or CR B2 ;

[0968] B 3 Is N or CR B3 ;

[0969] B 4 It's CR B4 ;

[0970] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0971] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0972] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0973] In another embodiment, the compound of formula I is a compound of formula I.8, wherein

[0974] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN, preferably H, CH3, C2H5 or -CH2-CN, more preferably H or CH3;

[0975] R 2 is H or C1-C6-alkyl, preferably CH3;

[0976] B 1 Is N or CR B1 ;

[0977] B 2 Is N or CR B2 ;

[0978] B 3 Is N or CRB3 ;

[0979] B 4 It's CR B4 ;

[0980] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0981] Ar 1 Selected from Ar 1 -1 to Ar 1 -30, preferably selected from Ar 1 -1 to Ar 1 -5;

[0982] Ar 2 Selected from Ar 2 -1 to Ar 2 -20, preferably selected from Ar 2 -1 to Ar 2 -6;

[0983] Specific compounds of formula I are the compounds of formulae I.3, I.4, I.7 and I.8 compiled in Tables 1 to 720 below, wherein the variable B of each compound of Tables 1 to 720 is 1 、B 2 、B 3 and B 4 A combination of corresponds to each row of Table B. Each radical of the substituents mentioned in the table is furthermore on its own (independently of the combination in which it is mentioned) a particularly preferred aspect of the substituent in question.

[0984] Table 1. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[0985] Table 2. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[0986] Table 3. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[0987] Table 4. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -4.

[0988] Table 5. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -5.

[0989] Table 6. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -6.

[0990] Table 7. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[0991] Table 8. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[0992] Table 9. Compounds of formula I.3, wherein R AIt is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[0993] Table 10. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -4.

[0994] Table 11. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -5.

[0995] Table 12. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -6.

[0996] Table 13. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[0997] Table 14. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[0998] Table 15. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -3.

[0999] Table 16. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -4.

[1000] Table 17. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -5.

[1001] Table 18. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1002] Table 19. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -1.

[1003] Table 20. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -2.

[1004] Table 21. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1-4,Ar 2 It is Ar 2 -3.

[1005] Table 22. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1006] Table 23. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -5.

[1007] Table 24. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1008] Table 25. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1009] Table 26. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1010] Table 27. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2-3.

[1011] Table 28. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1012] Table 29. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -5.

[1013] Table 30. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1014] Table 31. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[1015] Table 32. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[1016] Table 33. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[1017] Table 34. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -4.

[1018] Table 35. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -5.

[1019] Table 36. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -6.

[1020] Table 37. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[1021] Table 38. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[1022] Table 39. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[1023] Table 40. Compounds of formula I.3, wherein RA It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -4.

[1024] Table 41. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -5.

[1025] Table 42. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -6.

[1026] Table 43. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[1027] Table 44. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[1028] Table 45. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -3.

[1029] Table 46. Compounds of formula I.3, wherein R A It is CN, R2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -4.

[1030] Table 47. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -5.

[1031] Table 48. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1032] Table 49. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -1.

[1033] Table 50. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -2.

[1034] Table 51. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -3.

[1035] Table 52. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1036] Table 53. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -5.

[1037] Table 54. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1038] Table 55. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1039] Table 56. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1040] Table 57. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -3.

[1041] Table 58. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1042] Table 59. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -5.

[1043] Table 60. Compounds of formula I.3, wherein R A It is CN, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1044] Table 61. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[1045] Table 62. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[1046] Table 63. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[1047] Table 64. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar1 -1,Ar 2 It is Ar 2 -4.

[1048] Table 65. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -5.

[1049] Table 66. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -6.

[1050] Table 67. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[1051] Table 68. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[1052] Table 69. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[1053] Table 70. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar2 It is Ar 2 -4.

[1054] Table 71. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -5.

[1055] Table 72. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -6.

[1056] Table 73. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[1057] Table 74. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[1058] Table 75. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -3.

[1059] Table 76. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar2 -4.

[1060] Table 77. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -5.

[1061] Table 78. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1062] Table 79. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -1.

[1063] Table 80. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -2.

[1064] Table 81. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -3.

[1065] Table 82. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1066] Table 83. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -5.

[1067] Table 84. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1068] Table 85. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1069] Table 86. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1070] Table 87. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -3.

[1071] Table 88. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1072] Table 89. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -5.

[1073] Table 90. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1074] Table 91. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[1075] Table 92. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[1076] Table 93. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[1077] Table 94. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -4.

[1078] Table 95. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -5.

[1079] Table 96. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -6.

[1080] Table 97. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[1081] Table 98. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[1082] Table 99. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[1083] Table 100. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -4.

[1084] Table 101. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -5.

[1085] Table 102. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -6.

[1086] Table 103. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[1087] Table 104. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[1088] Table 105. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -3.

[1089] Table 106. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -4.

[1090] Table 107. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -5.

[1091] Table 108. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1092] Table 109. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -1.

[1093] Table 110. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -2.

[1094] Table 111. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -3.

[1095] Table 112. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1096] Table 113. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -5.

[1097] Table 114. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1098] Table 115. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1099] Table 116. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1100] Table 117. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -3.

[1101] Table 118. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1102] Table 119. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -5.

[1103] Table 120. Compounds of formula I.3, wherein R A It is CN, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1104] Table 121. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[1105] Table 122. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[1106] Table 123. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[1107] Table 124. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -4.

[1108] Table 125. Compounds of formula I.3, wherein RA It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -5.

[1109] Table 126. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -6.

[1110] Table 127. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[1111] Table 128. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[1112] Table 129. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[1113] Table 130. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -4.

[1114] Table 131. Compounds of formula I.3, wherein R A It is CH3, R2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -5.

[1115] Table 132. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -6.

[1116] Table 133. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[1117] Table 134. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[1118] Table 135. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -3.

[1119] Table 136. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -4.

[1120] Table 137. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -5.

[1121] Table 138. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1122] Table 139. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -1.

[1123] Table 140. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -2.

[1124] Table 141. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -3.

[1125] Table 142. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1126] Table 143. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar1 It is Ar 1 -4,Ar 2 It is Ar 2 -5.

[1127] Table 144. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1128] Table 145. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1129] Table 146. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1130] Table 147. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -3.

[1131] Table 148. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1132] Table 149. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar1 -5,Ar 2 It is Ar 2 -5.

[1133] Table 150. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1134] Table 151. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[1135] Table 152. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[1136] Table 153. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[1137] Table 154. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -4.

[1138] Table 155. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1-1,Ar 2 It is Ar 2 -5.

[1139] Table 156. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -6.

[1140] Table 157. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[1141] Table 158. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[1142] Table 159. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[1143] Table 160. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -4.

[1144] Table 161. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar2 It is Ar 2 -5.

[1145] Table 162. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -6.

[1146] Table 163. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[1147] Table 164. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[1148] Table 165. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -3.

[1149] Table 166. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -4.

[1150] Table 167. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2It is Ar 2 -5.

[1151] Table 168. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1152] Table 169. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -1.

[1153] Table 170. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -2.

[1154] Table 171. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -3.

[1155] Table 172. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1156] Table 173. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar2 -5.

[1157] Table 174. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1158] Table 175. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1159] Table 176. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1160] Table 177. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -3.

[1161] Table 178. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1162] Table 179. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2-5.

[1163] Table 180. Compounds of formula I.3, wherein R A It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1164] Table 181. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[1165] Table 182. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[1166] Table 183. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[1167] Table 184. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -4.

[1168] Table 185. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -5.

[1169] Table 186. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -6.

[1170] Table 187. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[1171] Table 188. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[1172] Table 189. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[1173] Table 190. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -4.

[1174] Table 191. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -5.

[1175] Table 192. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -6.

[1176] Table 193. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[1177] Table 194. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[1178] Table 195. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -3.

[1179] Table 196. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -4.

[1180] Table 197. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -5.

[1181] Table 198. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1182] Table 199. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -1.

[1183] Table 200. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -2.

[1184] Table 201. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -3.

[1185] Table 202. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1186] Table 203. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -5.

[1187] Table 204. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1188] Table 205. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1189] Table 206. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1190] Table 207. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -3.

[1191] Table 208. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1192] Table 209. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -5.

[1193] Table 210. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1194] Table 211. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[1195] Table 212. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[1196] Table 213. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[1197] Table 214. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -4.

[1198] Table 215. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -5.

[1199] Table 216. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -6.

[1200] Table 217. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[1201] Table 218. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[1202] Table 219. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[1203] Table 220. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -4.

[1204] Table 221. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -5.

[1205] Table 222. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -6.

[1206] Table 223. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[1207] Table 224. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[1208] Table 225. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -3.

[1209] Table 226. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -4.

[1210] Table 227. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -5.

[1211] Table 228. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1212] Table 229. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -1.

[1213] Table 230. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -2.

[1214] Table 231. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -3.

[1215] Table 232. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1216] Table 233. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -5.

[1217] Table 234. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1218] Table 235. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1219] Table 236. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1220] Table 237. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -3.

[1221] Table 238. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1222] Table 239. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -5.

[1223] Table 240. Compounds of formula I.3, wherein R A It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1224] Table 241. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[1225] Table 242. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[1226] Table 243. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[1227] Table 244. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -4.

[1228] Table 245. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -5.

[1229] Table 246. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2-6.

[1230] Table 247. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[1231] Table 248. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[1232] Table 249. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[1233] Table 250. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -4.

[1234] Table 251. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -5.

[1235] Table 252. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -6.

[1236] Table 253. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar2 -1.

[1237] Table 254. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[1238] Table 255. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -3.

[1239] Table 256. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -4.

[1240] Table 257. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -5.

[1241] Table 258. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1242] Table 259. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -1.

[1243] Table 260. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2It is Ar 2 -2.

[1244] Table 261. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -3.

[1245] Table 262. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1246] Table 263. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -5.

[1247] Table 264. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1248] Table 265. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1249] Table 266. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1250] Table 267. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar2 It is Ar 2 -3.

[1251] Table 268. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1252] Table 269. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -5.

[1253] Table 270. Compounds of formula I.7, wherein R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1254] Table 271. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[1255] Table 272. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[1256] Table 273. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[1257] Table 274. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar1 -1,Ar 2 It is Ar 2 -4.

[1258] Table 275. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -5.

[1259] Table 276. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -6.

[1260] Table 277. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[1261] Table 278. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[1262] Table 279. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[1263] Table 280. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -4.

[1264] Table 281. Compounds of formula I.7, wherein R 2 It's H, R 5is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -5.

[1265] Table 282. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -6.

[1266] Table 283. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[1267] Table 284. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[1268] Table 285. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -3.

[1269] Table 286. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -4.

[1270] Table 287. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -5.

[1271] Table 288. Compounds of formula I.7, wherein R2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1272] Table 289. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -1.

[1273] Table 290. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -2.

[1274] Table 291. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -3.

[1275] Table 292. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1276] Table 293. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -5.

[1277] Table 294. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1278] Table 295. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1279] Table 296. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1280] Table 297. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -3.

[1281] Table 298. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1282] Table 299. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -5.

[1283] Table 300. Compounds of formula I.7, wherein R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1284] Table 301. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[1285] Table 302. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[1286] Table 303. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[1287] Table 304. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -4.

[1288] Table 305. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -5.

[1289] Table 306. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -6.

[1290] Table 307. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[1291] Table 308. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2It is Ar 2 -2.

[1292] Table 309. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[1293] Table 310. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -4.

[1294] Table 311. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -5.

