Azoles are pesticidal compounds

Abstract

The present invention relates to compounds of formula (I), their N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts, where the variables are defined in the specification. The compounds of formula (I), their N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts are useful for the control or prevention of invertebrate pests, particularly arthropod pests and nematodes. The present invention also relates to methods for controlling invertebrate pests using these compounds, and to plant propagation materials, and agricultural and veterinary compositions containing the compounds. [Formula 1] TIFF2025531246000075.tif17170

Description

[Technical Field]

[0001] Invertebrate pests, particularly insects, arachnids, and nematodes, damage growing and harvested crops and infest wooden residential and commercial structures, causing significant economic losses to the food supply and property. Accordingly, there is a continuing need for new agents to control invertebrate pests. [Background technology]

[0002] For example, in WO 2016 / 156076, carbamoylated and thiocarbamoylated oxime derivatives are known for pesticidal use, in WO 2016 / 116445, semicarbazone and thiosemicarbazone derivatives are known for pesticidal use, and in WO 2021 / 013561, pyrazolo pesticidal compounds are known for pesticidal use. Summary of the Invention [Problem to be solved by the invention]

[0003] Due to the ability of target pests to develop resistance to pesticidal agents, there is a continuing need to identify additional compounds suitable for controlling invertebrate pests, such as insects, arachnids, and nematodes. Additionally, there is a need for new compounds that have high pesticidal activity and exhibit a broad spectrum of activity against many different invertebrate pests, especially those insects, arachnids, and nematodes that are difficult to control.

[0004] It is therefore an object of the present invention to identify and provide compounds that exhibit high pesticidal activity against invertebrate pests and have a broad spectrum of activity. [Means for solving the problem]

[0005] It has been found that these objects can be achieved by substituted bicyclic compounds of formula I as shown and defined below, including their stereoisomers, their salts, particularly their agriculturally or veterinarily acceptable salts, their tautomers and their N-oxides. DETAILED DESCRIPTION OF THE INVENTION

[0006] In a first aspect, the present invention provides a compound of formula I [ka] [In the formula, 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 hetaryl, -CH2-phenyl, -CH2-5- or 6-membered hetaryl, 1,3-dioxolan-2-ylmethyl, or halogen, wherein the alkyl, cycloalkyl, phenyl, and hetaryl moieties are unsubstituted or substituted with halogen or CN; A is N or CR A and; 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 with halogen or CN; R 2 is H or C1-C6 alkyl, or C3-C6 cycloalkyl, wherein the alkyl and cycloalkyl portions are unsubstituted or substituted with halogen, CN, or C1-C6 alkoxy; B 1 is N or CR B1 and; B 2 is N or CR B2and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; D is the part DA or DB [ka] and R 3 is H, C1-C6 alkyl, or C3-C6 cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN; R 4 is H, C1-C6 alkyl, or C3-C6 cycloalkyl, wherein the alkyl and cycloalkyl portions are unsubstituted or substituted with 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, one or two CH moieties of which may be replaced by a carbonyl group, O, or S, and the carbocyclic group may be unsubstituted or h is replaced by; Ar 1 is phenyl or 5- or 6-membered heteroaryl, unsubstituted or Ar1 where: R Ar1is halogen, SF, NO, OH, CN, C-C alkyl, C-C alkoxy, C-C cycloalkyl, C-C heterocyclyl, C-C cycloalkoxy, C-C alkenyl, C-C alkynyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C-C heterocyclyl, and cycloalkoxy moieties are unsubstituted or f , C(=O)-OR a , N.R. 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 is replaced by; R 6 and R 7 are the same or different and are 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 the alkyl, cycloalkyl, phenyl, and heteroaryl moieties are unsubstituted or substituted with halogen, CN, C1-C6 alkyl, or C1-C6 alkoxy; Ar 2 is phenyl or 5- or 6-membered heteroaryl, unsubstituted or Ar2 where: 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 cycloalkoxy, C3-C6 cycloalkyl-C1-C4 alkyl, C3-C6 cycloalkoxy-C1-C4 alkyl, and the alkyl, alkoxy, alkenyl, cycloalkyl, and cycloalkoxy moieties are unsubstituted or halogen or CN; C(=O)-OR a , N.R. b R c , C1-C6 alkylene-CN, C(=O)-NR b R c is replaced by; R a , R b and R c are the same or different and are H, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, -C(=O)-C1-C6 alkyl, wherein the alkyl, alkenyl and cycloalkyl moieties are unsubstituted or substituted with halogen; R d is H or C1-C6 alkyl; R e is C1-C6 alkyl or C3-C6 cycloalkyl, and the alkyl and cycloalkyl moieties are unsubstituted or substituted with 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 cycloalkoxy, C3-C6 cycloalkyl-C1-C4 alkyl, or C3-C6 cycloalkoxy-C1-C4 alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and cycloalkoxy moieties are unsubstituted or substituted with halogen; R his halogen, C1-C6 alkyl, or C1-C6 alkoxy] and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

[0007] Furthermore, the present invention also relates to processes and intermediates for preparing the compounds of formula I, as well as to combinations of active compounds comprising them. Furthermore, the present invention relates to agricultural or veterinary compositions comprising the compounds of formula I, and to the use of the compounds of formula I or compositions comprising them for combating or controlling invertebrate pests and / or protecting crops, plants, plant propagation material and / or plants in cultivation from infestation and / or infestation by invertebrate pests. The present invention also relates to methods of applying the compounds of formula I. The present invention also relates to a method for protecting crops, plants, plant propagation material and / or plants in cultivation from infestation or infestation by invertebrate pests, which comprises contacting or treating crops, plants, plant propagation material and plants in cultivation, or the soil, material, surface, space, area or water in which crops, plants, plant propagation material or plants are stored or grown, with a pesticidally effective amount of at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I).

[0008] The present invention further relates to seeds comprising a compound of formula I. Compounds of formula I include N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

[0009] By modifying the starting compounds, compounds of formula I can be prepared by procedures as shown in the schemes below.

[0010] Compounds of formula (I) can be prepared by organic chemistry methods, such as those described in Schemes 1-24 of the synthetic descriptions of the Examples herein below. In Schemes 1-24, the group Ar 1 , A, B 1 , B 2 , B 3 , B 4 , D, Q, X, RA , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R h , and Ar 2 is as defined above for formula (I) unless otherwise specified. [ka]

[0011] R 4 Compounds of formula (I) where is not H are compounds of formula (Ia) and can be prepared by the methods described in WO 2021 / 011722 or analogously to the methods described in Scheme 1: [ka]

[0012] 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 prepared from an amine of formula (Ia-1) as described in March's Advanced Organic Chemistry 6 th It can be generated in situ by using one of the common reagents such as phosgene, diphosgene, triphosgene, or carbonyldiimidazole in the presence of a base in a mixed solvent system (Step I), as described in the "Comparative Example 1: The Art of Iodine-Based Synthesis," edition, Michael B. Smith and Jerry March.

[0013] According to another embodiment of Scheme 1, the isocyanate compound of Formula (Ia-2) is produced by Curtius rearrangement of the acyl azide (Ia-4), for example, in a manner similar to that described in WO 2014 / 204622. The acyl azide of Formula (Ia-4) can be prepared from the corresponding carboxylic acid precursor of Formula (Ia-3) by treatment with ethyl chloroformate and sodium azide in the presence of an amine base such as triethylamine, or by treatment with diphenylphosphoryl azide in the presence of an amine base such as triethylamine.

[0014] Compounds of formula (I) are compounds of formula (Ia) and can also be prepared by the methods described in WO 2021 / 011722 or analogously to the methods described in Scheme 2: [ka]

[0015] According to the method described in Scheme 2, an 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 can then be reacted with a compound of formula (E1) in the presence of an organic base such as DIPEA to form a compound of formula (Ia). Compounds of formula (E1) can be prepared similarly to the methods described in WO 2021 / 011722.

[0016] Scheme 3: [ka] As shown 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 activated carbamate intermediates (E1-1), which are then reacted with amines of formula (Ia-1) in the presence of an organic base such as cesium carbonate or potassium carbonate to form compounds of formula (Ia).

[0017] R 4 Compounds of formula (I) where is H are compounds of formula (Ia') and can be prepared analogously to the methods described in WO 2021 / 011722 or as described in Scheme 4: [ka]

[0018] As shown 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 the presence of an inorganic base such as cesium carbonate in an aprotic solvent. Compounds of formula (E2) can be prepared similarly to the method described in WO 2021 / 011722.

[0019] Compounds of formula (E1-I), (E1-II), (E1-III) and (E1-IV) can be prepared by the method described in J. Med. Chem. 2010, 53(10), 4198-4211 or by the method described in Scheme 5: [ka]

[0020] In the above reaction, the compound of formula (E1-Ia) can be converted into various cyclized analogs of formulas (E1-I), (E1-II), (E1-III), and (E1-IV). The compounds of formulas (E1-I) and (E1-II) can be prepared by treating the compound of formula (E1-Ia) with unsubstituted or mono- or di-substituted 2-chloroacetyl chloride and 3-chloropropanoyl chloride in two steps, as described in J.Med.Chem.2010,53(10),4198-4211. The compounds of formulas (E1-IIIa) and (E1-IVa) can be prepared by treating the compound of formula (E1-Ia) with unsubstituted or mono- or di-substituted 2-chloroacetaldehyde and 3-chloropropanal in two steps, as described 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 the presence of an inorganic base such as cesium carbonate in an aprotic solvent such as acetone.

[0021] Compounds of formula (Ia-I), (Ia-II), (Ia-III) and (Ia-IV) can be prepared from compounds of formula (Ia') by the methods described in WO 2021 / 011722 or analogously to the methods described in Scheme 6: [ka]

[0022] Compounds of formula (Ia', Scheme 6) can be converted to various cyclized analogs of formulas (Ia-I), (Ia-II), (Ia-III), and (Ia-IV). Compounds of formula (Ia') can be treated with an α-haloester, such as methyl bromoacetate or methyl bromopropanoate, to give either unsubstituted or R h Cyclization can be achieved by forming compounds of formula (Ia-I) and (Ia-II) mono- or disubstituted with.

[0023] Unsubstituted or Rh Compounds of formula (Ia-III) and (Ia-IV) mono- or disubstituted with can be prepared by treating a compound of formula (Ia') with a vicinal dihalide. In steps XVIII and XIX, sodium acetate is preferably used in a protic solvent such as ethanol at a temperature ranging from about 20°C to about 70°C. In 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 ranging from about 0°C to about 80°C. All of the above reactions can be carried out similarly to the methods described in WO 2021 / 011722.

[0024] Compounds of formula (Ia-1) can be prepared analogously to the method described in Scheme 7: [ka]

[0025] Compounds of formula (Ia-1) can be prepared by different synthetic routes, as shown in Scheme 7. Step XXII can be carried out by a Suzuki cross-coupling reaction starting from an appropriate arylboronic acid precursor (1), as described either in Tetrahedron, 2009, 65(37), 7817-7824 or in WO 2018 / 075937.

[0026] Alternatively, compounds of formula (Ia-1) can be prepared by reduction of nitro compounds of formula (IIIa-1) using a reducing agent such as SnCl2 in an acid medium, as shown in Step XXIII.

[0027] Alternatively, the compound of formula (Ia-1) can be prepared by reacting the compound of formula (IVa-1) with ammonia in the presence of a metal catalyst or its salt, preferably copper or its salt, as described in Chem. Commun., 2009, 3035-3037.

[0028] Additionally, compounds of formula (Ia-1) can also be prepared in two steps from compounds of formula (IVa-1). Compounds of formula (IVa-1) are treated with tert-butyl carbamate in the presence of a metal catalyst or its salt, preferably palladium or its salt, to form compounds of formula (IVa-2) in step XXV, followed by deprotection of the Boc group using trifluoroacetic acid or dilute hydrochloric acid to form the desired compounds in step XXVI. All of these reactions are described in detail in March's Advanced Organic Chemistry 6. th edition, Michael B. Smith and Jerry March.

[0029] Compounds of formula (IIIa-1) can be prepared analogously to the method described in Scheme 8: [ka]

[0030] Step XXVII can be carried out by Suzuki cross-coupling reaction starting from arylboronic acid precursor (3), as described in Tetrahedron, 2009, 65(37), 7817-7824 or WO 2018 / 075937.

[0031] Compounds of formula (IVa-1) can be prepared analogously to the method described in Scheme 9: [ka]

[0032] Step XXVIII can be carried out by Suzuki cross-coupling starting from arylboronic acid precursor (4), as described in Tetrahedron, 2009, 65(37), 7817-7824 or WO 2018 / 075937.

[0033] Q is -C(=O)-N(R 5)-, and A is N or CR A and R 5 Compounds of formula (IVa-1) in which is H are compounds of formula (IVa-1-1) and can be prepared analogously to the method described in Scheme 10: [ka]

[0034] The compound of formula (IVa-1-1) can be prepared from the compound of formula (IVa-1-1a) in six steps. Step XXIX involves brominating the compound of formula (IVa-1-1a) by reacting it with bromine in the presence of a weak base such as sodium acetate, a protic solvent such as ethanol and water. Step XXX is described in March's Advanced Organic Chemistry 6 th This step involves alkylation by reaction with a corresponding commercially available alkyl halide, preferably iodide or bromide, in the presence of a base such as cesium carbonate and a polar aprotic solvent such as DMF, similar to that described in the "Essays on the Benzylboronic Acids of the Invention" edition by Michael B. Smith and Jerry March. Step XXXI involves the introduction of a protecting group such as 2,4-dimethoxybenzylamine. Step XXXII can be carried out by a Suzuki cross-coupling reaction starting from an arylboronic acid precursor (4), as described in WO 2018 / 075937. Step XXXIII involves deprotecting the compound of formula (IVa-1-1e) by reacting it with 5N hydrochloric acid. Step XXXIV involves the conversion of the compound of formula (IVa-1-1f) to Ar in the presence of a suitable coupling reagent such as HATU and a base such as DIPEA. 1 -COOH to form an amide. All of these steps are based on the methodology outlined in March's Advanced Organic Chemistry 6 thThe compound of formula (IVa-1-1) can be prepared as described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March. th Alternatively, compounds of formula (IVa-1-1f) can be synthesized by treating the compound of formula (IVa-1-1f) with commercially available benzoyl chloride in the presence of a base, as described in Michael B. Smith and Jerry March, Advanced Organic Chemistry, Vol. 6, No. 1, pp. 117-120, 2002. Alternatively, compounds of formula (IVa-1-1) can be synthesized by in situ generation of benzoyl chloride from the corresponding benzoic acid with POCl or SOCl, followed by subsequent synthesis of the compound of formula (IVa-1-1f) with benzoyl chloride, as described in Michael B. Smith and Jerry March, Advanced Organic Chemistry, Vol. 6, No. 1, pp. 117-120, 2002. th The compound (IVa-1-1f) can also be synthesized by treating the compound with a compound of formula (IVa-1-1f) in the presence of a base, as described in the "Comparative Example 1: The Synthesis of N-N-Cyclohexylamine" by Michael B. Smith and Jerry March, Vol.

[0035] Q is -C(=O)-N(R 5 )- and A is CR A and R A is H or C1-C6 alkyl or C3-C6 cycloalkyl or CN or C1-C6 alkoxy, and R 5 Compounds of formula (IVa-1) in which is H are compounds of formula (IVa-1-1A) and can be prepared analogously to the method described in Scheme 11: [ka]

[0036] The compound of formula (IVa-1-1A) can be prepared by the reaction of R 2 The common intermediate of formula (IVa-1-1A) can be prepared from the commercially available benzoylacetonitrile derivative (IVa-1-1g) by reacting the compound of formula (IVa-1-1h) with Ar in the presence of a suitable coupling reagent such as HATU and a base such as DIPEA. 1The compound of formula (IVa-1-1A) can be prepared by reacting with —COOH to form an amide. th Alternatively, compounds of formula (IVa-1-1A) can be synthesized by treating the compound of formula (IVa-1-1h) with commercially available benzoyl chloride in the presence of a base, as described in the "Advanced Organic Chemistry" series, vol. 6, by Michael B. Smith and Jerry March. Alternatively, compounds of formula (IVa-1-1A) can be synthesized by in situ generation of benzoyl chloride from the corresponding benzoic acid with POCl or SOCl, followed by subsequent synthesis of the compound of formula (IVa-1-1h) with benzoyl chloride, as described in the "Advanced Organic Chemistry" series, vol. 6, by Michael B. Smith and Jerry March. th The compound (IVa-1-1h) can also be synthesized by treating the compound with a compound of formula (IVa-1-1h) in the presence of a base, as described in the "Comparative Example 1: The Synthesis of N-N-Cyclohexylamine" by Michael B. Smith and Jerry March, Vol.

[0037] Q is -C(=O)-N(R 5 )-, A is N, and R 5 Compounds of formula (IVa-1) in which is H are compounds of formula (IVa-1-1B) and can also be prepared analogously to the method described in Scheme 12: [ka]

[0038] The compound of formula (IVa-1-1B) can be prepared in four steps from commercially available benzonitrile (5). 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 U.S. Patent Application Publication No. 2007 / 0078141. Step XXXIX involves reacting the compound of formula (IVa-1-1j) with R in a polar protic solvent such as methanol. 2The common intermediate of formula (IVa-1-1B) can be prepared by coupling a compound of formula (IVa-1-1k) with Ar in the presence of a suitable coupling reagent such as HATU and a base such as DIPEA to form a triazole ring. 1 The compound of formula (IVa-1-1B) can be prepared by reacting with —COOH to form an amide. th Alternatively, compounds of formula (IVa-1-1B) can be synthesized by treating the compound of formula (IVa-1-1k) with commercially available benzoyl chloride in the presence of a base, as described in Michael B. Smith and Jerry March, Advanced Organic Chemistry, Vol. 6, No. 1, pp. 117-120, 2002. Alternatively, compounds of formula (IVa-1-1B) can be synthesized by in situ generation of benzoyl chloride from the corresponding benzoic acid with POCl or SOCl, followed by subsequent synthesis of the compound of formula (IVa-1-1k) with benzoyl chloride, as described in Michael B. Smith and Jerry March, Advanced Organic Chemistry, Vol. 6, No. 1, pp. 117-120, 2002. th The compound (IVa-1-1k) can also be synthesized by treating it with a compound of formula (IVa-1-1k) in the presence of a base, as described in the "Comparative Example 1: The Synthesis of Compounds of Formula (IVa-1-1k)" ... edition, Michael B. Smith and Jerry March.

