Pirazolide pest-killing compounds

Abstract

The present invention relates to compounds of formula (I), and their N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts, wherein the variables are defined as described herein. The compounds of formula (I), and their N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts, are useful for combating or controlling invertebrate pests, particularly arthropod pests and nematodes. The present invention also relates to methods for controlling invertebrate pests by using these compounds, as well as plant propagation materials and agricultural and veterinary compositions comprising the compounds. [Formula 1] TIFF2025525848000072.tif20170

Description

[Background technology]

[0001] Invertebrate pests, particularly insects, arachnids, and nematodes, destroy growing and harvested crops and attack wooden residential and commercial buildings, thereby causing significant economic loss to food supplies and property. Thus, there is a continuing need for new agents to control invertebrate pests.

[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.

[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, particularly difficult-to-control insects, arachnids, and nematodes. Summary of the Invention [Problem to be solved by the invention]

[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, in particular 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-C3-alkoxy or C1-C6-alkyl-C6-C6-cycloalkyl, phenyl, 5- or 6-membered heteroaryl, -CH2-phenyl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or halogen, in which the alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted with halogen; R 1 is H, C1-C6-alkyl, C3-C6-cycloalkyl, halogen, or NR 6 R 7 wherein the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN; R 2 is H, C1-C6-alkyl, C3-C6-cycloalkyl, or halogen, where the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN; B 1 is N or CR B1 and; B 2 is N or CR B2 and; B 3 is N or CRB3 and; B 4 is CR B4 and; R B1 , R B2 , R B3 , and R B4 are, independently of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; D is the moiety DA or DB, [ka] R 3 is H, C1-C6-alkyl or C3-C6-cycloalkyl, where the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN; R 4 is H, C1-C6-alkyl or C3-C6-cycloalkyl, where the alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkyl, -O-(C=O)-C1-C6-alkoxy or CN; B is a 5- or 6-membered carbocyclic group, in which one or two CH moieties of the carbocyclic group may be replaced by a carbonyl group, O, or S, and the carbocyclic group is unsubstituted or is selected from the group consisting of R h is replaced by; Ar 1 is phenyl or 5- or 6-membered heteroaryl, which is 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, where the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C-C-heterocyclyl, and cycloalkoxy moieties are unsubstituted or are substituted by R 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, SO2NR b R c , or S(=O) m R e is replaced by; R 6 and R 7 are identical 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, in which the alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN, C1-C6-alkyl or C1-C6-alkoxy; Ar 2 is phenyl or 5- or 6-membered heteroaryl, which is unsubstituted or Ar2 where: R Ar2is 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, in which the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or halogen; 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 identical 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, in which the alkyl, alkenyl and cycloalkyl moieties are unsubstituted or substituted by halogen; R d is H, C1-C6-alkyl; R e is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, where the alkyl, cycloalkyl moiety is unsubstituted or substituted with halogen or CN; R fis 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, C3-C6-cycloalkoxy-C1-C4-alkyl, in which the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted by halogen; R h is halogen, C1-C6-alkyl or C1-C6-alkoxy; m is 0, 1 or 2 and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

[0007] The present invention further relates to processes and intermediates for preparing the compounds of formula I, as well as active compound combinations comprising them. Furthermore, the present invention relates to agricultural or veterinary compositions comprising the compounds of formula I, and 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 growing plants from attack and / or infestation by invertebrate pests. The present invention also relates to a method for applying the compounds of formula I. The present invention also relates to a method for protecting crops, plants, plant propagation material, and / or growing plants from attack or infestation by invertebrate pests, comprising contacting or treating crops, plants, plant propagation material, and growing plants, or the soil, material, surface, space, area, or water in which crops, plants, plant propagation material, or plants are stored or growing, 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, which includes N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

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

[0010] General steps: Compounds of formula (I) can be prepared by methods of organic chemistry, for example, by the methods described herein later in Schemes 1-19 in the synthetic description of the Examples. In Schemes 1-19, the group Ar 1 , B 1 , B 2 , B 3 , B 4 , Q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R h and Ar 2 is as defined above with respect to formula (I) unless otherwise specified. [ka] In the formula, D is [ka] Either:

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

[0012] In one embodiment of Scheme 1, a compound of formula (E1) is reacted directly with a compound of formula (Ia-2) in the presence of an inorganic base to form a compound of formula (Ia). The isocyanate compound of formula (Ia-2) can be prepared as described in March's Advanced Organic Chemistry 6 th As described in the above edition by Michael B. Smith and Jerry March, it can be generated in situ from amines of formula (Ia-1) by using one of the common reagents such as phosgene, diphosgene, triphosgene, or carbonyldiimidazole (Step I) in the presence of a base in a mixed solvent system.

[0013] According to another embodiment of Scheme 1, isocyanate compounds of formula (Ia-2) are produced via Curtius rearrangement of acyl azides (Ia-4), for example, by methods similar to those described in WO 2014 / 204622. The acyl azides 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 with diphenylphosphoryl azide in the presence of an amine base such as triethylamine.

[0014] The compounds of formula (I), formula (Ia) can also be prepared by methods similar to those described in WO 2021 / 011722 or Scheme 2. Scheme 2: [ka]

[0015] According to the method shown 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 produce the activated amine (Ia-1′), which can then be reacted with a compound of formula (E1) in the presence of an organic base such as N,N-diisopropylethylamine to form a compound of formula (Ia). Compounds of formula (E1) can be prepared by methods similar to those described in WO 2021 / 011722.

[0016] Scheme 3: [ka] As shown in Scheme 3, a compound of formula (E1) can be treated with an activating agent such as 4-nitrophenyl chloroformate in the presence of a polar aprotic solvent, preferably tetrahydrofuran, and an inorganic base such as cesium carbonate or potassium carbonate to generate an activated carbamate intermediate (E1-1), which can then be reacted with an amine of formula (Ia-1) in the presence of an inorganic base such as cesium carbonate or potassium carbonate to form a compound of formula (Ia).

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

[0018] As shown in Scheme 4, compounds of formula (Ia') can be prepared by treating an aryl thiourea of formula (E1') with an isocyanate of formula (Ia-2) in the presence of an inorganic base such as cesium carbonate or sodium hydride in an aprotic solvent. Compounds of formula (E1') can be prepared by methods similar to those described in WO 2021 / 011722.

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

[0020] In the above reaction, the compound of formula (E1-Ia) can be converted into various cyclic 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 shown in J. of Med. Chem. 2010, 53(10), 4198-4211. Compounds of formula (E1-IIIa) and (E1-IVa) can be prepared by treating compounds of formula (E1-Ia) with unsubstituted, mono- or disubstituted 2-chloroacetyl chloride and 3-chloropropanoyl chloride in two steps, as described in J. of 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) 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 methods similar to those described in WO 2021 / 011722 or Scheme 6. Scheme 6: [ka]

[0022] In the above reaction, compounds of formula (Ia') can be converted to various cyclic analogs of formulas (Ia-I), (Ia-II), (Ia-III) and (Ia-IV). Cyclization can be achieved by treating compounds of formula (Ia') with an α-haloester such as methyl bromoacetate or methyl bromopropanoate to form unsubstituted or R h This can be achieved by forming compounds of formula (Ia-I) and (Ia-II) mono- or di-substituted with R h 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. Steps XVIII and XIX preferably use sodium acetate in a protic solvent such as ethanol at a temperature ranging from about 20°C to about 70°C. Steps XX and XXI preferably use an inorganic base such as potassium carbonate in a solvent such as acetonitrile or 2-butanone at a temperature ranging from about 0°C to about 80°C. All of the above reactions can be carried out by methods similar to those described in WO 2021 / 011722.

[0023] Compounds of formula (Ia-1) can be prepared by methods similar to those described in Scheme 7. Scheme 7: [ka]

[0024] As shown in Scheme 7, compounds of formula (Ia-1) can be prepared by different synthetic routes. Step XXII can be carried out via a Chan-Lam coupling reaction starting from an arylboronic acid precursor (1), as described in Chem.A Eur.J., 2017, 23(14), 3285-3290.

[0025] Alternatively, compounds of formula (Ia-1) can be prepared by reduction of nitro compounds of formula (IIIa-1) using a reducing agent such as SnCl in acidic medium, as shown in Step XXIII.

[0026] 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 a salt thereof, preferably copper or a salt thereof, as described in Chem. Commun., 2009, 3035-3037.

[0027] Additionally, compounds of formula (Ia-1) can also be prepared in two steps from compounds of formula (IVa-1). In step XXV, 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), followed in step XXVI by Boc deprotection using trifluoroacetic acid or dilute hydrochloric acid to form the desired compounds. All of these reactions are described in March's Advanced Organic Chemistry 6 th The procedure is carried out as described in the "Synthetic Electrophoresis of Electrophoresis" edition, Michael B. Smith and Jerry March.

[0028] Compounds of formula (IIIa-1) can be prepared by methods similar to those described in Scheme 8. Scheme 8: [ka]

[0029] Step XXVII involves the SNAr reaction between pyrazole (IIa) and p-fluoronitroarene (2), as described in WO 2017 / 139274. Step XXVIII can be carried out via a Chan-Lam coupling reaction starting from arylboronic acid precursor (3), as described in Chem.A Eur.J., 2017, 23(14), 3285-3290.

[0030] Compounds of formula (IVa-1) can be prepared by methods similar to those described in Scheme 9. Scheme 9: [ka]

[0031] Step XXIX can be carried out via a Chan-Lam coupling reaction starting from the arylboronic acid precursor (4), as described in Chem.A Eur.J., 2017, 23(14), 3285-3290. Hal is preferred as the bromide.

[0032] Q is -C(=O)-N(R 5 )- and R 1 is C1-C6-alkyl or C3-C6-cycloalkyl, and R 5 Compounds of formula (IVa-1) where is H are compounds of formula (IVa-1-1) and can be prepared by methods similar to those described in Scheme 10. Scheme 10: [ka]

[0033] As depicted in Scheme 10, compounds of formula (IVa-1-1a) can be prepared from commercially available 1,3-diketone derivatives (5) by reacting them with substituted arylhydrazines (ArNHNH, 6), as described in WO 2016 / 044666. Compounds of formula (IVa-1-1b) can then be produced by nitrating compounds of formula (IVa-1-1a) using a mixture of nitric acid and sulfuric acid in an aprotic solvent such as dichloroethane. Compounds of formula (IVa-1-1b) can then be reduced to compounds of formula (IVa-1-1c) using a reducing agent such as SnCl in an acidic medium or Fe with NHCl in a mixture of ethanol and water, as shown in Step XXXII. The reaction can then be carried out as described in March's Advanced Organic Chemistry 6. th Compounds of formula (IVa-1-1) can be formed by an amide coupling reaction of compounds of formula (IVa-1-1c) with derivatives of benzoic acid using a suitable coupling reagent such as HATU or T3P and a base such as DIPEA, as described in Michael B. Smith and Jerry March, Advanced Organic Chemistry 6, ed., Michael B. Smith and Jerry March. Compounds of formula (IVa-1-1) can also be formed by an amide coupling reaction of compounds of formula (IVa-1-1c) with derivatives of benzoic acid using a suitable coupling reagent such as HATU or T3P and a base such as DIPEA, as described in Michael B. Smith and Jerry March, Advanced Organic Chemistry 6, ed., ... th The compound of formula (IVa-1-1c) can be synthesized by treating the compound of formula (IVa-1-1c) with commercially available benzoyl chloride in the presence of a base, as described in the "Advanced Organic Chemistry" vol. 6, by Michael B. Smith and Jerry March. The compound of formula (IVa-1-1) can also be synthesized by treating the compound of formula (IVa-1-1c) with commercially available benzoyl chloride in the presence of a base, as described in the "Advanced Organic Chemistry" vol. 6, by Michael B. Smith and Jerry March. th As described in the "Comparative Example 1," Michael B. Smith and Jerry March, edition, the benzoyl chloride can be generated in situ from the corresponding benzoic acid using POCl or SOCl, followed by treatment with a compound of formula (IVa-1-1c) in the presence of a base.

[0034] Q is -N(R5 )-C(=O)-, and R 1 is C1-C6-alkyl or C3-C6-cycloalkyl, and R 5 Compounds of formula (IVa-1) where is H are compounds of formula (IVa-1-2) and can be prepared by methods similar to those described in Scheme 11. Scheme 11: [ka]

[0035] The compound of formula (IVa-1-2b) can be prepared in two steps starting from the commercially available beta-ketoester derivative (7) via the intermediate of formula (IVa-1-2a), as described in Synthesis, 2019, 51(6), 1473-1481. Step XXXV involves pyrazole synthesis, as described in Angew., Chem., Int. Ed., 2010, 49(42), 7790-7794. Step XXXVI involves hydrolysis of the ester using a suitable base, such as LiOH or NaOH, as described in WO 2011 / 050245. Step XXXVII involves hydrolysis of the ester using a suitable base, such as LiOH or NaOH, as described in March's Advanced Organic Chemistry 6 th These include amide coupling reactions with aniline derivatives using a suitable coupling reagent such as HATU or T3P and a base such as DIPEA, similar to those described in the "Synthetic Chemistry of Aromatic Synthesis" series, Michael B. Smith and Jerry March, ed., 1999.

[0036] Q is -C(=O)-N(R 5 )- and R 1 NR 6 R 7 and R 5 Compounds of formula (IVa-1) where is H are compounds of formula (IVa-1-3) which can be prepared by methods similar to those described in Scheme 12. Scheme 12: [ka]

[0037] Compounds of formula (IVa-1-3a) can be prepared by reacting commercially available beta-ketoester derivatives (7') with substituted arylhydrazines (ArNHNH2, 6) as described in J. of Het. Chem. 1984, 21(6), 1747-52. Compounds of formula (IVa-1-3b) can be prepared from compounds of formula (IVa-1-3a) by treatment with POCl3. Nitration of compounds of formula (IVa-1-3b) can then be carried out as described in Bioorg. and Med. Chem. 2014, 22(9), 2739-2752 to produce compounds of formula (IVa-1-3c). R 7 or R 6 Amination of compounds of formula (IVa-1-3c) where R 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 2-(methylamino)-2-oxo-ethyl can be prepared by reacting with the corresponding commercially available alkylamine or benzylamine in the presence of a base such as TEA and a polar aprotic solvent such as DMF to give compounds of formula (IVa-1-3d). 7 or R 6 Compounds of formula (IVa-1-3d) where R is phenyl or 5- or 6-membered hetaryl can be prepared from compounds of formula (IVa-1-3c) by metal-catalyzed reaction with the corresponding aniline, as described in U.S. Patent Application Publication No. 20080036373. 7 or R 6Compounds of formula (IVa-1-3d), where is H, can be prepared from compounds of formula (IVa-1-3c) 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. Compounds of formula (IVa-1-3d) can be reduced to compounds of formula (IVa-1-3e) using a reducing agent such as SnCl in acidic medium or Fe with NH4Cl in a mixture of ethanol and water, as shown in step XLII. Finally, compounds of formula (IVa-1-3) can be reduced to compounds of formula (IVa-1-3e) using a reducing agent such as SnCl in acidic medium or Fe with NH4Cl in a mixture of ethanol and water, as described in March's Advanced Organic Chemistry 6 th The compound of formula (IVa-1-3e) can be prepared by the amide coupling reaction of a compound of formula (IVa-1-3e) with a derivative of benzoic acid using a suitable coupling reagent such as HATU or T3P and a base such as DIPEA, as described in Michael B. Smith and Jerry March, Advanced Organic Chemistry, Vol. 6, No. 1, pp. 117-122, 1997. The compound of formula (IVa-1-3) can also be prepared by the amide coupling reaction of a compound of formula (IVa-1-3e) with a derivative of benzoic acid using a suitable coupling reagent such as HATU or T3P and a base such as DIPEA, as described in Michael B. Smith and Jerry March, Advanced Organic Chemistry, Vol. 6, No. 1, 1997. th Compounds of formula (IVa-1-3e) can be synthesized by treating the compound of formula (IVa-1-3e) with commercially available benzoyl chloride in the presence of a base, as described in the "Advanced Organic Chemistry" series, Vol. 6, No. 1, pp. 117-120, by Michael B. Smith and Jerry March. Compounds of formula (IVa-1-3) can also be synthesized by treating the compound of formula (IVa-1-3e) with commercially available benzoyl chloride in the presence of a base, as described in the "Advanced Organic Chemistry" series, Vol. 6, No. 1, pp. 117-120, by Michael B. Smith and Jerry March. th As described in the "Comparative Synthesis of Benzoyl Chlorides of the Invention" (ed.), Michael B. Smith and Jerry March, in situ generation of benzoyl chlorides from the corresponding benzoic acids using POCl or SOCl, followed by treatment with a compound of formula (IVa-1-3e) in the presence of a base, can be synthesized.

[0038] Q is -N(R 5 )-C(=O)-, and R 1 NR 6 R 7 and R 5Compounds of formula (IVa-1) where is H are compounds of formula (IVa-1-4) and can be prepared by methods similar to those described in Scheme 13. Scheme 13: [ka]

[0039] Compounds of formula (IVa-1-4a) can be prepared from compounds of formula (IVa-1-3a) by methods similar to those shown in J. of Med. Chem. 2020, 63(19), 11215-11234. The aldehyde is then oxidized to an acid using an oxidizing agent such as KMnO4 to produce compounds of formula (IVa-1-4b), which can undergo amination to give compounds of formula (IVa-1-4c), as described in Scheme 12. Finally, compounds of formula (IVa-1-4c) can be prepared by methods similar to those shown in J. of Med. Chem. 2020, 63(19), 11215-11234. th Compounds of formula (IVa-1-4) can be reacted with aniline derivatives using a suitable coupling reagent such as HATU or T3P and a base such as DIPEA, similar to that described in the above edition by Michael B. Smith and Jerry March, to give compounds of formula (IVa-1-4).

[0040] Q is -C(=O)-N(R 5 )- and R 5 Compounds of formula (IIa) where is H are compounds of formula (IIa-1-1) and can be prepared by methods similar to those described in Scheme 14. Scheme 14: [ka]

[0041] As shown in Scheme 14, compounds of formula (IIa-1-1) can be prepared in two steps from compounds of formula (IIa-1-1a). Step XLVIII involves the reduction of the nitro compound of formula (IIa-1-1a) using a reducing agent such as SnCl in acidic medium or Fe with NH4Cl in a mixture of ethanol and water, and Step XLIX involves the reduction of the nitro compound of formula (IIa-1-1a) using a reducing agent such as SnCl in acidic medium or Fe with NH4Cl in a mixture of ethanol and water, as described in March's Advanced Organic Chemistry 6 th These include amide coupling reactions similar to derivatives of benzoic acid using a suitable coupling reagent such as HATU or T3P and a base such as DIPEA, as described in the "Synthetic Chemistry of Benzyl Alcohols," vol. 1, pp. 111-114, by Michael B. Smith and Jerry March.

[0042] Q is -N(R 5 )-C(=O)-, and R 5 Compounds of formula (IIa) where is H are compounds of formula (IIa-1-2) and can be prepared by methods similar to those described in Scheme 15. Scheme 15: [ka]

[0043] In the above reaction, the compound of formula (IIa-1-2) can be prepared from the compound of formula (IIa-1-2a) in two steps. Step L involves hydrolysis of the ester using a suitable base such as LiOH or NaOH, as described in WO 2011 / 050245. Step LI involves hydrolysis of the ester using a suitable base such as LiOH or NaOH, as described in March's Advanced Organic Chemistry 6 th This includes amide coupling reactions with aniline derivatives using a suitable coupling reagent such as HATU or T3P and a base such as DIPEA, similar to those described in the "Synthetic Chemistry of Aromatic Compounds" by Michael B. Smith and Jerry March, ed., 1999.

[0044] Q is -C(=O)-N(R 5 )- and R5 Compounds of formula (Ia-1), wherein 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), which can be prepared by methods similar to those described in Scheme 16. Scheme 16: [ka]

[0045] The compound of formula (Ia-1-1) is prepared by the method described in March's Advanced Organic Chemistry 6 th edition, Michael B. Smith and Jerry March, as well as those presented in R 5 R can be prepared from a compound of formula (Ia-1-1a) in which R is C1-C6-alkyl or C3-C6-cycloalkyl or -CH2-phenyl or -CH2-5- or 6-membered hetaryl or 1,3-dioxolan-2-ylmethyl by reacting with the corresponding commercially available alkyl halide or benzyl halide, preferably iodide or bromide, in the presence of a base such as cesium carbonate and a polar aprotic solvent such as DMF. 5 Compounds of formula (Ia-1-1), where R is phenyl or 5- or 6-membered hetaryl, 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 iodide or bromide, as described in Chinese J. of 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 LIII can be carried out similarly to step LII. Step LIV involves reduction using a reducing agent such as SnCl in an acidic medium or Fe with NH4Cl in a mixture of ethanol.

[0046] 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 by methods similar to those described in Scheme 17. Scheme 17: [ka]

[0047] Compounds of formula (Ia-1-2) can be prepared from compounds of formula (Ia-1-2a) or from compounds of formula (IIIa-1-2a) using the reaction conditions discussed in Scheme 16.

[0048] R 1 is C1-C6-alkyl or C3-C6-cycloalkyl, and B 2 or B 3 is CR B2 or CR B3 and R B2 or R B3 Compounds of formula (Ia-1) where is Hal are compounds of formula (Ia-1-3) and can be prepared by methods analogous to those described in Scheme 18. Scheme 18: [ka]

[0049] The compound of formula (Ia-1-3) is prepared by the method described in March's Advanced Organic Chemistry 6 thIt can be prepared by treating a compound of formula (Ia-1-3a) with an electrophilic halogenating agent, such as NCS, in a polar aprotic solvent, such as ACN, similar to that described in the above book, Michael B. Smith and Jerry March.

[0050] R 1 Compounds of formula (Ia-I) where is Hal are compounds of formula (Ia-I-1) and can be prepared by methods analogous to those described in Scheme 19. Scheme 19: [ka]

[0051] Compounds of formula (Ia-I-1) can be prepared by treating compounds of formula (Ia-I) with an electrophilic halogenating agent, such as Palau'Chlor, in a non-polar aprotic solvent, such as chloroform, similar to that described in J. Am. Chem. Soc. 2014, 136, 6908-6911.

[0052] Individual compounds of formula I can also be prepared by derivatization of other compounds of formula I or their intermediates.

[0053] When a mixture of isomers is obtained by synthesis, separation is generally not necessary, since in some cases the individual isomers can be interconverted during workup for use or during application (e.g., under the action of light, acid, or base). Such conversions can also occur after use, for example, during plant treatment in treated plants, or within the harmful fungi to be controlled.

[0054] Those skilled in the art will readily understand that the preferences for substituents, in particular those shown in the table below for each substituent, indicated herein in connection with compound I, also 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.

[0055] Unless otherwise indicated, the term "compound according to the invention" or "compound of the invention" or "compound of formula (I)" means The compound of formula I is shown.

[0056] The term "compound according to the invention" or "compound of formula I" includes compounds as defined herein, as well as stereoisomers, salts, tautomers, or N-oxides thereof. The term "compound of the invention" should be understood to be equivalent to the term "compound according to the invention," and therefore also includes stereoisomers, salts, tautomers, or N-oxides thereof.

[0057] The term "composition according to the invention" or "composition of the invention" encompasses any composition 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.

[0058] Depending on the substitution pattern, the compounds according to the present invention may have one or more centers of chirality, in which 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, and mixtures thereof.

[0059] The compounds according to the invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties, such as stability, or may exhibit 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.

[0060] The term "tautomer" includes isomers derived from the compounds of formula I by shifting of an H atom involving at least one H atom located at a nitrogen, oxygen, or sulfur atom. Examples of tautomers are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms, etc.

[0061] 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).

[0062] 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. One center of chirality is the group R 1 are carbon ring atoms of an isothiazolinone ring having the formula: The present invention provides both the pure enantiomers or diastereomers and mixtures thereof, as well as the use according to the invention of the pure enantiomers or diastereomers of compound I or mixtures thereof. Suitable compounds of formula I also include all possible geometric stereoisomers (cis / trans isomers) and mixtures thereof.

[0063] The term N-oxide relates to a form of compound I in which at least one nitrogen atom is present in oxidized form (as NO). More precisely, it relates to any compound of the invention having at least one tertiary nitrogen atom oxidized to an N-oxide moiety. The N-oxide of compound I is in particular a tertiary nitrogen atom oxidized to an N-oxide moiety, for example, Ar or R 11 The compounds of the present invention can be prepared by oxidizing the ring nitrogen atoms of N-heterocycles present in the compound, such as pyridine or pyrimidine rings, 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 which position the compounds of the present invention can form N-oxides.

[0064] Salts of compounds of formula I are preferably agriculturally and veterinarily acceptable salts, which can be formed in the usual manner, for example, if a compound of formula I has a basic functional group, by reacting the compound with an acid of the anion, or by reacting an acidic compound of formula I with a suitable base.

[0065] Suitable agriculturally or veterinarily acceptable salts are, in particular, salts of those cations or acid addition salts of acids whose cations and anions are known and accepted in the art for forming salts for agricultural or veterinary use, respectively, and which do not adversely affect the action of the compounds according to the invention. Suitable cations are, in particular, ions of alkali metals, preferably lithium, sodium and potassium, alkaline earth metals, preferably calcium, magnesium and barium, and transition metals, preferably manganese, copper, zinc and iron, and ammonium (NH + ) and substituted ammonium ions in which one to four 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 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. Suitable veterinarily acceptable acid addition salts, such as salts formed by compounds of formula I containing a basic nitrogen atom, e.g., an amino group, include salts with inorganic acids, such as the 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.

[0066] 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 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.

[0067] The term "invertebrate pests", as used herein, includes animal populations such as insects, arachnids and nematodes that attack plants and can thereby cause substantial damage to the attacked plants, as well as ectoparasites that parasitize animals, particularly warm-blooded animals such as mammals or birds, or other higher animals such as reptiles, amphibians or fish, and can thereby cause substantial damage to the parasitized animal.

[0068] The term "plant propagation material" is understood to refer to all reproductive parts of plants, such as seeds, as well as viable plant material, such as cuttings and tubers (e.g., potatoes), that can be used for plant propagation. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts, and other parts of plants, including seedlings and seedlings that will be transplanted after germination or emergence from the soil. This plant propagation material may be prophylactically treated with a plant protection compound either at the time of or before planting or transplanting. The seedlings may also be protected before transplanting by total or local treatment by immersion or injection.