[1295] Table 312. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -6.

[1296] Table 313. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[1297] Table 314. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[1298] Table 315. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar1 -3,Ar 2 It is Ar 2 -3.

[1299] Table 316. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -4.

[1300] Table 317. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -5.

[1301] Table 318. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1302] Table 319. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -1.

[1303] Table 320. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -2.

[1304] Table 321. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -3.

[1305] Table 322. Compounds of formula I.7, wherein R 2 It is CH3, R 5It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1306] Table 323. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -5.

[1307] Table 324. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1308] Table 325. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1309] Table 326. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1310] Table 327. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -3.

[1311] Table 328. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1312] Table 329. Compounds of formula I.7, wherein R 2It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -5.

[1313] Table 330. Compounds of formula I.7, wherein R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1314] Table 331. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[1315] Table 332. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[1316] Table 333. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -3.

[1317] Table 334. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -4.

[1318] Table 335. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -5.

[1319] Table 336. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -6.

[1320] Table 337. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[1321] Table 338. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[1322] Table 339. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -3.

[1323] Table 340. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -4.

[1324] Table 341. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -5.

[1325] Table 342. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar2 -6.

[1326] Table 343. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[1327] Table 344. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[1328] Table 345. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -3.

[1329] Table 346. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -4.

[1330] Table 347. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -5.

[1331] Table 348. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -6.

[1332] Table 349. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar1 -4,Ar 2 It is Ar 2 -1.

[1333] Table 350. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -2.

[1334] Table 351. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -3.

[1335] Table 352. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -4.

[1336] Table 353. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -5.

[1337] Table 354. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -4,Ar 2 It is Ar 2 -6.

[1338] Table 355. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -1.

[1339] Table 356. Compounds of formula I.7, wherein R 2 It is CH3, R5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -2.

[1340] Table 357. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -3.

[1341] Table 358. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -4.

[1342] Table 359. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -5.

[1343] Table 360. Compounds of formula I.7, wherein R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -5,Ar 2 It is Ar 2 -6.

[1344] Table B:

[1345]

[1346]

[1347]

[1348]

[1349]

[1350]

[1351]

[1352]

[1353]

[1354]

[1355]

[1356]

[1357]

[1358]

[1359]

[1360]

[1361]

[1362] Tables 361 to 600: include all compounds disclosed in Tables 1 to 240, respectively, wherein the compound of formula I.3 is replaced by a compound of formula I.4;

[1363] Tables 601 to 720: include all compounds disclosed in Tables 241 to 360, respectively, wherein the compound of formula I.7 is replaced by a compound of formula I.8;

[1364] The term "compound(s) of the invention" refers to one or more compounds of Formula I or "compound(s) I," and includes salts, tautomers, stereoisomers, and N-oxides thereof.

[1365] The invention furthermore relates to agrochemical compositions comprising an adjuvant and at least one compound I.

[1366] The agrochemical composition comprises a pesticidally effective amount of compound I.

[1367] Compound I can be converted into agrochemical compositions of conventional types, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, compressed tablets, capsules, and mixtures thereof. Examples of composition types are suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, pastilles, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), compressed tablets (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticide preparations (e.g., LN), and gel formulations (e.g., GF) for treating plant propagation materials (e.g., seeds). These and other composition types are defined in "Catalogue of pesticide formulation types and international coding system," Technical Monograph, No. 2, 6th edition, May 2008, CropLife International. These compositions are prepared in a known manner, as described, for example, by Mollet and Grubermann, Formulation technology, Wiley VCH, Weinheim, 2001, or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[1368] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, tackifiers and adhesives.

[1369] Suitable solvents and liquid carriers are water and organic solvents. Suitable solid carriers or fillers are mineral soils.

[1370] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids or adjuvants. Surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents [emulsifiers and detergents], McCutcheon's Directories [McCutcheon's Directory], Glen Rock, USA, 2008 (International Edition or North American Edition). Suitable anionic surfactants are alkali metal salts, alkaline earth metal salts or ammonium salts of sulfonic acid, sulfuric acid, phosphoric acid, carboxylic acids. Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants. Suitable cationic surfactants are quaternary ammonium surfactants.

[1371] Agrochemical compositions generally contain between 0.01% and 95%, preferably between 0.1% and 90%, and most preferably between 0.5% and 75% by weight of active substance. The active substance is used in a purity of 90% to 100%, preferably 95% to 100%.

[1372] Various types of oils, wetting agents, adjuvants, or fertilizers can be added as premixes or, if appropriate, not added until just before use (tank mix) to the active substances or compositions comprising them. These agents can be mixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1.

[1373] The user usually applies the composition according to the present invention by a pre-dosing device, a backpack sprayer, a spray can, a spray plane, or an irrigation system. Usually, the agrochemical composition is made of water, a buffer and / or another adjuvant to the desired application concentration, and thus obtains the ready-to-use spray liquid or agrochemical composition according to the present invention. Usually, 20 to 2000 liters of ready-to-use spray liquid are applied per hectare of agricultural useful area.

[1374] Compound I is suitable for protecting crops, plants, plant propagation materials (e.g. seeds) or soil or water bodies in which plants grow from attack or infestation by animal pests. Therefore, the present invention also relates to a method for protecting plants, which comprises contacting crops, plants, plant propagation materials (e.g. seeds) or soil or water bodies in which plants grow to be protected from attack or infestation by animal pests with a pesticidally effective amount of compound I.

[1375] Compound I is also suitable for combating or controlling animal pests. Therefore, the present invention also relates to a method for combating or controlling animal pests, which method comprises contacting the animal pests, their habitat, breeding ground, or food supply, or crops, plants, plant propagation material (e.g. seeds), or soil, or areas, materials or environments where the animal pests grow or may grow with a pesticidally effective amount of compound I.

[1376] Compound I is effective against any and all developmental stages, such as eggs, larvae, pupae, and adults, by both contact and ingestion.

[1377] Compound I can be administered as such or in the form of a composition comprising them.

[1378] Application can be carried out before or after crops, plants or plant propagation materials are infested by pests.

[1379] The term "contacting" includes both direct contact (applying the compound / composition directly to the animal pest or plant) and indirect contact (applying the compound / composition to the locus).

[1380] The term "animal pests" includes arthropods, gastropods, and nematodes. Preferred animal pests according to the present invention are arthropods, preferably insects and arachnids, in particular insects.

[1381] The term "plant" includes cereals such as durum wheat and other wheats, rye, barley, triticale, oats, rice, or maize (fodder maize and sweet maize / sweet corn and field corn); beets such as sugar beets or fodder beets; fruits such as pome fruits, stone fruits, or soft fruits such as apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries, or gooseberries; leguminous plants such as beans, lentils, peas, alfalfa, or soybeans; oilseed plants such as rapeseed (oilseed rape), Brassica rapa, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palm, peanuts, or soybeans; cucurbits such as winter squash, pumpkin, cucumber, or melon; fibers. Plants such as cotton, flax, hemp, or jute; citrus fruits such as oranges, lemons, grapefruits, or mandarins; vegetables such as eggplant, spinach, lettuce (e.g., iceberg lettuce), chicory, cabbage, asparagus, cabbage, carrots, onions, garlic, leeks, tomatoes, potatoes, gourds, or bell peppers; laurel plants such as avocado, cinnamon, or camphor; energy and feedstock plants such as corn, soybeans, rapeseed, sugarcane, or oil palm; tobacco; nuts such as walnuts; pistachios; coffee; tea; bananas; vines; hops; stevia (Stevia); natural rubber plants or ornamental and forestry plants, shrubs, broadleaf trees, or evergreen plants, eucalyptus; turf; lawns; grasses. Preferred plants include potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, beans, sunflower, coffee, or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans, or squash.

[1382] The term "seed" includes seeds and plant propagules, including true seeds, seed pieces, suckers, corms, bulbs, fruits, tubers, kernels, cuttings, cut shoots, and preferably means true seeds.

[1383] "Pesticidally effective amount" means the amount of active ingredient required to achieve an observable effect on growth, including necrosis, mortality, retardation, prevention and removal, destruction or otherwise reduction of the presence and activity of the target organism. The pesticidally effective amount can vary for the various compounds / compositions used in the present invention. The pesticidally effective amount of a composition will also vary depending on prevailing conditions, such as the desired pesticidal effect and duration, climate, target species, location, and mode of application.

[1384] For use in treating crop plants, for example by foliar application, the application rate of the active ingredient of the invention may be in the range of 0.0001 g to 4000 g per hectare, for example 1 g to 2 kg per hectare or 1 g to 750 g per hectare, ideally 1 g to 100 g per hectare.

[1385] Compound I is also suitable for use against non-crop insect pests. For use against such non-crop pests, Compound I can be used as bait compositions, gels, conventional insect sprays, aerosols, as ultra-low volume applications and mosquito nets (impregnation or surface application).

[1386] The term "non-crop insect pests" refers to pests that are particularly associated with non-crop targets, for example, ants, termites, wasps, flies, ticks, mosquitoes, bedbugs, crickets, or cockroaches, such as: Aedes aegypti, Musca domestica, Tribolium spp.; termites, such as Reticulitermes flavipes, Coptotermes formosanus; cockroaches, such as Blattella germanica, Periplaneta americana; ants, such as Solenopsis invicta, Linepithema humile, and Camponotus pennsylvanicus.

[1387] The bait may be a liquid, solid or semi-solid formulation (eg a gel).For use in a bait composition, typical levels of active ingredient are from 0.001 wt% to 15 wt%, ideally from 0.001 wt% to 5 wt% of active compound.

[1388] Compound I and its compositions can be used to protect wooden materials, such as trees, wooden fences, sleepers, frames, artworks, etc., as well as buildings, building materials, furniture, leather, fibers, vinyl products, wires and cables, etc., from ants, termites and / or beetles that destroy wood or textiles, and to control ants and termites from causing damage to crops or humans (for example, when pests invade houses and public facilities or nest in yards, orchards or parks).

[1389] Typical application rates for protective materials are e.g. 2 Treatment material 0.001 g to 2000 g or 0.01 g to 1000 g of active compound, ideally per m 2 0.1g to 50g.

[1390] Insecticidal compositions for use in impregnating materials typically contain 0.001 wt% to 95 wt%, preferably 0.1 wt% to 45 wt%, and more preferably 1 wt% to 25 wt% of at least one repellent and / or insecticide.

[1391] Pests

[1392] The compounds of the present invention are particularly suitable for use against animal pests, such as arthropods and nematodes, including:

[1393] Insects from the following suborder: Auchenorrhyncha, for example, Amrasca biguttula, Empoasca spp., Nephotettix virescens, Sogatella furcifera, Mahanarva spp., Laodelphax striatellus, Nilaparvata lugens, Diaphorina citri;

[1394] From the order of the Lepidoptera, for example, Helicoverpa spp., Heliothis virescens, Lobesia botrana, Ostrinianubilalis, Plutella xylostella, Pseudoplusia includens, Scirpophaga incertulas, Spodoptera spp., Trichoplusia ni, Tuta absoluta, Cnaphalocrocis medialis, Cydia pomonella, Chilo suppressalis, Anticarsia gemmatalis, Agrotis ipsilon, Chrysodeixis includens;

[1395] True bugs, for example Lygus spp., stink bugs such as Euschistus spp., Halyomorpha halys, Nezara viridula, Piezodorus guildinii, Dichelops furcatus;

[1396] Thrips, e.g., Frankliniella spp., Thrips spp., Dichromothrips corbettii;

[1397] Aphids, for example Acyrthosiphon pisum, Aphis spp., Myzus persicae, Rhopalosiphum spp., Schizaphis graminum, Megoura viciae;

[1398] Whiteflies, such as greenhouse whitefly (Trialeurodes vaporariorum), Bemisia spp.;

[1399] From the order of the Coleoptera, for example, Phyllotreta spp., Melanotus spp., Meligethes aeneus, Leptinotarsa ​​decimlineata, Ceutorhynchus spp., Diabrotica spp., Anthonomus grandis, Atomaria linearia, Agriotes spp., Epilachna spp.;

[1400] Flies, for example Delia spp., Ceratitis capitata, Bactrocera spp., Liriomyza spp.;

[1401] Coccoidea, such as Aonidiella aurantii and Ferrisia virgate;

[1402] Arthropods (mites) of the class Arachnida, for example, Penthaleus major and Tetranychus spp.;

[1403] Nematodes, for example, Heterodera glycines, Meloidogyne spp., Pratylenchus spp., Caenorhabditis elegans.

