Pyrazolopesticidal compounds

Abstract

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

Description

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

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

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

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

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

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

[0007]

[0008] in

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

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

[0011] 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 by halogen or CN;

[0012] R 2 is H, C1-C6-alkyl, C3-C6-cycloalkyl or halogen, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0013] B 1 Is N or CR B1 ;

[0014] B 2 Is N or CR B2 ;

[0015] B 3 Is N or CR B3 ;

[0016] B 4 It's CR B4 ;

[0017] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0018] D is part DA or DB,

[0019]

[0020] R 3 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0021] R 4 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkyl, -O-(C=O)-C1-C6-alkoxy or CN;

[0022] B is a 5- or 6-membered carbocyclic group, wherein one or two CH2 moieties of the carbocyclic group may be replaced by a carbonyl, O or S, wherein the carbocyclic group is unsubstituted or replaced by R h replace;

[0023] Ar 1 is phenyl or a 5- or 6-membered heteroaryl group, which is unsubstituted or replaced by R Ar1 Replace, where

[0024] R Ar1 is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f replace;

[0025] C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、S(=O) m R e 、-N=S(=O)-(C1-C6-alkyl)2、SO2NR b R c or S(=O) m R e ;

[0026] R 6 and R 7 are identical or different H, C1-C6-alkyl, C3-C6-cycloalkyl, phenyl, -CH2-phenyl, 5- or 6-membered heteroaryl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl, wherein these alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN, C1-C6-alkyl or C1-C6-alkoxy;

[0027] Ar 2 is phenyl or a 5- or 6-membered heteroaryl group, which is unsubstituted or replaced by R Ar2 Replace, where

[0028] 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-cycloalkyloxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyloxy-C1-C4-alkyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted by halogen;

[0029] C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c ;

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

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

[0032] R e is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, wherein these alkyl, cycloalkyl parts are unsubstituted or substituted by halogen or CN;

[0033] R f is halogen, OH, CN, SCN, -SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyloxy-C1-C4-alkyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted by halogen;

[0034] R h is halogen, C1-C6-alkyl or C1-C6-alkoxy;

[0035] m is 0, 1, or 2,

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

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

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

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

[0040] General procedures:

[0041] The compounds of formula (I) can be prepared by organic chemistry methods (e.g., by the methods described in Schemes 1 to 19 below in the description of the synthesis of the Examples). Unless otherwise indicated, in Schemes 1 to 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 As defined above for formula (I).

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

[0043] Option 1:

[0044]

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

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

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

[0048] Option 2:

[0049]

[0050] According to the method depicted in Scheme 2, an amine of formula (Ia-1) can be treated with an activating agent (such as 4-nitrophenyl chloroformate) in the presence of a polar aprotic solvent (preferably tetrahydrofuran) to generate an activated amine (Ia-1'), which in turn reacts 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). The compound of formula (E1) can be prepared by analogy with the method described in WO 2021 / 011722.

[0051] Option 3:

[0052]

[0053] As depicted in Scheme 3, compounds of formula (E1) can be treated with an activating agent (such as 4-nitrophenyl chloroformate) in the presence of a polar aprotic solvent (preferably tetrahydrofuran) and an inorganic base (such as cesium carbonate or potassium carbonate) to generate an activated carbamate intermediate (E1-1), which in turn reacts with an amine of formula (Ia-1) in the presence of an inorganic base (such as cesium carbonate or potassium carbonate) to form a compound of formula (Ia).

[0054] The compounds of formula (I) (where R 4 When it is H, it is a compound of formula (Ia')).

[0055] Option 4:

[0056]

[0057] As depicted in Scheme 4, compounds of formula (Ia') can be prepared by treating an arylthiourea of ​​formula (E1') with an isocyanate of formula (Ia-2) in an aprotic solvent in the presence of an inorganic base such as cesium carbonate or sodium hydride. Compounds of formula (E1') can be prepared by analogy with the method described in WO 2021 / 011722.

[0058] Compounds of formula (E1-I), (E1-II), (E1-III) and (E1-IV) can be prepared by analogy with the method described in J. of Med. Chem. 2010, 53(10), 4198-4211 or the method described in Scheme 5.

[0059] Option 5:

[0060]

[0061] In the above reactions, the compound of formula (E1-Ia) can be converted into various cyclized analogs of formula (E1-I), (E1-II), (E1-III) and (E1-IV). The compounds of formula (E1-I) and (E1-II) can be prepared by treating the compound of formula (E1-Ia) with unsubstituted or mono- or disubstituted 2-chloroacetyl chloride and 3-chloropropionyl chloride in two steps, as described in J. of Med. Chem. 2010, 53(10), 4198-4211. The compounds of formula (E1-IIIa) and (E1-IVa) can be prepared by treating the compound of formula (E1-Ia) with unsubstituted or mono- or disubstituted 2-chloroacetaldehyde and 3-chloro-propionaldehyde in two steps, as mentioned in J. 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-IVa) with potassium thiocyanate in an aprotic solvent such as acetone in the presence of an inorganic base such as cesium carbonate.

[0062] Compounds of formula (Ia-I), (Ia-II), (Ia-III) and (Ia-IV) can be prepared from compounds of formula (Ia′) by analogy with the methods described in WO 2021 / 011722 or the methods described in Scheme 6.

[0063] Option 6:

[0064]

[0065] In the above reaction, the compound of formula (Ia') can be converted into various cyclized analogs of formula (Ia-I), (Ia-II), (Ia-III) and (Ia-IV). Cyclization can be carried out by treating the compound of formula (Ia') with an α-haloester (such as methyl bromoacetate or methyl bromopropionate) to form an unsubstituted or R-substituted compound. h Mono- or di-substituted compounds of formula (Ia-I) and (Ia-II) can be prepared by treating the compound of formula (Ia') with an ortho-dihalide to obtain unsubstituted or R-substituted compounds. h Mono- or disubstituted compounds of formula (Ia-III) and (Ia-IV). For steps XVIII and XIX, sodium acetate is preferably used in a protic solvent (such as ethanol) at a temperature in the range of about 20°C to about 70°C. For steps XX and XXI, an inorganic base (such as potassium carbonate) is preferably used in a solvent (such as acetonitrile or 2-butanone) at a temperature between about 0°C and about 80°C. All of the above reactions can be carried out by analogy with the method described in WO 2021 / 011722.

[0066] Compounds of formula (Ia-1) can be prepared by analogy with the methods described in Scheme 7.

[0067] Option 7:

[0068]

[0069] As depicted in Scheme 7, compounds of formula (Ia-1) can be prepared using different synthetic routes. Step XXII can be carried out starting from arylboronic acid precursor (1) via a Chan-Lam coupling reaction as described in Chem. A Eur. J., 2017, 23(14), 3285-3290.

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

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

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

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

[0074] Option 8:

[0075]

[0076]

[0077] 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 starting from an arylboronic acid precursor (3) via a Chan-Lam coupling reaction, as described in Chem. A Eur. J., 2017, 23(14), 3285-3290.

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

[0079] Option 9:

[0080]

[0081] Step XXIX can be carried out starting from an arylboronic acid precursor (4) via a Chan-Lam coupling reaction as described in Chem.AEur.J. [European Journal of Chemistry], 2017, 23(14), 3285-3290. Hal as a bromide is preferred.

[0082] Compounds of formula (IVa-1) (where Q is -C(=O)-N(R 5 )-,R 1 is C1-C6-alkyl or C3-C6-cycloalkyl and R 5 When it is H, it is a compound of formula (IVa-1-1).

[0083] Option 10:

[0084]

[0085] As mentioned 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 (ArNHNH2,6), as described in WO 2016 / 044666. Compounds of formula (IVa-1-1a) can then be nitrated using a mixture of nitric acid and sulfuric acid in an aprotic solvent such as dichloroethane to produce compounds of formula (IVa-1-1b). Compounds of formula (IVa-1-1b) can be reduced to compounds of formula (IVa-1-1c) using a reducing agent such as SnCl2 in an acidic medium or Fe and NH4Cl in a mixture of ethanol and water, as shown in Step XXXII. Compounds of formula (IVa-1-1) can then be formed by amide coupling reaction of compounds of formula (IVa-1-1c) with benzoic acid derivatives using a suitable coupling reagent (such as HATU or T3P) and a base (such as DIPEA), as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March. Compounds of formula (IVa-1-1) can also be synthesized by treating compounds of formula (IVa-1-1c) with commercially available benzoyl chloride in the presence of a base, as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March. Compounds of formula (IVa-1-1) can also be synthesized by in situ generation of benzoyl chloride from the corresponding benzoic acid with POCl3 or SOCl2, followed by treatment with a compound of formula (IVa-1-1c) in the presence of a base, as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0086] Compounds of formula (IVa-1) (where Q is -N(R)) can be prepared by analogy with the method described in Scheme 11. 5 )-C(=O)-,R 1 is C1-C6-alkyl or C3-C6-cycloalkyl and R 5 When it is H, it is a compound of formula (IVa-1-2).

[0087] Option 11:

[0088]

[0089] Compounds of formula (IVa-1-2b) can be prepared in two steps starting from commercially available β-ketoester derivatives (7) via intermediates of formula (IVa-1-2a), as described in Synthesis, 2019, 51(6), 1473-1481. Step XXXV involves a 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, NaOH) as mentioned in WO 2011 / 050245. Step XXXVII involves an amide coupling reaction with an aniline derivative using a suitable coupling reagent (such as HATU or T3P) and a base (such as DIPEA), similar to that described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0090] Compounds of formula (IVa-1) (where Q is -C(=O)-N(R 5 )-,R 1 It is NR 6 R 7 And R 5 When it is H, it is a compound of formula (IVa-1-3).

[0091] Option 12:

[0092]

[0093] Compounds of formula (IVa-1-3a) can be prepared from commercially available β-ketoester derivatives (7′) by reacting them with substituted aryl hydrazines (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 the compound 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). Compounds of formula (IVa-1-3c) (wherein R 7 or R 6(is C1-C6-alkyl or C3-C6-cycloalkyl or -CH2-phenyl or -CH2-5 or 6-membered heteroaryl or 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl) can be prepared by reaction 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 a compound of formula (IVa-1-3d). The compound of formula (IVa-1-3d) (wherein R is ...c) can be prepared by metal-catalyzed reaction with the corresponding aniline 7 or R 6 is phenyl or 5- or 6-membered heteroaryl), as described in US20080036373. Compounds of formula (IVa-1-3d) (wherein R 7 or R 6 is H), 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 an acidic medium or Fe and NH4Cl in a mixture of ethanol and water), as shown in step XLII. Finally, compounds of formula (IVa-1-3) can be prepared by amide coupling reactions of compounds of formula (IVa-1-3e) with benzoic acid derivatives using a suitable coupling reagent (such as HATU or T3P) and a base (such as DIPEA), as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March. Compounds of formula (IVa-1-3) can also be synthesized by treating compounds of formula (IVa-1-3e) with commercially available benzoyl chloride in the presence of a base, as described in March's Advanced Organic Chemistry, 6th edition, by Michael B. Smith and Jerry March. Compounds of formula (IVa-1-3) can also be synthesized by in situ generation of benzoyl chloride from the corresponding benzoic acid with POCl or SOCl, followed by treatment with a compound of formula (IVa-1-3e) in the presence of a base, as described in March's Advanced Organic Chemistry, 6th edition, by Michael B. Smith and Jerry March.

[0094] Compounds of formula (IVa-1) (where Q is -N(R)) can be prepared by analogy with the method described in Scheme 13. 5 )-C(=O)-,R 1 It is NR 6 R 7 And R 5 When it is H, it is a compound of formula (IVa-1-4).

[0095] Option 13:

[0096]

[0097] Compounds of formula (IVa-1-4a) can be prepared from compounds of formula (IVa-1-3a) similar to the method described 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 a compound of formula (IVa-1-4b), which can be aminated to give a compound of formula (IVa-1-4c) as described under Scheme 12. Finally, an amide coupling reaction is performed by reacting the compound of formula (IVa-1-4c) with an aniline derivative using a suitable coupling reagent such as HATU or T3P and a base such as DIPEA to give a compound of formula (IVa-1-4), similar to that described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0098] Compounds of formula (IIa) (where Q is -C(=O)-N(R 5 )-,R 5 When it is H, it is a compound of formula (IIa-1-1).

[0099] Option 14:

[0100]

[0101] The compound of formula (IIa-1-1) can be prepared from the compound of formula (IIa-1-1a) in two steps as shown in Scheme 14. Step XLVIII involves the reduction of the nitro compound of formula (IIa-1-1a) using a reducing agent (such as SnCl2 in an acidic medium or Fe and NH4Cl in a mixture of ethanol and water), and step XLIX involves an analogous amide coupling reaction with a benzoic acid derivative using a suitable coupling reagent (such as HATU or T3P) and a base (such as DIPEA) as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0102] Compounds of formula (IIa) (where Q is -N(R 5 )-C(=O)-,R 5 When it is H, it is a compound of formula (IIa-1-2).

[0103] Option 15:

[0104]

[0105] 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 the hydrolysis of the ester using a suitable base (such as LiOH, NaOH), as mentioned in WO 2011 / 050245. Step L1 involves an amide coupling reaction with an aniline derivative using a suitable coupling reagent (such as HATU or T3P) and a base (such as DIPEA), similar to that described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0106] Compounds of formula (Ia-1) (where Q is -C(=O)-N(R 5 )-,R 5 When it is C1-C6-alkyl or C3-C6-cycloalkyl or -CH2-phenyl or -CH2-5 or 6-membered heteroaryl or 1,3-dioxolan-2-ylmethyl or phenyl or 5 or 6-membered heteroaryl, it is a compound of formula (Ia-1-1)).

[0107] Option 16:

[0108]

[0109] The compound of formula (Ia-1-1a) (wherein R 5 is C1-C6-alkyl or C3-C6-cycloalkyl or -CH2-phenyl or -CH2-5 or 6-membered heteroaryl or 1,3-dioxolan-2-ylmethyl) to prepare compounds of formula (Ia-1-1) analogously to what is described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March. Compounds of formula (Ia-1-1) (wherein R 5 is phenyl or a 5- or 6-membered heteroaryl), as described in Chinese J. of Chem. 2012, 30(10), 2356-2362. Alternatively, the compound of formula (Ia-1-1) can be prepared from the compound of formula (IIIa-1-1a) in two steps. Step LIII can be carried out similarly to step LII. Step LIV involves reduction using a reducing agent such as SnCl2 in an acidic medium or Fe and NH4Cl in a mixture of ethanol.

[0110] Compounds of formula (Ia-1) (where Q is -N(R)) can be prepared by analogy with the method described in Scheme 17. 5 )-C(=O)-,R 5 When it is C1-C6-alkyl or C3-C6-cycloalkyl or -CH2-phenyl or -CH2-5 or 6-membered heteroaryl or 1,3-dioxolan-2-ylmethyl or phenyl or 5 or 6-membered heteroaryl, it is a compound of formula (Ia-1-2)).

[0111] Option 17:

[0112]

[0113] Compounds of formula (Ia-1-2) can be prepared from compounds of formula (Ia-1-2a) or compounds of formula (IIIa-1-2a) using the reaction conditions discussed under Scheme 16.

[0114] Compounds of formula (Ia-1) (where R 1 is C1-C6-alkyl or C3-C6-cycloalkyl and B 2 or B 3 It's CR B2or CR B3 , where R B2 or R B3 When it is Hal, it is a compound of formula (Ia-1-3).

[0115] Plan 18:

[0116]

[0117] Compounds of formula (Ia-1-3) can be prepared by treating compounds of formula (Ia-1-3a) with an electrophilic halogenating agent such as NCS in a polar aprotic solvent such as ACN, similarly as described in March's Advanced Organic Chemistry, 6th edition, Michael B. Smith and Jerry March.

[0118] Compounds of formula (Ia-I) (where R 1 When it is Hal, it is a compound of formula (Ia-I-1).

[0119] Plan 19:

[0120]

[0121] 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.

[0122] Individual compounds of Formula I may also be prepared by derivatization of other compounds of Formula I or intermediates thereof.

[0123] If a mixture of isomers is obtained during synthesis, separation is generally not necessary, since the individual isomers may in some cases be converted into one another during post-processing for use or during application (e.g. under the action of light, acids or bases). Such conversions may also occur after use, for example in the case of plant treatment, in the treated plant or in the harmful fungi to be controlled.

[0124] The skilled person will readily appreciate that the preferences for the substituents given herein in conjunction with compound I, and in particular also the preferences given in the following table for the corresponding substituents, apply correspondingly to the intermediates. The substituents therefore in each case, independently of one another or more preferably in combination, have the meanings as defined herein.

[0125] Unless otherwise indicated, the term "compound according to the invention" or "compound of the present invention" or "compound of formula (I)" refers to

[0126] Compounds of formula I.

[0127] The term "compound according to the invention" or "compound of formula I" includes compounds as defined herein and stereoisomers, salts, tautomers or N-oxides thereof. The term "compound according to the invention" should be understood as equivalent to the term "compound according to the invention" and therefore also includes stereoisomers, salts, tautomers or N-oxides thereof.

[0128] The term "composition according to the invention" or "composition of the invention" encompasses a composition as defined above comprising at least one compound of formula I according to the invention. The composition of the invention is preferably an agricultural or veterinary composition.

[0129] Depending on the substitution pattern, the compound according to the present invention can have one or more chiral centers, in which case they exist as mixtures of enantiomers or diastereomers. The present invention provides single pure enantiomers or pure diastereomers and mixtures thereof of the compound according to the present invention, as well as the use according to the present invention of the pure enantiomers or pure diastereomers or mixtures thereof of the compound according to the present invention. Suitable compounds according to the present invention also include all possible geometric stereoisomers (cis / trans isomers) and mixtures thereof. Cis / trans isomers can exist with respect to olefins, carbon-nitrogen double bonds or amide groups. The term "stereoisomer" encompasses optical isomers, such as enantiomers or diastereomers (the latter exist due to having more than one chiral center in the molecule), and geometric isomers (cis / trans isomers). The present invention relates to every possible stereoisomer of the compound of Formula I, i.e. single enantiomers or diastereomers, and mixtures thereof.

[0130] The compounds according to the invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or exhibit different biological properties such as activity. The present invention relates to amorphous and crystalline compounds according to the invention, mixtures of different crystalline states of the corresponding compounds according to the invention, and amorphous or crystalline salts thereof.

[0131] The term "tautomer" encompasses isomers derived from compounds of formula I by H atom displacement involving at least one H atom located on a nitrogen, oxygen or sulfur atom. Examples of tautomeric forms are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms, and the like.

[0132] The term "stereoisomer" encompasses optical isomers, such as enantiomers or diastereomers (the latter existing due to more than one chiral center in a molecule), and geometric isomers (cis / trans isomers).

[0133] Depending on the substitution pattern, the compounds of the formula I may have one or more chiral centers, in which case they exist as mixtures of enantiomers or diastereomers. A chiral center is a radical carrying 1 The present invention provides pure enantiomers or diastereomers of compound I and mixtures thereof, as well as the use according to the invention of 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.

[0134] The term N-oxide relates to a form of compound I in which at least one nitrogen atom is present in oxidized form (as NO). More precisely, it relates to any compound of the invention having at least one tertiary nitrogen atom oxidized to an N-oxide moiety. The N-oxide of compound I can be obtained by oxidation of, for example, a ring nitrogen atom of an N-heterocycle, such as that present in Ar or R, with a suitable oxidizing agent (such as a peroxycarboxylic acid or other peroxide). 11 The compounds of the present invention can be prepared by using the pyridine or pyrimidine ring in the ring or the imino-nitrogen present in the central tricyclic core. A person skilled in the art knows whether and at which positions the compounds of the present invention can form N-oxides.

[0135] The salts of the compounds of formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a conventional manner, for example, by reacting the compound with an acid of the anion in question, if the compound of formula I has a basic functional group, or by reacting an acidic compound of formula I with a suitable base.

[0136] Suitable agriculturally or veterinarily acceptable salts are especially salts or acid addition salts of those cations of the following acids, the cations and anions of which are known and accepted in the art for forming agriculturally or veterinarily acceptable salts, respectively, and which do not have any adverse effect on the action of the compounds according to the invention. Suitable cations are in particular alkali metal (preferably lithium, sodium and potassium) ions, alkaline earth metal (preferably calcium, magnesium and barium) ions and transition metal (preferably manganese, copper, zinc and iron) ions, and also ammonium (NH 4+) and substituted ammonium in which 1 to 4 hydrogen atoms are replaced by C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or -CH2-phenyl. Examples of substituted ammonium ions include methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, in addition to phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium. Suitable veterinarily acceptable acid addition salts (e.g., salts formed from compounds of formula I containing a basic nitrogen atom, such as an amino group) include salts with inorganic acids, such as hydrochlorides, sulfates, phosphates and nitrates, and salts with organic acids, such as acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methanesulfinic acid, methanesulfonic acid and succinic acid.

[0137] Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. These can be formed by reacting compounds of formula I with acids of the corresponding anions, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

[0138] As used herein, the term "invertebrate pests" encompasses animal species, such as insects, arachnids and nematodes, which may infest plants, thereby causing substantial damage to the infested plants, and ectoparasites, which may infest animals, particularly warm-blooded animals, such as, for example, mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the infested animals.

[0139] The term "plant propagation material" should be construed as representing all propagation parts of a plant such as seeds and asexual plant materials such as cuttings and tubers (e.g., potatoes) that can be used for propagating plants. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, branches, buds and other plant parts, including rice seedlings and seedlings that are transplanted after germinating from the soil or after emerging. Plant propagation material can be preventively processed with plant protection compounds before or when planting or transplanting. The seedling can also be protected by soaking or pouring all or part of the processing before transplanting.

[0140] The term "plant" includes any type of plant, including "modified plants", in particular "cultivated plants".

[0141] The term "modified plant" refers to any wild-type species or related species or genera of cultivated plants.

[0142] The term "cultivated plants" is understood to include plants that have been bred, mutagenized, or genetically engineered, 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). Genetically modified plants are plants whose genetic material has been modified using recombinant DNA technology in a manner that would not readily be obtained by hybridization, mutation, or natural recombination under natural circumstances. Typically, one or more genes are integrated into the genetic material of the genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modifications of proteins, oligopeptides, or polypeptides, for example, by glycosylation or polymer addition such as prenylated, acetylated, or farnesylated moieties or PEG moieties.

[0143] Plants that have been modified by breeding, mutagenesis or genetic engineering to be tolerant to the application of particular classes of herbicides, such as auxin herbicides, such as dicamba or 2,4-D; bleach herbicides, such as hydroxyphenylpyruvate 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, for example, as a result of conventional breeding or genetic engineering methods. Furthermore, plants have been genetically modified multiple times to be resistant to various classes of herbicides, such as resistance to both glyphosate and glufosinate or resistance to both glyphosate and an herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin inhibitors or ACCase inhibitors. These herbicide resistance technologies are described, for example, in Pest Management Science 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185; and references cited therein. Several cultivated plants have been rendered tolerant to herbicides by conventional breeding methods (mutagenesis), for example to imidazolinones such as imazamox. Summer rapeseed (Canola, BASF SE, Germany), or tolerant to sulfonylureas such as bensulfuron-methyl Sunflower (DuPont, USA). Genetic engineering methods have been used to make cultivated plants such as soybean, cotton, corn, sugar beet and rapeseed tolerant to herbicides such as glyphosate and glufosinate, some of which are sold under the trade names (Glyphosate tolerant, Monsanto, USA), (Imidazolinone resistant, BASF, Germany) and (Glufosinate-tolerant, Bayer CropScience, Germany) is commercially available.

[0144] Furthermore, plants are covered which are capable of synthesizing one or more insecticidal proteins by the use of recombinant DNA technology, in particular those known from bacteria of the genus Bacillus, in particular Bacillus thuringiensis, such as delta-endotoxins, for example CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; asexual insecticidal proteins (VIPs), for example VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria that colonize nematodes, for example Photorhabdus species or Xenorhabdus species; toxins produced by animals, such as scorpion toxins, spider toxins, wasp toxins or other insect-specific neurotoxins; Toxins produced by fungi, such as streptomycin, plant lectins, such as pea or barley lectins; lectins; protease inhibitors, such as trypsin inhibitors, serine protease inhibitors, potato glycoproteins, cysteine ​​protease inhibitors or papain inhibitors; ribosome inactivating proteins (RIPs), such as ricin, maize-RIP, abrin, luffain, saporin or xenotoxin; steroid metabolizing enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitor or HMG-CoA-reductase; ion channel blockers, such as sodium or calcium channel blockers; juvenile hormone esterase; diuretic hormone receptor (helicokinin receptor); stilbene synthase, bibenzyl synthase, chitinase or glucanase. In the context of the present invention, these insecticidal proteins or toxins should also be understood as protoxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by new combinations of protein domains (see, for example, WO 02 / 015701). Such toxins or other examples of genetically modified plants capable of synthesizing such toxins are for example disclosed in EP-A 374 753, WO 93 / 007278, WO 95 / 34656, EP-A 427 529, EP-A 451 878, WO 03 / 18810 and WO 03 / 52073. The method for producing such genetically modified plants is generally well known to those skilled in the art and is for example described in the above-mentioned publications. These insecticide proteins contained in genetically modified plants give the plants producing these proteins to harmful pests from all arthropod taxa, especially beetles (Coleoptera (Coleoptera)), dipteran insects (Diptera (Diptera)) and moths (Lepidoptera (Lepidoptera)) and nematodes (Nematoda) tolerance. Genetically modified plants which are able to synthesize one or more insecticidal proteins are described, for example, in the above-mentioned publications, and some of them are commercially available, such as (corn varieties that produce Cry1Ab toxin), Plus (corn varieties producing Cry1Ab and Cry3Bb1 toxins), (corn varieties that produce Cry9c toxin), RW (a corn variety producing Cry34Ab1, Cry35Ab1, and the enzyme phosphinothricin-N-acetyltransferase [PAT]); 33B (cotton variety producing Cry1Ac toxin), I (cotton variety producing Cry1Ac toxin), II (cotton varieties producing Cry1Ac and Cry2Ab2 toxins); (cotton varieties producing VIP-toxin); (potato varieties producing Cry3A toxin); from Syngenta Seeds SAS, France Bt11 (e.g. CB) and Bt176 (corn varieties producing Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta Seeds, France (a corn variety producing a modified form of Cry3A toxin, see WO 03 / 018810), MON 863 from Monsanto Europe, Belgium (a corn variety producing Cry3Bb1 toxin), IPC531 from Monsanto Europe, Belgium (a cotton variety producing a modified form of Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (a corn variety producing Cry1F toxin and PAT enzyme).

