Alkylamido-substituted annelated imidazoles and their use as insecticides.

Abstract

The present invention relates to a compound represented by the general formula (I), 1 , R 2 , R 3 and R 4 has the meaning given herein), formulations and compositions containing such compounds, and their use in controlling pests, which include arthropods and insects, in plant protection and for controlling ectoparasites of animals. [Formula 1] TIFF2024516278000078.tif38134

Description

[Technical Field]

[0001] The present invention relates to novel alkylamide-substituted annulated imidazole derivatives, formulations and compositions containing such compounds, and their use in controlling animal pests (which includes arthropods and insects) in plant protection and for controlling animal ectoparasites. [Background technology]

[0002] WO2002 / 083143 and WO2006 / 004924 disclose a number of benzimidazole compounds that are modulators of the CXCR3 receptor, useful for treating and preventing certain inflammatory and immunoregulatory disorders and diseases. Furthermore, WO2002 / 028839 discloses benzimidazoles as CRF receptor modulators. WO2011 / 123751 and WO2012 / 107465 describe certain alkylamine-substituted benzimidazoles and imidazopyridines.

[0003] Certain heteroaryl-triazole compounds are disclosed in WO2017 / 192385 for use in controlling ectoparasites in animals, and in WO2019 / 170626 and WO2019 / 215198 for use in controlling pests (which includes arthropods and insects) in the field of plant protection. Furthermore, patent applications WO2019 / 197468, WO2019 / 201835, WO2019 / 202077, WO2019 / 206799, WO2021 / 013719, WO2021 / 013720, WO2021 / 069575, WO2021 / 069567, WO2021 / 069569, WO2021 / 099303, WO2021 / 105091 , WO2021 / 165195, WO2021 / 224323 and WO2021 / 259997 disclose certain heteroaryl-triazole or heteroaryl-pyrazine compounds for use in controlling ectoparasites of animals and for controlling pests (which include arthropods and insects) in the field of plant protection. WO2020 / 002563, WO2020 / 053364, WO2020 / 053365, WO2020 / 070049, WO2020 / 079198, WO2020 / 094363, WO2020 / 169445, WO2020 / 182649, WO2020 / 188014, WO2020 / 188027, WO2020 / 19334 WO2020 / 201079, WO2020 / 201398, WO2020 / 208036, WO2021 / 037614, WO2021 / 122645 and WO2021 / 170881 describe azole-amide or pyrazine-amide compounds, all of which can be used as insecticides.

[0004] Modern plant protection products and veterinary ectoparasiticides must meet many requirements, for example, with regard to efficacy, durability, spectrum, and resistance-breaking properties. Toxicity issues and the possibility of combining with other active compounds or formulation auxiliaries play a role, in addition to the cost required to synthesize the active compound. Furthermore, resistance can also occur. Resistant parasites are becoming increasingly problematic for both livestock and companion animals, as well as for crop pests. For all these reasons, the search for new crop protection compositions or veterinary ectoparasiticides cannot be considered complete, and new compounds with improved properties, at least in individual aspects, compared with known compounds are constantly sought. It is particularly desirable to discover new pesticides and parasiticides that overcome resistance. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] WO2002 / 083143 [Patent Document 2] WO2006 / 004924 [Patent Document 3] WO2002 / 028839 [Patent Document 4] WO2011 / 123751 [Patent Document 5] WO2012 / 107465 [Patent Document 6] WO2017 / 192385 [Patent Document 7] WO2019 / 170626 [Patent Document 8] WO2019 / 215198 [Patent Document 9] WO2019 / 197468 [Patent Document 10] WO2019 / 201835 [Patent Document 11] WO2019 / 202077 [Patent Document 12] WO2019 / 206799 [Patent Document 13] WO2021 / 013719 [Patent Document 14] WO2021 / 013720 [Patent Document 15] WO2021 / 069575 [Patent Document 16] WO2021 / 069567 [Patent Document 17] WO2021 / 069569 [Patent Document 18] WO2021 / 099303 [Patent Document 19] WO2021 / 105091 [Patent Document 20] WO2021 / 165195 [Patent Document 21] WO2021 / 224323 [Patent Document 22] WO2021 / 259997 [Patent Document 23] WO2020 / 002563 [Patent Document 24] WO2020 / 053364 [Patent Document 25] WO2020 / 053365 [Patent Document 26] WO2020 / 070049 [Patent Document 27] WO2020 / 079198 [Patent Document 28] WO2020 / 094363 [Patent Document 29] WO2020 / 169445 [Patent Document 30] WO2020 / 182649 [Patent Document 31] WO2020 / 188014 [Patent Document 32] WO2020 / 188027 [Patent Document 33] WO2020 / 193341 [Patent Document 34] WO2020 / 201079 [Patent Document 35] WO2020 / 201398 [Patent Document 36] WO2020 / 208036 [Patent Document 37] WO2021 / 037614 [Patent Document 38] WO2021 / 122645 [Patent Document 39] WO2021 / 170881 Summary of the Invention [Problem to be solved by the invention]

[0006] The object of the present invention was to provide compounds that broaden the spectrum of insecticides in various respects. [Means for solving the problem]