[1404] Animal Health

[1405] Compound I is suitable for treating or protecting animals from parasitic infestation or infection. Therefore, the present invention also relates to the use of the compounds of the present invention for the manufacture of a medicament for treating or protecting animals from parasitic infestation or infection. In addition, the present invention relates to a method for treating or protecting animals from parasitic infestation and infection, which method comprises administering or applying to the animal orally, topically or parenterally a parasiticidally effective amount of Compound I.

[1406] The present invention also relates to the non-therapeutic use of the compounds of the present invention for treating or protecting animals from parasitic infestation and infection. In addition, the present invention relates to a non-therapeutic method for treating or protecting animals from parasitic infestation and infection, which comprises applying a parasiticidally effective amount of Compound I to the site.

[1407] The compounds of the present invention are further suitable for use in combating or controlling parasites in and on animals. In addition, the present invention relates to a method for combating or controlling parasites in and on animals, which method comprises contacting the parasite with a parasiticidally effective amount of compound I.

[1408] The present invention also relates to non-therapeutic uses of Compound I for controlling or combating parasites. In addition, the present invention relates to a non-therapeutic method for combating or controlling parasites, which comprises applying a parasiticidally effective amount of Compound I to a location.

[1409] Compound 1 can be effective by both contact (via soil, glass, walls, mosquito nets, carpets, rugs or animal parts) and ingestion (e.g., baits). In addition, Compound 1 can be applied to any and all developmental stages.

[1410] Compound I can be administered as such or in the form of a composition comprising them.

[1411] The term "locus" means a habitat, food supply, breeding ground, area, material or environment outside an animal where a parasite is or may be growing.

[1412] As used herein, the term "parasite" includes both endoparasites and ectoparasites. In some embodiments of the present invention, endoparasites may be preferred. In other embodiments, ectoparasites may be preferred. Infestations in warm-blooded animals and fish include lice, biting lice, ticks, maggots, gnats, houseflies, flies, maggot fly larvae, chiggers, gnats, mosquitoes, and fleas.

[1413] The compounds of the invention are particularly useful against the following parasites: Cimex lectularius, Rhipicephalus sanguineus and Ctenocephalides felis.

[1414] As used herein, the term "animal" includes warm-blooded animals (including humans) and fish. Preferred are mammals such as cattle, sheep, pigs, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, buffaloes, donkeys, fallow deer and reindeer, as well as fur animals such as mink, chinchillas and raccoons, birds such as hens, geese, turkeys and ducks, and fish such as freshwater fish and saltwater fish such as salmon, carp and eels. Particularly preferred are domestic animals such as dogs or cats.

[1415] Compound I may be administered in a total amount of 0.5 mg / kg to 100 mg / kg / day, preferably 1 mg / kg to 50 mg / kg / day.

[1416] For oral administration to warm-blooded animals, Compound I can be formulated into animal feeds, animal feed premixes, animal feed concentrates, pellets, solutions, pastes, suspensions, immersions, gels, tablets, boluses, and capsules. For oral administration, the dosage form selected should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day, preferably 0.5 mg / kg to 100 mg / kg of animal body weight per day of Compound I.

[1417] Alternatively, Compound 1 can be administered to animals parenterally, for example, by intracavitary, intramuscular, intravenous or subcutaneous injection. For subcutaneous injection, Compound 1 can be dispersed or dissolved in a physiologically acceptable carrier. Alternatively, Compound 1 can be formulated as an implant for subcutaneous administration. In addition, Compound 1 can be administered to animals transdermally. For parenteral administration, the selected dosage form should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight / day of Compound 1.

[1418] Compound I can also be applied topically to animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations, as well as ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays typically contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of Compound I. In addition, Compound I can be formulated as ear tags for animals, particularly quadrupeds (e.g., cattle and sheep).

[1419] Oral solution is given directly.

[1420] Solutions for use on the skin are applied by dripping, spreading, rubbing, sprinkling or spraying.

[1421] The gel is applied or spread on the skin or introduced into a body cavity.

[1422] Pour-on formulations are sprayed or applied to defined areas of the skin, where the active compound penetrates the skin and acts systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in a suitable skin-compatible solvent or solvent mixture.

[1423] The emulsion can be administered orally, transdermally, or as an injection.

[1424] The suspension may be administered orally or topically / dermally.

[1425] Semisolid preparations can be administered orally or topically / dermally.

[1426] To produce solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.

[1427] Compositions useful in the present invention may generally contain Compound I in an amount of from about 0.001% to about 95%.

[1428] The ready-to-use preparations contain the compound acting against parasites, preferably ectoparasites, in a concentration of 10 ppm to 80% by weight, preferably 0.1% to 65% by weight, more preferably 1% to 50% by weight, most preferably 5% to 40% by weight.

[1429] The preparations to be diluted before use contain the compounds active against ectoparasites in a concentration of 0.5% to 90% by weight, preferably 1% to 50% by weight.

[1430] Furthermore, the preparations comprise compounds of the formula I acting against endoparasites in a concentration of 10 ppm to 2% by weight, preferably 0.05% to 0.9% by weight, very particularly preferably 0.005% to 0.25% by weight.

[1431] Solid formulations releasing the compound of the invention in a total amount of 10 to 300 mg / kg, preferably 20 to 200 mg / kg, most preferably 25 to 160 mg / kg of the treated animal body weight over three weeks may be administered.

[1432] Examples:

[1433] By appropriately varying the starting materials, the procedures described in the preparation examples below were used to obtain further compounds of the formula I. The compounds obtained in this way are listed together with the physical data in Table C below.

[1434] Compounds can be detected by, for example, coupled high performance liquid chromatography / mass spectrometry (HPLC / MS), 1 The samples were characterized by H NMR and / or their melting points.

[1435] Compounds can be detected by, for example, coupled high performance liquid chromatography / mass spectrometry (HPLC / MS), 1 The samples were characterized by H NMR and / or their melting points.

[1436] Analytical HPLC - Method 1: Agilent Eclipse Plus C18, 50X 4,6 mm, ID 5 μm; Elution: A = 10 mM ammonium formate (0.1% formic acid), B = acetonitrile (0.1% formic acid), flow rate = 1.2 ml / min at 30°C; Gradient: 10% B to 100% B - 3 min, hold 1 min, 1 min - 10% B. Run time = 5.01 min.

[1437] Analytical HPLC - Method 2: Kinetex XB C18 1,7μ 50 x 2,1 mm; A = water + 0.1% TFA, B = acetonitrile, flow rate = 0.8 ml / min - 1.0 ml / min in 1.5 min at 60°C; gradient: 5% B to 100% B - 1.5 min.

[1438] Analytical HPLC-Method 3: Diamonsil plus 5μm, 30x3,0mm; A=water+0.05% TFA, B=acetonitrile, flow rate=2ml / min at 40°C; gradient: 5% B to 95% B-0.8min, hold 0.75min, then 95% B to 5% B-0.25min.

[1439] 1 H NMR: Signals are expressed relative to tetramethylsilane (corresponding to 13C-NMR is characterized by chemical shifts (ppm, d[δ]) in CDCl3), their multiplicity and their completeness (relative number of given hydrogen atoms). The following abbreviations are used to characterize the multiplicity of the signals: m = multiplet, q = quartet, t = triplet, d = doublet, and s = singlet.

[1440] Abbreviations used are: d for day, h for hour, min for minute, RT / room temperature for 20°C-25°C, Rt for retention time; DMSO for dimethyl sulfoxide, OAc for acetate, EtOAc for ethyl acetate, IPA for isopropanol, MeOH for methanol, EtOH for ethanol, THF for tetrahydrofuran, DCM for dichloromethane, DMF for N,N-dimethylformamide, and t-BuOH for tert-butanol.

[1441] Example C-1:

[1442] Preparation of N-[5-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide (C-1)

[1443] Step 1: Synthesis of 3-(4-bromophenyl)-2-methyl-3-oxo-propionitrile

[1444] To the stirred solution of 4-bromobenzoic acid ethyl ester (30g) in THF (600mL) at ambient temperature, potassium tert-butoxide (29.39g) was added. After 10min, propionitrile (7.213g) was added to the reaction mass at ambient temperature. The reaction mixture was stirred for 1h at ambient temperature, and after the reaction was complete, the mixture was diluted in water. The mixture was extracted with EtOAc, and the organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo to obtain the title compound (24g) in a light yellow oil.

[1445] HPLC / MS (method 1): Rt: 1.821 min; m / z = 236 (M-1) + .

[1446] Step 2: Synthesis of 5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-amine

[1447] To a stirred solution of 3-(4-bromophenyl)-2-methyl-3-oxo-propionitrile (25 g) in EtOH (250 mL) was added methylhydrazine (26.181 g, 85% solution) at ambient temperature. The reaction mixture was heated at 85 ° C for 16 h, and after the reaction was complete, EtOH was removed under reduced pressure and the crude product was dissolved in water. The mixture was extracted with EtOAc, and the organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo to give the title compound (23 g) as a solid.

[1448] HPLC / MS (method 1): Rt: 1.656 min; m / z = 266 (M+1) + .

[1449] Step 3: Synthesis of N-[5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide

[1450] To a stirred solution of 5-(4-bromophenyl)-2,4-dimethyl-pyrazole-3-amine (43.5 g) in DCM (430 mL) was added 4-(trifluoromethyl)benzoic acid (31.075 g), N,N,N-diisopropylethylamine (118.29 g) and propylphosphonic anhydride (312.03 g, 50% solution in EtOAc) at ambient temperature. The reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was dissolved in water and the mixture was extracted with DCM. The organic extract was washed with 1N hydrochloric acid, dried over anhydrous sodium sulfate and evaporated in vacuo to give the title compound (44 g) as a solid.

[1451] HPLC / MS (method 1): Rt: 2.066 min; m / z=438 (M+1) + .

[1452] Step 4: Synthesis of tert-butyl N-[4-[1,4-dimethyl-5-[[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate

[1453] Under an inert atmosphere, to a stirred solution of N-[5-(4-bromophenyl)-2,4-dimethyl-pyrazole-3-yl]-4-(trifluoromethyl)benzamide (2.5g) in 1,4-dioxane (30mL) was added tert-butyl carbamate (0.802g), palladium (II) acetate (0.128g), 2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl (0.544g) and cesium carbonate (3.717g) at ambient temperature. The reaction mixture was heated at 100 ° C for 16h, and after the reaction was complete, the mixture was dissolved in water. The mixture was extracted with EtOAc, and the organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to silica gel flash column chromatography, eluted with a gradient of EtOAc and heptane to obtain the title compound (2.2g) as a solid.