[0145] In addition, also covered are plants that can synthesize one or more proteins to enhance the resistance or tolerance of plants to bacteria, viruses or fungal pathogens by using recombinant DNA technology. Examples of such proteins are so-called "pathogenesis-related proteins" (PR proteins, see, for example, EP-A 392 225), plant disease resistance genes (e.g., potato varieties expressing resistance genes to Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum) or T4-lysozyme (e.g., potato varieties capable of synthesizing these proteins that have enhanced resistance to bacteria such as Erwinia amylvora). Methods for producing such genetically modified plants are generally known to those skilled in the art and are, for example, described in the above-mentioned publications.

[0146] Furthermore, also covered are those plants which, by the use of recombinant DNA techniques, are able to synthesize one or more proteins to increase the productivity of the plant (e.g. biomass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to harmful organisms and fungal, bacterial or viral pathogens.

[0147] Furthermore, plants are covered which, by using recombinant DNA technology, contain altered amounts of substances or new substances, in particular to improve human or animal nutrition, such as oil crops which produce health-promoting long-chain ω-3 fatty acids or unsaturated ω-9 fatty acids (e.g. Oilseed rape, DOW Agro Sciences, Canada.

[0148] Furthermore, plants are covered which have altered or novel substance contents by the use of recombinant DNA techniques, in particular to improve raw material production, such as potatoes which produce increased amounts of amylopectin (e.g. Potatoes, BASF, Germany).

[0149] The organic moieties mentioned in the definitions of the variables above, like the term halogen, are collectively referred to as separate lists of individual members. n -C m The possible number of carbon atoms in the group is indicated in each case.

[0150] The term halogen denotes in each case F, Br, Cl or I, in particular F, Cl or Br.

[0151] As used herein and in the alkyl portion of alkoxy, alkylthio, etc., the term "alkyl" refers to a saturated straight-chain or branched hydrocarbon radical having 1 to 2 ("C1-C2-alkyl"), 1 to 3 ("C1-C3-alkyl"), 1 to 4 ("C1-C4-alkyl"), or 1 to 6 ("C1-C6-alkyl") carbon atoms. C1-C2-alkyl is CH3 or C2H5. C1-C3-alkyl is additionally propyl and isopropyl. C1-C4-alkyl is additionally butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), or 1,1-dimethylethyl (tert-butyl). C1-C6-Alkyl is furthermore also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl.

[0152] As used herein, the term "haloalkyl", which is also denoted as "partially or fully halogenated alkyl", refers to straight-chain or branched alkyl groups having 1 to 2 ("C1-C2-haloalkyl"), 1 to 3 ("C1-C3-haloalkyl"), 1 to 4 ("C1-C4-haloalkyl") or 1 to 6 ("C1-C6-haloalkyl") carbon atoms (as mentioned above), wherein some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: In particular, C1-C2-haloalkyl is such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, or pentafluoroethyl. C1-C3-haloalkyl is furthermore, for example, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl, etc. Examples of C1-C4-haloalkyl, in addition to those mentioned for C1-C3-haloalkyl, are 4-chlorobutyl and the like.

[0153] As used herein, the term "alkylene" (or alkanediyl) refers in each case to an alkyl radical as defined above, in which one hydrogen atom at any position of the carbon backbone is replaced by another binding site, thus forming a divalent moiety. Alkylene preferably has 1 to 6 carbon atoms (C1-C6-alkylene), 2 to 6 carbon atoms (C2-C6-alkylene), in particular 1 to 4 carbon atoms (C1-C4-alkylene) or 2 to 4 carbon atoms (C2-C4-alkylene). Examples of alkylene groups are methylene (CH2), 1,1-ethanediyl, 1,2-ethanediyl, 1,3-propylenediyl, 1,2-propylenediyl, 2,2-propylenediyl, 1,4-butanediyl, 1,2-butanediyl, 1,3-butanediyl, 2,3-butanediyl, 2,2-butanediyl, 1,5-pentanediyl, 2,2-dimethylpropylene-1,3-diyl, 1,3-dimethyl-1,3-propylenediyl, 1,6-hexanediyl, and the like.

[0154] As used herein, the term "alkenyl" refers to a monounsaturated straight or branched hydrocarbon radical having 2 to 3 ("C2-C3-alkenyl"), 2 to 4 ("C2-C4-alkenyl"), or 2 to 6 ("C2-C6-alkenyl") carbon atoms and a double bond at any position, for example, C2-C3-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, or 1-methylethenyl; C2-C4-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, or 2-methyl-2-propenyl;C2-C6-alkenyl, such as 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl , 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl, etc.;

[0155] As used herein, the term "alkynyl" refers to a straight or branched hydrocarbon group having 2 to 3 ("C2-C3-alkynyl"), 2 to 4 ("C2-C4-alkynyl"), or 2 to 6 ("C2-C6-alkynyl") carbon atoms and one or two triple bonds at any position, for example, C2-C3-alkynyl, such as ethynyl, 1-propynyl, or 2-propynyl; C2-C4-alkynyl, such as ethynyl, 1-propynyl, or 2-propynyl; propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, etc.; C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, Alkynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, etc.

[0156] As used herein, the term "cycloalkyl" refers to a monocyclic, bicyclic, or polycyclic saturated hydrocarbon radical, particularly having 3 to 6 ("C3-C6-cycloalkyl"), 3 to 5 ("C3-C5-cycloalkyl"), or 3 to 4 ("C3-C4-cycloalkyl") carbon atoms. Examples of monocyclic radicals having 3 to 4 carbon atoms include cyclopropyl and cyclobutyl. Examples of monocyclic radicals having 3 to 5 carbon atoms include cyclopropyl, cyclobutyl, and cyclopentyl. Examples of monocyclic radicals having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of monocyclic radicals having 3 to 8 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atoms include bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.

[0157] As used herein, the term "cycloalkoxy" refers to a cycloalkyl radical as defined above, in particular a monocyclic cycloalkyl radical, in particular having 3 to 6 ("C3-C6-cycloalkoxy"), or 3 to 5 ("C3-C5-cycloalkoxy"), or 3 to 4 ("C3-C4-cycloalkoxy") carbon atoms, which is bound to the remainder of the molecule via an oxygen atom.

[0158] The term "cycloalkyl-C1-C4-alkyl" refers to a C3-C8-cycloalkyl group ("C3-C8-cycloalkyl-C1-C4-alkyl") as defined above, preferably a C3-C6-cycloalkyl group ("C3-C6-cycloalkyl-C1-C4-alkyl"), more preferably a C3-C4-cycloalkyl group ("C3-C4-cycloalkyl-C1-C4-alkyl") (preferably a monocyclic cycloalkyl group), which is bound to the remainder of the molecule via a C1-C4-alkyl group as defined above. Examples of C3-C4-cycloalkyl-C1-C4-alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl and cyclobutylpropyl. Examples of C3-C6-cycloalkyl-C1-C4-alkyl, in addition to those mentioned for C3-C4-cycloalkyl-C1-C4-alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.

[0159] The term "C1-C2-alkoxy" is a C1-C2-alkyl group as defined above attached via an oxygen atom. The term "C1-C3-alkoxy" is a C1-C3-alkyl group as defined above attached via an oxygen atom. The term "C1-C4-alkoxy" is a C1-C4-alkyl group as defined above attached via an oxygen atom. The term "C1-C6-alkoxy" is a C1-C6-alkyl group as defined above attached via an oxygen atom. The term "C1-C 10 -alkoxy" is a C1-C2-alkyl group as defined above attached via an oxygen atom 10-alkyl radical. C1-C2-Alkoxy is OCH3 or OC2H5. C1-C3-Alkoxy is further exemplified by n-propoxy and 1-methylethoxy (isopropoxy). C1-C4-Alkoxy is further exemplified by butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). C1-C6-Alkoxy is furthermore, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy. C1-C8-Alkoxy is furthermore, for example, heptoxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. 10 -Alkoxy is furthermore, for example, nonyloxy, decyloxy and positional isomers thereof.

[0160] The term "C1-C2-haloalkoxy" is a C1-C2-haloalkyl group as defined above attached via an oxygen atom. The term "C1-C3-haloalkoxy" is a C1-C3-haloalkyl group as defined above attached via an oxygen atom. The term "C1-C4-haloalkoxy" is a C1-C4-haloalkyl group as defined above attached via an oxygen atom. The term "C1-C6-haloalkoxy" is a C1-C6-haloalkyl group as defined above attached via an oxygen atom. C1-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5. C1-C3-haloalkoxy is furthermore, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy or 1-(CH2Br)-2-bromoethoxy. C1-C4-haloalkoxy is furthermore, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C1-C6-Haloalkoxy is furthermore, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

[0161] As used herein, the term "C1-C6-alkoxy-C1-C4-alkyl" refers to a straight-chain or branched alkyl group as defined above having 1 to 4 carbon atoms in which one hydrogen atom is replaced by a C1-C6-alkoxy group. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl, 1-isobutoxyethyl, 1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1-methoxypropyl , 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl, 1-isobutoxypropyl, 1-tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl, 2-sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl, 3-tert-butoxypropyl, etc.

[0162] As used herein, the term "alkoxyalkoxy" refers to an alkoxyalkyl radical as defined above, in particular a C1-C6-alkoxy-C1-C4-alkyl radical, which is bound to the remainder of the molecule via an oxygen atom. Examples thereof are OCH2-OCH3, OCH2-OC2H5, n-propoxymethoxy, OCH2-OCH(CH3)2, n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH2-OC(CH3)3, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, and the like.

[0163] The substituent "oxo" replaces CH2 with a C(=O) group.

[0164] The term "aryl" refers to phenyl and bicyclic or polycyclic carbocycles having at least one fused phenylene ring, which are bound to the rest of the molecule. Examples of bicyclic or polycyclic carbocycles having at least one phenylene ring include naphthyl, tetrahydronaphthyl, indanyl, indenyl, anthracenyl, fluorenyl, and the like.

[0165] The term "aryl-C1-C4-alkyl" relates to a C1-C4-alkyl group as defined above in which one of the hydrogen atoms has been replaced by an aryl radical, in particular a phenyl radical. Specific examples of aryl-C1-C4-alkyl groups include -CH2-phenyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenyl-1-propyl and 2-phenyl-2-propyl.

[0166] The term "aryloxy-Ci-C4-alkyl" relates to a C1-C4-alkyl group as defined above in which one hydrogen atom has been replaced by an aryloxy radical, in particular a phenoxy radical. Specific examples of aryloxy-Ci-C4-alkyl groups include phenoxymethyl, 1-phenoxyethyl, 2-phenoxyethyl, 1-phenoxypropyl, 2-phenoxypropyl, 3-phenoxy-1-propyl and 2-phenoxy-2-propyl.

[0167] The term "aryl-C1-C4-carbonyl" relates to an aryl radical as defined above, in particular a phenyl radical, which is bound to the remainder of the molecule via a carbonyl group. Specific examples of arylcarbonyl groups include benzoyl, 1-naphthoyl and 2-naphthoyl.

[0168] The term "heteroaryl" relates to an aromatic heterocyclic radical or heterocycle having 5 or 6 ring atoms (5- or 6-membered heteroaryl) and being monocyclic or having 8, 9 or 10 ring atoms and being bicyclic. A heteroaryl radical will generally have at least one ring atom selected from O, S and N, in the case of N, which may be an imino-nitrogen or amino-nitrogen radical carrying hydrogen or a radical different from hydrogen. A heteroaryl radical may have 1, 2, 3 or 4 further nitrogen atoms as ring members, which further nitrogen atoms are imino-nitrogens. Examples of 5- or 6-membered heteroaryl groups include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-Imidazol-1-yl, 1,3,4-triazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl and 1,3,5-triazin-2-yl. Examples of 8-, 9-, or 10-membered heteroaryl groups include, for example, quinolinyl, isoquinolinyl, cinnolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuranyl, benzothienyl, benzo[b]thiazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, imidazo[1,2-a]pyridin-2-yl, thieno[3,2-b]pyridin-5-yl, imidazo-[2,1-b]-thiazol-6-yl, and 1,2,4-triazolo[1,5-a]pyridin-2-yl.

[0169] Examples of N-bound 5-, 6-, 7-, or 8-membered saturated heterocyclic groups or heterocycles include: pyrrolidin-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, isoxazolidin-2-yl, thiazolidin-3-yl, isothiazolidin-2-yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-4-yl, azepan-1-yl, and the like.

[0170] The term "heteroaryl-Ci-C4-alkyl" relates to a Ci-C4-alkyl group as defined above in which one of the hydrogen atoms has been replaced by a heteroaryl radical, in particular a pyridyl radical. Specific examples of heteroaryl-Ci-C4-alkyl groups include 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, 1-(2-pyridyl)ethyl, 2-(2-pyridyl)ethyl, 1-(3-pyridyl)ethyl, 2-(3-pyridyl)ethyl, 1-(4-pyridyl)ethyl, 2-(4-pyridyl)ethyl, and the like.

[0171] The term "heteroaryloxy-Ci-C4-alkyl" relates to a C1-C4-alkyl group as defined above in which one hydrogen atom has been replaced by a heteroaryloxy group, in particular a pyridyloxy group. Specific examples of heteroaryloxy-Ci-C4-alkyl include 2-pyridyloxymethyl, 3-pyridyloxymethyl, 4-pyridyloxymethyl, 1-(2-pyridyloxy)ethyl, 2-(2-pyridyloxy)ethyl, 1-(3-pyridyloxy)ethyl, 2-(3-pyridyloxy)ethyl, 1-(4-pyridyloxy)ethyl, 2-(4-pyridyloxy)ethyl, and the like.

[0172] The term "heteroaryl-C1-C4-carbonyl" relates to a heteroaryl group as defined above, in particular a C-bound heteroaryl group, for example 2-, 3- or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 1-, 2- or 3-pyrrolyl, 2- or 4-pyrimidinyl, pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl, which is bound to the remainder of the molecule via a carbonyl group.

[0173] If not otherwise stated, the term "substituted" means substituted by 1, 2 or up to the maximum possible number of substituents. If not otherwise stated, if there are more than one substituents as defined in the compounds of formula I, they are independent of each other and may be the same or different.

[0174] With respect to the variables, examples of compounds of formula I are,

[0175] In a preferred embodiment, B 1 、B 2 and B 3 At most two of them can be N;

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

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

[0178] In another preferred embodiment, B 1 It's CR B1 , B 2 is N, and B 3 It's CR B3 ;

[0179] In another preferred embodiment, B1 It's CR B1 , B 2 is N, and B 3 It is N;

[0180] In another preferred embodiment, B 1 It's N, B 2 is N, and B 3 It's CR B3 ;

[0181] In another preferred embodiment, B 1 It's CR B1 , and B 2 Is N or CR B2 , B 3 Is N or CR B3 ;

[0182] In another preferred embodiment, B 3 It's CR B3 , and B 1 Is N or CR B2 , B 2 Is N or CR B3 .

[0183] In a preferred embodiment, R 1 is H, halogen, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0184] In another preferred embodiment, R 1 is H, halogen, C1-C6-alkyl or C3-C6-cycloalkyl;

[0185] In another preferred embodiment, R 1 is H, halogen or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen or CN;

[0186] In another preferred embodiment, R 1 is H or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen or CN;

[0187] In another preferred embodiment, R 1 is C1-C6-alkyl, which is unsubstituted or substituted by halogen or CN;

[0188] In another preferred embodiment, R 1 is C1-C6-alkyl, which is unsubstituted;

[0189] In another preferred embodiment, R 1is C1-C6-alkyl, which is substituted by halogen or CN;

[0190] In another preferred embodiment, R 1 is C3-C6-cycloalkyl, which is unsubstituted or substituted by halogen or CN;

[0191] In another preferred embodiment, R 1 is a C3-C6-cycloalkyl group, which is unsubstituted;

[0192] In another preferred embodiment, R 1 is C3-C6-cycloalkyl, which is substituted by halogen or CN;

[0193] In another preferred embodiment, R 1 is H or halogen;

[0194] In another preferred embodiment, R 1 It is H;

[0195] In another preferred embodiment, R 1 It is a halogen;

[0196] In another preferred embodiment, R 1 is H, Cl, CH3 or cyclopropyl;

[0197] In another preferred embodiment, R 1 Is H or NR 6 R 7 ;

[0198] In another preferred embodiment, R 1 It is NR 6 R 7 .

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

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

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

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

[0203] In another 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, wherein these alkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN or C1-C6-alkyl;

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

[0205] Table Rx:

[0206]

[0207] In another preferred embodiment, R 6 and R 7 Independently selected from Rx-1, Rx-2, Rx-7 and Rx-8, more preferably selected from Rx-1 and Rx-7.

[0208] In a preferred embodiment, R 2 is H, halogen, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0209] In another preferred embodiment, R 2 is H, halogen, C1-C6-alkyl or C3-C6-cycloalkyl;

[0210] In another preferred embodiment, R 2is H, halogen or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen or CN;

[0211] In another preferred embodiment, R 2 is H or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen or CN;

[0212] In another preferred embodiment, R 2 is C1-C6-alkyl, which is unsubstituted or substituted by halogen or CN;

[0213] In another preferred embodiment, R 2 is C1-C6-alkyl, which is unsubstituted;

[0214] In another preferred embodiment, R 2 is C1-C6-alkyl, which is substituted by halogen or CN;

[0215] In another preferred embodiment, R 2 is C3-C6-cycloalkyl, which is unsubstituted or substituted by halogen or CN;

[0216] In another preferred embodiment, R 2 is a C3-C6-cycloalkyl group, which is unsubstituted;

[0217] In another preferred embodiment, R 2 is C3-C6-cycloalkyl, which is substituted by halogen or CN;

[0218] In another preferred embodiment, R 2 is H or halogen;

[0219] In another preferred embodiment, R 2 It is H;

[0220] In another preferred embodiment, R 2 It is a halogen;

[0221] In another preferred embodiment, R 2 It is H, Cl, Br, F, CH3, C2H5, n-C3H7, isopropyl, cyclopropyl, CH2F, CHF2 or CF3.

[0222] In another preferred embodiment, R 2 is H, CH3, C2H5, isopropyl or cyclopropyl;

[0223] In another preferred embodiment, R 2 It is H;

[0224] In another preferred embodiment, R 2It is CH3;

[0225] In another preferred embodiment, R 2 It is C2H5;

[0226] In another preferred embodiment, R 2 is isopropyl;

[0227] In another preferred embodiment, R 2 It is cyclopropyl.

[0228] In a 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 these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0229] 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 these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0230] In another preferred embodiment, R B1 、R B2 、R B3 and R B4 are independently H, halogen or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen;

[0231] In another preferred embodiment, R B1 、R B2 、R B3 and R B4 are independently H, Cl, Br, F, CN, CH3, C2H5, n-C3H7, isopropyl, cyclopropyl, CF3, CH2F, OCH3 or OCHF2.

[0232] In another preferred embodiment, R B1 、R B2 、R B3 and R B4 are independently H, Cl, Br, F, CN, CH3, isopropyl, OCH3 or OCHF2.

[0233] In another preferred embodiment, R B1 and R B4are independently H, Cl or CH3.

[0234] In another preferred embodiment, R B2 and R B3 are independently H, Cl, Br, F, CN, CH3, isopropyl, cyclopropyl, OCH3 or OCHF2.

[0235] In another preferred embodiment, R B2 and R B3 are independently H, Cl, F, CN, CH3 or OCH3;

[0236] In another preferred embodiment, R B2 and R B3 are independently H or Cl.

[0237] In a preferred embodiment, Q is #-C(=O)-N(R 5 )-, where # indicates the same as Ar 1 connection;

[0238] In another preferred embodiment, Q is #-N(R 5 )-C(=O)-, where # represents the 1 connection.

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

[0240] In another preferred embodiment, R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0241] In another preferred embodiment, R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted;

[0242] In another preferred embodiment, R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are substituted by halogen or CN;

[0243] In another preferred embodiment, R 5 is H, CH3, C2H5 or -CH2-cyclopropyl;

[0244] In a preferred embodiment, D is DA;

[0245] In a preferred embodiment, R 3 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0246] In another preferred embodiment, R 3 is H or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen or CN;

[0247] In another preferred embodiment, R 3 is H or C3-C6-cycloalkyl, wherein these cycloalkyl moieties are unsubstituted or substituted by halogen or CN;

[0248] In another preferred embodiment, R 3 It is H;

[0249] In another preferred embodiment, R 3 is H, and DA exists in either of the following tautomeric forms D3 and D4;

[0250]

[0251] In a preferred embodiment, R 4 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkyl, -O-(C=O)-C1-C6-alkoxy or CN;

[0252] In another preferred embodiment, R 4 is H or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkyl, -O-(C=O)-C1-C6-alkoxy or CN;

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

[0254] In another preferred embodiment, R 4 It is H;

[0255] In another preferred embodiment, R 4 is H, and DA exists in either of the following tautomeric forms D1 and D2;

[0256]

[0257] In another preferred embodiment, D is DB, wherein B is a 5- or 6-membered carbocyclic group, wherein 1 or 2 CH2 moieties of the carbocyclic group may be replaced by a carbonyl group, wherein the carbocyclic group is unsubstituted or replaced by R h replace;

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

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

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

[0261] In another preferred embodiment, D is DB selected from D5 to D7, and the carbocyclic groups of D5 to D7 are unsubstituted or substituted with 1 or 2 substituents R h replace,

[0262]

[0263] In another preferred embodiment, D is a group selected from the group consisting of D5 to D7 moieties, which are unsubstituted or substituted with 1 or 2 substituents R h replace,

[0264]

[0265] In another preferred embodiment, D is DB selected from D5 to D7, and wherein the carbocyclic group of the D5 to D7 moieties is unsubstituted;

[0266] In another preferred embodiment, D is DB selected from D5 to D7, and the carbocyclic group of D5 to D7 is replaced by 1 or 2 substituents R h replace;

[0267] In another preferred embodiment, D is selected from DA, D5, D6 and D7 as defined herein;

[0268] In another preferred embodiment, D is selected from DA, D5, D6 and D7, wherein the carbocyclic groups of D5, D6 and D7 are unsubstituted or substituted with 1 or 2 substituents R h replace;

[0269] In another preferred embodiment, D is DA or D5, wherein D5 is unsubstituted or substituted with one substituent R h replace;

[0270] In another preferred embodiment, D is selected from DA or D5, wherein the carbocyclic group of D5 is replaced by one substituent R h replace;

[0271] In another preferred embodiment, D is selected from DA or D5, wherein the carbocyclic group of D5 is unsubstituted;

[0272] In another preferred embodiment, D is D5, wherein the carbocyclic group of D5 is unsubstituted or substituted with one substituent R h replace;

[0273] In a preferred embodiment, Ar 1 is phenyl, which is unsubstituted or replaced by R Ar1 replace.

[0274] In another preferred embodiment, Ar 1 is a 5- or 6-membered heteroaryl group which is unsubstituted or replaced by R Ar1 replace;

[0275] In a more preferred embodiment, Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridinyl, which is unsubstituted or replaced by R Ar1 replace.

[0276] In a preferred embodiment, R Ar1 is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f In another preferred embodiment, Ar 1 is a 5- or 6-membered heteroaryl group which is unsubstituted or replaced by R Ar1 replace;

[0277] C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、-N=S(=O)-(C1-C6-alkyl)2、SO2NRb R c or S(=O) m R e ;

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

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

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

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

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

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

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

[0285] R Ar1is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f replace;

[0286] C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、-N=S(=O)-(C1-C6-alkyl)2、SO2NR b R c or S(=O) m R e ;

[0287] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0288] R d is H or C1-C6-alkyl;

[0289] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0290] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0291] m is 0, 1, or 2.

[0292] In another preferred embodiment of the compound of formula I, wherein

[0293] Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridinyl, which is unsubstituted or replaced by R Ar1 replace;

[0294] R Ar1is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and C3-C6-heterocyclyl moieties are unsubstituted or replaced by R f replace;

[0295] 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 ;

[0296] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0297] R d is H or C1-C6-alkyl;

[0298] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0299] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0300] m is 0, 1, or 2.

[0301] In another preferred embodiment, Ar 1 Selected from Ar shown in Table Ar1 1 -1 to Ar 1 -26,

[0302] Table Ar1:

[0303]

[0304]

[0305] In another preferred embodiment, Ar 1 Selected from Ar 1 -1 to Ar 1 -17;

[0306] In another preferred embodiment, Ar 1 Selected from Ar 1 -1 to Ar 1 -9;

[0307] In another preferred embodiment, Ar 1 Selected from Ar 1 -1 to Ar 1 -8;

[0308] In another preferred embodiment, Ar 1 Selected from Ar 1 -1 to Ar 1 -3;

[0309] In a preferred embodiment, Ar 2 is phenyl, which is unsubstituted or replaced by R Ar2 replace;

[0310] In another preferred embodiment, Ar 2 is a 5- or 6-membered heteroaryl group which is unsubstituted or replaced by R Ar2 replace;

[0311] In another preferred embodiment, Ar 2 is phenyl, pyrimidinyl, thienyl, thiazolyl or pyridinyl, which is unsubstituted or replaced by R Ar2 replace.