[0007] Therefore, the present invention provides a compound of general formula (I) [ka] [In the formula (configuration 1-1): X is O or S; A1 is N or CR 5 and; A2 is N or CR 5 and; A3 is N or CR 5 and; A4 is N or CR 5 and; wherein at least one or two of A1, A2, A3, and A4 represent nitrogen (N); R 1is hydrogen; or is C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, in each case optionally substituted; or Phenyl-C1-C6 alkyl, wherein phenyl is selected from the group consisting of halogen, hydroxy, -CN, or optionally substituted by 1 to 5 substituents independently selected from the group consisting of -COOH, -CONH2, -CSNH2, -NO2, -Si(CH3)3, -SF5, -NH2, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl and C1-C3 cyanoalkylsulfonyl; or heterocyclyl-C1-C6 alkyl, wherein the heterocyclyl is selected from the group consisting of saturated and partially unsaturated 3- to 10-membered heterocyclyl, 5-membered heteroaryl, 6-membered heteroaryl, 9-membered heteroaryl, and 10-membered heteroaryl, and the heterocyclyl is selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH2, —CSNH2, —NO2, —Si(CH3)3, —SF5, —NH2, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C6 and optionally substituted by 1 to 5 substituents independently selected from the group consisting of alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, and C1-C3 cyanoalkylsulfonyl; R 2 is phenyl or a 5- or 6-membered heteroaryl, where each of these is Halogen, hydroxy, -CN, -COOH, -NO2, -NH2, -SO2NH2, -SF5; and C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C1-C6 haloalkoxy, hydroxy-C1-C6 alkyl, -CO2C1-C6 alkyl, -NH(C1-C6 alkyl), -N(C1-C6 alkyl)2, S-C1-C6 alkylsulfinimidoyl, S-C3-C6 cycloalkylsulfinimidoyl, S-C2-C6 alkenylsulfinimidoyl, S-C2-C6 alkynylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S-C1-C6 alkylsulfonimidoyl, S-C3-C6 cycloalkylsulfonimidoyl, S-C2-C6 alkenylsulfonimidoyl, S-C2-C6 alkynylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, —C(═NOC1-C6 alkyl)H, —C(═NOC1-C6 alkyl)-C1-C6 alkyl, and (C1-C6 alkyl)3-silyl; and Substructures S1-S9 (wherein the bond to the phenyl or 5- or 6-membered heteroaryl is marked with a #, and Z is CO or CS, and Y is independently selected from CO and SO): [ka] [where: R 21 is hydrogen or, in each case, optionally substituted C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, -C1-C6 alkyl-C3-C6 cycloalkyl, phenyl, heteroaryl and heterocyclyl; R 22 is hydrogen or, in each case, optionally substituted C1-C6 alkyl, C1-C6 haloalkyl, -C1-C6 alkyl-C3-C6 cycloalkyl and C3-C6 cycloalkyl; R23 are independently selected from C-C alkyl, C-C haloalkyl, C-C cycloalkyl and phenyl, each of which may be substituted; R 24 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, phenyl, heteroaryl and heterocyclyl, each of which may be substituted; Or, R 21 and R 22 together with the nitrogen atom to which they are attached, represent an optionally substituted monocyclic or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl, which may contain further heteroatoms; and 3- to 6-membered heterocyclyl or 5- to 6-membered heteroaryl, each containing one or two heteroatoms selected from the group consisting of N, O and S, wherein the 3- to 6-membered heterocyclyl substituent or the 5- to 6-membered heteroaryl substituent is selected from halogen, hydroxy, —CN, —COOH, —CONH2, —CSNH2, —NO2, —Si(CH3)3, —SF5, —NH2, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloa optionally having 1, 2, 3 or 4 substituents independently selected from the group consisting of alkyl, C1-C3 cyanoalkyl, C3-C6 cyanocycloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl and C1-C3 cyanoalkylsulfonyl; optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of: R 3is hydrogen or C1-C6 alkyl, wherein the alkyl is optionally substituted with 1 to 3 substituents selected from halogen, —CN, C3-C6-cycloalkyl and C1-C6-alkoxy; R 4 is a monocyclic heterocycle selected from the group consisting of 5-membered heteroaryl and 6-membered heteroaryl, each containing 1 or 2 heteroatoms selected from the group consisting of N, O and S, and each is Halogen, hydroxy, -CN, -COOH, -NO2, -NH2, -SF5; and C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, -C1-C6 alkyl-C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C1-C6 haloalkoxy, C1-C6 cyanoalkoxy, hydroxy-C1-C6 alkyl, -NH(C1-C6 alkyl), -NH(C1-C6 alkyl-C3-C6 cycloalkyl), -N(C1-C6 alkyl)2, -N(C1-C6 alkyl)(C1-C6 alkyl-C3-C6 cycloalkyl), -CO2C1-C6 alkyl, S-C1-C6 alkylsulfinimidoyl, S-C3-C6 cyclo alkylsulfinimidoyl, S-C2-C6 alkenylsulfinimidoyl, S-C2-C6 alkynylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S-C1-C6 alkylsulfonimidoyl, S-C3-C6 cycloalkylsulfonimidoyl, S-C2-C6 alkenylsulfonimidoyl, S-C2-C6 alkynylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, —C(═NOC1-C6 alkyl)H and —C(═NOC1-C6 alkyl)-C1-C6 alkyl; and 3-6 membered heterocyclyl containing one or two heteroatoms selected from the group consisting of N, O and S, wherein the 3-6 membered heterocyclyl substituents are halogen, hydroxy, -CN, -COOH, -CONH2, -CSNH2, -NO2, -Si(CH3)3, -SF5, -NH2, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C3 cyano optionally bearing 1, 2, 3, or 4 substituents independently selected from the group consisting of alkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, and C1-C3 cyanoalkylsulfonyl; and The following substructures S10-S18 (wherein the bonds to the 5-membered heteroaryl and 6-membered heteroaryl are marked with #, and Z is CO or CS, and Y is independently selected from CO and SO): [ka] [where: R 41 is hydrogen or, in each case, optionally substituted C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, -C1-C6 alkyl-C3-C6 cycloalkyl, phenyl, heteroaryl and heterocyclyl; R 42 is hydrogen or C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, -C1-C6 alkyl-C3-C6 cycloalkyl or C3-C6 cycloalkyl, in each case optionally substituted; R 43are independently selected from C-C alkyl, C-C haloalkyl, C-C cycloalkyl and phenyl, each of which may be substituted; R 44 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, phenyl, heteroaryl and heterocyclyl, each of which may be substituted; Or, R 41 and R 42 together with the nitrogen atom to which they are attached, represent an optionally substituted monocyclic or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl, which may contain further heteroatoms; optionally substituted with 1, 2, 3, or 4 substituents independently selected from the group consisting of: R 5 is hydrogen, halogen, -CN, -NH2 or, in each case, optionally substituted C1-C3-alkyl, C1-C3-haloalkyl, C1-C3 cyanoalkyl, C3-C4-cycloalkyl, C3-C4 halocycloalkyl, C3-C6 cyanocycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, -CO2(C1-C3 alkyl), -CH-(C1-C3 alkoxy)2, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl), -NHCO-C1-C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alkyl, -NH(C1-C3 alkyl), -N(C1-C3 alkyl)2, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylthio, C3-C6 cycloalkylsulfinyl or C3-C6 cycloalkylsulfonyl. and salts and N-oxides thereof.