[1454] HPLC / MS (method 1): Rt: 1.918 min; m / z = 475 (M+1) + .

[1455] Step 5: Synthesis of N-[5-(4-aminophenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide

[1456] To a stirred solution of tert-butyl N-[4-[1,4-dimethyl-5-[[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate (3.4 g) in DCM (50 mL) was added trifluoroacetic acid (5 mL) at ambient temperature. The reaction mixture was heated at 50 ° C for 16 h, and after the reaction was complete, the mixture was neutralized with aqueous sodium bicarbonate solution. The mixture was extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to silica gel flash column chromatography, eluted with a gradient of EtOAc and heptane to obtain the title compound (1.2 g) as a solid.

[1457] HPLC / MS (method 1): Rt: 1.727 min; m / z=375 (M+1) + .

[1458] Step 6: Synthesis of (4-nitrophenyl) N-[4-[1,4-dimethyl-5-[[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate

[1459] To a stirred solution of N-[5-(4-aminophenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide (0.2 g) in THF (4 mL) was added (4-nitrophenyl)chloroformate (0.108 g) under an inert atmosphere at 0° C. The reaction mixture was stirred at ambient temperature for 3 h, and after completion of the reaction, the solvent of the reaction mixture was evaporated in vacuo to afford the title compound (0.2 g) as a solid.

[1460] HPLC / MS (method 1): Rt: 1.885 min; m / z=540 (M+1) + .

[1461] Step 7: Synthesis of N-[5-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide (C-1)

[1462] To a stirred solution of (4-nitrophenyl) N-[4-[1,4-dimethyl-5-[[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate (0.2 g) in acetonitrile (4 mL) was added 2-imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (E1, 0.092 g), N,N,N-diisopropylethylamine (0.072 g) and tripotassium phosphate (0.118 g) at ambient temperature. The reaction mixture was stirred for 19 h at ambient temperature. After completion of the reaction, the mixture was diluted with water and extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to preparative HPLC purification, eluted with a gradient of acetonitrile and water to obtain the title compound (0.17 g) as a solid.

[1463] HPLC / MS (method 1): Rt: 1.960 min; m / z = 649 (M+1) + .

[1464] 1H NMR (300MHz, DMSO-d6) δ10.47(s,1H),9.86(s,1H),8.23(d,J=8.1Hz,2H),7.97(d, J=8.2Hz,2H),7.73(d,J=8.6Hz,2H),7.57(d,J=8.6Hz,2H),7.40(d,J=8.0Hz,1H), 7.32–7.23(m,1H),7.11–7.04(m,1H),4.39–4.08(m,2H),3.69(s,3H),2.67(h,J=6 .8Hz,1H),2.32(s,3H),2.05(s,3H),1.18(d,J=6.8Hz,3H),1.10(d,J=6.8Hz,3H).

[1465] Synthesis of 2-Imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (E1)

[1466] Step 1: Synthesis of 2-chloro-N-(2-isopropyl-5-methyl-phenyl)acetamide

[1467] To a stirred solution of 2-isopropyl-5-methyl-aniline (1.5 g) in THF (100 mL) was added triethylamine (1.221 g) at ambient temperature, and the reaction mixture was cooled to 10 ° C. 2-chloroacetyl chloride was added dropwise to the reaction mass over 30 min and the reaction mixture was stirred at ambient temperature for 16 h. After the reaction was complete, the mixture was diluted in aqueous sodium bicarbonate solution and the reaction mixture was extracted with EtOAc. The organic extract was washed with brine solution, dried over anhydrous sodium sulfate and evaporated in vacuo to give the title compound (1.8 g) as a light yellow oil. HPLC / MS (method 1): Rt: 1.813 min; m / z=223.70 (M-1) + .

[1468] Step 2: Synthesis of 2-imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (E1)

[1469] To a stirred solution of 2-chloro-N-(2-isopropyl-5-methyl-phenyl)acetamide (0.5 g) in acetone (10 mL) was added potassium thiocyanate (0.431 g) at ambient temperature, and the reaction mixture was refluxed for 4 h. After completion of the reaction, the mixture was diluted in aqueous sodium bicarbonate and extracted with EtOAc. The organic extract was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give the title compound (0.42 g) as a solid.

[1470] HPLC / MS (method 1): Rt: 1.675 min; m / z = 249 (M+1)+ .

[1471] Example C-2:

[1472] Preparation of [(Z)-N'-[[4-[1,4-dimethyl-5-[[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamoyl]-N-(2-isopropyl-5-methyl-phenyl)carbamimidoyl]sulfanylmethyl acetate (C-2)

[1473] To a stirred solution of (4-nitrophenyl) N-[4-[1,4-dimethyl-5-[[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate (0.45 g) in THF (9 mL) was added [N-(2-isopropyl-5-methyl-phenyl)carbamimidoyl]sulfanylmethyl acetate hydrobromide (E1 ', 0.234 g) and N,N,N-diisopropylethylamine (0.194 g) at ambient temperature. The reaction mixture was stirred at ambient temperature for 24 h. After completion of the reaction, the mixture was diluted with water and extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to preparative HPLC purification, eluted with a gradient of acetonitrile and water to obtain the title compound (0.18 g) as a solid.

[1474] HPLC / MS (method 1): Rt: 2.205 min; m / z=681 (M+1) + .

[1475] 1 H NMR (500MHz, DMSO-d6) δ11.27(s,1H),10.46(s,1H),9.72(s,1H),8.23(dd,J=8.3,4.3Hz,2H),7.97( dd,J=8.8,2.6Hz,2H),7.73(d,J=8.3Hz,1H),7.62(d,J=8.2Hz,2H),7.45(s,1H),7.29(d,J=8.0Hz,1H ),7.26–7.06(m,1H),7.04(d,J=1.8Hz,1H),5.75(d,J=9.0Hz,1H),5.60(s,1H),3.70(d,J=4.6Hz,3H ), 3.03 (p, J = 6.8Hz, 1H), 2.29 (d, J = 6.3Hz, 3H), 2.06 (d, J = 11.8Hz, 6H), 1.16 (dd, J = 10.8, 6.8Hz, 6H).

[1476] Synthesis of [N-(2-isopropyl-5-methyl-phenyl)carbamimidoyl]sulfanyl methyl acetate hydrobromide (E1')

[1477] Step 1: N-[(2-Isopropyl-5-methyl-phenyl)carbamothioyl]benzamide

[1478] To a stirred solution of 2-isopropyl-5-methyl-aniline (0.4 g) in acetone (5 mL) was added benzoyl isothiocyanate (0.481 g) under an inert atmosphere at 0° C. The reaction mixture was stirred at ambient temperature for 6 h, and after completion of the reaction, the solvent of the reaction mixture was evaporated in vacuo to afford the title compound (0.8 g) as a solid.

[1479] HPLC / MS (method 1): Rt: 2.153 min; m / z=313 (M+1) + .

[1480] Step 2: [(1E)-1-Isobutyl-3-methyl-buta-1,3-dienyl]thiourea

[1481] A stirred solution of N-[(2-isopropyl-5-methyl-phenyl)thiocarbamoyl]benzamide (0.8 g) in 2N sodium hydroxide (10 mL) was heated at 90 ° C for 2 h. After the reaction was complete, the mixture was diluted with water and extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane to give the title compound (0.32 g) as a solid. HPLC / MS (Method 1): Rt: 1.584 min; m / z=209 (M+1) + .

[1482] Step 3: Synthesis of [N-(2-isopropyl-5-methyl-phenyl)carbamimidoyl]sulfanylmethyl acetate hydrobromide (E1')

[1483] To a stirred solution of [(1E)-1-isobutyl-3-methyl-buta-1,3-dienyl]thiourea (0.1 g) in acetone (2 mL) was added bromomethyl acetate (0.081 g) at ambient temperature. The reaction mixture was stirred at ambient temperature for 18 h, and after completion of the reaction, the solvent of the reaction mixture was evaporated in vacuo to give the title compound (0.1 g) as an oil.

[1484] HPLC / MS (method 1): Rt: 1.936 min; m / z = 281 (M+1) + .

[1485] Example C-3:

[1486] Preparation of N-[5-[4-[(2-isopropyl-5-methyl-phenyl)thiocarbamoylaminocarbamoylamino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide (C-3)

[1487] To a stirred solution of [(Z)-N'-[[4-[1,4-dimethyl-5-[[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamoyl]-N-(2-isopropyl-5-methyl-phenyl)carbamimidoyl]sulfanylmethyl acetate (0.325 g) in MeOH (6 mL) was added 7N ammonia in MeOH (2 mL) at ambient temperature. The reaction mixture was stirred at ambient temperature for 18 h. After completion of the reaction, the solvent of the reaction mixture was evaporated in vacuo. The obtained residue was subjected to flash column chromatography on silica gel, eluting with a gradient of EtOAc and heptane to give the title compound (0.085 g) as a solid.

[1488] HPLC / MS (method 1): Rt: 2.173 min; m / z=609 (M+1) + .

[1489] 1 H NMR (500MHz, DMSO-d6) δ11.68(s,1H),10.48(s,1H),10.16(s,1H),9.41(s,1H),8.23(d,J=8.1Hz,2H),7.97(d,J=8.1Hz,2H),7.71–7.65(m,2H) ,7.55–7.50(m,2H),7.28–7.21(m,2H),7.15–7.09(m,1H),3.71(s,3H), 3.01(p,J=6.9Hz,1H),2.29(s,3H),2.07(s,3H),1.18(d,J=6.8Hz,6H).

[1490] Example C-4:

[1491] Preparation of N-[5-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide (C-4)

[1492] Step 1: N-[5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide

[1493] N-[5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide (0.5 g) was dissolved in DMF (12.5 mL) and cesium carbonate (0.74 g) and iodomethane (0.2 g) were added. The reaction mixture was stirred at 50 ° C for 3 h. After the starting material was consumed, the reaction mixture was cooled to room temperature and EtOAc was added. The resulting precipitate was filtered, the solvent was evaporated and purified by column chromatography to give N-[5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide (0.52 g). 1 H NMR (500 MHz, CHLOROFORM-d) δ 7.54–7.48 (m, 4H), 7.46–7.40 (m, 4H), 3.70 (s, 3H), 3.40 (s, 3H), 1.98 (s, 3H).

[1494] Step 2: tert-Butyl N-[4-[1,4-dimethyl-5-[methyl-[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate

[1495] N-[5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide (0.52g) is dissolved in 1,4-dioxane (5mL) and then tert-butyl carbamate (0.20g), cesium carbonate (0.90g), palladium (II) acetate (0.04g) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.14g) are added while nitrogen is purged. The resulting mixture is stirred at 100°C overnight. After the starting material is consumed, the reaction mixture is cooled to room temperature, quenched by adding water (7mL) and the organic phase is extracted twice with EtOAc. The combined organic phases were washed with saturated brine solution, dried over magnesium sulfate and evaporated to give tert-butyl N-[4-[1,4-dimethyl-5-[methyl-[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate (0.52 g).

[1496] 1 H NMR (500 MHz, CHLOROFORM-d) δ 8.05 (m, 2H), 7.82 (m, 2H), 7.57 (m, 2H), 7.46 (m, 2H), 3.75 (s, 3H), 2.12 (s, 3H), 1.68 (s, 3H), 1.59 (s, 9H).