[0069] The term "plant" includes any kind of plant, including "modified plants," especially "cultivated plants."

[0070] The term "modified plant" refers to any wild-type or related species or genera of cultivated plants.

[0071] The term "cultivated plants" should be understood to include plants that have been modified by breeding, mutagenesis, or genetic engineering, including, but not limited to, agricultural biotechnology products on the market or in development (see http: / / www.bio.org / speeches / pubs / er / agri_products.asp). Transgenic plants are plants whose genetic material has been modified through the use of recombinant DNA technology and is not readily obtainable by breeding, mutation, or natural recombination in its natural environment. Typically, one or more genes have been incorporated into the genetic material of a transgenic plant to improve specific plant characteristics. Such genetic modifications also include, but are not limited to, targeted post-translational modifications of proteins, oligonucleotides, or polypeptides, for example, by glycosylation or polymer addition, such as prenylation, acetylation, or farnesylation moieties, or PEG moieties.

[0072] Plants that have been modified by breeding, mutagenesis, or genetic engineering have been made tolerant to certain types of herbicides, for example, as a result of conventional breeding methods or genetic engineering, such as auxin herbicides such as dicamba or 2,4-D; bleach herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonylureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl-CoA carboxylase (ACCase) inhibitors; or oxynil (i.e., bromoxynil or ioxynil) herbicides. Furthermore, plants have been engineered to tolerate multiple herbicides through multiple genetic modifications, such as tolerance to both glyphosate and glufosinate, or tolerance to both glyphosate and another type of herbicide, such as an ALS inhibitor, HPPD inhibitor, auxin herbicide, or ACCase inhibitor. These herbicide tolerance techniques are described, for example, in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185; and references therein. Some cultivated plants have been made tolerant to herbicides by conventional breeding methods (mutagenesis), such as Clearfield® summer rapeseed (Canola, BASF SE, Germany), which is tolerant to imidazolinones such as imazamox, or ExpressSun® sunflower (DuPont, USA), which is tolerant to sulfonylureas such as tribenuron.Genetic engineering methods have been used to make cultivated plants such as soybean, cotton, corn, beet, and rapeseed tolerant to herbicides such as glyphosate and glufosinate, and some of these cultivated plants are commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, USA), Cultivance® (imidazolinone-tolerant, BASF SE, Germany), and LibertyLink® (glufosinate-tolerant, Bayer CropScience, Germany).

[0073] Furthermore, by using recombinant DNA techniques, it is possible to produce one or more insecticidal proteins, in particular known insecticidal proteins from Bacillus bacteria, in particular from Bacillus thuringiensis, such as delta-endotoxins, e.g., CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; plant insecticidal proteins (VIPs), e.g., VIP1, VIP2, VIP3 or VIP3A; bacterial-colonizing nematodes, e.g., Photorhabdus spp. or Xenorhabdus spp. insecticidal proteins of Pseudomonas spp.; toxins produced by animals, such as scorpion toxins, spider toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, or papain inhibitors; ribosome-inactivating proteins (RIPs), such as ricin, maize-RIP, abrin, rufin, saponins, Also included are plants capable of synthesizing phosphorus or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyltransferase, cholesterol oxidase, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinase or glucanase. In the context of the present invention, these insecticidal proteins or toxins are also to be understood explicitly as protoxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by novel combinations of protein domains (see, for example, WO 02 / 015701).Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP 374 753, WO 93 / 007278, WO 95 / 34656, EP 427 529, EP 451 878, WO 03 / 18810 and WO 03 / 52073. Methods for producing such genetically modified plants are generally known to those skilled in the art and are described, for example, in the above publications. These insecticidal proteins contained in genetically modified plants confer resistance to pests from all taxa of arthropods, particularly beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and nematodes (Nematoda).Transgenic plants capable of synthesizing one or more insecticidal proteins are described, for example, in the publications mentioned above, some of which are, for example, YieldGard® (a maize variety producing the Cry1Ab toxin), YieldGard® Plus (a maize variety producing the Cry1Ab and Cry3Bb1 toxins), Starlink® (a maize variety producing the Cry9c toxin), Herculex® RW (a maize variety producing Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]), Koshi variety), NuCOTN® 33B (cotton variety that produces Cry1Ac toxin), Bollgard® I (cotton variety that produces Cry1Ac toxin), Bollgard® II (cotton variety that produces Cry1Ac and Cry2Ab2 toxins), VIPCOT® (cotton variety that produces VIP-toxin), NewLeaf® (potato variety that produces Cry3A toxin), Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Syngenta Commercially available varieties include Bt11 (e.g., Agrisure® CB) and Bt176 (corn varieties that produce Cry1Ab toxin and PAT enzyme) from Syngenta Seeds SAS, France, MIR604 (corn varieties that produce a modified form of Cry3A toxin; see WO 03 / 018810) from Syngenta Seeds SAS, France, MON 863 (corn varieties that produce Cry3Bb1 toxin) from Monsanto Europe SA, Belgium, IPC 531 (cotton varieties that produce a modified form of Cry1Ac toxin) from Monsanto Europe SA, Belgium, and 1507 (corn varieties that produce Cry1F toxin and PAT enzyme) from Pioneer Overseas Corporation, Belgium.

[0074] Also encompassed are plants that, using recombinant DNA technology, are capable of synthesizing one or more proteins that increase the resistance or tolerance of such plants to bacterial, viral, or fungal pathogens. Examples of such proteins are so-called "pathogenesis-related proteins" (PR proteins; see, e.g., EP 392 225), plant disease resistance genes (e.g., potato cultivars expressing a resistance gene acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum), or T4-lysozyme (e.g., potato cultivars capable of synthesizing these proteins with increased resistance to bacteria such as fire blight, Erwinia amylovora). Methods for producing such genetically modified plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above.

[0075] Also included are plants that are capable, through the use of recombinant DNA technology, of synthesizing one or more proteins that increase the productivity of those plants (e.g., biomass production, grain yield, starch content, oil content or protein content), resistance to drought, salinity or other growth-limiting environmental factors, or resistance to pests and fungal, bacterial or viral pathogens.

[0076] Also included are plants that contain altered amounts of or new substances through the use of recombinant DNA technology, particularly to improve human or animal nutrition, such as oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g., Nexera® rapeseed, Dow AgroSciences, Canada).

[0077] Furthermore, plants that contain altered amounts of substances or new substances through the use of recombinant DNA techniques, in particular to improve the production of raw materials, are also included, for example potatoes with increased amylopectin production (e.g. Amflora® potatoes, BASF SE, Germany).

[0078] The organic moieties mentioned in the definitions of the variables above, like the term halogen, are generic to the individual lists of members of that group. n ~C m indicates in each case the possible number of carbon atoms in the group.

[0079] The term halogen denotes in each case F, Br, Cl or I, in particular F, Cl or Br.

[0080] The term "alkyl" as used herein and in alkyl moieties such as alkoxy, alkylthio, etc., refers to a saturated straight-chain or branched hydrocarbon group having 1 to 2 ("C1-C2 alkyl"), 1 to 3 ("C1-C3 alkyl"), 1 to 4 ("C1-C4 alkyl"), or 1 to 6 ("C1-C6 alkyl") carbon atoms. C1-C2-alkyl is CH3 or C2H5. C1-C3-alkyl is additionally propyl and isopropyl. C1-C4-alkyl is additionally butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), or 1,1-dimethylethyl (tert-butyl). C1-C6 alkyl is further, 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.

[0081] The term "haloalkyl" as used herein, also referred to as "partially or fully halogenated alkyl", refers to a straight-chain or branched alkyl group (as defined above) having 1 to 2 ("C1-C2-haloalkyl"), 1 to 3 ("C1-C3-haloalkyl"), 1 to 4 ("C1-C4-haloalkyl") or 1 to 6 ("C1-C6-haloalkyl") carbon atoms, in which some or all of the hydrogen atoms of these groups are replaced by halogen atoms as defined above, in particular C1-C2-haloalkyl, such as chloromethyl, Bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, or pentafluoroethyl. C1-C3 haloalkyl further includes, for example, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, and 3-chloropropyl. Examples of C1-C4-haloalkyl, except as mentioned for C1-C3-haloalkyl, include 4-chlorobutyl.

[0082] As used herein, the term "alkylene" (or alkanediyl) refers to an alkyl group as defined above in which one hydrogen atom at any position of the carbon skeleton is replaced by one further bonding site, thus forming a divalent moiety. Alkylene preferably has 1 to 6 carbon atoms (C1-C6-alkylene), 2 to 6 carbon atoms (C2-C6-alkylene), in particular 1 to 4 carbon atoms (C1-C4-alkylene) or 2 to 4 carbon atoms (C2-C4-alkylene). Examples of alkylene 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.

[0083] As used herein, the term "alkenyl" refers to a monounsaturated straight-chain or branched hydrocarbon group having 2 to 3 ("C2-C3-alkenyl"), 2 to 4 ("C2-C4-alkenyl") or 2 to 6 ("C2-C6-alkenyl") carbon atoms and a double bond at any position, for example, C2-C3-alkenyl, e.g., ethenyl, 1-propenyl, 2-propenyl or 1-methylethenyl; C2-C4-alkenyl, e.g., ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl 1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl; C2-C6-alkenyl, for example, 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 ethyl-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, 1,3-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.

[0084] As used herein, the term "alkynyl" refers to a straight-chain or branched hydrocarbon group having 2 to 3 ("C2-C3-alkynyl"), 2 to 4 ("C2-C4-alkynyl") or 2 to 6 ("C2-C6-alkynyl") carbon atoms and one or two triple bonds at any position, for example, C2-C3-alkynyl, for example, ethynyl, 1-propynyl or 2-propynyl; C2-C4-alkynyl, for example, C2-C6 alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, etc., for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl nyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3 -methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, etc.

[0085] As used herein, the term "cycloalkyl" refers in particular to a monocyclic, bicyclic, or polycyclic saturated hydrocarbon group having 3 to 6 ("C3-C6-cycloalkyl"), or 3 to 5 ("C3-C5-cycloalkyl"), or 3 to 4 ("C3-C4-cycloalkyl") carbon atoms. 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.

[0086] As used herein, the term "cycloalkoxy" refers to a monocyclic cycloalkyl group as defined above, in particular having 3 to 6 ("C3-C6-cycloalkoxy") or 3 to 5 ("C3-C5-cycloalkoxy") or 3 to 4 ("C3-C4-cycloalkoxy") carbon atoms, which is attached to the remainder of the molecule via an oxygen atom.

[0087] The term "cycloalkyl-C1-C4-alkyl" refers to a C3-C8-cycloalkyl ("C3-C3-cycloalkyl-C1-C4-alkyl"), preferably a C3-C6-cycloalkyl ("C3-C6-cycloalkyl-C1-C4-alkyl"), more preferably a C8-C4-cycloalkyl ("C3-C4-cycloalkyl-C1-C4-alkyl"), as defined above, which is bonded to the rest of the molecule via a C1-C4-alkyl group as defined above (preferably a monocyclic cycloalkyl group). 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, except as mentioned for C3-C4-cycloalkyl-C1-C4-alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.

[0088] The term "C1-C2-alkoxy" is a C1-C2-alkyl group as defined above which is bonded via an oxygen atom. The term "C1-C3-alkoxy" is a C1-C3-alkyl group as defined above which is bonded via an oxygen atom. The term "C1-C4-alkoxy" is a C1-C4-alkyl group as defined above which is bonded via an oxygen atom. The term "C1-C6-alkoxy" is a C1-C6-alkyl group as defined above which is bonded via an oxygen atom. "C1-C 10 The term "-alkoxy" refers to a C1-C2 alkyl group as defined above attached through an oxygen atom. 10-alkyl group. C1-C2-alkoxy is OCH3 or OC2H5. C1-C3-alkoxy is furthermore, for example, n-propoxy and 1-methylethoxy (isopropoxy). C1-C4-alkoxy is furthermore, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). C1-C6-Alkoxy is furthermore, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxybutoxy, 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. C1-C8-alkoxy is further, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. 10 -alkoxy is furthermore, for example, nonyloxy, decyloxy and positional isomers thereof.

[0089] The term "C1-C2-haloalkoxy" is a C1-C2-haloalkyl group as defined above which is bonded via an oxygen atom. The term "C1-C3-haloalkoxy" is a C1-C3-haloalkyl group as defined above which is bonded via an oxygen atom. The term "C1-C4-haloalkoxy" is a C1-C4-haloalkyl group as defined above which is bonded via an oxygen atom. The term "C1-C6-haloalkoxy" is a C1-C6-haloalkyl group as defined above which is bonded via an oxygen atom. C1-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5. C1-C3-Haloalkoxy is furthermore, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy or 1-(CH2Br)-2-bromoethoxy. C1-C4-Haloalkoxy is furthermore, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C1-C6-Haloalkoxy is furthermore, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

[0090] As used herein, the term "C1-C6-alkoxy-C1-C4-alkyl" refers to a straight-chain or branched alkyl group 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 of propyl include 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.

[0091] As used herein, the term "alkoxyalkoxy" refers to an alkoxyalkyl group, as defined above, in particular a C1-C6-alkoxy-C1-C4-alkyl group, which is attached to the remainder of the molecule via an oxygen atom. Examples 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, etc.

[0092] The substituent "oxo" replaces a CH2 group with a C(=O) group.

[0093] The term "aryl" refers to phenyl and bicyclic or polycyclic carbocycles having at least one fused phenylene ring attached to the remainder 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.

[0094] The term "aryl-C1-C4-alkyl" relates to C1-C4-alkyl as defined above, in which one hydrogen atom is 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.

[0095] The term "aryloxy-C1-C4-alkyl" relates to C1-C4-alkyl as defined above, in which one hydrogen atom is 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-phenoxy2-propyl.

[0096] The term "aryl-C1-C4-carbonyl" relates to an aryl, especially a phenyl, group as defined above, which is attached to the rest of the molecule by a carbonyl. Particular examples of arylcarbonyl include benzoyl, 1-naphthoyl and 2-naphthoyl.

[0097] The term "hetaryl" refers to an aromatic heterocyclyl or heterocycle having either 5 or 6 ring atoms (5- or 6-membered hetaryl), monocyclic or 8, 9, or 10 ring atoms, and 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, which may have hydrogen or a group different from hydrogen. Hetaryl may have 1, 2, 3, or 4 additional 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, and 4-imidazolyl. , 1,3,4-thiazol-1-yl, 1,3,4-thiazol-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, benzothiazolyl, benzimidazolyl, imidazo[1,2-a]pyridin-2-yl, thieno[3,2-b]pyridin-5-yl, imidazo-[2,1-b]-thiazol-6-yl and 1,2,4-triazolo[1,5-a]pyridin-2-yl.

[0098] Examples of N-linked 5-, 6-, 7-, or 8-membered saturated heterocyclyls or heterocycles include pyrrolidin-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, isoxazolidin-2-yl, thiazolidin-3-yl, isothiazolidin-2-yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-4-yl, azepan-1-yl, and the like.

[0099] The term "hetaryl-C1-C4-alkyl" relates to a C1-C4-alkyl as defined above, in which one hydrogen atom is 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 is 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 that is bonded to the remainder of the molecule by a carbonyl, in particular a C-bonded hetaryl group, 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 the maximum possible number of substituents. When there are two or more defined substituents in a compound of Formula I, they are independently the same or different, unless otherwise specified.

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

[0104] In one preferred embodiment, B 1 , B 2 and up to two of B3 can be N.

[0105] In another preferred embodiment, B 1 is CR B1 and B 2 is CR B2 and B 3 is CR B3 is.

[0106] In another preferred embodiment, B 1 is N and B 2 is CR B2 and B 3 is CR B3 is.

[0107] In another preferred embodiment, B 1 is CR B1 and B 2 is N and B 3 is CR B3 is.

[0108] In another preferred embodiment, B 1 is CR B1 and B 2 is N and B 3 is N.

[0109] In another preferred embodiment, B 1 is N and B 2 is N and B 3 is CR B3 is.

[0110] In another preferred embodiment, B 1 is CR B1 and B 2 is N or CR B2 and B3 is N or CR B3 is.

[0111] In another preferred embodiment, B 3 is CR B3 and B 1 is N or CR B2 and B2 is N or CR B3 is.

[0112] In one preferred embodiment, R 1 is H, halogen, C1-C6-alkyl, or C3-C6-cycloalkyl, where the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN.

[0113] In another preferred embodiment, R 1 is H, halogen, C1-C6-alkyl, or C3-C6-cycloalkyl.

[0114] In another preferred embodiment, R 1 is H, halogen or C1-C6-alkyl, the alkyl portion being unsubstituted or substituted with halogen or CN.

[0115] In another preferred embodiment, R 1is H or C1-C6-alkyl, the alkyl portion being unsubstituted or substituted with halogen or CN.

[0116] In another preferred embodiment, R 1 is C1-C6-alkyl which is unsubstituted or substituted with halogen or CN.

[0117] In another preferred embodiment, R 1 is unsubstituted C1-C6-alkyl.

[0118] In another preferred embodiment, R 1 is C1-C6-alkyl substituted with halogen or CN.

[0119] In another preferred embodiment, R 1 is a C3-C6-cycloalkyl that is unsubstituted or substituted with halogen or CN.

[0120] In another preferred embodiment, R 1 is unsubstituted C3-C6-cycloalkyl.

[0121] In another preferred embodiment, R 1 is C3-C6-cycloalkyl substituted with halogen or CN.

[0122] In another preferred embodiment, R 1 is H or a halogen.

[0123] In another preferred embodiment, R 1 is H.

[0124] In another preferred embodiment, R 1 is a halogen.

[0125] In another preferred embodiment, R 1 is H, Cl, CH3, or cyclopropyl.

[0126] In another preferred embodiment, R 1 is H or NR 6 R 7 is.

[0127] In another preferred embodiment, R 1 is NR 6 R 7 is.

[0128] In one preferred embodiment, R 6 and R 7 are identical 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, where the alkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN or C1-C6-alkyl.

[0129] In another preferred 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.

[0130] In another preferred embodiment, R 6 and R 7 are the same or different and are H, phenyl, -CH2-phenyl, 5- or 6-membered heteroaryl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl, where the phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN or C1-C6-alkyl.

[0131] In another preferred embodiment, R 6 and R 7 are identical or different and are H, —CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl, where the phenyl and heteroaryl moieties are unsubstituted or substituted with halogen, CN or C1-C6-alkyl.

[0132] In another preferred 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, where the alkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN or C1-C6-alkyl.

[0133] In another preferred embodiment, R 6 and R 7 are independently selected from Rx-1 to Rx-7 shown in Table Rx.

[0134] [Table 1]

[0135] In another preferred embodiment, R 6 and R 7 are independently selected from Rx-1, Rx-2, Rx-7, and Rx-8, more preferably from Rx-1 and Rx-7.

[0136] In one preferred embodiment, R 2 is H, halogen, C1-C6-alkyl, or C3-C6-cycloalkyl, where the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN.

[0137] In another preferred embodiment, R 2is H, halogen, C1-C6-alkyl, or C3-C6-cycloalkyl.

[0138] In another preferred embodiment, R 2 is H, halogen or C1-C6-alkyl, where the alkyl portion is unsubstituted or substituted with halogen or CN.

[0139] In another preferred embodiment, R 2 is H or C1-C6-alkyl, where the alkyl portion is unsubstituted or substituted with halogen or CN.

[0140] In another preferred embodiment, R 2 is C1-C6-alkyl which is unsubstituted or substituted with halogen or CN.

[0141] In another preferred embodiment, R 2 is unsubstituted C1-C6-alkyl.

[0142] In another preferred embodiment, R 2 is C1-C6-alkyl substituted with halogen or CN.

[0143] In another preferred embodiment, R 2 is a C3-C6-cycloalkyl that is unsubstituted or substituted with halogen or CN.

[0144] In another preferred embodiment, R 2 is unsubstituted C3-C6-cycloalkyl.

[0145] In another preferred embodiment, R 2 is C3-C6-cycloalkyl substituted with halogen or CN.

[0146] In another preferred embodiment, R 2 is H or a halogen.

[0147] In another preferred embodiment, R 2 is H.

[0148] In another preferred embodiment, R 2 is a halogen.

[0149] In another preferred embodiment, R 2 is H, Cl, Br, F, CH3, C2H5, n-C3H7, isopropyl, cyclopropyl, CH2F, CHF2, or CF3.

[0150] In another preferred embodiment, R 2 is H, CH3, C2H5, isopropyl, or cyclopropyl.

[0151] In another preferred embodiment, R 2 is H.

[0152] In another preferred embodiment, R 2 is CH3.

[0153] In another preferred embodiment, R 2 is C2H5.

[0154] In another preferred embodiment, R 2 is isopropyl.

[0155] In another preferred embodiment, R 2 is cyclopropyl.

[0156] In one preferred embodiment, R B1 , R B2 , R B3 , and R B4 are, independently of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen.

[0157] In another preferred embodiment, R B1 , R B2 , R B3 , and R B4 are, independently of one another, H, halogen, CN, C1-C6-alkyl, or C1-C6-alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen.

[0158] In another preferred embodiment, R B1 , R B2 , R B3 , and R B4 are, independently of one another, H, halogen, or C1-C6-alkyl, where the alkyl portion is unsubstituted or substituted with halogen.

[0159] In another preferred 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.

[0160] In another preferred 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.

[0161] In another preferred embodiment, R B1 and R B4 are, independently of each other, H, Cl or CH3.

[0162] In another preferred embodiment, R B2 and R B3 are, independently of each other, H, Cl, Br, F, CN, CH3, isopropyl, cyclopropyl, OCH3, or OCHF2.

[0163] In another preferred embodiment, R B2 and R B3 are, independently of each other, H, Cl, F, CN, CH3, or OCH3.

[0164] In another preferred embodiment, R B2 and R B3 are, independently of each other, H or Cl.

[0165] In one preferred embodiment, Q is #-C(=O)-N(R 5 )-, where # is Ar 1 Indicates a connection to

[0166] In another preferred embodiment, Q is #-N(R 5 )-C(=O)-, where # is Ar 1 Indicates a connection to

[0167] In one preferred embodiment, R 5 is H, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, where the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN.

[0168] In another preferred embodiment, R 5 is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, where the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN.

[0169] In another preferred embodiment, R 5 is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, the alkyl and cycloalkyl moieties being unsubstituted.

[0170] In another preferred embodiment, R 5is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, where the alkyl and cycloalkyl moieties are substituted with halogen or CN.

[0171] In another preferred embodiment, R 5 is H, CH3, C2H5, or -CH2-cyclopropyl.

[0172] In one preferred embodiment, D is DA.

[0173] In one preferred embodiment, R 3 is H, C1-C6-alkyl, or C3-C6-cycloalkyl, where the alkyl and cycloalkyl moieties are unsubstituted or substituted with halogen or CN.

[0174] In another preferred embodiment, R 3 is H or C1-C6-alkyl, where the alkyl portion is unsubstituted or substituted with halogen or CN.

[0175] In another preferred embodiment, R 3 is H or C3-C6-cycloalkyl, where the cycloalkyl moiety is unsubstituted or substituted with halogen or CN.

[0176] In another preferred embodiment, R 3 is H.

[0177] In another preferred embodiment, R 3 is H, and DA exists in either of the tautomeric forms D3 and D4 below. [ka]

[0178] In one preferred embodiment, R 4is H, C1-C6-alkyl or C3-C6-cycloalkyl, where the alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkyl, -O-(C=O)-C1-C6-alkoxy or CN.

[0179] In another preferred embodiment, R 4 is H or C1-C6-alkyl, where the alkyl moiety is unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkyl, -O-(C=O)-C1-C6-alkoxy, or CN.

[0180] In another preferred embodiment, R 4 is H or C3-C6-cycloalkyl, where the cycloalkyl moiety is unsubstituted or substituted with halogen or CN.

[0181] In another preferred embodiment, R 4 is H.

[0182] In another preferred embodiment, R 4 is H, and DA exists in either of the tautomeric forms D1 and D2 below. [ka]

[0183] In another preferred embodiment, D is DB, where B is a 5- or 6-membered carbocyclic group, where one or two CH moieties of the carbocyclic group may be replaced by a carbonyl group, and the carbocyclic group is unsubstituted or is selected from the group consisting of R h is replaced by .

[0184] In another preferred embodiment, D is DB, where B is a 5- or 6-membered carbocyclic group, where one CH moiety of the carbocyclic group may be replaced by a carbonyl group, and the carbocyclic group is unsubstituted or is selected from the group consisting of R his replaced by .

[0185] In another preferred embodiment, D is DB, where B is a 5- or 6-membered carbocyclic group, one CH2 moiety of which may be replaced by a carbonyl group.

[0186] In another preferred embodiment, D is DB, where B is a 5- or 6-membered carbocyclic group and one CH2 moiety of the carbocyclic group is replaced with a carbonyl group.

[0187] In another preferred embodiment, D is DB selected from D5 to D7, where the carbocyclic groups of the D5 to D7 moieties are unsubstituted or contain one or two substituents R h is replaced by . [ka]

[0188] In another preferred embodiment, D is unsubstituted or contains one or two substituents R h is a group selected from the moieties D5 to D7, substituted with [ka]

[0189] In another preferred embodiment, D is DB selected from D5 to D7, wherein the carbocyclic groups of the D5 to D7 moieties are unsubstituted.

[0190] In another preferred embodiment, D is DB selected from D5 to D7, where the carbocyclic group of the D5 to D7 moieties is substituted with one or two substituents R h is replaced by .

[0191] In another preferred embodiment, D is selected from DA, D5, D6 and D7 as defined herein.

[0192] In another preferred embodiment, D is selected from DA, D5, D6, and D7, wherein the carbocyclic groups of the D5, D6, and D7 moieties are unsubstituted or contain one or two substituents R h is replaced by .

[0193] In another preferred embodiment, D is DA or D5, where D5 is unsubstituted or contains one substituent R h is replaced by .

[0194] In another preferred embodiment, D is selected from DA or D5, wherein the carbocyclic group of D5 is substituted with one substituent R h is replaced by .

[0195] In another preferred embodiment, D is selected from DA or D5, wherein the carbocyclic group of D5 is unsubstituted.