[0312] In a 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-cycloalkyloxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyloxy-C1-C4-alkyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted by halogen;

[0313] C(=O)-OR a NR b R c or C1-C6-alkylene-CN;

[0314] In another preferred embodiment, R Ar2 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, wherein these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0315] or NR b R c ;

[0316] In another preferred embodiment, R Ar2 Halogen, CN, NR b R c , C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, wherein these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0317] In another preferred embodiment, R Ar2 It is NR b R c ;

[0318] In another preferred embodiment, R Ar2 is halogen, CN, C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen;

[0319] In another preferred embodiment, R Ar2 is halogen or C1-C6-alkyl, wherein these alkyl moieties are unsubstituted or substituted by halogen;

[0320] In another preferred embodiment, R Ar2 is halogen or C1-C6-alkyl;

[0321] In another preferred embodiment, R Ar2 It is a halogen;

[0322] In another preferred embodiment, R Ar2 is a halogen or CN;

[0323] In another preferred embodiment, Ar 2 Selected from Ar shown in Table Ar2 2 -1 to Ar 2 -20,

[0324] Table Ar2:

[0325]

[0326]

[0327] In another preferred embodiment, Ar 2 Selected from Ar 2 -1 to Ar 2 -13;

[0328] In another preferred embodiment, Ar 2Selected from Ar 2 -1 to Ar 2 -3;

[0329] In one embodiment, R a 、R b and R c are identical or different H, C1-C6-alkyl, C2-C6-alkenyl, which are unsubstituted or substituted by halogen;

[0330] In another preferred embodiment, R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0331] In a preferred embodiment, R d It is H;

[0332] In another preferred embodiment, R d It is C1-C6-alkyl.

[0333] In a preferred embodiment, R e is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl;

[0334] In another preferred embodiment, R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0335] In a 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 is unsubstituted or substituted by halogen;

[0336] In another preferred embodiment, R f is halogen, OH, CN or C1-C6-alkyl.

[0337] In a preferred embodiment, R h is halogen or C1-C6-alkyl;

[0338] In a preferred embodiment, m is 0;

[0339] In another preferred embodiment, m is 1;

[0340] In another preferred embodiment, m is 2;

[0341] In another preferred embodiment, m is 0 or 1;

[0342] In another preferred embodiment, m is 1 or 2.

[0343] In another preferred embodiment of the compound of formula I, wherein

[0344] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-;

[0345] D is DA, D5, D6 or D7, preferably D5;

[0346] B 1 Is N or CR B1 , B 2 It's CR B2 , and B 3 It's CR B3 ;

[0347] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl or C1-C6-alkoxy, where these alkyl and alkoxy moieties are unsubstituted or substituted by halogen;

[0348] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl;

[0349] R 1 is H, halogen, C1-C6-alkyl or C3-C6-cycloalkyl;

[0350] R 2 is H or C1-C6-alkyl;

[0351] R 3 is H or C1-C6-alkyl;

[0352] R 4 is H or C1-C6-alkyl;

[0353] Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridinyl, which is unsubstituted or replaced by R Ar1 replace;

[0354] R Ar1is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f Substitution; C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、-N=S(=O)-(C1-C6-alkyl)2、SO2NR b R c or S(=O) m R e ;

[0355] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0356] R d is H or C1-C6-alkyl;

[0357] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0358] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0359] m is 0, 1, or 2.

[0360] In another preferred embodiment of the compound of formula I, wherein

[0361] Q is -C(=O)-N(R 5 )-;

[0362] D is DB, preferably D5;

[0363] B 1 Is N or CR B1 , B 2 It's CR B2 , and B 3It's CR B3 ;

[0364] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0365] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl;

[0366] R 1 is H, halogen, C1-C6-alkyl or C3-C6-cycloalkyl;

[0367] R 2 is C1-C6-alkyl;

[0368] Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridinyl, which is unsubstituted or replaced by R Ar1 replace;

[0369] R Ar1 is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and C3-C6-heterocyclyl moieties are unsubstituted or replaced by R f replace;

[0370] NR b R c 、C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、-N=S(=O)-(C1-C6-

[0371] alkyl)2 or S(=O) m R e ;

[0372] Ar 2 is phenyl, which is unsubstituted or replaced by R Ar2 replace;

[0373] R Ar2is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, wherein these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0374] or NR b R c ;

[0375] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0376] R d is H or C1-C6-alkyl;

[0377] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0378] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0379] m is 0, 1, or 2.

[0380] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.1 to A.10,

[0381]

[0382] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.1 to A.5. In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.6 to A.10. In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.1 and A.6;

[0383] In another preferred embodiment, the compound of formula I is selected from the compounds of formula A.2 and A.7;

[0384] In another preferred embodiment, the compound of formula I is selected from the compounds of formula A.3 and A.8;

[0385] In another preferred embodiment, the compound of formula I is selected from the compounds of formula A.4 and A.9;

[0386] In another preferred embodiment, the compound of formula I is selected from the compounds of formula A.5 and A.10;

[0387] In another preferred embodiment, the compound of formula I is A.1;

[0388] In another preferred embodiment, the compound of formula I is A.2;

[0389] In another preferred embodiment, the compound of formula I is A.3;

[0390] In another preferred embodiment, the compound of formula I is A.4;

[0391] In another preferred embodiment, the compound of formula I is A.5;

[0392] In another preferred embodiment, the compound of formula I is A.6;

[0393] In another preferred embodiment, the compound of formula I is A.7;

[0394] In another preferred embodiment, the compound of formula I is A.8;

[0395] In another preferred embodiment, the compound of formula I is A.9;

[0396] In another preferred embodiment, the compound of formula I is A.10;

[0397] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.1 to A.5, wherein

[0398] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0399] 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;

[0400] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0401] R 2 is H or C1-C6-alkyl, preferably CH3;

[0402] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0403] R3 is H or C1-C6-alkyl;

[0404] R 4 is H or C1-C6-alkyl;

[0405] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0406] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0407] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae A.6 to A.10, wherein

[0408] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0409] 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;

[0410] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0411] R 2 is H or C1-C6-alkyl, preferably CH3;

[0412] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0413] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0414] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0415] In another preferred embodiment, the compound of formula I is selected from the compounds of formula A.1 and A.6, wherein

[0416] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0417] 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;

[0418] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0419] R 2 is H or C1-C6-alkyl, preferably CH3;

[0420] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0421] R 3 is H or C1-C6-alkyl;

[0422] R 4 is H or C1-C6-alkyl;

[0423] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1-3;

[0424] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0425] In another preferred embodiment, the compound of formula I is selected from the compounds of formula A.2 and A.7, wherein

[0426] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0427] 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;

[0428] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0429] R 2 is H or C1-C6-alkyl, preferably CH3;

[0430] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0431] R 3 is H or C1-C6-alkyl;

[0432] R 4 is H or C1-C6-alkyl;

[0433] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0434] Ar 2 Selected from Ar 2 -1 to Ar2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0435] In another preferred embodiment, the compound of formula I is selected from the compounds of formula A.3 and A.8, wherein

[0436] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0437] 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;

[0438] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0439] R 2 is H or C1-C6-alkyl, preferably CH3;

[0440] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0441] R 3 is H or C1-C6-alkyl;

[0442] R 4 is H or C1-C6-alkyl;

[0443] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0444] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0445] In another preferred embodiment, the compound of formula I is selected from the compounds of formula A.4 and A.9, wherein

[0446] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0447] 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;

[0448] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0449] R 2 is H or C1-C6-alkyl, preferably CH3;

[0450] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0451] R 3 is H or C1-C6-alkyl;

[0452] R 4 is H or C1-C6-alkyl;

[0453] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0454] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0455] In another preferred embodiment, the compound of formula I is selected from the compounds of formula A.5 and A.10, wherein

[0456] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0457] 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;

[0458] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0459] R 2 is H or C1-C6-alkyl, preferably CH3;

[0460] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0461] R 3 is H or C1-C6-alkyl;

[0462] R 4 is H or C1-C6-alkyl;

[0463] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0464] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0465] In another preferred embodiment, the compound of formula I is A.1, wherein

[0466] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R5 )-;

[0467] 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;

[0468] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0469] R 2 is H or C1-C6-alkyl, preferably CH3;

[0470] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0471] R 3 is H or C1-C6-alkyl;

[0472] R 4 is H or C1-C6-alkyl;

[0473] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0474] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0475] In another preferred embodiment, the compound of formula I is A.2, wherein

[0476] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0477] 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;

[0478] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0479] R 2 is H or C1-C6-alkyl, preferably CH3;

[0480] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0481] R 3 is H or C1-C6-alkyl;

[0482] R 4 is H or C1-C6-alkyl;

[0483] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0484] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0485] In another preferred embodiment, the compound of formula I is A.3, wherein

[0486] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0487] 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;

[0488] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0489] R 2 is H or C1-C6-alkyl, preferably CH3;

[0490] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0491] R 3 is H or C1-C6-alkyl;

[0492] R 4 is H or C1-C6-alkyl;

[0493] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0494] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0495] In another preferred embodiment, the compound of formula I is A.4, wherein

[0496] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0497] 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;

[0498] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0499] R2 is H or C1-C6-alkyl, preferably CH3;

[0500] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0501] R 3 is H or C1-C6-alkyl;

[0502] R 4 is H or C1-C6-alkyl;

[0503] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0504] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0505] In another preferred embodiment, the compound of formula I is A.5, wherein

[0506] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0507] 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;

[0508] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0509] R 2 is H or C1-C6-alkyl, preferably CH3;

[0510] R B1 、RB2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0511] R 3 is H or C1-C6-alkyl;

[0512] R 4 is H or C1-C6-alkyl;

[0513] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0514] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0515] In another preferred embodiment, the compound of formula I is A.6, wherein

[0516] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0517] 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;

[0518] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0519] R 2 is H or C1-C6-alkyl, preferably CH3;

[0520] R B1 、R B2 、R B3 and R B4are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0521] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0522] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0523] In another preferred embodiment, the compound of formula I is A.7, wherein

[0524] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0525] 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;

[0526] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0527] R 2 is H or C1-C6-alkyl, preferably CH3;

[0528] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0529] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0530] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0531] In another preferred embodiment, the compound of formula I is A.8, wherein

[0532] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0533] 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;

[0534] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0535] R 2 is H or C1-C6-alkyl, preferably CH3;

[0536] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0537] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0538] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0539] In another preferred embodiment, the compound of formula I is A.9, wherein

[0540] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0541] 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;

[0542] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0543] R 2 is H or C1-C6-alkyl, preferably CH3;

[0544] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0545] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0546] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0547] In another preferred embodiment, the compound of formula I is A.10, wherein

[0548] Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-, preferably -C(=O)-N(R 5 )-;

[0549] 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;

[0550] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0551] R 2 is H or C1-C6-alkyl, preferably CH3;

[0552] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0553] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0554] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0555] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae I.1 to I.4,

[0556]

[0557] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.1 and I.2;

[0558] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.1 and I.3;

[0559] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.3 and I.4;

[0560] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.2 and I.4;

[0561] In another preferred embodiment, the compound of formula I is a compound of formula I.1;

[0562] In another preferred embodiment, the compound of formula I is a compound of formula I.2;

[0563] In another preferred embodiment, the compound of formula I is a compound of formula I.3;

[0564] In another preferred embodiment, the compound of formula I is a compound of formula I.4;

[0565] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae I.1 to I.4, wherein

[0566] B 1 Is N or CR B1 , B 2 It's CR B2 , and B 3 It's CR B3 ;

[0567] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0568] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl;

[0569] R 1 is H, halogen, C1-C6-alkyl or C3-C6-cycloalkyl;

[0570] R 2 is C1-C6-alkyl;

[0571] R 3 is H or C1-C6-alkyl;

[0572] R 4 is H or C1-C6-alkyl;

[0573] Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridinyl, which is unsubstituted or replaced by R Ar1 replace;

[0574] R Ar1is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and C3-C6-heterocyclyl moieties are unsubstituted or replaced by R f replace;

[0575] 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 ;

[0576] Ar 2 is phenyl, which is unsubstituted or replaced by R Ar2 replace;

[0577] R Ar2 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, wherein these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0578] or NR b R c ;

[0579] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0580] R d is H or C1-C6-alkyl;

[0581] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0582] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0583] m is 0, 1, or 2.

[0584] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae I.1 to I.4, wherein

[0585] 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;

[0586] R 1 is H, halogen, C1-C6-alkyl or C3-C6-cycloalkyl, preferably H or CH3;

[0587] R 2 is H or C1-C6-alkyl, preferably CH3;

[0588] B 1 Is N or CR B1 ;

[0589] B 2 Is N or CR B2 ;

[0590] B 3 Is N or CR B3 ;

[0591] B 4 It's CR B4 ;

[0592] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0593] R 3 is H or C1-C6-alkyl;

[0594] R 4 is H or C1-C6-alkyl;

[0595] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0596] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0597] In another preferred embodiment, the compound of formula I is selected from the compounds of formulae I.1 to I.4, wherein

[0598] 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;

[0599] R 1 is H or C1-C6-alkyl, preferably H or CH3;

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

[0601] B 1 Is N or CR B1 ;

[0602] B 2 Is N or CR B2 ;

[0603] B 3 Is N or CR B3 ;

[0604] B 4 It's CR B4 ;

[0605] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0606] R 3 is H or C1-C6-alkyl;

[0607] R 4 is H or C1-C6-alkyl;

[0608] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0609] Ar 2 Selected from Ar 2 -1 to Ar2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0610] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.1 and I.2, wherein

[0611] 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;

[0612] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0613] R 2 is H or C1-C6-alkyl, preferably CH3;

[0614] B 1 Is N or CR B1 ;

[0615] B 2 Is N or CR B2 ;

[0616] B 3 Is N or CR B3 ;

[0617] B 4 It's CR B4 ;

[0618] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

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

[0620] R 4 is H or C1-C6-alkyl;

[0621] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0622] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0623] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.1 and I.3, wherein

[0624] 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;

[0625] R 1 is H or C1-C6-alkyl, preferably H or CH3;

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

[0627] B 1 Is N or CR B1 ;

[0628] B 2 Is N or CR B2 ;

[0629] B 3 Is N or CR B3 ;

[0630] B 4 It's CR B4 ;

[0631] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0632] R 3 is H or C1-C6-alkyl;

[0633] R 4 is H or C1-C6-alkyl;

[0634] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0635] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0636] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.3 and I.4, wherein

[0637] 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;

[0638] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0639] R 2 is H or C1-C6-alkyl, preferably CH3;

[0640] B 1 Is N or CR B1 ;

[0641] B 2 Is N or CR B2 ;

[0642] B 3 Is N or CR B3 ;

[0643] B 4 It's CR B4 ;

[0644] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0645] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar1 -3;

[0646] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0647] In another preferred embodiment, the compound of formula I is selected from the compounds of formula I.2 and I.4, wherein

[0648] 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;

[0649] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0650] R 2 is H or C1-C6-alkyl, preferably CH3;

[0651] B 1 Is N or CR B1 ;

[0652] B 2 Is N or CR B2 ;

[0653] B 3 Is N or CR B3 ;

[0654] B 4 It's CR B4 ;

[0655] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0656] R 3 is H or C1-C6-alkyl;

[0657] R 4 is H or C1-C6-alkyl;

[0658] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0659] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0660] In another preferred embodiment, the compound of formula I is a compound of formula I.1, wherein

[0661] 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;

[0662] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0663] R 2 is H or C1-C6-alkyl, preferably CH3;

[0664] B 1 Is N or CR B1 ;

[0665] B 2 Is N or CR B2 ;

[0666] B 3 Is N or CR B3 ;

[0667] B 4 It's CR B4 ;

[0668] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0669] R 3 is H or C1-C6-alkyl;

[0670] R 4 is H or C1-C6-alkyl;

[0671] Ar1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0672] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0673] In another preferred embodiment, the compound of formula I is a compound of formula I.2, wherein

[0674] 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;

[0675] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0676] R 2 is H or C1-C6-alkyl, preferably CH3;

[0677] B 1 Is N or CR B1 ;

[0678] B 2 Is N or CR B2 ;

[0679] B 3 Is N or CR B3 ;

[0680] B 4 It's CR B4 ;

[0681] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0682] R 3 is H or C1-C6-alkyl;

[0683] R4 is H or C1-C6-alkyl;

[0684] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0685] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0686] In another preferred embodiment, the compound of formula I is a compound of formula I.3, wherein

[0687] B 1 Is N or CR B1 , B 2 It's CR B2 , and B 3 It's CR B3 ;

[0688] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0689] R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl;

[0690] R 1 is H, halogen, C1-C6-alkyl or C3-C6-cycloalkyl;

[0691] R 2 is C1-C6-alkyl;

[0692] Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridinyl, which is unsubstituted or replaced by R Ar1 replace;

[0693] R Ar1is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and C3-C6-heterocyclyl moieties are unsubstituted or replaced by R f replace;

[0694] NR b R c 、C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、-N=S(=O)-(C1-C6-

[0695] alkyl)2 or S(=O) m R e ;

[0696] Ar 2 is phenyl, which is unsubstituted or replaced by R Ar2 replace;

[0697] R Ar2 is halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, wherein these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0698] or NR b R c ;

[0699] R a 、R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen;

[0700] R d is H or C1-C6-alkyl;

[0701] R e is C1-C6-alkyl or C1-C6-haloalkyl;

[0702] R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen;

[0703] m is 0, 1, or 2.

[0704] In another preferred embodiment, the compound of formula I is a compound of formula I.3, wherein

[0705] 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;

[0706] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0707] R 2 is H or C1-C6-alkyl, preferably CH3;

[0708] B 1 Is N or CR B1 ;

[0709] B 2 Is N or CR B2 ;

[0710] B 3 Is N or CR B3 ;

[0711] B 4 It's CR B4 ;

[0712] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0713] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0714] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0715] In another preferred embodiment, the compound of formula I is a compound of formula I.4, wherein

[0716] 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;

[0717] R 1 is H or C1-C6-alkyl, preferably H or CH3;

[0718] R 2 is H or C1-C6-alkyl, preferably CH3;

[0719] B 1 Is N or CR B1 ;

[0720] B 2 Is N or CR B2 ;

[0721] B 3 Is N or CR B3 ;

[0722] B 4 It's CR B4 ;

[0723] R B1 、R B2 、R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen;

[0724] Ar 1 Selected from Ar 1 -1 to Ar 1 -17, preferably selected from Ar 1 -1 to Ar 1 -8, more preferably selected from Ar 1 -1 to Ar 1 -3;

[0725] Ar 2 Selected from Ar 2 -1 to Ar 2 -13, preferably selected from Ar 2 -1 to Ar 2 -3;

[0726] Particular compounds of formula I are the compounds of formulae I.1 to I.4 compiled in Tables 1 to 48 below, wherein the variable B of each compound of Tables 1 to 48 is 1 、B 2 、B 3 and B4 A combination of corresponds to each row of Table B. Each radical of the substituents mentioned in the table is furthermore on its own (independently of the combination in which it is mentioned) a particularly preferred aspect of the substituent in question.

[0727] Table 1. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[0728] Table 2. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[0729] Table 3. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[0730] Table 4. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[0731] Table 5. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[0732] Table 6. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar2 It is Ar 2 -2.

[0733] Table 7. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[0734] Table 8. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[0735] Table 9. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[0736] Table 10. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[0737] Table 11. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[0738] Table 12. Compounds of formula I.3, wherein R 1 It's H, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[0739] Table 13. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[0740] Table 14. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[0741] Table 15. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[0742] Table 16. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[0743] Table 17. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[0744] Table 18. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[0745] Table 19. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[0746] Table 20. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[0747] Table 21. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[0748] Table 22. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[0749] Table 23. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[0750] Table 24. Compounds of formula I.3, wherein R 1 It's H, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[0751] Table 25. Compounds of formula I.3, wherein R1 It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[0752] Table 26. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[0753] Table 27. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[0754] Table 28. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[0755] Table 29. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[0756] Table 30. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It's H, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[0757] Table 31. Compounds of formula I.3, wherein R 1 It is CH3, R 2It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[0758] Table 32. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[0759] Table 33. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[0760] Table 34. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[0761] Table 35. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[0762] Table 36. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It's H, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[0763] Table 37. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[0764] Table 38. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[0765] Table 39. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[0766] Table 40. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[0767] Table 41. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[0768] Table 42. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5 It is H, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[0769] Table 43. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5 is CH3, Ar1 It is Ar 1 -1,Ar 2 It is Ar 2 -1.

[0770] Table 44. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -1,Ar 2 It is Ar 2 -2.

[0771] Table 45. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -1.

[0772] Table 46. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -2,Ar 2 It is Ar 2 -2.

[0773] Table 47. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -1.

[0774] Table 48. Compounds of formula I.3, wherein R 1 It is CH3, R 2 It is CH3, R 5 is CH3, Ar 1 It is Ar 1 -3,Ar 2 It is Ar 2 -2.

[0775] Table B:

[0776]

[0777]

[0778]

[0779]

[0780]

[0781]

[0782]

[0783]

[0784]

[0785]

[0786]

[0787]

[0788]

[0789]

[0790]

[0791]

[0792]

[0793]

[0794]

[0795] Tables 49 to 96: include all compounds disclosed in Tables 1 to 48, respectively, wherein the compound of formula I.3 is replaced by a compound of formula I.4;

[0796] As used herein, the term "compounds of the present invention" or "compounds according to the present invention" refers to compounds of formula (I) as defined above, which are also referred to as "compounds of formula I" or "compound I" or "compounds of formula I", and include their salts, tautomers, stereoisomers and N-oxides.

[0797] The present invention also relates to mixtures of at least one compound according to the invention with at least one mixing partner as defined herein. Preferred are binary mixtures of a compound according to the invention as component I and a mixing partner as defined herein as component II. Preferred weight ratios for such binary mixtures are from 5000:1 to 1:5000, preferably from 1000:1 to 1:1000, more preferably from 100:1 to 1:100, and in particular from 10:1 to 1:10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I or an excess of component II may be used.

[0798] The mixing partners can be selected from the group consisting of pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers. Preferred mixing partners are insecticides, nematicides and fungicides.

[0799] 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 present invention can be used and with which a potential synergistic effect may occur is intended to illustrate possible combinations but does not impose any limitation:

[0800] M.1 Acetylcholinesterase (AChE) inhibitors: M.1A carbamates, such as aldicarb, benzylpyridinium carb, benfuracarb, butacarb, butacarb, carbaryl, carbofuran, butacarb, ethiofencarb, fenbutacarb, fenthiocarb, furamicarb, isoprocarb, methiocarb, methomyl, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, long-lasting carb, mixed carb, XMC, methomyl and triazolam; or M.1B organophosphates, such as acephate, methyl pyriphos, azinphos-ethyl, azinphos-methyl, cadusofos, chlorpyrifos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cypermethrin, demeton-S-methyl, diazinon, dichlorvos / DDVP, Dicrotophos, dimethoate, chlorpyrifos-methyl, disulfoton, EPN, ethion, chlorpyrifos, fenamiphos, fenitrothion, fenthion, thiamethoxam, heptenophos, cyanimiphos, isopropylamidophos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, chlorpyrifos, methamidophos, methidathion, mevinphos, monocrotophos, dibromophos, omethoate, sulfone, parathion, methyl parathion, fenthion, phorate, phosalone, phosmet, phosphamidon, phoxim, methyl pirimiphos, profenofos, methoprene, profenofos, pyraclofos, pyridazinphos, quinalphos, chlorpyrifos, butyl pirimiphos, temephos, terbufos, chlorpyrifos, disulfoton, triazophos, trichlorfon and aphidox;

[0801] M.2. GABA-gated chloride channel antagonists: M.2A cyclic diene organochloride compounds, such as endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), such as ethiprole, fipronil, butenefipronil, pyrafluprole, and pyriprole;

[0802] M.3 Sodium channel modulators from the M.3A pyrethroid class, for example, acralthrin, allethrin, D-cis-trans allethrin, D-trans allethrin, bifenthrin, k-bifenthrin, bio-allethrin, bio-allethrin S-cyclopentenyl, bio-resmethrin, cypermethrin, cyfluthrin, beta-cyfluthrin, flucythrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, phenothrin, deltamethrin , fenvalerate, esfenvalerate, etofenprox, cypermethrin, fenvalerate, flucythrin, flucythrin, t-fluvalinate, bromofluthrin, tefluthrin, mipromethrin, cyfluthrin, metofluthrin, methifluthrin, epsilon-metofluthrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrins (pyrethrum), pyrethrum, silafluthrin, tefluthrin, kappa-tefluthrin, tetrafluthrin, tetramethrin, tralomethrin, and transfluthrin; or an M.3B sodium channel modulator such as DDT or methoxychlor;

[0803] M.4 Nicotinic acetylcholine receptor agonists (nAChR): M.4A neonicotinoids, such as acetamiprid, clothianidin, cycloheximide, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or compound M.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-pentylideneaminoguanidine; 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 Flupyralidone; M.4E Trifluanidine, 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-phenolate, M.4E.1b)(3S)-3-(6-chloro-3-pyridyl)-8-methyl-5-oxo-6-phenyl-2,3-dihydrothiazol- [3,2-a]pyrimidin-8-ium-7-phenolate, M.4E.1c) (3S)-8-methyl-5-oxo-6-phenyl-3-pyrimidin-5-yl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-phenolate, M.4E.1d) (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-5-oxo-6-[3-(trifluoromethyl)phenyl]-2,3-dihydrothiazolo[3,2-a]pyrimidin-8 -ium-7-phenol salt; 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-phenol salt, 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-phenol salt;

[0804] M.5 Nicotinic acetylcholine receptor allosteric activators: spinosyns, such as spinosyn or spinosad;

[0805] M.6 Chloride channel activators from the avermectin and milbemycin classes, for example, abamectin, avermectin benzoate, ivermectin, lepidomectin or milbemycin;

[0806] M.7 Juvenile hormone mimetics, such as M.7A juvenile hormone analogs methoprene, methoprene and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;

[0807] M.8 Other nonspecific (multi-site) inhibitors, for example, M.8A alkyl halides such as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfonyl fluoride, M.8D borax, or M.8E tartar emetic;

[0808] M.9 chord organ TRPV channel modulators, such as M.9B pymetrozine; pyrimethoxazole;

[0809] M.10 Mite growth inhibitors, such as M.10A clofentezine, hexythiazox and fluazifop, or M.10B etoxazole;

[0810] M.11 Microbial disruptors of the insect midgut membrane, such as Bacillus thuringiensis or Bacillus sphaericus and the insecticidal proteins produced by them, such as Bacillus thuringiensis subsp. israelii, Bacillus sphaericus, Bacillus thuringiensis subsp. ayuzawa, Bacillus thuringiensis subsp. kurstaki and Bacillus thuringiensis subsp. simulans, or Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34 / 35Ab1;

[0811] M.12 Mitochondrial ATP synthase inhibitors, such as M.12A diafenthiuron, or M.12B organotin acaricides such as azoxatin, cyhexatin, or fenbutatin, M.12C propargite, or M.12D fenfothylsulfone;