[1497] Step 3: N-[5-(4-aminophenyl)-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide

[1498] Tert-butyl N-[4-[1,4-dimethyl-5-[methyl-[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate (0.52 g) was dissolved in DCM (50 mL) and trifluoroacetic acid (0.25 mL) was added at room temperature. The reaction mixture was stirred for 5 days, and additional trifluoroacetic acid (0.36 mL) was added until all remaining starting material was consumed. The reaction mixture was neutralized by adding saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, evaporated and purified by column chromatography to give N-[5-(4-aminophenyl)-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide (0.2 g). 1 H NMR (500 MHz, chloroform-d) δ 7.54–7.48 (m, 4H), 7.46–7.40 (m, 4H), 3.72 (s, 3H), 3.42 (s, 3H), 1.99 (s, 3H).

[1499] Step 4: N-[5-[4-[[(Z)-[3-(2-Isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide (C-4)

[1500] N-[5-(4-Aminophenyl)-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide (0.1 g) was dissolved in acetonitrile (7 mL) and then cesium carbonate (0.07 g) and 4-nitrophenyl chloroformate (0.05 g) were added. The reaction mixture was stirred at room temperature for 5 h. After TLC indicated that the starting material was consumed, 2-imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (0.07 g) and cesium carbonate (0.08 g) were added. The reaction mixture was stirred at room temperature overnight, the solvent was evaporated, and the residue was purified by column chromatography to give N-[5-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide (0.04 g). 1 H NMR (400 MHz, chloroform-d) δ 7.49–7.34 (m, 10H), 6.92–6.87 (m, 1H), 3.95 (d, J = 3.1 Hz, 2H), 3.67 (s, 3H), 3.39 (s, 3H), 2.66 (m, 1H), 2.37 (s, 3H), 1.97 (s, 3H), 1.18 (m, 6H)

[1501] Example C-5:

[1502] Preparation of N-[5-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide (C-5)

[1503] Step 1: 4-bromobenzimidic acid methyl ester

[1504] To a stirred solution of 4-bromobenzonitrile (10 g) in methanol (100 mL) was added acetyl chloride (43.125 g) at 0°C. The reaction mixture was stirred at ambient temperature for 0.5 h, and after completion of the reaction, the mixture was evaporated. The solid precipitate was filtered and washed with methyl tert-butyl ether and dried in vacuo to give the title compound (10 g) as an off-white solid. HPLC / MS (Method 1): Rt: 0.86 min; m / z=214 (M) + .

[1505] Step 2: (1Z)-4-Bromo-N-cyano-benzimidic acid methyl ester

[1506] To the stirred solution of 4-bromobenzene formimidate HCl salt (3g) in water (50mL) cyanamide (1.374g) and disodium hydrogen phosphate (3.315g) are added at ambient temperature.Reactant mixture is stirred at ambient temperature for 19h, and after the completion of the reaction, the mixture is diluted in water.Mixture is extracted with EtOAc, and organic extract is dried over anhydrous sodium sulfate and evaporated in a vacuum to obtain the title compound (3g) in a light yellow oil. 1 H NMR (300 MHz, CHLOROFORM-d) δ 8.00 (d, J = 8.7 Hz, 2H), 7.68 (d, J = 8.7 Hz, 2H), 4.08 (s, 3H).

[1507] Step 3: 5-(4-bromophenyl)-2-methyl-1,2,4-triazol-3-amine

[1508] To a stirred solution of (1Z)-4-bromo-N-cyano-benzimidic acid methyl ester (5 g) in MeOH (40 mL) and acetic acid (10 mL) was added methylhydrazine (1.287 g, 85% solution) at ambient temperature. The reaction mixture was heated at 85° C. for 16 h, and after completion of the reaction, the reaction mixture was cooled to ambient temperature, the solid precipitate was filtered and washed with MeOH and dried in vacuo to give the title compound (3 g) as an off-white solid. HPLC / MS (Method 1): Rt: 1.25 min; m / z=253 (M) + .

[1509] Step 4: N-[5-(4-bromophenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide

[1510] To a stirred solution of 5-(4-bromophenyl)-2-methyl-1,2,4-triazole-3-amine (1 g) in THF (10 mL) was added triethylamine (0.8 g) and 4-(trifluoromethoxy)benzoyl chloride (0.97 g) at ambient temperature. The reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was dissolved in water and the mixture was extracted with DCM. The organic extract was washed with aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to silica gel flash column chromatography, eluted with a gradient of EtOAc and heptane to give the title compound (1 g) as a solid. HPLC / MS (Method 1): Rt: 2.13 min; m / z=441 (M) + .

[1511] Step 5: Synthesis of tert-butyl N-[4-[1-methyl-5-[[4-(trifluoromethoxy)benzoyl]amino]-1,2,4-triazol-3-yl]phenyl]carbamate

[1512] Under an inert atmosphere, to a stirred solution of N-[5-(4-bromophenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide (6 g) in 1,4-dioxane (60 mL) was added tert-butyl carbamate (2.39 g), tris(dibenzylideneacetone)dipalladium(0) (1.245 g), 5-(di-tert-butylphosphino)-1',3',5'-triphenyl-1'H-[1,4']dipyrazole (0.689 g) and potassium tert-butoxide (4.578 g) at ambient temperature. The reaction mixture was heated at 90° C. for 16 h, and after completion of the reaction, the mixture was dissolved in water. The mixture was extracted with EtOAc, and the organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to flash column chromatography on silica gel, eluting with a gradient of EtOAc and heptane to give the title compound (5.8 g) as a solid. HPLC / MS (Method 1): Rt: 2.12 min; m / z=478 (M+1) + .

[1513] Step 6: N-[5-(4-aminophenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide

[1514] To a stirred solution of tert-butyl N-[4-[1-methyl-5-[[4-(trifluoromethoxy)benzoyl]amino]-1,2,4-triazol-3-yl]phenyl]carbamate (5.8 g) in DCM (80 mL) was added trifluoroacetic acid (5.61 mL) at ambient temperature. The reaction mixture was stirred at ambient temperature for 6 h, and after the reaction was complete, the reaction mixture was quenched with water (100 mL) and neutralized with 10% sodium hydroxide solution. The mixture was extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and evaporated under vacuum to give the title compound (4.1 g) as a solid. HPLC / MS (Method 1): Rt: 1.69 min; m / z=378 (M+1) + .

[1515] Step 7: Synthesis of N-[5-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide (C-5)

[1516] To a stirred solution of N-[5-(4-aminophenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide (0.2 g) in THF (4 mL) was added (4-nitrophenyl)chloroformate (0.112 g) and pyridine (0.168 g) at 0 ° C. The reaction mixture was stirred at ambient temperature for 3 h. After 3 h, 2-imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (E1, 0.132 g) and pyridine (0.168 g) were added. The reaction mixture was stirred at 65 ° C for 3 h. After the reaction was complete, the mixture was diluted with water and extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to preparative HPLC purification, eluted with a gradient of acetonitrile and water to obtain the title compound (0.118 g) as a solid.

[1517] HPLC / MS (method 1): Rt: 5.84 min; m / z = 650 (M-1) + .

[1518] 1H NMR(500MHz,DMSO-d6)δ11.28(s,1H),9.95(s,1H),8.20–8.15(m,2H),7.86(d,J=8.4H z,2H),7.76(d,J=8.5Hz,2H),7.58(d,J=8.3Hz,2H),7.40(d,J=8.0Hz,1H),7.28(d,J=8 .2Hz,1H),7.07(d,J=1.9Hz,1H),4.21(d,J=17.9Hz,1H),4.10(d,J=15Hz,1H),3.74(s ,3H),2.67(p,J=6.9Hz,1H),2.32(s,3H),1.17(d,J=6.8Hz,3H),1.10(d,J=6.8Hz,3H).

[1519] Example C-6:

[1520] Preparation of N-[5-[3-chloro-4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide (C-6)

[1521] Step 1: N-[5-(4-amino-3-chloro-phenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide

[1522] To a stirred solution of N-[5-(4-aminophenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide (1.5 g) in acetonitrile (15 mL) was added N-chlorosuccinimide (0.531 g) at ambient temperature. The reaction mixture was stirred at 70 ° C for 6 h, and after the reaction was complete, the mixture was diluted in water. The mixture was extracted with EtOAc, and the organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to silica gel flash column chromatography, eluted with a gradient of EtOAc and heptane to obtain the title compound (1.25 g) as a yellow solid.

[1523] HPLC / MS (method 1): Rt: 2.02 min; m / z = 412.2 (M+1) + .

[1524] Step 2: N-[5-[3-chloro-4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide (C-6)

[1525] Under an inert atmosphere, to a stirred solution of N-[5-(4-amino-3-chloro-phenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide (1.0 g) in THF (10 mL) was added (4-nitrophenyl)chloroformate (0.587 g) at 0 ° C. The reaction mixture was stirred for 3 h at ambient temperature. Acetonitrile (10 mL) was then added. 2-imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (E1, 0.905 g), N,N,N-diisopropylethylamine (0.628 g) and tripotassium phosphate (0.635 g) were added at 0 ° C. The reaction mixture was stirred for 16 h at 27 ° C. After completion of the reaction, the mixture was diluted in water. The mixture was extracted with EtOAc, and the organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was triturated in MeOH and filtered to give the title compound (1.2 g) as a white solid. HPLC / MS (Method 1): Rt: 2.34 min; m / z = 686.4 (M+1) + . 1 H NMR(500MHz,DMSO-d6)δ11.32(s,1H),9.08(s,1H),8.20–8.13(d,2H),8.01–7.66(m,3H),7.59(d,J=8.3Hz,2H),7 .44–7.19(m,2H),7.06(s,1H),4.28–4.03(m,2H),3.77(s,3H),2.74–2.60(m,1H),2.31(s,3H),1.29–0.96(m,6H).

[1526] Example C-7:

[1527] Preparation of N-[4-cyano-5-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (C-7)

[1528] Step 1: Synthesis of 3,5-dibromo-1H-pyrazole-4-carbonitrile

[1529] To a stirred solution of 1H-pyrazole-4-carbonitrile (10 g) in EtOH (25 mL) and water (35 mL) was added sodium acetate (12.336 g) and bromine (6.86 g) at 10°C. The reaction mixture was stirred at ambient temperature for 2 h. The reaction mixture was dissolved in water and the mixture was extracted with DCM. The organic extract was dried over anhydrous sodium sulfate and evaporated under vacuum to give the title compound (4.9 g). HPLC / MS (Method 1): Rt: 1.73 min; m / z=252 (M+2) + .

[1530] Step 2: Synthesis of 3,5-dibromo-1-methyl-pyrazole-4-carbonitrile

[1531] To a stirred solution of 3,5-dibromo-1H-pyrazole-4-carbonitrile (4.9 g) in DMF (25 mL) was added cesium carbonate (9.545 g) and iodomethane (4.158 g) at ambient temperature. The reaction mixture was stirred at ambient temperature for 17 h. The reaction mixture was dissolved in water, the solid precipitate was filtered and washed with water and dried in vacuo to give the title compound (50 g) as an off-white solid. HPLC / MS (Method 1): Rt: 1.82 min; m / z=266 (M+1) + .