[0196] In another preferred embodiment, D is D5, wherein the carbocyclic group of D5 is unsubstituted or contains one substituent R h is replaced by .

[0197] In one preferred embodiment, Ar 1 is unsubstituted or R Ar1 is phenyl substituted with

[0198] In another preferred embodiment, Ar 1 is unsubstituted or R Ar1 is a 5- or 6-membered hetaryl substituted with

[0199] In a more preferred embodiment, Ar 1 is unsubstituted or R Ar1 phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl or pyridyl, substituted by

[0200] In one preferred embodiment, R Ar1is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, where the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or f In another preferred embodiment, Ar 1 is unsubstituted or R Ar1 ; 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 a 5- or 6-membered hetaryl substituted with

[0201] In another preferred 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, where the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C-C-heterocyclyl, and cycloalkoxy moieties are unsubstituted or are substituted by 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 eis replaced by .

[0202] In another preferred embodiment, R Ar1 is halogen, SF5, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, where the alkyl, alkoxy, alkenyl and alkynyl moieties are unsubstituted or f ; or S(=O) m R e is replaced by .

[0203] In another preferred embodiment, R Ar1 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, where the alkyl and alkoxy moieties are unsubstituted or f is replaced by .

[0204] In another preferred embodiment of the compounds of formula I, Ar 1 is unsubstituted or R Ar1 phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl substituted with 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, where the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C-C-heterocyclyl, and cycloalkoxy moieties are unsubstituted or are substituted by R 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 by halogen); m is 0, 1 or 2.

[0205] In another preferred embodiment of the compounds of formula I, Ar 1 is unsubstituted or R Ar1 phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl substituted with R Ar1 is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, where 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 by halogen); m is 0, 1 or 2.

[0206] In another preferred embodiment, Ar 1 is the Ar shown in Table Ar1 1 -1~Ar 1 -26 are selected.

[0207] [Table 2]

[0208] In another preferred embodiment, Ar 1 Ar 1 -1~Ar 1 -17 are selected.

[0209] In another preferred embodiment, Ar 1 Ar 1 -1~Ar 1 -9 are selected.

[0210] In another preferred embodiment, Ar 1 Ar 1 -1~Ar 1-8 are selected.

[0211] In another preferred embodiment, Ar 1 Ar 1 -1~Ar 1 -3 is selected.

[0212] In one preferred embodiment, Ar 2 is unsubstituted or R Ar2 is phenyl substituted with

[0213] In another preferred embodiment, Ar 2 is unsubstituted or R Ar2 is a 5- or 6-membered hetaryl substituted with

[0214] In another preferred embodiment, Ar 2 is unsubstituted or R Ar2 phenyl, pyrimidinyl, thiophenyl, thiazolyl, or pyridyl substituted with

[0215] In one preferred 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, in which 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.

[0216] In another preferred embodiment, R Ar2is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, where the alkyl, alkoxy and cycloalkyl moieties are unsubstituted or halogen; Or ORNR b R c is replaced by .

[0217] In another preferred embodiment, R Ar2 is halogen, CN, NR b R c , C 1 ~C 6 -alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, where the alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen.

[0218] In another preferred embodiment, R Ar2 is NR b R c is.

[0219] In another preferred embodiment, R Ar2 is halogen, CN, C1-C6-alkyl, where the alkyl portion is unsubstituted or substituted with halogen.

[0220] In another preferred embodiment, R Ar2 is halogen or C1-C6-alkyl, where the alkyl portion is unsubstituted or substituted with halogen.

[0221] In another preferred embodiment, R Ar2 is halogen or C1-C6-alkyl.

[0222] In another preferred embodiment, R Ar2 is a halogen.

[0223] In another preferred embodiment, RAr2 is halogen or CN.

[0224] In another preferred embodiment, Ar 2 is the Ar shown in Table Ar2 2 -1~Ar 2 -20 are selected.

[0225] [Table 3]

[0226] [Table 4]

[0227] In another preferred embodiment, Ar 2 Ar 2 -1~Ar 2 -13 are selected.

[0228] In another preferred embodiment, Ar 2 Ar 2 -1~Ar 2 -3 is selected.

[0229] In one embodiment, R a , R b and R c are the same or different and are H, C1-C6-alkyl, C2-C6-alkenyl, which are unsubstituted or substituted with halogen.

[0230] In another preferred embodiment, R a , R b and R c are the same or different and are H, C1-C6-alkyl, which are unsubstituted or substituted with halogen.

[0231] In one preferred embodiment, R d is H.

[0232] In another preferred embodiment, R d is C1-C6-alkyl.

[0233] In one preferred embodiment, R e is H, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, or C3-C6-halocycloalkyl.

[0234] In another preferred embodiment, R e is C1-C6-alkyl or C1-C6-haloalkyl.

[0235] In one preferred embodiment, R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C3-C6-cycloalkoxy, which are unsubstituted or substituted by halogen.

[0236] In another preferred embodiment, R f is halogen, OH, CN or C1-C6-alkyl.

[0237] In a preferred embodiment, R h is halogen or C1-C6-alkyl.

[0238] In one preferred embodiment, m is 0.

[0239] In another preferred embodiment, m is 1.

[0240] In another preferred embodiment, m is 2.

[0241] In another preferred embodiment, m is 0 or 1.

[0242] In another preferred embodiment, m is 1 or 2.

[0243] In another preferred embodiment of the compounds 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 B2で Yes and B 3 is CR B3 and; R B1 , R B2 , R B3 , and R B4 are, independently of one another, H, halogen, CN, C1-C6-alkyl or C1-C6-alkoxy, where 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 1 is halogen, 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; Ar 1 is unsubstituted or R Ar1 phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl substituted with 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, where the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C-C-heterocyclyl, and cycloalkoxy moieties are unsubstituted or are substituted by R 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 by halogen); m is 0, 1 or 2.

[0244] In another preferred embodiment of the compounds of formula I, Q is -C(=O)-N(R 5 )-and; D is DB, preferably D5; B1 is N or CR B1 and B 2 is CR B2で Yes and B 3 is CR B3 and; R B1 , R B2 , R B3 , and R B4 are, independently of one another, H, halogen, CN, C1-C6-alkyl, or C1-C6-alkoxy, where 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 1 is halogen, C1-C6-alkyl or C3-C6-cycloalkyl; R 2 is C1-C6-alkyl; Ar 1 is unsubstituted or R Ar1 phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl substituted with R Ar1 is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, where 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 unsubstituted or R Ar2is phenyl substituted with; R Ar2 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, where the alkyl, alkoxy and cycloalkyl moieties are unsubstituted or halogen; Or ORNR 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 by halogen); m is 0, 1 or 2.

[0245] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.1 to A.10: [ka]

[0246] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.1 to A.5.

[0247] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.6 to A.10:

[0248] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.1 and A.6.

[0249] In another preferred embodiment, the compound of formula I is selected from compounds of formulae A.2 and A.7.

[0250] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.3 and A.8.

[0251] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.4 and A.9.

[0252] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.5 and A.10.

[0253] In another preferred embodiment, the compound of formula I is a compound of A.1.

[0254] In another preferred embodiment, the compound of formula I is compound A.2.

[0255] In another preferred embodiment, the compound of formula I is compound A.3.

[0256] In another preferred embodiment, the compound of formula I is compound A.4.

[0257] In another preferred embodiment, the compound of formula I is compound A.5.

[0258] In another preferred embodiment, the compound of formula I is compound A.6.

[0259] In another preferred embodiment, the compound of formula I is compound A.7.

[0260] In another preferred embodiment, the compound of formula I is compound A.8.

[0261] In another preferred embodiment, the compound of formula I is compound A.9.

[0262] In another preferred embodiment, the compound of formula I is compound A.10.

[0263] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.1 to 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2-3 is selected.

[0264] In another preferred 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0265] In another preferred embodiment, the compound of formula I is selected from compounds of formulae A.1 and 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0266] In another preferred embodiment, the compound of formula I is selected from compounds of formulae 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0267] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0268] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.4 and A.9, wherein: Q is -C(=O)-N(R 5 )- or -N(R 5 )—C(═O)—, preferably —C(═O)—N(R5 )-and; R 5 is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0269] In another preferred 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0270] In another preferred embodiment, the compound of formula I is A.1, 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0271] In another preferred 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 5is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0272] In another preferred 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 5is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0273] In another preferred 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 5is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0274] In another preferred 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 5is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0275] In another preferred 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 5is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0276] In another preferred 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0277] In another preferred 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, preferably H or CH3; R 2 is H or C1-C6-alkyl, preferably CH3; R B1 , R B2 , RB3 , and R B4 are, independently of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0278] In another preferred 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, preferably H or CH3; R 2 is H or C1-C6-alkyl, preferably CH3; R B1 , R B2 , R B3 , and R B4are, independently of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0279] In another preferred 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar1 Ar 1 -1~Ar 1 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0280] In another preferred embodiment, the compounds of formula I are of formulae I.1 to I.4. [ka]

[0281] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.1 and I.2.

[0282] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.1 and I.3.

[0283] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.3 and I.4.

[0284] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.2 and I.4.

[0285] In another embodiment, the compound of formula I is a compound of formula I.1.

[0286] In another embodiment, the compound of formula I is a compound of formula I.2.

[0287] In another embodiment, the compound of formula I is a compound of formula I.3.

[0288] In another embodiment, the compound of formula I is a compound of formula I.4.

[0289] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae I.1 to I.4, wherein: B 1 is N or CR B1 and B 2 is CR B2で Yes and B 3 is CR B3 and; R B1 , R B2 , R B3 , and R B4 are, independently of one another, H, halogen, CN, C1-C6-alkyl, or C1-C6-alkoxy, where 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 1 is halogen, C1-C6-alkyl or C3-C6-cycloalkyl; R 2 is C1-C6-alkyl; R 3 is H or C1-C6 alkyl; R 4 is H or C1-C6 alkyl; Ar 1 is unsubstituted or R Ar1 phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl substituted with R Ar1 is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, where the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, and C3-C6-heterocyclyl moieties are unsubstituted or f ; NRb 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 unsubstituted or R Ar2 is phenyl substituted with; R Ar2 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, where the alkyl, alkoxy and cycloalkyl moieties are unsubstituted or halogen; Or ORNR 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 by halogen); m is 0, 1 or 2.

[0290] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae I.1 to I.4, wherein: R 5is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H, halogen, C1-C6-alkyl or C3-C6-cycloalkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0291] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae I.1 to I.4, wherein: R 5 is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar2 -1~Ar 2 -3 is selected.

[0292] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.1 and I.2, wherein R 5 is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0293] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae I.1 and I.3, wherein R 5 is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0294] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.3 and I.4, wherein: R 5 is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0295] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.2 and I.4, wherein: R 5 is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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~Ar1 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0296] In another preferred 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where 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; Ar 1 Ar 1 -1~Ar 1 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0297] In another preferred 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, ethyl or C1-C6-alkoxy, where 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 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0298] In another preferred 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で Yes and B 3 is CR B3 and; R B1 , R B2 , R B3 , and R B4 are, independently of one another, H, halogen, CN, C1-C6-alkyl, or C1-C6-alkoxy, where 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 1 is halogen, C1-C6-alkyl or C3-C6-cycloalkyl; R 2 is C1-C6-alkyl; Ar 1 is unsubstituted or R Ar1phenyl, pyrimidinyl, pyridazinyl, thiophenyl, thiazolyl, or pyridyl substituted with R Ar1 is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, where 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 unsubstituted or R Ar2 is phenyl substituted with; R Ar2 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, where the alkyl, alkoxy and cycloalkyl moieties are unsubstituted or halogen; Or ORNR 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 by halogen); m is 0, 1 or 2.

[0299] In another preferred 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-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, or C1-C6-alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2 Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0300] In another preferred embodiment, the compound of formula I is a compound of formula I.4, wherein: R 5 is H, C1-C6-alkyl, or C1-C6-alkyl-C3-C6-cycloalkyl, preferably H, CH3, C2H5, or —CH2-cyclopropyl, more preferably H or CH3; R 1 is H or C1-C6 alkyl, 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 of one another, H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl, ethyl or C1-C6-alkoxy, where the alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted with halogen; Ar 1 Ar 1 -1~Ar 1 -17, preferably Ar 1 -1~Ar 1 -8, more preferably Ar 1 -1~Ar 1 -Selected from 3; Ar 2Ar 2 -1~Ar 2 -13, preferably Ar 2 -1~Ar 2 -3 is selected.

[0301] Specific compounds of formula I are those of formula I.1 to I.4 summarized in Tables 1 to 48 below, with the variable B 1 , B 2 , B 3 and B 4 corresponds to each line of Table B. Each of the radicals mentioned for a substituent in the Table is also itself a particularly preferred embodiment of the substituent in question, independently of the combination in which it is mentioned.

[0302] Table 1.R 1 is H and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0303] Table 2.R 1 is H 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.

[0304] Table 3.R 1 is H and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0305] Table 4.R 1 is H and R 2 is H and R 5 is H and Ar1 Ar 1 -2 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0306] Table 5.R 1 is H and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0307] Table 6.R 1 is H 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.

[0308] Table 7.R 1 is H and R 2 is H and R 5 There is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0309] Table 8.R 1 is H and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0310] Table 9.R 1 is H and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2-1.

[0311] Table 10.R 1 is H and 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.3.

[0312] Table 11.R 1 is H and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0313] Table 12.R 1 is H 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.

[0314] Table 13.R 1 is H and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0315] Table 14.R 1 is H 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.

[0316] Table 15.R1 is H and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0317] Table 16.R 1 is H 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.

[0318] Table 17.R 1 is H and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0319] Table 18.R 1 is H and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0320] Table 19.R 1 is H and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0321] Table 20.R 1 is H and R 2 is CH3 and R 5is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0322] Table 21.R 1 is H and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0323] Table 22.R 1 is H 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.

[0324] Table 23.R 1 is H and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0325] Table 24.R 1 is H 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.

[0326] Table 25.R 1 is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar2 Ar 2 -1.

[0327] Table 26.R 1 is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2.

[0328] Table 27.R 1 is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0329] Table 28.R 1 is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2.

[0330] Table 29.R 1 is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0331] Table 30.R 1 is CH3 and R 2 is H and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2.

[0332] Table 31.R 1 is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0333] Table 32.R 1 is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -2.

[0334] Table 33.R 1 is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0335] Table 34.R 1 is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -2.

[0336] Table 35.R 1 is CH3 and R 2 is H and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0337] Table 36.R 1 is CH3 and R2 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.

[0338] Table 37.R 1 is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0339] Table 38.R 1 is CH3 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.

[0340] Table 39.R 1 is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0341] Table 40.R 1 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.

[0342] Table 41.R 1 is CH3 and R 2 is CH3 and R 5 is H and Ar1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0343] Table 42.R 1 is CH3 and R 2 is CH3 and R 5 is H and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -2 of the compound of formula I.3.

[0344] Table 43.R 1 is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -1 and Ar 2 Ar 2 -1.

[0345] Table 44.R 1 is CH3 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.

[0346] Table 45.R 1 is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar 2 Ar 2 -1.

[0347] Table 46.R 1 is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -2 and Ar2 Ar 2 -2 of the compound of formula I.3.

[0348] Table 47.R 1 is CH3 and R 2 is CH3 and R 5 is CH3 and Ar 1 Ar 1 -3 and Ar 2 Ar 2 -1.

[0349] Table 48.R 1 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.

[0350] [Table 5]

[0351] [Table 6]

[0352] [Table 7]

[0353] [Table 8]

[0354] [Table 9]

[0355] [Table 10]

[0356] [Table 11]

[0357] [Table 12]

[0358] [Table 13]

[0359] [Table 14]

[0360] [Table 15]

[0361] [Table 16]

[0362] [Table 17]

[0363] [Table 18]

[0364] [Table 19]

[0365] Tables 49 to 96: Contains all compounds disclosed in Tables 1 to 48, respectively, where the compound of formula I.3 is replaced with a compound of formula I.4.

[0366] As used herein, the term "compounds of the invention" or "compounds according to the invention" means compounds of formula (I) as defined above, also referred to as "compounds of formula I" or "compound I" or "formula I compounds", including salts, tautomers, and N-oxides thereof.

[0367] The present invention also relates to mixtures of at least one compound of the present invention with at least one mixing partner as defined herein. Preferred are binary mixtures of one compound of the present invention as component I and one mixing partner as defined herein as component II. The preferred weight ratio of such binary mixtures is 5000:1 to 1:5000, preferably 1000:1 to 1:1000, more preferably 100:1 to 1:100, in particular 10:1 to 1:10. In such binary mixtures, components I and II can be used in equal amounts, or an excess of component I or an excess of component II can be used.

[0368] The mixing partners can be selected from pesticides, in particular insecticides, nematicides and acaricides, fungicides, herbicides, plant growth regulators, fertilizers. Preferred mixing partners are insecticides, nematicides and fungicides.

[0369] The following list of pesticides, grouped and numbered according to the Insecticide Resistance Action Committee (IRAC) Mode of Action Classification, with which the compounds of the invention may be used and which may potentially have synergistic effects, is intended to illustrate possible combinations but is not intended to impose any limitations: M.1 Acetylcholinesterase (AChE) inhibitors: M.1A carbamates, such as aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1B Organophosphates, such as acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famflu, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, isopropyl O-(methoxyaminothio) -phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion; M.2. GABA-gated chloride channel antagonists: M.2A cyclic diene organochlorine compounds, such as endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), such as ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole; M.3 M.3A Sodium channel modulators from the class of pyrethroids, e.g., acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, ethyl bifenthrin, kappa-bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, ethyl gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, ethyl zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, ethyl Sfenvalerate, ethyl ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, ethyl tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, ethyl momfluorothrin, epsilon-momfluorothrin, permethrin, fenothrin, prallethrin, ethylprofluthrin, pyrethrins (pyrethram), resmethrin, silafluofen, tefluthrin, ethyl kappa-tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and transfluthrin; sodium channel modulators such as ethyl or M.3B DDT or methoxychlor; M.4 Nicotinic acetylcholine receptor agonists (nAChR): M.4A neonicotinoids, such as acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam; or compound 4A.1 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1H-imidazol-2-amine, M.4A.2: (2E-)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; or M.4B Nicotine; M.4C Sulfoxaflor; M.4D Flupyradifurone; M.4E Triflumezopyrim, M.4E.1a) (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-5-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate, M.4E.1b) (3S)-3-(6-chloro-3-pyridyl)-8-methyl-5-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate, M.4E.1c) (3S)-8-methyl-5-oxo-6-phenyl-3-pyrimidin-5-yl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate, M.4E.1d) (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-5-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate -3-(2-chlorothiazol-5-yl)-8-methyl-5-oxo-6-[3-(trifluoromethyl)phenyl]-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate; M.4E.1e) (3R)-3-(2-chlorothiazol-5-yl)-6-(3,5-dichlorophenyl)-8-methyl-5-oxo-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate, M.4E.1f) (3R)-3-(2-chlorothiazol-5-yl)-8-ethyl-5-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate; M.5 Nicotinic acetylcholine receptor allosteric activators: spinosyns, e.g., spinosad or spinetoram; M.6 Chloride ion channel activators from the class of the avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin; M.7 Juvenile hormone mimetics, for example, M.7A juvenile hormone analogues hydroprene, kinoprene and methoprene; or M.7B fenoxycarb or M.7C pyriproxyfen; M.8 Other nonspecific (multi-site) inhibitors, for example, M.8A alkyl halides, e.g., methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfuryl fluoride, M.8D borax, or M.8E tartar emetic; M.9 TRPV channel modulators of chordotonal organs, e.g., M.9B pymetrozine; pyrifluquinazone; M.10 Mite growth inhibitors, such as M.10A clofentezine, hexythiazox and diflobidazine, or M.10B etoxazole; M.11 Microbial-derived insect midgut membrane disrupting agents, such as Bacillus thuringiensis or Bacillus sphaericus and the insecticidal proteins they produce, such as Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, and Bacillus thuringiensis subsp. tenebrionis subsp. tenebrionis) or BT crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34 / 35Ab1; M.12 Mitochondrial ATP synthase inhibitors, for example, M.12A diafenthiuron, or M.12B organotin acaricides, for example, azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetradifon; M.13 Oxidative phosphorylation uncouplers that disrupt the proton gradient, such as chlorfenapyr, DNOC, or sulfuramide; M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, such as nereistoxin analogues bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium; M.15 Chitin biosynthesis inhibitors type 0, for example benzoylureas, for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron; M.16 Chitin biosynthesis inhibitors type 1, e.g., buprofezin; M.17 Molting disruptors, Diptera, e.g., cyromazine; M.18 Ecdysone receptor agonists, for example diacylhydrazines, for example methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide; M.19 Octopamine receptor agonists, for example, amitraz; M.20 Mitochondrial complex III electron transport inhibitors, for example, M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate; M.21 Mitochondrial complex I electron transport inhibitors, for example, M.21A METI acaricides and insecticides, for example, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21B rotenone; M.22 Voltage-gated sodium channel blockers, such as M.22A indoxacarb, M.22B metaflumizone, or M.22B.1: 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide; M.23 Inhibitors of acetyl-CoA carboxylase, such as tetronic acid and tetramic acid derivatives, for example spirodiclofen, spiromesifen or spirotetramat; M.23.1 Spiropydione; M.24 Mitochondrial complex IV electron transport inhibitors, for example, M.24A phosphines, for example, aluminum phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide; M.25 Mitochondrial complex II electron transport inhibitors, for example β-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen; M.28 Ryanodine receptor modulators from the class of diamides, for example flubendiamide, chlorantraniliprole, cyantraniliprole, tetraniliprole, M.28.1: (R)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide, M.28.2: (S)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl] M.28.5i) N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide; M.28.5j) 3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[ (1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide; M.28.5k) tetrachlorantraniliprole; M.28.5l) N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; or M.28.6: cyhalodiamide; or M.29: Chordotonal organ modulators - undefined target site, e.g., flonicamide; M.UN. Insecticidally active compounds with unknown or unclear mechanism of action, for example, afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, brofuranilide, bromopropylate, chinomethionate, cryolite, dichloromezothiazide, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluranar, metaldehyde, methoxadiazon, piperonyl butoxide, piflubumid, pyridalyl, thioxazaphen, M.UN.3: 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one, M.UN.4: 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, M.UN.5: 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine, or an active substance based on Bacillus firmus (Votivo, I-1582); M.UN.6: Flupirimine; M.UN.8: fluazaindolizine; M.UN.9.a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide; M.UN.9.b): fluxametamide; M.UN.10: 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; M.UN.11.i) 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11.j) 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide M.UN.11.k) N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.l) N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl- Benzamide;M.UN.11.m)N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;M.UN.11.n)4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl -benzamide; M.UN.11.o) 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11.p) N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; or M.UN.12.a) 2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M.UN.12.b) 2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12.c) 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12.d) N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; M.UN.12.e) N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; M.UN.14a) 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; or M.UN.14b) 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol; M.UN.16a) 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.UN.16b) 1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16c) N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4-carboxamide; M.UN.16d) 1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16e) N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M. UN.16f) 1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16g) 1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16h) N-methyl-1-(2-fluoro-1-methyl-propyl)-5-methyl M.UN.16i) 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.UN.16j) 1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, M.UN.17a) N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.UN.17b) N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.UN.17c) N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.UN.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; M.UN.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide; M.UN.17f) methyl 2-[ [2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; M.UN.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.UN.17h) N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.UN.17i) 2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide, M.UN.18.Cyclopyrazoflor; M.UN.19 Sarolanar, M.UN.20 Lochilanar; M.UN.21 N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; M.UN.22a 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M.UN.22b 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine; M.UN.23 Isocycloceram; M.UN.24a) N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide or M.UN.24b) N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide; M.UN.25 acinonapyr; M.UN.26 benzpyrimoxane; M.UN.27 tigolaner; M.UN.28O xazosulfil; M.UN.29a) [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-thiazol-3-yl]phenyl]carbamate; M.UN.29b) [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl ]N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-thiazol-3-yl]phenyl]carbamate;M.UN.29c)[(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-thiazol-3-yl]phenyl] yl]carbamate; M.UN.29d) [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-thiazol-3-yl]phenyl]carbamate; M.UN.29.e) (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[ 4-(trifluoromethoxy)phenyl]-1,2,4-thiazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one or M.UN.29f)(2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-thiazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one; M.UN.30a) 2-(6-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30b) 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30c) 2-(3-ethylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[ 4,5-b]pyridine, M.UN.30d) 2-[3-ethylsulfonyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30e) 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30f) 2-(3-ethylsulfonyl-7-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6 -(Trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30g) 3-ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]pyridine-8-carbonitrile, M.UN.30h) 2-[3-ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, M.UN.30i) 2-[3-ethylsulfonyl-7 -(Trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, M.UN.30j) 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, M.UN.30k) 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine.

[0370] The commercially available compounds of Group M listed above can be found in, among other publications, The Pesticide Manual, 17th Edition, C. MacBean, British Crop Protection Council (2015). The online Pesticide Manual is updated regularly and can be accessed at http: / / bcpcdata.com / pesticide-manual.html.

[0371] Another online database of pesticides that provides ISO common names is http: / / www.alanwood.net / pesticides.