[0039] Q is -N(R 5 )-C(=O)-, and A is CR A and R A is H or C1-C6 alkyl or C3-C6 cycloalkyl or CN or C1-C6 alkoxy, and R 5 Compounds of formula (IVa-1), in which is H, are compounds of formula (IVa-1-2), which can be prepared analogously to the method described in Scheme 13: [ka]

[0040] 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 or NaOH, as mentioned in WO 2011 / 050245. The common intermediate of formula (IVa-1-2) can be prepared by coupling the compound of formula (IVa-1-2c) with Ar in the presence of a suitable coupling reagent, such as HATU, and a base, such as DIPEA. 1 It can be prepared by reaction with -NH2 to form an amide.

[0041] A is CR A or N, and Q is -N(R 4 )-C(=O)-, and R 5 Compounds of formula (IVa-1), in which is H, are compounds of formula (IVa-1-3), which can be prepared analogously to the method described in Scheme 14: [ka]

[0042] Compounds of formula (IVa-1-3) can be prepared in three steps from compounds of formula (IVa-1-3a): Step XLIV involves halogenation, and Step XLV involves the reaction of compounds of formula (IVa-1-3b) with Ar in the presence of a suitable coupling reagent such as HATU and a base such as DIPEA. 1 Step XLVI involves reacting the compound of formula (IIa-4) with —NH to form an amide, and Step XLVI involves Suzuki cross-coupling the compound of formula (IIa-4) with a 4-halo-phenylboronic acid derivative. All of these steps are described in March's Advanced Organic Chemistry 6 th This can be done as described in the "Synthetic Methods for Detecting Irregular and Maximum Size Differences" edition, Michael B. Smith and Jerry March.

[0043] Q is -C(=O)-N(R 5 )- and A is CR A and R A is Cl and R 5 Compounds of formula (IVa-1), in which is H, are compounds of formula (IVa-1-4), which can be prepared analogously to the method described in Scheme 15: [ka]

[0044] Compounds of formula (IVa-1-4) can be prepared in two steps from compounds of formula (IVa-1-1h). Step XLVII involves chlorination using N-chlorosuccinimide in a polar aprotic solvent such as ACN, as described in WO 2014 / 078325. Step XLVIII involves chlorination using N-chlorosuccinimide in a polar aprotic solvent such as ACN, as described in March's Advanced Organic Chemistry 6 th This includes amide coupling reactions such as those described in the "Comparative Chemistry of Electron Microscopy" series, vol. 1, No. 1, pp. 111-118, by Michael B. Smith and Jerry March.

[0045] Q is -C(=O)-N(R 5 )- and R A NR 6 R 7 and R 5 Compounds of formula (IVa-1) where is H are compounds of formula (IVa-1-5) and can be prepared analogously to the method described in Scheme 16: [ka]

[0046] Compounds of formula (IVa-1-5) can be prepared in one step from compounds of formula (IVa-1-4). Compounds of formula (IVa-1-4) (wherein R7 or R 6 is C1-C6 alkyl or C3-C6 cycloalkyl-CH2-phenyl or -CH2-5- or 6-membered hetaryl or 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl), to give compounds of formula (IVa-1-5). 7 or R 6 Compounds of formula (IVa-1-5), in which R is a phenyl or 5- or 6-membered hetaryl ring, can be prepared from compounds of formula (IVa-1-4) by metal-catalyzed reaction with the corresponding aryl halide or 5- or 6-membered hetaryl halide, preferably iodide or bromide, as described in Chinese J. Chem. 2012, 30(10), 2356-2362. 7 and R 6 The compound of formula (IVa-1-5) in which is H can be prepared from the compound of formula (IVa-1-4) by 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.

[0047] Q is -N(R 4 )-C(=O)-, and R A is Cl and R 5 Compounds of formula (IVa-1) where is H are compounds of formula (IVa-1-6) and can be prepared analogously to the method described in Scheme 17: [ka]

[0048] The compound of formula (IVa-1-6) can be prepared from the compound of formula (IVa-1-2b) in three steps. Step L involves chlorination using SOCl2 as described in Youji Huaxue, 2010, 30(11), 1726-1731. Step LI involves hydrolysis with a suitable base such as LiOH or NaOH as mentioned in WO 2011 / 050245. Step LII involves the reaction of the compound of formula (IVa-1-6b) with Ar in the presence of a suitable coupling reagent such as HATU and a base such as DIPEA. 1 -NH2 to form an amide.

[0049] Q is -C(=O)-N(R 5 )- and A is CR A X is Br and R 5 Compounds of formula (IIa) where is H are compounds of formula (IIa-1) and can be prepared analogously to the method described in Scheme 18: [ka]

[0050] 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 it with 5N hydrochloric acid or TFA in 1,4-dioxane. Step LIV involves reacting the compound of formula (IIa-1-1a) with Ar in the presence of a suitable coupling reagent such as HATU and a base such as DIPEA. 1The synthesis of compounds of formula (IIa-1) involves reacting the compound of formula (IIa-1-1a) with -COOH to form an amide. Compounds of formula (IIa-1) can also be synthesized by treating compounds of formula (IIa-1-1a) with commercially available benzoyl chloride in the presence of a base. Alternatively, compounds of formula (IIa-1) can be synthesized by generating benzoyl chloride in situ from the corresponding benzoic acid with POCl or SOCl, followed by subsequent treatment with compounds of formula (IIa-1-1a) in the presence of a base. All of these steps are described in detail in March's Advanced Organic Chemistry 6. th This can be done as described in the "Synthetic Methods for Detecting Irregular and Maximum Size Differences" edition, Michael B. Smith and Jerry March.

[0051] Alternatively, the compound of formula (IIa-1) can be prepared in three steps from commercially available substituted ethyl cyanoacetate (6) via a common intermediate (IIa-1-1a). The compound of formula (IIa-1-1a) can be prepared from the compound of formula (6) by the method described in WO 2014 / 78323.

[0052] Q is -C(=O)-N(R 5 )- and A is CR A , X is OTf, and R 5 Compounds of formula (IIa) where is H are compounds of formula (IIa-2) and can be prepared analogously to the method described in Scheme 19: [ka]

[0053] Compounds of formula (IIa-2) can be prepared from common intermediate (IIa-1-1b) similarly to the method described in WO 2014 / 78323.

[0054] Q is -C(=O)-N(R 5 )-, A is N, and R 5Compounds of formula (IIa) where is H are compounds of formula (IIa-3) and can be prepared analogously to the method described in Scheme 20: [ka]

[0055] The compound of formula (IIa-3) can be prepared in two steps from the compound of formula (IVa-1-1d). Step LX involves deprotecting the compound of formula (IVa-1-1d) by reacting it with 5N hydrochloric acid or TFA in 1,4-dioxane. Step LXI involves reacting the compound of formula (IIa-3-1a) with Ar in the presence of a suitable coupling reagent such as HATU and a base such as DIPEA. 1 The synthesis of compounds of formula (IIa-3) involves reacting a compound of formula (IIa-3-1a) with -COOH to form an amide. Compounds of formula (IIa-3) can also be synthesized by treating a compound of formula (IIa-3-1a) with commercially available benzoyl chloride in the presence of a base. Alternatively, compounds of formula (IIa-3) can be synthesized by generating benzoyl chloride in situ from the corresponding benzoic acid with POCl or SOCl, followed by subsequent treatment with a compound of formula (IIa-3-1a) in the presence of a base. All of these steps are described in March's Advanced Organic Chemistry 6 th This can be done as described in the "Synthetic Methods for Detecting Irregular and Maximum Size Differences" edition, Michael B. Smith and Jerry March.

[0056] Q is -N(R 5 )-C(=O)-, and A is CR A , X is OTf, and R 5 Compounds of formula (IIa) where is H are compounds of formula (IIa-5) in the same manner as described in Scheme 21: [ka]

[0057] The compound of formula (IIa-5) can be prepared in five steps from commercially available substituted diethylpropanedioate (7). Step LXII can be carried out as described in Org. Lett., 2014, 16(23), 6120-6123. The compound of formula (IIa-5-1b) can be prepared from the compound of formula (IIa-5-1a) similarly to the method described in U.S. Patent Application Publication No. 2019 / 0127358. Step LXIV can be carried out as described in WO 2018 / 125961. The last two steps are hydrolysis with a suitable base such as LiOH or NaOH, followed by the reaction of the compound of formula (IIa-5-1d) with Ar in the presence of a suitable coupling reagent such as HATU and a base such as DIPEA, as mentioned in WO 2011 / 050245. 1 -NH2 to form an amide.

[0058] Q is -C(=O)-N(R 5 )- and R 5 Compounds of formula (Ia-1), in which is C1-C6 alkyl or C3-C6 cycloalkyl or -CH2-phenyl or -CH2-5- or 6-membered hetaryl or 1,3-dioxolan-2-ylmethyl or phenyl or 5- or 6-membered hetaryl, are compounds of formula (Ia-1-1) and can be prepared analogously to the method described in Scheme 22: [ka]

[0059] The compound of formula (Ia-1-1) is prepared by the method described in March's Advanced Organic Chemistry 6 thedition, Michael B. Smith and Jerry March, by reaction with the corresponding commercially available alkyl or benzyl halides, preferably iodides or bromides, in the presence of a base such as cesium carbonate and a polar aprotic solvent such as DMF, R can be obtained as C1-C6 alkyl or C3-C6 cycloalkyl or -CH2-phenyl or -CH2-5- or 6-membered hetaryl or 1,3-dioxolan-2-ylmethyl. 5 It can be prepared from a compound of formula (Ia-1-1a) comprising R 5 Compounds of formula (Ia-1-1), in which R is a phenyl or 5- or 6-membered hetaryl ring, can be prepared from compounds of formula (Ia-1-1a) by a metal-catalyzed reaction with the corresponding aryl halide or 5- or 6-membered hetaryl halide, preferably an iodide or bromide, as described in Chinese J. Chem. 2012, 30(10), 2356-2362. Alternatively, compounds of formula (Ia-1-1) can be prepared in two steps from compounds of formula (IIIa-1-1a). Step LXVIII can be carried out similarly to Step LXVII, and Step LXIX involves reduction using a reducing agent such as SnCl in ethanol or Fe with NH4Cl in a mixture of ethanol, THF, and water.

[0060] Q is -N(R 5 )-C(=O)-, and R 5 Compounds of formula (Ia-1), in which is C1-C6 alkyl or C3-C6 cycloalkyl or -CH2-phenyl or -CH2-5- or 6-membered hetaryl or 1,3-dioxolan-2-ylmethyl or phenyl or 5- or 6-membered hetaryl, are compounds of formula (Ia-1-2), which can be prepared analogously to the method described in Scheme 23: [ka]

[0061] 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.

[0062] B 2 or B 3 Compounds of formula (Ia-1) in which is Hal are compounds of formula (Ia-1-3) and can be prepared analogously to the method described in Scheme 24: [ka]

[0063] The compound of formula (Ia-1-3) is prepared by the method described in March's Advanced Organic Chemistry 6 th The halogenated compounds of formula (Ia-1-3a) can be prepared by treating the 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 that described in the above edition of Michael B. Smith and Jerry March.

[0064] Individual compounds of formula I can also be prepared by derivatizing other compounds of formula I or their intermediates.

[0065] If a mixture of isomers is obtained by synthesis, separation is generally not necessary, since the individual isomers may be interconverted during the workup or application (e.g., under the action of light, acid, or base) in some cases. Such conversions may also occur after use, for example, during plant treatment in treated plants, or within harmful fungi to be controlled.

[0066] Those skilled in the art will also readily understand that the preferences of the substituents, in particular the preferences shown in the table below for each substituent, as indicated herein in connection with compound I, apply accordingly to the intermediates, whereby the substituents in each case, independently of one another or, more preferably, in combination, have the meanings as defined herein.

[0067] Unless otherwise indicated, the term "compound according to the invention" or "compound of the invention" or "compound of formula (I)" means refers to a compound of formula I

[0068] The term "compound according to the invention" or "compound of formula I" includes not only the compound as defined herein, but also its stereoisomers, salts, tautomers, or N-oxides. The term "compound of the invention" should be understood to be equivalent to the term "compound according to the invention," and therefore includes its stereoisomers, salts, tautomers, or N-oxides.

[0069] The terms "composition according to the invention" or "composition of the invention" encompass compositions comprising at least one compound of formula I according to the invention as defined above. The composition of the invention is preferably an agricultural or veterinary composition.

[0070] Depending on the substitution pattern, the compounds according to the present invention may have one or more centers of chirality, and in this case, they exist as mixtures of enantiomers or diastereomers. The present invention provides both single pure enantiomers or pure diastereomers of the compounds according to the present invention and mixtures thereof, as well as the use according to the present invention of pure enantiomers or pure diastereomers of the compounds according to the present invention or mixtures thereof. Suitable compounds according to the present invention also include all possible geometric stereoisomers (cis / trans isomers) and mixtures thereof. With respect to alkenes, carbon-nitrogen double bonds, or amide groups, cis / trans isomers may exist. The term "stereoisomer" encompasses both optical isomers, such as enantiomers or diastereomers (the latter existing due to the presence of one or more centers of chirality in the molecule), and geometric isomers (cis / trans isomers). The present invention relates to all possible stereoisomers of the compounds of formula I, i.e., single enantiomers or diastereomers, as well as mixtures thereof.

[0071] The compounds according to the invention may be amorphous or may exist in one or more different crystalline states (polymorphs), which may exhibit different macroscopic properties, such as stability, or different biological properties, such as activity. The invention relates to amorphous and crystalline compounds according to the invention, mixtures of different crystalline states of each compound according to the invention, and amorphous or crystalline salts thereof.

[0072] The term "tautomer" encompasses isomers derived from the compounds of formula I by a shift of an H atom relative to at least one H atom located at a nitrogen, oxygen, or sulfur atom. Examples of tautomeric forms include keto-enol, imine-enamine, urea-isourea, thiourea-isothiourea, (thio)amide-(thio)imidate, etc.

[0073] The term "stereoisomer" encompasses both optical isomers, such as enantiomers or diastereomers (the latter existing due to one or more centers of chirality in the molecule), as well as geometric isomers (cis / trans isomers).

[0074] Depending on the substitution pattern, the compounds of formula I may have one or more centers of chirality, in which case they exist as mixtures of enantiomers or diastereomers. The present invention provides both pure enantiomers or pure diastereomers and mixtures thereof, as well as the use according to the invention of pure enantiomers or pure diastereomers of compound I or mixtures thereof. Suitable compounds of formula I also include all possible geometric stereoisomers (cis / trans isomers) and mixtures thereof.

[0075] 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, this term 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 is in particular, for example, a ring nitrogen atom of an N-heterocycle, such as Ar or R. 11 These compounds can be prepared by oxidizing the pyridine or pyrimidine ring present in the formula (I), or the imino nitrogen present in the central tricyclic core, with a suitable oxidizing agent, such as a peroxocarboxylic acid or other peroxide. Those skilled in the art will know whether and at what position the compounds of the present invention can form N-oxides.

[0076] Salts of compounds of formula I are preferably agriculturally and veterinarily acceptable salts and can be formed in the usual manner, for example, by reacting a compound of formula I, if it contains a basic functional group, with an acid of the anion of that compound, or by reacting an acidic compound of formula I with a suitable base.

[0077] Suitable agriculturally or veterinarily acceptable salts are, in particular, salts of those cations or acid addition salts of those acids whose cations and anions are known and accepted in the art to form salts for agricultural or veterinary use, respectively, and which do not have any adverse effect on the action of the compounds according to the invention. Suitable cations are, in particular, ions of alkali metals, preferably lithium, sodium and potassium, ions of alkaline earth metals, preferably calcium, magnesium and barium, and ions of transition metals, preferably manganese, copper, zinc and iron, and also ions of ammonium (NH 4+ ) and substituted ammonium ions in which 1 to 4 hydrogen atoms have been 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 the substituted ammonium ions include methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium, and benzyl-triethylammonium, as well as phosphonium ions, sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4 alkyl)sulfoxonium. For example, suitable veterinarily acceptable acid addition salts formed by compounds of formula I that contain 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, methanesulfenic acid, methanesulfonic acid, and succinic acid.

[0078] The anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphoric acid, nitrate, bicarbonate, carbonate, hexafluorosilicic acid, hexafluorophosphate, benzoic acid, and the anions of C1-C4 alkanoic acids, preferably formic acid, acetic acid, propionic acid, and butyric acid, which can be formed by reacting a compound of formula I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, or nitric acid.

[0079] The organic moieties referred to in the definitions of the variables above are generic terms for listing the individual elements individually, such as the term halogen. n ~C m The prefix "-" denotes in each case the possible number of carbon atoms in the group.

[0080] The term halogen denotes in each case F, Br, Cl or I, in particular F, Cl or Br.

[0081] As used herein, the term "alkyl" in the alkyl moiety of alkoxy, alkylthio, etc., refers to a saturated straight-chain or branched hydrocarbon group having 1 to 2 carbon atoms ("C1-C2 alkyl"), 1 to 3 carbon atoms ("C1-C3 alkyl"), 1 to 4 carbon atoms ("C1-C4 alkyl"), or 1 to 6 carbon atoms ("C1-C6 alkyl"). C1-C2 alkyl is CH3 or C2H5. Additionally, C1-C3 alkyl is propyl and isopropyl. Furthermore, C1-C4 alkyl is butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), or 1,1-dimethylethyl (tert-butyl). Furthermore, C1-C6 alkyl can also be, 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.

[0082] As used herein, the term "haloalkyl", also expressed as "partially or fully halogenated alkyl", refers to a straight-chain or branched alkyl group having 1 to 2 carbon atoms ("C1-C2 haloalkyl"), 1 to 3 carbon atoms ("C1-C3 haloalkyl"), 1 to 4 carbon atoms ("C1-C4 haloalkyl"), or 1 to 6 carbon atoms ("C1-C6 haloalkyl") (as mentioned above), wherein some or all of the hydrogen atoms of these groups have been replaced with halogen atoms as mentioned above, particularly C1-C2 haloalkyl. Examples of C1-C3 haloalkyl include 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, and pentafluoroethyl. Examples of C1-C3 haloalkyl include 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, and 3-chloropropyl. Examples of C1-C4 haloalkyl, apart from those mentioned for C1-C3 haloalkyl, include 4-chlorobutyl.

[0083] The term "alkylene" (or alkanediyl) as used herein means an alkyl group as defined above in each case in which one hydrogen atom at any position of the carbon skeleton is replaced by one further bonding site, thereby 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 are methylene (CH), 1,1-ethanediyl, 1,2-ethanediyl, 1,3-propanediyl, 1,2-propanediyl, 2,2-propanediyl, 1,4-butanediyl, 1,2-butanediyl, 1,3-butanediyl, 2,3-butanediyl, 2,2-butanediyl, 1,5-pentanediyl, 2,2-dimethylpropane-1,3-diyl, 1,3-dimethyl-1,3-propanediyl, 1,6-hexanediyl, and the like.