[1532] Step 3: Synthesis of 5-amino-3-bromo-1-methyl-pyrazole-4-carbonitrile

[1533] 2,4-dimethoxybenzylamine (8.83mL) is added to a stirred solution of 3,5-dibromo-1-methyl-pyrazole-4-carbonitrile (7g) in N-methyl-2-pyrrolidone (14mL) at ambient temperature. The reaction mixture is stirred at 140 DEG C for 2h. After the reaction is complete, 5N hydrochloric acid (50mL) is added and the reaction mixture is stirred at ambient temperature for 2h. The reaction mixture is dissolved in water and the mixture is extracted with EtOAc. The organic extract is dried over anhydrous sodium sulfate and evaporated in vacuo. The residue obtained is subjected to silica gel flash column chromatography, eluted with the gradient of EtOAc and heptane to obtain the title compound (5.8g) in a solid.

[1534] HPLC / MS (method 1): Rt: 1.01 min; m / z = 203 (M+2) + .

[1535] Step 4: Synthesis of N-(5-bromo-4-cyano-2-methyl-pyrazol-3-yl)-4-(trifluoromethoxy)benzamide

[1536] To a stirred solution of 5-amino-3-bromo-1-methyl-pyrazole-4-carbonitrile (7g) in DCM (70mL) was added pyridine (14mL) and 4-(trifluoromethoxy)benzoyl chloride (6.7mL) at 0°C. The reaction mixture was stirred for 24h at ambient temperature. The reaction mixture was dissolved in water and the mixture was extracted with DCM. The organic extract was washed with 2.5M hydrochloric acid, dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to silica gel flash column chromatography, eluted with a gradient of EtOAc and heptane to obtain the title compound (2.5g) in a solid state.

[1537] HPLC / MS (method 1): Rt: 2.02 min; m / z = 389 (M) + .

[1538] Step 5: Synthesis of N-[5-(4-aminophenyl)-4-cyano-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide

[1539] Under an inert atmosphere, to a stirred solution of N-(5-bromo-4-cyano-2-methyl-pyrazole-3-yl)-4-(trifluoromethoxy)benzamide (3.2g) in 1,4-dioxane (30mL) and water (3mL) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)aniline (1.98g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.602g) and potassium carbonate (1.70g) at ambient temperature. The reaction mixture was heated at 80°C for 8h, and after the reaction was complete, the mixture was dissolved in water. The mixture was extracted with EtOAc, and the organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to silica gel flash column chromatography, eluted with a gradient of EtOAc and heptane to obtain the title compound (2.05g) as a solid. HPLC / MS (method 1): Rt: 1.93 min; m / z = 402 (M+1) + .

[1540] Step 6: Synthesis of N-[4-cyano-5-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (C-7)

[1541] To a stirred solution of N-[5-(4-aminophenyl)-4-cyano-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (0.2 g) in THF (4 mL) was added bis(2,5-dioxopyrrolidin-1-yl)carbonate (0.134 g) and pyridine (0.157 g) at 0 ° C. The reaction mixture was stirred at ambient temperature for 3 h. After 3 h, 2-imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (E1, 0.124 g) and pyridine (0.157 g) were added. The reaction mixture was stirred at 65 ° C for 3 h. After the reaction was complete, the mixture was diluted with water and extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to silica gel flash column chromatography, eluted with a gradient of EtOAc and heptane to obtain the title compound (0.175 g) as a solid. HPLC / MS (method 1): Rt: 2.523 min; m / z = 675 (M-1) + . 1 H NMR(500MHz,DMSO-d6)δ11.13(s,1H),9.99(s,1H),8.20–8.15(m,2H),7.79(q, J=8.5Hz,4H),7.62(d,J=8.3Hz,2H),7.40(d,J=8.3Hz,1H),7.28(d,J=8.0Hz,1 H),7.07(s,1H),4.20(s,1H),4.09(d,J=18.0Hz,1H),3.80(d,J=2.1Hz,3H),2. 67(p,J=7.3Hz,1H),2.32(s,3H),1.17(d,J=6.9Hz,3H),1.10(d,J=6.9Hz,3H).

[1542] Example C-8:

[1543] Preparation of N-[5-[3-chloro-4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (C-8)

[1544] Step 1: Synthesis of N-[(1-amino-2-methyl-prop-1-enyl)-methyl-amino]formamide

[1545] To a stirred solution of ethyl 2-cyanopropionate (4 g) in 1,4-dioxane (40 mL) was added methylhydrazine 80% solution (1.993 g) at 0 ° C. The reaction mixture was heated at 110 ° C for 17 h, and after the reaction was complete, the mixture was evaporated. The solid precipitate was filtered, washed with heptane and dried to give the title compound (2.9 g) as a solid. HPLC / MS (method 1): Rt: 1.90 min; m / z = 128.3 (M + 1) + .

[1546] Step 2: Synthesis of (5-amino-1,4-dimethyl-pyrazol-3-yl) trifluoromethanesulfonate

[1547] To a stirred solution of 3-amino-2,4-dimethyl-1H-pyrazole-5-one (1.6g) in DMF (20mL) was added 1,1,1-trifluoro-N-phenyl-N-(trifluoromethylsulfonyl)methylsulfonamide (5.39g), N,N,N-diisopropylethylamine (4.87g) at 0°C. The reaction mixture was stirred at ambient temperature for 17h, and after the reaction was complete, the mixture was dissolved in water. The mixture was extracted with EtOAc, and the organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to silica gel flash column chromatography, eluted with a gradient of EtOAc and heptane to obtain the title compound (3.15g) as a solid.

[1548] HPLC / MS (method 1): Rt: 1.90 min; m / z = 260 (M+1) + .

[1549] Step 3: Synthesis of [1,4-dimethyl-5-[[4-(trifluoromethoxy)benzoyl]amino]pyrazol-3-yl] trifluoromethanesulfonate

[1550] Pyridine (9.34 mL) and 4-(trifluoromethoxy)benzoyl chloride (2.85 mL) were added to a stirred solution of (5-amino-1,4-dimethyl-pyrazole-3-yl) trifluoromethanesulfonate (3 g) in DCM (30 mL) at 0 ° C. The reaction mixture was stirred for 24 h at ambient temperature. The reaction mixture was dissolved in water and extracted with DCM. The organic extract was washed with 2.5 M hydrochloric acid, dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to silica gel flash column chromatography, eluted with a gradient of EtOAc and heptane to obtain the title compound (3.15 g) as a white solid.

[1551] HPLC / MS (method 1): Rt: 2.16 min; m / z=448 (M+1) + .

[1552] Step 4: Synthesis of N-[5-(4-amino-3-chloro-phenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide

[1553] Under an inert atmosphere, 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)aniline (0.595g), tetrakis(triphenylphosphine)palladium(0) (0.517g) and potassium carbonate (0.618g) were added to a stirred solution of [1,4-dimethyl-5-[[4-(trifluoromethoxy)benzoyl]amino]pyrazole-3-yl] trifluoromethanesulfonate (1g) in 1,4-dioxane (10mL) at ambient temperature. The reaction mixture was heated at 120°C for 18h, and after the reaction was complete, the mixture was dissolved in water. The mixture was extracted with EtOAc, and the organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The obtained residue was subjected to silica gel flash column chromatography, eluted with a gradient of EtOAc and heptane to obtain the title compound (0.59g) as a solid.

[1554] HPLC / MS (method 1): Rt: 2.24 min; m / z=425 (M+1) + .

[1555] Step 5: Synthesis of N-[5-[3-chloro-4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (C-8)

[1556] To a stirred solution of N-[5-(4-amino-3-chloro-phenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (0.6 g) in THF (12 mL) was added bis(2,5-dioxopyrrolidin-1-yl)carbonate (0.38 g) and pyridine (0.446 g) at 0 ° C. The reaction mixture was stirred for 3 h at ambient temperature. After 3 h, 2-imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (E1, 0.351 g) and pyridine (0.446 g) were added. The reaction mixture was stirred for 3 h at 65 ° C. After the reaction was complete, the mixture was diluted with water and extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue obtained was subjected to flash column chromatography on silica gel eluting with a gradient of EtOAc and heptane to give the title compound as a solid (0.45 g).

[1557] HPLC / MS (method 1): Rt: 2.29 min; m / z = 699 (M) + .

[1558] 1 H NMR(500MHz,DMSO-d6)δ10.41(s,1H),9.10(s,1H),8.31–8.11(m,2H),7.87–7.53(m,5H),7.42(s,1H),7.30(s,1H),7.10(s,1H),4.2 4(d,J=18.0Hz,1H),4.11(d,J=18.0Hz,1H),3.72(s,3H),2.70(s,1H),2.34(s,3H),2.09(s,3H),1.22(s,3H),1.12(d,J=6.9Hz,3H).

[1559] Example C-112:

[1560] Preparation of N-[5-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]-methyl-amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide

[1561] Step 1: Synthesis of N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

[1562] Under inert atmosphere, to the stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)aniline (1.0g) in DMF (10mL) was added iodomethane (0.777g) and potassium carbonate (1.262g) at ambient temperature. The reaction mass was stirred at 50 DEG C for 18h, and the reaction process was monitored by TLC analysis. After the completion of the reaction, the reaction mass was diluted with water (20mL) and then extracted with EtOAc (25mL x 2). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography to obtain the title compound (1.0g) as a solid.

[1563] HPLC / MS (method 1): Rt: 2.09 min; m / z=234.3 (M+1)+;

[1564] 1 H NMR (500MHz, DMSO-d6) δ7.43–7.37(m,2H),6.52–6.46(m,2H),6.04(q,J=4.9Hz,1H),2.68(d,J=5.0Hz,3H),1.25(s,12H).

[1565] Step 2: Synthesis of N-[2,4-dimethyl-5-[4-(methylamino)phenyl]pyrazol-3-yl]-4-(trifluoromethoxy)benzamide

[1566] Under an inert atmosphere, to a stirred solution of [1,4-dimethyl-5-[[4-(trifluoromethoxy)benzoyl]amino]pyrazole-3-yl] trifluoromethanesulfonate (1.2 g) in 1,4-dioxane (12 mL) was added N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)aniline (0.688 g), Tetrakis (0.620 g) and potassium carbonate (0.742 g) at ambient temperature. The reaction mass was stirred at 110 ° C for 18 h, and the reaction progress was monitored by TLC analysis. After the reaction was completed, the reaction mass was diluted with water (30 mL) and then extracted with EtOAc (40 mL x 2). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography to obtain the title compound (1.01 g) as a solid.

[1567] HPLC / MS (method 1): Rt: 1.98 min; m / z=405.3 (M+1)+;

[1568] 1 H NMR (300MHz, DMSO-d6) δ10.29(s,1H),8.15(dd,J=8.7,6.8Hz,2H),7.67–7.54(m,4H),7.41(d,J=8. 3Hz, 2H), 6.59 (d, J = 8.4Hz, 1H), 3.63 (d, J = 6.8Hz, 3H), 2.71 (d, J = 5.0Hz, 3H), 2.00 (d, J = 3.2Hz, 3H).

[1569] Step 3: Synthesis of N-[5-[4-[benzoylthiocarbamoyl(methyl)amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide

[1570] Under an inert atmosphere, to a stirred solution of N-[2,4-dimethyl-5-[4-(methylamino)phenyl]pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (1.01 g) in acetone (15 mL) was added benzoyl isothiocyanate (0.488 g) at ambient temperature. The reaction mass was stirred at 50 ° C for 19 h and the reaction progress was monitored by TLC analysis. After the reaction was completed, the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography to obtain the title compound (1.1 g).