[0372] M.4 cycloxapride is known from WO 2010 / 069266 and WO 2011 / 069456. M.4A.1 is known from Chinese Patent No. 103814937; Chinese Patent No. 105367557; and Chinese Patent No. 105481839. M.4A.2, guadipyr, is known from WO 2013 / 003977, and M.4A.3 (recognized in China as paichongding) is known from WO 2007 / 101369. M.4E.1a) to M.4E.1f) are known from WO 2018177970. M.22B.1 is described in Chinese Patent No. CN10171577, and M.22B.2 is described in Chinese Patent No. CN102126994. Spiropyridione M.23.1 is known from WO 2014 / 191271. M.28.1 and M.28.2 are known from WO 2007 / 101540. M.28.3 is described in WO 2005 / 077934. M.28.4 is described in WO 2007 / 043677. M.28.5a) to M.28.5d) and M.28.5h) are described in WO 2007 / 006670, WO 2013 / 024009 and WO 2013 / 024010, M.28.5i) is described in WO 2011 / 085575, M.28.5j) is described in WO 2008 / 134969, M.28.5k) is described in U.S. Patent Application Publication No. 2011 / 046186, and M.28.5l) is described in WO 2012 / 034403. M.28.6 can be found in WO 2012 / 034472. M.UN.3 is known from WO 2006 / 089633 and M.UN.4 is known from WO 2008 / 067911.M.UN.5 is described in WO 2006 / 043635, and biological control agents based on Bacillus firmus are described in WO 2009 / 124707. Flupirimin is described in WO 2012 / 029672. M.UN.8 is known from WO 2013 / 055584. M.UN.9.a) is described in WO 2013 / 050317. M.UN.9.b) is described in WO 2014 / 126208. M.UN.10 is known from WO 2010 / 060379. Broflanilide and M.UN.11.b) to M.UN.11.h) are described in WO 2010 / 018714, M.UN.11i) to M.UN.11.p) are described in WO 2010 / 127926, M.UN.12.a) to M.UN.12.c) are known from WO 2010 / 006713, M.UN.12.d) and M.UN.12.e) are known from WO 2012 / 000896, and M.UN.14a) and M.UN.14b) are known from WO 2007 / 101369. M.UN.16.a) to M.UN.16h) are described in WO 2010 / 034737, WO 2012 / 084670, and WO 2012 / 143317, respectively, and M.UN.16i) and M.UN.16j) are described in WO 2015 / 055497. M.UN.17a) to M.UN.17.j) are described in WO 2015 / 038503. M.UN.18 cycloprazoflor is described in WO 2014 / 0213448. M.UN.19 is described in WO 2014 / 036056. M.UN.20 is known from WO 2014 / 090918. M.UN.21 is known from EP 2910126 B1.M.UN.22a and M.UN.22b are known from WO 2015 / 059039 and WO 2015 / 190316. M.UN.23a and M.UN.23b are known from WO 2013 / 050302. M.UN.24a) and M.UN.24b) are known from WO 2012 / 126766. Acinonapir M.UN.25 is known from WO 2011 / 105506. Benzpyrimoxane M.UN.26 is known from WO 2016 / 104516. M.UN.27 is known from WO 2016 / 174049. M.UN.28 oxazosulfil is known from WO 2017 / 104592. M.UN.29a) to M.UN.29f) are known from WO 2009 / 102736 or WO 2013116053. M.UN.30 is known from WO 2013 / 050302. M.UN.30a) to M.UN.30k) are known from WO 2018 / 052136.

[0373] The following list of fungicides that can be used in combination with the compounds of the present invention is intended to illustrate, but not limit, the possible combinations.

[0374] A) Respiratory inhibitors - Inhibitors of complex III at the Q site: azoxystrobin (A.1.1), coumetoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestrobulin (A.1.5), phenaminestrobin (A.1.6), fenoxystrobin / flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metomi Nostrobin (A.1.11), Orysastrobin (A.1.12), Picoxystrobin (A.1.13), Pyraclostrobin (A.1.14), Pyrametstrobin (A.1.15), Pyraoxystrobin (A.1.16), Trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide (A.1.18), Pyri Bencarb (A.1.19), Triclopyricarb / Chlorozinecarb (A.1.20), Famoxadone (A.1.21), Fenamidone (A.1.21), Methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), Methyltetrapol (A.1.25), (ZE,2)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methyl methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34), (ZE,2)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), pyriminostrobin (A.1.36), bifujunchi (A.1.37), 2-(ortho-((2,5-dimethylphenyl-oxymethylene)phenyl)-3-methoxy-acrylic acid methyl ester (A.1.38); - Q iInhibitors of complex III at the site: cyazofamid (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate (A.2.3), fenpicoxamide (A.2.4), florylpicoxamide (A.2.5); - Complex II inhibitors: benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamide (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penflufen (A.3.16), penflufen (A.3.17), penflufen (A.3.18), penflufen (A.3.19), penflufen (A.3.20), penflufen (A.3.21), penflufen (A.3.22), penflufen (A.3.23), penflufen (A.3.24), penflufen (A.3.25), penflufen (A.3.26), penflufen (A.3.27), penflufen (A.3.28), penflufen (A.3.29), penflufen (A.3.30), penflufen (A.3.31), penflufen (A.3.32), penflufen (A.3.33), penflufen (A.3.34), penflufen (A.3.35), penflufen (A.3.36), penflufen (A.3.37), penflufen (A.3.38), penflufen (A.3.39), penflufen (A.3.40), penflufen (A.3.41), penflufen (A.3.42), penflu Antipyrad (A.3.16), pydiflumetofen (A.3.17), pyraziflumide (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), inpirfluxam (A.3.22), pyrapropoin (A.3.23), fluindapyr (A.3.28), N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide (A.3.29), methyl (E )-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), isoflucipram (A.3.31), 2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.39);. - Other respiratory inhibitors: diflumetrim (A.4.1); nitrophenyl derivatives: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometallic compounds: fentin salts, e.g. fentin acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctrazine (A.4.11); silthiofam (A.4.12).

[0375] B) Sterol biosynthesis inhibitors (SBI fungicides) - C14 demethylase inhibitors: Triazoles: Azaconazole (B.1.1), Bitertanol (B.1.2), Bromuconazole (B.1.3), Cyproconazole (B.1.4), Difenoconazole (B.1.5), Diniconazole (B.1.6), Diniconazole-M (B.1.7), Epoxiconazole (B.1.8), Fenbuconazole (B.1.9), Fluquinconazole (B.1.10), Flusilazole (B.1.11), Flutriafol (B.1.12), Hexaconazole (B.1.13), Imiben Conazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxopoconazole (B.1.19), paclobutrazol (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole azole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.31), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.32), ipfentrifluol Conazoles (B.1.37), mefentrifluconazole (B.1.38), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46), triflumizole (B.1.47); pyrimidines, pyridines, piperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52);. - Delta-14 reductase inhibitors: aldimorph (B.2.1), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8); - 3-ketoreductase inhibitors: fenhexamid (B.3.1); - Other sterol biosynthesis inhibitors: chlorfenomizole (B.4.1).

[0376] C) Nucleic acid synthesis inhibitors - phenylamide or acylamino acid fungicides: benalaxyl (C.1.1), benalaxyl-M (C.1.2), chiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurase (C.1.6), oxadixyl (C.1.7); - Other nucleic acid synthesis inhibitors: hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro-2(4-chlorophenylmethoxy)pyrimidin-4-amine (C.2.8).

[0377] D) inhibitors of cell division and the cytoskeleton - Tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D.1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), pyridaclomethyl (D.1.6), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1.16); - Other cytostatics: diethofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriophenone (D.2.7).

[0378] E) Amino acid and protein synthesis inhibitors - Methionine synthesis inhibitors: cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3); - Protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracycline (E.2.6).

[0379] F) Signal transduction inhibitors - MAP / histidine kinase inhibitors: fluoroimide (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5); - G protein inhibitors: quinoxifen (F.2.1).

[0380] G) Lipid and membrane synthesis inhibitors - phospholipid biosynthesis inhibitors: edifenphos (G.1.1), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4); - Lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7); - Phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7); - Compounds affecting cell membrane permeability and fatty acids: propamocarb (G.4.1); - Inhibitors of oxysterol-binding proteins: oxathiapiprolin (G.5.1), fluoxapiprolin (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]- N-Tetralin-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.11), pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.11).

[0381] H) Multi-site inhibitors - inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7); - Thiocarbamates and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9); - Organic chlorine compounds: anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorophenol (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11); - Guanidines, etc.: Guanidine (H.4.1), Dodine (H.4.2), Dodine free base (H.4.3), Guazatine (H.4.4), Guazatine acetate (H.4.5), Iminoctadine (H.4.6), Iminoctadine triacetate (H.4.7), Iminoctadine tris(albesilate) (H.4.8), Dithianone (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10).

[0382] I) Cell wall synthesis inhibitors - Glucan synthesis inhibitors: validamycin (I.1.1), polyoxin B (I.1.2); - Melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5).

[0383] J) Plant defense inducers - acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminium (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10).

[0384] K) Mechanism of action unknown - Bronopol (K.1.1), sinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclocymet (K.1.7), diclomedine (K.1.8), difenzoquat (K.1.9), difenzoquat-methylsulfate (K.1.10), diphenylamine (K.1.11), fenitropan (K.1.12), fenpyrazamine (K.1.13), flumetobir (K.1.14), flusulfamide (K.1.15) .1.15), fluthianil (K.1.16), harpin (K.1.17), metasulfocarb (K.1.18), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21), oxine-copper (K.1.22), proquinazid (K.1.23), tebufloquine (K.1.24), tecloftalam (K.1.25), triazoxide (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N -methylformamidine (K.1.27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidine (K.1.28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N -methyl-formamidine (K.1.30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31), N'-[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-propanol 2-ynyloxy-acetamide (K.1.36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzimidazole (K.1.39), ethyl (Z)-3- Amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40), Picarburazox (K.1.41), Pentyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.42), But-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.1 .43), ipflufenoquine (K.1.44), quinofumelin (K.1.47), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), diclobenthiazox (K.1.52), N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine (K.1.53), pyrifenamine (K.1.54).

[0385] The fungicides listed under their common names, their preparations and their activity, for example against harmful fungi, are known (see http: / / www.alanwood.net / pesticides / ) and these substances are commercially available.

[0386] The active substances designated as component 2, their preparation and their activity, for example, against harmful fungi, are known (see http: / / www.alanwood.net / pesticides / ), and these substances are commercially available. Compounds described in IUPAC nomenclature, their preparation and their pesticidal activity are also known (Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A-141317; EP-A-152031; EP-A-226917; EP-A-243970; EP-A-256503; EP-A-428941; EP-A-532022; EP-A-1028125; EP-A-1035122). No.; EP-A1201648; EP-A1122244; JP-A-2002316902; DE-B-19650197; DE-B-10021412; DE-B-102005009458; U.S. Pat. No. 3,296,272; U.S. Pat. No. 3,325,503; WO-A-98 / 46608; WO-A-99 / 14187; WO-A- WO 99 / 24413; WO 99 / 27783; WO 00 / 29404; WO 00 / 46148; WO 00 / 65913; WO 01 / 54501; WO 01 / 56358; WO 02 / 22583; WO 02 / 40431; WO 03 / 10149; WO Publication No. 03 / 11853; International Publication No. 03 / 14103; International Publication No. 03 / 16286; International Publication No. 03 / 53145; International Publication No. 03 / 61388; International Publication No. 03 / 66609; International Publication No. 03 / 74491; International Publication No. 04 / 49804; International Publication No. 04 / 83193; International Publication No. 05 / 120234;WO 05 / 123689; WO 05 / 123690; WO 05 / 63721; WO 05 / 87772; WO 05 / 87773; WO 06 / 15866; WO 06 / 87325; WO 06 / 87343; WO 07 / 82098; WO 07 / 90624; WO 10 / 139271 WO 11 / 028657; WO 12 / 168188; WO 07 / 006670; WO 11 / 77514; WO 13 / 047749; WO 10 / 069882; WO 13 / 047441; WO 03 / 16303; WO 09 / 90181; WO 13 / 007767; WO 13 / 010862 No. WO 13 / 127704; WO 13 / 024009; WO 13 / 24010; WO 13 / 047441; WO 13 / 162072; WO 13 / 092224; WO 11 / 135833; CN1907024; CN1456054; CN103387541; CN1309897; WO 12 / 84812 No.; CN1907024; WO 09094442; WO 14 / 60177; WO 13 / 116251; WO 08 / 013622; WO 15 / 65922; WO 94 / 01546; EP 2865265; WO 07 / 129454; WO 12 / 165511; WO 11 / 081174;(See WO 13 / 47441). Some compounds are identified by their CAS Registry Number, which consists of three parts, the first of which consists of 2 to 7 digits, the second of which consists of 2 digits, and the third of which consists of 1 digit, separated by hyphens.

[0387] Biopesticides Suitable mixing partners for the compounds of the present invention also include biopesticides.

[0388] Biopesticides are defined as forms of pesticides based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (chemical compounds such as metabolites, proteins, or extracts from organisms or other natural sources) (US Environmental Protection Agency: http: / / www.epa.gov / pesticides / biopesticides / ). Biopesticides are divided into two main classes: microbial pesticides and biochemical pesticides: (1) Microbial pesticides consist of bacteria, fungi, or viruses (often containing metabolic products produced by bacteria and fungi). Entomopathogenic nematodes, which are multicellular, are also classified as microbial pesticides. (2) Biochemical pesticides are naturally occurring substances or are structurally similar and functionally identical to naturally occurring substances and are extracts from biological sources that control pests or provide other crop protection uses, as defined below, but have a non-toxic mode of action (e.g., growth or development regulation, attractant, repellent, or defense activator (e.g., induced resistance)) and are relatively non-toxic to mammals.

[0389] Biopesticides for use against crop diseases have already been established in a variety of crops. For example, biopesticides already play an important role in controlling downy mildew. Their advantages include a zero-day preharvest interval, the ability to be used under moderate to severe disease pressure, and the ability to be used in mixtures or rotation programs with other registered pesticides.

[0390] The main growth areas for biopesticides are in the fields of seed treatment and soil improvement. Biopesticide seed treatments are used, for example, to control soil-borne fungal pathogens that cause seed rot, decay, root rot, and seedling blight. They can also be used to control fungal pathogens present within seeds and on the surface of seeds. Many biopesticide products also exhibit the ability to stimulate plant host defense and other physiological processes, which can make treated crops more resistant to various biotic and abiotic stresses or regulate plant growth. Many biopesticide products also exhibit the ability to stimulate plant health, plant growth, and / or yield-enhancing activities.

[0391] The following list of pesticides that can be used in combination with the compounds of the present invention is intended to illustrate, but not limit, the possible combinations.

[0392] L) Biopesticides L1) Microbial pesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. amyloliquefaciens subsp. plantarum ssp. plantarum (also known as B. velezensis), B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, B. velezensis, Candida oleophila, C. saitoana, Clavibacter michiganensis michiganensis (bacteriophage), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f.catenulate (also named Gliocladium catenulate), Gliocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei, Paenibacillus epiphyticus, P. polymyxa, Pantoea bagans vagans, Penicillium bilaiae, Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus flavus), Trichoderma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T.T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahlia, Zucchini yellow mosaic virus (non-virulent strain); L2) Biochemical pesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activity: harpin protein, Reynoutria sachalinensis extract; L3) Microbial pesticides with insecticidal, acaricidal, molluscicidal and / or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, Bt ssp. israelensis, Bt ssp. galleriae, Bt ssp. kurstaki, Bt ssp. tenebrionis, Beauveria bassiana bassiana, B. bronniartii, Burkholderia spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HearNPV), Helicoverpa zea granulovirus (HearNPV), Helicoverpa pomonella granulo ... nucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium (L.muscarium, Metarhizium anisopliae, M. anisopliae var. anisopliae, M. anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus popilliae, Pasteuria spp.), P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, and S. microflavus; L4) Biochemical pesticides having insecticidal, acaricidal, molluscicidal, pheromone and / or nematicidal activity; L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-ethyldecadienoate (pair ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, ravanuryl senecioate, cis-jasmone, 2-methyl-1-butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octyl methyl jasmonate, Tadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, pentatemanone, (E,Z,Z)-3,8,11-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate, (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, (Z)-11-tetradecenal, (Z)-11-tetradecen-1-ol, Chenopodium ambrosiodes extract; neem oil, Quillaja extract; L5) Microbial pesticides with plant stress reducing activity, plant growth regulator activity, plant growth promoting activity and / or yield enhancing activity: Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices intraradices, Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli, Rlbv. trifolii, Rlbv. viciae, R. tropici, Sinorhizobium meliloti.

[0393] Biopesticides from groups L1) and / or L2) may also have insecticidal, acaricidal, molluscicidal, pheromone, nematicidal, plant stress-relieving, plant growth regulator, plant growth-promoting, and / or yield-increasing activity. Biopesticides from groups L3) and / or L4) may also have fungicidal, bactericidal, virucidal, plant defense active, plant stress-relieving, plant growth regulator, plant growth-promoting, and / or yield-increasing activity. Biopesticides from group L5) may also have fungicidal, bactericidal, virucidal, plant defense active, insecticidal, acaricidal, molluscicidal, pheromone, and / or nematicidal activity.

[0394] Many of these biopesticides have been deposited under the accession numbers mentioned herein (prefixes such as ATCC or DSM refer to the acronyms of the respective culture collections, for details see, for example, http: / / www.wfcc.info / ccinfo / collection / by_acronym / ), are mentioned in the literature, are registered, and / or are commercially available: Aureobasidium pullulans DSM 14940 and DSM 14941 mixture isolated in Konstanz, Germany in 1989 (e.g., BlossomProtect® germplasm from bio-ferm GmbH, Austria), Azospirillum brasilense Sp245 (BR 11005; e.g., BASF Agricultural Specialties), isolated in the wheat region (Paso Fundo) of southern Brazil at least before 1980, Ltd., Brazil), A. brasilense Ab-V5 and Ab-V6 (e.g., AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil or Simbiose-Maiz from Simbiose-Agro, Brazil; Plant Soil 331, 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; U.S. Pat. No. 8,445,255); B. amyloliquefaciens ssp. plantarum strain, formerly sometimes called B. subtilis but now classified as B. velezensis together with B. methylotrophicus and B. velezensis ( Int. J. Syst. Evol. Microbiol. 66, 1212-1217, 2016): B. subsp. plantarum or B. velezensis D747 (U.S. Patent Application Publication No. 20130236522A1; FERM BP-8234; e.g., Double Nickel™ 55 from Certis LLC, USA), isolated from the air of Kikugawa City, Japan. WDG), Bassp. plantarum or B. velezensis FZB24 isolated from soil in Brandenburg, Germany (also called SB3615; DSM 96-2; J. Plant Dis. Prot. 105, 181-197, 1998; e.g., Taegro® from Novozyme Biologicals, Inc., USA), Bassp. plantarum or B. velezensis FZB42 isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998; e.g., RhizoVital® 42 from AbiTEP GmbH, Germany), Sutton Basp. plantarum or B. velezensis MBI600 (also called 1430; NRRL B-50595; U.S. Patent Application Publication No. 2012 / 0149571 A1 ), isolated from broad beans in Bonington, Nottinghamshire, UK, at least before 1988; e.g., Integral® from BASF Corp., USA, California, USABassp. plantarum or B. velezensis QST-713 (NRRL B-21661; e.g., Serenade® MAX from Bayer Crop Science LP, USA), isolated from a peach orchard in 1995 in South Dakota, USA; Bassp. plantarum or B. velezensis TJ1000 (also referred to as 1BE; ATCC BAA-390; Canadian Patent Application Publication No. 2471555A1; e.g., QuickRoots® from TJ Technologies, Watertown, SD, USA), isolated in 1992 in South Dakota, USA; B. firmus CNCM I-1582 (parent strain EIP-N1 (CNCM I-1582) isolated from soil in the central plains of Israel); I-1556) (WO 2009 / 126473, U.S. Pat. No. 6,406,690; e.g., Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 (IDAC 260707-01; e.g., PRO-MIX® BX from Premier Horticulture, Quebec, Canada), isolated from the rhizosphere of apple trees in Mexico, B. pumilus INR-7 (also referred to as BU-F22 and BU-F33), isolated from cucumber plants infested with Erwinia tracheiphila at least before 1993 (NRRL B-50185, NRRL B-50153; U.S. Pat. No. 8,445,255), B. pumilus KFP9F isolated from the rhizosphere of pasture grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014 / 029697; e.g., BAC-UP or FUSION-P from BASF Agricultural Specialties (Pty) Ltd., South Africa), B. pumilus (B.B. pumilus QST 2808, isolated in 1998 from soil collected in Pohnpei, Federated States of Micronesia (NRRL B-30087; e.g., Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288 (NRRL B-50304; U.S. Pat. No. 8,445,255), and B. subtilis FB17 (also called UD 1022 or UD 10-22), isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol. 27, 372-379, 2004; U.S. Patent Application Publication No. 2010 / 0260735; WO 2011 / 109395; B. thuringiensis ssp. aizawai ABTS-1857 (also called ABG-6346; ATCC SD-1372; e.g., XenTari® from BioFa AG, Muensingen, Germany), isolated in 1987 from soil collected from a lawn in Ephraim, Wisconsin, USA; Bt ssp. kurstaki ABTS-351 (ATCC SD-1372), identical to HD-1, isolated in 1967 from infected black bollworms in Brownsville, Texas, USA; SD-1275; e.g., Dipel® DF from Valent BioSciences, IL, USA), Bt subsp. kurstaki SB4 isolated from the larval corpses of E. saccharina (NRRL B-50753; e.g., Beta Pro® from BASF Agricultural Specialties (Pty) Ltd., South Africa), Bt subsp. tenebrionis (Bt ssp.tenebrionis NB-176-1 (a mutant of the wild-type strain NB-125 isolated in 1982 from dead pupae of the mealworm beetle Tenebrio molitor) (DSM 5480; EP 585215 B1; e.g., Novodor® from Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e.g., BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e.g., Naturalis® from CBC (Europe) Srl, Italy), the tortoise leaf beetle Conchyloctenia punctata B. bassiana PPRI 5339 (NRRL 50757; e.g., BroadBand® from BASF Agricultural Specialties (Pty) Ltd., South Africa), isolated from larvae of B. punctata, the Brazilian Bradyrhizobium elkanii strain SEMIA 5019 (also called 29W), isolated in Rio de Janeiro, Brazil, and SEMIA 587 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g., GELFIX® from BASF Agricultural Specialties Ltd., Brazil), isolated in 1967 in the state of Rio Grande do Sul, from an area where North American isolates were previously inoculated, and used in commercial inoculants since 1968. 5), B. japonicum 532c (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990), isolated from a field in Wisconsin in the USA; e.g., BASF Agricultural Specialties Ltd., in Rhizoflo®, Histic®, and Hicoat® Super from Canada), the B. japonicum E-109 variant of USDA 138 strain (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 2011); the B. japonicum strain deposited at SEMIA and known from Appl. Environ. Microbiol. 73(8), 2635, 2007: SEMIA 5079 (CPAC 15; e.g., BASF Agricultural Specialties), isolated from soil in the Cerrados region of Brazil by Embrapa-Cerrados, and used in commercial inoculants since 1992; B. japonicum SEMIA 5080 (CPAC7; e.g., GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil), a natural variant of SEMIA 586 (CB1809), originally isolated in the USA, obtained under laboratory conditions by Embrapa-Cerrados in Brazil and used in commercial inoculants since 1992; Burkholderia sp. A396 (NRRL B-50319; WO 2013 / 032693; Marrone Bio Innovations, Inc., USA), isolated from soil in Nikko, Japan in 2008; Coniothyrium minitans (Coniothyrium spp.), isolated from rapeseed. minitans) CON / M / 91-08 (WO 1996 / 021358; DSM 9660; e.g., Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin (alpha-beta) protein (Science 257, 85-88, 1992; e.g., Plant Health Care plc, UK),Messenger™ or HARP-N Tek from Adermatt Biocontrol, Switzerland), Helicoverpa armigera nuclear polyhedrosis virus (HearNPV) (J. Invertebrate Pathol. 107, 112-126, 2011; e.g., Helicovex® from Adermatt Biocontrol, Switzerland); Diplomata® from Koppert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single-capsid nuclear polyhedrosis virus (HzSNPV) (e.g., Gemstar® from Certis LLC, USA), Helicoverpa zea nuclear polyhedrosis virus ABA-NPV-U (e.g., Heligen® from AgBiTech Pty Ltd., Queensland, Australia), Heterorhabditis bacteriophora (e.g., Nemasys® G from BASF Agricultural Specialties Limited, UK), Isaria fumosorosea isolated from mealybugs on gynura in Apopka, Florida, USA. fumosorosea) Apopka-97 (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761, 2012; e.g., PFR-97™ or PreFeRal™ from Certis LLC, USA), Metarhizium anisopliae var. anisopliae isolated from the codling moth in Austria.anisopliae F52 (also called 275 or V275) (DSM 3884, ATCC 90448; e.g., Met52®, Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolated from grapevines in central Israel (U.S. Pat. No. 6,994,849; NRRL Y-30752; e.g., Shemer®, formerly Agrogreen, Israel), and Paecilomyces ilacinus 251 isolated from infected nematode eggs in the Philippines (AGAL 89 / 030550; WO 1991 / 02051; Crop Protection 27, 352-361, 2008; e.g., Bayer CropScience). AG, Germany (BioAct® and Certis, USA (MeloCon®)), Paenibacillus alvei NAS6G6 isolated from the rhizosphere of grasses in South Africa at least before 2008 (WO 2014 / 029697; NRRL B-50755; e.g., BAC-UP from BASF Agricultural Specialties (Pty) Ltd., South Africa), Paenibacillus strains isolated from soil samples in various locations in Europe, including Germany: P. epiphyticus Lu17015 (WO 2016 / 020371; DSM 26971), P. polymyxa subsp. plantarum (P. polymyxa ssp. plantarum) Lu16774 (WO 2016 / 020371; DSM 26969), Pp subsp. plantarum (Pps sp. plantarum) strain Lu17007 (WO 2016 / 020371; DSM 26970); Illinois, USPasteuria nishizawae Pn1 (ATCC SD-5833; Federal Register 76(22), 5808, February 2, 2011; e.g., Clariva™ PN from Syngenta Crop Protection, LLC, USA), which was isolated from a soybean field in the mid-2000s in A. aureus, and Penicillium bilaiae (also known as P. bilaii) strains ATCC 18309 (=ATCC 74319), ATCC 20851, and / or ATCC 22348 (=ATCC 74318), originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Res. Sci. 78(1), 91-102, 1998; U.S. Pat. No. 5,026,417; WO 1995 / 017806; e.g., JumpStart®, Provide® from Novozymes Biologicals BioAg Group, Canada), Reynoutria sachalinensis extract (European Patent No. 0307510B1; e.g., Regalia® SC from Marrone BioInnovations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e.g., Millenium® from BASF Agricultural Specialties Limited, UK), S. feltiae (e.g., BioWorks, Inc.Nemashield® from BASF Agricultural Specialties Limited, UK; Nemasys® from BASF Agricultural Specialties Limited, UK), Streptomyces microflavus NRRL B-50550 (WO 2014 / 124369; Bayer CropScience, Germany), Trichoderma asperelloides JM41R isolated in South Africa (NRRL 50759; also known as T. fertile; e.g., Trichoplus® from BASF Agricultural Specialties (Pty) Ltd., South Africa), T. harzianum T-22 (also known as KRL-AG2) (ATCC 20847; BioControl 57, 687-696, 2012; e.g., BioWorks Plantshield® from Advanced Biological Marketing Inc., Van Wert, OH, USA or SabrEx® from Advanced Biological Marketing Inc., Van Wert, OH, USA.