[0008] Any reference to a compound of formula (I) described anywhere in this specification also includes all diastereomers or enantiomers and E / Z isomers that may exist, as well as salts and N-oxides of compounds of formula (I) and their use for controlling pests.

[0009] The compounds of formula (I) described anywhere in this specification can exist in stereoisomeric forms, i.e. in the form of geometric and / or optical isomers or in the form of isomeric mixtures in various compositions, depending on the type of their substituents. Even if generally only compounds of formula (I) are discussed herein, the present invention provides both the pure stereoisomers and any desired mixtures of these isomers.

[0010] However, according to the invention, the optically active stereoisomeric forms of the compounds of formula (I) and their salts are preferably used.

[0011] The invention therefore relates both to the pure enantiomers and diastereomers and to their mixtures.

[0012] Where appropriate, compounds of formula (I) may exist in various polymorphic forms or as mixtures of various polymorphic forms. Both pure polymorphs and polymorphic mixtures are provided by the present invention and may be used in accordance with the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0013] Preferred is (Configuration 2-1), formula (I) [wherein, X is O or S; A1 is N or CR 5 and; A2 is N or CR 5 and; A3 is N or CR 5 and; A4 is N or CR 5 and; wherein one or two of A1, A2, A3, and A4 represent nitrogen (N); R 1 is hydrogen; or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, each of which is optionally substituted with a group selected from halogen, —CN, C1-C3 alkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, and C1-C3 alkylsulfonyl; or C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl; or phenyl-C1-C3 alkyl, wherein phenyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, -CN, -NO2, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, and C1-C3 haloalkylsulfonyl; or heterocyclyl-C1-C3 alkyl, wherein the heterocyclyl is selected from the group consisting of saturated or partially unsaturated 3- to 10-membered heterocyclyl, 5-membered heteroaryl, 6-membered heteroaryl, 9-membered heteroaryl, and 10-membered heteroaryl, and the heterocyclyl is optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, -CN, -NO2, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, and C1-C3 haloalkylsulfonyl; R 2is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine, pyridazine, thiophene, and pyrazole, wherein each of these is · Halogen, hydroxy, -CN, -COOH, -NO2, -NH2, -SO2NH2, -SF5; C1-C6 alkyl optionally substituted with -CN, -OH or C3-C6 cycloalkyl; C2-C6 alkenyl optionally substituted with halogen and -CN; C2-C6 alkynyl optionally substituted with halogen and -CN; C3-C6 cycloalkyl optionally substituted with halogen, -CN, C1-C3 alkyl or C1-C3 haloalkyl; C1-C6 haloalkyl optionally substituted with -CN or C1-C6 alkoxy; C1-C6 alkoxy optionally substituted with -CN; C3-C6 cycloalkoxy optionally substituted with halogen or -CN; C1-C6 haloalkoxy, -CO2C1-C6 alkyl, -NH(C1-C6 alkyl), -N(C1-C6 alkyl)2, S-C1-C6 alkylsulfinimidoyl, S -C3-C6 cycloalkylsulfinimidoyl, S-C2-C6 alkenylsulfinimidoyl, S-C2-C6 alkynylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S-C1-C6 alkylsulfonimidoyl, S-C3-C6 cycloalkylsulfonimidoyl, S-C2-C6 alkenylsulfonimidoyl, S-C2-C6 alkynylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, -C(=NOC1-C6 alkyl)H, -C(=NOC1-C6 alkyl)-C1-C6 alkyl and (C1-C6 alkyl)3-silyl; and Substructures S1-S9 (wherein the bonds to phenyl, pyridine, pyrimidine, pyrazine, pyridazine, thiophene and pyrazole are marked with #, and Z is CO or CS, and Y is independently selected from CO and SO): [ka] [where: R 21 is hydrogen, C1-C6 alkyl, C1-C6 cyanoalkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, -C1-C6 alkyl-C3-C6 cycloalkyl, phenyl, heteroaryl, or heterocyclyl, wherein phenyl, heteroaryl, and heterocyclyl are each optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, -CN, -NO2, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, and C1-C3 haloalkylsulfonyl; R 22 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, -C1-C6 alkyl-C3-C6 cycloalkyl or C3-C6 cycloalkyl; R 23 are independently selected from C-C alkyl, C-C haloalkyl, C-C cycloalkyl and phenyl, each of which may be substituted; R 24 is C1-C6 alkyl, C1-C6 cyanoalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, phenyl, heteroaryl, and heterocyclyl, wherein phenyl, heteroaryl, and heterocyclyl are each optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, -CN, -NO2, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, and C1-C3 haloalkylsulfonyl; Or, R 21 and R22 together with the nitrogen atom to which they are attached, represent a monocyclic or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl (wherein the heterocyclyl may contain additional heteroatoms), and the monocyclic or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl is each optionally substituted by 1 to 4 substituents independently selected from the group consisting of halogen, —CN, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl and C1-C3 haloalkylsulfonyl; and a 3- to 6-membered heterocyclyl or a 5- to 6-membered heteroaryl, each containing one or two heteroatoms selected from the group consisting of N, O and S, wherein the 3- to 6-membered heterocyclyl substituent or the 5- to 6-membered heteroaryl substituent is selected from halogen, hydroxy, —CN, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C6 cyanoalkyl, optionally having 1, 2, 3, or 4 substituents independently selected from the group consisting of cycloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, and C1-C3 cyanoalkylsulfonyl; optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of: R 3is hydrogen or C1-C6 alkyl, wherein the alkyl is optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, —CN, C3-C6-cycloalkyl and C1-C6-alkoxy; R 4 is a monocyclic heterocycle selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine and thiazole, wherein each of · Halogen, hydroxy, -CN, -COOH, -NO2, -NH2, -SF5; C1-C6 alkyl, C1-C6 cyanoalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, C3-C6 halocycloalkyl, -C1-C6 alkyl-C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C1-C6 haloalkoxy, C1-C6 cyanoalkoxy, hydroxy-C1-C6 alkyl, -NH(C1-C6 alkyl), -NH(C1-C6 alkyl-C3-C6 cycloalkyl), -N(C1-C6 alkyl)2, -N(C1-C6 alkyl)(C1-C6 alkyl-C3-C6 cycloalkyl), -CO2C1-C6 alkyl, S-C1-C6 alkylsulfinimide yl, S-C3-C6 cycloalkylsulfinimidoyl, S-C2-C6 alkenylsulfinimidoyl, S-C2-C6 alkynylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S-C1-C6 alkylsulfonimidoyl, S-C3-C6 cycloalkylsulfonimidoyl, S-C2-C6 alkenylsulfonimidoyl, S-C2-C6 alkynylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, and —C(═NOC1-C6 alkyl)H, —C(═NOC1-C6 alkyl)-C1-C6 alkyl; and The following substructures S10-S18 (wherein the bonds to the 5-membered heteroaryl and 6-membered heteroaryl are marked with #, and Z is CO or CS, and Y is independently selected from CO and SO): [ka] [where: R 41 is hydrogen, C1-C6 alkyl, C1-C6 cyanoalkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, -C1-C6 alkyl-C3-C6 cycloalkyl, phenyl, heteroaryl, or heterocyclyl, wherein phenyl, heteroaryl, and heterocyclyl are each optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, -CN, -NO2, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, and C1-C3 haloalkylsulfonyl; R 42 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, -C1-C6 alkyl-C3-C6 cycloalkyl or C3-C6 cycloalkyl; R 43 are independently selected from C-C alkyl, C-C haloalkyl, C-C cycloalkyl and phenyl, each of which may be substituted; R 44is C1-C6 alkyl, C1-C6 cyanoalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, phenyl, heteroaryl, or heterocyclyl, wherein phenyl, heteroaryl, and heterocyclyl are each optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, -CN, -NO2, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, and C1-C3 haloalkylsulfonyl; Or, R 41 and R 42 together with the nitrogen atom to which they are attached, represent a monocyclic or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl (wherein the heterocyclyl may contain additional heteroatoms), and the monocyclic or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl is each optionally substituted by 1 to 4 substituents independently selected from the group consisting of halogen, —CN, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, and C1-C3 haloalkylsulfonyl; optionally substituted with one or two substituents independently selected from the group consisting of: R 5is hydrogen, halogen, -CN, -NH2, C1-C3-alkyl, C1-C3-haloalkyl, C1-C3 cyanoalkyl, C3-C4-cycloalkyl, C3-C4 halocycloalkyl, C3-C6 cyanocycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, -NH(C1-C3 alkyl), -N(C1-C3 alkyl)2, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylthio, C3-C6 cycloalkylsulfinyl or C3-C6 cycloalkylsulfonyl. and salts and N-oxides thereof.