[1571] HPLC / MS (Method 1): Rt: 2.08 min; m / z=568.2 (M+1)+.

[1572] Step 4: Synthesis of N-[5-[4-[thiocarbamoyl(methyl)amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide

[1573] To a stirred solution of N-[5-[4-[benzoylthiocarbamoyl(methyl)amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (1.1 g) in MeOH (11 mL) was added 2N NaOH aqueous solution (13 mL) at ambient temperature. The reaction mass was stirred at 65 ° C for 22 h, and the reaction progress was monitored by TLC analysis. After the reaction was complete, the reaction mass was adjusted to a neutral pH using 2N HCl (5 mL) and then extracted with EtOAc (25 mL x 2). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography to obtain the title compound (0.300 g) as a solid.

[1574] HPLC / MS (method 1): Rt: 1.97 min; m / z=464.2 (M+1)+;

[1575] 1 H NMR(500MHz,DMSO-d6)δ10.38(s,1H),8.20–8.13(m,2H),7.77–7.70(m,2H), 7.67–7.51(m,4H),7.36–7.30(m,2H),3.71(s,3H),3.49(s,3H),2.09(s,3H).

[1576] Step 5: Synthesis of N-[5-[4-[(4,5-dioxothiazol-2-yl)-methyl-amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide

[1577] Under inert atmosphere, to N-[5-[4-[thiocarbamoyl (methyl) amino] phenyl]-2,4-dimethyl-pyrazole-3-yl]-4-(trifluoromethoxy) benzamide (0.1g) in EtOAc (2mL) stirring solution, add oxalyl chloride (0.096g) and triethylamine (0.052g) at ambient temperature. Reaction mass is stirred at ambient temperature for 15min, and the reaction process is monitored by TLC analysis. After the completion of the reaction, reaction mass is diluted with water (10mL) and then extracted with DCM (10mL x 2). The organic extracts merged are dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound (0.120g) in solid.

[1578] HPLC / MS (Method 1): Rt: 2.02 min; m / z=517.2 (M)-.

[1579] Step 6: Synthesis of N-[5-[4-[(2-isopropyl-5-methyl-phenyl)thiocarbamoylcarbamoyl-methyl-amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide

[1580] To a stirred solution of N-[5-[4-[(4,5-dioxothiazol-2-yl)-methyl-amino]phenyl]-2,4-dimethyl-pyrazole-3-yl]-4-(trifluoromethoxy)benzamide (0.140 g) in toluene (2 mL) at ambient temperature, and the reaction mass was stirred at 100 ° C for 25 min. The reaction mass was cooled to ambient temperature and 2-isopropyl-5-methyl-aniline (0.044 g) was added. The reaction mass was stirred at ambient temperature for 2 h, and the reaction progress was monitored by TLC analysis. After the reaction was completed, the solvent was concentrated under reduced pressure and the crude product was purified by flash chromatography to obtain the title compound (0.04 g) as a solid.

[1581] HPLC / MS (Method 1): Rt: 2.39 min; m / z=639.4 (M+1)+.

[1582] Step 7: Synthesis of N-[5-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]-methyl-amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (C-112)

[1583] To a stirred solution of N-[5-[4-[(2-isopropyl-5-methyl-phenyl)thiocarbamoylcarbamoyl-methyl-amino] phenyl]-2,4-dimethyl-pyrazole-3-yl]-4-(trifluoromethoxy)benzamide (0.040g) in EtOH (1mL) was added sodium acetate (0.010g) and methyl bromoacetate (0.014g) at ambient temperature. The reaction mass was stirred at 50°C for 3h and monitored by TLC analysis. After the reaction was complete, the reaction mass was diluted with water (5mL) and then extracted with EtOAc (5mL x 2). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography to obtain the title compound (0.015g) as a solid.

[1584] HPLC / MS (method 1): Rt: 2.22 min; m / z=679.3 (M+1)+;

[1585] 1 H NMR(500MHz, DMSO-d6)δ10.36(s,1H),8.18(d,J=8.3Hz,2H),7.59(d,J=8.4Hz,2H),7.46–7.22(m,3H),7.17–6.72(m,4H),4.2 2(d,J=18.0Hz,1H),4.08(d,J=18.0Hz,1H),3.70(s,3H),3.17(d,J=71.8Hz,4H),2.16(s,3H),2.06(s,3H),1.11–0.69(m,6H).

[1586] All other examples listed in Table C were synthesized similarly to the methods mentioned in the General Procedure or Experimental Procedures mentioned above.

[1587] Table C:

[1588]

[1589]

[1590]

[1591]

[1592]

[1593]

[1594]

[1595]

[1596]

[1597]

[1598]

[1599]

[1600]

[1601]

[1602]

[1603]

[1604] Biological Examples :

[1605] Example B.1: Effect on Yellow Fever Mosquito (Aedes aegypti)

[1606] For evaluation of control against the yellow fever mosquito (Aedes aegypti), the test unit consisted of 96-well microtiter plates containing 200 μl of tap water and 5-15 newly hatched Aedes aegypti larvae per well.

[1607] The active compound or mixture was formulated using a solution containing 75% (v / v) water and 25% (v / v) DMSO. Different concentrations of the formulated compound or mixture were sprayed onto the insect diet at 2.5 μl using a custom-made microatomizer in duplicate.

[1608] For the experimental mixtures in these tests, equal volumes of the two mixing partners were mixed together at the desired concentrations.

[1609] After application, the microtiter plates were incubated at 28°C ± 1°C, 80% ± 5% RH for 2 days. Larval mortality was then assessed visually.

[1610] In this test, compounds C-1, C-2, C-3, C-4, C-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-21, C-22, C-23, C-24, C-25, C-27, C-28, C-29, C-30, C-31, C-32, C-33, C-34 , C-35, C-36, C-37, C-38, C-40, C-42, C-43, C-44, C-45, C-46, C-47, C-48, C-49, C-50, C-51, C-52 , C-53, C-54, C-55, C-56, C-57, C-58, C-59, C-60, C-61, C-63, C-64, C-65, C-66, C-67, C-68, C-69, C-70, C-71, C-72, C-73, C-74, C-75, C-76, C-77, C-78, C-79, C-80, C-81, C-82, C-83, C-84, C-85, C-86, C-87, C-88, C-89, C-90, C-91, C-92, C-93, C-94, C-95, C-96, C-97, C-98, C-99, C-100, C-101 , C-102, C-103, C-104, C-105, C-106, C-107, C-108, C-109, C-111, C-112, C-113, C-114, C-115, C-116, C-118, C-120, C-121, C-122, C-123, C-126, C-127, C-128 and C-130 each showed at least 50% mortality at 800 ppm.

[1611] Example B.2: Action against Orchid thrips (Orchid thrips)

[1612] Adult orchid thrips for bioassays were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound was diluted in a 1:1 mixture of acetone: water (volume ratio) and added to the mixture at a rate of 0.01% v / v. HV.

[1613] Each compound was evaluated for thrips efficacy using the floral dip technique. All petals of individual, intact orchids were dipped into the treatment solution and allowed to dry in a Petri dish. The treated petals were placed in individual resealable plastic containers along with approximately 20 adult thrips. All test sites were maintained under continuous light and a temperature of approximately 28°C for the duration of the assay. After three days, the number of live thrips on each petal was counted. Percent mortality was recorded 72 hours after treatment.

[1614] In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-21, C-22, C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31, C-32, C-33, C-34, C-35, C-36, C-37, C-38, C-39, C-40, C-41, C-42, C-43, C-44, C-45, C-46, C-47, C-48, C-49, C-50, C-51, C-52, C-53, C-54, C-55, C-56, C-57, C-58, C-59, 5. C-26, C-27, C-28, C-30, C-31, C-34, C-35, C-36, C-37, C-38, C-40, C-42, C- 43. C-44, C-45, C-48, C-49, C-55, C-56, C-59, C-60, C-61, C-62, C-63, C-65, C- 66. C-67, C-68, C-71, C-72, C-75, C-76, C-77, C-78, C-79, C-80, C-81, C-83, C -84, C-85, C-86, C-87, C-88, C-90, C-92, C-93, C-94, C-96, C-97, C-98, C-99, C C-100, C-101, C-102, C-103, C-104, C-105, C-106, C-108, C-109, C-110, C-113, C-115, C-116, C-118, C-120, C-121, C-129, and C-130 each showed at least 75% mortality at 300 ppm.

[1615] Example B.3: Action against Boll weevil (Boll weevil)

[1616] For evaluation of control of cotton boll weevils (Hymenoptera: Cotton boll weevil), the test unit consisted of 96-well microtiter plates containing insect diet and 5-10 H. boll weevil eggs.

[1617] Compounds were formulated using a solution containing 75% (v / v) water and 25% (v / v) DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μl using a custom-made microatomizer in duplicate.

[1618] After application, the microtiter plates were incubated for 5 days at approximately 25° C.±1° C. and approximately 75%±5% relative humidity. The mortality of the eggs and larvae was then assessed visually.

[1619] In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31, C-32, C-33 -33, C-34, C-35, C-36, C-37, C-38, C-39, C-40, C-42, C-43, C-44, C-45, C-46, C-47, C-48, C-49, C-50, C -51, C-52, C-53, C-54, C-55, C-56, C-57, C-58, C-59, C-60, C-61, C-62, C-63, C-64, C-65, C-66, C-67, C- 68. C-69, C-70, C-71, C-72, C-73, C-74, C-75, C-76, C-77, C-78, C-79, C-80, C-81, C-82, C-83, C-84, C- 85. C-86, C-87, C-88, C-89, C-90, C-91, C-92, C-93, C-94, C-95, C-96, C-97, C-98, C-99, C-100, C-101, C C-102, C-103, C-104, C-105, C-106, C-107, C-108, C-109, C-110, C-111, C-112, C-113, C-114, C-115, C-116, C-118, C-119, C-120, C-121, C-122, C-126, C-127, C-128, C-129 and C-130 each showed at least 75% mortality at 800 ppm.

[1620] Example B.4: Control of Silverleaf whitefly (Bemisia argentifolii)) (adult)

[1621] The active compound was prepared as a 10,000-ppm solution in 100% cyclohexanone by a Tecan liquid handler and supplied in tubes. This 10,000-ppm solution was serially diluted in 100% cyclohexanone to prepare transition solutions. These were used as stock solutions and final dilutions were made in 50% acetone:50% water (v / v) by Tecan into 5 or 10 ml glass vials. Nonionic surfactant It is contained in a solution at a capacity of 0.01% (v / v).The vial is then inserted into an automatic electrostatic sprayer equipped with an atomizing nozzle for application to plants / insects.

[1622] Cotton plants (one per pot) in the cotyledon stage were sprayed using an automatic electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in a sprayer fume hood and then removed from the sprayer. Each pot was placed in a plastic cup and about 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. A suction device and a non-toxic dextrose agar (100 mg / kg) solution connected to a barrier pipette head were used. The insects were collected using a tube. The head containing the collected insects was then gently inserted into the soil containing the treated plants, allowing the insects to crawl out of the head to reach the leaves and feed. The cups were covered with reusable screen lids. The test plants were maintained in a growth chamber at approximately 25°C and approximately 20%-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24-hour photoperiod) to prevent heat from being trapped in the cups. Mortality was assessed 3 days after treatment compared to untreated control plants.

[1623] In this test, compounds C-6, C-32, C-59, C-60, C-61, C-65, and C-67 each showed at least 75% mortality at 300 ppm compared to untreated controls.