[0084] The term "alkenyl" as used herein refers to a monovalent unsaturated, straight-chain or branched hydrocarbon group having 2 to 3 carbon atoms ("C2-C3 alkenyl"), 2 to 4 carbon atoms ("C2-C4 alkenyl"), or 2 to 6 carbon atoms ("C2-C6 alkenyl") and a double bond at any position, for example, C2-C3 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, or 1-methylethenyl; ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methylethenyl, 1-methyl-2-propenyl, 2-methylethenyl, 1-methyl-3-propenyl, 1-methyl-4-propenyl, 1-methyl-5-propenyl, 1-methyl-6-propenyl, 1-methyl-7-propenyl, 1-methyl-8-propenyl, 1-methyl-9-propenyl, 1-methyl-1-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1-methyl-2-propenyl, 1-methyl-3-propenyl, 1-methyl-4 ...4-propenyl, 1-methyl-2 C2-C4 alkenyl such as ethenyl, 1-propenyl, 1-methyl-2-propenyl, or 2-methyl-2-propenyl; ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl- 2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-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, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,It refers to C2-C6 alkenyl such as 3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl, etc.

[0085] The term "alkynyl" as used herein refers to a straight-chain or branched hydrocarbon group having 2 to 3 carbon atoms ("C2-C3 alkynyl"), 2 to 4 carbon atoms ("C2-C4 alkynyl"), or 2 to 6 carbon atoms ("C2-C6 alkynyl") and one or two triple bonds at any position, for example, C2-C3 alkynyl such as ethynyl, 1-propynyl, or 2-propynyl; ethynyl, 1-propynyl, 2- C2-C4 alkynyl such as propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, etc., ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4- It refers to C2-C6 alkynyl such as methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, etc.

[0086] The term "cycloalkyl" as used herein refers specifically to a mono-, bi-, or polycyclic saturated hydrocarbon group having 3 to 6 carbon atoms ("C3-C6 cycloalkyl"), or 3 to 5 carbon atoms ("C3-C5 cycloalkyl"), or 3 to 4 carbon atoms ("C3-C4 cycloalkyl"). Examples of monocyclic groups having 3 to 4 carbon atoms include cyclopropyl and cyclobutyl. Examples of monocyclic groups having 3 to 5 carbon atoms include cyclopropyl, cyclobutyl, and cyclopentyl. Examples of monocyclic groups having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of monocyclic groups having 3 to 8 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of bicyclic groups 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 group.

[0087] The term "cycloalkoxy" as used herein refers to a cycloalkyl group, particularly a monocyclic cycloalkyl group, as defined above, particularly having 3 to 6 carbon atoms ("C-C cycloalkoxy") or 3 to 5 carbon atoms ("C-C cycloalkoxy") or 3 to 4 carbon atoms ("C-C cycloalkoxy"), attached to the remainder of the molecule via an oxygen atom.

[0088] The term "cycloalkyl-C1-C4 alkyl" refers to a C3-C8 cycloalkyl ("C3-C8 cycloalkyl-C1-C4 alkyl"), preferably a C3-C6 cycloalkyl ("C3-C6 cycloalkyl-C1-C4 alkyl"), more preferably a C3-C4 cycloalkyl ("C3-C4 cycloalkyl-C1-C4 alkyl") as defined above (preferably a monocyclic cycloalkyl group), bonded 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, and examples of C3-C6 cycloalkyl-C1-C4 alkyl, apart from the mention of C3-C4 cycloalkyl-C1-C4 alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, and cyclohexylpropyl.

[0089] The term "C1-C2 alkoxy" is a C1-C2 alkyl group as defined above bonded through an oxygen atom. The term "C1-C3 alkoxy" is a C1-C3 alkyl group as defined above bonded through an oxygen atom. The term "C1-C4 alkoxy" is a C1-C4 alkyl group as defined above bonded through an oxygen atom. The term "C1-C6 alkoxy" is a C1-C6 alkyl group as defined above bonded through an oxygen atom. "C1-C 10 The term "alkoxy" refers to a C1-C2 alkyl group, as defined above, attached through an oxygen atom. 10It is an alkyl group. C1-C2 alkoxy is OCH3 or OC2H5. Further, C1-C3 alkoxy is, for example, n-propoxy and 1-methylethoxy (isopropoxy). Further, C1-C4 alkoxy is, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy), or 1,1-dimethylethoxy (tert-butoxy). Furthermore, C1 to C6 alkoxy is, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 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. Furthermore, C1-C8 alkoxy includes, for example, heptyloxy, octyloxy, 2-ethylhexyloxy, and positional isomers thereof. 10 Alkoxy is, for example, nonyloxy, decyloxy and positional isomers thereof.

[0090] The term "C1-C2 haloalkoxy" is a C1-C2 haloalkyl group as defined above attached through an oxygen atom. The term "C1-C3 haloalkoxy" is a C1-C3 haloalkyl group as defined above attached through an oxygen atom. The term "C1-C4 haloalkoxy" is a C1-C4 haloalkyl group as defined above attached through an oxygen atom. The term "C1-C6 haloalkoxy" is a C1-C6 haloalkyl group as defined above attached through 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. Furthermore, C1-C3 haloalkoxy is, 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. Furthermore, C1-C4 haloalkoxy is, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, or nonafluorobutoxy. Furthermore, C1 to C6 haloalkoxy is, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

[0091] The term "C1-C6 alkoxy-C1-C4 alkyl" as used herein refers to a straight-chain or branched alkyl having 1 to 4 carbon atoms as defined above, in which one hydrogen atom is replaced by a C1-C6 alkoxy group as defined above. Examples include 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-ethoxy ... Examples include propyl, 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, and 3-tert-butoxypropyl.

[0092] The term "alkoxyalkoxy" as used herein refers to an alkoxyalkyl group, particularly a C1-C6 alkoxy-C1-C4 alkyl group as defined above, attached to the remainder of the molecule via an oxygen atom. Examples thereof are OCH2-OCH3, OCH2-OC2H5, n-propoxymethoxy, OCH2-OCH(CH3), n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH2-OC(CH3), 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.

[0093] An "oxo" substituent replaces a CH2 group with a C(=O) group.

[0094] The term "aryl" refers to a bicyclic or polycyclic carbocycle having a phenyl and at least one fused phenylene ring attached 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.

[0095] The term "aryl-C1-C4 alkyl" relates to a C1-C4 alkyl as defined above in which one hydrogen atom has been replaced by an aryl group, in particular a phenyl group. Particular examples of aryl-C1-C4 alkyl include -CH2-phenyl, 1-phenethyl, 2-phenethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenyl-1-propyl and 2-phenyl-2-propyl.

[0096] The term "aryloxy-C1-C4 alkyl" relates to a C1-C4 alkyl as defined above in which one hydrogen atom has been replaced by an aryloxy group, in particular a phenoxy group. Particular examples of aryloxy-C1-C4 alkyl include phenoxymethyl, 1-phenoxyethyl, 2-phenoxyethyl, 1-phenoxypropyl, 2-phenoxypropyl, 3-phenoxy-1-propyl and 2-phenoxy-2-propyl.

[0097] The term "aryl-C1-C4 carbonyl" refers to an aryl, especially a phenyl, group as defined above, attached to the rest of the molecule by a carbonyl. Particular examples of arylcarbonyl include benzoyl, 1-naphthoyl and 2-naphthoyl.

[0098] The term "hetaryl" refers to an aromatic heterocyclyl or heterocycle having either 5 or 6 ring atoms (5- or 6-membered hetaryl) and being monocyclic, or 8, 9 or 10 ring atoms and being bicyclic. Hetaryl generally has at least one ring atom selected from O, S and N, which in the case of N may be an imino nitrogen or amino nitrogen having hydrogen or a group different from hydrogen. Hetaryl may have 1, 2, 3 or 4 further nitrogen atoms as ring members, which are imino nitrogens. Examples of 5- or 6-membered hetaryl 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-imidazolyl, Examples include 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,3,4-oxadiazolyl-2-yl, 1,3,4-thiadiazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 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 hetaryl include, for example, quinolinyl, isoquinolinyl, cinnolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuryl, benzothienyl, benzo[b]thiazolyl, benzoxazolyl, benzthiazolyl, 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 5-, 6-, 7-, or 8-membered saturated heterocyclyls or heterocycles attached to N 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.

[0099] The term "hetaryl-C1-C4 alkyl" relates to a C1-C4 alkyl as defined above in which one hydrogen atom has been replaced by a hetaryl group, in particular a pyridyl group. Particular examples of hetaryl-C1-C4 alkyl 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, etc.

[0100] The term "hetaryloxy-C1-C4 alkyl" relates to a C1-C4 alkyl as defined above in which one hydrogen atom has been replaced by a hetaryloxy group, in particular a pyridyloxy group. Particular examples of hetaryloxy-C1-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, etc.

[0101] The term "hetaryl-C1-C4 carbonyl" refers to a hetaryl as defined above, in particular a C-bonded hetaryl group, attached to the remainder of the molecule by a carbonyl, such as a 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 group.

[0102] The term "substituted," unless otherwise specified, refers to substitution with one, two, or up to the maximum number of substituents possible. When there is more than one substituent as defined in a compound of Formula I, they are independent of each other and, unless otherwise specified, are the same or different.

[0103] In terms of variables, embodiments of compounds of formula I are as follows:

[0104] In one preferred embodiment, B 1 , B 2 and B 3 up to two of may be N; In another embodiment, B 1 is CR B1 and B 2 is CR B2 and B 3 is CR B3 and; In another embodiment, B 1 is N and B 2 is CR B2 and B 3 is CR B3 and; In another embodiment, B 1 is CR B1 and B 2 is N and B 3 is CR B3 and; In another embodiment, B 1 is CR B1 and B 2 is N and B 3 is N; In another embodiment, B1 is N and B 2 is N and B 3 is CR B3 and; In another embodiment, B 1 is CR B1 and B 2 is N or CR B2 and B 3 is N or CR B3 and; In another embodiment, B 3 is CR B3 and B 1 is N or CR B2 and B 2 is N or CR B3 and;

[0105] In one embodiment, A is N; In another embodiment, A is CR A is.

[0106] In one embodiment, R A is H, halogen, CN, C1-C6 alkyl, C1-C6 alkoxy, or C3-C6 cycloalkyl, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen or CN; In another embodiment, R A is H, halogen, CN, C1-C6 alkyl, or C3-C6 cycloalkyl; In another embodiment, R A is H, CN, or C1-C6 alkyl, the alkyl portion being unsubstituted or substituted with halogen or CN; In another embodiment, R A is H, CN, or C1-C6 alkyl, the alkyl portion being unsubstituted or substituted with halogen or CN; In another embodiment, R A is CN, or C1-C6 alkyl, unsubstituted or substituted with halogen or CN; In another embodiment, R A is CN; In another embodiment, RA is C1-C6 alkyl and is unsubstituted; In another embodiment, R A is C1-C6 alkyl and is substituted with halogen or CN; In another embodiment, R A is a C3-C6 cycloalkyl, unsubstituted or substituted with halogen or CN; In another embodiment, R A is a C3-C6 cycloalkyl and is unsubstituted; In another embodiment, R A is a C3-C6 cycloalkyl substituted with halogen or CN; In another embodiment, R A is H or halogen; In another embodiment, R A is H; In another embodiment, R A is a halogen; In another embodiment, R A is H, CH3, or CN; In another embodiment, R A is CH3 or CN; In another embodiment, R A is NR 6 R 7 and; In another embodiment, A is N, C(C1-C6 alkyl), or C(CN); In another embodiment, A is N, C(CH), or C(CN);

[0107] In one embodiment, R 6 and R 7 are the same or different and are 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 the alkyl, phenyl, and heteroaryl portions are unsubstituted or substituted with halogen, CN, or C1-C6 alkyl.

[0108] In one embodiment, R 6 and R 7 are the same or different and are H, phenyl, -CH-phenyl, 5- or 6-membered heteroaryl, -CH-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl, or 2-(methylamino)-2-oxo-ethyl, wherein the phenyl and heteroaryl moieties are unsubstituted or substituted with halogen or CN; In another embodiment, R 6 and R 7 are the same or different and are H, phenyl, -CH-phenyl, 5- or 6-membered heteroaryl, -CH-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl, or 2-(methylamino)-2-oxo-ethyl, wherein the phenyl and heteroaryl moieties are unsubstituted or substituted with halogen, CN, or C1-C6 alkyl; In another embodiment, R 6 and R 7 are the same or different and are H, —CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl, or 2-(methylamino)-2-oxo-ethyl, wherein the phenyl and heteroaryl moieties are unsubstituted or substituted with halogen, CN, or C1-C6 alkyl; 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 the alkyl, phenyl, and heteroaryl moieties are unsubstituted or substituted with halogen, CN, or C1-C6 alkyl; In another embodiment, R 6 and R 7 are independently selected from Rx-1 to Rx-7 as shown in Table Rx. [ka]

[0109] In another embodiment, R6 and R 7 are independently selected from Rx-1, Rx-2, Rx-7, and Rx-8. 2 is H, C1-C6 alkyl, or C3-C6 cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN;

[0110] In one embodiment, R 2 is H, C1-C6 alkyl, or C3-C6 cycloalkyl; In another embodiment, R 2 is H or C1-C6 alkyl, the alkyl portion being unsubstituted or substituted with halogen or CN; In another embodiment, R 2 is H or C3-C6 cycloalkyl, the cycloalkyl portion being unsubstituted or substituted with halogen or CN; In another embodiment, R 2 is C1-C6 alkyl, unsubstituted or substituted with halogen or CN; In another embodiment, R 2 is C1-C6 alkyl and is unsubstituted; In another embodiment, R 2 is C1-C6 alkyl and is substituted with halogen or CN; In another embodiment, R 2 is a C3-C6 cycloalkyl, unsubstituted or substituted with halogen or CN; In another embodiment, R 2 is a C3-C6 cycloalkyl and is unsubstituted; In another embodiment, R 2 is a C3-C6 cycloalkyl substituted with halogen or CN; In another embodiment, R 2 is H, CH3, C2H5, n-C3H7, isopropyl, cyclopropyl, CH2F, CHF2, or CF3.

[0111] In another embodiment, R 2is H, CH3, C2H5, isopropyl, or cyclopropyl; In another embodiment, R 2 is H or CH3; In another embodiment, R 2 is H; In another embodiment, R 2 is CH3; In another embodiment, R 2 is C2H5; In another embodiment, R 2 is isopropyl; In another embodiment, R 2 is cyclopropyl;

[0112] In one embodiment, R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; In another embodiment, R B1 , R B2 , R B3 , and R B4 are, independently of each other, H, halogen, CN, C1-C6 alkyl, or C1-C6 alkoxy, wherein the alkyl and alkoxy moieties are unsubstituted or substituted with halogen; In another embodiment, R B1 , R B2 , R B3 , and R B4 are, independently of each other, H, halogen, or C1-C6 alkyl, wherein the alkyl portion is unsubstituted or substituted with halogen; In another embodiment, R B1 , R B2 , R B3 , and R B4 are, independently of one another, H, Cl, Br, F, CN, CH3, C2H5, n-C3H7, isopropyl, cyclopropyl, CF3, CH2F, OCH3, or OCHF2; In another embodiment, R B1 , R B2 , R B3 , and R B4 are, independently of each other, H, Cl, Br, F, CN, CH3, isopropyl, OCH3, or OCHF2; In another embodiment, R B1 , R B2 , R B3 , and R B4 are, independently of each other, H, Cl, F, CN, CH3, or OCH3; In another embodiment, R B1 and R B4 are, independently of each other, H, Cl, or CH3; In another embodiment, R B2 and R B3 are, independently of each other, H, Cl, Br, F, CN, CH3, isopropyl, cyclopropyl, OCH3, or OCHF2; In another embodiment, R B2 and R B3 are, independently of each other, H, Cl, F, Br, CN, CH3, or OCH3;

[0113] In one embodiment, Q is —C(═O)—N(R 5 )-. In another embodiment, Q is —N(R 5 )-C(=O)-.

[0114] In one embodiment, R 5 is H, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkyl-C3-C6 cycloalkyl, wherein the alkyl and cycloalkyl portions are unsubstituted or substituted with halogen or CN; In another embodiment, R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-C3-C6 cycloalkyl, wherein the alkyl and cycloalkyl portions are unsubstituted or substituted with halogen or CN; In another embodiment, R 5is H, C1-C6 alkyl, or C1-C6 alkyl-C3-C6 cycloalkyl, wherein the alkyl and cycloalkyl portions are unsubstituted; In another embodiment, R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-C3-C6 cycloalkyl, wherein the alkyl and cycloalkyl moieties are substituted with halogen or CN; In another embodiment, R 5 is H, CH3, C2H5, or -CH2-CN; In another embodiment, R 5 is H, CH3 or C2H5; In another embodiment, R 5 is H or CH3;

[0115] In one embodiment, D is DA; In one embodiment, R 3 is H, C1-C6 alkyl, or C3-C6 cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN; In another embodiment, R 3 is H or C1-C6 alkyl, the alkyl portion being unsubstituted or substituted with halogen or CN; In another embodiment, R 3 is H or C3-C6 cycloalkyl, the cycloalkyl portion being unsubstituted or substituted with halogen or CN; In another embodiment, R 3 is H; In another embodiment, R 3 is H, and DA exists in either of the tautomeric forms D3 and D4 below. [ka]

[0116] In one embodiment, R 4is H, C1-C6 alkyl, or C3-C6 cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen, -O-(C=O)-C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, or CN; In another embodiment, R 4 is H or C1-C6 alkyl, wherein the alkyl portion is unsubstituted or substituted with halogen, -O-(C=O)-C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, or CN; In another embodiment, R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; In another embodiment, R 4 is H or C3-C6 cycloalkyl, the cycloalkyl portion being unsubstituted or substituted with halogen or CN; In another embodiment, R 4 is H or C1-C6 alkyl, wherein the alkyl portion is unsubstituted; In another embodiment, R 4 is H; In another embodiment, R 4 is H, and DA exists in either of the tautomeric forms D1 and D2 below. [ka]

[0117] In another embodiment, D is DB and B is a 5- or 6-membered carbocyclic group, one or two CH moieties of the carbocyclic group may be replaced with a carbonyl group, and the carbocyclic group may be unsubstituted or h is replaced by; In another embodiment, D is DB and B is a 5- or 6-membered carbocyclic group, one CH moiety of the carbocyclic group may be substituted with a carbonyl group, and the carbocyclic group may be unsubstituted or substituted with R h is replaced by; In another embodiment, D is DB and B is a 5- or 6-membered carbocyclic group, one CH2 moiety of which may be replaced with a carbonyl group; In another embodiment, D is DB and B is a 5- or 6-membered carbocyclic group in which one CH2 moiety of the carbocyclic group is replaced with a carbonyl group; In another embodiment, D is DB selected from D5 to D7, and the carbocyclic groups of the moieties D5 to D7 are unsubstituted or contain one or two substituents R h is replaced by [ka]

[0118] In another embodiment, D is a group selected from the moieties D5 to D7, and is unsubstituted or contains one or two substituents R h is replaced by [ka] In another embodiment, D is DB selected from D5-D7, and the carbocyclic groups of moieties D5-D7 are unsubstituted; In another embodiment, D is DB selected from D5 to D7, and the carbocyclic groups of the moieties D5 to D7 are each independently selected from one or two substituents R h is replaced by; In another embodiment, D is selected from D, D, D, and D, as defined herein; In another embodiment, D is selected from D A, D 5 , D 6 , and D 7 , and the D 5 , D 6 , and D 7 portions of the carbocyclic group are unsubstituted or contain one or two substituents R h is replaced by; In another embodiment, D is DA or D5, and D5 is unsubstituted or contains one substituent R h is replaced by; In another embodiment, D is selected from DA or D5, and the carbocyclic group of D5 is selected from one substituent R h is replaced by; In another embodiment, D is selected from DA or D5, and the carbocyclic group of D5 is unsubstituted; In another embodiment, D is D5, and the carbocyclic group of D5 is unsubstituted or contains one substituent R h is replaced by;

[0119] In one embodiment, Ar 1 is phenyl and is unsubstituted or R Ar1 is replaced by .