[0395] According to the present invention, the solid matter (dry matter) of a biopesticide (excluding oils such as neem oil) is considered to be the active ingredient (e.g., as obtained after drying or evaporation of the extraction or suspension medium in the case of a liquid formulation of a microbial pesticide).

[0396] According to the present invention, the weight ratios and percentages used for biological extracts, such as Quillay extract, are based on the total weight of the dry content (solid matter) of the respective extract.

[0397] The total weight ratio of the composition comprising at least one microbial pesticide in the form of viable microbial cells, including dormant forms, is 1×10 10The amount of CFU of each microorganism can be used to calculate the total weight of each active ingredient by the formula: CFU is equal to 1 gram of total weight of each active ingredient. Colony forming units are a measure of viable microbial cells, particularly fungal and bacterial cells. Furthermore, in this specification, "CFU" can be understood as the number of individual (juvenile) nematodes in the case of (entomopathogenic) nematode biopesticides, such as Steinernema feltiae.

[0398] When mixtures containing microbial pesticides are used for crop protection, the application rate is preferably about 1 x 10 6 ~Approx. 5×10 15 (or more) CFU / ha, preferably about 1 x 10 8 ~Approx. 1×10 13 CFU / ha, more preferably about 1 x 10 9 ~Approx. 1×10 12 In the case of (entomopathogenic) nematodes (e.g. Steinernema feltiae) as microbial pesticides, the application rate is preferably in the range of 1 x 10 CFU / ha. 5 ~1×10 12 (or more), more preferably 1 × 10 8 ~1×10 11 , and even more preferably 5×10 8 ~1×10 10 It can range from individuals (eg in the form of eggs, juveniles or any other live stage, preferably in the immature juvenile stage).

[0399] When the mixture containing the microbial pesticide is used for seed treatment, the application rate relative to the plant propagation material is preferably about 1 x 10 6 ~1×10 12 (or more) CFU / seed. Preferably, the concentration is about 1 x 10 6 ~Approx. 1×10 9 In the case of microbial pesticide II, the application rate for plant propagation material is also preferably about 1 x 10 CFU per 100 kg of seeds. 7 ~1×10 14(or more) CFU, preferably 1 x 10 per 100 kg of seeds 9 ~Approx. 1×10 12 CFU range.

[0400] The present invention also relates to an agrochemical composition comprising an adjuvant and at least one compound of the invention or a mixture thereof.

[0401] The pesticidal compositions comprise a pesticidally effective amount of a compound of the present invention or a mixture thereof, the term "pesticidally effective amount" being defined below.

[0402] The compounds of the present invention or their mixtures can be converted into conventional types of pesticide compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, presses, capsules, and mixtures thereof. Examples of composition types are suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, lozenges, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), presses (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations (e.g., GF) for the treatment of plant seedlings 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.

[0403] 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.

[0404] Examples of 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 promoters, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, adhesives and binders.

[0405] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling fractions of mineral oil, e.g., kerosene, light oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g., toluene, paraffin, tetrahydronaphthalene, alkylated naphthalene; alcohols, e.g., ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e.g., cyclohexanone; esters, e.g., lactate esters, carbonate esters, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonate esters; amines; amides, e.g., N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

[0406] Suitable solid carriers or fillers are mineral earths such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders such as cellulose, starch; fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin such as grain meal, bark meal, wood meal, nut meal and mixtures thereof.

[0407] Suitable surfactants are surface-active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Edition or North American Edition).

[0408] Suitable anionic surfactants include alkali salts, alkaline earth salts, or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates include alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalene and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamates. Examples of sulfates include sulfates of fatty acids and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid esters. Examples of phosphates include phosphate esters. Examples of carboxylates include alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0409] Suitable nonionic surfactants include alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates include compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters, alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide, preferably ethylene oxide, can be used for alkoxylation. Examples of N-substituted fatty acid amides include fatty acid glucamides or fatty acid alkanolamides. Examples of esters include fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar-based surfactants include sorbitan, ethoxylated sorbitan, sucrose and glucose esters, or alkyl polyglucosides. Polymeric surfactants include homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, and vinyl acetate.

[0410] Suitable cationic surfactants include quaternary surfactants, such as quaternary ammonium compounds with one or two hydrophobic groups or salts of long-chain primary amines. Suitable amphoteric surfactants include alkylbetaines and imidazolines. Suitable block polymers include AB or ABA block polymers containing polyethylene oxide and polypropylene oxide blocks, or ABC block polymers containing alkanol, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes include polyacids or polybasics. Examples of polyacids include alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybasics include polyvinylamine or polyethyleneamine.

[0411] Suitable adjuvants are compounds that have negligible or no pesticidal activity of their own and that enhance the biological performance of the compounds of the invention against their targets. Examples include surfactants, mineral or vegetable oils, and other auxiliary agents. Further examples are listed in Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[0412] Suitable thickening agents are polysaccharides (eg xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[0413] Suitable fungicides are bronopol and isothiazolinone derivatives, such as alkyliso-thiazolinones and benzisothiazolinones.

[0414] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea, and glycerin.

[0415] Suitable antifoaming agents are silicones, long chain alcohols, and salts of fatty acids.

[0416] Suitable colorants (e.g., red, blue, or green) are low-water-soluble pigments and water-soluble dyes, such as inorganic colorants (e.g., iron oxide, titanium oxide, iron hexacyano) and organic colorants (e.g., alizarin, azo, and phthalocyanine colorants).

[0417] Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0418] Examples of types of compositions and methods for their preparation are given below.

[0419] i) Water-soluble concentrates (SL, LS) 10 to 60% by weight of the compound I according to the invention and 5 to 15% by weight of a wetting agent (e.g., alcohol alkoxylate) are dissolved in water and / or a water-soluble solvent (e.g., alcohol), the remaining amount being up to 100% by weight. The active substance dissolves upon dilution with water.

[0420] ii) Dispersible Concentrate (DC) 5 to 25% by weight of the compound I according to the present invention and 1 to 10% by weight of a dispersing agent (e.g., polyvinylpyrrolidone) are dissolved in an organic solvent (e.g., cyclohexanone) with the remaining amount being up to 100% by weight. Dilution with water gives a dispersion.

[0421] iii) Emulsifying concentrates (EC) 15 to 70% by weight of the compound I according to the present invention and 5 to 10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate, castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e.g., aromatic hydrocarbon) with the remaining amount being up to 100% by weight. Upon dilution with water, an emulsion is obtained.

[0422] iv) Emulsions (EW, EO, ES) 5-40% by weight of the compound I according to the present invention and 1-10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate, castor oil ethoxylate) are dissolved in 20-40% by weight of a non-water-soluble organic solvent (e.g., aromatic hydrocarbon). This mixture is added to up to 100% by weight of water using an emulsifier to form a homogeneous emulsion. Dilution with water results in an emulsion.

[0423] v) Suspension (SC, OD, FS) In a stirred ball mill, 20-60% by weight of the compound I according to the invention is ground with 2-10% by weight of dispersants and wetting agents (e.g., sodium lignosulfonate and alcohol ethoxylates), 0.1-2% by weight of a thickener (e.g., xanthan gum), and the remaining amount of water up to 100% by weight to form a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. For the FS type, up to 40% by weight of a binder (e.g., polyvinyl alcohol) is added.

[0424] vi) Water-dispersible granules and water-soluble granules (WG, SG) 50-80% by weight of the compound I according to the invention is finely ground with the addition of dispersants and wetting agents (e.g., sodium lignosulfonate and alcohol ethoxylates) in amounts up to 100% by weight, and prepared as water-dispersible or water-soluble granules by means of technical equipment (e.g., extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

[0425] vii) Wettable powders (powder) and water-soluble powders (WP, SP, WS) 50-80% by weight of the compound I according to the invention is milled in a rotor-stator mill with the addition of 1-5% by weight of a dispersant (e.g., sodium lignosulfonate), 1-3% by weight of a wetting agent (e.g., alcohol ethoxylate), and 100% by weight of a solid carrier (e.g., silica gel). Upon dilution with water, a stable dispersion or solution of the active substance is obtained.

[0426] viii) Gel formulations (GW, GF) In a stirred ball mill, 5 to 25% by weight of the compound I according to the invention is milled with 3 to 10% by weight of a dispersant (e.g., sodium lignosulfonate), 1 to 5% by weight of a thickener (e.g., carboxymethylcellulose), and the remaining amount of water up to 100% by weight to obtain a fine suspension of the active substance. Upon dilution with water, a stable suspension of the active substance is obtained.

[0427] ix) Microemulsion (ME) 5-20% by weight of compound I according to the present invention is added to 5-30% by weight of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a surfactant blend (e.g., alcohol ethoxylate and arylphenol ethoxylate), and the remaining amount of water up to 100%. The mixture is stirred for 1 hour, and a thermodynamically stable microemulsion is spontaneously formed.

[0428] x) Microcapsules (CS) An oil phase containing 5 to 50% by weight of the compound I according to the present invention, 0 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and 2 to 15% by weight of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Poly(meth)acrylate microcapsules are formed by radical polymerization initiated by a radical initiator. Alternatively, an oil phase containing 5 to 50% by weight of the compound I according to the present invention, 0 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Polyurea microcapsules are formed by the addition of a polyamine (e.g., hexamethylenediamine). The monomer is present in an amount of 1 to 10% by weight. The weight percentages are relative to the total CS composition.

[0429] xi) Dustable powder (DP, DS) 1 to 10% by weight of the compound I according to the invention is finely ground and intimately mixed with the remaining amount up to 100% by weight of a solid carrier (for example finely ground kaolin).

[0430] xii) Granules (GR, FG) 0.5 to 30% by weight of the compound I according to the invention is finely ground and associated with a remaining amount of solid carrier (for example silicate) up to 100% by weight. Granulation is achieved by extrusion, spray drying or in the fluidized bed.

[0431] xiii) Ultra low volume liquid (UL) 1 to 50% by weight of the compound I according to the invention is dissolved in an organic solvent (for example an aromatic hydrocarbon) with the remaining amount up to 100% by weight.

[0432] The compositions of types i) to xi) may optionally contain further adjuvants, for example 0.1 to 1% by weight of a bactericide, 5 to 15% by weight of an antifreeze agent, 0.1 to 1% by weight of an antifoaming agent and 0.1 to 1% by weight of a coloring agent.

[0433] 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% (based on NMR spectrum).

[0434] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, antidotes) can be added to the active substance or to the composition containing it as a premix or, if appropriate, can be added only immediately before use (tank mix). These agents can be mixed with the composition according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0435] The user typically applies the compositions according to the invention from a predosage device, backpack sprayer, spray tank, spray aircraft, or irrigation system. Typically, the pesticide composition is formulated with water, buffers, and / or further adjuvants to the desired application concentration, thereby obtaining a ready-to-use spray solution or pesticide composition according to the invention. Typically, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray solution are applied per hectare of agriculturally useful area.

[0436] According to one embodiment, the individual components of the composition according to the invention, such as parts of a kit or parts of a binary or ternary mixture, are mixed by the user himself in a spray tank, and further adjuvants may be added if appropriate.

[0437] In a further embodiment, the individual or partially premixed components of the composition according to the invention, e.g. the components comprising the compound of the invention and / or the mixing partners defined above, may, if appropriate, be mixed in a spray tank by the user, and further auxiliaries and additives may be added.

[0438] In a further embodiment, the individual or partially premixed components of the composition according to the invention, e.g. the components comprising the compound of the invention and / or the mixing partners defined above, can be applied together (e.g. after a tank mix) or sequentially.

[0439] The compounds of the present invention are suitable for use in protecting crops, plants, plant propagation material, such as seeds, or the soil or water in which the plants are growing, from attack or infestation by animal pests. Accordingly, the present invention also relates to a method for protecting plants, which comprises contacting crops, plants, plant propagation material, such as seeds, or the soil or water in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the present invention.

[0440] The compounds of the present invention are 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, which comprises contacting an animal pest, its habitat, breeding ground, or food source, or a crop, plant, plant propagation material, such as a seed, or soil, or an area, material, or environment in which an animal pest is growing or may grow, with a pesticidally effective amount of a compound of the present invention.

[0441] The compounds of the present invention are effective both through contact and ingestion. Furthermore, the compounds of the present invention can be applied to all developmental stages, including eggs, larvae, pupae, and adults.

[0442] The compound of the present invention can be applied as it is or in the form of a composition containing it, as defined above.Furthermore, the compound of the present invention can be applied together with the mixing partner defined above, or in the form of a composition containing the mixture defined above.The components of the mixture can be applied simultaneously, jointly, or separately, or successively, that is, one after another, thereby forming a mixture "in situ" on desired location, for example, plant, and the order of application generally does not affect the result of control measures, as in the case of separate application.

[0443] Application can be carried out both before and after infestation by pests of crops, plants, plant propagation material, such as seeds, soil, or areas, materials or environments.

[0444] Suitable application methods include, inter alia, soil treatment, seed treatment, furrow application, and foliar application. Soil treatment methods include soil drench, drip irrigation (drip application to the soil), root, tuber, or bulb immersion, or soil injection. Seed treatment methods include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. Furrow application typically involves the steps of creating furrows in cultivated land, sowing seeds in the furrows, applying the pesticidal active compound to the furrows, and backfilling the furrows. Foliar application refers to applying the pesticidal active compound to the plant foliage, for example, with a spray device. In foliar application, it may be advantageous to use pheromones in combination with the compounds of the present invention to alter the behavior of pests. Pheromones suitable for specific crops and pests are known to those skilled in the art and are publicly available from pheromone and semiochemical databases, such as http: / / www.pherobase.com.

[0445] As used herein, the term "contact" includes both direct contact (applying the compound / composition directly onto the animal pest or plant - typically to the leaves, stems, or roots of the plant) and indirect contact (applying the compound / composition to the locus of the animal pest or plant, i.e., the habitat, breeding ground, plant, seed, soil, area, material, or environment where the pest is growing or may grow).

[0446] 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. Insects that are particularly associated with crops are typically called crop insect pests.

[0447] The term "crop" refers to both growing and harvested crops.

[0448] The term "plant" includes cereals such as durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder and sugar / sweet corn and field corn); beets, such as sugar beets or fodder beets; fruits, such as pome fruits, stone fruits, or soft fruits, for example, apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries, or gooseberries; legumes, such as beans, lentils, peas, alfalfa, or soybeans; oil plants, such as rapeseed (oilseed rape), turnips, and the like. rape), mustard, olive, sunflower, palm, cocoa bean, castor bean, oil palm, groundnut, or soybean; cucurbits, such as pumpkin, squash, cucumber, or melon; fiber plants, such as cotton, flax, hemp, or jute; citrus fruits, such as orange, lemon, grapefruit, or mandarin; vegetables, such as eggplant, spinach, lettuce (e.g., head lettuce), chicory, cabbage, asparagus, cabbage, carrot, onion, garlic, leek, tomato, potato, gourd, or sweet pepper; lauraceae, such as avocado, cinnamon, or camphor; energy plants and raw materials These include food plants such as corn, soybeans, rapeseed, sugarcane, or oil palm; tobacco; nuts such as walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grapes); hops; sweetleaf (also called stevia); rubber plants, or ornamental and forest plants such as flowers (e.g., carnations, petunias, geraniums / pelargoniums, pansies, and impatiens), shrubs, broadleaf trees (e.g., poplars), or evergreen trees such as conifers; eucalyptus; turf; lawn; grasses, for example, grasses for animal feed or ornamental use.Preferred plants include potato, sugar beet, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybean, rapeseed, legumes, sunflower, coffee or sugarcane; fruits; vines; ornamental plants; or vegetables such as cucumber, tomato, bean or pumpkin.

[0449] The term "cultivated plant" is understood to include plants that have been modified by mutagenesis or genetic engineering to provide the plant with new traits or to modify traits that are already present.

[0450] Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, as well as techniques of targeted mutagenesis to generate mutations at specific loci in the plant genome, which often use oligonucleotides or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs, or meganucleases to achieve a targeted effect.

[0451] Genetic engineering typically uses recombinant DNA technology to generate mutations in plant genomes that are not readily obtainable in natural environments through cross-breeding, mutagenesis, or natural recombination. Typically, one or more genes are integrated into a plant's genome to add or improve traits. These integrated genes are also referred to in the art as transgenes, and plants containing such transgenes are called transgenic plants. The plant transformation process typically results in several transformation events, each with a different genomic locus at which the transgene is integrated. A plant containing a particular transgene at a particular genomic locus is typically described as containing a particular "event" and is referred to by the name of the particular event. Traits introduced or modified in plants include herbicide tolerance, insect resistance, increased yield, and tolerance to biotic conditions such as drought, among others.

[0452] Herbicide resistance has been generated by using mutagenesis and by using genetic engineering. Plants that have been made tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional mutagenesis and breeding methods include plant varieties sold under the name Clearfield®. However, most herbicide-tolerant traits have been generated by the use of transgenes.

[0453] Herbicide resistance has been generated to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides (such as bromoxynil and ioxynil), sulfonylurea herbicides, ALS inhibitor herbicides, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors (such as isoxaflutole and mesotrione).

[0454] Transgenes used to confer herbicide tolerance traits include: For resistance to glyphosate, cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, and goxv247; for resistance to glufosinate, pat and bar; for resistance to 2,4-D, aad-1 and aad-12; for resistance to dicamba, dmo; for resistance to oxynil herbicides, bxn; for resistance to sulfonylurea herbicides, zm-hra, csr1-2, gm-hra, and S4-HrA; for resistance to ALS inhibitor herbicides, csr1-2; and for resistance to HPPD inhibitor herbicides, hppdPF, W336, and avhppd-03.

[0455] Transgenic corn events containing herbicide tolerance genes include, but are not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO-φ1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507, and TC6275.

[0456] Transgenic soybean events containing herbicide tolerance genes include, but are not limited to, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTφH2, W62, W98, FG72, and CV127.

[0457] Transgenic cotton events containing herbicide resistance genes include, but are not limited to, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3, and T304-40.

[0458] Transgenic canola events containing herbicide tolerance genes include, but are not limited to, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

[0459] Insect resistance has primarily been created by introducing bacterial genes encoding insecticidal proteins into plants. The most frequently used transgenes are Bacillus species toxin genes and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), and vip3Aa20. However, plant-derived genes have also been transferred to other plants, particularly genes encoding protease inhibitors such as CpTI and pinII. A further approach uses transgenes to generate double-stranded RNA that targets and downregulates insect genes in plants. An example of such a transgene is dvsnf7.

[0460] Transgenic corn events containing genes for insecticidal proteins or double-stranded RNA include, but are not limited to, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418, and MZIR098.

[0461] Transgenic soybean events containing genes for insecticidal proteins include, but are not limited to, MON87701, MON87751 and DAS-81419.

[0462] Transgenic cotton events containing genes for insecticidal proteins include, but are not limited to, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119, and SGK321.

[0463] Increased yield has been produced by increasing ear biomass using the transgene athb17 present in corn event MON87403 or by enhancing photosynthesis using the transgene bbx32 present in soybean event MON87712.

[0464] Cultivated plants with altered oil content were produced by using the transgenes gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A. Soybean events containing at least one of these genes are 260-05, MON87705, and MON87769.

[0465] Tolerance to abiotic conditions, specifically drought tolerance, has been conferred by using the transgene cspB contained in the maize event MON87460 and by using the transgene Hahb-4 contained in the soybean event IND-ΦΦ41Φ-5.

[0466] Traits are often combined by combining genes in one transformation event or by combining different events during the breeding process. Preferred combinations of traits are herbicide resistance to different groups of herbicides, insect resistance to different types of insects (especially lepidopteran resistance and coleopteran resistance), herbicide resistance and one or several types of insect resistance, herbicide tolerance and increased yield, and herbicide tolerance and tolerance to abiotic conditions.

[0467] Plants containing single or stacked traits, as well as the genes and events that confer these traits, are well known in the art. For example, detailed information about mutated or integrated genes and events can be found at the organizations International Service for the Acquisition of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and the Center for Environmental Risk Assessment (CRA). Further information on specific events and their detection methods is available from the Global Comprehensive Assessment (CERA) website at http: / / cera-gmc.org / GMCropDatabase, and for canola events MS1, MS8, RF3, GT73, MON88302, and KK179 in WO 01 / 031042, WO 01 / 041558, WO 02 / 036831, WO 11 / 153186, and WO 13 / 003558, and for cotton events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24- 236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, and 81910 are described in WO 02 / 034946, WO 02 / 100163, WO 02 / 100163, WO 03 / 013224, WO 04 / 072235, International Publication No. 04 / 039986, International Publication No. 05 / 103266, International Publication No. 05 / 103266, International Publication No. 06 / 128573, International Publication No. 07 / 017186, International Publication No. 08 / 122406, International Publication No. 08 / 151780, International Publication No. 12 / 134808,In WO 13 / 112527, the cone events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, and MON87419 are described in WO 98 / 044140 and U.S. Patent Application No. 02 / 102582. US Patent Application No. 03 / 126634, International Publication No. 04 / 099447, International Publication No. 04 / 011601, International Publication No. 05 / 103301, International Publication No. 05 / 061720, International Publication No. 05 / 059103, International Publication No. 06 / 098952, International Publication No. 06 / 039376, US Patent Application Publication No. 2007 / 292854, International Publication No. 07 / 142840, International Publication No. 07 / 140256, International Publication No. In WO 08 / 112019, WO 09 / 103049, WO 09 / 111263, WO 10 / 077816, WO 11 / 084621, WO 11 / 062904, WO 11 / 022469, WO 13 / 169923, WO 14 / 116854, WO 15 / 053998, and WO 15 / 142571, potato phenomena Regarding E12, F10, J3, J55, V11, X17, and Y9, see WO 14 / 178910, WO 14 / 178913, WO 14 / 178941, WO 14 / 179276, WO 16 / 183445, WO 17 / 062831, and WO 17 / 062825. Regarding rice events LLRICE06, LLRICE601, and LLRICE62, see WO 00 / 026345.In WO 00 / 026356 and WO 00 / 026345, soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419xDAS44406-6, and MON87751 are listed in WO 04 / 074492, WO 06 / 130436, WO 06 / 108674, and WO 06 / 108675. and WO 08 / 054747, WO 08 / 002872, WO 09 / 064652, WO 09 / 102873, WO 10 / 080829, WO 10 / 037016, WO 11 / 066384, WO 11 / 034704, WO 12 / 051199, WO 12 / 082548, WO 13 / 016527, WO 13 / 016516, and WO 14 / 201235.

[0468] The use of the compositions according to the present invention in cultivated plants can produce specific effects in cultivated plants containing specific genes or events. These effects can include changes in growth behavior or resistance to biotic or abiotic stressors. Such effects can include, inter alia, increased yield, increased resistance, or resistance to insect, nematode, fungal, bacterial, mycoplasmal, viral, or viroid pathogens, as well as early vigor, early or delayed ripening, low or high temperature tolerance, and changes in the spectrum or content of amino acids or fatty acids.

[0469] It has been found that the pesticidal activity of the compounds of the present invention can be enhanced by the insecticidal traits of modified plants.In addition, it has been found that the compounds of the present invention are suitable for preventing insects from developing resistance to the insecticidal traits or for controlling pests that have already developed resistance to the insecticidal traits of modified plants.In addition, the compounds of the present invention are suitable for controlling pests that are not effectively affected by the insecticidal traits, so that complementary insecticidal activity can be advantageously used.

[0470] The term "plant propagation material" refers to all reproductive parts of a plant, such as seeds and vegetative plant material, such as cuttings and tubers (e.g., potatoes), that can be used for plant propagation. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts, and other plant parts. It can also include seedlings and seedlings that are transplanted after germination or emergence from the soil. These plant propagation materials may be prophylactically treated with a plant protection compound either at the time of or before planting or transplanting.

[0471] The term "seed" encompasses all types of seeds and plant propagation materials, including but not limited to true seeds, seed pieces, axillary shoots, corms, bulbs, fruits, tubers, grains, cuttings, cuttings, etc., and in preferred embodiments refers to true seeds.

[0472] Generally, "pesticidally effective amount" refers to the amount of active ingredient required to achieve an observable effect on growth, including necrosis, killing, delay, prevention, and removal, destruction, or other effects that reduce the occurrence and activity of target organisms. Pesticidally effective amounts can vary with the various compounds / compositions used in the present invention. The pesticidally effective amount of a composition also varies with prevailing conditions such as the desired pesticidal effect and duration, weather, target species, location, and mode of application.

[0473] For soil treatment, furrow application, or application to pest habitats or nests, the amount of active ingredient is 2 0.0001 to 500g per 100ml 2 The average weight is 0.001 to 20g per serving.

[0474] When used to treat crop plants, for example by foliar application, the rate of application of the active ingredient of the present invention may be 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, more desirably from 10 g to 50 g per hectare, for example, from 10 g to 20 g per hectare, from 20 g to 30 g per hectare, from 30 g to 40 g per hectare, or from 40 g to 50 g per hectare.

[0475] The compound of the present invention is particularly suitable for use in seed treatment to protect seeds from insect pests, particularly soil-dwelling insect pests, and to protect the roots and shoots of the resulting seedlings from soil pests and foliar insects.Therefore, the present invention also relates to a method for protecting seeds from insects, particularly soil insects, and protecting the roots and shoots of seedlings from insects, particularly soil and foliar insects, comprising treating seeds with the compound of the present invention before sowing and / or before germination.Preferably, the protection of seedling roots and shoots is preferred.More preferably, the protection of seedling shoots is preferred from borer and sucking insects, chewing insects and nematodes.

[0476] The term "seed treatment" includes any suitable seed treatment technique known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and furrow application. Preferably, the seed treatment application of the active compound is carried out by spraying or dusting the seeds before sowing and before the emergence of the plants.