[0014] Even more preferable is (Configuration 3-1), formula (I) [wherein, X is O or S; A1 is N; A2 is N or CR 5 and; A3 is N or CR 5 and; A4 is N or CR 5 or A1 is N or CR 5 and; A2 is N; A3 is N or CR 5 and; A4 is N or CR 5 or A1 is N or CR 5 and; A2 is N or CR 5 and; A3 is N; A4 is N or CR 5 or A1 is N or CR 5 and; A2 is N or CR 5 and; A3 is N or CR 5 and; A4 is N; or A1 is N; A2 is N or CR 5 and; A3 is N or CR 5 and; A4 is N; R 1 is hydrogen, C1-C6 alkyl, C1-C3 cyanoalkyl, C1-C3 haloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C3 alkoxyC1-C3 alkyl, C1-C3 alkylthioC1-C3 alkyl, C1-C3 alkylsulfinylC1-C3 alkyl or C1-C3 alkylsulfonylC1-C3 alkyl; R 2is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine, pyridazine and pyrazole, wherein each of these is selected from the group consisting of halogen, hydroxy, -CN, -COOH, -CONH2, -NO2, -NH2, -SO2NH2, -SF5, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cyanocycloalkyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkoxy, C1-C3 cycloalkyl, C1-C3 halocycloalkyl, C3-C6 cyanocycloalkyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkoxy, C1-C3 cycloalkyl, C1-C3 cycloalkyl, C1-C3 cycloalkyl, C1-C3 cycloalkyl, C1-C3 cycloalkyl, C1-C3 cycloalkyl, C1-C3 cycloalkyl, C1-C3 cycloalkyl, C1-C3 cycloalkyl, C1-C3 cycloalkyl, C1-C3 cycloalkyl, C1-C3 cycloalkyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 cycloalkyl ... C3-C6 cycloalkylsulfonyl, C3-C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkoxy, hydroxy-C1-C4 alkyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, NHCO-C3-C6 cycloalkyl, -NHSO2(C1-C4 alkyl), -N(C1-C4 alkyl)CO-C1-C4 alkyl , -N(C1-C4 alkyl)CO-C3-C6 cycloalkyl, -N(C1-C4 alkyl)SO2C1-C4 alkyl, -N(SO2C1-C4 alkyl)2, -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl), -CONH(C3-C6 cycloalkyl), -CONH-phenyl, -CON(C1-C4 alkyl)2, -CON(C1-C4 alkyl)(C3-C6 cycloalkyl), -CON(C1-C4 alkyl)-phenyl, -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)- 1 independently selected from the group consisting of C1-C4 alkyl, (C1-C4 alkyl)3-silyl, -SONH(C1-C4 alkyl), phenylsulfonyl, and 3- to 6-membered heterocyclyl containing 1 or 2 heteroatoms selected from the group consisting of N, O, and S (wherein the phenyl group and the 3- to 6-membered heterocyclyl substituent in the above substituents can have 1, 2, or 3 substituents independently selected from the group consisting of halogen, -CN, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy);optionally substituted with 2 or 3 substituents; R 3 is hydrogen, C1-C6 alkyl, wherein the alkyl is optionally substituted with 1 to 3 substituents selected from halogen, C3-C6-cycloalkyl or C1-C6-alkoxy; R 4 is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine and thiazole, each of which is optionally substituted with one or two substituents independently selected from the group consisting of halogen, —CN, —COOH, —NO, —NH, —SF, C-C alkyl, C-C cycloalkyl, C-C alkyl-C-C cycloalkyl, C-C haloalkyl, C-C cyanoalkyl, C-C halocycloalkyl, C-C cyanocycloalkyl, C-C alkoxy, C-C haloalkoxy, C-C cyanoalkoxy and —COC-C alkyl; Or, R 4 is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine and thiazole; wherein each of these is optionally substituted with one substituent selected from the group consisting of halogen, -CN, -COOH, -NO2, -NH2, -SF5, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C4 alkyl-C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C6 halocycloalkyl, C3-C6 cyanocycloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy and -CO2C1-C6 alkyl; and wherein these are further subdivided into the following substructures S10-S18, respectively, where the bonds to the pyridine, pyrimidine, pyrazine, pyridazine and thiazole are marked with #, and Z is CO or CS, and Y is independently selected from CO and SO: [ka] [where: R 41is hydrogen, C1-C4 alkyl, C1-C3 cyanoalkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl or -C1-C3 alkyl-C3-C6 cycloalkyl; R 42 is hydrogen, C1-C4 alkyl, C1-C3 cyanoalkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl or -C1-C3 alkyl-C3-C6 cycloalkyl; R 43 is C1-C4 alkyl, C1-C3 haloalkyl or C3-C6 cycloalkyl; R 44 is C1-C4 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C3 haloalkyl or C3-C6 cycloalkyl; Or, R 41 and R 42 together with the nitrogen atom to which they are attached, represent a monocyclic or polycyclic 5- to 6-membered saturated or unsaturated heterocyclyl (wherein the heterocyclyl may contain additional heteroatoms), and the monocyclic or polycyclic 5- to 6-membered saturated or unsaturated heterocyclyl is each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, —CN, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, and C1-C3 haloalkylsulfonyl; and is substituted with one substituent selected from the group consisting of: R 5 is hydrogen, halogen, —CN, C1-C6-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, C1-C3-alkoxy or C1-C3-haloalkoxy. and salts and N-oxides thereof.