[1624] Example B.5: Action against Tobacco budworm (Heliothis virescens)

[1625] For evaluation of control of tobacco budworm (Heliothis virescens), the test unit consisted of a 96-well microtiter plate containing insect diet and 15-25 Heliothis virescens eggs.

[1626] Compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet in 10 μl using a custom-made microatomizer in duplicate.

[1627] After application, the microtiter plates were incubated at approximately 28° C.±1° C. and approximately 80%±5% relative humidity for 5 days. The mortality of eggs and larvae was then assessed visually.

[1628] In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31, C-32, C-33, C-34, C-35 3. C-34, C-35, C-36, C-37, C-38, C-39, C-40, C-41, C-42, C-43, C-44, C-45, C-46, C-47, C-48, C-49, C-50, C-51, C-52, C-53, C-54, C-55, C-56, C-57, C-58, C-59, C-60, C-61, C-62, C-63, C-64, C-65, C-66, C-67, C- 68. C-69, C-70, C-71, C-72, C-73, C-74, C-75, C-76, C-77, C-78, C-79, C-80, C-81, C-82, C-83, C-84, C-85 , C-86, C-87, C-88, C-89, C-90, C-91, C-92, C-93, C-94, C-95, C-96, C-97, C-98, C-99, C-100, C-101, C-10 2. C-103, C-104, C-105, C-106, C-107, C-108, C-109, C-110, C-111, C-112, C-113, C-114, C-115, C-116, C-117, C-118, C-120, C-121, C-122, C-123, C-126, C-127, C-128, C-129 and C-130 each showed a mortality rate of at least 75% at 800 ppm.

[1629] Example B.6: Effect on Diamond back moth (Plutella xylostella)

[1630] The active compound was dissolved in a 1:1 (v / v) mixture of distilled water and acetone at the desired concentration. A surfactant ( HV). Prepare the test solutions on the day of use.

[1631] Cabbage leaves were dipped into the test solution and air-dried. The treated leaves were placed in a Petri dish lined with moist filter paper and inoculated with ten third-instar larvae. Mortality was recorded 72 hours after treatment. Feeding damage was also recorded using a scale of 0% to 100%.

[1632] In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28 C-28, C-30, C-31, C-34, C-35, C-36, C-39, C-40, C-41, C-42, C-43, C-44, C-45, C-46, C-47, C-48, C-49, C-50, C-51, C-52, C-53, C-54, C-55, C-56 and C-57, respectively, showed at least 75% mortality at 300 ppm.

[1633] Example B.7: Southern armyworm (Spodoptera The role of the second instar larvae of eridania

[1634] The active compound was prepared as a 10,000-ppm solution in 100% cyclohexanone by a Tecan liquid handler and supplied in tubes. This 10,000-ppm solution was serially diluted in 100% cyclohexanone to prepare transition solutions. These were used as stock solutions and final dilutions were made by Tecan in 50% acetone:50% water (v / v) into 10 ml or 20 ml glass vials. Nonionic surfactant It is contained in a solution at a capacity of 0.01% (v / v).The vial is then inserted into an automatic electrostatic sprayer equipped with an atomizing nozzle for application to plants / insects.

[1635] Two lima bean plants (variety: Sieva) were planted in pots and selected for treatment at the first true leaf stage. The test solution was sprayed onto the leaves using an automatic electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in a sprayer fume hood and then removed from the sprayer. Each pot was placed in a perforated plastic bag with a zipper seal. Approximately 10 to 11 armyworm larvae were placed in the bag and the bag was zipped shut. The test plants were kept in a growth chamber at approximately 25°C and approximately 20%-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24-hour photoperiod) to prevent heat from being trapped in the bag. Four days after treatment, mortality and reduced feeding compared to untreated control plants were assessed.

[1636] In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31, C-32, C-33, C-34, C-35 3. C-34, C-35, C-36, C-37, C-38, C-40, C-41, C-42, C-43, C-44, C-45, C-46, C-47, C-48, C-49, C-50, C- 51. C-52, C-53, C-54, C-55, C-56, C-57, C-58, C-59, C-60, C-61, C-62, C-63, C-65, C-66, C-67, C-68, C- 69. C-70, C-71, C-72, C-73, C-74, C-75, C-76, C-77, C-78, C-80, C-81, C-82, C-83, C-84, C-85, C-86, C -87, C-88, C-89, C-90, C-91, C-92, C-93, C-94, C-95, C-96, C-97, C-98, C-99, C-100, C-101, C-102, C-1 C-03, C-104, C-105, C-106, C-107, C-108, C-109, C-110, C-111, C-113, C-115, C-116, C-117, C-118, C-119, C-120, C-121, C-122, C-123, C-125, C-126, C-127, C-128, C-129 and C-130 each showed at least 75% mortality at 300 ppm.

[1637] Example B.8: Effect on Diamond back moth (Plutella xylostella)

[1638] To evaluate the control of diamond back moth (Plutella xylostella), the test apparatus consisted of a 96-well microtiter plate containing an insect diet and 15-25 P. xylostella eggs. Compounds or mixtures were formulated using a solution containing 75% water and 25% DMSO. Different concentrations of the formulated compounds or mixtures were sprayed onto the insect diet in 5 μl using a custom-made microatomizer, repeated twice. For the experimental mixtures in these tests, two mixed compounds of the same volume were mixed together at the desired concentration. After application, the microtiter plates were incubated at 28°C ± 1°C, 80% ± 5% RH for 5 days. Egg and larval mortality was then visually assessed.

[1639] In this test, compounds C-58, C-59, C-60, C-61, C-62, C-63, C-64, C-65, C-66, C-67, C-68, C-69, C-70, C-71, C-72, C-73, C-74, C-75, C-76, C-77, C-78, C-70, C-80, C-81, C-82, C-83, C-84, C-85, C-86, C-87, C-88, C-90, C-91, C-92, C-93, C-94, C-95, C-96, C-97, C-98, C-99, C-100, C-101, C-102, C-103, C-104, C-105, C-106, C-107, C-108, C-109, C-110, C-111, C-112, C-113, C-114, C-115, C-116, C-117, C-118, C-119, C-122, C-123, C-126, C-127, C-128, C-129 and C-130 each showed at least 75% mortality at 800 ppm.

[1640] The beneficial activity of the compounds according to the invention relative to structurally related compounds known from the prior art is demonstrated by the following comparative experiments:

[1641]

[1642]

Claims

1. A compound of formula I in Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-; R 5 is H, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkyl-C1-C6-alkoxy, C1-C6-alkyl-C3-C6-cycloalkyl, phenyl, 5- or 6-membered heteroaryl, -CH2-phenyl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or halogen, wherein these alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen or CN; A is N or CR A ; R A is H, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, halogen, CN or NR 6 R 7 , wherein the alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen or CN; R 2 is H or C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen, CN or C1-C6-alkoxy; B 1 Is N or CR B1 ; B 2 Is N or CR B2 ; B 3 Is N or CR B3 ; B 4 Yes CR B4 ; R B1 , R B2 , R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, wherein these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen; D is part DA or DB, R 3 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN; R 4 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkoxy, -O-(C=O)-C1-C6-alkyl or CN; or B is a 5- or 6-membered carbocyclic group, wherein 1 or 2 CH2 moieties of the carbocyclic group may be replaced by a carbonyl group, O or S, wherein the carbocyclic group is unsubstituted or replaced by R h replace; Ar 1 is phenyl or a 5- or 6-membered heteroaryl group, which is unsubstituted or replaced by R Ar1 Replace, where R Ar1 is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f 、C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、S(=O) m R e , -N=S(=O)-(C1-C6-alkyl)2 or SO2NR b R c replace; R 6 and R 7 are identical or different H, C1-C6-alkyl, C3-C6-cycloalkyl, phenyl, -CH2-phenyl, 5- or 6-membered heteroaryl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl, wherein these alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN, C1-C6-alkyl or C1-C6-alkoxy; Ar 2 is phenyl or a 5- or 6-membered heteroaryl group, which is unsubstituted or replaced by R Ar2 Replace, where R Ar2 is halogen, CN, -SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyloxy-C1-C4-alkyl, wherein these alkyl, alkoxy, alkenyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted by halogen or CN; C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c replace; R a , R b and R c are identical or different H, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, -C(=O)-C1-C6-alkyl, wherein these alkyl, alkenyl and cycloalkyl moieties are unsubstituted or substituted by halogen; R d is H or C1-C6-alkyl; R e is C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl, cycloalkyl parts are unsubstituted or substituted by halogen; m is 0, 1, or 2; R f is halogen, OH, CN, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkyl-C1-C4-alkyl or C3-C6-cycloalkyloxy-C1-C4-alkyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkyloxy moieties are unsubstituted or substituted by halogen; R h is halogen, C1-C6-alkyl or C1-C6-alkoxy; and N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

2. A compound of formula I according to claim 1, wherein D is DB.

3. A compound of formula I according to claim 1, wherein D is a group selected from D5 to D7 parts, which are unsubstituted or substituted by 1 or 2 substituents R h replace 4. A compound of formula I according to claim 1, selected from the compounds of formulae I.1 to I.8, wherein the variables are as defined in claim 1 5. A compound of formula I according to any one of the preceding claims, wherein R 5 is H, C1-C6-alkyl or C1-C6-alkyl-CN; R A is H, CN or C1-C6-alkyl; R 2 is H or C1-C6-alkyl.

6. A compound of formula I according to any one of the preceding claims, wherein B 1 Yes CR B1 , B 2 Yes CR B2 , and B 3 Yes CR B3 .

7. A compound of formula I according to any one of claims 1 to 5, wherein B 1 Yes N, B 2 Yes CR B2 , and B 3 Yes CR B3 .

8. A compound of formula I according to any one of claims 1 to 7, wherein R B1 , R B2 , R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen.

9. A compound of formula I according to any one of claims 1 to claim 8, wherein Ar 1 is phenyl, which is unsubstituted or replaced by R Ar1 replace; R Ar1 is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f 、C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、-N=S(=O)-(C1-C6-alkyl)2、SO2NR b R c or S(=O) m R e replace; R a , R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen; R d is H or C1-C6-alkyl; R e is C1-C6-alkyl or C1-C6-haloalkyl; R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen; m is 0, 1 or 2.

10. A composition comprising a compound of formula I according to any one of claims 1 to 9, an N-oxide or an agriculturally acceptable salt thereof, and another active substance.

11. A method for combating or controlling an invertebrate pest, the method comprising contacting the pest or its food supply, habitat or breeding ground with a pesticidally effective amount of at least one compound according to any one of claims 1 to 9 or a composition according to claim 10.

12. A method for protecting growing plants from attack or infestation by invertebrate pests, the method comprising contacting the plants or the soil or water in which the plants are growing with a pesticidally effective amount of at least one compound according to any one of claims 1 to 9 or a composition according to claim 10.

13. A seed comprising the compound according to any one of claims 1 to 9 or an enantiomer, diastereomer or salt thereof, or the composition according to claim 10, in an amount of 0.1 g to 10 kg per 100 kg of seeds.

14. Use of a compound of formula I according to any one of claims 1 to 9 and its agriculturally acceptable salts or a composition according to claim 10 for protecting growing plants from attack or infestation by invertebrate pests.

15. A method for treating or protecting an animal from infestation or infection by invertebrate pests, which method comprises contacting the animal with a pesticidally effective amount of at least one compound of formula I according to any one of claims 1 to 9, its stereoisomers and / or at least one veterinarily acceptable salt thereof.

Images