[0477] The present invention also includes seeds coated with or containing an active compound. The term "coated and / or containing" generally means that the active ingredient is mostly present on the surface of the propagation product when applied, although depending on the application method, a greater or lesser proportion of the ingredient may penetrate into the propagation product. When the propagation product is (re)planted, it may take up the active ingredient.

[0478] Suitable seeds are, for example, seeds of cereals, root crops, rapeseed, vegetables, spices, ornamental plants such as durum wheat and other wheats, barley, oats, rye, maize (fodder maize and sugar maize / sweet corn and field maize), soybeans, oil crops, brassicas, cotton, sunflowers, bananas, rice, rapeseed, turnip rape, sugar beet, fodder beet, eggplant, potatoes, grass, turf, turf, fodder grass, tomatoes, leeks, pumpkins / eggplants, cabbage, iceberg lettuce, peppers, cucumbers, melons, Brassica plants, melons, legumes, peas, garlic, onions, carrots, tuberous root plants such as potatoes, sugarcane, tobacco, grapes, petunias, geraniums / pelargoniums, pansies and impatiens.

[0479] Furthermore, the active compounds may also be used to treat seeds from plants that have been modified by mutagenesis or genetic engineering to render them resistant to the action of, for example, herbicides, fungicides or insecticides. Such modified plants are described in detail above.

[0480] Conventional seed treatment formulations include, for example, flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water-dispersible powders for slurry treatment WS, water-soluble powders SS, as well as emulsions ES and EC and gel formulations GF. These formulations can be applied to seeds in a diluted or undiluted state. Seed application is carried out before sowing, either directly on the seeds or after pre-germinating the seeds. Preferably, the formulations are applied in a germ-free manner.

[0481] The active substance concentration in the ready-to-use formulation obtainable after 2- to 10-fold dilution is preferably 0.01-60% by weight, more preferably 0.1-40% by weight.

[0482] In a preferred embodiment, a FS formulation is used for seed treatment. Typically, the FS formulation may contain 1-800 g / l of active ingredient, 1-200 g / l of surfactant, 0-200 g / l of antifreeze agent, 0-400 g / l of binder, 0-200 g / l of pigment, and up to 1 liter of solvent, preferably water.

[0483] Particularly preferred FS formulations of the compounds of the invention for seed treatment usually comprise 0.1 to 80% by weight (1 to 800 g / l) of active ingredient, 0.1 to 20% by weight (1 to 200 g / l) of at least one surfactant, for example 0.05 to 5% by weight of a wetting agent, and 0.5 to 15% by weight of a dispersing agent, up to 20% by weight, for example 5 to 20% by weight of an antifreeze agent, 0 to 15% by weight, for example 1 to 15% by weight of a pigment and / or dye, 0 to 40% by weight, for example 1 to 40% by weight of a binder (sticker / adhesive), optionally up to 5% by weight, for example 0.1 to 5% by weight of a thickener, optionally 0.1 to 2% by weight of an antifoaming agent, and optionally preservatives, for example biocides, antioxidants etc. in an amount of for example 0.01 to 1% by weight, and up to 100% by weight of fillers / vehicles.

[0484] In seed treatment, the application amount of the compound of the present invention is generally 0.1 g to 10 kg per 100 kg of seeds, preferably 1 g to 5 kg per 100 kg of seeds, more preferably 1 g to 1000 g per 100 kg of seeds, particularly preferably 1 g to 200 g per 100 kg of seeds, for example, 1 g to 100 g or 5 g to 100 g per 100 kg of seeds.

[0485] Therefore, the present invention also relates to seeds containing the compounds of the present invention or agriculturally useful salts thereof as defined herein. The amount of the compounds of the present invention or agriculturally useful salts thereof will generally vary from 0.1 g to 10 kg per 100 kg of seeds, preferably from 1 g to 5 kg per 100 kg of seeds, and particularly from 1 g to 1000 g per 100 kg of seeds. For certain crops, such as lettuce, the rate may be higher.

[0486] The compounds of the present invention may also be used to improve plant health. Accordingly, the present invention also relates to a method of improving plant health by treating the plant, plant propagation material and / or the locus in which the plant is growing or intended to grow with an effective, non-phytotoxic amount of a compound of the present invention.

[0487] As used herein, "effective and non-phytotoxic amount" means that the compound is used in an amount that allows for the desired effect to be achieved but does not cause any phytotoxic symptoms in the treated plants or plants grown from the treated propagules or treated soil.

[0488] The terms "plant" and "plant propagation material" are defined above.

[0489] "Plant health" is defined as the condition of a plant and / or its products as measured by several aspects, alone or in combination with each other, such as yield (e.g., increased biomass and / or increased content of valuable components), quality (e.g., improved content or composition of certain components or shelf life), plant vigor (e.g., improved plant growth and / or greening of leaves ("greening effect")), resistance to abiotic stress (e.g., drought) and / or biotic stress (e.g., disease), and production efficiency (e.g., harvesting efficiency, processability).

[0490] The above-identified indicators of plant health may be interdependent and may result from one another, and each indicator is defined in the art and can be determined by methods known to those skilled in the art.

[0491] The compounds of the present invention are also suitable for use against non-crop insect pests.For use against non-crop insect pests, the compounds of the present invention can be used as bait compositions, gels, general insect sprays, aerosols, ultra-low volume applications, and bed nets (impregnation or surface application).In addition, drenching and rodding methods can also be used.

[0492] As used herein, the term "non-crop insect pest" refers to a pest that is particularly associated with non-crop targets, such as an ant, termite, wasp, fly, mite, mosquito, bedbug, cricket, or cockroach.

[0493] The bait can be a liquid, solid, or semi-solid preparation (e.g., a gel). The bait used in the present composition is a product that is sufficiently attractive to insects, such as ants, termites, wasps, flies, mosquitoes, crickets, or cockroaches, to eat it. The attraction can be manipulated using feeding stimulants or sex pheromones. Food stimulants can be selected from, but are not limited to, animal and / or plant proteins (meat meal, fish meal, blood meal, insect parts, egg yolk), animal and / or plant-derived fats and oils, or monosaccharides, oligosaccharides, or polysaccharides, particularly sucrose, lactose, fructose, dextrose, glucose, starch, pectin, or molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, or insects, or specific parts thereof, can also function as feeding stimulants. Sex pheromones are known to be more insect-specific. Certain pheromones are described in the literature (eg, http: / / www.pherobase.com) and are known to those skilled in the art.

[0494] When used in bait compositions, the active ingredient typically comprises 0.001% to 15% by weight, preferably 0.001% to 5% by weight of the active compound.

[0495] Formulations of the compounds of the present invention as aerosols (e.g., spray cans), oil sprays, or pump sprays are highly suitable for professional or non-professional users to control pests such as flies, fleas, mites, bedbugs, mosquitoes, or cockroaches. Aerosol formulations preferably consist of the active compound, a solvent, and further auxiliaries such as emulsifiers, perfume oils, optionally stabilizers, and optionally propellants.

[0496] Oil spray formulations differ from aerosol formulations in that they do not use a propellant.

[0497] When used in a spray composition, the content of the active ingredient is 0.001 to 80% by weight, preferably 0.01 to 50% by weight, and most preferably 0.01 to 15% by weight.

[0498] The compounds of the present invention and their respective compositions can also be used in mosquito and fumigation coils, smoke cartridges, vaporizer plates or long-term vaporizers, as well as moss paper, moss pads or other heat-independent vaporizer systems.

[0499] Methods for controlling insect-borne infectious diseases (e.g., malaria, dengue fever, yellow fever, lymphatic filariasis and leishmaniasis) with the compounds of the present invention and their respective compositions also include treatment of surfaces in sheds and houses, air spraying, and impregnation of curtains, tents, textiles, bed nets, tsetse fly traps, etc. Insecticide compositions for application to fibers, woven fabrics, knitted goods, nonwovens, netting or foils and tarpaulins preferably comprise a mixture comprising an insecticide, optionally a repellent and at least one binder.

[0500] The compounds of the present invention and compositions thereof can be used to protect wood materials, such as trees, wooden fences, railroad ties, picture frames, artwork, and the like, as well as buildings, building materials, furniture, leather, textiles, vinyl products, electrical wires and cables, from ants, termites, and / or wood- or textile-destroying beetles, and to control ants and termites from harming crops or humans (e.g., when the pests invade homes and public facilities or nest in gardens, orchards, or parks).

[0501] 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 0.1g to 50g.

[0502] The insecticide composition used to impregnate 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.

[0503] The compounds of the present invention are particularly suitable for the effective control of animal pests, such as arthropods, gastropods, and nematodes, including, but not limited to, those listed below: Insects from the order of Lepidoptera, for example, Achroia grisella, Acleris spp., for example, A. fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp., for example, A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. spp., such as A. exclamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A. subterranea; Alabama argillacea, Aleurodicus dispersus, Alsophila pometaria, Ampelophaga rubiginosa, Amyelois transitella, Anacampsis sarcitella, Anagasta quaeniella, kuehniella, Anarsia lineatella, Anisota senatoria, Antheraea pernyi, Anticarsia (=Thermesia) spp., e.g., A. gemmatalis; Apamea spp., Aproaerema modicella, Archips spp., e.g., A. argyrospila, A.A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjugella, Argyroploce spp., Argyrotaenia spp., e.g., A. velutinana; Athetis mindara, Austroasca viridigrisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedellia spp., Bonagota salubricola salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., e.g., C. murinana, C. podana; Cactoblastis cactorum, Cadra cautella, Calingo braziliensis, Caloptilis theivora, Capua reticulana, Carposina spp. spp., for example, C. niponensis, C. sasakii; Cephus spp., Chaetocnema aridula, Cheimatobia brumata; Chilo spp., for example, C. indicus, C. suppressalis, C. partelluspartellus; Choreutis pariana, Choristoneura spp., e.g., C. conflictana, C. fumiferana, C. longicellana, C. murinana, C. occidentalis, C. rosaceana; Chrysodeixis (=Pseudoplusia) spp., e.g., C. eriosoma, C. includens; Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp. spp., Cnaphalocrocis medinalis, Cnephasia spp., Cochylis hospes, Coleophora spp., Colias eurytheme, Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Corcyra cephalonica, Crambus caliginosellus, Crambus toterellus teterrellus, Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectalis, Cydia (=Carpocapsa) spp., e.g., C. pomonella, C. latifereanalatiferreana; Dalaca noctuides, Datana integerrima, Dasychira pinicola, Dendrolimus spp., e.g., D. pini, D. spectabilis, D. sibiricus; Desmia funeralis, Diaphania spp., e.g., D. nitidalis, D. hyalinata; Diatraea grandiosella, Diatraea saccharalis, Diphthera festiva festiva, Earias spp., e.g., E. insulana, E. vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) curialis, Elasmopalpus lignosellus, Eldana saccharina, Endopiza viteana, Ennomos subsignaria, Eoreuma loftini, Ephestia spp. spp.), e.g., E. cautella, E. elutella, E. kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiliaria, Erionota thrax, Etiella spp., Eulia spp.), Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana, Faronta albilinea, Feltia spp., e.g., F. subterranean; Galleria mellonella, Gracilaria spp., Grapholita spp., e.g., G. funebrana, G. molesta, G. inopinata; Halysidota spp. spp.), Harrisina americana, Hedylepta spp., Helicoverpa spp., e.g., H. armigera (= Heliothis armigera), H. zea (= Heliothis zea); Heliothis spp., e.g., H. assulta, H. subflexa, H. virescens; Hellula spp., e.g., H. undalis, H. logatarisrogatalis; Helocoverpa gelotopoeon, Hemileuca oliviae, Herpetogramma licarsisalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homoeosoma electellum, Homona magnanima, Hypena scabra, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Kakivoria flavofasciata), Keiferia lycopersicella,. Lambdina fiscellaria fiscellaria, Lambdina fiscellaria lugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivora glycinivorella, Lerodea eufala, Leucinodes orbonalis, Leucoma salicis, Leucoptera spp., e.g., L. coffeella, L. scitella; Leuminivora lycinivorella, Lithocolletis blancardella, Lithophane antennata, Llattia octo (= Amyna axis), Lobesia botrana, Lophocampa spp., Loxagrotis albicosta, Loxostege spp., e.g., L. sticticalis, L. cereralis; Lymantria spp., e.g., L. dispar, L. monacha; peach leafminer Lyonetia clerkella, Lyonetia prunifoliella, Malacosoma spp., e.g., M. americanum, M. californicum, M. constrictum, M. neustria; Mamestra spp., e.g., M. brassicabrassicae, M. configurata; Mamstra brassicae, Manduca spp., e.g., M. quinquemaculata, M. sexta; Marasmia spp., Marmara spp., Maruca testulalis, Megalopyge lanata, Melanchra picta, Melanitis leda, Mocis spp., e.g., M. lapites, M. repanda; Mocis latipes, Monochroa fragaria fragariae, Mythimna separata, Nemapogon cloacella, Neoleucinodes elegantalis, Nepytia spp., Nymphula spp., Oiketicus spp., Omiodes indicata, Omphisa anastomosalis, Operophtera brumata, Orgyia pseudotsugata, Oria spp., Orthaga thyrisalis, Ostrinia spp. spp.), e.g., O. nubilalis; Oulema oryzae, Paleacrita vernata, Panolis flammea, Parnara spp.), Papaipema nebris, Papilio cresphontes, Paramyelois transitella, Paranthrene regalis, Paysandisia archon, Pectinophora spp., e.g., P. gossypiella; Peridroma saucia, Perileucoptera spp., e.g., P. coffeella; Phalera bucephala, Phryganidia californica, Phthorimaea spp. spp., for example, P. operculella; Phyllocnistis citrella; Phyllonorycter spp., for example, P. blancardella, P. crataegella, P. issikii, P. ringoniella; Pieris spp., for example, P. brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra, Platynota spp. spp.), e.g., P. flavedana, P. idaeusalis, P. struttanastultana; Platyptilia carduidactyla, Plebejus argus, Plodia interpunctella, Plusia spp., Plutella maculipennis, Plutella xylostella, Pontia protodica, Prays spp., Prodenia spp., Proxenus lepigone, Pseudaletia spp., e.g., P. sequax, P. unipuncta; Pyrausta nubilalis nubilalis, Rachiplusia nu, Richia albicosta, Rhizobius ventralis, Rhyacionia frustrana, Sabulodes aegrotata, Schizura concinna, Schoenobius spp., Schreckensteinia festaliella, Scirpophaga spp., e.g., S. incertulas, S. innotata; Scotia segetum, Sesamia spp. spp.), such as S. inferens, Seudyra subflava, Sitotroga cerealella, Sparganothis pilleriana, Spironota lechriaspis, S. ocellana,ocellana, Spodoptera (=Lamphygma) spp., e.g., S. cosmoides, S. eridania, S. exigua, S. frugiperda, S. latisfascia, S. littoralis, S. litura, S. omithogalli; Stigmella spp., Stomopteryx subsecivella, Strymon bazochii, Sylepta derogata, Synanthedon spp. spp., e.g., S. exitiosa, Tecia solanivora, Telehin licus, Thaumatopoea pityocampa, Thaumatotibia (=Cryptophlebia) leucotreta, Thaumetopoea pityocampa, Thecla spp., Theresimima ampelophaga, Thyrinteina spp., Tildenia inconspicuella, Tinea spp. spp., for example, T. cloacella, T. pellionella; Tineola bisselliella, Tortrix spp., for example, T. viridana; Trichophaga tapetzella, Trichoplusia spp., for example, T.ni); Tuta (=Scrobipalpula) absoluta, Udea spp., e.g., U. rubigalis, U. rubigalis; Virachola spp., Yponomeuta padella, and Zeiraphera canadensis; Insects from the order Coleoptera, for example, Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp., for example, A. anxius, A. planipennis, A. sinuatus; Agriotes spp., for example, A. fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus diaperinus, Amphimarus solstitialis, Anisandrus dispar, Anisoplia austriaca, Anobium punctatum, Anomala corpulenta, Anomala rufocuprea, Anoplophora spp., e.g., A. glabripennis; Anthonomus spp., e.g., A. eugenii, A. grandis, A. pomorum; Anthrenus spp. spp.), Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidalis, Atomaria spp., e.g., A. linearis; Attagenus spp.), cucumber beetle (Aulacophora femoralis), Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as B. lentis, B. pisorum, B. rufimanus; Byctiscus betulae, Callidiellum rufipenne, Callopistria floridensis, azuki bean weevil (Callosobruchus chinensis), Cameraria ohridella, turtle beetle (Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp., e.g., C. assimilis, C. napi; Chaetocnema tibialis, Cleonus mendicus, Conoderus spp., e.g., C. vespertinus; Conotrachelus nenuphar, Cosmopolites spp., Costelytra zealandica, Crioceris asparagi asparagi, Cryptolestes ferrugineus, Cryptorhynchus lapathi, Ctenicera spp. e.g. C. destructor; Curculio spp., Cylindrocopturus spp.), Cyclocephala spp., Dactylispa balyi, Dectes texanus, Dermestes spp., Diabrotica spp., e.g., D. undecimpunctata, D. speciosa, D. longicornis, D. semipunctata, D. virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladistipus armigera, Diloboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis), Enaphalodes rufulus, Epilachna spp., e.g., E. varivestis, E. vigintioctomaculata; Epitrix spp., e.g., E. hirtipennis, E. simillaris;similaris; Eutheola humilis, Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera species spp., e.g., H. brunneipennis, H. postica; Hypomeces squamosus, Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., e.g., L. bilineata, L. melanopus; Leptinotarsa spp. spp., for example, L. decemlineata; Leptispa pygmaea, Limonius californicus, Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp., for example, L. bournois;bruneus; Liogenys fuscus, Macrodactylus spp., e.g., M. subspinosus; Maladera matrida, Megaplatypus mutates, Megascelis spp., Melanotus communis, Meligethes spp., e.g., M. aeneus; Melolontha spp., e.g., M. hippocastani, M. melolontha; Metamasius hemipterus, Microtheca spp. Migdolus spp., e.g., M. fryanus, Monochamus spp., e.g., M. alternatus; Naupactus xanthographus, Niptus hololeucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus sulcatus sulcatus, Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon spp., e.g., P. brassicae, P. cochlearia, P.cochleariae; Phoracantha recurva, Phyllobius pyri, Phyllopertha horticola, Phyllophaga spp., e.g., P. helleri; Phyllotreta spp., e.g., P. chrysocephala, P. nemorum, P. striolata, P. vittula; Phyllopertha horticola, Popillia japonica, Premnotrypes spp., Psacothea hilaris hilaris), Psylliodes chrysocephala,. Prostephanus truncates, Psylliodes spp., Ptinus spp., Pulga saltona, Rhizopertha dominica, Rhynchophorus spp., e.g., R. billineatus, R. ferrugineus, R. palmarum, R. phoenicis, R. vulneratus; Saperda candida, Scolytus schevyrewi, Scyphophorus aquapunctatus acupunctatus, Sitona lineatus, Sitophilus spp., e.g., S. granaria, S. oryzae, S. zeamais; Sphenophorus spp., e.g., S. levis; Stegobium paniceum, Sternechus spp., e.g., S. subsignatus; Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor molitor, Tenebrioides mauretanicus, Tribolium spp., e.g., T. castaneum; Trogoderma spp., Tychius spp., Xylotrechus spp., e.g., X. pyrhoderus; and Zabrus spp., e.g., Z.tenebrioides (Z. tenebrioides);. Insects from the order of Diptera, for example, Aedes spp., for example, A. aegypti, A. albopictus, A. vexans; Mexican fruit fly (Anastrepha ludens), Anopheles spp. spp., such as A. albimanus, A. crucians, A. freeborni, A. gambiae, A. leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A. sinensis; Bactrocera invadens, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata capitata, Chrysomyia spp., e.g., C. bezziana, C. hominivorax, C. macellaria; Chrysops atlanticus, Chrysops discalis, Chrysops silacea, Cochliomyia spp., e.g., C. hominivorax; Contarinia spp., e.g., C. sorghicola; Cordylobia anthropophaga, Culex spp. spp.), e.g., C. nigripalpus, C. pipiens, C. quinquefasciatus, C. tarsalis, C.tarsalis, C. tritaeniorhynchus; Culicoides furens, Culiseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Dasineura oxycoccana, Delia spp., e.g., D. antique, D. coarctata, D. platura, D. radicum; Dermatobia hominis hominis, Drosophila spp., for example, D. suzukii, Fannia spp., for example, F. canicularis; Gastraphilus spp., for example, G. intestinalis; Geomyza tipunctata, Glossina spp., for example, G. fuscipes, G. morsitans, G. palpalis, G. tachinoides; Haematobia irritans, Haplodiplosis equestris equestris, Hippelates spp., Hylemyia spp., for example, H. platura; Hypoderma spp., for example, H. lineata; Hyppobosca spp.), Hydrellia philippina, Leptoconops torrens, Liriomyza spp., e.g., L. sativae, L. trifolii; Lucilia spp., e.g., L. caprina, L. cuprina, L. sericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp., e.g., M. destructor; Musca spp. spp., e.g., M. autumnalis, M. domestica; Muscina stabulans, Oestrus spp., e.g., O. ovis; Opomyza florum, Oscinella spp., e.g., O. frit; Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentipes, Phorbia spp. spp., for example, P. antiqua, P. brassicae, P. coarctata; Phytomyza gymnostoma, Prosimulium mixtum, Psila rosae, Psorophora columbiae, Psorophora discolor, Rhagoletis spp., for example, R. cerasi, R. cingulate, R. indifferens, R. mendax, R.R. pomonella; Riverlia quadrifasciata; Sarcophaga spp., e.g., S. haemorrhoidalis; Simulium vittatum, Sitodiplosis mosellana; Stomoxys spp., e.g., S. calcitrans; Tabanus spp., e.g., T. atratus, T. bovinus, T. lineola, T. similis; Tannia spp., Thecodiplosis japonensis japonensis, Tipula oleracea, Tipula paludosa, and Wohlfahrtia spp.; Insects from the order Thysanoptera, for example, Baliothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp., for example, F. fusca, F. occidentalis, F. tritici; Heliothrips spp., Hercinothrips femoralis, Kakothrips spp. spp., Microcephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, Rhipiphorothrips cruentatus, Scirtothrips spp., e.g., S. citri, S. dorsalis, S. perseae; Stenchaetothrips spp., Taeniothrips cardamoni, Taeniothrips inconsequence inconsequens), Thrips spp., e.g., T. imagines, T. hawaiiensis, T. oryzae, T. palmi, T. parvispinus, T. tabaci; Insects from the order of the Hemiptera, for example, Acizzia jamatonica, Acrosternum spp., for example, A. hilare; Acyrthosipon spp., for example, A. onobrychis, A. pisum; Adelges laricis, Adelges tsugae, Adelphocoris spp., for example, A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp. spp., Aulacorthum solani, Aleurocanthus woglumi, Aleurodes spp., Aleurodicus disperses, Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp., e.g., A. craccivora, A. fabae, A. forbesi, A. gossypii, A. grossulariae, A. maidiradicis, A. pomi, A. sambuci, A. schneideri, A. spiraecola, A.spiraecola; Arboridia apicalis, Arilus critatus, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacaspis yasumatsui, Aulacorthum solani, Bactericera cockerelli (Paratrioza cockerelli), Bemisia spp., e.g., B. argentifolii, B. tabaci (Aleurodes tabaci), tabaci); Blissus spp., for example, B. leucopterus; Brachycaudus spp., for example, B. cardui, B. helichrysi, B. persicae, B. prunicola; Brachycolus spp., Brachycorynella asparagi, Brevicoryne brassicae; Cacopsylla spp., for example, C. fulguralis, C. pyricola, Psylla piri); Calligypona marginata, Calocoris spp., Campylomma livida, Capitophorus horni, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp.), Ceratovacuna lanigera, Ceroplastes ceriferus, Cerosipha gossypii, Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Cimex species spp., e.g., C. hemipterus, C. lectularius; Coccomytilus halli; Coccus spp., e.g., C. hesperidum, C. pseudomagnoliarum; Corythucha arcuata, Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum, Cryptomyzus ribis, Ctenarytaina spathulata spatulata, Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeurodes spp., for example, D. citrifolii; Dalbulus maidis, Diaphorina spp., for example, D. citri; Diaspis spp., for example, D. bromeliads (D.bromeliae; Dichelops furcatus, Diconocoris hewetti, Doralis spp., Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha spp., Dysaphis spp., e.g., D. plantaginea, D. pyri, D. radicola; Dysaulacorthum pseudosolani, Dysdercus spp. spp., e.g., D. cingulatus, D. intermedius; Dysmicoccus spp., Edessa spp., Geocoris spp., Empoasca spp., e.g., E. fabae, E. solana; Epidiaspis leperii; Eriosoma spp., e.g., E. lanigerum, E. pyricola; Erythroneura spp., Eurygaster spp. spp., for example, E. integriceps; Euscelis bilobatus, Euschistus spp., for example, E. heros, E. impictiventris, E. servus; Fiorinia theae, Geococcus coffeae, Glycaspis brimblecombei, Halyomorpha spp., for example, H. halyshalys; Heliopeltis spp., Homalodisca vitripennis (=H. coagulata), Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, Icerya spp., e.g., I. purchase; Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanoideus flossissimus floccissimus, Lepidosaphes spp., e.g., L. ulmi; Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp., e.g., L. hesperus, L. lineolaris, L. pratensis; Maconellicoccus hirsutus, Marchalina hellenica, Macropes excavatus, Macrosiphum spp. spp.), e.g., M. rosae, M. avenae, M. euphorbiae; Macrosteles quadrilineatus, Mahanarva fimbriolata, etc. Megacopta cribraria, Broad bean aphid (Megoura viciae), Melanaphis pyrarius, Melanaphis sacchari, Melanocallis (=Tinocallis) caryaefoliae, Metcafiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzocallis coryli, Murgantia spp., Myzus spp. spp., e.g., M. ascalonicus, M. cerasi, M. nicotianae, M. persicae, M. varians; Nasonovia ribis-nigri, Neotoxoptera formosana, Neomegalotomus spp., Nephotettix spp., e.g., N. malayanus, N. nigropictus, N. parvus, N. virescens; Nezara spp. spp., e.g., N. viridula; Nilaparvata lugens, Nysius huttoni; Oebalus spp., e.g., O. pugnax; Oncometopia spp.), Orthezia praelonga, Oxycaraenus hyalinipennis, Parabemisia myricae, Parlatoria spp., Parthenolecanium spp., e.g., P. corni, P. persicae; Pemphigus spp., e.g., P. bursarius, P. populivenae; Peregrinus maidis, Perkinsiella saccharicida, Phenacoccus spp. spp., for example, P. aceris, P. gossypii; Phloeomyzus passerinii, Phorodon humuli; Phylloxera spp., for example, P. devastatrix, Piesma quadrata; Piezodorus spp., for example, P. guildinii; Pinnaspis aspidistrae; Planococcus spp., for example, P. citri, P. ficus; Prosapia bicincta bicincta, Protopulvinaria pyriformis, Psallus seriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp., e.g., P. comstocki; Psylla spp., e.g., P. malimali; Pteromalus spp., Pulvinaria amygdali, Pyrilla spp., Quadraspidiotus spp., e.g., Q. perniciosus; Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp. spp., e.g., R. pseudobrassicas, R. insertum, R. maidis, R. padi; Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mali, Scaptocoris spp., Scaphoides titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp. spp.), Selenaspidus articulatus, Sitobion avenae, Sogata spp.), Sogatella furcifera, Solubea insularis, Spisstilus festinus (=Stictocephala festina), Stephanitis nashi, Stephanitis pyrioides, Stephanitis takeyai, Tenalapha malayensis, Tetraleurodes perseae, Therioaphis maculate, Thyanta species spp., for example, T. accerra, T. perditor; Tibraca spp., Tomaspis spp., Toxoptera spp., for example, T. aurantii; Trialeurodes spp., for example, T. abutilonea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. spp.), such as U. citri, U. yanonensis; and Viteus vitifolii. Insects from the order Hymenoptera, for example, Acanthomyops interjectus, Athalia rosae, Atta spp., for example, A. capiguara, A. cephalotes, A. cephalotes, A. laevigata, A. robusta, A. sexdens, A. texana, Bombus spp., Brachymyrmex spp., Camponotus spp. spp., e.g., C. floridanus, C. pennsylvanicus, C. modoc; Cardiocondyla nuda, Chalibion spp., Crematogaster spp., Dasymutilla occidentalis, Diprion spp., Dolichovespula maculata, Dorymyrmex spp., Dryocosmus kuriphilus, Formica spp., Hoplocampa spp. spp., for example, H. minuta, H. testudinea; Iridomyrmex humilis, Lasius spp., for example, L. niger, Linepithema humile, Liometopum spp., Leptocybe invasa, Monomorium spp., for example, M. pharaonispharaonis, Monomorium, Nylandria fulva, Pachycondyla chinensis, Paratrechina longicornis, Paravespula spp., e.g., P. germanica, P. pennsylvanica, P. vulgaris; Pheidole spp., e.g., P. megacephala; Pogonomyrmex spp., e.g., P. barbatus, P. californicus, Polistes rubiginosa rubiginosa, Prenolepis impairs, Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus, Solenopsis spp. e.g., S. geminata, S. invicta, S. molesta, S. richteri, S. xyloni, Sphecius speciosus, Sphex spp., Tapinoma spp. spp., for example, T. melanocephalum, T. sessile; Tetramorium spp., for example, T. caespitum, T. bicarinatum; Vespa spp., for example, V. crabro; Vespula spp., for example, V. squamosaar;squamosal); Wasmannia auropunctata, Xylocopa sp;. Insects from the order Orthoptera, for example, Acheta domesticus, Calliptamus italicus, Chortoicetes terminifera, Ceuthophilus spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp., for example, G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis, Kraussaria angulifera, Locusta spp., e.g., L. migratoria, L. pardalina; Melanoplus spp., e.g., M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M. spretus; Nomadacris septemfasciata, Oedaleus senegalensis, Scapteriscus spp., Schistocerca spp. spp.), such as S. americana, S. gregaria, Stemopelmatus spp., Tachycines asynamorus, and Zonozerus variegatus;Pests from the class of the Arachnida, for example the Acari, for example the following families: Argasidae, Ixodidae and Sarcoptidae, for example Amblyomma spp. (e.g. A. americanum, A. variegatum, A. maculatum), Argas spp. (e.g. A. persicu), Boophilus spp. (e.g. B. annulatus, B. decoloratus, B. microplus), Dermacentor spp. spp., for example, D. silvarum, D. andersoni, D. variabilis, Hyalomma spp., for example, H. truncatum, Ixodes spp., for example, I. ricinus, I. rubicundus, I. scapularis, I. holocyclus, I. pacificus, Rhipicephalus sanguineus, Ornithodorus spp. spp., for example, O. moubata, O. hermsi, O. turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp., for example, P. ovis, Rhipicephalus spp., for example, R. sanguineus, R. appenziculatus,appendiculatus, Rhipicephalus evertsi, Rhizoglyphus spp., Sarcoptes spp., for example, S. Scabiei; and Family Eriophyidae, for example, Aceria spp., for example, A. sheldoni, A. anthocoptes, Acallitus spp., Aculops spp., for example, A. lycopersici, A. pelekassi; Aculus spp. spp., for example, A. schlechtendali; Colomerus vitis, Epitrimerus pyri, Phyllocoptruta oleivora; Eriophytes ribis and Eriophyes spp., for example, Eriophyes sheldoni; Family Tarsonemidae, for example, Hemitarsonemus spp., Phytonemus pallidus and Polyphagotarsonemus latus, Stenotarsonemus spp. spp., Steneotarsonemus spinki; Family Tenuipalpidae, for example, Brevipalpus spp., for example, B. phoenicis; Family Tetranychidae, for example, Eotetranychus spp., Eutetranychus spp., Oligonychus spp.), Petrobia latens, Tetranychus spp., for example, T. cinnabarinus, T. evansi, T. kanzawai, T. pacificus, T. phaseulus, T. telarius, and T. urticae; Bryobia praetiosa; Panonychus spp., for example, P. ulmi, P. citri; Metatetranychus spp., and Oligonychus spp. spp., for example, O. pratensis, O. perseae, Vasates lycopersici; Raoiella indica, Family Carpoglyphidae, for example, Carpoglyphus spp.; Penthaleidae spp., for example, Halotydeus destructor; Family Demodicidae and species thereof, for example, Demodex spp.; Family Trombicidea, for example, Trombicula spp. spp.); Family Macronyssidae, for example Ornothonyssus spp.; Family Pyemotidae, for example, Pyemotes tritici; Tyrophagus putrescentiae; Family Acaridae, for example, Acarus siro; Family Araneida, for example, Latrodectus mactans, Tegenaria agrestis, Chiracanthium species, Lycosa species, Achaearanea tepidariorum and Loxosceles reclusa; Pests from the phylum Nematoda, for example, plant-parasitic nematodes, for example, root-knot nematodes, Meloidogyne spp., for example, M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp., for example, G. rostochiensis; Heterodera spp., for example, H. avenae, H. glycines, H. schachtii, H. trifolii; seed-knot nematodes nematodes, Anguina spp.; stem and foliar nematodes, Aphelenchoides spp., e.g., A. besseyi; sting nematodes, Belonolaimus spp., e.g., B. longicaudatus; pine nematodes, Bursaphelenchus spp., e.g., B. lignicolus, B. xylophilus; ring nematodes, Criconema spp., Criconemella spp. spp., for example, C. xenoplax and C. ornata; and Criconemoides spp., for example, Criconemoides informis; Mesocriconema spp.; Stem and bulb nematodes, Ditylenchus spp., for example, D. destorctol.destructor, D. dipsaci; Awl nematodes, Dolichodorus spp.; Spiral nematodes, Heliocotylenchus multicinctus; Sheath and sheathoid nematodes, Hemicycliophora spp. and Hemicriconemoides spp.; Hirshmanniella spp.; Lance nematodes, Hoploaimus spp.; False rootknot nematodes, Nacobbus spp.; Needle nematodes nematodes, Longidorus spp., for example, L. elongatus; Lesion nematodes, Pratylenchus spp., for example, P. brachyurus, P. neglectus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radopholus spp., for example, R. similis; Rhadopholus spp.; Rhodopholus spp.; Reniform nematodes, Rotylenchus spp., e.g., R. robustus, R. reniformis; Scutellonema spp.; Stubby-root nematodes, Trichodorus spp., e.g., T. obtusus, T. primitiveis;primitivus; Paratrichodorus spp., e.g., P. minor; Stunt nematodes, Tylenchorhynchus spp., e.g., T. claytoni, T. dubius; Citrus nematodes, Tylenchulus spp., e.g., T. semipenetrans; Dagger nematodes, Xiphinema spp.; and other plant-parasitic nematode species. Insects from the order Blattodea, for example Macrotermes spp., for example M. natalensis; Cornitermes cumulans, Procornitermes spp., Globitermes sulfureus, Neocapritermes spp., for example N. opacus, N. parvus; Odontotermes spp., Nasutitermes spp., for example N. corniger; Coptotermes spp. spp., for example, C. formosanus, C. gestroi, C. acinaciformis; Reticulitermes spp., for example, R. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R. lucifugus, R. virginicus; Heterotermes spp., for example, H. aureus, H. longiceps, H. tenuis; Cryptotermes spp. spp., for example, C. brevis, C. cavifrons; Incisitermes spp., for example, I. minor, I. Snyder; Marginitermes hubbardi, Kalotermes flavicollis, Neotermes spp., for example, N. castaneuscastaneus, Zootermopsis spp., e.g., Z. angusticollis, Z. nevadensis, Mastotermes spp., e.g., M. darwiniensis; Blatta spp., e.g., B. orientalis, B. lateralis; Blattella spp., e.g., B. asahinae, B. germanica; Leucophaea maderae, Panchlora nivea, Periplaneta spp. spp.), such as P. americana, P. australasiae, P. brunnea, P. fuligginosa, P. japonica; Supella longipalpa, Parcoblatta pennsylvanica, Eurycotis floridana, Pycnoscelus surinamensis, etc. Insects from the order of the Siphonoptera, for example, Cediopsylla simples, Ceratophyllus spp., Ctenocephalides spp., for example, C. felis, C. canis, Xenopsylla cheopis, Pulex irritans, Trichodectes canis, Tunga penetrans, and Nosopsyllus fasciatus, Insects from the order Thysanura, such as Lepisma saccharina, Ctenolepisma urbana, and Thermobia domestica, Pests from the class Chilopoda, for example, Geophilus spp., Scutigera spp., for example, Scutigera coleoptrata; Pests from the class Diplopoda, for example, Blaniulus guttulatus, Julus spp., Narceus spp., Pests from the class of the Symphyla, for example, Scutigerella immaculata, Insects from the order Dermaptera, for example, Forficula auricularia, Insects from the order of the Collembola, for example, Onychiurus spp., for example, Onychiurus armatus; Pests from the order Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber, Insects from the order of the Phthiraptera, for example, Damalinia spp., Pediculus spp., for example, head louse (Pediculus humanus capitis), body louse (Pediculus humanus corporis), Pediculus humanus humanus; pubic louse (Pthirus pubis), Haematopinus spp., for example, cow louse (Haematopinus eurysternus), pig louse (Haematopinus suis); Linognathus spp., for example, cow louse (Linognathus vituli); cow louse (Bovicola bovis), chicken body louse (Menopon gallinae), chicken body louse (Menacanthus stramineus) and hairy cow louse (Solenopotes capillatus), Trichodectes spp., Further examples of pest species which may be controlled by the compounds of formula (I) include: from the phylum Mollusca, class Bivalvia, for example, Dreissena spp.; from the class Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea canaliclata, Succinea spp. spp.; from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Ancylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp. spp.), Dicrocoelium spp.), Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., e.g., Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp. spp.), Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercora lis, Stronyloides spp.), Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.