[0015] Particularly preferred is (Configuration 4-1), formula (I) [wherein, X is O or S; A1 is N; A2 is N or CR 5 and; A3 is N or CR 5 and; A4 is N or CR 5 or A1 is N or CR 5 and; A2 is N; A3 is N or CR 5 and; A4 is N or CR 5 or A1 is N or CR 5 and; A2 is N or CR 5 and; A3 is N; A4 is N or CR 5 or A1 is N or CR 5 and; A2 is N or CR 5 and; A3 is N or CR 5 and; A4 is N; or A1 is N; A2 is N or CR 5 and; A3 is N or CR 5 and; A4 is N; R 1 is hydrogen, methyl, ethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, methoxyethyl, methylthioethyl, methylsulfinylethyl or methylsulfonylethyl; R 2 gives the substructures Q1, Q2 and Q3 (where the bond to the C=X-group is marked with a #): [ka] [where: R 25is hydroxy, -CN, -NH2, -SO2NH2, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cyanocycloalkyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl , C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkoxy, hydroxy-C1-C4 alkyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, NHCO-C3-C6 cycloalkyl, -NHSO2(C1-C4 alkyl), -N(C1-C4 alkyl)CO-C1-C4 alkyl, -N(C1-C4 alkyl)CO-C3-C6 cycloalkyl(cyclolkyl) ), -N(C1-C4 alkyl)SO2C1-C4 alkyl, -N(SO2C1-C4 alkyl)2, -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl), -CONH(C3-C6 cycloalkyl), -CONH-phenyl, -CON(C1-C4 alkyl)2, -CON(C1-C4 alkyl)(C3-C6 cycloalkyl), -CON(C1-C4 alkyl)-phenyl, -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alkyl, (C1-C -4 alkyl)3-silyl, -SONH(C1-C4 alkyl), phenylsulfonyl, or a 3- to 6-membered heterocyclyl containing one or two heteroatoms selected from the group consisting of N, O, and S, wherein the phenyl group and the 3- to 6-membered heterocyclyl substituent in the above substituents can have one, two, or three substituents independently selected from the group consisting of halogen, -CN, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy; and R 26is hydrogen, halogen, -CN, -COOH, -CONH2, -NO2, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C3-C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C3-C6 cycloalkyl, C1-C3 cyanoalkyl or C3-C6 cyanocycloalkyl; R 27 is hydrogen or C1-C4 alkyl] Selected from; R 3 is methyl; R 4 is selected from the group consisting of pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrazin-3-yl and 1,3-thiazol-2-yl, each of which is optionally substituted with one substituent independently selected from the group consisting of fluorine, chlorine, bromine, —CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, difluoroethoxy, methoxycarbonyl and ethoxycarbonyl; or The following structure S13 (wherein the bonds to the pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrazin-3-yl and 1,3-thiazol-2-yl are marked with # and Z is CO): [ka] [where: R 41 is hydrogen, methyl, ethyl, cyclopropylmethyl, cyanomethyl, cyclopropyl, difluoroethyl or trifluoroethyl; R 42is hydrogen, methyl, ethyl, cyclopropylmethyl, cyanomethyl, cyclopropyl, difluoroethyl or trifluoroethyl; Or, R 41 and R 42 together with the nitrogen atom to which they are attached represent morpholine optionally substituted with 1 to 4 methyl groups. may be substituted with; R 5 is hydrogen, fluorine, chlorine, bromine, iodine, —CN, methyl, ethyl, isopropyl, difluoromethyl, trifluoromethyl, cyclopropyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy. and salts and N-oxides thereof.