[0120] In another embodiment, Ar 1 is a 5- or 6-membered hetaryl, unsubstituted or R Ar1 is replaced by .

[0121] In a further embodiment, Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, preferably phenyl, and these moieties may be unsubstituted or Ar1 is replaced by .

[0122] In one embodiment, R Ar1 is halogen, SF, NO, OH, CN, C-C alkyl, C-C alkoxy, C-C cycloalkyl, C-C heterocyclyl, C-C cycloalkoxy, C-C alkenyl, C-C alkynyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C-C heterocyclyl, and cycloalkoxy moieties are unsubstituted or f , C(=O)-OR a , N.R. 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 is replaced by; In another embodiment, R Ar1 is halogen, SF, NO, CN, C-C alkyl, C-C alkoxy, C-C cycloalkyl, C-C heterocyclyl, C-C alkenyl, C-C alkynyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C-C heterocyclyl, and cycloalkoxy moieties are unsubstituted or substituted with R f , 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 is replaced by; In another embodiment, R Ar1 is halogen, SF, CN, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, and the alkyl, alkoxy, alkenyl, and alkynyl moieties are unsubstituted or f , Or S(=O) m R e is replaced by; In another embodiment, R Ar1 is halogen, CN, C1-C6 alkyl, C1-C6 alkoxy, and the alkyl and alkoxy moieties are unsubstituted or f is replaced by

[0123] In another embodiment of the compound of formula I, Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, preferably phenyl, and these moieties may be unsubstituted or Ar1 is replaced by; R Ar1is halogen, SF, NO, OH, CN, C-C alkyl, C-C alkoxy, C-C cycloalkyl, C-C heterocyclyl, C-C cycloalkoxy, C-C alkenyl, C-C alkynyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C-C heterocyclyl, and cycloalkoxy moieties are unsubstituted or f , C(=O)-OR a , N.R. 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 is replaced by; R a , R b and R c are the same or different and are H, C1-C6 alkyl, unsubstituted or substituted with 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, unsubstituted or substituted with halogen; m is 0, 1 or 2.

[0124] In another embodiment of the compound of formula I, Ar 1 is phenyl and is unsubstituted or R Ar1 is replaced by; R Ar1is halogen, SF, NO, OH, CN, C-C alkyl, C-C alkoxy, C-C cycloalkyl, C-C heterocyclyl, C-C cycloalkoxy, C-C alkenyl, C-C alkynyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C-C heterocyclyl, and cycloalkoxy moieties are unsubstituted or f , C(=O)-OR a , N.R. 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 is replaced by; R a , R b and R c are the same or different and are H, C1-C6 alkyl, unsubstituted or substituted with 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, unsubstituted or substituted with halogen; m is 0, 1 or 2.

[0125] In another embodiment of the compound of formula I, Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, preferably phenyl, and these moieties may be unsubstituted or Ar1 is replaced by; RAr1 is halogen, NO2, CN, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C6 heterocyclyl, C2-C6 alkenyl, C2-C6 alkynyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and C3-C6 heterocyclyl moieties are unsubstituted or f , 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 is replaced by; R a , R b and R c are the same or different and are H, C1-C6 alkyl, unsubstituted or substituted with 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, unsubstituted or substituted with halogen; m is 0, 1 or 2.

[0126] In another embodiment, Ar 1 Table Ar 1 Ar as shown in 1 -1~Ar 1 -30 is selected. [ka]

[0127] In another embodiment, Ar 1 Ar1 -1~Ar 1 -Selected from 14; In another embodiment, Ar 1 Ar 1 -1~Ar 1 -5 to choose from;

[0128] In one embodiment, Ar 2 is phenyl and is unsubstituted or R Ar2 is replaced by; In another embodiment, Ar 2 is a 5- or 6-membered hetaryl, unsubstituted or R Ar2 is replaced by; In another embodiment, Ar 2 is phenyl, pyrimidinyl, thiophenyl, thiazolyl, or pyridyl, and is unsubstituted or Ar2 is replaced by .

[0129] 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 cycloalkoxy, C3-C6 cycloalkyl-C1-C4 alkyl, C3-C6 cycloalkoxy-C1-C4 alkyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and cycloalkoxy moieties are unsubstituted or halogen, C(=O)-OR a , N.R. b R c or substituted with C1-C6 alkylene-CN; In another embodiment, R Ar2 is halogen, CN, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl, and the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen, or NR b R c is replaced by; In another embodiment, R Ar2 is halogen, CN, C1-C6 alkyl, the alkyl portion being unsubstituted or substituted with halogen; In another embodiment, R Ar2 is halogen or C1-C6 alkyl, the alkyl portion being unsubstituted or substituted with halogen; In another embodiment, R Ar2 is halogen or C1-C6 alkyl; In another embodiment, R Ar2 is a halogen; In another embodiment, R Ar2 is C1-C6 alkyl; In another embodiment, R Ar2 is halogen or CN; In another embodiment, Ar 2 is Ar as shown in Table Ar2 2 -1~Ar 2 -20 are selected. [ka]

[0130] In another embodiment, Ar 2 Ar 2 -1~Ar 2 -20 to choose from; In another embodiment, Ar 2 Ar 2 -1~Ar 2 -6 selected; In one embodiment, R a , R b and R c are the same or different and are H, C1-C6 alkyl, C2-C6 alkenyl, unsubstituted or substituted with halogen; In another embodiment, R a , R b and R c are the same or different and are H, C1-C6 alkyl, unsubstituted or substituted with halogen;

[0131] In one embodiment, R d is H; In another embodiment, R d is a C1-C6 alkyl.

[0132] In one embodiment, R e is C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, or C3-C6 halocycloalkyl; In another embodiment, R e is C1-C6 alkyl or C1-C6 haloalkyl;

[0133] 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, unsubstituted or substituted with halogen; In another embodiment, R f is halogen, OH, CN, or C1-C6 alkyl.

[0134] In one embodiment, R h is halogen or C1-C6 alkyl; In one embodiment, m is 0; In another embodiment, m is 1; In another embodiment, m is 2; In another embodiment, m is 0 or 1; In another embodiment, m is 1 or 2.

[0135] In another embodiment of the compound of formula I, Q is -C(=O)-N(R 5 )- or -N(R 5 )-C(=O)-; D is DA, D5, D6, or D7, preferably D5; B 1 is N or CR B1 and B 2 is CR B2and B 3 is CR B3 and; R B1 , R B2 , R B3 , and R B4 are each independently H, halogen, CN, C1-C6 alkyl, or C1-C6 alkoxy, wherein the alkyl and alkoxy moieties are unsubstituted or substituted with halogen; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-C3-C6 cycloalkyl; R A is H, halogen, CN, C1-C6 alkyl, or C3-C6 cycloalkyl; R 2 is H or C1-C6 alkyl; R 3 is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, preferably phenyl, and these moieties may be unsubstituted or Ar1 is replaced by; R Ar1 is halogen, SF, NO, OH, CN, C-C alkyl, C-C alkoxy, C-C cycloalkyl, C-C heterocyclyl, C-C cycloalkoxy, C-C alkenyl, C-C alkynyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C-C heterocyclyl, and cycloalkoxy moieties are unsubstituted or f , C(=O)-OR a , N.R. 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 is replaced by; R a , R b and R c are the same or different and are H, C1-C6 alkyl, unsubstituted or substituted with 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, unsubstituted or substituted with halogen; m is 0, 1 or 2.

[0136] In another embodiment of the compound of formula I, Q is -C(=O)-N(R 5 )-and; D is DB, preferably D5; B 1 is N or CR B1 and B 2 is CR B2 and B 3 is CR B3 and; R B1 , R B2 , R B3 , and R B4 are, independently of each other, H, halogen, CN, C1-C6 alkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-C3-C6 cycloalkyl; R Ais H, halogen, CN, C1-C6 alkyl, or C3-C6 cycloalkyl; R 2 is C1-C6 alkyl; Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, preferably phenyl, and these moieties may be unsubstituted or Ar1 is replaced by; R Ar1 is halogen, NO2, CN, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C6 heterocyclyl, C2-C6 alkenyl, C2-C6 alkynyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and C3-C6 heterocyclyl moieties are unsubstituted or f , 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 is replaced by; Ar 2 is phenyl and is unsubstituted or R Ar2 is replaced by; R Ar2 is halogen, CN, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, and the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen, NR b R c is replaced by; R a , R b and R c are the same or different and are H, C1-C6 alkyl, unsubstituted or substituted with halogen; R d is H or C1-C6 alkyl; R eis 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, unsubstituted or substituted with halogen; m is 0, 1 or 2.

[0137] In another embodiment, the compound of formula I is selected from the compounds of formulae A.1-A.20: [ka] In another embodiment, the compound of formula I is selected from the compounds of formulae A.1-A.5: In another embodiment, the compound of formula I is selected from the compounds of formulae A.6-A.10: In another embodiment, the compound of formula I is selected from the compounds of formulae A.11 to A.15: In another embodiment, the compound of formula I is selected from the compounds of formulae A.16 to A.20: In another embodiment, the compound of formula I is selected from compounds of formulae A.1-A.6; In another embodiment, the compound of formula I is selected from compounds of formulae A.11 to A.16; In another embodiment, the compound of formula I is selected from compounds of formulae A.12 to A.17; In another embodiment, the compound of formula I is selected from compounds of formulae A.15 to A.20; In another embodiment, the compound of formula I is selected from compounds of formulae A.1, A.6, A.16, A.17, and A.20; In another embodiment, the compound of formula I is selected from compounds of formulae A.1, A.6, A.16, and A.20; In another embodiment, the compound of formula I is selected from compounds of formulae A.1, A.6, A.11, and A.16; In another embodiment, the compound of formula I is selected from compounds of formulae A.2, A.7, A.12 and A.17; In another embodiment, the compound of formula I is selected from compounds of formulae A.3, A.8, A.13, and A.18; In another embodiment, the compound of formula I is selected from compounds of formulae A.4, A.9, A.14, and A.19; In another embodiment, the compound of formula I is selected from compounds of formulae A.5, A.10, A.15, and A.20; In another embodiment, the compound of formula I is A.1; In another embodiment, the compound of formula I is A.2; In another embodiment, the compound of formula I is A.3; In another embodiment, the compound of formula I is A.4; In another embodiment, the compound of formula I is A.5; In another embodiment, the compound of formula I is A.6; In another embodiment, the compound of formula I is A.7; In another embodiment, the compound of formula I is A.8; In another embodiment, the compound of formula I is A.9; In another embodiment, the compound of formula I is A.10; In another embodiment, the compound of formula I is A.11; In another embodiment, the compound of formula I is A.12; In another embodiment, the compound of formula I is A.13; In another embodiment, the compound of formula I is A.14; In another embodiment, the compound of formula I is A.15; In another embodiment, the compound of formula I is A.16; In another embodiment, the compound of formula I is A.17; In another embodiment, the compound of formula I is A.18; In another embodiment, the compound of formula I is A.19; In another embodiment, the compound of formula I is A.20;

[0138] In another embodiment, the compound of formula I is selected from compounds of formulae A.1, A.6, A.11 and A.16, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0139] In another embodiment, the compound of formula I is selected from the compounds of formulae A.1-A.5, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0140] In another embodiment, the compound of formula I is selected from the compounds of formulae A.6 to A.10, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0141] In another embodiment, the compound of formula I is selected from the compounds of formulae A.11 to A.15, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0142] In another embodiment, the compound of formula I is selected from the compounds of formulae A.16 to A.20, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2is H or C1-C6 alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0143] In another embodiment, the compound of formula I is selected from the compounds of formulae A.1-A.6, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0144] In another embodiment, the compound of formula I is selected from compounds of formula A.2 and A.7, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B3 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0145] In another embodiment, the compound of formula I is selected from compounds of formula A.3 and A.8, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0146] In another embodiment, the compound of formula I is selected from compounds of formula A.4 and A.9, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B3 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0147] In another embodiment, the compound of formula I is selected from compounds of formulae A.5 and A.10, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0148] In another embodiment, the compound of formula I is selected from A.1, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0149] In another embodiment, the compound of formula I is A.2, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B3 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0150] In another embodiment, the compound of formula I is A.3, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0151] In another embodiment, the compound of formula I is A.4, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B3 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0152] In another embodiment, the compound of formula I is A.5, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B2 , R B3 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0153] In another embodiment, the compound of formula I is A.6, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0154] In another embodiment, the compound of formula I is A.7, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0155] In another embodiment, the compound of formula I is A.8, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0156] In another embodiment, the compound of formula I is A.9, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5)—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0157] In another embodiment, the compound of formula I is A.10, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2is H or C1-C6 alkyl, preferably CH3; R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0158] In another embodiment, the compound of formula I is A.11, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0159] In another embodiment, the compound of formula I is A.12, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0160] In another embodiment, the compound of formula I is A.13, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0161] In another embodiment, the compound of formula I is A.14, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0162] In another embodiment, the compound of formula I is A.15, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or unsubstituted or halogen-substituted C1-C6 alkyl, -O-(C=O)-C1-C6 alkoxy, -O-(C=O)-C1-C6 alkyl or CN; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0163] In another embodiment, the compound of formula I is A.16, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0164] In another embodiment, the compound of formula I is A.17, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , R B3 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0165] In another embodiment, the compound of formula I is A.18, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B1 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2-1~Ar 2 -6 selected;

[0166] In another embodiment, the compound of formula I is A.19, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0167] In another embodiment, the compound of formula I is A.20, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R 5 )-and; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0168] In another embodiment, the compound of formula I is selected from the compounds of formulae I.1-I.8: [ka]

[0169] In another embodiment, the compound of formula I is selected from compounds of formulae I.1-I.2; In another embodiment, the compound of formula I is selected from compounds of formulae I.1-I.3; In another embodiment, the compound of formula I is selected from compounds of formulae I.3-I.4; In another embodiment, the compound of formula I is selected from compounds I.2 and I.4; In another embodiment, the compound of formula I is selected from compounds of formula I.5 and I.6; In another embodiment, the compound of formula I is selected from compounds of formula I.3 and I.7; In another embodiment, the compound of formula I is selected from compounds of formula I.5 and I.7; In another embodiment, the compound of formula I is selected from compounds of formula I.7 and I.8; In another embodiment, the compound of formula I is selected from compounds of formula I.6 and I.8; In another embodiment, the compound of formula I is a compound of formula I.1; In another embodiment, the compound of formula I is a compound of formula I.2; In another embodiment, the compound of formula I is a compound of formula I.3; In another embodiment, the compound of formula I is a compound of formula I.4; In another embodiment, the compound of formula I is a compound of formula I.5; In another embodiment, the compound of formula I is a compound of formula I.6; In another embodiment, the compound of formula I is a compound of formula I.7; In another embodiment, the compound of formula I is a compound of formula I.8;

[0170] In another embodiment, the compound of formula I is selected from the compounds of formulae I.1 to I.8, more preferably I.3 ​​and I.7, wherein: B 1 is N or CR B1 and B 2 is CR B2 and B 3 is CR B3 and; R B1 , R B2 , R B3 , and R B4 are, independently of each other, H, halogen, CN, C1-C6 alkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN; R A is H, halogen, CN, C1-C6 alkyl, or C3-C6 cycloalkyl; R 2 is C1-C6 alkyl; R 3is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, preferably phenyl, and these moieties may be unsubstituted or Ar1 is replaced by; R Ar1 is halogen, NO2, CN, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C6 heterocyclyl, C2-C6 alkenyl, C2-C6 alkynyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and C3-C6 heterocyclyl moieties are unsubstituted or f , 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 is replaced by; Ar 2 is phenyl and is unsubstituted or R Ar2 is replaced by; R Ar2 is halogen, CN, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, and the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen, NR b R c is replaced by; R a , R b and R c are the same or different and are H, C1-C6 alkyl, unsubstituted or substituted with halogen; R d is H or C1-C6 alkyl; R eis 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, unsubstituted or substituted with halogen; m is 0, 1 or 2.