[0504] The compounds of the present invention are suitable for use in treating or protecting animals from parasitic infestation or infection. Accordingly, the present invention also relates to the use of the compounds of the present invention for the manufacture of a medicament for treating or protecting animals from parasitic infestation or infection. Furthermore, the present invention relates to a method for treating or protecting animals from parasitic infestation and infection, comprising the step of orally, topically, or parenterally administering or applying to an animal a parasiticidally effective amount of a compound of the present invention.

[0505] The present invention also relates to non-therapeutic uses of the compounds of the present invention for treating or protecting animals against parasitic infestation and infection. Furthermore, the present invention relates to a non-therapeutic method of treating or protecting animals against parasitic infestation and infection, which method comprises applying to a locus thereof a parasiticidally effective amount of a compound of the present invention.

[0506] The compounds of the present invention are further suitable for use in combating or controlling parasites in and on animals. Additionally, the present invention relates to a method of combating or controlling parasites in and on animals, comprising the step of contacting the parasite with a parasiticidally effective amount of a compound of the present invention.

[0507] The present invention also relates to non-therapeutic uses of the compounds of the present invention for controlling or combating parasites. Furthermore, the present invention relates to a non-therapeutic method of combating or controlling parasites, which method comprises applying to a locus a parasiticidally effective amount of a compound of the present invention.

[0508] The compounds of the present invention can be effective by both contact (via soil, glass, walls, bed nets, carpets, blankets, or animal parts) and ingestion (e.g., bait). Furthermore, the compounds of the present invention can be applied to any and all stages of development.

[0509] The compounds of the present invention can be applied as such or in the form of a composition containing the compounds of the present invention.

[0510] The compounds of the invention can be applied in the form of compositions containing or together with mixing partners acting against pathogenic parasites, for example synthetic coccidiosis compounds, polyether antibiotics such as amprolium, robenidin, toltrazuril, monensin, salinomycin, maduramicin, lasalocid, narasin or semduramicin, or other mixing partners as defined above.

[0511] The compounds of the invention and compositions containing them can be applied orally, parenterally, or topically, for example, transdermally. The compounds of the invention can be effective systemically or non-systemically.

[0512] Application can be carried out prophylactically, therapeutically or non-therapeutically. Furthermore, application can be carried out prophylactically where an infestation of the parasite is expected.

[0513] As used herein, the term "contact" includes both direct contact (applying a compound / composition directly to a parasite (including or excluding direct application to an animal, e.g., in the latter case, application to its habitat)) and indirect contact (applying a compound / composition to the parasite's habitat). Contact with a parasite via application to the parasite's habitat is an example of a non-therapeutic use of a compound of the invention.

[0514] The term "habitat" means the habitat, food source, breeding ground, area, material or environment in which a parasite lives or can live outside an animal.

[0515] As used herein, the term "parasite" includes endoparasites and ectoparasites. In some embodiments of the present invention, endoparasites are preferred. In other embodiments, ectoparasites are preferred. Infestations of warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, bot flies, pediculosis flies, stable flies, blowflies, flies, myiasis fly larvae, chiggers, black flies, mosquitoes, and fleas.

[0516] The compounds of the present invention are useful, inter alia, for combating parasites of the following orders and species, respectively: Fleas (order Siphonaptera, e.g., Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus); cockroaches (order Blattaria, suborder Blattodea), e.g., Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis; flies and mosquitoes (Diptera), such as Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles flehbornii freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicinavicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex kwinkwefaskiatus quinquefasciatus, Culex tarsalis, Culiseta inornata, Culex melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates species spp.), Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericatasericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Musca stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinu, Tabanus atratus, Tabanus lineola, and Tabanus similis; lice (order Phthiraptera) such as Pediculus humanus capitis, Pediculus humanus humanus, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Chicken lice (Menopon gallinae), Chicken lice (Menacanthus stramineus and woolly cow lice (Solenopotes capillatus); ticks and parasitic mites (Parasitiformes): ticks (Ixodida, e.g., Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Ixodespacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Amblyomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), such as Ornithonyssus bacoti, Dermacentor gallinae, gallinae; Actinedida (suborder Prostigmata) and Acaridida (suborder Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp. spp.), Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp.Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius spp., Panstrongylus spp., and Arilus critatus; Anoplurida, e.g., Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp. spp., and Solenopotes spp.; Mallophagida (suborders Arnblycerina and Ischnocerina), for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.; phylum Nematoda, Roundworms Nematoda: Wipeworms and Trichinosis (Trichosyringida), for example, Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp.; Rhabditida, for example, Rhabditis spp., Strongyloides spp., Helicephalobus spp.spp.; Strongylida, e.g., Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (hookworms), Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp. spp.), Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophyma renale; intestinal roundworms (order Ascaridida) such as Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi; Camallanida, for example, Dracunculus medinensis (guinea worm); Spirurida, for example, Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.; Thorny headed worms (Acanthocephala), e.g., Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp.Planarians (Plathelminthes): Flukes (Trematoda), for example, Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp. spp.; Cercomeromorpha, in particular Cestoda (Tapeworms), for example Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp. spp.), Anoplocephala spp., and Hymenolepis spp.

[0517] As used herein, the term "animal" includes warm-blooded animals (including humans) and fish. Mammals such as cattle, sheep, pigs, 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, including freshwater and saltwater fish such as trout, carp and eels, are preferred. Domestic animals such as dogs or cats are particularly preferred.

[0518] Generally, "parasiticidally effective amount" refers to the amount of active ingredient required to achieve an observable effect on growth, including necrosis, killing, delay, prevention, and removal, destruction, or other effects that reduce the occurrence and activity of target organisms. The parasiticidally effective amount can vary depending on the various compounds / compositions used in the present invention. The parasiticidally effective amount of the mixture / composition also varies depending on general conditions such as the desired parasiticidal effect and duration, target species, and application mode.

[0519] Generally, it is advantageous to apply the compounds of the invention 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.

[0520] For oral administration to warm-blooded animals, the compounds of Formula I can be formulated as animal feed, animal feed premixes, animal feed concentrates, pills, liquids, pastes, suspensions, drenches, gels, tablets, boluses, and capsules. Additionally, the compounds of Formula I may be administered to animals in their drinking water. For oral administration, the selected dosage form should provide the animal with 0.01 mg to 100 mg of the compound of Formula I per kg of animal body weight per day, preferably 0.5 mg to 100 mg per kg of animal body weight per day.

[0521] Alternatively, the compound of Formula I can be administered to animals parenterally (e.g., by intraruminal, intramuscular, intravenous, or subcutaneous injection). The compound of Formula I can be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compound of Formula I can be formulated into an implant for subcutaneous administration. In addition, the compound of Formula I can be administered transdermally to animals. For parenteral administration, the selected dosage form should provide the animal with 0.01 mg to 100 mg of the compound of Formula I per kg of animal body weight per day.

[0522] The compounds of formula I can 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 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 the compound of formula I. In addition, the compounds of formula I can be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

[0523] A suitable preparation is as follows: solutions, such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pour-on formulations, gels; - emulsions and suspensions for oral or transdermal administration; semi-solid preparations; - formulations in which the active compound is processed into an ointment base or an oil-in-water or water-in-oil emulsion base; - solid preparations, such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.

[0524] Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding additional auxiliary substances such as acids, bases, buffer salts, preservatives, and solubilizers. Suitable auxiliary substances for injection solutions are known in the art. The solution is filtered and filled aseptically.

[0525] Oral solutions are administered directly, while concentrates are administered orally after pre-dilution to the concentration required for use. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, but sterilization is not required.

[0526] Solutions for epicutaneous application are dropped, spread, rubbed, sprinkled or sprayed onto the skin. Solutions for epicutaneous application are prepared according to the state of the art and according to the methods described above for injection solutions, but sterilization is not essential.

[0527] The gel is applied or spread on the skin or injected into a body cavity. The gel is prepared by treating a solution prepared as described for the injection solution with sufficient thickening agent to obtain a clear material with an ointment-like consistency. Suitable thickening agents are known in the art.

[0528] 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. If appropriate, other auxiliaries are added, such as colorants, bioabsorption promoters, antioxidants, light stabilizers, and adhesives. Suitable such auxiliaries are known in the art.

[0529] Emulsions can be administered orally, transdermally, or as an injection. Emulsions are either water-in-oil or oil-in-water. They are prepared by dissolving the active compound in either a hydrophobic or hydrophilic phase, and homogenizing it with the solvent of the other phase using a suitable emulsifier, and if appropriate, other auxiliaries such as colorants, absorption promoters, preservatives, antioxidants, light stabilizers, and viscosity enhancers. Suitable hydrophobic phases (oils), hydrophilic phases, emulsifiers, and other auxiliaries for emulsions are known in the art.

[0530] Suspensions can be administered orally or topically / transdermally. They are prepared by suspending the active compound in a suspending agent, optionally with other auxiliaries, such as wetting agents, coloring agents, bioabsorption promoters, preservatives, antioxidants, and light stabilizers. Suitable suspending agents for suspensions and other suitable auxiliaries, including wetting agents, are known in the art.

[0531] Semisolid preparations can be administered orally or topically / transdermally. They differ from the suspensions and emulsions described above only in their relatively high viscosity.

[0532] For the production of solid preparations, the active compound is mixed with suitable excipients and, if appropriate, with the addition of auxiliaries to give the desired form. Suitable auxiliaries for this purpose are known in the art.

[0533] The compositions that can be used in the present invention can generally contain about 0.001 to 95% of the compound of the present invention.

[0534] 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.

[0535] The preparations, which are diluted before use, contain the compound acting against ectoparasites in a concentration of 0.5 to 90% by weight, preferably 1 to 50% by weight.

[0536] Furthermore, the preparation comprises 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.

[0537] Topical application can be achieved with compound-containing shaped articles such as collars, medallions, ear tags, bands for fastening to body parts, and adhesive strips and foils.

[0538] Generally, it is advantageous to apply solid formulations which release the compounds of the invention in a total amount of 10 mg to 300 mg per kg of body weight of the treated animal (10 mg / kg to 300 mg / kg), preferably 20 mg to 200 mg per kg (20 mg / kg to 200 mg / kg), most preferably 25 mg to 160 mg per kg (25 mg / kg to 160 mg / kg) during a period of 3 weeks. [Example]

[0539] Using the procedures described in the following preparative examples, with appropriate modification of the starting materials, additional compounds of Formula I were obtained. The compounds obtained in this manner are listed below in Table C along with their physical data.

[0540] Compounds can be analyzed by, for example, coupled high performance liquid chromatography / mass spectrometry (HPLC / MS), 1 They can be characterized by H-NMR and / or their melting points.

[0541] Analytical HPLC - Method 1: Agilent Eclipse Plus C18, 50 x 4.6 mm, ID 5 μm; Elution: A = 10 mM AMM formate (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, hold 1 min, 1 min - 10% B. Run time = 5.01 min.

[0542] 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 - 1.0 ml / min in 1.5 min, 60° C.; gradient: 5% B to 100% B in 1.5 min.

[0543] 1H-NMR: Signals are expressed as chemical shifts (ppm, δ [delta]) relative to tetramethylsilane CDCl3, respectively: 13 In the case of C-NMR, they are characterized by their multiplicity and their integral (for a given hydrogen atom). The following abbreviations are used to characterize the multiplicity of signals: m = multiplet, q = quartet, t = triplet, d = doublet, and s = singlet.

[0544] The abbreviations used are d for days, h for hours, min for minutes, RT / room temperature 20-25°C, Rt for retention time; DMSO for dimethyl sulfoxide, OAc for acetate, EtOAc for ethyl acetate, IPA for isopropyl alcohol, MeOH for methanol, EtOH for ethanol, THF for tetrahydrofuran, DMF for N,N-dimethylformamide, and t-BuOH for tert-butanol.

[0545] Preparation example: Example C-1: N-[1-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene] Synthesis of [carbamoyl]amino]-3-methyl-phenyl]-3-methyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide Step 1: Synthesis of 3-methyl-1H-pyrazol-4-amine To a stirred solution of 3-methyl-4-nitropyrazole (5 g) in a mixture of IPA (40 mL) and MeOH (40 mL) was added bispinacolatodiboron (30.0 g) and potassium tert-butoxide (5.3 g) at room temperature. The entire reaction mixture was heated at 110° C. for 3 hours. The progress of the reaction was monitored by GCMS analysis. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated under reduced pressure to give the desired product (3.8 g) as a brown solid. GC / MS: Rt: 4.07 min, m / z=97 (M).

[0546] Step 2: Synthesis of N-(3-methyl-1H-pyrazol-4-yl)-4-(trifluoromethoxy)benzamide To a stirred solution of 3-methyl-4-aminopyrazole (2.9 g) in dry THF (55 mL) was added triethylamine (14.14 mL) at 0° C., followed by the slow addition of 4-trifluoromethoxybenzoyl chloride (7.85 g). The reaction mixture was stirred at room temperature for 3 hours. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (200 mL) and then extracted with EtOAc (100 mL×2). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the desired product (8.0 g) as a brown solid. 1 H NMR(300MHz,DMSO-d6)δ 12.43(d,J=12.0Hz,1H),9.81(s,1H),8.15-7.99(m,2H),7.88(s,1H),7.61-7.40(m,2H),2.18(s,3H).

[0547] Step 3: Synthesis of N-[3-methyl-1-(3-methyl-4-nitro-phenyl)pyrazol-4-yl]-4-(trifluoromethoxy)benzamide: To a stirred solution of N-(3-methyl-1H-pyrazol-4-yl)-4-(trifluoromethoxy)benzamide (0.4 g) in dry DMF (10 mL) was added cesium carbonate (0.912 g) and 4-fluoro-2-methyl-1-nitrobenzene (0.326 g) at room temperature. The reaction mixture was heated at 110° C. for 24 hours. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (100 mL) and then extracted with EtOAc (50 mL×2). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography using EtOAc and heptane as eluents to give the desired product (0.45 g) as an off-white solid. HPLC / MS (Method 1): Rt: 2.388 min; m / z=419 (M-1). + ; 1H NMR(300MHz,DMSO-d6)δ 10.15(s,1H),8.89(s,1H),8.16(d,J=9.0Hz,1H),8.10(d,J=8.7Hz,2H),7.99(d,J=1. 9Hz,1H),7.89(dd,J=9.1,2.5Hz,1H),7.56(d,J=7.9Hz,2H),2.64(s,3H),2.35(s,3H).