[0016] Very particularly preferred are (Configuration 5-1), formula (I) [wherein, X is O; A1 is N; A2 is CR 5 and; A3 is CR 5 and; A4 is CR 5 and; R 1 is hydrogen; R 2 is selected from the group consisting of 3-chloro-5-(trifluoromethoxy)phenyl, 3,5-bis-(trifluoromethyl)phenyl, 3,5-bis-(trifluoromethoxy)phenyl, 3-cyano-5-(1-cyano-1-methyl-ethyl)phenyl, 3-(1-cyano-1-methyl-ethyl)-5-(trifluoromethoxy)phenyl, 3-cyclopropyl-5-(trifluoromethoxy)phenyl, 3-cyano-5-(1-cyanocyclopropyl)phenyl, 3-(1-cyanocyclopropyl)-5-(trifluoromethoxy)phenyl, (3-chloro-5-methylsulfonylphenyl), 3-methylsulfonyl-5-(trifluoromethoxy)phenyl and 5-(difluoromethyl)-1-methyl-pyrazol-3-yl; R 3is methyl; R 4 is selected from the group consisting of 5-chloro-pyridin-2-yl, 5-cyano-pyridin-2-yl and 5-methoxycarbonyl-2-pyridyl; R 5 is selected from hydrogen and methyl. and salts and N-oxides thereof.

[0017] Likewise very particularly preferred are (Configuration 5-2), formula (I) [wherein, X is O; A1 is N; A2 is CR 5 and; A3 is CR 5 and; A4 is CR 5 or A1 is CR 5 and; A2 is CR 5 and; A3 is N; A4 is CR 5 or A1 is CR 5 and; A2 is CR 5 and; A3 is CR 5 and; A4 is N; R 1 is hydrogen; R 2are 3-chloro-5-(trifluoromethoxy)phenyl, 3-bromo-5-(trifluoromethoxy)phenyl, 3-cyano-5-(trifluoromethoxy)phenyl, 3,5-bis(difluoromethyl)phenyl, 3,5-bis-(trifluoromethyl)phenyl, 3,5-bis(difluoromethoxy)phenyl, 3,5-bis-(trifluoromethoxy)phenyl, 3-(1,1-difluoroethyl)-5-(trifluoromethoxy)phenyl, 3-cyclopropyl-5-(trifluoromethoxy)phenyl, 3-cyano-5-(1-cyano-1-methyl-ethyl)phenyl, 3-(1-cyano-1-methyl-ethyl)phenyl, 3-(1-chloro-ethyl)-5-(trifluoromethoxy)phenyl, 3-cyclopropyl-5-(trifluoromethoxy)phenyl, 3-cyano-5-(1-cyanocyclopropyl)phenyl, 3-(1-cyanocyclopropyl)-5-(trifluoromethoxy)phenyl, (3-chloro-5-methylsulfonylphenyl), 3-methylsulfonyl-5-(trifluoromethoxy)phenyl, 3-(difluoromethylsulfonyl)-5-(trifluoromethoxy)phenyl, 3,5-bis(difluoromethylsulfonyl)phenyl and 5-(difluoromethyl)-1-methyl-pyrazol-3-yl; R 3 is methyl; R 4 is selected from the group consisting of pyrimidin-2-yl, 5-chloro-pyridin-2-yl, 5-cyano-pyridin-2-yl, 5-methoxycarbonyl-2-pyridyl, 5-(aminocarbonyl)pyridin-2-yl, 5-(methylcarbamoyl)pyridin-2-yl and 5-(dimethylaminocarbonyl)pyridin-2-yl; R 5 is selected from hydrogen, fluorine and methyl. and salts and N-oxides thereof.

[0018] In a further preferred embodiment, the present invention provides a compound of formula (Ii) [ka] [In the formula, the structural element R 1, R 2 , R 3 , R 4 and R 5 has the meaning given in structure (1-1) or the meaning given in structure (2-1) or the meaning given in structure (3-1) or the meaning given in structure (4-1) or the meaning given in structure (5-1) or the meaning given in structure (5-2) The present invention relates to a compound represented by the formula:

[0019] In a further preferred embodiment, the present invention provides a compound of formula (I-ii) [ka] [In the formula, the structural element R 1 , R 2 , R 3 , R 4 and R 5 has the meaning given in structure (1-1) or the meaning given in structure (2-1) or the meaning given in structure (3-1) or the meaning given in structure (4-1) or the meaning given in structure (5-1) or the meaning given in structure (5-2) The present invention relates to a compound represented by the formula:

[0020] In a further preferred embodiment, the present invention provides a compound of formula (I-iii) [ka] [In the formula, the structural element R 1 , R 2 , R 3 , R 4 and R 5 has the meaning given in structure (1-1), or the meaning given in structure (2-1), or the meaning given in structure (3-1), or the meaning given in structure (4-1), or the meaning given in structure (5-1), or the meaning given in structure (5-2).

[0021] In a further preferred embodiment, the present invention provides a compound of formula (I-iv) [ka] [In the formula, the structural element R 1 , R 2 , R 3 , R 4 and R 5 has the meaning given in structure (1-1) or the meaning given in structure (2-1) or the meaning given in structure (3-1) or the meaning given in structure (4-1) or the meaning given in structure (5-1) or the meaning given in structure (5-2) The present invention relates to a compound represented by the formula:

[0022] In a further preferred embodiment, the present invention provides a compound of formula (Iv) [ka] [In the formula, the structural element R 1 , R 2 , R 3 , R 4 and R 5 has the meaning given in structure (1-1) or the meaning given in structure (2-1) or the meaning given in structure (3-1) or the meaning given in structure (4-1) or the meaning given in structure (5-1) or the meaning given in structure (5-2) The present invention relates to a compound represented by the formula:

[0023] In a further preferred embodiment, the present invention provides a compound of formula (I-vi) [ka] [In the formula, the structural element R 1 , R 2 , R 3 , R 4 and R 5has the meaning given in structure (1-1), or the meaning given in structure (2-1), or the meaning given in structure (3-1), or the meaning given in structure (4-1), or the meaning given in structure (5-1), or the meaning given in structure (5-2).

[0024] In a further preferred embodiment, the present invention provides a compound of formula (I-vii) [ka] [In the formula, the structural element R 1 , R 2 , R 3 , R 4 and R 5 has the meaning given in structure (1-1) or the meaning given in structure (2-1) or the meaning given in structure (3-1) or the meaning given in structure (4-1) or the meaning given in structure (5-1) or the meaning given in structure (5-2) The present invention relates to a compound represented by the formula:

[0025] In a further preferred embodiment, the present invention provides a compound of formula (Ia) [ka] [In the formula, structural elements A1, A2, A3, A4, R 1 , R 2 , R 3 , R 4 and X has the meaning given in structure (1-1) or the meaning given in structure (2-1) or the meaning given in structure (3-1) or the meaning given in structure (4-1) or the meaning given in structure (5-1) or the meaning given in structure (5-2). The present invention relates to a compound represented by the formula:

[0026] In a further preferred embodiment, the present invention provides a compound of formula (Ib) [ka] [In the formula, structural elements A1, A2, A3, A4, R 1 , R 2 , R 3 , R 4 and X has the meaning given in structure (1-1), or the meaning given in structure (2-1), or the meaning given in structure (3-1), or the meaning given in structure (4-1), or the meaning given in structure (5-1), or the meaning given in structure (5-2).