[0171] In another embodiment, the compound of formula I is selected from the compounds of formulae I.1 to I.8, more preferably I.3 ​​and I.7, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, halogen, CN, C1-C6 alkyl, or C3-C6 cycloalkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl; Ar1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0172] In another embodiment, the compound of formula I is selected from the compounds of formulae I.1 to I.8, more preferably I.3 ​​and I.7, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0173] In another embodiment, the compound of formula I is selected from compounds of formula I.3 and I.7, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0174] In another embodiment, the compound of formula I is selected from compounds of formula I.1 and I.2, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0175] In another embodiment, the compound of formula I is selected from compounds of formula I.1 and I.3, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0176] In another embodiment, the compound of formula I is selected from compounds of formula I.3 and I.4, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0177] In another embodiment, the compound of formula I is selected from compounds of formula I.2 and I.4, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0178] In another embodiment, the compound of formula I is a compound of formula I.1, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0179] In another embodiment, the compound of formula I is a compound of formula I.2, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0180] In another embodiment, the compound of formula I is a compound of formula I.3, wherein: B 1 is N or CR B1 and B 2 is CR B2 and B 3 is CR B3 and; R B1 , R B2 , R B3 , and R B4 are, independently of each other, H, halogen, CN, C1-C6 alkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN; R A is H, halogen, CN, C1-C6 alkyl, or C3-C6 cycloalkyl; R 2 is C1-C6 alkyl; Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, preferably phenyl, and these moieties may be unsubstituted or Ar1 is replaced by; R Ar1is halogen, NO2, CN, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C6 heterocyclyl, C2-C6 alkenyl, C2-C6 alkynyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and C3-C6 heterocyclyl moieties are unsubstituted or f , 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 is replaced by; Ar 2 is phenyl and is unsubstituted or R Ar2 is replaced by; R Ar2 is halogen, CN, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, and the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen, NR b R c is replaced by; R a , R b and R c are the same or different and are H, C1-C6 alkyl, unsubstituted or substituted with 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, unsubstituted or substituted with halogen; m is 0, 1 or 2.

[0181] In another embodiment, the compound of formula I is a compound of formula I.3, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0182] In another embodiment, the compound of formula I is a compound of formula I.4, wherein: R 5is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R A is H, CN, or C1-C6 alkyl, preferably CN or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0183] In another embodiment, the compound of formula I is selected from compounds of formula I.5 and I.6, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0184] In another embodiment, the compound of formula I is selected from compounds of formula I.5 and I.7, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0185] In another embodiment, the compound of formula I is selected from compounds of formula I.7 and I.8, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0186] In another embodiment, the compound of formula I is selected from compounds of formula I.6 and I.8, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; RB1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0187] In another embodiment, the compound of formula I is a compound of formula I.5, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and RB4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0188] In another embodiment, the compound of formula I is a compound of formula I.6, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 3 is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl, unsubstituted or substituted with -O-(C=O)-C1-C6 alkoxy; / Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0189] In another embodiment, the compound of formula I is a compound of formula I.7, wherein: B 1 is N or CR B1 and B 2 is CR B2 and B 3 is CR B3 and; R B1 , R B2 , R B3 , and R B4 are, independently of each other, H, halogen, CN, C1-C6 alkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN; R 2 is C1-C6 alkyl; Ar 1is phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl, preferably phenyl, and these moieties may be unsubstituted or Ar1 is replaced by; R Ar1 is halogen, NO2, CN, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C6 heterocyclyl, C2-C6 alkenyl, C2-C6 alkynyl, and the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and C3-C6 heterocyclyl moieties are unsubstituted or f , 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 is replaced by; Ar 2 is phenyl and is unsubstituted or R Ar2 is replaced by; R Ar2 is halogen, CN, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, and the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen, NR b R c is replaced by; R a , R b and R c are the same or different and are H, C1-C6 alkyl, unsubstituted or substituted with halogen; R d is H or C1-C6 alkyl; R e is C1-C6 alkyl or C1-C6 haloalkyl; R fis halogen, OH, CN, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, unsubstituted or substituted with halogen; m is 0, 1 or 2.

[0190] In another embodiment, the compound of formula I is a compound of formula I.7, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0191] In another embodiment, the compound of formula I is a compound of formula I.8, wherein: R 5 is H, C1-C6 alkyl, or C1-C6 alkyl-CN, preferably H, CH3, C2H5, or —CH2—CN, more preferably H or CH3; R 2 is H or C1-C6 alkyl, preferably CH3; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CR B3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently from each other, H, halogen, CN, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -30, preferably Ar 1 -1~Ar 1 -5 to choose from; Ar 2 Ar 2 -1~Ar 2 -20, preferably Ar 2 -1~Ar 2 -6 selected;

[0192] Specific compounds of formula I are compounds of formula I.3, I.4, I.7 and I.8, which are summarized in Tables 1-720 below, and in which the variable B 1 , B 2 , B 3 , and B 4The combinations correspond to the respective rows of Table B. Furthermore, each of the groups mentioned for a substituent in the table is itself a particularly preferred embodiment of that substituent, independently of the combination mentioned.

[0193] Table 1.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0194] Table 2.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2.

[0195] Table 3.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -3.

[0196] Table 4.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0197] Table 5.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar2 -5.

[0198] Table 6.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0199] Table 7.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0200] Table 8.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2.

[0201] Table 9.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0202] Table 10.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0203] Table 11.RA is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5.

[0204] Table 12.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -6.

[0205] Table 13.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0206] Table 14.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0207] Table 15.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0208] Table 16.R A is CN and R 2 is H and R 5 is H and Ar1 Ar 1 -3 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0209] Table 17.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -5.

[0210] Table 18.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -6.

[0211] Table 19.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -1.

[0212] Table 20.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0213] Table 21.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2-3.

[0214] Table 22.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0215] Table 23.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -5.

[0216] Table 24.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -6.

[0217] Table 25.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -1.

[0218] Table 26.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0219] Table 27.RA is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0220] Table 28.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0221] Table 29.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -5.

[0222] Table 30.R A is CN and R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -6.

[0223] Table 31.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0224] Table 32.R A is CN and R 2 is H and R 5 is CH3 and Ar1 Ar 1 -1 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0225] Table 33.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -3.

[0226] Table 34.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0227] Table 35.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -5.

[0228] Table 36.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6.

[0229] Table 37.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar2 -1.

[0230] Table 38.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2.

[0231] Table 39.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0232] Table 40.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0233] Table 41.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5.

[0234] Table 42.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0235] Table 43.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0236] Table 44.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2.

[0237] Table 45.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0238] Table 46.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0239] Table 47.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -5.

[0240] Table 48.R A is CN and R 2is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -6.

[0241] Table 49.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -1.

[0242] Table 50.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0243] Table 51.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -3.

[0244] Table 52.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0245] Table 53.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar1 -4 and Ar 2 Ar 2 -5.

[0246] Table 54.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0247] Table 55.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -1.

[0248] Table 56.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -2.

[0249] Table 57.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0250] Table 58.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2-4 of the compound of formula I.3.

[0251] Table 59.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -5.

[0252] Table 60.R A is CN and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -6.

[0253] Table 61.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0254] Table 62.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0255] Table 63.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -3.

[0256] Table 64.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0257] Table 65.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -5.

[0258] Table 66.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6.

[0259] Table 67.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0260] Table 68.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0261] Table 69.R A is CN and R 2 is CH3 and R5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0262] Table 70.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0263] Table 71.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5.

[0264] Table 72.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -6.

[0265] Table 73.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0266] Table 74.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar2 Ar 2 -2.

[0267] Table 75.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0268] Table 76.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0269] Table 77.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -5.

[0270] Table 78.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0271] Table 79.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -1.

[0272] Table 80.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -2.

[0273] Table 81.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -3.

[0274] Table 82.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0275] Table 83.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -5.

[0276] Table 84.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0277] Table 85.R A is CN and R2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -1.

[0278] Table 86.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0279] Table 87.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0280] Table 88.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0281] Table 89.R A is CN and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -5.

[0282] Table 90.R A is CN and R 2 is CH3 and R 5 is H and Ar 1Ar 1 -5 and Ar 2 Ar 2 -6.

[0283] Table 91.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0284] Table 92.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0285] Table 93.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -3.

[0286] Table 94.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0287] Table 95.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar2 -5.

[0288] Table 96.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6.

[0289] Table 97.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0290] Table 98.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0291] Table 99.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0292] Table 100.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0293] Table 101.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5.

[0294] Table 102.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -6.

[0295] Table 103.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0296] Table 104.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0297] Table 105.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0298] Table 106.R Ais CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0299] Table 107.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -5.

[0300] Table 108.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0301] Table 109.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -1.

[0302] Table 110.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -2.

[0303] Table 111.R A is CN and R 2 is CH3 and R 5is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -3.

[0304] Table 112.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0305] Table 113.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -5.

[0306] Table 114.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -6.

[0307] Table 115.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -1.

[0308] Table 116.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1-5 and Ar 2 Ar 2 -2.

[0309] Table 117.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0310] Table 118.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0311] Table 119.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -5.

[0312] Table 120.R A is CN and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0313] Table 121.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2-1.

[0314] Table 122.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0315] Table 123.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -3.

[0316] Table 124.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0317] Table 125.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -5.

[0318] Table 126.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6.

[0319] Table 127.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0320] Table 128.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0321] Table 129.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0322] Table 130.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0323] Table 131.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5.

[0324] Table 132.R A is CH3 and R 2 is H and R5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -6.

[0325] Table 133.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0326] Table 134.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0327] Table 135.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0328] Table 136.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0329] Table 137.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar2 Ar 2 -5.

[0330] Table 138.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -6.

[0331] Table 139.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -1.

[0332] Table 140.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0333] Table 141.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -3.

[0334] Table 142.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0335] Table 143.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -5.

[0336] Table 144.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -6.

[0337] Table 145.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -1.

[0338] Table 146.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0339] Table 147.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0340] Table 148.R A is CH3 and R2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0341] Table 149.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -5.

[0342] Table 150.R A is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0343] Table 151.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0344] Table 152.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2.

[0345] Table 153.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1Ar 1 -1 and Ar 2 Ar 2 -3.

[0346] Table 154.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0347] Table 155.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -5.

[0348] Table 156.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0349] Table 157.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0350] Table 158.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar2 -2 of the compound of formula I.3.

[0351] Table 159.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0352] Table 160.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0353] Table 161.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5.

[0354] Table 162.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -6.

[0355] Table 163.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0356] Table 164.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0357] Table 165.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0358] Table 166.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0359] Table 167.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -5.

[0360] Table 168.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -6.

[0361] Table 169.R Ais CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -1.

[0362] Table 170.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -2.

[0363] Table 171.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -3.

[0364] Table 172.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0365] Table 173.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -5.

[0366] Table 174.R A is CH3 and R 2 is H and R 5is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0367] Table 175.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -1.

[0368] Table 176.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -2.

[0369] Table 177.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0370] Table 178.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0371] Table 179.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1-5 and Ar 2 Ar 2 -5.

[0372] Table 180.R A is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0373] Table 181.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0374] Table 182.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2.

[0375] Table 183.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -3.

[0376] Table 184.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2-4 of the compound of formula I.3.

[0377] Table 185.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -5.

[0378] Table 186.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6.

[0379] Table 187.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0380] Table 188.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0381] Table 189.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0382] Table 190.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0383] Table 191.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5.

[0384] Table 192.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0385] Table 193.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0386] Table 194.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2.

[0387] Table 195.R A is CH3 and R2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0388] Table 196.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0389] Table 197.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -5.

[0390] Table 198.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0391] Table 199.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -1.

[0392] Table 200.R A is CH3 and R 2 is CH3 and R 5 is H and Ar1 Ar 1 -4 and Ar 2 Ar 2 -2.

[0393] Table 201.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -3.

[0394] Table 202.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0395] Table 203.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -5.

[0396] Table 204.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0397] Table 205.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2Ar 2 -1.

[0398] Table 206.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -2.

[0399] Table 207.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0400] Table 208.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0401] Table 209.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -5.

[0402] Table 210.R A is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0403] Table 211.R A is CH 3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0404] Table 212.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2.

[0405] Table 213.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -3.

[0406] Table 214.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0407] Table 215.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -5.

[0408] Table 216.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0409] Table 217.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0410] Table 218.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2.

[0411] Table 219.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0412] Table 220.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0413] Table 221.R A is CH3 and R2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5.

[0414] Table 222.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -6.

[0415] Table 223.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0416] Table 224.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0417] Table 225.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0418] Table 226.R A is CH3 and R 2 is CH3 and R 5is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0419] Table 227.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -5.

[0420] Table 228.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0421] Table 229.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -1.

[0422] Table 230.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -2.

[0423] Table 231.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar1 -4 and Ar 2 Ar 2 -3.

[0424] Table 232.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0425] Table 233.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -5.

[0426] Table 234.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0427] Table 235.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -1.

[0428] Table 236.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar2 -2.

[0429] Table 237.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0430] Table 238.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -4 of the compound of formula I.3.

[0431] Table 239.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -5.

[0432] Table 240.R A is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -6 of the compound of formula I.3.

[0433] Table 241.R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0434] Table 242.R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0435] Table 243.R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -3.

[0436] Table 244.R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -4 of the formula I.7.

[0437] Table 245.R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0438] Table 246.R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6 of the compound of formula I.7.

[0439] Table 247.R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0440] Table 248.R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0441] Table 249.R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0442] Table 250.R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the formula I.7.

[0443] Table 251.R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0444] Table 252.R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -6 of the compound of formula I.7.

[0445] Table 253.R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0446] Table 254.R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2 of the formula I.7.

[0447] Table 255.R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0448] Table 256.R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -4 of the formula I.7.

[0449] Table 257.R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0450] Table 258.R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -6 of the formula I.7.

[0451] Table 259.R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -1.

[0452] Table 260.R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0453] Table 261.R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -3.

[0454] Table 262.R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the formula I.7.

[0455] Table 263.R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0456] Table 264.R 2 is H and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -6 of the compound of formula I.7.

[0457] Table 265.R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -1.

[0458] Table 266.R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0459] Table 267.R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0460] Table 268.R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -4 of the formula I.7.

[0461] Table 269.R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0462] Table 270.R 2 is H and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -6 of the compound of formula I.7.

[0463] Table 271.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0464] Table 272.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2 of the formula I.7.

[0465] Table 273.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -3.

[0466] Table 274.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -4 of the formula I.7.

[0467] Table 275.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0468] Table 276.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6 of the formula I.7.

[0469] Table 277.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0470] Table 278.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0471] Table 279.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0472] Table 280.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the formula I.7.

[0473] Table 281.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0474] Table 282.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -6 of the compound of formula I.7.

[0475] Table 283.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0476] Table 284.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0477] Table 285.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0478] Table 286.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -4 of the formula I.7.

[0479] Table 287.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0480] Table 288.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -6 of the compound of formula I.7.

[0481] Table 289.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2-1.

[0482] Table 290.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0483] Table 291.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -3.

[0484] Table 292.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the formula I.7.

[0485] Table 293.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0486] Table 294.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -6 of the compound of formula I.7.

[0487] Table 295.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar2 -1.

[0488] Table 296.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -2 of the formula I.7.

[0489] Table 297.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0490] Table 298.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -4 of the formula I.7.

[0491] Table 299.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0492] Table 300.R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -6 of the formula I.7.

[0493] Table 301.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar2 Ar 2 -1.

[0494] Table 302.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0495] Table 303.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -3.

[0496] Table 304.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -4 of the formula I.7.

[0497] Table 305.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0498] Table 306.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6 of the compound of formula I.7.

[0499] Table 307.R 2 is CH3 and R 5 is H and Ar 1 Ar1 -2 and Ar 2 Ar 2 -1.

[0500] Table 308.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2 of the formula I.7.

[0501] Table 309.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0502] Table 310.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the formula I.7.

[0503] Table 311.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0504] Table 312.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -6 of the formula I.7.

[0505] Table 313.R 2 is CH3 and R 5 is H and Ar1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0506] Table 314.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2 of the formula I.7.

[0507] Table 315.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0508] Table 316.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -4 of the formula I.7.

[0509] Table 317.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0510] Table 318.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -6 of the formula I.7.

[0511] Table 319.R 2 is CH3 and R5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -1.

[0512] Table 320.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0513] Table 321.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -3.

[0514] Table 322.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the formula I.7.

[0515] Table 323.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0516] Table 324.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -6 of the compound of formula I.7.

[0517] Table 325.R 2is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -1.

[0518] Table 326.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0519] Table 327.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0520] Table 328.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -4 of the formula I.7.

[0521] Table 329.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0522] Table 330.R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -6 of the compound of formula I.7.

[0523] Table 331.R2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0524] Table 332.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2 of the formula I.7.

[0525] Table 333.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -3.

[0526] Table 334.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -4 of the formula I.7.

[0527] Table 335.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0528] Table 336.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -6 of the formula I.7.

[0529] Table 337.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0530] Table 338.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0531] Table 339.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -3.

[0532] Table 340.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -4 of the formula I.7.

[0533] Table 341.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0534] Table 342.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2-6 of the compound of formula I.7.

[0535] Table 343.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0536] Table 344.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2 of the compound of formula I.7.

[0537] Table 345.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -3.

[0538] Table 346.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -4 of the formula I.7.

[0539] Table 347.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0540] Table 348.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar2 Ar 2 -6 of the formula I.7.

[0541] Table 349.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -1.

[0542] Table 350.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -2 of the formula I.7.

[0543] Table 351.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -3.

[0544] Table 352.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -4 of the formula I.7.

[0545] Table 353.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -4 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0546] Table 354.R 2 is CH3 and R 5 is CH3 and Ar 1Ar 1 -4 and Ar 2 Ar 2 -6 of the formula I.7.

[0547] Table 355.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -1.

[0548] Table 356.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -2 of the formula I.7.

[0549] Table 357.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -3.

[0550] Table 358.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -4 of the formula I.7.

[0551] Table 359.R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -5 of the compound of formula I.7.

[0552] Table 360.R 2 is CH3 and R 5is CH3 and Ar 1 Ar 1 -5 and Ar 2 Ar 2 -6 of the compound of formula I.7.

[0553] [Table 1]

[0554] [Table 2]

[0555] [Table 3]

[0556] [Table 4]

[0557] [Table 5]

[0558] [Table 6]

[0559] [Table 7]

[0560] [Table 8]

[0561] [Table 9]

[0562] [Table 10]

[0563] [Table 11]

[0564] [Table 12]

[0565] [Table 13]

[0566] [Table 14]

[0567] [Table 15]

[0568] [Table 16]

[0569] Tables 361 to 600: containing all compounds disclosed in Tables 1 to 240, respectively, where the compound of formula I.3 is replaced with the compound of formula I.4;

[0570] Tables 601 to 720: containing all compounds disclosed in Tables 241 to 360, respectively, where the compound of formula I.7 is replaced with the compound of formula I.8; The term "compounds of the invention" refers to compounds of Formula I or "Compound I," including salts, tautomers, stereoisomers, and N-oxides thereof.

[0571] The present invention also relates to an agrochemical composition comprising an adjuvant and at least one compound I.

[0572] The pesticidal composition comprises a pesticidally effective amount of Compound I.