[0812] M.13 Oxidative phosphorylation decouplers that interfere with the proton gradient, such as chlorfenapyr, DNOC, or sulfluramid;

[0813] M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, such as neristoxin analogs sulfamethoxazole, cartap, thiophanate-methyl, or dimethoate;

[0814] M.15 Chitin biosynthesis type 0 inhibitors, such as benzoylureas, for example, bistrifluan, chlorfluazuron, diflubenzuron, flufenoxuron, flufenoxuron, hexaflumuron, lufenuron, flufenoxuron, noviflumuron, teflubenzuron or triflumuron;

[0815] M.16 Chitin biosynthesis type 1 inhibitors, such as thiazolinone;

[0816] M.17 Molting disruptors, for Diptera insects, such as cyromazine;

[0817] M.18 Ecdysone receptor agonists such as dihydrazides, for example, methoxyfenozide, tebufenozide, chlorfenozide, furofenozide or chlorfenozide;

[0818] M.19 octopamine receptor agonists, such as amitraz;

[0819] M.20 Mitochondrial complex III electron transport inhibitors, such as M.20A hydrazone, M.20B acequinoxaline, M.20C pyrimidifen; or M.20D bifenazate;

[0820] M.21 Mitochondrial complex I electron transport inhibitors, for example M.21A METI acaricides and insecticides, such as fenazaquin, fenpyraclostrobin, pyrimidifen, pyridabenz, tebufenpyrad or tolfenpyrad, or M.21B rotenone;

[0821] M.22 Voltage-dependent 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;

[0822] M.23 Acetyl CoA carboxylase inhibitors, such as tetronic acid and tetramic acid derivatives, for example spirodiclofen, spiromesifen or spirotetramat; M.23.1 Metoclofen ethyl ester;

[0823] M.24 Mitochondrial complex IV electron transport inhibitors, for example, M.24A phosphines such as aluminum phosphide, calcium phosphide, phosphine, or zinc phosphide, or M.24B cyanide;

[0824] M.25 Mitochondrial complex II electron transport inhibitors, such as β-ketonitrile derivatives, for example, cyflumetofen or cyflumetofen;

[0825] M.28 A ryanodine receptor modulator from the class of diamides, such as flubendiamide, chlorantraniliprole, cyanantraniliprole, flutolanil, 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: cyclobenzamid, 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-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; or

[0826] M.28.6: Cyranofluanid; or

[0827] M.29: chordal organ modulators - undefined target sites, such as flonicamid;

[0828] M.UN. Insecticidal active compounds with an unknown or undefined mode of action, for example, acyclovir, afolan, azadirachtin, sulfamethoxam, benzyl methacrylate, bromofenapyr, bromopyralid, chlorpyrifos, cryolite, dichlorothiapyr, dicofol, flumethrin, flometoquin, fluthiazolin, fluhexafon, fluopyram, flurelana, metaldehyde, oxazolidinone, piperonyl butoxide, pyflubumide, pyridalyl, tioxazafen, 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,

[0829] M.UN.4: 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,

[0830] 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 based on Bacillus firmus (Votivo, I-1582);

[0831] M.UN.6: flupyrimin;

[0832] M.UN.8: trifluoroimidazole amide; M.UN.9.a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietane-3-yl)benzamide; M.UN.9.b): fluorooxazole amide; M.UN.10: 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole;

[0833] 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 amide; 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

[0834] 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-pyridinyl)thiazol-5-yl]pyridine-2-carboxamide; M.UN.12.e) N-Methylsulfonyl-6-[2-(3-pyridinyl)thiazol-5-yl]pyridine-2-carboxamide;

[0835] 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]pyridine-5-ol;

[0836] 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-N-pyridazin-4-yl-pyrazole-4-carboxamide; 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,

[0837] M.UN.17a) N-(1-methylethyl)-2-(3-pyridyl)-2H-indazole-4-carboxamide; M.UN.17b) N-cyclopropyl-2-(3-pyridyl)-2H-indazole-4-carboxamide; M.UN.17c) N-cyclohexyl-2-(3-pyridyl)-2H-indazole-4-carboxamide; M.UN.17d) 2-(3-pyridyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; M.UN.17e) 2-(3-pyridyl)-N-[(tetrahydro-2-furyl)methyl]-2H-indazole-5-carboxamide; M.UN.17f) methyl 2-[[2-(3-pyridyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; M.UN.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridyl)-2H-indazole-5-carboxamide; M.UN.17h) N-(2,2-difluoropropyl)-2-(3-pyridyl)-2H-indazole-5-carboxamide; M.UN.17i) 2-(3-pyridyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridyl)-2H-indazole-5-carboxamide,

[0838] M.UN.18. tyclopyrazoflor;

[0839] M.UN.19 sarolaner, M.UN.20 lotilaner;

[0840] 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-pyridinyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M.UN.22b 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridinyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine;

[0841] M.UN.23 isoxathiapiprolin;

[0842] 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 acynonapyr; M.UN.26 benzpyrimoxan; M.UN.27 tigolaner; M.UN.28 oxazolidinone;

[0843] 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-triazol-3-yl]phenyl]carbamate; M.UN.29b) [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl] N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; M.UN.29c) N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl] M.UN.29d) N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamic acid [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] ester; M.UN.29.e) (2Z)-3-(2-isopropylphenyl)-2-[(E )-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-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-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one;

[0844] 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 oxazolo[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-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]imidazo[4,5-b]pyridine 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.

[0845] Commercially available compounds of Group M listed above can be found in The Pesticide Manual, 17th edition, C. MacBean, British Crop Protection Council (2015), among other publications. The online Pesticide Manual is regularly updated and is available via http: / / bcpcdata.com / pesticide-manual.html.

[0846] Another online database of pesticides providing ISO common names is http: / / www.alanwood.net / pesticides.

[0847] M.4 cycloheximide is known from WO 2010 / 069266 and WO 2011 / 069456. M.4A.1 is known from CN 103814937, CN 105367557, and CN 105481839. M.4A.2 (pentafenidone) is known from WO 2013 / 003977, and M.4A.3 (approved as pyrimethamine in China) is known from WO 2007 / 101369. M.4E.1a) to M.4E.1f) are known from WO 2018177970. M.22B.1 is described in CN 10171577, and M.22B.2 is described in CN 102126994. M.23.1, ethyl methoxypiperidone, 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 US 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 a biocontrol agent based on Bacillus firmus is described in WO 2009 / 124707. Flufenacet 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. Brofenac and M.UN.11.b) to M.UN.11.h) are described in WO 2010 / 018714, and 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. 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.17j) are described in WO 2015 / 038503. M.UN.18 Tycloprazoflor is described in US 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. 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. Acynonapyr M.UN.25 is known from WO 2011 / 105506. Benzpyrimoxan M.UN.26 is known from WO 2016 / 104516. M.UN.27 is known from WO 2016 / 174049. Oxazosulfyl M.UN.28 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.

[0848] The following list of fungicides with which the compounds of the invention can be used is intended to illustrate possible combinations but does not limit them:

[0849] A) Respiratory depressants

[0850] -In Q oComplex III inhibitors of the site: azoxystrobin (A.1.1), carboxystrobin (A.1.2), syringostriatin (A.1.3), ethersoxim methyl (A.1.4), enestrobin (A.1.5), enestrobin (A.1.6), fenoxystrobin / flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), ethersoxim methyl (A.1.9), mandestrobin (A .1.10), fenoxystrobin (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), oxazolidinone (A.1.15), pyraclostrobin (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), pyrimidinecarb (A.1.19), pyraclostrobin (A.1.20), pyraclostrobin (A.1.21), pyraclostrobin (A.1.22), pyraclostrobin (A.1.23), pyraclostrobin (A.1.24), pyraclostrobin (A.1.25), pyraclostrobin (A.1.26), pyraclostrobin (A.1.27), pyraclostrobin (A.1.28), pyraclostrobin (A.1.29), pyraclostrobin (A.1.30), pyraclostrobin (A.1.31), pyraclostrobin (A.1.32), pyraclostrobin (A.1.33), pyraclostrobin (A.1.34), pyraclostrobin (A.1.35), pyraclostrobin (A.1.36), pyraclostrobin (A.1.37), pyraclostrobin (A.1.38), pyraclostrobin (A.1.39), pyraclostrobin (A.1.40), pyraclostrobin (A.1.41), pyraclostrobin 19), triclopyricarb / chlorodincarb (A.1.20), oxadiazolone (A.1.21), fenamidone (A.1.21), methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxymethyl]phenyl]-N-methoxy-carbamate (A.1.22), tetrazobactam (A.1.25), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazole-3 -yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), pyrimidifen (A.1.36), pyrifloxacin (A.1.37), 2-(o-((2,5-dimethylphenyl-oxymethylene)phenyl)-3-methoxy-acrylic acid methyl ester (A.1.38);

[0851] -In Q i Complex III inhibitors of the site: cyazofamid (A.2.1), indazolesulfamide (A.2.2), 2-methylpropionic acid [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] ester (A.2.3), fenpicoxamid (A.2.4), pyridoxamide (A.2.5);

[0852] - Complex II inhibitors: oxadixanil (A.3.1), benzovinflumizone (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), furamide (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluopyram (A.3.9), furazolidone (A.3.10), isopyram (A.3.11), pyraclostrobin (A.3.12), oxadixanil (A.3.13), oxycarboxin (A.3.14), fluopyram (A.3.15), penthiopyrad (A.3.16), fluorine Pyraclostrobin (A.3.17), diflubenzuron (A.3.18), fluazifop (A.3.19), chlorothalonil (A.3.20), thiophanate-methyl (A.3.21), indoppyrad (A.3.22), pyridinamide (A.3.23), flufenoxam (A.3.28), N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide (A.3.29), (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoic acid methyl ester (A.3.30), isopropyram (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-trimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(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);

[0853] - Other respiratory inhibitors: diflunisal (A.4.1); nitrophenyl derivatives: binapacryl (A.4.2), diflubenzuron (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), cypermethrin (A.4.6), pyraclostrobin (A.4.7); organometallic compounds: triphenyltin salts, such as triphenyltin acetate (A.4.8), triphenyltin chloride (A.4.9) or triphenyltin hydroxide (A.4.10); pyraclostrobin (A.4.11); silthiopyrad (A.4.12);

[0854] B) Sterol biosynthesis inhibitors (SBI fungicides)

[0855] -C14 demethylase inhibitors: triazoles: pentamethylenetetracycline (B.1.1), triaconazole (B.1.2), oxadiazole (B.1.3), cyproconazole (B.1.4), oxadiazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), fluoxepiconazole (B.1.8), nitrobenzene (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), amide azole (B.1.14), picofenazole (B.1.15), Metconazole (B.1.17), myclobutanil (B.1.18), oxamitazole (B.1.19), paclobutrazol (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), silyconazole (B.1.24), tebuconazole (B.1.25), fluconazole (B.1.26), triadimefon (B.1.27), triaflon (B.1.28), trichlorfon (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), ipfentrifluconazole (B.1.37), chlorfluanidazole (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), pyrimethanil (B.1.45), prochloraz (B.1.46), triflumuron (B.1.47); Pyrimidine, pyridine, piperazine: chlorfenapyr (B.1.49), pyrimethamine (B.1.50), triflate (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52);

[0856] -δ14-reductase inhibitors: 4-dodecyl-2,6-dimethylmorpholine (aldimorph) (B.2.1), doxepin (B.2.2), doxepin acetate (B.2.3), fenpropimorph (B.2.4), chlorfenapyr (B.2.5), fenpropidin (B.2.6), fenpropimorph (B.2.7), spiroxafil (B.2.8);

[0857] -3-Ketoreductase inhibitors: fenhexamid (B.3.1);

[0858] - Other sterol biosynthesis inhibitors: clofentoxime (B.4.1);

[0859] C) Nucleic acid synthesis inhibitors

[0860] - Phenylamide or acylamino acid fungicides: benalaxyl (C.1.1), benalaxyl-M (Benalaxyl-M) (C.1.2), kiralaxyl-M (Kiralaxyl) (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), furamide (C.1.6), oxadixyl (C.1.7);

[0861] - Other nucleic acid synthesis inhibitors: oxamexazole (C.2.1), octhiazolin (C.2.2), oxolinic acid (C.2.3), pyrimidine sulfonate (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);

[0862] D) Inhibitors of cell division and cytoskeleton

[0863] - Tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2), pyridachlometyl (D1.3), thiophanate (D.1.4), thiophanate-methyl (D.1.5), pyridachlometyl (D.1.6), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butyramide (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)butyramide (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-butyramide (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);

[0864] - Other cell division inhibitors: diethofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), mefentrazone (D.2.6), pyriofenone (D.2.7);

[0865] E) Amino acid and protein synthesis inhibitors

[0866] -Methionine synthesis inhibitors: cyprodinil (E.1.1), myclobutanil (E.1.2), pyrimethanil (E.1.3);

[0867] - Protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride hydrate (E.2.3), midonomycin (E.2.4), streptomycin (E.2.5), oxytetracycline (E.2.6);

[0868] F) Signal transduction inhibitors

[0869] -MAP / histidine kinase inhibitors: luoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);

[0870] -G protein inhibitor: quinoxyfen (F.2.1);

[0871] G) Lipid and membrane synthesis inhibitors

[0872] - Phospholipid biosynthesis inhibitors: Kewensan (G.1.1), Isopropylamine (G.1.2), Diflubenzuron (G.1.3), and Paclobutrazol (G.1.4);

[0873] -Lipid peroxidation: chloranilamine (G.2.1), pentachloronitrobenzene (G.2.2), tetrachloronitrobenzene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chlorpyrifos (G.2.6), chloramphenicol (G.2.7);

[0874] - Phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiafam (G.3.5), isoprenaline (G.3.6), valeron (G.3.7);

[0875] - Compounds and fatty acids that affect cell membrane permeability: propamocarb (G.4.1);

[0876] - Oxysterol binding protein inhibitors: fluoxapiprolin (G.5.1), fluoxapiprolin (G.5.3), 4-[1-[2-[3-difluoromethyl-5-methyl-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalene-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalene-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]- N-tetrahydronaphthalene-1-yl-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalene-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalene-1-yl-pyridine -2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalene-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalene-1-yl-pyridine-2-carboxamide (G.5.11);

[0877] H) Inhibitors with multi-site action

[0878] - 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);

[0879] -Thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metamidine (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), maneb (H.2.8), ziram (H.2.9);

[0880] -Organochlor compounds: difop-butyl (H.3.1), chlorothalonil (H.3.2), captol (H.3.3), captan (H.3.4), folpet (H.3.5), bacteriostatic (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorophenol (H.3.9) and its salts, tetrachlorophthalide (H.3.10), tolylfluanid (H.3.11);

[0881] -Guanidine and others: guanidine (H.4.1), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine acetate (H.4.5), guazatine octylamine (H.4.6), guazatine octylamine triacetate (H.4.7), guazatine trioctylbenzenesulfonate (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);

[0882] I) Cell wall synthesis inhibitors

[0883] - Glucan synthesis inhibitors: validamycin (I.1.1), polyoxin B (I.1.2);

[0884] -Melanin synthesis inhibitors: pyroquilonil (I.2.1), tricyclazole (I.2.2), cyproconazole (I.2.3), dicyclomet (I.2.4), blastamide (I.2.5);

[0885] J) Plant defense inducers

[0886] -Acibenzolar-S-methyl (J.1.1), thiabendazole (J.1.2), isotianil (J.1.3), thiazolamide (J.1.4), prohexadione-calcium (J.1.5); phosphonates: ethyl phosphonic acid (J.1.6), ethyl phosphine aluminum (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);

[0887] K) Unknown mode of action

[0888] -Bronnopol (K.1.1), miticide (K.1.2), cyfluanid (K.1.3), cymoxanil (K.1.4), dazomethanil (K.1.5), imidacloprid (K.1.6), dichlorocyanamide (K.1.7), dazomethanil (K.1.8), wild swallow quat (K.1.9), wild swallow quat-methyl sulfate (K.1.10), diphenylamine (K.1.11), seed coat ester (K.1.12), fenpyrad (K.1.13), flumetover (K.1.14), sulfamethoxam (K.1.15), fluthiazolinone (K.1.16), hypersensitive protein (K.1.17), sulfamethoxam (K.1.18), trichloromethylpyridine (K.1.1 9), phthalocyanine (K.1.20), tolprocarb (K.1.21), copper quinoline (K.1.22), propoxyquinoline (K.1.23), tebufloquin (K.1.24), phthalocyanine (K.1.25), pyraclostrobin (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) N.sub.1-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31), N.sub.1-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N.sub.1-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N.sub.1-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.34), N.sub.1-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine -3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilyl-propoxy)phenyl)-N-ethyl-N-methylformamidine (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide (K.1.36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyraclostrobin) (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), (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoic acid ethyl ester (K.1.40), tetrazole pyridine ester (K.1.41), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamic acid pentyl ester (K.1.42), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2- [pyridyl] carbamic acid but-3-ynyl ester (K.1.43), ipflufenoquin (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), dichlobentiazox (K.1.52), N'-(2,5-dimethyl-4-phenoxy-phenyl) N-ethyl-N-methyl-formamidine (K.1.53), pyrifenamine (K.1.54).

[0889] The fungicides described by the generic names, their preparation and their activity, for example against harmful fungi, are known (cf.: http: / / www.alanwood.net / pesticides / ); these substances are commercially available.

[0890] The active substances designated as component 2, their preparation and their activity, for example, against harmful fungi are known (cf.: http: / / www.alanwood.net / pesticides / ); these substances are commercially available. The compounds described by IUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. [Canadian Journal of Plant Science] 48 (6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002 316 902; DE 19650197; DE 10021412; DE 102005009458;US3,296,272;US 3,325,503;WO 98 / 46608;WO 99 / 14187;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 03 / 11853; WO 03 / 14103; WO 03 / 16286; WO 03 / 53145; WO 03 / 61388; WO 03 / 66609;WO 03 / 74491; WO 04 / 49804; WO 04 / 83193; WO 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, WO 13 / 127704, WO 13 / 024009, WO 13 / 24010, WO 13 / 047441, WO 13 / 162072, WO 13 / 092224, WO 11 / 135833, CN 1907024, CN1456054, CN 103387541, CN 1309897, WO 12 / 84812, CN 1907024,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, WO 13 / 47441). Some compounds are identified by their CAS registry number, which is divided into three parts by a hyphen, the first part consisting of two to seven digits, the second part consisting of two digits, and the third part consisting of a single digit. ;

[0891] Biopesticides

[0892] Suitable admixture partners of the compounds of the present invention also include biopesticides.

[0893] Biopesticides are defined as pesticides based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or in the form of natural products (compounds such as metabolites, proteins, or extracts from organisms or other natural sources) (US Environmental Protection Agency: http: / / www.epa.gov / pesticides / biopesticides / ). Biopesticides fall into two main categories, microbial and biochemical pesticides:

[0894] (1) Microbial pesticides are composed of bacteria, fungi, or viruses (and often include metabolites produced by bacteria and fungi). Entomopathogenic nematodes are also classified as microbial pesticides, although they are multicellular.

[0895] (2) Biochemical pesticides are naturally occurring substances or substances that are structurally similar and functionally equivalent to naturally occurring substances and extracts from biological sources that control pests or provide other crop protection uses as defined below, but have a non-toxic mode of action (such as growth or development regulation, attractant, repellent or defense activator (e.g., induced resistance) and are relatively non-toxic to mammals.

[0896] Biopesticides for combating crop diseases have been proven across a wide range of crops. For example, biopesticides have played an important role in controlling downy mildew. Their benefits include a zero-day pre-harvest interval, the ability to use during periods of moderate to severe disease pressure, and the ability to mix or rotate with other registered pesticides.

[0897] The main growth areas for biopesticides are seed treatment and soil improvement. For example, biopesticide seed treatments are used to control soil-borne fungal pathogens that cause seed rot, damping-off, root rot, and seedling blight. They can also be used to control fungal pathogens that are transmitted within seeds as well as those that live on the surface of seeds. Many biopesticide products have also demonstrated the ability to stimulate plant host defenses and other physiological processes, which can make treated crops more resistant to various biotic and abiotic stresses or regulate plant growth. Many biopesticide products have also demonstrated the ability to stimulate plant health, plant growth, and / or yield-enhancing activity.

[0898] The following list of biopesticides with which the compounds of the invention can be used in combination is intended to illustrate possible combinations but does not limit them:

[0899] L) Biopesticides

[0900] L1) Microbial pesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activity: Parasiticidal spores, Aspergillus flavus, Aureobasidium brevis, Bacillus spp., Bacillus amyloliquefaciens, Bacillus amyloliquefaciens plantarum (also known as Bacillus velez), Bacillus megaterium, Bacillus mohaievii, Bacillus mycoides, Bacillus pumilus, Bacillus simplex, Bacillus haloterreus, Bacillus subtilis, Bacillus subtilis var. amyloliquefaciens, Bacillus velez, Candida oleifera, Candida saitoana, Clavibactermichiganensis (bacteriophage), Cleometheus spp., Cryptococcus parasiticus, Cryptococcus albus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea. catenulate (also known as Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticum, Lysobacter mold-producing, Mycobacterium drupe, Microdochium dimerum, Sphaeroides microsporum, Muscodor albus, Bacillus alveoli, Paenibacillus epiphyticus, Paenibacillus polymyxa, Pantoea agglomerans, Penicillium bilaireae, Pseudomonas species, Pseudomonas viridis, Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces glaucum, Streptomyces lydicus, Streptomyces violaceus, Streptomyces leucoderma, Trichoderma spp. asperelloides), Trichoderma acanthophorum, Trichoderma amurensis, Trichoderma apical, Trichoderma gaimsii, Trichoderma harmatum, Trichoderma harzianum, Trichoderma polysporum, Trichoderma stromaticum, Trichoderma virens, Trichoderma viride, Typhula phacorrhiza, Typhula serrata, Verticillium dahliae, and zucchini yellow mosaic virus (avirulent strain);

[0901] L2) Biochemical pesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activity: hypersensitive proteins, Knotweed extracts;

[0902] L3) Microbial pesticides with insecticide, acaricide, snailicide and / or nematocidal activity: Agrobacterium radiobacterium, Bacillus cereus, Bacillus firmus, Bacillus thuringiensis, Bacillus thuringiensis subsp. ayuzawa, Bacillus thuringiensis subsp. israelii, Bacillus thuringiensis subsp. mellonella, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. simulans, Beauveria bassiana, Beauveria brucei, Burkholderia species, active purple bacteria (Chromobacterium subtsugae), codling moth granulovirus (CpGV), pseudo codling moth granulovirus (CrleGV), Flavobacterium species, cotton bollworm nuclear polyhedrosis virus (HearNPV), zea armyworm nuclear polyhedrosis virus (HzNPV), zea armyworm single capsid nuclear polyhedrosis virus (HzSNPV), bacteriotrophic Heterorhabditis elegans, Coryneformis fumosorum, Lecanicillium longisporum longisporum), L. muscarium, Metarhizium anisopliae, Metarhizium anisopliae microspore var., Metarhizium anisopliae locust var., Nomura leishmanii, Paecilomyces fumosoroseus, Paecilomyces lilacinus, Paenibacillus japonicus, Pasteurella species, Pasteurella szabalais, Pasteurella penetrantis, Pasteurella ramosa, Pasteurella listeri, Pasteurella usgae, Pseudomonas fluorescens, Spodoptera nuclei nuclear polyhedrosis virus (SpliNPV), Steinmerella scutellariae, Steinmera scutellariae, Sawfly nematode, Streptomyces scincidioides, Streptomyces tenuiflorus;

[0903] L4) Biochemical pesticides with 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-decadienoic acid ethyl ester (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavandulyl senecioate, cis-jasmone, 2-methyl-1-butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-acetic acid -2,13-octadecadien-1-ol ester, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, termite pheromone (pentatermanone), (E,Z,Z)-3,8,11-tetradecadien-1-yl 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, Quillay extract;

[0904] L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity: Azospirillum agalactiae, Azospirillum brasiliensis, Azospirillum lipogenicum, Azospirillum iraqium, Azospirillum euryhaline, Bradyrhizobium sp., Bradyrhizobium elsdenii, Bradyrhizobium glycines, Bradyrhizobium liaoningensis, Bradyrhizobium lupini, Delftia acidovorans, arbuscular mycorrhizal fungi, Mesorhizobium sp., Rhizobium leguminosarum biotype bean, Rhizobium leguminosarum biotype trifolium, Rhizobium leguminosarum biotype faba bean, Rhizobium tropicalis, and Sinorhizobium meliloti.

[0905] The biopesticides from groups L1) and / or L2) may also have insecticide, acaricide, snailicide, pheromone, nematocidal, plant stress-reducing, plant growth regulator, plant growth promoting, and / or yield-enhancing activity. The biopesticides from groups L3) and / or L4) may also have fungicidal, bactericidal, virucidal, plant defense activator, plant stress-reducing, plant growth regulator, plant growth promoting, and / or yield-enhancing activity. The biopesticides from group L5) may also have fungicidal, bactericidal, virucidal, plant defense activator, insecticide, acaricide, snailicide, pheromone, and / or nematocidal activity.