[0027] In particular, the present invention includes intermediate compounds INT-1 to INT-7, including their salts in the case of amines and acids, and the free amine in the case of amine hydrochlorides or triflates (see Table 2): INT-1: 6-[2-[(1S)-1-aminoethyl]imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile hydrochloride INT-2: 1-[3-(5-chloro-2-pyridyl)imidazo[4,5-b]pyridin-2-yl]ethanamine; 2,2,2-trifluoroacetic acid INT-3: 6-[2-(1-aminoethyl)-7-methyl-imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile hydrochloride INT-4: Methyl 6-[2-(1-aminoethyl)imidazo[4,5-b]pyridin-3-yl]pyridine-3-carboxylate hydrochloride INT-5: 6-[2-[1-aminoethyl]-6-methyl-imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile hydrochloride INT-6: 6-[2-[1-aminoethyl]-5-methyl-imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile hydrochloride INT-7: 1-[1-(5-chloro-2-pyridyl)imidazo[4,5-c]pyridin-2-yl]ethanamine hydrochloride INT-8: 1-[1-(5-chloropyridin-2-yl)-1H-imidazo[4,5-b]pyridin-2-yl]ethanamine trifluoroacetate.

[0028] definition Those skilled in the art will recognize that the expressions "a" or "an," when used in this application, can mean "one," "one or more," or "at least one," depending on the context, even if not explicitly stated otherwise.

[0029] For all structures described herein including ring systems and groups, adjacent atoms must not be -OO- or -OS-.

[0030] Structures with variable numbers of possible carbon atoms (C atoms) are, for the purposes of more specific specification, referred to in this application as C 炭素原子の下限 -C 炭素原子の上限 Structure (C LL -C UL For example, an alkyl group can be composed of 3 to 10 carbon atoms, in which case it can be described as a C3-C 10 -alkyl. Ring structures composed of carbon atoms and heteroatoms may be described as "LL-UL membered" structures. An example of a six-membered ring structure is toluene (a six-membered ring structure substituted with methyl groups).

[0031] Collective terms for substituents, e.g., C LL -C UL -Alkyl may be a complex substituent, e.g., C LL -C UL -Cycloalkyl-C LL -C UL - When it is at the end of an alkyl, it is the first component of the compound substituent, e.g., C LL -C UL -cycloalkyl may be, similarly or differently, and independently, the latter substituents, e.g., C LL -C UL All collective terms used in this application with respect to chemical groups, ring systems and cyclic groups are defined as "CLL -C UL " or "LL~UL member" can be added to make it more specific.

[0032] In the definitions of the symbols given in the formula above, collective terms have been used which generally represent the following substituents:

[0033] Halogen relates to elements of main group 7, preferably fluorine, chlorine, bromine and iodine, more preferably fluorine, chlorine and bromine, even more preferably fluorine and chlorine.

[0034] Examples of heteroatoms are N, O, S, P, B, Si. Preferably, the term "heteroatom" relates to N, S and O.

[0035] According to the present invention, "alkyl", alone or as part of a chemical group, represents a straight or branched chain hydrocarbon, preferably having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylpropyl, 1,3-dimethylbutyl, 1,4-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl and 2-ethylbutyl. Alkyl having 1 to 4 carbon atoms is also preferred, such as, inter alia, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl. Alkyl according to the invention can be substituted with one or more identical or different radicals.

[0036] According to the present invention, "alkenyl" alone or as part of a chemical group preferably denotes a straight or branched chain hydrocarbon having 2 to 6 carbon atoms and at least one double bond, such as vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 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-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-3-butenyl, 1-methyl-2-pentenyl, 4-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3- Dimethyl-2-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, and 1-ethyl-2-methyl-2-propenyl are also preferred. Alkenyls having 2 to 4 carbon atoms, such as, inter alia, 2-propenyl, 2-butenyl, or 1-methyl-2-propenyl, are also preferred. Alkenyls according to the present invention may be substituted with one or more identical or different radicals.

[0037] According to the present invention, "alkynyl" alone or as part of a chemical group preferably denotes a straight or branched chain hydrocarbon having 2 to 6 carbon atoms and at least one triple bond, such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 6-hexynyl, 7-hexynyl, 8-hexynyl, 9-hexynyl, 10-hexynyl, 11-hexynyl, 12-hexynyl, 13-hexynyl, 14-hexynyl, 15-hexynyl, 16-hexynyl, 17-hexynyl, 18-hexynyl, 19-hexynyl, 20-hexynyl, 21-hexynyl, 22-hexynyl, 23-hexynyl, 24-hexynyl, 25-hexynyl, 26-hexynyl, 27-hexynyl, 28-hexynyl, 29-hexynyl, 29-hexynyl, 26-hexynyl, 28-hexynyl, 29-hexynyl, 29-hexynyl, 29-hexynyl, 30-hexynyl, 31-hexynyl, 32-hexynyl, 33-hexynyl, 34-hexynyl, 35-hexynyl, 36-hexynyl, 37-hexynyl, 38-hexynyl, 39-hexynyl, 39-hexynyl, 39- Alkynyl groups include ethynyl, 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-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, and 2,5-hexazinyl. Alkynyl groups having 2 to 4 carbon atoms are also preferred, such as, inter alia, ethynyl, 2-propynyl, or 2-butynyl-2-propenyl. Alkynyl groups according to the present invention can be substituted with one or more identical or different radicals.