[0573] Compound I can be converted into conventional types of pesticide compositions, such as solutions, emulsifiable concentrates, suspensions, dusts, powders, pastes, granules, compacts, capsules, and mixtures thereof. Examples of composition types are suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsifiable concentrates (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, pastilles, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), compacts (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticidal articles (e.g., LN), and gel formulations (e.g., GF) for treating plant propagation materials, such as seeds. These and other composition types are defined in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International. The compositions are prepared by known methods, for example as described in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0574] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, moisturizing agents, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, tackifiers and binders.

[0575] Suitable solvents and liquid carriers are water and organic solvents. Suitable solid carriers or fillers are minerals.

[0576] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, and polyelectrolytes. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International or North American Ed.). Suitable anionic surfactants are alkali, alkaline earth, or ammonium salts of sulfonates, sulfates, phosphates, and carboxylates. Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar surfactants, and polymeric surfactants. Suitable cationic surfactants are quaternary surfactants.

[0577] The pesticide composition generally contains 0.01 to 95% by weight, preferably 0.1 to 90% by weight, and most preferably 0.5 to 75% by weight of the active substance. The active substance is used at a purity of 90% to 100%, preferably 95% to 100%.

[0578] Various types of oils, wetting agents, adjuvants or fertilizers may be added to the active substances or compositions containing them as premixes or, if appropriate, just before use (tank mix). These agents can be mixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1.

[0579] The user typically applies the composition according to the invention from a predosage device, backpack sprayer, spray tank, spray aircraft, or irrigation system. Typically, the agrochemical composition is formulated to the desired application concentration with water, buffers, and / or further adjuvants, thus providing a ready-to-use spray solution or agrochemical composition according to the invention. Typically, 20 to 2000 liters of ready-to-use spray solution are applied per hectare of agricultural land.

[0580] Compound I is suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or the soil or water in which plants are grown, from infestation or infestation by animal pests. Accordingly, the present invention also relates to a method for protecting plants, which comprises contacting a crop, plant, plant propagation material, such as seeds, or the soil or water in which plants are grown, to be protected from infestation or infestation by animal pests, with a pesticidally effective amount of compound I.

[0581] Compound I is also suitable for use in combating or controlling animal pests. Accordingly, the present invention also relates to a method for combating or controlling animal pests, comprising contacting animal pests, their habitats, breeding grounds or food sources, or crops, plants, plant propagation materials such as seeds, or soil or areas, materials or environments in which animal pests are growing or may grow, with a pesticidally effective amount of Compound I.

[0582] Compound I is effective both by contact and ingestion and against all and any developmental stages, including eggs, larvae, pupae and adults.

[0583] The compounds I can be applied on their own or in the form of compositions containing them.

[0584] Application can be carried out both before and after infestation of the crop, plant or plant propagation material by pests.

[0585] The term "contact" includes both direct contact (applying a compound / composition directly to an animal pest or plant) and indirect contact (applying a compound / composition to a habitat).

[0586] The term "animal pests" includes arthropods, gastropods and nematodes. Preferred animal pests according to the present invention are arthropods, preferably insects and arachnids, especially insects.

[0587] The term "plant" includes cereals such as durum and other wheat, rye, barley, triticale, oats, rice or maize (fodder and sugar / sweet and field corn); beets, such as sugar beet or fodder beet; fruits, such as pome fruits, stone fruits or soft fruits, for example apple, pear, plum, peach, nectarine, almond, cherry, papaya, strawberry, raspberry, blackberry or gooseberry; legumes, such as beans, lentils, peas, alfalfa or soybeans; oil plants, such as rapeseed, oilseed rape, mustard, olive, sunflower, palm, cocoa bean, castor bean, oil palm, groundnut or soybean; cucurbits, such as pumpkin, pumpkin, cucumber or melon. fibre plants, such as cotton, flax, hemp or jute; citrus fruits, such as oranges, lemons, grapefruit or mandarins; vegetables, such as eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbage, carrots, onions, garlic, leeks, tomatoes, potatoes, melons or sweet peppers; lauraceae plants, such as avocado, cinnamon or camphor; energy plants and raw material plants, such as maize, soybeans, rapeseed, sugarcane or oil palm; tobacco; nuts, such as walnuts; pistachios; coffee; tea; bananas; vines; hops; sweetleaf (stevia); natural rubber plants or ornamental plants and forest plants, shrubs, broad-leaved or evergreen trees, eucalyptus; turf; lawn; grasses. Preferred plants include potato, sugar beet, tobacco, wheat, rye, barley, oat, rice, corn, cotton, soybean, rapeseed, legumes, sunflower, coffee, or sugarcane; fruits; vines; ornamental plants; or vegetables such as cucumber, tomato, bean, or pumpkin.

[0588] The term "seed" encompasses seeds and plant propagation materials (including true seeds, seed fragments, suckers, corms, bulbs, fruits, tubers, grains, cuttings and cut shoots), preferably true seeds.

[0589] "Pesticidally effective amount" means the amount of active ingredient required to obtain an observable effect on growth (including effects related to necrosis, killing, hindering, preventing, and eliminating, destroying, or otherwise gradually reducing the appearance and activity of target organisms). Pesticidally effective amounts may vary for various compounds / compositions used in the present invention. Pesticidally effective amounts of the compositions also vary depending on the prevailing conditions (e.g., desired pesticidal effect and duration, weather, target species, habitat, mode of application).

[0590] For example, when used in treating crop plants by foliar application, the amount of active ingredient of the invention applied may range from 0.0001 g to 4000 g per hectare, for example, from 1 g to 2 kg per hectare, or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare.

[0591] Compound I is also suitable for use against non-crop insect pests. When used against such non-crop pests, Compound I can be used as a bait composition, a gel, a general insect spray, an aerosol, a very low-volume application, and a mosquito net (impregnation or surface application).

[0592] The term "non-crop insect pest" refers to pests that are particularly associated with non-crop targets, such as 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 Blatella germanica, Periplaneta americana; ants, such as Solenopsis invicta, Argentine ant, Linepithema humile, and Camponotus pennsylvanicus.

[0593] The bait can be a liquid, solid, or semi-solid preparation (e.g., a gel). When used in a bait composition, the typical content of the active ingredient is 0.001% to 15% by weight of the active compound, preferably 0.001% to 5% by weight.

[0594] Compound I and compositions thereof can be used to protect wooden materials (e.g., trees, board fences, sleepers, framing, artistic artifacts, etc.) and buildings, as well as construction materials, furniture, leather, textiles, vinyl products, electrical wires and cables, from ants, termites, and / or wood- or fabric-destroying beetles (e.g., when pests invade homes and public facilities or nest in gardens, orchards, or parks), and to inhibit ant and termite damage to crops or humans.

[0595] A typical dosage for protecting materials is, for example, 1 m of treated material. 2 The amount of active compound is 0.001 g to 2000 g, or 0.01 g to 1000 g, preferably 1 m 2 Each serving weighs between 0.1g and 50g.

[0596] The insecticidal composition used in impregnating the material typically contains from 0.001 to 95% by weight, preferably from 0.1 to 45% by weight, more preferably from 1 to 25% by weight of at least one repellent and / or insecticide.

[0597] pest The compounds of the present invention are particularly suitable for effectively controlling animal pests, such as arthropods and nematodes, including: Insects of the suborder Auchenorrhyncha, for example, Amrasca biguttula, Empoasca spp., Nephotettix virescens, Sogatella furcifera, Mahanarva spp., Laodelphax striatellus, Nilaparvata lugens, Diaphorina citri; Lepidoptera, e.g., Helicoverpa spp., Heliothis virescens, Lobesia botrana, Ostrinia nubilalis, Plutella xylostella, Pseudoplusia includens, Scirpophaga incertulas, Spodoptera spp., Trichoplusia ni, Tuta absoluta, Cnaphalocrocis medialis, Cydia pomonella, Chilo spressoris suppressalis, Anticarsia gemmatalis, Agrotis ipsilon, Chrysodeixis includens; Hemiptera, for example, Lygus spp., stink bugs, for example, Euschistus spp., Halyomorpha halys, Nezara viridula, Piezodorus guildinii, Dichelops furcatus; Thrips, e.g., Frankliniella spp., Thrips spp., Dichromothrips corbettii; Aphids, for example Acyrthosiphon pisum, Aphis spp., Myzus persicae, Rhopalosiphum spp., Schizaphis graminum, Megoura viciae; Whiteflies, e.g., Trialeurodes vaporariorum, Bemisia spp.; Coleoptera, for example, Phyllotreta spp., Melanotus spp., Meligethes aeneus, Leptinotarsa ​​decimlineata, Ceutorhynchus spp., Diabrotica spp., Anthonomus grandis, Atomaria linearia, Agriotes spp., Epilachna spp.; Flies, e.g., Delia spp., Ceratitis capitate, Bactrocera spp., Liriomyza spp.; Coccoidea, e.g., Aonidiella aurantia, Ferrisia virgate; Arachnida arthropods (mites), for example, Penthaleus major, Tetranychus spp.; Nematodes, for example, Heterodera glycines, Meloidogyne spp., Pratylenchus spp., Caenorhabditis elegans.

[0598] Animal Health Compound I is suitable for use in treating or protecting animals from parasitic infestation or infection. Accordingly, the present invention also relates to the use of a compound of the present invention for the manufacture of a medicament for treating or protecting animals from parasitic infestation or infection. Furthermore, the present invention relates to a method for treating or protecting animals from parasitic infestation and infection, which comprises orally, topically or parenterally administering or applying to an animal a parasiticidally effective amount of Compound I.

[0599] 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. Furthermore, the present invention relates to a non-therapeutic method for treating or protecting animals from parasitic infestation and infection, which comprises applying to the locus a parasiticidally effective amount of Compound I.

[0600] The compounds of the present invention are further suitable for use in combating or controlling parasites in and on animals. The present invention further relates to a method of combating or controlling parasites in and on animals, which comprises contacting the parasites with a parasiticidally effective amount of Compound I.

[0601] The present invention also relates to the non-therapeutic use of compound I for combating or eliminating parasites. Furthermore, the present invention relates to a non-therapeutic method for combating or controlling parasites, which method comprises applying a parasiticidally effective amount of compound I to a locus.

[0602] Compound I can be effective both through contact (via soil, glass, walls, bed nets, carpets, blankets, or animal parts) and ingestion (e.g., bait). Furthermore, Compound I can be applied to any and all developmental stages.

[0603] The compounds I can be applied on their own or in the form of compositions containing them.

[0604] The term "habitat" means the habitat, food source, breeding ground, area, material or environment in which the parasite lives or may live outside of an animal.

[0605] As used herein, the term "parasite" includes endoparasites and ectoparasites. In some embodiments of the present invention, endoparasites may be preferred. In other embodiments, ectoparasites may be preferred. Infestations of warm-blooded animals and fish include lice, biting lice, ticks, bot flies, pediculid flies, stable flies, blowflies, flies, myiasis fly larvae, chiggers, black flies, mosquitoes, and fleas.

[0606] The compounds of the present invention are particularly useful for combating the following parasites: bed bugs (Cimex lectularius), brown dog ticks (Rhipicephalus sanguineus) and cat fleas (Ctenocephalides felis).

[0607] As used herein, the term "animal" includes warm-blooded animals (including humans) and fish. Mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, buffalo, donkeys, fallow deer and reindeer, as well as fur animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks, and fish such as freshwater and saltwater fish, eels, trout, carp and eels are preferred. Domestic animals such as dogs or cats are particularly preferred.

[0608] Compound I may be applied in a total amount of 0.5 mg / kg to 100 mg / kg per day, preferably 1 mg / kg to 50 mg / kg per day.

[0609] For oral administration to warm-blooded animals, Compound I may be formulated as animal feed, animal feed premix, animal feed concentrate, pill, liquid, paste, suspension, drench, gel, tablet, bolus, and capsule. For oral administration, the selected dosage form should provide the animal with 0.01 mg to 100 mg of Compound I per kg of animal body weight per day, preferably 0.5 mg to 100 mg per kg of animal body weight per day.

[0610] Alternatively, Compound I may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous, or subcutaneous injection. Compound I may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, Compound I may be formulated into an implant for subcutaneous administration. In addition, Compound I may be administered transdermally to animals. For parenteral administration, the selected dosage form should provide the animal with 0.01 mg to 100 mg of Compound I per kg of animal body weight per day.

[0611] Compound I may also be applied topically to animals in the form of dips, powders, dusts, collars, medallions, sprays, shampoos, spot-on formulations, and pour-on formulations, as well as in 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, preferably 1 ppm to 3,000 ppm, of Compound I. In addition, Compound I may be formulated as an ear tag for animals, particularly quadrupeds (e.g., cattle and sheep).

[0612] Oral solutions are administered directly.

[0613] Solutions for application to the skin are dripped, spread, rubbed, sprinkled, or sprayed onto the skin.

[0614] The gel is applied or spread on the skin or introduced into a body cavity.

[0615] Pour-on formulations are applied or sprayed onto a limited area of ​​the skin, allowing the active compound to penetrate the skin and act systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in a suitable skin-compatible solvent or solvent mixture.

[0616] The emulsion can be administered orally, transdermally, or as an injection.

[0617] The suspensions may be administered orally or topically / dermally.

[0618] Semi-solid preparations may be administered orally or topically / transdermally.

[0619] To produce solid preparations, the active compound is mixed with suitable excipients and, if appropriate with the addition of auxiliaries, brought into the desired form.

[0620] The compositions that can be used in the present invention can generally contain Compound I in an amount of about 0.001 to 95%.

[0621] The ready-to-use preparations contain compounds 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.

[0622] The preparation to be diluted before use contains the compound acting against ectoparasites in a concentration of 0.5 to 90% by weight, preferably 1 to 50% by weight.

[0623] Furthermore, the preparation contains a compound 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.

[0624] The solid formulations releasing the compounds of the present invention may be applied in a total amount of 10 mg to 300 mg, preferably 20 mg to 200 mg, most preferably 25 mg to 160 mg per kg of body weight of the treated animal for a period of 3 weeks. [Example]

[0625] Working Example: Using procedures as described in the preparative examples below, with appropriate modification of the starting materials, additional compounds of Formula I were obtained. Compounds obtained in this manner are listed below in Table C, along with their physical data.

[0626] Compounds were analyzed by coupled high performance liquid chromatography / mass spectrometry (HPLC / MS), 1 They can be characterized by 1 H NMR and / or their melting points.

[0627] Compounds were analyzed by coupled high performance liquid chromatography / mass spectrometry (HPLC / MS), 1 They can be characterized by 1 H NMR and / or their melting points.

[0628] Analytical HPLC - Method 1: Agilent Eclipse Plus C18, 50 x 4.6 mm, ID 5 μm; Elution: A = 10 mM Amm. Formic acid (0.1% formic acid), B = acetonitrile (0.1% formic acid), Flow rate = 1.2 ml / min, 30 °C; Gradient: 10% B to 100% B - 3 min, 1 min hold, 1 min - 10% B. Run time = 5.01 min.

[0629] Analytical HPLC - Method 2: Kinetex XB C18 1.7μ 50×2.1 mm; A = water + 0.1% TFA, B = acetonitrile, flow rate = 0.8 ml / min to 1.0 ml / min in 1.5 min, 60 °C; gradient: 5% B to 100% B in 1.5 min.

[0630] Analytical HPLC - Method 3: Diamonsil plus 5 μm, 30 × 3.0 mm; A = water + 0.05% TFA, B = acetonitrile, flow rate = 2 ml / min, 40 °C; gradient: 5% B to 95% B - 0.8 min, hold for 0.75 min, then 95% B to 5% B - 0.25 min.

[0631] 1 H NMR: Tetramethylsilane ( 13 For C NMR, signals are identified by their chemical shift (ppm, d [delta]) relative to CDCl3), their multiplicity, and their integral (relative number of hydrogen atoms given). To identify signal multiplicity, the following abbreviations are used: m = multiplet, q = quartet, t = triplet, d = doublet, and s = singlet.

[0632] The abbreviations used are as follows: d is days, h is hours, min is minutes, RT is room temperature (20-25°C), Rt is retention time; DMSO is dimethyl sulfoxide, OAc is acetate, EtOAc is ethyl acetate, IPA is isopropyl alcohol, MeOH is methanol, EtOH is ethanol, THF is tetrahydrofuran, DCM is dichloromethane, DMF is N,N-dimethylformamide, and t-BuOH is tert-butanol.

[0633] Example C-1: 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) Step 1: Synthesis of 3-(4-bromophenyl)-2-methyl-3-oxo-propanenitrile To a stirred solution of ethyl 4-bromobenzoate (30 g) in THF (600 mL) was added potassium tert-butoxide (29.39 g) at ambient temperature. After 10 minutes, propionitrile (7.213 g) was added to the reaction mass at ambient temperature. The reaction mixture was stirred at ambient temperature for 1 hour, and after the reaction was complete, the mixture was diluted with 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 as a yellowish oil (24 g). HPLC / MS (Method 1): Retention time: 1.821 min; m / z=236 (M-1) + .

[0634] Step 2: Synthesis of 5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-amine To a stirred solution of 3-(4-bromophenyl)-2-methyl-3-oxo-propanenitrile (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 hours, and after the reaction was complete, EtOH was removed under reduced pressure and the crude 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 as a solid (23 g). HPLC / MS (Method 1): Retention time: 1.656 min; m / z=266(M+1) + .

[0635] Step 3: Synthesis of N-[5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide To a stirred solution of 5-(4-bromophenyl)-2,4-dimethyl-pyrazol-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 hours. 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 as a solid (44 g). HPLC / MS (Method 1): Retention time: 2.066 min; m / z=438(M+1) + .

[0636] Step 4: Synthesis of tert-butyl N-[4-[1,4-dimethyl-5-[[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate To a stirred solution of N-[5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide (2.5 g) in 1,4-dioxane (30 mL) was added tert-butyl carbamate (0.802 g), palladium(II) acetate (0.128 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.544 g), and cesium carbonate (3.717 g) under an inert atmosphere at ambient temperature. The reaction mixture was heated at 100°C for 16 hours. 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 resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound (2.2 g) as a solid. HPLC / MS (Method 1): Retention time: 1.918 min; m / z=475(M+1) + .

[0637] Step 5: Synthesis of N-[5-(4-aminophenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide 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 hours, and after completion of the reaction, the mixture was neutralized with aqueous sodium bicarbonate. The mixture was extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound (1.2 g) as a solid. HPLC / MS (Method 1): Retention time: 1.727 min; m / z=375(M+1) + .

[0638] Step 6: Synthesis of (4-nitrophenyl)N-[4-[1,4-dimethyl-5-[[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate 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)carbonochloridate (0.108 g) under an inert atmosphere at 0° C. The reaction mixture was stirred at ambient temperature for 3 hours, and after completion of the reaction, the solvent was evaporated from the reaction mixture in vacuo to give the title compound as a solid (0.2 g). HPLC / MS (Method 1): Retention time: 1.885 min; m / z=540(M+1) + .