[0906] Many of these biopesticides are deposited under the accession numbers mentioned herein (prefixes such as ATCC or DSM refer to the abbreviations of the corresponding culture deposits, for details see, for example: http: / / www.wfcc.info / ccinfo / collection / by_acronym / ), mentioned in the literature, registered and / or commercially available: A mixture of Aureobasidium pullulans DSM 14940 and DSM 14941 isolated in Konstanz, Germany in 1989 (e.g. blastospores from bio-ferm GmbH, Austria) ), Azospirillum brasiliensis Sp245 was originally isolated in the wheat fields of southern Brazil (Passo Fonto) at least before 1980 (BR 11005; e.g., from BASF Agricultural Specialties Ltd., Brazil). Gramíneas), Azospirillum brasiliensis strains Ab-V5 and Ab-V6 (e.g., AzoMax from Novozymes BioAg Produtos papraAgricultura Ltda. in Cuatrobaras, Brazil or Simbiose- Plant Soil 331, 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; US ​​8,445,255); Bacillus amyloliquefaciens subsp. plantarum strain, formerly sometimes also called Bacillus subtilis, recently classified as Bacillus velezensis together with B. methylotrophicus and Bacillus velezensis (Int. J. Syst. Evol. Microbiol. [International Journal of Systematic and Evolutionary Microbiology] 66, 1212-1217, 2016); Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis D747 isolated from air in Kikukawa, Japan (US20130236522A1; FERM BP-8234; Double Nickel from Certis LLC, USA TM 55 WDG), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis FZB24 (also known as SB3615; DSM 96-2; J. Plant Dis. Prot. 105, 181-197, 1998; for example, from Novozyme Biologicals, Inc., USA) isolated from soil in Brandenburg, Germany. ), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis FZB42 isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. [Journal of Plant Diseases and Control] 105, 181-197, 1998; for example Rhizobacterium from AbiTEP GmbH, Germany 42), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis MBI600 (also known as 1430; NRRL B-50595; US2012 / 0149571A1; for example from BASF Corporation, USA) isolated from broad beans at Sutton Bonington, Nottinghamshire, UK, at least before 1988. ), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velez QST-713 (NRRL B-21661 isolated from a peach orchard in California, USA in 1995; for example, MAX), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velez TJ1000 isolated in South Dakota, USA in 1992 (also known as 1BE; ATCC BAA-390; CA 2471555 A1; QuickRoots from TJ Technologies, Watertown, South Dakota, USA TM ); Bacillus firmus CNCM 1-1582, a variant of the parent strain EIP-N1 isolated from soil in the central plains of Israel (CNCM 1-1556) (WO 2009 / 126473, US 6,406,690; for example, from Bayer CropScience LP, USA ), Bacillus pumilus GHA 180 was isolated from the rhizosphere of apple trees in Mexico (IDAC 260707-01; for example, PRO- Bacillus pumilus INR-7, also known as BU-F22 and BU-F33, was isolated from cucumbers infected with Erwinia tracheiphila at least until 1993 (NRRL B-50185, NRRL B-50153; US 8,445,255), Bacillus pumilus KFP9F was isolated from grass rhizospheres in South Africa at least until 2008 (NRRL B-50754; WO 2014 / 029697; e.g., BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bacillus pumilus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia in 1998 (NRRL B-30087; for example from Bayer CropScience USA or Plus), Bacillus simplex ABU 288 (NRRL B-50304; US 8,445,255), Bacillus subtilis FB17, also known as UD 1022 or UD10-22, was isolated from red beetroot in North America (ATCC PTA-11857; System. Appl. Microbiol. [System and Applied Microbiology] 27, 372-379, 2004; US2010 / 0260735; WO 2011 / 109395); Bacillus thuringiensis subsp. ayuzawa ABTS-1857 was isolated in 1987 from soil taken from a lawn in Ephraim, Wisconsin, USA (also known as ABG-6346; ATCC SD-1372; e.g., from BioFa AG, Münsingen, Germany). ), Bacillus thuringiensis subsp. Kurstaki ABTS-351 is equivalent to HD-1 isolated in 1967 from diseased black larvae of pink bollworm in Brownsville, Texas, USA (ATCC SD-1275; e.g., from Valent BioSciences, IL, USA DF), Bacillus thuringiensis subsp. kurstaki SB4 was isolated from the corpses of African stem borer (E. saccharina) larvae (NRRLB-50753; for example, Beta ), Bacillus thuringiensis subsp. pseudogalea NB-176-1, a mutant of strain NB-125, a wild-type strain isolated in 1982 from dead pupae of the beetle Tenebrio molitor (DSM 5480; EP 585 215 B1; e.g., from Valent BioSciences, Switzerland ), Beauveria bassiana GHA (ATCC 74250; for example, from Laverlam Int. Corp., USA 22WGP), Beauveria bassiana JW-1 (ATCC 74040; e.g., from CBC (Europe) Srl, Italy ), Beauveria bassiana PPRI 5339 was isolated from the larvae of the tortoise beetle Conchylocteniapunctata (NRRL 50757; for example, from BASF Agricultural Specialities (Pty) Ltd., South Africa). ), B. elsdenii strain SEMIA 5019 (also known as 29W) was isolated in Rio de Janeiro, Brazil, and SEMIA 587 was isolated in 1967 in the State of Rio Grande do Sul, from areas previously inoculated with North American isolates and used as commercial inoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g., GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), and B. sojae 532c was isolated from the field in Wisconsin, USA (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e.g., from BASF Agricultural Specialties Ltd., Canada). Super), a variant of the soybean bradyrhizobium E-109 of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 2011); a soybean bradyrhizobium strain known from Appl. Environ. Microbiol. 73(8), 2635, 2007 deposited in SEMIA: SEMIA 5079 was isolated from soil in Embrapa-Cerrados, Cerrados, Brazil, and has been used as a commercial inoculum since 1992 (CPAC 15; e.g., GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil), soybean bradyrhizobium SEMIA 5080 was obtained under laboratory conditions in Embrapa-Cerrados, Brazil and has been used as a commercial inoculant since 1992. It is a natural variant (CB1809) of SEMIA 586 originally isolated in the United States (CPAC7; for example, GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia species A396 was isolated from soil in Nikko, Japan in 2008 (NRRL B-50319; WO 2013 / 032693; Marrone BioInnovations, Inc., USA), and Conchoderma CON / M / 91-08 was isolated from oilseed rape (WO 1996 / 021358; DSM 9660; for example, from Bayer CropScience AG, Germany). WG, WG), hypersensitive protein (α-β) protein (Science 257, 85-88, 1992; for example, Messenger from Plant Health Care plc, UK TM or HARP-N-Tek), cotton bollworm nuclear polyhedrosis virus (HearNPV) (J. Invertebrate Pathol [Journal of Invertebrate Pathology]. 107, 112-126, 2011; for example, from Adermatt Biocontrol, Switzerland From Koppert, Brazil AgBiTech Pty Ltd. from Queensland, Australia Max), Spodoptera frugiperda single capsid nuclear polyhedrosis virus (HzSNPV) (e.g., from Certis LLC, USA) ), Spodoptera frugiperda nuclear polyhedrosis virus ABA-NPV-U (e.g., from AgBiTech Pty Ltd., Queensland, Australia) ), bacteriotrophic Heterorhabditis elegans (e.g., from BASF Agricultural Specialities Limited, UK) G), Apopka-97 was isolated from mealybugs on Gynura purpurogenum in Apopka, Florida, USA (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761, 2012; for example, PFR-97 from Certis LLC, USA TM or ), Metarhizium anisopliae microsporum variant F52, also known as 275 or V275, was isolated from Codling moth in Austria (DSM 3884, ATCC 90448; e.g. Novozymes Biologicals BioAg Group, Canada), drupe metschnikowia 277 was isolated from grapes in central Israel (US 6,994,849; NRRL Y-30752; for example, the previous ), Paecilomyces lilacinus 251 was isolated from infected nematode eggs in the Philippines (AGAL 89 / 030550; WO 1991 / 02051; Crop Protection 27, 352-361, 2008; for example from Bayer CropScience AG, Germany and Certis from the United States ), Bacillus alvei NAS6G6 was isolated from the rhizosphere of grasses in South Africa at least before 2008 (WO 2014 / 029697; NRRL B-50755; for example, BAC-UP from BASF Agricultural Specialities (Pty) Ltd. in South Africa), Paenibacillus strains isolated from soil samples in various European regions including Germany: Paenibacillus epiphyticus Lu17015 (WO 2016 / 020371; DSM 26971), Paenibacillus polymyxa plantarum Lu16774 (WO 2016 / 020371; DSM 26969), Paenibacillus polymyxa plantarum Lu17007 (WO 2016 / 020371; DSM 26970); Pasteurella szewiczae Pn1 was isolated from soybean fields in Illinois, USA in the mid-2000s (ATCC SD-5833; Federal Register 76(22), 5808, February 2, 2011; for example, Clariva TM PN), Penicillium bilaii (also known as P. bilaii) strains ATCC 18309 (= ATCC 74319), ATCC 20851 and / or ATCC 22348 (= ATCC 74318) were originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1), 91-102, 1998; US 5,026,417, WO 1995 / 017806; e.g., Jump Start, Novozymes Biologicals BioAg Group, Canada). ), Rhizoma Polygoni Cuspidatum Extract (EP 0307510 B1; for example from Marrone BioInnovations, Davis, CA, USA) SC or BioFa AG from Germany ), Steinberg's nematode (e.g., from BASF Agricultural Specialities Limited, UK). ), Spodoptera steheni (e.g., from BioWorks, Inc., USA From BASF Agricultural Specialities Limited, UK ), Streptomyces tenuifolius NRRL B-50550 (WO 2014 / 124369; Bayer CropScience, Germany), Trichoderma acanthosporum JM41R isolated in South Africa (NRRL 50759; also known as Trichoderma acrosporum; e.g., from BASF Agricultural Specialities (Pty) Ltd., South Africa) ), Trichoderma harzianum T-22 also known as KRL-AG2 (ATCC 20847; BioControl [Biological Control] 57, 687-696, 2012; e.g., from BioWorks Inc., USA or SabrEx from Advanced Biological Marketing Inc., Van Wert, Ohio, USA TM ).

[0907] According to the present invention, the solid material (dry matter) of the biopesticide (except oils such as neem oil etc.) is considered to be the active ingredient (eg obtained after drying or evaporation of the extraction or suspension medium in the case of liquid formulations of microbial pesticides).

[0908] According to the present invention, the weight ratios and percentages used herein for biological extracts such as Quillaja saponaria extract are based on the total weight of the dry content (solid material) of the respective extracts.

[0909] The total weight ratio of a composition comprising at least one microbial pesticide in the form of viable microbial cells (including dormant forms) can be determined by using the amount of CFU of the corresponding microorganism to calculate the total weight of the corresponding active ingredient using the following equation: 1 x 10 10 A CFU is equal to the total weight of one gram of the corresponding active ingredient. A colony-forming unit (CFU) is a measure of viable microbial cells, particularly fungal and bacterial cells. Furthermore, in the case of (entomopathogenic) nematode biopesticides, such as the nematode Spodoptera carinii, the term "CFU" can also be understood as referring to the number of (juvenile) individual nematodes.

[0910] When mixtures comprising microbial pesticides are used for crop protection, the application rate range is preferably about 1×10 6 Up to 5x 10 15 (or greater) CFU / ha, preferably about 1 x 10 8 to about 1x 10 13 CFU / ha, and even more preferably about 1 x 10 9 to about 1x 10 12In the case of (entomopathogenic) nematodes as microbial pesticides (e.g. Spodoptera carinii nematode), the application rate range is preferably about 1 x 10 5 to 1x 10 12 (or larger), more preferably 1x 10 8 to 1x 10 11 , even more preferably 5x 10 8 to 1x 10 10 Individuals (e.g. in the form of eggs, larvae or any other living stage, preferably in the infetive larval stage) / ha.

[0911] When mixtures comprising microbial pesticides are used for seed treatment, the application rate range for plant propagation material is preferably about 1 x 10 6 to 1x 10 12 (or greater) CFU / seed. Preferably, the concentration is about 1 x 10 6 to about 1x10 9 CFU / seed. In the case of microbial pesticides II, the application rate range for plant propagation materials is also preferably about 1 x 10 7 to 1x 10 14 (or greater) CFU / 100kg seeds, preferably 1x 10 9 to about 1x 10 12 CFU / 100kg seeds.

[0912] The invention furthermore relates to agrochemical compositions comprising an adjuvant and at least one compound according to the invention or a mixture thereof.

[0913] The agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof. The term "pesticidally effective amount" is defined below.

[0914] The compounds of the present invention or mixtures thereof can be converted into conventional types of agrochemical compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, compressed tablets, capsules, and mixtures thereof. Examples of composition types are suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, pastilles, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), molded articles (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticide preparations (e.g., LN), and gel formulations for treating plant propagation materials such as seeds (e.g., GF). These and additional composition types are defined in "Catalogue of pesticide formulation types and international coding system", Technical Monograph - Issue 2, 6th Edition, May 2008, CropLife International.

[0915] These compositions are prepared in a known manner, as described by 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.

[0916] Examples of suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, binders, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, tackifiers and adhesives.

[0917] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling point mineral oil fractions, for example kerosene, diesel; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, for example toluene, paraffin, tetralin, alkylated naphthalenes; alcohols, for example ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example cyclohexanone; esters, for example lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, for example N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[0918] Suitable solid carriers or fillers are mineral earths, for example silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, for example cellulose, starch; fertilizers, for example ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin, for example cereal flour, bark flour, wood flour, nut shell flour and mixtures thereof.

[0919] 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, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International or North American Edition).

[0920] Suitable anionic surfactants are alkali metal salts, alkaline earth metal salts or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. The example of sulfonates is alkyl aryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, fatty acids and oily sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalene sulfonates, dodecyl- and tridecylbenzene sulfonates, naphthalene and alkylnaphthalene sulfonates, sulfosuccinates or sulfosuccinamates. The example of sulfate is the sulfate of fatty acids and oily sulfate, ethoxylated alkylphenol sulfate, alcohol sulfate, ethoxylated alcohol sulfate or the sulfate of fatty acid ester. The example of phosphate is phosphoric ester. The example of carboxylates is alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.

[0921] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide can be used for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerides, or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose, and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinyl pyrrolidone, vinyl alcohol, or vinyl acetate.

[0922] Suitable cationic surfactants are quaternary ammonium surfactants, for example, quaternary ammonium compounds with one or two hydrophobic groups or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers comprising a block of polyethylene oxide and polypropylene oxide, or ABC type block polymers comprising an alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybasics. The example of a polyacid is an alkali metal salt of polyacrylic acid or a polyacid comb polymer. The example of a polybasic base is polyvinylamine or polyvinylamine.

[0923] Suitable adjuvants are compounds that themselves have negligible or even no pesticidal activity and that improve the biological performance of the compounds of the invention against the target. Examples are surfactants, mineral or vegetable oils, and other adjuvants. Further examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

[0924] Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[0925] Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones.

[0926] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol.

[0927] Suitable defoamers are silicones, long-chain alcohols, and salts of fatty acids.

[0928] Suitable colorants (e.g. red, blue or green) are pigments with low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin colorants, azo colorants and phthalocyanine colorants).

[0929] Suitable tackifiers or adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0930] Examples of composition types and their preparation are:

[0931] i) Water-soluble concentrates (SL, LS)

[0932] 10% to 60% by weight of a compound I according to the invention and 5% to 15% by weight of a wetting agent (eg alcohol alkoxylate) are dissolved in water and / or a water-miscible solvent (eg alcohol) admixed to 100% by weight. The active substance dissolves on dilution with water.

[0933] ii) Dispersible Concentrates (DC)

[0934] 5 wt% to 25 wt% of the compound I according to the present invention and 1 wt% to 10 wt% of a dispersant (eg polyvinyl pyrrolidone) are dissolved in an organic solvent (eg cyclohexanone) added to 100 wt%, and diluted with water to obtain a dispersion.

[0935] iii) Emulsifiable concentrates (EC)

[0936] 15-70 wt% of the compound I according to the present invention and 5-10 wt% of an emulsifier (such as calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (such as aromatic hydrocarbon) added to 100 wt%, and diluted with water to obtain an emulsion.

[0937] iv) Emulsion (EW, EO, ES)

[0938] 5-40 wt% of Compound I according to the present invention and 1-10 wt% of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon). This mixture is then added to 100 wt% of water using an emulsifier to form a uniform emulsion. The mixture is then diluted with water to obtain an emulsion.

[0939] v) Suspension (SC, OD, FS)

[0940] In a stirred ball mill, 20-60 wt% of the compound I according to the invention are ground with addition of 2-10 wt% of a dispersant and wetting agent (e.g., sodium ligninsulfonate and alcohol ethoxylate), 0.1-2 wt% of a thickener (e.g., xanthan gum), and up to 100 wt% of water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS compositions, up to 40 wt% of a binder (e.g., polyvinyl alcohol) is added.

[0941] vi) Water-dispersible granules and water-soluble granules (WG, SG)

[0942] 50% to 80% by weight of the compound I according to the invention are finely ground with up to 100% by weight of dispersants and wetting agents (e.g. sodium ligninsulfonate and alcohol ethoxylate) and prepared into water-dispersible or water-soluble granules using industrial equipment (e.g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

[0943] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0944] 50-80 wt% of the compound I according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% of a dispersant (e.g., sodium lignosulfonate), 1-3 wt% of a wetting agent (e.g., alcohol ethoxylate), and up to 100 wt% of a solid carrier (e.g., silica gel). Dilution with water gives a stable dispersion or solution of the active substance.

[0945] viii) Gel (GW, GF)

[0946] In a stirred ball mill, 5-25 wt% of the compound I according to the invention are comminuted with addition of 3-10 wt% of a dispersant (e.g. sodium ligninsulfonate), 1-5 wt% of a thickener (e.g. carboxymethylcellulose) and up to 100 wt% of water to give a fine active substance suspension. Dilution with water gives a stable active substance suspension.

[0947] ix) Microemulsion (ME)

[0948] 5-20 wt% of a compound I according to the invention is added to 5-30 wt% of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10-25 wt% of a surfactant blend (e.g., alcohol ethoxylate and arylphenol ethoxylate), and 100 wt% of water. This mixture is stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[0949] x) Microcapsules (CS)

[0950] An oil phase containing 5-50 wt% of Compound I according to the present invention, 0-40 wt% of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon), and 2-15 wt% of acrylic monomers (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylates) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Free radical polymerization initiated by a free radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5-50 wt% of Compound I according to the present invention, 0-40 wt% of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethylene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer amount is 1-10 wt%. The wt% is relative to the total CS composition.

[0951] xi) Dustable powders (DP, DS)

[0952] 1% to 10% by weight of a compound I according to the invention are finely ground and intimately mixed with up to 100% by weight of a solid carrier (eg finely divided kaolin).

[0953] xii) Granules (GR, FG)

[0954] 0.5 wt% to 30 wt% of a compound I according to the invention is finely ground and associated with a solid carrier (eg silicate) added to 100 wt%. Granulation is achieved by extrusion, spray drying or fluid bed.

[0955] xiii) Ultra Low Volume Liquids (UL)

[0956] 1 wt% to 50 wt% of the compound I according to the present invention is dissolved in an organic solvent (eg aromatic hydrocarbon) added to 100 wt%.

[0957] The compositions of types i) to xi) may optionally contain further adjuvants, such as 0.1-1 wt% bactericide, 5-15 wt% antifreeze, 0.1-1 wt% antifoam and 0.1-1 wt% colorant.

[0958] Agrochemical compositions generally contain between 0.01% and 95% by weight, preferably between 0.1% and 90%, most preferably between 0.5% and 75% by weight of active substance. The active substance is employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to the NMR spectrum).

[0959] Various types of oils, wetting agents, adjuvants, fertilizers, or micronutrients and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the active substances or compositions containing them as a premix or, if appropriate, not until just before use (tank mix). These agents can be admixed with the composition according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0960] The user usually applies the composition according to the present invention by a pre-dosing device, a backpack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up to the desired application concentration with water, a buffer, and / or another adjuvant, and thus obtains a ready-to-use spray liquid or agrochemical composition according to the present invention. Usually, 20 to 2000 liters, preferably 50 to 400 liters of ready-to-use spray liquid are applied per hectare of agricultural usable area.

[0961] According to one embodiment, the individual components of the composition according to the invention (eg parts of a kit or parts of a binary or ternary mixture) can be mixed by the user himself in a spray tank and, if appropriate, further auxiliaries can be added.

[0962] In another embodiment, the user can mix the individual components or partially premixed components of the composition according to the invention, for example the components comprising the compound of the invention and / or the mixing partners as defined above, in a spray tank and, if appropriate, add further auxiliaries and additives.

[0963] In another embodiment, the individual components or partially premixed components of the composition according to the invention, e.g., components comprising a compound of the invention and / or a mixing partner as defined above, may be applied jointly (e.g., after tank mixing) or sequentially.

[0964] The compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials (such as seeds), or soil or water in which plants are growing from attack or infection by animal pests. Therefore, the present invention also relates to a method for plant protection, which method comprises contacting crops, plants, plant propagation materials such as seeds, or soil or water in which plants are growing to be protected from attack or infection by animal pests with a pesticidal effective amount of a compound of the present invention.

[0965] The compounds of the present invention are also suitable for use in resisting or controlling animal pests. Therefore, the invention still further relates to methods for resisting or controlling animal pests, the method comprising contacting the animal pests, their habitats, breeding grounds or food supplies, or crops, plants, plant propagation materials such as seeds or animal pests with soil or regions, materials or environments in which they are growing or may grow with a pesticidal effective dose.

[0966] The compounds of the present invention are effective both by contact and by ingestion. In addition, the compounds of the present invention may be applied to any and all developmental stages, such as eggs, larvae, pupae, and adults.

[0967] As defined above, the compounds of the invention can be applied as such or in the form of a composition comprising them. In addition, the compounds of the invention can be applied together with a mixed partner as defined above, or in the form of a composition comprising said mixture as defined above. The components of said mixture can be applied simultaneously, jointly or individually, or in succession, i.e. one after the other, so as to produce a mixture "in situ" at the desired location (e.g., a plant); in the case of individual application, this generally does not have any influence on the outcome of the control measure.

[0968] Application can be carried out both before and after infestation of crops, plants, plant propagation material (such as seeds), soil or the area, material or the environment by the pest.

[0969] Suitable application methods include, in particular, soil treatment, seed treatment, in-furrow application, and foliar application. Soil treatment methods include irrigating the soil, drip irrigation (drip irrigation applied to the soil), soaking roots, tubers, or bulbs, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. In furrow application, the steps typically include: digging a furrow in the arable land, sowing the furrow with seeds, applying the pesticidal active compound to the furrow, and closing the furrow. Foliar application refers to applying the pesticidal active compound to the leaves of the plant, for example, by means of a spray device. For foliar application, it may be advantageous to modify the behavior of the pest by combining pheromones with the compounds of the present invention. Suitable pheromones for specific crops and pests are known to those skilled in the art and are publicly available from databases of pheromones and semiochemicals, such as http: / / www.pherobase.com.

[0970] As used herein, the term "contacting" includes direct contact (applying the compound / composition directly to 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 in which the pest is growing or may grow).

[0971] 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 referred to as crop insect pests.

[0972] The term "crop" refers to both growing crops and harvested crops.

[0973] The term "plant" includes cereals such as durum wheat and other wheats, rye, barley, triticale, oats, rice, or maize (fodder maize and sweet maize / sweet corn and field corn); beets such as sugar beets or fodder beets; fruits such as pome fruits, stone fruits, or soft fruits such as apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries, or gooseberries; leguminous plants such as beans, lentils, peas, alfalfa, or soybeans; oilseed plants such as rapeseed (oilseed rape), Brassica rapa, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palm, peanuts, or soybeans; cucurbits such as winter squash, pumpkin, cucumber, or melon; fiber plants such as cotton, flax, hemp, or jute; citrus fruits such as oranges, lemons, grapefruits, or mandarins; vegetables such as Eggplant, spinach, lettuce (e.g. iceberg lettuce), endive, cabbage, asparagus, cabbage, carrot, onion, garlic, leek, tomato, potato, gourd or bell pepper; bay plants, such as avocado, cinnamon or camphor; energy and feedstock plants, such as corn, soy, rapeseed, sugarcane or oil palm; tobacco; nuts, such as walnuts; pistachios; coffee; tea; bananas; grapevines (table grapes and juice grapevines); hops; sweet leaf (also known as stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g. carnations, petunias, geraniums / pelargoniums, pansies and impatiens), shrubs, broadleaf trees (e.g. poplars) or evergreen plants, such as conifers; eucalyptus; turf; lawns; grasses, such as grasses used for animal feed or ornamental purposes. Preferred plants include potato, sugar beet, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybean, rapeseed, legumes, sunflower, coffee, or sugar cane; fruit; vine; ornamental; or vegetable, such as cucumber, tomato, bean, or squash.

[0974] The term "cultivated plants" is to be understood as including plants which have been modified by mutagenesis or genetic engineering in order to provide the plants with new traits or to modify already existing traits.

[0975] Mutagenesis includes random mutagenesis techniques using X-rays or mutagenic chemicals, but also targeted mutagenesis techniques to generate mutations at specific loci in the plant genome. Targeted mutagenesis techniques often use oligonucleotides or proteins like CRISPR / Cas, zinc finger nucleases, TALENs, or meganucleases to achieve targeted effects.

[0976] Genetic engineering usually uses recombinant DNA technology to produce modification in plant genome, and this type of modification can not easily obtain by hybridization, mutagenesis or natural recombination under natural environment.Typically, one or more genes are integrated into the genome of plant to increase proterties or improve proterties.The genes of these integrations are also referred to as transgenic in this area, and the plant that comprises this type of transgenic is called transgenic plant.The plant transformation process produces several transformation events usually, and they are different on the genomic locus that has integrated transgenic therein.The plant that comprises specific transgenic on specific genomic locus is usually described as comprising specific " event ", and it is referred to by specific event name.The proterties that have been introduced in plant or modified particularly comprise herbicide tolerance, insect resistance, the yield of raising and to abiotic conditions such as drought tolerance.

[0977] Herbicide tolerance has been generated by the use of mutagenesis as well as by genetic engineering. Plants that have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional mutagenesis and breeding methods include those that may be named Commercially available plant varieties. However, most herbicide tolerance traits have been generated through the use of transgenics.

[0978] Herbicide tolerance has been developed to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors like isoxaflutole and mesotrione.

[0979] Transgenics that have been used to provide herbicide tolerance traits include: for glyphosate tolerance: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for glufosinate tolerance: pat and bar, for 2,4-D tolerance: aad-1 and aad-12, for dicamba tolerance: dmo, for benzonitrile herbicide tolerance: bxn, for sulfonylurea herbicide tolerance: zm-hra, csr1-2, gm-hra, S4-HrA, for ALS inhibitor herbicide tolerance: csr1-2, for HPPD inhibitor herbicide tolerance: hppdPF, W336 and avhppd-03.

[0980] Transgenic maize events comprising herbicide tolerance genes are, for example, but not exclusively, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO- 1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

[0981] Transgenic soybean events comprising herbicide tolerance genes are, for example, but not exclusively, 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, SYHT H2, W62, W98, FG72 and CV127.