[0548] Step 4: Synthesis of N-[1-(4-amino-3-methyl-phenyl)-3-methyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide: To a stirred solution of N-[3-methyl-1-(3-methyl-4-nitro-phenyl)pyrazol-4-yl]-4-(trifluoromethoxy)benzamide (0.4 g) in a mixture of EtOH:EtOAc (5 mL:5 mL) was added tin(II) chloride dihydrate (0.854 g) at room temperature. The reaction mixture was heated at 80° C. for 6 hours. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (50 mL), basified with solid sodium bicarbonate, and then extracted with EtOAc (25 mL×2). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by n-pentane washing (2 mL×2) to give the desired product (0.35 g) as a beige solid. HPLC / MS (Method 1): Rt: 2.091 min; m / z=391 (M+1). + . 1 H NMR(500MHz,DMSO-d6)δ 9.95(s,1H),8.36(s,1H),8.08(d,J=8.8Hz,2H),7.53(d,J=8.2Hz,2H),7.34(d,J=2.2Hz ,1H),7.29-7.23c(m,1H),6.66(d,J=8.5Hz,1H),4.93(s,2H),2.25(s,3H),2.12(s,3H).

[0549] Step 5: Synthesis of N-[1-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]-3-methyl-phenyl]-3-methyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide: To a stirred solution of N-[1-(4-amino-3-methyl-phenyl)-3-methyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide (0.15 g) in dry THF (5 mL) at 0°C, 4-nitrophenyl chloroformate (0.077 g) was added. The reaction mixture was stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC. The reaction mixture was again cooled to 0°C, and N,N-diisopropylethylamine (0.122 mL) was added, followed by 2-imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (0.116 g). To the reaction mixture, dry acetonitrile (5 mL) and potassium phosphate tribasic (0.149 g) were added. The reaction mixture was stirred at room temperature for 12 hours. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (20 mL x 2). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by column chromatography using EtOAc and heptane as eluents to give the desired product (0.12 g) as a beige solid. HPLC / MS (Method 1): Rt: 2.464 min; m / z=665 (M+1). + . 1 H NMR(500MHz,DMSO-d6)δ 10.03(s,1H),9.13(s,1H),8.60(s,1H),8.09(d,J=8.7Hz,2H),7.63(s,1H) ,7.54(m,3H),7.40(d,J=7.9Hz,1H),7.33(d,J=8.5Hz,1H),7.27(d,J=6.7H z,1H),7.07(s,1H),4.17(m,1H),4.06(m,2H),2.72-2.65(m,1H),2.32(s,3 H),2.29(s,3H),2.20(s,3H),1.21(d,J=6.9Hz,3H),1.10(d,J=6.8Hz,3H).

[0550] Example C-2: Synthesis of N-[1-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-3-methyl-pyrazol-4-yl]-N-methyl 4-(trifluoromethoxy)benzamide: Step 1: Synthesis of N-methyl-N-[3-methyl-1-(4-nitrophenyl)pyrazol-4-yl]-4-(trifluoromethoxy)benzamide: To a stirred solution of N-[3-methyl-1-(4-nitrophenyl)pyrazol-4-yl]-4-(trifluoromethoxy)benzamide (2 g) in DMF (50 mL) was added cesium carbonate (3.2 g) and methyl iodide (0.9 g). The reaction mixture was stirred at 50° C. until the starting material was consumed. Then, DMF was evaporated, and EtOAc was added to the residue. The precipitate was filtered off and purified via column chromatography to give the desired product (2 g). 1 H NMR(400MHz,chloroform-d)δ 8.33-8.25(m,2H),7.71(d,J=8.3Hz,3H),7.45(d,J=8.3Hz,2H),7.10(m,2H),3.41(s,3H),2.18(s,3H).

[0551] Step 2: Synthesis of N-[1-(4-aminophenyl)-3-methyl-pyrazol-4-yl]-N-methyl-4-(trifluoromethoxy)benzamide: N-methyl-[3-methyl-1-(4-nitrophenyl)pyrazol-4-yl]-4-(trifluoromethoxy)benzamide (2 g) was dissolved in a 1:1 mixture of EtOAc (16.5 mL) and EtOH (16.5 mL). To the reaction mixture was added tin(II) chloride dihydrate (4.7 g) at room temperature. The progress of the reaction was monitored by TLC, and once the starting material was consumed, the reaction mixture was diluted with saturated aqueous sodium bicarbonate. (The reaction was quenched by the addition of 220 mL of HCl. The reaction mixture was filtered through a pad of Celite, and the organic phase was extracted three times with EtOAc. The combined organic phases were dried over magnesium sulfate, and the residue was purified by flash chromatography to give the desired product (1.8 g). 1 H NMR(400MHz,chloroform-d)δ 7.52-7.33(m,3H),7.24(d,J=8.3Hz,2H),7.06(d,J=8.3Hz,2H),6.78-6.55(m,2H),3.65(m,2H),3.40(s,3H),2.08(s,3H).

[0552] Step 3: Synthesis of N-[1-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-3-methyl-pyrazol-4-yl]-N-methyl-4-(trifluoromethoxy)benzamide (C-2): To a stirred solution of N-[1-(4-aminophenyl)-3-methylpyrazol-4-yl]-N-methyl-4-(trifluoromethoxy)benzamide (0.4 g) in THF (12 mL) was added 4-nitrophenyl chloroformate (0.2 g) at 0 °C. After stirring at room temperature for 3 h, the starting material was consumed, as indicated by TLC. The solvent was evaporated, and the crude product was used directly in the next step. The residue was dissolved in acetonitrile (15 mL), and then 2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one (0.2 g), diisopropylamine (0.25 mL), and potassium phosphate (0.3 g) were added. The reaction mixture was stirred overnight at room temperature and then diluted with water (40 mL). The organic phase was extracted three times with EtOAc, washed with brine, and dried over magnesium sulfate. Purification by column chromatography gave the desired product (0.36 g). 1H NMR (400 MHz, chloroform-d) δ 7.58-7.50 (m, 3H), 7.45-7.27 (m, 7H), 7.06 (d, J = 8.0 Hz, 2H), 6.90 (s, 1H), 3.97 (s, 2H), 3.39 (s, 3H), 2.66 (m, 1H), 2.38 (s, 3H), 2.13 (s, 3H), 1.19 (m, 6H).

[0553] Example C-3: Synthesis of N-[5-chloro-1-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-3-methyl-pyrazol-4-yl]-N-methyl-4-(trifluoromethoxy)benzamide: Step 1: Synthesis of N-[5-chloro-1-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-3-methyl-pyrazol-4-yl]-N-methyl-4-(trifluoromethoxy)benzamide (C-3): Thiobiuret C-2 (160 mg) was dissolved in chloroform (5 mL), and methyl N-(N'-chloro-N-methoxycarbonyl-carbamimidoyl)carbamate (Palau'Chlor®) (0.076 g) was added at room temperature and stirred for 22 h. The solvent was partially evaporated, and the mixture was quenched with water (30 mL), and the aqueous phase was extracted three times with EtOAc. The combined organic phases were dried over magnesium sulfate. Purification by column chromatography gave the desired product (0.093 g). 1 H NMR(400MHz,chloroform-d)d 7.57(d,J=8.7Hz,2H),7.45-7.25(m,6H),7.08(d,J=8.3Hz,2H),6.93-6.88(s,1H),3.97(d, J=3.2Hz,2H),3.77(s,1H),3.36(s,3H),2.66(m,1H),2.38(s,3H),2.15(s,3H),1.19(m,6H).

[0554] Example C-4: Synthesis of N-[1-[3-chloro-4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-3,5-dimethyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide Step 1: Synthesis of 3,5-dimethyl-1H-pyrazol-4-amine: To a stirred solution of 3,5-dimethyl-4-nitro-1H-pyrazole (10 g) in 250 mL of EtOH:HO (4:1) mixture, Fe (11.872 g) and ammonium chloride (37.9 g) were added at room temperature. The reaction mixture was heated at 80 °C for 5 h. The progress of the reaction was monitored by TLC. The reaction mixture was cooled to room temperature and filtered through a Celite pad, which was washed with EtOAc (100 mL). The filtrate was concentrated to two-thirds of its volume under reduced pressure, diluted again with EtOAc (100 mL), and water (50 mL) was added. The layers were separated, and the organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by n-pentane washing (25 mL × 2) to give the desired product (4 g) as a beige solid.

[0555] Step 2: Synthesis of N-(3,5-dimethyl-1H-pyrazol-4-yl)-4(trifluoromethoxy)benzamide: To a stirred solution of 3-methyl-4-aminopyrazole (4 g) in dichloromethane (60 mL) was added 4-trifluoromethoxybenzoic acid (7.4 g) at 10° C., followed by diisopropylethylamine (25 mL). The reaction mixture was cooled to 0° C., and 1-propanephosphonic anhydride solution (160.5 mL, 50% solution in EtOAc) was added dropwise to the reaction mixture over 4 hours. The progress of the reaction was monitored by HPLC. After completion of the reaction, the reaction mixture was added dropwise to water (750 mL) and stirred for 60 minutes. A white precipitate formed, which was filtered and dried under reduced pressure to give the desired product (9.8 g) as a white solid compound. HPLC / MS (Method 1): Rt: 1.75 min; m / z=300 (M+1). + . 1H NMR(300MHz,DMSO-d6)δ 9.59(s,1H),8.10(d,J=8.3Hz,2H),7.50(d,J=8.3Hz,2H),2.06(s,6H).

[0556] Step 3: Synthesis of N-[3,5-dimethyl-1-(4-nitrophenyl)pyrazol-4-yl]-4-(trifluoromethoxy)benzamide: To a stirred solution of N-(3,5-dimethyl-1H-pyrazol-4-yl)-4-(trifluoromethoxy)benzamide (1 g) in dry DMF (10 mL) was added cesium carbonate (1.415 g) and 1-fluoro-4-nitrobenzene (0.707 g) at room temperature. The reaction mixture was heated at 70° C. for 24 hours. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (100 mL) and the precipitate was collected by filtration. The solid was dried under vacuum and washed with n-pentane to give the desired product (1.3 g) as a yellow solid. HPLC / MS (Method 1): Rt: 1.871 min; m / z=419 (M-1). + ; 1 H NMR(300MHz,DMSO-d6)δ 9.94(s,1H),8.37(d,J=9.1Hz,2H),8.14(d,J=8.7Hz,2H),7.90(d,J=9.1Hz,2H),7.55(d,J=8.3Hz,2H),2.35(s,3H),2.16(s,3H).

[0557] Step 4: Synthesis of N-[1-(4-aminophenyl)-3,5-dimethyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide: To a solution (300 mL) of N-[3,5-dimethyl-1-(4-nitrophenyl)pyrazol-4-yl]-4-(trifluoromethoxy)benzamide (20 g) in 127 mL of MeOH was added palladium on carbon (1.45 g). The reaction mixture was subjected to hydrogenation at 40 psi for 18 hours. The progress of the reaction was monitored by TLC. The reaction mixture was filtered through a Celite pad, and the Celite pad was washed with MeOH (100 mL). The filtrate was concentrated under reduced pressure to give the crude product, which was purified by column chromatography using EtOAc and heptane as eluents to give the desired product (7 g) as a beige solid. HPLC / MS (Method 1): Rt: 1.697 min; m / z = 391 (M+1). + ; 1 H NMR(500MHz,DMSO-d6)δ 9.72(s,1H),8.11(d,J=8.8Hz,2H),7.53(d,J=8.1Hz,2H),7.09(d,J=8.6Hz,2H),6.65(d,J=8.7Hz,2H),5.31(s,2H),2.09(s,3H),2.08(s,3H).

[0558] Step 5: Synthesis of N-[1-(4-amino-3-chloro-phenyl)-3,5-dimethyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide: To a stirred solution of N-[1-(4-aminophenyl)-3,5-dimethyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide (0.3 g) in acetonitrile (5 mL) was added N-chlorosuccinimide (0.123 g) at room temperature. The reaction mixture was heated at 90° C. for 2 hours. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (20 mL×2). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by column chromatography using EtOAc and heptane as eluents to give the desired product (0.1 g) as a beige solid. HPLC / MS (Method 1): Rt: 1.995 min; m / z=426 (M+1). + . 1H NMR(500MHz,DMSO-d6)δ 9.75(s,1H),8.12(d,J=8.4Hz,2H),7.53(d,J=8.3Hz,2H),7.32(s,1H),7.16(d ,J=10.1Hz,1H),6.88(d,J=8.6Hz,1H),5.59(s,2H),2.13(s,3H),2.09(s,3H).

[0559] Step 6: Synthesis of N-[1-[3-chloro-4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-3,5-dimethyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide: To a stirred solution of N-[1-(4-amino-3-chloro-phenyl)-3,5-dimethyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide (0.9 g) in dry THF (15 mL) was added 4-nitrophenyl chloroformate (0.512 g) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC. The reaction mixture was again cooled to 0° C., and N,N-diisopropylethylamine (0.531 mL) was added, followed by 2-imino-3-(2-isopropyl-5-methyl-phenyl)thiazolidin-4-one (0.505 g). To the reaction mixture was added dry acetonitrile (20 mL) and potassium phosphate tribasic (0.648 g). The reaction mixture was stirred at room temperature for 12 hours. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (50 mL × 2). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by column chromatography using EtOAc and heptane as eluents to give the desired product (1 g) as a beige solid. HPLC / MS (Method 1): Rt: 1.291 min; m / z=700 (M+1). + . 1H NMR(500MHz,DMSO-d6)δ 9.83(s,1H),9.17(s,1H),8.12(d,J=8.2Hz,2H),7.67(m,2H),7.52(m,3H),7.39(m,1H),7.33-7.22(m,1H),7.07(s,1H) ,4.28-4.04(m,2H),2.73-2.62(m,1H),2.32(s,3H),2.24(s,3H),2.12(s,3H),1.27-1.14(m,3H),1.10(d,J=6.1Hz,3H).

[0560] Example C-5: Synthesis of N-[5-cyclopropyl-1-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]carbamoyl]amino]phenyl]-3-methyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide: Step 1: Synthesis of 1-cyclopropylbutane-1,3-dione To a stirred solution of sodium methoxide (3.8 g) in methyl tert-butyl ether (MTBE) (30 mL) was added cyclopropyl methyl ketone (3 g). The reaction mass was heated to 30° C., and then EtOAc (6.3 g) was added over 45 minutes at 30° C. The reaction mixture was stirred at 30° C. for 3 hours. The progress of the reaction was monitored by TLC and GCMS. After the reaction was complete, the reaction mixture was added dropwise to water (30 mL). The layers were separated, and the aqueous layer was acidified with 2.5 M HCl (10 mL) followed by extraction with MTBE (2×10 mL). The organic layer was dried over sodium sulfate and evaporated under reduced pressure to give the crude product (4 g) as a brown liquid, which was purified by column chromatography using EtOAc and heptane as eluents to give the desired product (2 g) as a colorless oily liquid. GCMS (low temperature volatiles): Rt: 5.41 min; m / z=126. 1H NMR (500 MHz, DMSO): mixture of keto and enol tautomers, δ 12.01 (s, 1H), 5.86 (s, 1H), 3.82 (s, 1H), 2.22-2.18 (m, 2H), 2.06-2.02 (m, 4H), 1.99-1.94 (m, 2H), 1.86-1.80 (m, 1H), 1.03-0.96 (m, 4H).

[0561] Step 2: Synthesis of 1-(4-bromophenyl)-5-cyclopropyl-3-methyl-pyrazole To a stirred solution of 1-cyclopropylbutane-1,3-dione (2 g) in acetic acid (20 mL) was added dropwise a solution of 4-bromophenylhydrazine hydrochloride (3.5 g) in water (20 mL) while maintaining the temperature below 30° C. The reaction mass was stirred at 25° C. for 6 hours. The progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was added to water (50 mL), extracted with MTBE (2×10 mL), the organic layer was washed with saturated sodium bicarbonate solution (2×30 mL), the organic layer was dried over sodium sulfate and evaporated under reduced pressure to give the desired product (4 g) as an off-white solid. HPLC / MS (Method 1): Rt: 1.93 min; m / z=277 (M+1). + 279(M+3) + Bromo pattern. 1 H NMR(500MHz,DMSO)δ 7.67(d,J=8.8,2.1Hz,2H),7.61-7.56(d,2H),5.92(s,J=1.9Hz,1H),2.16(s,J=2.1Hz ,3H),1.81(m,J=8.3,5.4,2.5Hz,1H),0.96-0.90(dd,2H),0.68(dd,J=5.0,2.4Hz,2H).

[0562] Step 3: Synthesis of 1-(4-bromophenyl)-5-cyclopropyl-3-methyl-4-nitro-pyrazole To a stirred solution of 1-(4-bromophenyl)-5-cyclopropyl-3-methyl-pyrazole (1 g) in dichloroethane (10 mL) was added sulfuric acid (1.76 mL) dropwise while maintaining the temperature below 20°C. The reaction mass was cooled to 10°C, and fuming nitric acid (0.16 mL) was added to the reaction mass while maintaining the temperature below 10°C. The reaction mass was stirred at 10°C for 1 hour. The progress of the reaction was monitored by TLC and LCMS. After the reaction was completed, it was added to water (50 mL), the aqueous layer was extracted with MTBE (2 × 10 mL), the organic layer was washed with saturated sodium bicarbonate solution (2 × 30 mL), dried over sodium sulfate, and evaporated under reduced pressure to give the crude product (4 g) as a light brown solid. The crude product was purified by column chromatography using EtOAc and heptane as eluents to give the desired product (0.55 g) as an off-white solid. HPLC / MS (method 1): Rt: 2.15 min; m / z=322.3(M+1) + 324(M+3) + Bromo pattern. 1 H NMR(300MHz,DMSO)δ 7.78(d,J=8.7Hz,2H),7.66-7.58(m,2H),2.26(tt,J=8.5,5.7Hz,1H),0.94(dd,J=8.4,2.2Hz,2H),0.37(dd,J=5.7,1.9Hz,2H).

[0563] Step 4: Synthesis of 1-(4-bromophenyl)-5-cyclopropyl-3-methyl-pyrazol-4-amine To a stirred solution of 1-...

Claims

1. Equation I 【Chemistry 1】 (In the formula, Q is -C(=O)-N(R ５ ) - or -N(R ５ ) - C (= O) - and; R ５ is H, C １ to C ６ -alkyl, C ３ to C ６ -cycloalkyl, C １ to C ６ -alkyl-C １ to C ３ -alkoxy or C １ to C ６ -alkyl-C ６ to C ６ -cycloalkyl, phenyl, 5- or 6-membered heteroaryl, -CH ２ -phenyl, -CH ２ -5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or halogen, where the alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted with halogen; R １ H, C １ ~C ６ - Alkyl, C ３ ~C ６ - Cycloalkyl, halogen, or NR ６ R ７ Here, the alkyl and cycloalkyl portions are either unsubstituted or substituted with halogens or CN; R ２ H, C １ ~C ６ - Alkyl, C ３ ~C ６ - A cycloalkyl or halogen, where the alkyl and cycloalkyl portions are either unsubstituted or substituted with a halogen or CN; 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 CR Ｂ４ And; R Ｂ１ , R Ｂ２ , R Ｂ３ , and R Ｂ４ These are H, halogen, CN, and C, which are independent of each other. １ ~C ６ - Alkyl, C ３ ~C ６ -Cycloalkyl, or C １ ~C ６ - It is an alkoxy, where the alkyl, alkoxy, and cycloalkyl moieties are either unsubstituted or substituted with halogens; D is a partial DA or DB, 【Chemistry 2】 R ３ H, C １ ~C ６ - Alkyl or C ３ ~C ６ - It is a cycloalkyl compound, where the alkyl and cycloalkyl portions are either unsubstituted or substituted with halogens or CN; R ４ H, C １ ~C ６ - Alkyl or C ３ ~C ６ - It is a cycloalkyl compound, where the alkyl and cycloalkyl portions are unsubstituted or halogen, -O-(C=O)-C １ ~C ６ -Alkyl, -O-(C=O)-C １ ~C ６ - Substituted with alkoxy or CN; B is a five- or six-membered carbon ring group, where one or two CH groups are located within the carbon ring group. ２ The portion may be replaced by a carbonyl group, O, or S, and the carbocyclic group is unsubstituted or R ｈ It has been replaced with; Ar １ These are phenyl or a 5- or 6-membered heteroaryl, which are unsubstituted or R Ａｒ１ It has been replaced with, here, 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, where the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C ３ ~C ６ -heterocyclyl, and cycloalkoxy moieties are unsubstituted or are substituted by R ｆ ; C(=O)-OR ａ , NR 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 , SO. ２ NR ｂ R ｃ , or S(=O) ｍ R ｅ and is substituted by; R ６ and R ７ They are either the same or different, H, C １ ~C ６ - Alkyl, C ３ ~C ６ -Cycloalkyl, phenyl, -CH ２ - Phenyl, 5-membered or 6-membered heteroaryl, - CH ２ - A 5-membered or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl, or 2-(methylamino)-2-oxo-ethyl, where the alkyl, cycloalkyl, phenyl, and heteroaryl moieties are unsubstituted or halogen, CN, C １ ~C ６ - Alkyl or C １ ~C ６ - Substituted with alkoxy; Ar ２ is phenyl or a 5- or 6-membered heteroaryl, which is unsubstituted or R Ａｒ２ It has been replaced with, here, R Ａｒ２ Halogen, CN, -SCN, -SF ５ , C １ ~C ６ - Alkyl, C １ ~C ６ - Alkoxy, C ２ ~C ６ - Alkenil, C ２ ~C ６ - Alkinyl, 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, where alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or halogen, C(=O)-OR ａ , NR ｂ R ｃ , C １ ~C ６ -Alkylene-CN,C(=O)-NR ｂ R ｃ It has been replaced with; R ａ , R ｂ and R ｃ They are either the same or different, H, C １ ~C ６ - Alkyl, C ２ ~C ６ - Alkenil, C ３ ~C ６ - Cycloalkyl, C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -alkyl, -C(=O)-C １ ~C ６ -It is alkyl, where the alkyl, alkenyl, and cycloalkyl moieties are either unsubstituted or substituted with halogens. R ｄ H, C １ ~C ６ - Alkyl; R ｅ C １ ~C ６ - Alkyl, C ３ ~C ６ - Cycloalkyl, C ３ ~C ６ -Cycloalkyl-C １ ~C ４ - Alkyl, where the alkyl or cycloalkyl portion is either unsubstituted or substituted with a halogen or CN; R ｆ These are halogens, OH, CN, NO ２ SCN, -SF ５ , C １ ~C ６ Alkyl, C １ ~C ６ - Alkoxy, C ２ ~C ６ - Alkenil, C ２ ~C ６ - Alkinyl, 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, where the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are either unsubstituted or substituted with halogens; R ｈ is halogen, C １ ~C ６ - Alkyl or C １ ~C ６ - It is an alkoxy; m is 0, 1, or 2. Compounds of the same; and their N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts.

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

3. D is either unsubstituted or has one or two substituents R ｈ A group selected from the D5-D7 portion substituted by R ｈ The compound of formula I according to claim 1, as defined in claim 1. 【Transformation 3】

4. A compound of formula I according to claim 1, selected from the compounds of formula I.1 to I.

4. 【Chemistry 4】

5. R ５ H, C １ ~C ６ - Alkyl or C １ ~C ６ -Alkyl-C ３ ~C ６ -It is a cycloalkyl; R １ is halogen, C １ ~C ６ - Alkyl or C ３ ~C ６ -It is a cycloalkyl; R ２ is H or C １ ~C ６ It is alkyl. The compound of formula I as described in claim 1.

6. B １ CR Ｂ１ B ２ CR Ｂ２ B ３ CR Ｂ３ The compound of formula I as described in claim 1.

7. B １ is N, B ２ CR Ｂ２ B ３ CR Ｂ３ The compound of formula I as described in claim 1.

8. R Ｂ１ , R Ｂ２ , R Ｂ３ and R Ｂ４ These are H, halogen, CN, and C, which are independent of each other. １ ~C ６ - Alkyl, C ３ ~C ６ -Cycloalkyl, or C １ ~C ６ - The compound of formula I according to claim 1, wherein the alkyl, alkoxy, and cycloalkyl moieties are either unsubstituted or substituted with halogens.

9. Ar １ is either unsubstituted or R Ａｒ１ It is substituted with phenyl, pyrimidinyl, pyridadinyl, thiophenyl, thiazolyl, or pyridyl; R Ａｒ１ 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 - Alkenil, C ２ ~C ６ - Alkynyl, where alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C ３ ~C ６ - The heterocyclyl and cycloalkoxy moieties are either unsubstituted or R ｆ ; C (= O) - OR ａ , NR 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 SO ２ NR ｂ R ｃ Or S (=O) ｍ R ｅ It has been replaced with; R ａ , R ｂ and R ｃ They are either the same or different, H, C １ ~C ６ - Alkyl (unsubstituted or substituted with halogen); R ｄ is H or C １ ~C ６ It is alkyl; R ｅ C １ ~C ６ - Alkyl or C １ ~C ６ - It is a haloalkyl; R ｆ These are halogens, OH, CN, and C １ ~C ６ - Alkyl, C １ ~C ６ - Alkoxy, C ２ ~C ６ - Alkenil, C ２ ~C ６ - Alkinyl, C ３ ~C ６ - Cycloalkyl, C ３ ~C ６ - It is a cycloalkoxy (unsubstituted or substituted with a halogen); m is 0, 1, or 2. The compound of formula I as described in claim 1.

10. A composition comprising one compound of formula I as described in claim 1, its N-oxide or an agriculturally acceptable salt, and further active substances.

11. A method for eradicating or controlling invertebrate pests, comprising contacting the pest or its food source, habitat or breeding ground with an effective amount of at least one compound described in any one of claims 1 to 9 or the composition described in claim 10.

12. A method for protecting a growing plant from attack or parasitism by an invertebrate pest, comprising contacting the plant, or the soil or water in which the plant is growing, with an effective amount of at least one compound according to any one of claims 1 to 9 or the composition according to claim 10.

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

14. Use of a compound of formula I according to any one of claims 1 to 9, and an agronomically acceptable salt thereof, or the composition according to claim 10, for protecting growing plants from attack or parasitism by invertebrate pests.

15. A method for treating or protecting an animal from parasitism or infection by an invertebrate pest, comprising contacting the animal with an effective amount of at least one compound of formula I as described in any one of claims 1 to 9, its stereoisomer and / or at least one veterinarily acceptable salt thereof.

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