[0639] 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) 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 tribasic potassium phosphate (0.118 g) at ambient temperature. The reaction mixture was stirred at ambient temperature for 19 hours. 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 resulting residue was subjected to preparative HPLC purification eluting with a gradient of acetonitrile and water to give the title compound (0.17 g) as a solid. HPLC / MS (Method 1): Retention time: 1.960 min; m / z=649(M+1) + . 1 H NMR (300 MHz, DMSO-d6) δ 10.47(s,1H),9.86(s,1H),8.23(d,J=8.1Hz,2H),7.97(d,J=8.2Hz,2H),7.7 3(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).

[0640] Synthesis of 2-imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (E1) Step 1: Synthesis of 2-chloro-N-(2-isopropyl-5-methyl-phenyl)acetamide 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 minutes and the reaction mixture was stirred at ambient temperature for 16 hours. After the reaction was complete, the mixture was diluted with 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 yellowish oil. HPLC / MS (Method 1): Retention time: 1.813 min; m / z=223.70 (M-1) + .

[0641] Step 2: Synthesis of 2-imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (E1) 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 then refluxed for 4 hours. After the reaction was complete, the mixture was diluted with aqueous sodium bicarbonate and 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 (0.42 g) as a solid. HPLC / MS (Method 1): Retention time: 1.675 min; m / z=249(M+1) + .

[0642] Example C-2: 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) 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 hours. 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 resulting residue was subjected to preparative HPLC purification eluting with a gradient of acetonitrile and water to give the title compound (0.18 g) as a solid. HPLC / MS (Method 1): Retention time: 2.205 min; m / z=681 (M+1) + . 1 H NMR(500MHz,DMSO-d6)δ 11.27(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),7.26-7.0 6(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),3.0 3(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).

[0643] Synthesis of [N-(2-isopropyl-5-methyl-phenyl)carbamimidoyl]sulfanylmethyl acetate hydrobromide (E1') Step 1: N-[(2-isopropyl-5-methyl-phenyl)carbamothioyl]benzamide 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 hours, and after completion of the reaction, the solvent was evaporated in vacuo from the reaction mixture to give the title compound as a solid (0.8 g). HPLC / MS (Method 1): Retention time: 2.153 min; m / z=313(M+1) + .

[0644] Step 2: [(1E)-1-Isobutyl-3-methyl-buta-1,3-dienyl]thiourea A stirred solution of N-[(2-isopropyl-5-methyl-phenyl)carbamothioyl]benzamide (0.8 g) in 2N sodium hydroxide (10 mL) was heated at 90° C. for 2 hours. 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 resulting 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): Retention time: 1.584 min; m / z=209 (M+1). + .

[0645] Step 3: Synthesis of [N-(2-isopropyl-5-methyl-phenyl)carbamimidoyl]sulfanylmethyl acetate hydrobromide (E1') 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 hours, and after completion of the reaction, the solvent was evaporated in vacuo to give the title compound as an oil (0.1 g). HPLC / MS (Method 1): Retention time: 1.936 min; m / z=281(M+1) + .

[0646] Example C-3: Preparation of N-[5-[4-[(2-isopropyl-5-methyl-phenyl)carbamothioylcarbamoylamino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide (C-3) 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 hours. After completion of the reaction, the solvent was evaporated from the reaction mixture in vacuo. The resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound (0.085 g) as a solid. HPLC / MS (Method 1): Retention time: 2.173 min; m / z=609(M+1) + . 1 H NMR(500MHz,DMSO-d6)δ 11.68(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).

[0647] Example C-4: 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) Step 1: N-[5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide N-[5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethyl)benzamide (0.5 g) was dissolved in DMF (12.5 mL), followed by the addition of cesium carbonate (0.74 g) and methyl iodide (0.2 g). The reaction mixture was stirred at 50° C. for 3 hours. When the starting material was consumed, the reaction mixture was cooled to room temperature and EtOAc was added. The resulting precipitate was filtered, the solvent 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).

[0648] Step 2: tert-butyl-N-[4-[1,4-dimethyl-5-[methyl-[4-(trifluoromethyl)benzoyl]amino]pyrazol-3-yl]phenyl]carbamate N-[5-(4-bromophenyl)-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide (0.52 g) was dissolved in 1,4-dioxane (5 mL), followed by the addition of tert-butyl carbamate (0.20 g), cesium carbonate (0.90 g), palladium(II) acetate (0.04 g), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.14 g) under nitrogen purging. The resulting mixture was stirred at 100 °C overnight. Once the starting material was consumed, the reaction mixture was cooled to room temperature and quenched by the addition of water (7 mL), and the organic phase was 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). 1 H NMR(500MHz,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).

[0649] Step 3: N-[5-(4-aminophenyl)-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4-(trifluoromethyl)benzamide 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).

[0650] 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) N-[5-(4-aminophenyl)-2,4-dimethyl-pyrazol-3-yl]-N-methyl-4(trifluoromethyl)benzamide (0.1 g) was dissolved in acetonitrile (7 mL), followed by the addition of cesium carbonate (0.07 g) and 4-nitrophenyl chloroformate (0.05 g). The reaction mixture was stirred at room temperature for 5 hours. When TLC showed 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)

[0651] Example C-5: 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) Step 1: Methyl 4-bromobenzenecarboximidate 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 the reaction was complete, the mixture was evaporated. The precipitated solid was filtered, washed with methyl tert-butyl ether, and dried in vacuo to give the title compound as a white solid (10 g). HPLC / MS (Method 1): Retention time: 0.86 min; m / z=214 (M). + .

[0652] Step 2: Methyl (1Z)-4-bromo-N-cyano-benzenecarboximidate To a stirred solution of methyl 4-bromobenzenecarboximidate HCl salt (3 g) in water (50 mL) was added cyanamide (1.374 g) and disodium hydrogen phosphate (3.315 g) at ambient temperature. The reaction mixture was stirred at ambient temperature for 19 hours, and after the reaction was complete, the mixture was diluted with 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 as a yellowish oil (3 g). 1 H NMR(300MHz,chloroform-d)δ 8.00(d,J=8.7Hz,2H),7.68(d,J=8.7Hz,2H),4.08(s,3H).

[0653] Step 3: 5-(4-bromophenyl)-2-methyl-1,2,4-triazol-3-amine To a stirred solution of methyl (1Z)-4-bromo-N-cyano-benzenecarboximidate (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 hours. After the reaction was complete, the reaction mixture was cooled to ambient temperature, and the precipitated solid was filtered, washed with MeOH, and dried in vacuo to give the title compound as a white solid (3 g). HPLC / MS (Method 1): Retention time: 1.25 min; m / z=253 (M). + .

[0654] Step 4: N-[5-(4-bromophenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide To a stirred solution of 5-(4-bromophenyl)-2-methyl-1,2,4-triazol-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 hours. The reaction mixture was dissolved in water, and the mixture was extracted with DCM. The organic extract was washed with aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, and evaporated in vacuo. The resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound (1 g) as a solid. HPLC / MS (Method 1): Retention time: 2.13 min; m / z = 441 (M). + .

[0655] Step 5: Synthesis of tert-butyl N-[4-[1-methyl-5-[[4-(trifluoromethoxy)benzoyl]amino]-1,2,4-triazol-3-yl]phenyl]carbamate 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-butylcarbamate (2.39 g), tris(dibenzylideneacetone)dipalladium(0) (1.245 g), 5-(di-tert-butylphosphino)-1',3',5'-triphenyl-1'H-[1,4']bipyrazole (0.689 g), and potassium tert-butoxide (4.578 g) under an inert atmosphere at ambient temperature. The reaction mixture was heated at 90°C for 16 hours. 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 resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound as a solid (5.8 g). HPLC / MS (Method 1): Retention time: 2.12 min; m / z=478 (M+1). + .

[0656] Step 6: N-[5-(4-aminophenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide 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 hours, 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 in vacuo to give the title compound as a solid (4.1 g). HPLC / MS (Method 1): Retention time: 1.69 min; m / z = 378 (M+1). + .

[0657] 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) 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)carbonochloridate (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 resulting residue was subjected to preparative HPLC purification eluting with a gradient of acetonitrile and water to give the title compound (0.118 g) as a solid. HPLC / MS (method 1): Retention time: 5.84 minutes; m / z=650 (M-1) + . 1 H NMR (500 MHz, DMSO-d6) δ 11.28(s,1H),9.95(s,1H),8.20-8.15(m,2H),7.86(d,J=8.4Hz,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).

[0658] Example C-6: 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) Step 1: N-[5-(4-amino-3-chloro-phenyl)-2-methyl-1,2,4-triazol-3-yl]-4-(trifluoromethoxy)benzamide 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 hours, and after the reaction was complete, the mixture was diluted with water. The mixture was extracted with EtOAc, and the organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound (1.25 g) as a yellow solid. HPLC / MS (Method 1): Retention time: 2.02 min; m / z=412.2(M+1)+ .

[0659] 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) 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)carbocloridate (0.587 g) under an inert atmosphere at 0° C. The reaction mixture was stirred at ambient temperature for 3 hours. Then, acetonitrile (10 mL) was added. 2-Imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (E1, 0.905 g), N,N,N-diisopropylethylamine (0.628 g), and tribasic potassium phosphate (0.635 g) were added at 0° C. The reaction mixture was stirred at 27° C. for 16 hours. After the reaction was complete, the mixture was diluted with water. The mixture was extracted with EtOAc, and the organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The resulting residue was triturated in MeOH and filtered to give the title compound as a white solid (1.2 g). HPLC / MS (Method 1): Retention time: 2.34 min; m / z=686.4 (M+1). + . 1 H NMR(500MHz,DMSO-d6)δ 11.32(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).

[0660] Example C-7: 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) Step 1: Synthesis of 3,5-dibromo-1H-pyrazole-4-carbonitrile 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 hours. 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 in vacuo to give the title compound (4.9 g). HPLC / MS (Method 1): Retention time: 1.73 min; m / z=252 (M+2). + .

[0661] Step 2: Synthesis of 3,5-dibromo-1-methyl-pyrazole-4-carbonitrile 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 methyl iodide (4.158 g) at ambient temperature. The reaction mixture was stirred at ambient temperature for 17 hours. The reaction mixture was dissolved in water, and the precipitated solid was filtered, washed with water, and dried in vacuo to give the title compound as a white solid (50 g). HPLC / MS (Method 1): Retention time: 1.82 min; m / z=266 (M+1). + .

[0662] Step 3: Synthesis of 5-amino-3-bromo-1-methyl-pyrazole-4-carbonitrile To a stirred solution of 3,5-dibromo-1-methyl-pyrazole-4-carbonitrile (7 g) in N-methyl-2-pyrrolidone (14 mL) was added 2,4-dimethoxybenzylamine (8.83 mL) at ambient temperature. The reaction mixture was stirred at 140° C. for 2 hours. After the reaction was complete, 5N hydrochloric acid (50 mL) was added, and the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was dissolved in water, and the mixture was extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate and evaporated in vacuo. The resulting residue was subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and heptane, to give the title compound (5.8 g) as a solid. HPLC / MS (Method 1): Retention time: 1.01 min; m / z=203(M+2) + .

[0663] Step 4: Synthesis of N-(5-bromo-4-cyano-2-methyl-pyrazol-3-yl)-4-(trifluoromethoxy)benzamide To a stirred solution of 5-amino-3-bromo-1-methyl-pyrazole-4-carbonitrile (7 g) in DCM (70 mL) was added pyridine (14 mL) and 4-(trifluoromethoxy)benzoyl chloride (6.7 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 24 hours. The reaction mixture was dissolved in water, and the mixture was extracted with DCM. The organic extract was washed with 2.5 M hydrochloric acid, dried over anhydrous sodium sulfate, and evaporated in vacuo. The resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound (2.5 g) as a solid. HPLC / MS (Method 1): Retention time: 2.02 min; m / z=389(M) + .

[0664] Step 5: Synthesis of N-[5-(4-aminophenyl)-4-cyano-2-methyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide To a stirred solution of N-(5-bromo-4-cyano-2-methyl-pyrazol-3-yl)-4-(trifluoromethoxy)benzamide (3.2 g) in 1,4-dioxane (30 mL) and water (3 mL) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.98 g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.602 g), and potassium carbonate (1.70 g) under an inert atmosphere at ambient temperature. The reaction mixture was heated at 80°C for 8 hours, 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 resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound (2.05 g) as a solid. HPLC / MS (method 1): Retention time: 1.93 min; m / z=402 (M+1) + .

[0665] 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) 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 hours. After 3 hours, 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 hours. 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 resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound as a solid (0.175 g). HPLC / MS (Method 1): Retention time: 2.523 min; m / z=675 (M-1). + . 1 H NMR(500MHz,DMSO-d6)δ 11.13(s,1H),9.99(s,1H),8.20-8.15(m,2H),7.79(q,J=8.5Hz,4H),7.6 2(d,J=8.3Hz,2H),7.40(d,J=8.3Hz,1H),7.28(d,J=8.0Hz,1H),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).

[0666] Example C-8: 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) Step 1: Synthesis of N-[(1-amino-2-methyl-prop-1-enyl)-methyl-amino]formamide To a stirred solution of ethyl 2-cyanopropanoate (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 hours, and after the reaction was complete, the mixture was evaporated. The precipitated solid was filtered, washed with heptane, and dried to give the title compound as a solid (2.9 g). HPLC / MS (Method 1): Retention time: 1.90 min; m / z=128.3 (M+1). + .

[0667] Step 2: Synthesis of (5-amino-1,4-dimethyl-pyrazol-3-yl)trifluoromethanesulfonate To a stirred solution of 3-amino-2,4-dimethyl-1H-pyrazol-5-one (1.6 g) in DMF (20 mL) was added 1,1,1-trifluoro-N-phenyl-N-(trifluoromethylsulfonyl)methanesulfonamide (5.39 g) and N,N,N-diisopropylethylamine (4.87 g) at 0 °C. The reaction mixture was stirred at ambient temperature for 17 hours, 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 resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound (3.15 g) as a solid. HPLC / MS (Method 1): Retention time: 1.90 min; m / z=260 (M+1) + .

[0668] Step 3: Synthesis of [1,4-dimethyl-5-[[4-(trifluoromethoxy)benzoyl]amino]pyrazol-3-yl]trifluoromethanesulfonate To a stirred solution of (5-amino-1,4-dimethyl-pyrazol-3-yl)trifluoromethanesulfonate (3 g) in DCM (30 mL) was added pyridine (9.34 mL) and 4-(trifluoromethoxy)benzoyl chloride (2.85 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 24 hours. 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 resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound (3.15 g) as a white solid. HPLC / MS (Method 1): Retention time: 2.16 min; m / z=448(M+1) + .

[0669] Step 4: Synthesis of N-[5-(4-amino-3-chloro-phenyl)-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide To a stirred solution of [1,4-dimethyl-5-[[4-(trifluoromethoxy)benzoyl]amino]pyrazol-3-yl]trifluoromethanesulfonate (1 g) in 1,4-dioxane (10 mL) was added 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.595 g), tetrakis(triphenylphosphine)palladium(0) (0.517 g), and potassium carbonate (0.618 g) under an inert atmosphere at ambient temperature. The reaction mixture was heated at 120 °C for 18 hours. 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 resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound (0.59 g) as a solid. HPLC / MS (Method 1): Retention time: 2.24 min; m / z=425(M+1) + .

[0670] 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) 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 at ambient temperature for 3 hours. After 3 hours, 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 at 65° C. for 3 hours. 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 resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and heptane to give the title compound as a solid (0.45 g). HPLC / MS (Method 1): Retention time: 2.29 min; m / z=699(M) + . 1 H NMR(500MHz,DMSO-d6)δ 10.41(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),4.24(d,J=18.0 Hz,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).

[0671] Example C-112: 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 Step 1: Synthesis of N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline To a stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.0 g) in N,N-dimethylformamide (10 mL) was added methyl iodide (0.777 g) and potassium carbonate (1.262 g) under an inert atmosphere at ambient temperature. The reaction mass was stirred at 50° C. for 18 hours, and the progress of the reaction was monitored by TLC analysis. After the reaction was complete, the reaction mass was diluted with water (20 mL) and then extracted with EtOAc (25 mL×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 give the title compound (1.0 g) as a solid. HPLC / MS (Method 1): Retention time: 2.09 min; m / z=234.3(M+1) + . 1 H NMR(500MHz,DMSO-d6)δ 7.43-7.37(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).

[0672] Step 2: Synthesis of N-[2,4-dimethyl-5-[4-(methylamino)phenyl]pyrazol-3-yl]-4-(trifluoromethoxy)benzamide To a stirred solution of [1,4-dimethyl-5-[[4-(trifluoromethoxy)benzoyl]amino]pyrazol-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-dioxaborolan-2-yl)aniline (0.688 g), tetrakis (0.620 g), and potassium carbonate (0.742 g) under an inert atmosphere at ambient temperature. The reaction mass was stirred at 110°C for 18 hours, and the progress of the reaction was monitored by TLC analysis. After completion of the reaction, 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 column chromatography to give the title compound (1.01 g) as a solid. HPLC / MS (method 1): Retention time: 1.98 min; m / z=405.3(M+1) + . 1 H NMR(300MHz,DMSO-d6)δ 10.29(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).

[0673] Step 3: Synthesis of N-[5-[4-[benzoylcarbamothioyl(methyl)amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide 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) under an inert atmosphere at ambient temperature. The reaction mass was stirred at 50° C. for 19 hours, and the progress of the reaction was monitored by TLC analysis. After completion of the reaction, the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography to give the title compound (1.1 g). HPLC / MS (Method 1): Retention time: 2.08 min; m / z=568.2 (M+1) + .

[0674] Step 4: Synthesis of N-[5-[4-[carbamothioyl(methyl)amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide To a stirred solution of N-[5-[4-[benzoylcarbamothioyl(methyl)amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (1.1 g) in MeOH (11 mL) was added 2N aqueous NaOH solution (13 mL) at ambient temperature. The reaction mass was stirred at 65° C. for 22 hours, and the progress of the reaction was monitored by TLC analysis. After the reaction was completed, the pH of the reaction mass was adjusted to neutral using 2N HCl (5 mL), and then extracted with EtOAc (25 mL×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 give the title compound (0.300 g) as a solid. HPLC / MS (Method 1): Retention time: 1.97 min; m / z=464.2 (M+1) + ; 1 H NMR(500MHz,DMSO-d6)δ 10.38(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).