[0982] Transgenic cotton events comprising herbicide tolerance genes are, for example, but not exclusively, 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.

[0983] Transgenic canola events comprising a herbicide tolerance gene are, for example, but not exclusively, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3.

[0984] Insect resistance is primarily produced by transferring bacterial genes for insecticidal proteins into plants. The most commonly used transgenics are toxin genes from Bacillus species (Bacillus spec.) 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 are also transferred into other plants. In particular, genes encoding protease inhibitors, such as CpTI and pinII, are used. Another approach uses transgenics to produce double-stranded RNA in plants to target and downregulate insect genes. An example of such a transgenic is dvsnf7.

[0985] Transgenic maize events comprising a gene for an insecticidal protein or double-stranded RNA are, for example, but not exclusively, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418, and MZIR098.

[0986] Transgenic soybean events comprising a gene for an insecticidal protein are for example, but not exclusively, MON87701, MON87751 and DAS-81419.

[0987] Transgenic cotton events comprising a gene for an insecticidal protein are, for example, but not exclusively, 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.

[0988] Increased yield is achieved by increasing ear biomass using the transgene athbl7 present in maize event MON87403, or by enhancing photosynthesis using the transgene bbx32 present in soybean event MON87712.

[0989] Cultivated plants containing altered oil content have been produced using the following 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.

[0990] Tolerance to abiotic conditions, particularly drought tolerance, has been demonstrated through the use of the transgene cspB contained by maize event MON87460 and through the use of the transgene cspB contained by soybean event IND- 41 -5 contains the transgenic Hahb-4 produced.

[0991] Traits are typically combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combinations of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different species of insects, in particular tolerance to Lepidoptera and Coleoptera insects, herbicide tolerance combined with one or more types of insect resistance, herbicide tolerance with increased yield, and herbicide tolerance combined with tolerance to abiotic conditions.

[0992] Plants containing single or stacked traits and genes and events that provide these traits are well known in the art. For example, detailed information about induced or integrated genes and corresponding events can be obtained from the websites of the following organizations: International Service for the Acquisition of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and Center for Environmental Risk Assessment (CERA) (http: / / www.cera.org / http: / / cera-gmc.org / GMCropDatabase), further information on specific events and methods for detecting them can be found in: rapeseed events MS1, MS8, RF3, GT73, MON88302, KK179 (WO 01 / 031042, WO 01 / 041558, WO 01 / 041558, WO 02 / 036831, WO 11 / 153186, WO 13 / 003558); cotton events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, 81910 (WO 02 / 034946, WO 02 / 100163, WO 02 / 100163, WO 03 / 013224, WO 04 / 072235, WO 04 / 039986, WO 05 / 103266, WO 05 / 103266, WO 06 / 128573, WO 07 / 017186, WO 08 / 122406, WO 08 / 151780, WO 12 / 134808, WO 13 / 112527); corn event GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, MON87419 (WO 98 / 044140, US 02 / 102582, US 03 / 126634, WO 04 / 099447, WO 04 / 011601, WO 05 / 103301, WO 05 / 061720, WO 05 / 059103、WO 06 / 098952、WO 06 / 039376、US 2007 / 292854、WO 07 / 142840、WO 07 / 140256、WO08 / 112019、WO 09 / 103049、WO 09 / 111263、WO 10 / 077816, WO 11 / 084621, WO 11 / 062904, WO11 / 022469, WO 13 / 169923, WO 14 / 116854, WO 15 / 053998, WO 15 / 142571);Potato events E12, F10, J3, J55, V11, X17, Y9 (WO 14 / 178910, WO 14 / 178913, WO 14 / 178941, WO 14 / 179276, WO 16 / 183445, WO 17 / 062831, WO 17 / 062825); Rice events LLRICE06, LLRICE601, LLRICE62 (WO 00 / 026345, WO 00 / 026356, WO 00 / 026345); soybean incident H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MO N87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419x DAS44406-6, MON87751 (WO 04 / 074492, WO 06 / 130436, WO 06 / 108674, WO 06 / 108675, WO 08 / 054747, WO 08 / 002872, WO 09 / 064652, WO09 / 102873, WO 10 / 080829, WO 10 / 037016, WO 11 / 066384, WO 11 / 034704, WO 12 / 051199, WO12 / 082548, WO 13 / 016527, WO 13 / 016516, WO 14 / 201235). ;

[0993] The use of the compositions according to the invention on cultivated plants can result in effects specific to the cultivated plants containing a certain gene or event. These effects may involve changes in growth behavior or altered resistance to biotic or abiotic stress factors. Such effects may particularly include increased yield, increased resistance or tolerance to insects, nematodes, fungi, bacteria, mycoplasmas, viruses or viroid pathogens, as well as early vigor, precocious or delayed maturity, cold or heat tolerance, and altered amino acid or fatty acid profiles or contents.

[0994] It has surprisingly been found that the pesticidal activity of the compounds of the present invention can be enhanced by the pesticidal properties of the modified plants. Furthermore, it has been found that the compounds of the present invention are suitable for combating pests that are resistant to the insecticidal properties or that have become resistant to the insecticidal properties of the modified plants. Furthermore, the compounds of the present invention are suitable for combating pests that are ineffective against the insecticidal properties, so that complementary insecticidal activities can be advantageously used.

[0995] The term "plant propagation material" refers to all reproductive parts of a plant, such as seeds, as well as vegetative plant material, such as cuttings and tubers (e.g. potatoes), which can be used to propagate the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, buds and other parts of a plant. It also includes seedlings and young plants that have been transplanted after germination from the soil or emergence. These plant propagation materials can be preventively treated with plant protection compounds before or at the time of planting or transplanting.

[0996] The term "seed" includes seeds and plant propagules of all kinds, including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruits, tubers, kernels, cuttings, cuttings, etc., and in preferred embodiments means true seeds.

[0997] Generally, a "pesticidally effective amount" means the amount of active ingredient required to achieve an observable effect on growth, including necrosis, death, retardation, prevention and removal of target organisms, destruction or otherwise reducing the presence and activity of target organisms. The pesticidally effective amount can vary for the various compounds / compositions used in the present invention. The pesticidally effective amount of a composition will also vary depending on prevailing conditions, such as the desired pesticidal effect and duration, climate, target species, location, mode of application, etc.

[0998] In the case of soil treatment, in-furrow application or application to pest residences or nests, the amount of active ingredient ranges from 0.0001 to 500 g / 100 m 2 , preferably 0.001 to 20 g / 100 m 2 .

[0999] For use in treating crop plants, for example, by foliar application, the application rate of the active ingredient of the present invention may be in the range of 0.0001 g to 4000 g per hectare, for example, 1 g to 2 kg per hectare or 1 g to 750 g per hectare, ideally 1 g to 100 g per hectare, more ideally 10 g to 50 g per hectare, for example 10 g to 20 g per hectare, 20 g to 30 g per hectare, 30 g to 40 g per hectare, or 40 g to 50 g per hectare.

[1000] The compounds of the present invention are particularly suitable for use in seed treatments to protect seeds from the infringement of insect pests (particularly soil insect pests), and to protect the roots and branches of the resulting rice seedlings from the damage of soil pests and foliar insects. Therefore, the invention still further relates to methods for protecting seeds from the infringement of insects (particularly soil insects), and protecting the roots and branches of the rice seedlings from the infringement of insects (particularly soil and foliar insects), said methods being included in treating seeds with the compounds of the present invention before sowing and / or after germination. Preferably, the roots and branches of the rice seedlings are protected. More preferably, the branches of the rice seedlings are protected from the infringement of sucking insects, chewing insects and nematodes.

[1001] The term "seed treatment" includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting and in-furrow application methods. Preferably, the seed treatment application of the active compound is carried out by spraying or dusting the seeds before sowing of the plants and before emergence of the plants.

[1002] The present invention also encompasses seeds coated with or containing an active compound. The term "coated with and / or containing" generally means that, in most cases, the active ingredient is on the surface of the propagation product at the time of application, although, depending on the method of application, a greater or lesser amount of the ingredient may penetrate the propagation product. When the propagation product is (re)planted, it can absorb the active ingredient.

[1003] Suitable seeds are, for example, seeds of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seeds of durum wheat and other wheats, barley, oats, rye, corn (fodder maize and sweet maize / sweet corn as well as field corn), soybeans, oil crops, crucifers, cotton, sunflower, banana, rice, oilseed rape, rapeseed oilseed rape, sugar beet, fodder beet, eggplant, potato, grass, lawn, turf, fodder grass, tomato, leek, pumpkin / squash, cabbage, iceberg lettuce, pepper, cucumber, melon, Brassica species, melon, beans, peas, garlic, onion, carrot, tuber plants such as potato, sugarcane, tobacco, grape, morning glory, geranium / pelargonium, pansy and impatiens.

[1004] Furthermore, the active compounds can also be used to treat seeds from plants which have been modified by mutagenesis or genetic engineering and which are, for example, resistant to the action of herbicides, fungicides or insecticides. Such modified plants have already been described in detail above.

[1005] Conventional seed treatment formulations include, for example, flowable concentrates FS, solutions LS, suspoemulsions (SE), powders DS for dry treatment, water-dispersible powders WS for slurry treatment, water-soluble powders SS, emulsions ES and EC, and gel formulations GF. These formulations can be applied to the seed diluted or undiluted. Application to the seed can be before sowing, directly to the seed, or after germination. Preferably, the formulation is applied under conditions that do not include germination.

[1006] The active substance concentration in the ready-to-use formulations obtainable after 2- to 10-fold dilution is preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40% by weight.

[1007] In a preferred embodiment, FS formulations are used for seed treatment. Typically, FS formulations may contain 1-800 g / l active ingredient, 1-200 g / l surfactant, 0 to 200 g / l antifreeze, 0 to 400 g / l binder, 0 to 200 g / l pigment, and up to 1 liter of solvent (preferably water).

[1008] Particularly preferred FS formulations of the compounds according to the invention for treating seeds generally 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 dispersant, up to 20% by weight (e.g. 5 to 20%) of an antifreeze agent, 0 to 15% by weight (e.g. 0.1 to 200 g / l) of a dispersant. The invention also includes pigments and / or dyes (e.g., 1% to 15% by weight), binders (adhesives / coating agents) in an amount of 0% to 40% by weight (e.g., 1% to 40% by weight), thickeners (e.g., 0.1% to 5% by weight), defoamers (e.g., 0.1% to 2% by weight), and preservatives (e.g., biocides, antioxidants, etc.) (e.g., in an amount of 0.01% to 1% by weight), and fillers / vehicles up to 100% by weight.

[1009] In seed treatment, the application rate of the compound of the 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, in particular 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.

[1010] The present invention also relates to seeds comprising a compound of the invention as defined herein or an agriculturally acceptable salt thereof. The amount of the compound of the invention or an agriculturally acceptable salt thereof is generally from 0.1 g to 10 kg per 100 kg of seeds, preferably from 1 g to 5 kg per 100 kg of seeds, in particular from 1 g to 1000 g per 100 kg of seeds. For certain crops, such as lettuce, this ratio may be higher.

[1011] The compounds of the present invention can also be used to improve the health of plants. Therefore, the present invention also relates to a method for improving the health of plants by treating plants, plant propagation materials and / or the site where the plants are growing or will grow with an effective and non-phytotoxic amount of the compounds of the present invention.

[1012] As used herein, "effective and non-phytotoxic amount" means that the compound is used in an amount that allows the desired effect to be obtained without causing any symptoms of phytotoxicity to the treated plants or plants growing on the treated propagules or treated soil.

[1013] The terms "plant" and "plant propagation material" are defined above.

[1014] "Plant health" is defined as the condition of a plant and / or its products, determined 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 greener leaves ("greening effect"), tolerance to abiotic stresses (e.g. drought) and / or biotic stresses (e.g. diseases), and production efficiency (e.g. harvest efficiency, processability).

[1015] The plant health indicators determined above may be interdependent and may be mutually causal. Each indicator is defined in the art and may be determined by methods known to those skilled in the art.

[1016] The compounds of the present invention are also suitable for use against non-crop insect pests. For use against such non-crop pests, the compounds of the present invention can be used as bait compositions, gels, general insect sprays, aerosols, ultra-low volume applications, and mosquito nets (impregnated or surface-applied). In addition, impregnation and rodding methods can be used.

[1017] As used herein, the term "non-crop insect pests" refers to pests that are particularly associated with non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitoes, bedbugs, crickets, or cockroaches.

[1018] The bait may be a liquid, solid or semisolid formulation (e.g. a gel). The bait employed in the composition is a product that is sufficiently attractive to stimulate insects such as ants, termites, wasps, flies, mosquitoes, crickets or cockroaches to feed on it. This attractiveness may be controlled by the use of feeding stimulants or sex pheromones. Feeding stimulants are selected, for example but not exclusively, from animal and / or plant proteins (meat meal, fish meal or blood meal, insect parts, egg yolks), from fats and oils of animal and / or plant origin, or from mono-, oligo- or poly-organic sugars, in particular from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or rotten parts of fruits, crops, plants, animals, insects or specific parts thereof may also be used as feeding stimulants. Sex pheromones are known to be more insect-specific. Specific pheromones are described in the literature (e.g. http: / / www.pherobase.com) and are known to those skilled in the art.

[1019] For use in bait compositions, typical levels of active ingredient are from 0.001 wt% to 15 wt%, ideally from 0.001 wt% to 5 wt% of active compound.

[1020] The formulations of the compounds of the invention as aerosols (e.g. in spray cans), oil sprays or pump sprays are highly suitable for professional or non-professional users to control pests such as flies, fleas, ticks, bedbugs, mosquitoes or cockroaches. Aerosol formulations preferably consist of the active compound; a solvent; additionally adjuvants such as emulsifiers, fragrance oils; if appropriate, stabilizers; and, if desired, a propellant.

[1021] Oil spray formulations differ from aerosol formulations in that no propellant is used.

[1022] When used in a spray composition, the content of the active ingredient is 0.001 wt% to 80 wt%, preferably 0.01 wt% to 50 wt%, most preferably 0.01 wt% to 15 wt%.

[1023] The compounds of the present invention and their corresponding compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers, as well as in moth papers, moth pads, or other vaporizer systems that do not rely on heat.

[1024] Methods of controlling infectious diseases transmitted by insects (e.g., malaria, dengue and yellow fever, lymphatic filariasis and leishmaniasis) using the compounds of the present invention and their corresponding compositions also include treating surfaces of sheds and houses, aerial spraying and impregnation of curtains, tents, clothing, mosquito nets, rape fly traps, etc. Insecticidal compositions for application to fibers, fabrics, knitwear, nonwovens, netting materials or foils and tarpaulins preferably comprise a mixture comprising an insecticide, optionally a repellent and at least one binder.

[1025] The compounds of the present invention and their compositions can be used to protect wooden materials, such as trees, wooden fences, sleepers, frames, artworks, etc., as well as buildings, and also building materials, furniture, leather, fibers, vinyl products, wires and cables, etc. from attack by ants, termites and / or beetles that destroy wood or textiles, and to control damage to crops or humans caused by ants and termites (for example, when the pests invade houses and public facilities or nest in yards, orchards or parks).

[1026] Typical application rates in protective materials are, for example, per m 2 Treatment material 0.001 g to 2000 g or 0.01 g to 1000 g of active compound, ideally per m 2 0.1g to 50g.

[1027] Insecticidal compositions for use in impregnating materials typically contain 0.001 wt% to 95 wt%, preferably 0.1 wt% to 45 wt% and more preferably 1 wt% to 25 wt% of at least one repellent and / or insecticide.

[1028] The compounds of the present invention are particularly suitable for being effective against animal pests such as arthropods, gastropods and nematodes, including but not limited to:

[1029] Insects from the order Lepidoptera, for example, Achroia grisella, Acleris spp. (e.g., A. fimbriaana, A. gloverana, A. variana); Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. (e.g., A. cyrtosema, A. orana); Aedia leucomelas, Agrotis spp. spp.) (e.g., 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 kuehniella, Anarsia lineatella, Anisota senatoria, Antheraea pernyi, Anticarsia (= Thermesia) spp. (e.g., A. gemmatalis); Apamea species. spp.), peanut moth (Aproaerema modicella), Archips spp. (such as fruit moth (A.argyrospila), apricot moth (A.fuscocupreanus), rose moth (A.rosana), scutellaria moth (A.xyloseanus)); apple moth (Argyresthia conjugella), striped moth (Argyroploces spp.), banded moth (Argyrotaenia spp.) (such as red banded moth (A.velutinana); Athetis mindara, Austroasca viridigrisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedellia species, Bonagota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola species, Cacoecia species (e.g., C. murinana, C. podana); Cactus borer (Cactoblastis cactorum), Cadra cautella, Calingo braziliensis, Caloptilis theivora, Capua reticulana, Carposina spp. (e.g., C. niponensis / C. sasakii); Cephus spp., Chaetocnema aridula, Cheimatobia brumata, Chilo spp. (e.g., C. indicus, C. suppressalis, C. partellus); Choreutis pariana, Choristoneura spp.) (e.g., C. conflicttana, C. fumiferana, C. longicellana, C. murinana, C. occidentalis, C. rosaceana); species of the genus Chrysodeixis (= Pseudoplusia) such as C. eriosoma and C. includens; Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp.), Cnaphalocrocis medinalis, Cnephasia spp., Cochylis hospes, Coleophora spp., Colias eurytheme, Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Corcyra cephalonica, Crambus caliginosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectalis, Cydia (=Carpocapsa) spp. such as C. pomonella and C. latiferreana; Dalaca noctuides, Datana integerrima (walnut yellow-necked boat moth), Dasychira pinicola (pinicola tussock moth), Dendrolimus spp. (e.g., D. pini, D. spectabilis, D. sibiricus); Grape leaf roller (Desmia funeralis), Diaphania spp. (e.g., D. nitidalis, D. hyalinata); Southwestern corn borer (Diatraea grandiosella), Diatraea saccharalis (cane sugarcane borer), Diphthera festiva (festive whitethroat), Earias spp. (e.g., E. insulana, E. vittella); Citrus fruit borer (Ecdytolophagus spp.). aurantianu), citrus cutworm (Egira (=Xylomyges) curialis), South American corn seedling borer (Elasmopalpus lignosellus), sweet potato stalk borer (Eldana saccharina), grape berry moth (Endopizaviteana), white looper moth (Ennomos subsignaria), Mexican rice borer (Eoreuma loftini), Ephestia spp. (such as E.cautella), E. elutella, E. kuehniella); Epinotia aporema, Epiphyas postvittana, Erannis tiliaria, Erionota thrax, Etiella spp., Eulia spp., Eupocilia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana, Faronta albilinea, Feltia spp. (e.g., F. subterranean); Galleria mellonella, Gracillaria spp.), Grapholita spp. (e.g., plum borer (G. funebrana), pear borer (G. molesta), apple borer (G. inopinata)); Halysidota spp., grape tobacco moth (Harrisina americana), Hedylepta spp., Helicoverpa spp. (e.g., pomegranate bollworm (H. armigera (=Heliothis armigera)), American bollworm (H. zea (=Heliothis zea))); Heliothis spp., such as tobacco budworm (H. assulta), H. subflexa, tobacco budworm (H. virescens); Hellula spp. spp.), such as the cabbage borer (H.undalis), the cabbage web moth (H.rogatalis; South American bollworm (Helocoverpa gelotopoeon), olive silkworm moth (Hemileuca oliviae), rice leaf cutter (Herpetogramma licarsisalis), defoliating looper (Hibernia defoliaria), brown weaver moth (Hofmannophila pseudospretella), sunflower borer (Homoeosoma electellum), tea moth (Homona magnanima), alfalfa armyworm (Hypena scabra), American gypsy moth (Hyphantria cunea), Padella's nest moth (Hyponomeuta padella), apple nest moth (Hyponomeutamalinellus), persimmon calyx moth (Kakivoria flavofasciata), tomato stem moth (Keiferia lycopersicella), eastern hemlock looper (Lambdina fiscellaria fiscellaria), northern hemlock leaf roller (Lambdina fiscellaria) lugubrosa), Lamprosema indicata, Laspeyresia molesta, Leguminivora glycinivorella, Lerodeaeufala, Leucinodes orbonalis, Leucoma salicis, Leucoptera spp. (e.g., L. coffeeella, L. scitella); Leuminivora lycinivorella, Lithocolletis blancardella, Lithophane antennata, Llattia octo (=Amyna axis), Lobesia botrana, Lophocampa spp., Loxagrotis bean rootworm. albicosta), Loxostege spp. (e.g., L. sticticalis, L. cereralis); Lymantria spp. (e.g., L. dispar, L.monacha; Lyonetia clerkella, Lyonetia prunifoliella, Malacosoma spp. (e.g., M. americanum, M. californicum, M. constrictum, M. neustria); Mamestra spp. (e.g., M. brassicae, M. configurata); Mamstra brassicae, Manduca spp. (e.g., M. quinquemaculata, M. sexta); Marasmia spp., Marmara spp., Maruca pod borer testulalis), Megalopyge lanata, Melanchrapicta, Melanitis leda, Mocis spp. (e.g., M. lapites, M. repanda); Mocis latipes, Monochroa fragariae, Mythimna separata, Nemapogoncloacella, Neoleucinodes elegantalis, Nepytias spp., Nymphula spp., Oiketicus spp., Omiodes indicata, Omphisa anastomosalis), winter looper moth (Operophterabrumata), yellow fir moth (Orgyia pseudotsugata), Oria spp., tea bush borer (Orthaga thyrisalis), Ostrinia spp. (such as European corn borer (O. nubilalis)); rice mudworm (Oulema oryzae), spring looper (Paleacrita vernata), pine armyworm (Panolis flammea), rice butterfly species (Parnara spp.), Papaipema nebris, Papiliocresphontes, Paramyelois transitella, Paranthreneleglis, Paysandisia archon, Pectinophora spp. (e.g., P. gossypiella), Peridroma saucia, Perileucoptera spp. (e.g., P. coffeeella), Phalera bucephala, Phryganidia californica, Phthorimaea spp. (e.g., P. operculella), Phyllocnistis citrella, Phyllonorycter spp.) (e.g., P. blancardella, P. crataegella, P. issikii, P. ringoniella); Pieris spp., such as P. brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra, Platynota spp. (e.g., P. flavedana, P. idaeusalis, P. stultana); Platyptilia carduidactyla, Plebejus argus, Plodia interpunctella, Plusia spp.), Plutella maculipennis, Plutella xylostella, Pontia protodica, Prays spp., Prodenia spp., Proxenus lepigone, Pseudaletia spp. (such as P. sequax), American armyworm (P.unipuncta); Pyrausta nubilalis (corn borer), Rachiplusia nu (two-colored bearded moth), Richia albicosta (Rhizobius ventralis), Rhyacionia frustrana (American pine moth), Sabulodesaegrotata (omnivorous looper), Schizura concinna (Red Peak caterpillar), Schoenobius spp., Schreckensteinia festaliella (Shreckensteinia festaliella), Scirpophaga spp. (such as S. incertulas and S. innotata); Scotia segetum (yellow cutworm), Sesamia spp. (such as S. inferens), Seudyra subflava (grape moth), Sitotroga cerealella), Sparganothis pilleriana, Spilonota lechriaspis, S. ocellina, 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, Syleptaderogata, Synanthedon spp.) (e.g., peach clearwing moth (S.exitiosa)), potato tuber moth (Tecia solanivora), white banana stem borer (Telehin licus), pine boat moth (Thaumatopoeapityocampa), apple tortoise moth (Thaumatotibia (=Cryptophlebia) leucotreta), pine boat moth (Thaumetopoea pityocampa), Thecla spp.), Theresimima ampelophaga, Thyrinteina spp., Tildenia inconspicuella, Tinea spp. (e.g. T. cloacella, T. pellionella); Tineola bisselliella, Tortrix spp. (e.g. T. viridana); Trichophagata petzella, Trichoplusia spp. (e.g. T. ni); Tuta (= Scrobipalpula) absoluta, Udea spp. (e.g. U. rubigalis, Udea); Virachola spp., Yponomeuta padella and Zeiraphera canadensis);.

[1030] Insects from the order Coleoptera, for example, Acalymma vittatum (striped cucumber beetle), Acanthoscehdes obtectus, Adoretus spp., Agelastica alni (alder leaf beetle), Agrilus spp. (e.g., A. anxius, A. planipennis, A. sinuatus); Agriotes spp. (e.g., A. fuscicollis, A. lineatus, A. obscurus); Alphitobius diaperinus (black fungus beetle), Amphimallus solstitialis (potato beetle), Anisandrus dispar (northern hairy wood beetle), Anisoplia truncatula (Austrian beetle), A. ... austriaca), furniture beetles (Anobium punctatum), copper-green beetles (Anomala corpulenta), red copper beetles (Anomala rufocuprea), Anoplophora spp. (such as A. glabripennis); Anthonomus spp. (such as A. eugenii, A. grandis, and A. pomorum); Anthrenus spp. (such as Aphthona euphoridae), Apion spp. (such as A. eugenii), sugarcane beetles (Apogonia spp.), red-tailed click beetles (Athoushaemorrhoidalis), Atomaria spp.) (e.g., A. linearis); Attagenus spp., Aulacophora femoralis, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. (e.g., B. lentis, B. pisorum, B. fabae, B.rufimanus); Byctiscus betulae, Callidiellum rufipenne, Callopistria floridensis, Callosobruchus chinensis, Cameraria ohridella, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp. (e.g., C. assimilis, C. napi); Chaetocnema tibialis, Cleonus mendicus, Conoderus spp. (e.g., C. vespertinus); Plum weevil (Conotrachelus spp.). nenuphar), Cosmopolites spp., Costelytra zealandica, Crioceris 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., southern corn rootworm (D. undecimpunctata), South American leaf beetle (D. speciosa), long-horned leaf beetle (D. longicornis), cucumber leaf beetle (D. semipunctata), corn rootworm (D. virgifera)); West Indian root beetle (Diaprepes abbreviates), Dichocrocis spp.), Rice Ironbeetle (Dicladispa armigera), Rhinoceros Beetle (Diloboderus abderus), Coconut Flower Weevil (Diocalandra frumenti / Diocalandra stigmaticollis), Red-breasted Longhorn Beetle (Enaphalodes rufulus), Plant-feeding Coccinella species (Epilachna spp.) (such as Mexican Bean Beetle (E. varivestis) and Potato Twenty-eight-spotted Ladybird (E. vigintioctomaculata)); Epitrix spp. (such as Tobacco Flea Beetle (E. hirtipennis) and Homozygous Flea Beetle (E. similarris); Dwarf Rhinoceros Beetle (Eutheola humilis), Brazilian Weevil (Eutinobothrus brasiliensis), Tobacco Borer (Faustinus cubae), Naked Spider Beetle (Gibbiumpsylloides), Broad-horned Float Beetle (Gnathocerus cornutus), Hellula undalis, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera 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., tobacco mudworm (L.bilineata), wheat mudworm (L.melanopus)); Leptinotarsa ​​spp., such as potato leaf beetle (L.decemlineata); Leptispa pygmaea, beet wild beetle (Limoniuscalifornicus), rice water weevil (Lissorhoptrus oryzophilus), Lixus spp.), Luperodes species, Lyctus species (such as L. bruneus); Liogenys fuscus, Macrodactylus species (such as M. subspinosus); Maladera matrida, Megaplatypus mutates, Megascelis species, Melanotus communis, Meligethes species (such as M. aeneus); Melolontha species (such as M. hippocastani, M. melolontha); West Indian sugarcane borer (Metamasius hemipterus), Microtheca species, Migdolus species 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, Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon spp.) (e.g., cabbage beetle (P. brassicae), P. cochleariae); eucalyptus longhorn beetle (Phoracantha recurva), pear leaf beetle (Phyllobius pyri), garden beetle (Phyllopertha horticola), Phyllophaga spp. (e.g., P. helleri); Phyllotreta spp., such as rapeseed beetle (P.chrysocephala), green-breasted cabbage flea beetle (P. nemorum), yellow-striped flea beetle (P. striolata), yellow-narrowed flea beetle (P. vittula); garden beetle (Phyllopertha horticola), Japanese beetle (Popillia japonica), Andean potato weevil (Premnotrypes spp.), yellow star beetle (Psacothea hilaris), rapeseed flea beetle (Psylliodes chrysocephala), large grain borer (Prostephanus truncates), rapeseed flea beetle species (Psylliodes spp.), spider beetle species (Ptinus spp.), Pulga saltona, grain borer (Rhizopertha dominica), Rhynchophorus spp. (e.g., R. billineatus, R. ferrugineus, R. palmarum, R. phoenicis, R. vulneratus); Saperda candida, Scolytus schevyrewi, Scyphophorus acupunctatus, Sitonalineatus, Sitophilus spp. (e.g., S. granaria, S. oryzae, S. zeamais); Sphenophorus spp. (e.g., S. levis); Stegobium paniceum, Sternechus spp.) (e.g., soybean stem weevil (S. subsignatus)); Strophomorphus ctenotus, Symphyletes species, Tanymecus species, Tenebrio molitor, Tenebrio mauretanicus, Tribolium species (e.g., red flour beetle (T. castaneum)); Trogoderma species (Trogoderma spp.), Tychius species (Tychius spp.), Xylotrechus species (e.g., grape beetle (X. pyrrhoderus)); and Zabrus species (Zabrus spp.) (such as the corn beetle (Z. tenebrioides));

[1031] Insects from the order Diptera, for example, Aedes spp., such as A. aegypti, A. albopictus, A. vexans; Anastrephaludens, Anopheles 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), Mediterranean fruit fly (Ceratitis capitata), Chrysomyia spp. (e.g. C. bezziana, C. hominivorax, C. macellaria); Atlantic fly (Chrysops atlanticus), Chrysops discalis, Chrysops silacea, Cochliomyia spp. (e.g. C. hominivorax); Contarinia spp. (e.g. C. sorghicola); Cordylobia anthropophaga, Culex species. spp.) (e.g., C. nigripalpus, C. pipiens, C. quinquefasciatus, 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, Drosophila spp. (e.g., D. suzukii), Fannia spp. (e.g., F. canicularis); Gastraphilus spp. (e.g., G. intestinalis); Geomyza tipunctata, Glossina spp.) (e.g., G. fuscipes, G. morsitans, G. palpalis, G. tachinoides); Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia spp. (e.g., H. platura); Hypoderma spp., such as H. lineata; Hyppobosca spp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. (e.g., L. sativae, L. trifolii); Lucilia spp.), such as L.caprina, L.cuprina, and L.sericata.

[1032] (L. sericata); Lycoria pectoralis, Mansonia titillanus, and species of the genus Lycoria

[1033] Mayetiola spp. (e.g., wheat gall midge (M. destructor)); Musca spp., such as M. autumnalis, M. domestica; Muscina stabulans, Oestrus spp. (e.g., sheep fly (O. ovis)); Opomyza florum, Oscinella spp. (e.g., Swedish straw fly (O. frit)); Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentipes, Phorbia spp. (e.g., onion fly (P. antiqua), radish fly (P. brassicae), wheat fly (P. coarctata)); Phytomyza gymnostoma, Prosimulium mixtum, carrot stem fly (Psila rosae), Columbia scale midge (Psorophora columbiae), two-colored scale midge (Psorophora discolor), fruit fly species (Rhagoletis spp.) (such as cherry fruit fly (R. cerasi), R. cingulate, western fruit fly (R. indifferens), blue orange fruit fly (R. mendax), apple fruit fly (R. pomonella)); Rivellia quadrifasciata, Sarcophaga spp. (such as red tail fruit fly (S. haemorrhoidalis)); Simulium vittatum, wheat midge (Sitodiplosismosellana), stable fly species (Stomoxys spp.) (e.g., stable fly (S. calcitrans)); Tabanus spp., such as T. atratus, T. bovinus, T. lineola, T. similis; Tannia spp., Thecodiplosis japonensis, Tipula oleracea, Tipula paludosa, and Wohlfahrtia spp.;

[1034] Insects from the order Thysanoptera, for example, Baliothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp. (e.g., F. fusca, F. occidentalis, F. tritici); Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Microcephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, grape thrips (Rhipiphorothrips scruentatus), Scirtothrips spp. (such as S. citri, S. dorsalis, S. perseae); Stenchaetothrips spp., Taeniothrips cardamoni, Taeniothrips inconsequens, Thrips spp. (such as T. imagines, T. hawaiiensis, T. oryzae, T. palmi, T. parvispinus, T. tabaci);

[1035] Insects from the order Hemiptera, for example Acizzia jamatonica, Acrosternum spp. (e.g. A. hilare); Acyrthosipon spp., such as A. onobrychis, A. pisum; Adelges laricis, Adelges tsugae, Adelphocoris spp. (e.g. A. rapidus, A. superbus); Aeneolamia spp., Agonascena spp., Aulacorthum solani, Aleurocanthus spp. woglumi), Aleurodes spp., Aleurodicus disperses, Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasatristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp.) (e.g., lentil aphid (A.craccivora), black bean aphid (A.fabae), strawberry root aphid (A.forbesi), cotton aphid (A.gossypii), tea aphid (A.grossulariae), corn root aphid (A.maidiradicis), apple aphid (A.pomi), elderberry aphid (A.sambuci), Schizonepeta aphid (A.schneideri), spiraecola); grape leafhopper (Arboridia apicalis), Arilus critatus, Aspidiella spp., Aspidiotus spp., Atanus spp.), Aulacaspis yasumatsui, Aphididae, Bactericera cockerelli (Paratrioza cockerelli), Bemisia spp. (e.g., B. argentifolii, B. tabaci / Aleurodes tabaci); Blissus spp. (e.g., B. leucopterus); Brachycaudus spp. (e.g., B. cardui, B. helichrysi, B. persicae, B. prunicola); Brachycolus spp., Brachycorynella asparagi, Brevicoryne brassicae), Cacopsylla spp. (e.g., 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 spp. onukii), walnut black-spotted aphid (Chromaphis juglandicola), black-brown round-shielded scale (Chrysomphalus ficus), corn leafhopper (Cicadulina mbila), Cimex spp. (such as tropical stink bug (C. hemipterus), temperate stink bug (C. lectularius)); Hall's long-shielded scale (Coccomytilus halli), Coccus spp. (such as brown soft scale (C. hesperidum), orange soft scale (C.pseudomagnoliarum); Corythucha arcuata, Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum, Cryptomyzus ribis, Ctenarytaina spatulata, Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeurodes spp. (e.g., D. citrifolii); Dalbulus maidis, Diaphorina spp. (e.g., D. citri); Diaspora spp. spp.), such as D. bromeliae; Dichelops furcatus, Diconocoris hewetti, species of the genus Doralis, Dreyfusia nordmannianae, Dreyfusia piceae, species of the genus Drosicha, species of the genus Dysaphis (such as D. plantaginea, D. pyri, and D. radicola); Dysaula corthumps eudosolani, species of the genus Dysdercus (such as D. cingulatus and D. intermedius); species of the genus Dysmicoccus spp.), Edessa species, Geocoris species, Empoasca species (such as E. fabae, E. solana); Epidiaspis leperii, Eriosoma species (such as E. lanigerum, E. pyricola); Grape leafhopper species (Erythroneuras spp.), Eurygaster species (such as E.integriceps); Euscelis bilobatus, Euschistus spp. (e.g., E. heros, E. impictiventris, E. servus); Fiorinia theae, Geococcus coffeae, Glycaspis brimblecombei, Halyomorpha spp. (e.g., H. halys); Heliopeltis spp., Homalodisca vitripennis (= H. coagulata), Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, Icerya spp. (such as I. purchase); Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanoideus floccissimus, Lepidosaphes spp. (such as L. ulmi); Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp.) (such as L. hesperus, L. lineolaris, L. pratensis); Maconellicoccus hirsutus, Marchalina hellenica, Macropes excavatus, Macrosiphum spp. (such as M. rosae, M. avenae, M. euphorbiae);euphorbiae); Macrosteles quadrilineatus, Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphissacchari, Melanocallis (=Tinocallis) caryaefoliae, Metcafiella species, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzocallis coryli, Murgantia spp., Myzus species. spp.) (such as M. ascalonicus, M. cerasi, M. nicotianae, M. persicae, M. varians); Nasonovia ribis nigri, Taiwan (China) leek aphid, Neomegalotomus spp., Nephotettix spp. (such as N. malayanus, N. nigropictus, N. parvus, N. virescens); Nezara spp., such as N. viridula; Nilaparvata lugens, Nysius huttoni), Oebalus spp. (such as the American rice stink bug (O.pugnax)); Oncometopia species, Ortheziapraelonga, Oxycaraenus hyalinipennis, Parabemisiamyricae, Parlatoria spp., Parthenolecanium spp. (such as the Oriental helmeted scale (P.corni), Peach wood scale (P.persicae)); Pemphigus spp., such as P.bursarius, P.populivenae; corn wax cicada (Peregrinus maidis), sugarcane flat-horned planthopper (Perkinsiella saccharicida), Phenacoccus spp. (e.g., P. aceris, P. gossypii); cotton aphid (Phloeomyzus passerinii), Phorodon humuli, Phylloxera spp. (e.g., P. devastatrix), square-backed leather bug (Piesmaquadrata), Piezodorus spp. (e.g., P. guildinii); cycad brown-spotted shield scale (Pinnaspis aspidistrae), Planococcus spp. spp.) (such as P. citri, P. ficus); Prosapia bicincta, Protopulvinaria pyriformis, Psallus seriatus, Pseudacystapersea, Pseudaulacaspis pentagona, Pseudococcus spp. (such as P. comstocki); Psylla spp., such as P. mali; 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. (e.g., R. pseudobrassicas, R. insertum, R. maidis, R. padi); Sagatodes spp., Sahlbergella singularis, Saissetia spp.), Sappaphismala, Sappaphis mali, Scaptocoris species, Scaphoides titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora species, Selenaspidus articulatus, Sitobion avenae, Sogata species, Sogatella furcifera, Solubea insularis, Spissistilus festinus (= Stictocephala festina), Stephanitis nashi, Stephanitis pyrioides, Stephanitis takeyai, Tenalaphara malayensis, Tetraleurodes perseae), Therioaphis maculate, Thyanta species (such as T. accerra and T. perditor); Tibraca species, Tomaspis spp., Toxoptera spp. (such as T. aurantii); Trialeurodes spp., such as T. abutilonea, T. ricini, and T. vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. (such as U. citri and U. yanonensis); and grape phylloxera (Viteus vitifolii).

[1036] Insects from the order Hymenoptera, for example Acanthomyops interjectus, Athalia rosae, Atta spp. (e.g. A. capiguara, A. cephalotes, A. laevigata, A. robusta, A. sexdens, A. texana), Bombus spp., Brachymyrmex spp., Camponotus spp. (e.g. C. floridanus, C. pennsylvanicus, C. modoc); Cardiocondyla nuda), Chalibion ​​species, Crematogaster species, Dasymutilla occidentalis, Diprion species, Dolichovespula maculata, Dorymyrmex species, Dryocosmus kuriphilus, Formica species, Hoplocampa species (e.g., H. minuta, H. testudinea); Iridomyrmex humilis, Lasius species (e.g., L. niger), Linepithema humile, Liometopum species, Leptocybe invasa, Monomorium spp.) (such as the yellow house ant (M. pharaonis)), Monomorium, Nylandria fulva, Pachycondylachinensis, Paratrechina longicornis, Paravespula species (such as P. germanica, P. pennsylvanica, P. vulgaris); Pheidole species (such as P. megacephala); Pogonomyrmex species (Pogonomyrmex spp.)) (such as red harvester ants (P. barbatus), California harvester ants (P. californicus)), red wasps (Polistes rubiginosa), prenolepis impairs, Pseudomyrmex gracilis, Schelipron species, orchid wasps (Sirex cyaneus), Solenopsis spp. (such as tropical fire ants (S. geminata), red fire ants (S. invicta), leaf-stealing ants (S. molesta), black fire ants (S. richteri), wood fire ants (S. xyloni)), cicada-killing mud wasps (Sphecius speciosus), saw-tooth mud wasps (Sphex spp.), Tapinoma spp. (such as black-headed sour-smelling ants (T. melanocephalum), T. sessile); pavement ant species (Tetramorium spp.) (such as T. caespitum and T. bicarinatum), Vespa spp. (such as V. crabro); Vespula spp. (such as V. squamosal); Fire ants (Wasmannia auropunctata), Xylocopa species;

[1037] Insects from the order Orthoptera, for example, Acheta domesticus, Calliptamus italicus, Chortoicetes terminifera, Ceuthophilus species, Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa species (e.g., G. africana, G. gryllotalpa); Gryllus species, Hieroglyphus daganensis, Kraussaria angulifera, Locusta species (e.g., L. migratoria, L. pardalina); Melanoplus species. spp.), such as M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, and M. spretus; Nomadacris septemfasciata, Oedaleus senegalensis, Scapteriscus spp., Schistocerca spp. (such as S. americana and S. gregaria), Stemopelmatus species, Tachycines asynamorus, and Zonozerus variegatus;

[1038] Pests from the class Arachnida, for example ticks and mites of the families Argasidae, Ixodidae and Sarcoptidae, such as 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. (e.g. D. silvarum, D. andersoni, D. variabilis), Hyalomma spp. spp.) (e.g., H. truncatum), Ixodes spp. (e.g., I. ricinus, I. rubicundus, I. scapularis, I. holocyclus, I. pacificus), Rhipicephalus sanguineus, Ornithodorus spp. (e.g., O. moubata, O. hermsi, O. turicata), Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp.) (e.g., P. ovis), Rhipicephalus spp. (e.g., R. sanguineus, R. appendiculatus, Rhipicephalus evertsi), Rhizoglyphus spp., Sarcoptes spp. (e.g., S. scabiei); Eriophyidae, including Aceria spp. (e.g., A. sheldoni, A.and citrus rust mites. pallidus and Polyphagotarsonemus latus, Stenotarsonemus spp. (Steneotarsonemus spinki); Tenuipalpidae, including Brevipalpus spp., such as B. phoenicis; Tetranychidae, including Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Petrobialatens, Tetranychus spp. spp.) (e.g., T.cinnabarinus, T.evansi, T.kanzawai, T.pacificus, T.phaseulus, T.telarius, and T.urticae); Bryobiapraetiosa; Panonychus spp., such as P.ulmi and P.citri; Metatetranychus spp. and Oligonychus spp. (e.g., O.pratensis, O.avocado, and O.perseae), tomato gall mite (Vasates lycopersici); Raoiella indica, Carpoglyphidae, including Carpoglyphus spp.; Penthaleidae spp., such as Halotydeus destructor; Demodicidae species, such as Demodex spp.; Trombicidea, including Trombicula spp.; Macronyssidae, including Ornothonyssus spp.; Pyemotidae, including Pyemotes tritici; Tyrophagus putrescentiae. putrescentiae; Acaridae, including the rough-legged flour mite (Acarus siro); Araneida, including the black widow (Latrodectus mactans), the country spider (Tegenaria agrestis), species of the genus Chiracanthium, species of the genus Lycosa, the greenhouse spider (Achaearaneatepidariorum), and the brown recluse spider (Loxosceles reclusa);

[1039] Pests from the phylum Nematoda, for example plant-parasitic nematodes, such as root-knot nematodes, species of the genus Meloidogyne, such as M. hapla, M. incognita, M. javanica; cyst-forming nematodes, species of the genus Globodera, such as G. rostochiensis; species of the genus Heterodera, such as H. avenae, H. glycines, H. schachtii, H. trifolii; seed gall nematodes, species of the genus Anguina; stem and leaf nematodes, for example species of the genus Aphelenchoides spp.), such as A. besseyi; hair nematodes, Belonolaimus spp., such as B. longicaudatus; pine nematodes, Bursaphelenchus spp., such as B. lignicolus and B. xylophilus; ring nematodes, Criconema spp., Criconemella spp. (such as C. xenoplax and C. ornata); and Criconemoides spp., such as Criconemoides informis; Mesocriconema spp.; stem and bulb nematodes, Ditylenchus spp. spp.), such as rice stem nematode (D.destructor) and Ditylenchus dipsaci; cone nematodes, species of the genus Dolichodorus; spiral nematodes, species of the genus Heliocotylenchus multicinctus; sheath and sheath-shaped nematodes, species of the genus Hemicycliophora and species of the genus Hemicriconemoides; Hirshmanniella; lance nematodes, species of the genus Hoploaimus; and pseudo-root-knot nematodes, species of the genus Nacobbus.); Needlenematodes, species of the genus Longidorus, such as L. elongatus; Lesion nematodes, species of the genus Pratylenchus, such as P. brachyurus, P. neglectus, P. penetrans, P. curvitatus, and P. goodeyi; Burrowing nematodes, species of the genus Radopholus, such as R. similis; Rhadopholus spp.; Rhodopholus spp.; Renal nematodes, species of the genus Rotylenchus spp.), such as R. robustus and R. reniformis; Scutellonema spp.; short and thick root nematodes, Trichodorus spp., such as T. obtusus and T. primitivus; Paratrichodorus spp., such as P. minor; dwarf nematodes, Tylenchorhynchus spp., such as T. claytoni and T. dubius; citrus nematodes, Tylenchulus spp., such as T. semiipenetrans; Dagger nematodes. nematode), Xiphinema spp.; and other plant-parasitic nematode species;

[1040] Insects from the order Blattodea, for example Macrotermes spp., such as M. natalensis; Cornitermes cumulans, Procornitermes spp., Globitermes sulfureus, Neocapritermes spp. (such as N. opacus, N. parvus); Odontotermes spp., Nasutitermes spp. (such as N. corniger); Coptotermes spp. spp.), such as the Taiwan (China) coptotermes, C. gestroi, and C. acinaciformis; Reticulitermes spp., such as R. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R. lucifugus, and R. virginicus; Heterotermes spp., such as H. aureus, H. longiceps, and H. tenuis; Cryptotermes spp. spp.), such as C.brevis and C.cavifrons; Incisitermes spp., such as I.minor and I.snyderi; Marginitermes hubbardi and Kalotermes flavicollis; Neotermes spp. (such as N.castaneus); Zootermopsis spp. (such as Z.angusticollis and Z.nevadensis); Mastotermes spp. (such as M.darwiniensis); Blatta spp.), such as B. orientalis and B. lateralis; Blattella spp., such as B.asahinae), German cockroach (B. germanica); Madeira cockroach (Rhyparobia maderae), Cuban cockroach (Panchlora nivea), Periplaneta spp. (such as American cockroach (P. americana), Australian cockroach (P. australasian), Brown cockroach (P. brunnea), American cockroach (P. fuliginosa), Japanese cockroach (P. japonica)); Long-bearded cockroach (Supella longipalpa), Pennsylvania cockroach (Parcoblatta pennsylvanica), Florida forest cockroach (Eurycotis floridana), Sugarcane cockroach (Pycnoscelus surinamensis), etc.

[1041] Insects from the order of the Siphonoptera, for example, Cediopsylla simples, Ceratophyllus spp., Ctenocephalides spp. (e.g. C. felis, C. canis), Xenopsylla cheopis, Pulexirritans, Trichodectes canis, Tunga penetrans and Nosopsyllus fasciatus,

[1042] Insects from the order Thysanura, for example, Lepisma saccharina, Ctenolepisma urbana and Thermobia domestica,

[1043] Pests from the class Chilopoda, such as Geophilus spp., Scutigera spp. (e.g. Scutigera coleoptrata);

[1044] Pests from the class Diplopoda, such as millipedes (Blaniulus guttulatus), Julus spp., and Narceus spp.,

[1045] Pests from the class Symphyla, such as white pine borer (Scutigerella immaculata),

[1046] Insects from the order Dermaptera, for example, Forficula auricularia,

[1047] Insects from the order Collembola, for example Onychiurus spp., such as Onychiurus armatus,

[1048] Pests from the order Isopoda, such as Armadillidium vulgare, Oniscus asellus, Porcellio scaber,

[1049] Insects from the order of the Phthiraptera, for example Damalinia spp., Pediculus spp. (e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pediculus humanus humanus); Pthirus pubis, Haematopinus spp. (e.g. Haematopinus eurysternus, Haematopinus suis); Linognathus spp., such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp.,

[1050] Examples of further pest species that can be controlled by the compounds of formula (I) include: from the phylum Mollusca, class Bivalvia, for example Dreissena spp.; class Gastropoda, for example Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galbas spp., Lymnaea spp., Oncomelania spp., Pomacea canaliclata, Succinea spp.; from the class Helmins, for example Ancylostoma spp. duodenale), Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia 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.), African eyeworms (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 spiralis britovi), Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.

[1051] 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 in 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 or infection, which method comprises administering or applying to the animal orally, topically or parenterally a parasiticidally effective amount of a compound of the present invention.

[1052] The present invention also relates to the non-therapeutic use of the compounds of the present invention for treating or protecting animals from parasitic infestation and infection. In addition, the present invention relates to a non-therapeutic method for treating or protecting animals from parasitic infestation and infection, which method comprises applying to the site a parasiticidally effective amount of a compound of the present invention.

[1053] The compounds of the present invention are further suitable for use in combating or controlling parasites in and on animals. In addition, the present invention relates to a method for combating or controlling parasites in and on animals, the method comprising contacting the parasites with a parasiticidal effective amount of a compound of the present invention.

[1054] 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 for combating or controlling parasites, which method comprises applying to a locus a parasiticidally effective amount of a compound of the present invention.

[1055] The compounds of the invention may be effective by contact (via soil, glass, walls, mosquito nets, carpets, rugs or animal parts) and ingestion (e.g. baits). Furthermore, the compounds of the invention may be applied to any and all developmental stages.

[1056] The compound of the present invention can be administered as such or in the form of a composition comprising the compound of the present invention.

[1057] The compounds of the invention can also be applied together with mixed partners which act against pathogenic parasites, for example with synthetic coccidiosis compounds, polyether antibiotics (such as amprolium, chlorpheniramine, toltrazuril, monensin, salinomycin, maduramicin, lasalocid, narasin or semdomicin) or with other mixed partners as defined above or in the form of compositions comprising such mixtures.

[1058] The compounds of the present invention and compositions containing them can be administered orally, parenterally or topically (eg, transdermally). The compounds of the present invention can be effective systemically or non-systemically.

[1059] Administration can be carried out prophylactically, therapeutically or non-therapeutically. In addition, prophylactic administration can be carried out where the parasite is expected to occur.

[1060] As used herein, the term "contacting" includes direct contact (administering the compound / composition directly to the parasite, including or excluding direct administration to an animal, such as administration at its locus) and indirect contact (administering the compound / composition to the locus of the parasite). Contacting a parasite by administration to the locus of the parasite is an example of a non-therapeutic use of a compound of the invention.

[1061] The term "locus" means a habitat, food supply, breeding ground, area, material or environment outside an animal where a parasite is or may be growing.

[1062] As used herein, the term "parasite" includes both endoparasites and ectoparasites. In some embodiments of the present invention, endoparasites may be preferred. In other embodiments, ectoparasites may be preferred. Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, maggots, gnats, houseflies, flies, maggot fly larvae, chiggers, gnats, mosquitoes, and fleas.