[0675] Step 5: Synthesis of N-[5-[4-[(4,5-dioxothiazol-2-yl)-methyl-amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide To a stirred solution of N-[5-[4-[carbamothioyl(methyl)amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (0.1 g) in EtOAc (2 mL) was added oxalyl chloride (0.096 g) and triethylamine (0.052 g) under an inert atmosphere at ambient temperature. The reaction mass was stirred at ambient temperature for 15 minutes, and the progress of the reaction was monitored by TLC analysis. After the reaction was complete, the reaction mass was diluted with water (10 mL) and then extracted with DCM (10 mL × 2). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (0.120 g) as a solid. HPLC / MS (Method 1): Retention time: 2.02 min; m / z=517.2(M)-.

[0676] Step 6: Synthesis of N-[5-[4-[(2-isopropyl-5-methyl-phenyl)carbamothioylcarbamoyl-phenyl-amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide To a stirred solution of N-[5-[4-[(4,5-dioxothiazol-2-yl)-methyl-amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (0.140 g) in toluene (2 mL) at ambient temperature, the reaction mass was stirred at 100° C. for 25 minutes. 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 hours, and the progress of the reaction was monitored by TLC analysis. After completion of the reaction, the solvent was concentrated under reduced pressure, and the crude product was purified by flash chromatography to give the title compound (0.04 g) as a solid. HPLC / MS (Method 1): Retention time: 2.39 min; m / z=639.4(M+1) + .

[0677] 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) To a stirred solution of N-[5-[4-[(2-isopropyl-5-methyl-phenyl)carbamothioylcarbamoyl-methyl-amino]phenyl]-2,4-dimethyl-pyrazol-3-yl]-4-(trifluoromethoxy)benzamide (0.040 g) in EtOH (1 mL) was added sodium acetate (0.010 g) and methyl bromoacetate (0.014 g) at ambient temperature. The reaction mass was stirred at 50° C. for 3 hours and monitored by TLC analysis. After completion of the reaction, the reaction mass was diluted with water (5 mL) and then extracted with EtOAc (5 mL×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 give the title compound (0.015 g) as a solid. HPLC / MS (Method 1): Retention time: 2.22 minutes; m / z=679.3(M+1) + ; 1 H NMR(500MHz,DMSO-d6)δ 10.36(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),4.22(d,J=18.0 Hz,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).

[0678] All other examples listed in Table C are synthesized similarly to the methods mentioned in either the general procedures or experimental procedures mentioned above.

[0679] [Table 17]

[0680] Table 18

[0681] Table 19

[0682] Table 20

[0683] Table 21

[0684] Table 22

[0685] Table 23

[0686] Table 24

[0687] Table 25

[0688] Table 26

[0689] Table 27

[0690] [Table 28]

[0691] [Table 29]

[0692] [Table 30]

[0693] [Table 31]

[0694] Biological Examples Example B.1: Activity against Aedes aegypti mosquitoes To evaluate control of Aedes aegypti mosquitoes, test units consisted of 96-well microtiter plates containing 200 μl of tap water and 5–15 newly hatched A. aegypti larvae per well.

[0695] The active compounds or mixtures were formulated using a solution containing 75% (v / v) water and 25% (v / v) DMSO. Various concentrations of the formulated compounds or mixtures were sprayed onto the insect diet in duplicate at 2.5 μL using a custom-made microatomizer.

[0696] For the experimental mixtures in these tests, equal volumes of both mixing partners were mixed together at the desired concentrations.

[0697] After application, the microtiter plates were incubated for 2 days at 28±1° C. and 80±5% relative humidity, after which larval mortality was visually assessed.

[0698] 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-7 6, 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 compared to untreated controls at 800 ppm.

[0699] Example B.2: Activity against orchid thrips (Dichromothrips corbetti) Adult Dichromothrips corbetti insects used in the bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing, test compounds were diluted in a 1:1 mixture of acetone:water (volume:volume) and Kinetic® HV was added at a concentration of 0.01% v / v.

[0700] The thrips efficacy of each compound was assessed using the floral immersion technique. All petals of individual, intact orchid flowers were immersed in the treatment solution and allowed to dry in a Petri dish. Treated petals were placed in individual resealable plastic containers along with approximately 20 adult thrips. All test arenas were maintained under continuous light and at a temperature of approximately 28°C during the assay. After 3 days, the number of surviving thrips on each petal was counted. Mortality was recorded 72 hours after treatment.

[0701] 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-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 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-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 compared to untreated controls at 300 ppm.

[0702] Example B.3: Activity against boll weevil (Anthonomus grandis) To evaluate control of boll weevil (Anthonomus grandis), test units consisted of 96-well microtiter plates containing insect bait and 5-10 A. grandis eggs.

[0703] Compounds were formulated using a solution containing 75% (v / v) water and 25% (v / v) DMSO. Various concentrations of the formulated compounds were sprayed onto the insect diet in duplicate at 5 μl using a custom-made microatomizer.

[0704] After application, the microtiter plates were incubated for 5 days at approximately 25±1° C. and approximately 75±5% relative humidity, and then visually assessed for egg and larval mortality.

[0705] 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, 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-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 compared to untreated controls at 800 ppm.

[0706] Example B.4: Activity against silverleaf whitefly (Bemisia argentifolii) (adult) The active compounds were formulated in 100% cyclohexanone as 10,000 ppm solutions delivered via tube using a Tecan liquid handler. The 10,000 ppm solutions were serially diluted with 100% cyclohexanone to create intermediate solutions. These were used as stock solutions, and final dilutions were made with 50% acetone:50% water (v / v) using a Tecan and placed in 5 or 10 ml glass vials. A nonionic surfactant (Kinetic®) was added to the solution at a concentration of 0.01% (v / v). The vials were then inserted into an automated electrostatic sprayer equipped with a spray nozzle for application to plants / insects.

[0707] Cotton plants at the cotyledon stage (one plant per pot) were sprayed using an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were allowed to dry in the sprayer's fume hood and then removed from the sprayer. Each pot was placed in a plastic cup and approximately 10-12 adult whiteflies (approximately 3-5 days old) were introduced. Insects were collected using a suction device connected to a barrier pipette tip and non-toxic Tygon® tubing. The tip containing the collected insects was then gently inserted into the soil containing the treated plants, allowing the insects to crawl out of the tip and reach the leaves to feed. The cup was covered with a reusable screen lid. The test plants were maintained in a growth room at approximately 25°C and approximately 20-40% relative humidity for three days, avoiding direct exposure to fluorescent lights (24-hour photoperiod) to prevent heat buildup within the cup. Mortality was assessed three days after treatment, compared to untreated control plants.

[0708] 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 compared to untreated controls at 300 ppm.

[0709] Example B.5: Activity against tobacco budworm (Heliothis virescens) To evaluate control of tobacco budworm (Heliothis virescens), test units consisted of 96-well microtiter plates containing insect bait and 15–25 H. virescens eggs.

[0710] Compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO. Various concentrations of formulated compounds were sprayed onto the insect diet in duplicate at 10 μl using a custom-made microatomizer.

[0711] After application, the microtiter plates were incubated for 5 days at approximately 28±1° C. and approximately 80±5% relative humidity, and then visually assessed for egg and larval mortality.

[0712] 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 , 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-8 8, 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- 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 at least 75% mortality compared to untreated controls at 800 ppm.

[0713] Example B.6: Activity against diamondback moth (Plutella xylostella) The active compound is dissolved at the desired concentration in a 1:1 (v / v) mixture of distilled water and acetone. A surfactant (Kinetic® HV) is added at a rate of 0.01% (v / v). The test solution is prepared on the day of use.

[0714] Cabbage leaves were dipped in the test solution and allowed to air dry. Treated leaves were placed in Petri dishes lined with moistened filter paper and inoculated with 10 third-instar larvae. Mortality was recorded 72 hours after treatment. Feeding damage was also recorded using a 0-100% scale.

[0715] 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-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 each showed at least 75% mortality compared to untreated controls at 300 ppm.

[0716] Example B.7: Activity against second instar larvae of the Southern armyworm (Spodoptera eridania) The active compounds were formulated in 100% cyclohexanone as 10,000 ppm solutions delivered via tube using a Tecan liquid handler. The 10,000 ppm solutions were serially diluted with 100% cyclohexanone to create intermediate solutions. These were used as stock solutions, and final dilutions were made with 50% acetone:50% water (v / v) using a Tecan and placed in 10 or 20 ml glass vials. A nonionic surfactant (Kinetic®) was added to the solution at a concentration of 0.01% (v / v). The vials were then inserted into an automated electrostatic sprayer equipped with a spray nozzle for application to plants / insects.

[0717] Lima bean plants (Sieva variety) were grown two per pot 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 allowed to dry in the sprayer fume cupboard and then removed from the sprayer. Each pot was placed in a perforated plastic zip-top bag. Approximately 10-11 armyworm larvae were placed in the bag, and the bag was then resealed. The test plants were maintained in a growth room at approximately 25°C and approximately 20-40% relative humidity for four days, avoiding direct exposure to fluorescent light (24-hour photoperiod) to prevent heat buildup within the bag. Four days after treatment, mortality and feeding reduction were assessed compared to untreated control plants.

[0718] 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-1 8, 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 , 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-103, C-104, C-105, C 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 compared to untreated controls at 300 ppm.

[0719] Example B.8: Activity against diamondback moth (Plutella xylostella) To evaluate control of diamondback moth (Plutella xylostella), test units consisted of 96-well microtiter plates containing insect bait and 15-25 P. xylostella eggs. Compounds or mixtures were formulated using a solution containing 75% water and 25% DMSO. Various concentrations of formulated compounds or mixtures were sprayed onto the insect bait in duplicate at 5 μL using a custom-made microatomizer. For experimental mixtures in these tests, identical volumes of both mixing partners were mixed together at the desired concentrations. After application, the microtiter plates were incubated at 28 ± 1 °C and 80 ± 5% relative humidity for 5 days. Egg and larval mortality was then assessed visually.

[0720] 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 compared to untreated controls at 800 ppm.

[0721] The beneficial activity of the compounds according to the invention compared to structurally related compounds known from the prior art was demonstrated by the following comparative experiments:

[0722] [Table 32]

[0723]

Table 33

Claims

1. Formula I 【Chemical 1】 [In the formula, Q is —C(═O)—N(R ５ ) - or -N(R ５ )-C(=O)-; R ５ is H, C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkyl-C １ ~C ６ Alkoxy, C １ ~C ６ Alkyl-C ３ ~C ６ Cycloalkyl, phenyl, 5- or 6-membered hetaryl, —CH ２ -phenyl, -CH ２ - 5- or 6-membered hetaryl, 1,3-dioxolan-2-ylmethyl, or halogen, wherein the alkyl, cycloalkyl, phenyl, and hetaryl moieties are unsubstituted or substituted with halogen or CN; A is N or CR Ａ and R Ａ is H, C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, halogen, CN, or NR ６ R ７ wherein said alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted with halogen or CN; R ２ is H or C １ ~C ６ Alkyl, or C ３ ~C ６ and cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen, CN, or C. １ ~C ６ substituted with alkoxy; B １ is N or CR Ｂ１ and B ２ is N or CR Ｂ２ and B ３ is N or CR Ｂ３ and B ４ is CR Ｂ４ and R Ｂ１ , R Ｂ２ , R Ｂ３ , and R Ｂ４ are independently H, halogen, CN, C １ ~C ６ Alkyl, C ３ ~C ６ cycloalkyl, or C １ ~C ６ alkoxy, wherein said alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; D is part DA or DB 【Chemistry 2】 and R ３ is H, C １ ~C ６ Alkyl, or C ３ ~C ６ cycloalkyl, wherein said alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN; R ４ is H, C １ ~C ６ Alkyl, or C ３ ~C ６ and cycloalkyl, wherein the alkyl and cycloalkyl moieties are unsubstituted or halogen, —O—(C═O)—C １ ~C ６ Alkoxy, —O—(C═O)—C １ ~C ６ substituted with alkyl or CN; or B is a 5- or 6-membered carbocyclic group, and one or two CH ２ The moiety may be substituted with a carbonyl group, O, or S, and the carbocyclic group may be unsubstituted or ｈ is substituted with; Ar １ is phenyl or 5- or 6-membered heteroaryl, unsubstituted or Ａｒ１ where: R Ａｒ１ is halogen, SF ５ , NO ２ , OH, CN, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Heterocyclyl, C ３ ~C ６ Cycloalkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C ３ ~C ６ Heterocyclyl and cycloalkoxy moieties may be unsubstituted or R ｆ , C(═O)—OR ａ , N.R. ｂ R ｃ , C １ ~C ６ 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)-(C １ ~C ６ alkyl) ２ , or SO ２ NR ｂ R ｃ is substituted with; R ６ and R ７ are the same or different, H, C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, phenyl, —CH ２ -phenyl, 5- or 6-membered heteroaryl, -CH ２ - 5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl, or 2-(methylamino)-2-oxo-ethyl, wherein the alkyl, cycloalkyl, phenyl, and heteroaryl moieties are unsubstituted or substituted with halogen, CN, C １ ~C ６ Alkyl or C １ ~C ６ substituted with alkoxy; Ar ２ is phenyl or 5- or 6-membered heteroaryl, unsubstituted or Ａｒ２ where: R Ａｒ２ is halogen, CN, -SCN, SF ５ , C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy-C １ ~C ４ Alkyl, C １ ~C ６ Alkoxy-C １ ~C ４ Alkoxy, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Cycloalkoxy, C ３ ~C ６ Cycloalkyl-C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkoxy-C １ ~C ４ alkyl, wherein the alkyl, alkoxy, alkenyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or halogen or CN; C(═O)—OR ａ , N.R. ｂ R ｃ , C １ ~C ６ Alkylene-CN, C(=O)-NR ｂ R ｃ is substituted with; R ａ , R ｂ and R ｃ are the same or different, H, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Cycloalkyl-C １ ~C ４ Alkyl, —C(═O)—C １ ~C ６ alkyl, wherein said alkyl, alkenyl and cycloalkyl moieties are unsubstituted or substituted with halogen; R ｄ is H or C １ ~C ６ is alkyl; R ｅ is C １ ~C ６ Alkyl or C ３ ~C ６ cycloalkyl, wherein said alkyl, cycloalkyl moiety is unsubstituted or substituted with halogen; m is 0, 1 or 2; R ｆ is halogen, OH, CN, SCN, SF ５ , C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy-C １ ~C ４ Alkyl, C １ ~C ６ Alkoxy-C １ ~C ４ Alkoxy, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Cycloalkoxy, C ３ ~C ６ Cycloalkyl-C １ ~C ４ Alkyl, or C ３ ~C ６ Cycloalkoxy-C １ ~C ４ alkyl, wherein said alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and cycloalkoxy moieties are unsubstituted or substituted with halogen; R ｈ is a halogen, C １ ~C ６ Alkyl, or C １ ~C ６ is an alkoxy group. and N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

2. 2. The compound of formula I according to claim 1, wherein D is DB.

3. D is a group selected from the moieties D5 to D7, which is unsubstituted or contains one or two substituents R ｈ 2. The compound of formula I according to claim 1, substituted with: 【Chemistry 3】

4. 2. The 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. 【Chemistry 4】

5. A compound of formula I according to any one of claims 1 to 4, wherein R ５ is H, C １ ~C ６ Alkyl, or C １ ~C ６ alkyl-CN; R Ａ is H, CN, or C １ ~C ６ Alkyl; R ２ is H or C １ ~C ６ The compound of formula I, wherein:

6. In the formula, B １ is CR Ｂ１ and B ２ is CR Ｂ２ and B ３ is CR Ｂ３ 6. A compound of formula I according to any one of claims 1 to 5, wherein

7. In the formula, B １ is N and B ２ is CR Ｂ２ and B ３ is CR Ｂ３ 6. A compound of formula I according to any one of claims 1 to 5, wherein

8. Compounds of formula I according to any one of claims 1 to 7, wherein R Ｂ１ , R Ｂ２ , R Ｂ３ , and R Ｂ４ are independently H, halogen, CN, C １ ~C ６ Alkyl, C ３ ~C ６ cycloalkyl, or C １ ~C ６ A compound of formula I wherein the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen.

9. A compound of formula I according to any one of claims 1 to 8, wherein Ar １ is phenyl, unsubstituted or R Ａｒ１ is substituted with; R Ａｒ１ is halogen, SF ５ , NO ２ , OH, CN, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Heterocyclyl, C ３ ~C ６ Cycloalkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C ３ ~C ６ Heterocyclyl and cycloalkoxy moieties may be unsubstituted or R ｆ , C(═O)—OR ａ , N.R. ｂ R ｃ , C １ ~C ６ Alkylene-CN, C(=O)-NR ｂ R ｃ , C(=O)-R ｄ , NHS(=O) ｍ R ｅ , -N=S(=O)-(C １ ~C ６ alkyl) ２ , S.O. ２ NR ｂ R ｃ , or S(=O) ｍ R ｅ is substituted with; R ａ , R ｂ and R ｃ are the same or different, H, C １ ~C ６ alkyl, unsubstituted or substituted with halogen; R ｄ is H or C １ ~C ６ is alkyl; R ｅ is C １ ~C ６ Alkyl or C １ ~C ６ haloalkyl; R ｆ is halogen, OH, CN, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ cycloalkoxy, unsubstituted or substituted with halogen; A compound of formula I wherein m is 0, 1 or 2.

10. A composition comprising one compound of formula I according to any one of claims 1 to 9, an N-oxide or an agriculturally acceptable salt thereof, and a further active substance.

11. 11. A method for combating or controlling invertebrate pests, comprising contacting the pests or their food sources, habitats or breeding sites with a pesticidally effective amount of at least one compound of any one of claims 1 to 9 or the composition of claim 10.

12. 11. A method for protecting cultivated plants from infestation or infestation by invertebrate pests, comprising contacting the plants, or the soil or water in which the plants are grown, with a pesticidally effective amount of at least one compound of any one of claims 1 to 9 or the composition of claim 10.

13. Seeds comprising a compound according to any one of claims 1 to 9, or an enantiomer, diastereomer or salt thereof, in an amount of 0.1 g to 10 kg per 100 kg of seeds, or a composition according to claim 10.

14. 11. Use of a compound of formula I as defined in any one of claims 1 to 9, and an agriculturally acceptable salt thereof, or a composition as defined in claim 10, for protecting plants in cultivation from infestation or infestation by invertebrate pests.

15. 10. A method for treating or protecting an animal from infestation or infection by an invertebrate pest, comprising contacting said 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.

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