[1063] The compounds of the invention are particularly useful against parasites of the following orders and species, respectively:

[1064] Fleas (Siphonaptera), for example, Ctenocephalides felis, Ctenocephalides canis, Xenopus cherubicus, human fleas, sand fleas and stomatitis fleas; cockroaches (Blattaria / Blattodea), for example, Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta fuligginosa, Periplaneta australis and Blatta orientalis; flies, mosquitoes (Diptera), for example, Aedes aegypti, Aedes albopictus, Aedes vexans, Anopheles mexicana, Anopheles quinquefasciatus, Anopheles disasterus, Anopheles styracidae, Anopheles styracidae, Anopheles styracidae, Anopheles styracidae albimanus, Anopheles gambiae, Anopheles freundii, Anopheles white-ankled, Anopheles minimus, Anopheles four-spotted, Red-headed blowfly, Maggot-infected goldfly, Screw-screw goldfly, Putrefactive goldfly, Middle-chambered fly, Static fly, Atlantic fly, Screw-screw fly, Anthropogone fly, Culex pipiens, Culex pipiens acuminata, Aedes mosquito, Culex pipiens quinquefasciatus, Culex pipiens annularis, Trichoderma unadorned, Trichoderma nigricornis, Human skin fly, Yellow-bellied toilet fly, Stomach fly, Glossina thornii, Glossina centrale, Glossina fuscipes, Glossinatachinoides, Haplodiplosis equestris, Liriomyza species, Hypodermalineata, Leptoconops torrens, Lucilia caprina, Lucilia copper, Lucilia sericata, Lycoria pectoralis, Mansonia species (Mansonia spp.), housefly, stable fly, sheep fly (Oestrus ovis), silver-legged sandfly, Columbian scale midge, dichromatic scale midge, Prosimulium mixtum, red-tailed flesh fly, flesh fly species, tape fly, stable biting fly (Stomoxys calcitrans), gadfly (Tabanus bovinus), black horsefly (Tabanus atratus), fine-striped horsefly (Tabanus lineola), and Tabanus similis; lice (order Pediculus), for example, human head louse, human louse, pubic louse, bovine blood louse, hog blood louse, bovine jaw louse, bovine feather louse, chicken feather louse, chick feather louse, and buffalo blind louse; ticks and parasitic mites (order Parasitiformes): ticks (order Ixodida), for example, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, pacificus), Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata, and parasitic mites (Mesostigmata), such as Ornithonyssus bacoti and Dermanyssus gallinae; Actinedida (Prostigmata), and Acaridida (Astigmata), such as Acarapis spp., Cheyletiella spp.), Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.), Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp.; Bugs (Heteroptera): Cimex lectularius, Cimex lectularius, Reduvius senilis, Triatomines spp., Rhodnius ssp., Panstrongylus spp. ssp.) and Ariluscritatus; from the order of the Anoplurida, for example, Haemaphysalis spp., Longipalpis spp., Pediculus spp., Phtirus spp., and Solenopotes spp.; from the order of the Mallophagida (suborder Arnblycerina and Ischnocerina), for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.); Ascaris: Wipeworms and Trichosyringida, e.g., Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp.; Rhabditida, e.g., Rhabditis spp., Strongyloides spp., Helicephalobus spp.; Strongylida, e.g., Strongylus spp.), Ancylostoma species, Necatora americanus, Bunostomum species (Hookworm), Trichostrongylus species, Haemonchus contortus, Osterlella species, Cooperia species, Dictyocaulus species, Cyathostoma species, Nodosa species, Stephanurus dentatus, Ollulanus species, Chabertia species, Stephanurus dentatus, Syngamus trachea, Ancylostoma species, Uncinaria species, Globocephalus species, Necator species spp.), Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophymarenale; intestinal roundworms (order Ascaridida), for example, Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, pinworms (threadworms), Toxocara canis, Toxascaris leonine, Skrjabinema spp.) and Oxyuris equi; from the order of the Camelids, for example, Guinea worm (guinea worm); from the order of the Spirurida, for example, Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp., Dipetalonemas spp.), Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.; Spiny-headed worms (Acanthocephala), for example, Acanthocephalus spp., Macracanthorhynchus hirudinaceus, and Oncicola spp.; Planarians (Plathelminthes): Trematodes (Trematoda), for example, Fascioloides spp., Fascioloides magna, Paragonimus spp., Diplocoelensis spp., Fasciolopsis buski, Clonorchis sinensis, and Clonorchis spp. sinensis), Schistosoma spp., Trichobilharzia spp., Alariaalata, Paragonimus spp. and Nanocyetes spp.; Cercomeromorpha, in particular tapeworms (tapeworms), for example Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp. spp.), Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.

[1065] As used herein, the term "animal" includes warm-blooded animals (including humans) and fish. Preferred are mammals such as cattle, sheep, pigs, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, buffaloes, donkeys, fallow deer and reindeer, as well as fur animals such as mink, chinchillas and raccoons, birds such as hens, geese, turkeys and ducks, and fish such as freshwater fish and saltwater fish such as salmon, carp and eels. Particularly preferred are domestic animals such as dogs or cats.

[1066] In general, a "parasiticidally effective amount" is intended to mean the amount of active ingredient required to achieve an observable effect on growth, including necrosis, death, retardation, prevention and removal of target organisms, destruction or otherwise reducing the presence and activity of target organisms. The parasiticidally effective amount may vary for the various compounds / compositions used in the present invention. The parasiticidally effective amount of a composition will also vary depending on prevailing conditions, such as the desired parasiticidal effect and duration, target species, mode of administration, etc.

[1067] Generally, it is advantageous to administer the compounds of the invention in a total amount of 0.5 mg / kg to 100 mg / kg / day, preferably 1 mg / kg to 50 mg / kg / day.

[1068] For oral administration to warm-blooded animals, the compound of formula I can be formulated into animal feed, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, immersions, gels, tablets, boluses, and capsules. In addition, the compound of formula I can be administered to the animal in the animal's drinking water. For oral administration, the dosage form selected should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight / day, preferably 0.5 mg / kg to 100 mg / kg of animal body weight / day of the compound of formula I.

[1069] Alternatively, the compound of formula I can be administered to animals parenterally, for example, by intracavitary, intramuscular, intravenous or subcutaneous injection. For subcutaneous injection, the compound of formula I can be dispersed or dissolved in a physiologically acceptable carrier. 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 to animals transdermally. For parenteral administration, the selected dosage form should provide the compound of formula I at 0.01 mg / kg to 100 mg / kg animal body weight / day for the animal.

[1070] The compounds of formula I can also be applied topically to animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations, as well as in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays typically contain 0.5 ppm to 5,000 ppm, preferably 1 ppm to 3,000 ppm, of the compound of formula I. In addition, the compounds of formula I can be formulated into ear tags for animals, particularly quadrupeds such as cattle and sheep.

[1071] Suitable formulations are:

[1072] - solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pour-on preparations, gels;

[1073] - Emulsions and suspensions for oral or transdermal administration; semisolid preparations;

[1074] - formulations of the active compounds with an ointment base or an oil-in-water or water-in-oil emulsion base;

[1075] - solid dosage forms, such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and shaped articles containing the active compound.

[1076] Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding additional adjuvants (such as acids, bases, buffer salts, preservatives and solubilizers). Suitable adjuvants for injection solutions are known in the art. The solution is filtered and aseptically filled.

[1077] Oral solutions are administered directly. Concentrates are administered orally after pre-diluting to the use concentration. Oral solutions and concentrates are prepared according to the prior art and, as described above, no sterile procedures are required for injectable solutions.

[1078] The solution for application on the skin is dripped, spread, rubbed, sprinkled or sprayed. The solution for application on the skin is prepared according to the prior art and does not require sterile procedures as described above for the injection solution.

[1079] The gel is applied or spread on the skin or introduced into a body cavity. The gel is prepared by treating a solution prepared as described in the case of the injectable solution with sufficient thickening agent to obtain a transparent material with an ointment-like consistency. Suitable thickening agents are known in the art.

[1080] The pour-on formulation is sprayed or applied to a defined area of ​​skin, where the active compound penetrates the skin and acts systemically. Pour-on formulations are prepared by dissolving, suspending, or emulsifying the active compound in a suitable skin-compatible solvent or solvent mixture. If appropriate, other adjuvants such as colorants, substances that promote bioabsorption, antioxidants, light stabilizers, and binders are added. Suitable such adjuvants are known in the art.

[1081] Emulsions can be taken orally, administered transdermally or given as injections. Emulsions can be water-in-oil or oil-in-water. They are prepared by dissolving the active compound in a hydrophobic phase or a hydrophilic phase, and with the help of a suitable emulsifier and (if appropriate) other adjuvants (such as colorants, substances that promote absorption, preservatives, antioxidants, light stabilizers, viscosity-increasing substances), homogenizing the solvent of the other phase. Suitable hydrophobic phase (oil), suitable hydrophilic phase, suitable emulsifier and other suitable adjuvants for emulsions are known in the art.

[1082] Suspensions can be administered orally or topically / transdermally. They are prepared by suspending the active compound in a suspending agent and, if appropriate, adding other adjuvants such as wetting agents, colorants, substances that promote bioabsorption, preservatives, antioxidants, and light stabilizers. Suitable suspending agents and other suitable adjuvants for suspensions (including wetting agents) are known in the art.

[1083] Semisolid preparations can be administered orally or topically / dermally. They differ from the suspensions and emulsions described above only in their higher viscosity.

[1084] For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate, with the addition of auxiliaries, and brought into the desired form. Suitable auxiliaries for this purpose are known in the art.

[1085] Compositions useful in the present invention may generally contain from about 0.001% to 95% of a compound of the present invention.

[1086] The ready-to-use preparations contain the 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.

[1087] The preparations to be diluted before use contain the compounds active against ectoparasites in a concentration of 0.5% to 90% by weight, preferably 1% to 50% by weight.

[1088] Furthermore, the preparations comprise the compounds of the formula I acting against endoparasites in a concentration of 10 ppm to 2% by weight, preferably 0.05% to 0.9% by weight, very particularly preferably 0.005% to 0.25% by weight.

[1089] Topical administration can be carried out using shaped articles containing the compound, such as coils, tags, ear tags, tapes for attachment to parts of the body, and adhesive strips and foils.

[1090] Generally, it is advantageous to administer a solid formulation of the compound of the invention which releases a total amount of 10 to 300 mg / kg, preferably 20 to 200 mg / kg, most preferably 25 to 160 mg / kg of the treated animal body weight over the course of three weeks.

[1091] Examples:

[1092] By appropriately varying the starting materials, the procedures described in the preparation examples below are used to obtain further compounds of the formula I. The compounds obtained in this way are listed together with the physical data in Table C below.

[1093] Compounds can be detected by, for example, coupled high performance liquid chromatography / mass spectrometry (HPLC / MS), 1 The samples can be characterized by H-NMR and / or their melting points.

[1094] Analytical HPLC - Method 1: Agilent Eclipse Plus C18, 50X 4,6 mm, ID 5 μm; Elution: A = 10 mM ammonium formate (0.1% formic acid), B = acetonitrile (0.1% formic acid), flow rate = 1.2 ml / min at 30°C; Gradient: 10% B to 100% B - 3 min, hold 1 min, 1 min - 10% B. Run time = 5.01 min.

[1095] Analytical HPLC - Method 2: Kinetex XB C18 1,7μ 50 x 2,1 mm; A = water + 0.1% TFA, B = acetonitrile, flow rate = 0.8 ml / min - 1.0 ml / min in 1.5 min at 60°C; gradient: 5% B to 100% B - 1.5 min.

[1096] 1 H-NMR: Signals are expressed relative to tetramethylsilane (corresponding to 13 C-NMR is characterized by chemical shift (ppm, δ [delta]) in CDCl 3 ), its multiplicity and its integrity (relative number of given hydrogen atoms). The following abbreviations are used to characterize the multiplicity of the signals: m = multiplet, q = quartet, t = triplet, d = doublet, and s = singlet.

[1097] Abbreviations used are: d for day, h for hour, min for minute, RT / room temperature for 20°C-25°C, Rt for retention time; DMSO for dimethyl sulfoxide, OAc for acetate, EtOAc for ethyl acetate, IPA for isopropanol, MeOH for methanol, EtOH for ethanol, THF for tetrahydrofuran, DMF for N,N-dimethylformamide, and t-BuOH for tert-butanol.

[1098] Preparation example:

[1099] Example C-1:

[1100] N-[1-[4-[[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]

[1101] Synthesis of [carbamoyl]amino]-3-methyl-phenyl]-3-methyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide

[1102] Step 1: Synthesis of 3-methyl-1H-pyrazol-4-amine

[1103] 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 h. The progress of the reaction was monitored by GCMS analysis. The reaction mixture was filtered through a pad of celite, 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).

[1104] Step 2: Synthesis of N-(3-methyl-1H-pyrazol-4-yl)-4-(trifluoromethoxy)benzamide

[1105] 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 h. 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 obtain the desired product (8.0 g) as a brown solid. 1H NMR (300MHz, DMSO-d6) δ12.43(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).

[1106] Step 3: Synthesis of N-[3-methyl-1-(3-methyl-4-nitro-phenyl)pyrazol-4-yl]-4-(trifluoromethoxy)benzamide:

[1107] 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 h. 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 a 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) + ; 1 H NMR (300MHz, DMSO-d6) δ10.15(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).

[1108] Step 4: Synthesis of N-[1-(4-amino-3-methyl-phenyl)-3-methyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide:

[1109] 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 h. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (50 mL) and basified with solid sodium bicarbonate, 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 washing with n-pentane (2 mL x 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)δ9.95(s,1H),8.36(s,1H),8.08(d,J=8.8Hz,2H),7.53(d,J=8.2Hz,2H),7.3 4(d,J=2.2Hz,1H),7.29–7.23(m,1H),6.66(d,J=8.5Hz,1H),4.93(s,2H),2.25(s,3H),2.12(s,3H).

[1110] 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:

[1111] At 0 DEG C, to a stirred solution of N-[1-(4-amino-3-methyl-phenyl)-3-methyl-pyrazole-4-yl]-4-(trifluoromethoxy)benzamide (0.15g) in dry THF (5mL), add 4-nitrophenyl chloroformate (0.077g). Allow the reaction mixture to be stirred at room temperature for 2h. Monitor the progress of the reaction by TLC. The reaction mixture is cooled to 0 DEG C again, and add N, N-diisopropylethylamine (0.122mL), then add 2-imino-3-(2-isopropyl-5-methyl-phenyl) thiazolidine-4-one (0.116g). In the reaction mixture, add dry acetonitrile (5mL) and tripotassium phosphate (0.149g). Allow the reaction mixture to be stirred at room temperature for 12h. Monitor the progress of the reaction by TLC. The reaction mixture is diluted with water (20mL) and extracted with EtOAc (20mL 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) δ10.03(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),7.2 7(d,J=6.7Hz,1H),7.07(s,1H),4.17(m,1H),4.06(m,2H),2.72–2.65(m,1H),2.3 2(s,3H),2.29(s,3H),2.20(s,3H),1.21(d,J=6.9Hz,3H),1.10(d,J=6.8Hz,3H).

[1112] Example C-2:

[1113] 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:

[1114] Step 1: Synthesis of N-methyl-N-[3-methyl-1-(4-nitrophenyl)pyrazol-4-yl]-4-(trifluoromethoxy)benzamide:

[1115] 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 iodomethane (0.9 g). The reaction mixture was stirred at 50 ° C until the starting material was consumed. Subsequently, DMF was evaporated and EtOAc was added to the remaining residue. The precipitate was filtered off and purified by column chromatography to obtain the desired product (2 g). 1 H NMR (400 MHz, CHLOROFORM-d) δ 8.33–8.25 (m, 2H), 7.71 (d, J = 8.3 Hz, 3H), 7.45 (d, J = 8.3 Hz, 2H), 7.10 (m, 2H), 3.41 (s, 3H), 2.18 (s, 3H).

[1116] Step 2: Synthesis of N-[1-(4-aminophenyl)-3-methyl-pyrazol-4-yl]-N-methyl-4-(trifluoromethoxy)benzamide:

[1117] N-methyl-[3-methyl isophthalic acid-(4-nitrophenyl) pyrazole-4-yl]-4-(trifluoromethoxy) benzamide (2g) is dissolved in a 1:1 mixture of EtOAc (16.5mL) and EtOH (16.5mL). At room temperature, tin chloride (II) dihydrate (4.7g) is added to the reaction mixture. Reaction progress is monitored by TLC, and after the consumption of starting material, the reaction is quenched by adding saturated sodium bicarbonate aqueous solution (220mL). The reaction mixture is filtered through a celite pad, and the organic phase is extracted three times with EtOAc. The organic phase merged is dried over magnesium sulfate, and the residue is purified by flash chromatography to obtain the required product (1.8g). 1 H NMR (400 MHz, CHLOROFORM-d) δ 7.52–7.33 (m, 3H), 7.24 (d, J = 8.3 Hz, 2H), 7.06 (d, J = 8.3 Hz, 2H), 6.78–6.55 (m, 2H), 3.65 (m, 2H), 3.40 (s, 3H), 2.08 (s, 3H).

[1118] 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):

[1119] To a stirred solution of N-[1-(4-aminophenyl)-3-methylpyrazole-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. As indicated by TLC, the starting material was consumed after stirring at room temperature for 3 h. The solvent was evaporated and the crude product was used directly in the next step. The residue was dissolved in acetonitrile (15 mL) and 2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidine-4-one (0.2 g), diisopropylamine (0.25 mL) and potassium phosphate (0.3 g) were then added. The reaction mixture was stirred at room temperature overnight and then diluted with water (40 mL). The organic phase was extracted three times with EtOAc, washed with brine and dried over magnesium sulfate. The desired product (0.36 g) was obtained by column chromatography. 1 H 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).

[1120] Example C-3:

[1121] 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:

[1122] 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):

[1123] Thiobiuret C-2 (160 mg) was dissolved in chloroform (5 mL), and methyl-N-(N'-chloro-N-methoxycarbonyl-carbamimidoyl)carbamate (Palau' ) (0.076 g) and stirred for 22 h. The solvent was partially evaporated, 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). 1HNMR (400 MHz, CHLOROFORM-d) d 7.57 (d, J = 8.7 Hz, 2H), 7.45-7.25 (m, 6H), 7.08 (d, J = 8.3 Hz, 2H), 6.93-6.88 (s, 1H), 3.97 (d, J = 3.2 Hz, 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).

[1124] Example C-4:

[1125] 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

[1126] Step 1: Synthesis of 3,5-dimethyl-1H-pyrazol-4-amine:

[1127] At room temperature to 3,5-dimethyl-4-nitro-1H-pyrazole (10g) in 250mL of EtOH:HO (4:1) in a stirred solution in a mixture, add Fe (11.872g) and ammonium chloride (37.9g). The reaction mixture is heated at 80 DEG C for 5h. The progress of the reaction is monitored by TLC. The reaction mixture is cooled to room temperature and filtered through a diatomaceous earth pad, and the diatomaceous earth pad is washed with EtOAc (100mL). The filtrate is concentrated under reduced pressure to a volume of two-thirds and diluted with EtOAc (100mL) again, and water (50mL) is added. Each layer is separated, and the organic layer is dried over sodium sulfate and concentrated under reduced pressure to obtain a crude product, which is purified by washing with n-pentane (25mL x 2), to obtain the desired product (4g) as a beige solid.

[1128] Step 2: Synthesis of N-(3,5-dimethyl-1H-pyrazol-4-yl)-4-(trifluoromethoxy)benzamide:

[1129] To a stirred solution of 3-methyl-4-aminopyrazole (4g) in dichloromethane (60mL) was added 4-trifluoromethoxybenzoic acid (7.4g) at 10°C, followed by diisopropylethylamine (25mL). The reaction mixture was cooled to 0°C, and 1-propanephosphonic anhydride solution (160.5mL, 50% solution in EtOAc) was added dropwise to the reaction mixture over a period of 4h. The progress of the reaction was monitored by HPLC. After the reaction was complete, the reaction mixture was added dropwise to water (750mL) and stirred for 60min. A white precipitate was formed, which was filtered and dried under reduced pressure to give the desired product (9.8g) as a white solid compound. HPLC / MS (Method 1): Rt: 1.75min; m / z=300 (M+1) + . 1 H NMR (300MHz, DMSO-d6) δ9.59 (s, 1H), 8.10 (d, J = 8.3Hz, 2H), 7.50 (d, J = 8.3Hz, 2H), 2.06 (s, 6H).

[1130] Step 3: Synthesis of N-[3,5-dimethyl-1-(4-nitrophenyl)pyrazol-4-yl]-4-(trifluoromethoxy)benzamide:

[1131] 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 h. 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)δ9.94(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).

[1132] Step 4: Synthesis of N-[1-(4-aminophenyl)-3,5-dimethyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide:

[1133] To a solution of N-[3,5-dimethyl-1-(4-nitrophenyl)pyrazol-4-yl]-4-(trifluoromethoxy)benzamide (20 g) in 127 mL of MeOH (300 mL) was added palladium on carbon (1.45 g). The reaction mixture was hydrogenated at 40 psi for 18 h. The progress of the reaction was monitored by TLC. The reaction mixture was filtered through a pad of celite, which was washed with MeOH (100 mL). The filtrate was concentrated under reduced pressure to give a 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 HNMR(500MHz,DMSO-d6)δ9.72(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).

[1134] Step 5: Synthesis of N-[1-(4-amino-3-chloro-phenyl)-3,5-dimethyl-pyrazol-4-yl]-4-(trifluoromethoxy)benzamide:

[1135] 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 h. 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 a 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) + . 1 H NMR(500MHz,DMSO-d6)δ9.75(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).

[1136] 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:

[1137] At 0 DEG C, to a stirred solution of N-[1-(4-amino-3-chloro-phenyl)-3,5-dimethyl-pyrazole-4-yl]-4-(trifluoromethoxy)benzamide (0.9g) in dry THF (15mL), chloroformic acid 4-nitrophenyl ester (0.512g) was added. The reaction mixture was allowed to stir at room temperature for 2h...

Claims

1. A compound of formula I in Q is -C(=O)-N(R 5 )-or-N(R 5 )-C(=O)-; R 5 is H, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkyl-C1-C6-alkoxy or C1-C6-alkyl-C3-C6-cycloalkyl, phenyl, 5- or 6-membered heteroaryl, -CH2-phenyl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or halogen, wherein these alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen or CN; 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 by halogen or CN; R 2 is H, C1-C6-alkyl, C3-C6-cycloalkyl or halogen, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN; B 1 Is N or CR B1 ; B 2 Is N or CR B2 ; B 3 Is N or CR B3 ; B 4 Yes CR B4 ; R B1 , R B2 , R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, wherein these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen; D is part DA or DB, R 3 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen or CN; R 4 is H, C1-C6-alkyl or C3-C6-cycloalkyl, wherein these alkyl and cycloalkyl moieties are unsubstituted or substituted by halogen, -O-(C=O)-C1-C6-alkyl, -O-(C=O)-C1-C6-alkoxy or CN; B is a 5- or 6-membered carbocyclic group, wherein 1 or 2 CH2 moieties of the carbocyclic group may be replaced by a carbonyl group, O or S, wherein the carbocyclic group is unsubstituted or replaced by R h replace; Ar 1 is phenyl or a 5- or 6-membered heteroaryl group, which is unsubstituted or replaced by R Ar1 Replace, where R Ar1 is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f Substitution; C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、S(=O) m R e 、-N=S(=O)-(C1-C6-alkyl)2、SO2NR b R c or S(=O) m R e ; R 6 and R 7 are identical or different H, C1-C6-alkyl, C3-C6-cycloalkyl, phenyl, -CH2-phenyl, 5- or 6-membered heteroaryl, -CH2-5- or 6-membered heteroaryl, 1,3-dioxolan-2-ylmethyl or 2-(methylamino)-2-oxo-ethyl, wherein these alkyl, cycloalkyl, phenyl and heteroaryl moieties are unsubstituted or substituted by halogen, CN, C1-C6-alkyl or C1-C6-alkoxy; Ar 2 is phenyl or a 5- or 6-membered heteroaryl group, which is unsubstituted or replaced by R Ar2 Replace, where R Ar2 is halogen, CN, -SCN, -SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyloxy-C1-C4-alkyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted by halogen, C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c ; R a , R b and R c are identical or different H, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, -C(═O)-C1-C6-alkyl, wherein these alkyl, alkenyl and cycloalkyl moieties are unsubstituted or substituted by halogen, R d is H, C1-C6-alkyl; R e is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, wherein these alkyl, cycloalkyl parts are unsubstituted or substituted by halogen or CN; R f is halogen, OH, CN, SCN, -SF5, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyloxy-C1-C4-alkyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkyloxy 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 N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

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

3. A compound of formula I according to claim 1, wherein D is a group selected from D5 to D7 parts, which are unsubstituted or substituted by 1 or 2 substituents R h Substitution, where R h As defined in claim 1 4. A compound of formula I according to claim 1, which is selected from the compounds of formulae I.1 to I.

4.

5. A compound of formula I according to any one of the preceding claims, wherein R 5 is H, C1-C6-alkyl or C1-C6-alkyl-C3-C6-cycloalkyl; R 1 is H, halogen, C1-C6-alkyl or C3-C6-cycloalkyl; R 2 is H or C1-C6-alkyl.

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

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

8. A compound of formula I according to any one of claims 1 to 7, wherein R B1 , R B2 , R B3 and R B4 are independently of one another H, halogen, CN, C1-C6-alkyl, C3-C6-cycloalkyl or C1-C6-alkoxy, where these alkyl, alkoxy and cycloalkyl moieties are unsubstituted or substituted by halogen.

9. A compound of formula I according to any one of claims 1 to claim 8, wherein Ar 1 is phenyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl or pyridinyl, which is unsubstituted or replaced by R Ar1 replace; R Ar1 is halogen, SF5, NO2, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-heterocyclyl, C3-C6-cycloalkyloxy, C2-C6-alkenyl, C2-C6-alkynyl, wherein these alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, C3-C6-heterocyclyl and cycloalkoxy moieties are unsubstituted or replaced by R f Substitution; C(=O)-OR a NR b R c , C1-C6-alkylene-CN, C(=O)-NR b R c 、C(=O)-R d 、NHS(=O) m R e 、-N=S(=O)-(C1-C6-alkyl)2、SO2NR b R c or S(=O) m R e ; R a , R b and R c are identical or different H, C1-C6-alkyl, which is unsubstituted or substituted by halogen; R d is H or C1-C6-alkyl; R e is C1-C6-alkyl or C1-C6-haloalkyl; R f is halogen, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, which is unsubstituted or substituted by halogen; m is 0, 1 or 2.

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

11. A method for combating or controlling an invertebrate pest, the method comprising contacting the pest or its food supply, habitat or breeding ground with a pesticidally effective amount of at least one compound according to any one of claims 1 to 9 or a composition according to claim 10.

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

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

14. Use of a compound of formula I according to any one of claims 1 to 9 and its agriculturally acceptable salts or a composition according to claim 10 for protecting growing plants from attack or infestation by invertebrate pests.

15. A method for treating or protecting an animal from infestation or infection by invertebrate pests, which method comprises contacting the animal with a pesticidally effective amount of at least one compound of formula I according to any one of claims 1 to 9, its stereoisomers and / or at least one veterinarily acceptable salt thereof.

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