[0038] According to the present invention, "cycloalkyl" alone or as part of a chemical group denotes a monocyclic, bicyclic or tricyclic hydrocarbon, preferably having 3 to 10 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl or adamantyl. Cycloalkyls having 3, 4, 5, 6 or 7 carbon atoms are also preferred, such as, inter alia, cyclopropyl or cyclobutyl. Cycloalkyls according to the present invention may be substituted with one or more identical or different radicals.

[0039] According to the present invention, "alkylcycloalkyl" denotes a monocyclic, bicyclic, or tricyclic alkylcycloalkyl, preferably having 4 to 10 or 4 to 7 carbon atoms, such as methylcyclopropyl, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopentyl, and 4-methylcyclohexyl. Alkylcycloalkyls having 4, 5, or 7 carbon atoms, such as, inter alia, ethylcyclopropyl or 4-methylcyclohexyl, are also preferred. Alkylcycloalkyls according to the present invention may be substituted with one or more identical or different radicals.

[0040] According to the present invention, "cycloalkylalkyl" denotes a monocyclic, bicyclic or tricyclic cycloalkylalkyl, preferably having 4 to 10 or 4 to 7 carbon atoms, such as cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and cyclopentylethyl. Cycloalkylalkyl having 4, 5 or 7 carbon atoms, such as, inter alia, cyclopropylmethyl or cyclobutylmethyl, is also preferred. Cycloalkylalkyl according to the present invention may be substituted with one or more identical or different radicals.

[0041] According to the present invention, "hydroxyalkyl" denotes a straight-chain or branched alcohol, preferably having 1 to 6 carbon atoms, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, s-butanol and t-butanol. Hydroxyalkyl groups having 1 to 4 carbon atoms are also preferred. Hydroxyalkyl groups according to the present invention can be substituted with one or more identical or different radicals.

[0042] According to the present invention, "alkoxy" denotes straight-chain or branched O-alkyl, preferably having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy and t-butoxy. Alkoxy groups having 1 to 4 carbon atoms are also preferred. Alkoxy groups according to the present invention can be substituted with one or more identical or different radicals.

[0043] According to the present invention, "alkylthio" or "alkylsulfanyl" denotes a straight-chain or branched S-alkyl group, preferably having 1 to 6 carbon atoms, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio and t-butylthio. Alkylthio groups having 1 to 4 carbon atoms are also preferred. Alkylthio groups according to the present invention may be substituted with one or more identical or different radicals.

[0044] According to the present invention, "alkylsulfinyl" preferably represents a straight-chain or branched alkylsulfinyl having 1 to 6 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, s-butylsulfinyl, and t-butylsulfinyl. Alkylsulfinyl groups having 1 to 4 carbon atoms are also preferred. Alkylsulfinyl groups according to the present invention can be substituted with one or more identical or different radicals and include both enantiomers.

[0045] According to the present invention, "alkylsulfonyl" preferably denotes a straight-chain or branched alkylsulfonyl having 1 to 6 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, s-butylsulfonyl and t-butylsulfonyl. Alkylsulfonyl groups having 1 to 4 carbon atoms are also preferred. Alkylsulfonyl groups according to the present invention may be substituted with one or more identical or different radicals.

[0046] According to the present invention, "cycloalkylthio" or "cycloalkylsulfanyl" denotes -S-cycloalkyl, preferably having 3 to 6 carbon atoms, such as cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio. Cycloalkylthio groups having 3 to 5 carbon atoms are also preferred. Cycloalkylthio groups according to the present invention can be substituted with one or more identical or different radicals.

[0047] According to the present invention, "cycloalkylsulfinyl" preferably denotes -S(O)-cycloalkyl having 3 to 6 carbon atoms, such as cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl. Cycloalkylsulfinyl groups having 3 to 5 carbon atoms are also preferred. Cycloalkylsulfinyl groups according to the present invention can be substituted with one or more identical or different radicals and include both enantiomers.

[0048] According to the present invention, "cycloalkylsulfonyl" denotes -SO2-cycloalkyl, preferably having 3 to 6 carbon atoms, such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl. Cycloalkylsulfonyl groups having 3 to 5 carbon atoms are also preferred. Cycloalkylsulfonyl groups according to the present invention can be substituted with one or more identical or different radicals.

[0049] According to the present invention, "phenylthio" or "phenylsulfanyl" denotes -S-phenyl, e.g., phenylthio. A phenylthio group according to the present invention may be substituted with one or more identical or different radicals.

[0050] According to the present invention, "phenylsulfinyl" denotes -S(O)-phenyl, e.g., phenylsulfinyl. A phenylsulfinyl group according to the present invention can be substituted with one or more identical or different radicals and includes both enantiomers.

[0051] According to the present invention, "phenylsulfonyl" denotes -SO2-phenyl, e.g., phenylsulfonyl. The phenylsulfonyl group according to the present invention may be substituted with one or more identical or different radicals.

[0052] According to the present invention, "alkylcarbonyl" denotes a straight or branched alkyl-C(=O) having preferably 2 to 7 carbon atoms, such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl and t-butylcarbonyl. Alkylcarbonyl having 1 to 4 carbon atoms is also preferred. Alkylcarbonyl according to the present invention can be substituted with one or more identical or different radicals.

[0053] According to the present invention, "alkoxycarbonyl" alone or as a component of a chemical group denotes a straight-chain or branched alkoxycarbonyl, preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkoxy moiety, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl and t-butoxycarbonyl. The alkoxycarbonyl group according to the present invention can be substituted with one or more identical or different radicals.

[0054] According to the present invention, "alkylaminocarbonyl" represents a straight-chain or branched alkylaminocarbonyl group, preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, s-butylaminocarbonyl, and t-butylaminocarbonyl. The alkylaminocarbonyl group according to the present invention may be substituted with one or more identical or different radicals.

[0055] According to the present invention, "N,N-dialkylaminocarbonyl" represents a straight-chain or branched N,N-dialkylaminocarbonyl, preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di(n-propylamino)carbonyl, N,N-di(isopropylamino)carbonyl and N,N-di-(s-butylamino)carbonyl. The N,N-dialkylaminocarbonyl group according to the present invention can be substituted with one or more identical or different radicals.

[0056] According to the present invention, "aryl" denotes a monocyclic, bicyclic or polycyclic aromatic system, preferably having 6 to 14, in particular 6 to 10, ring carbon atoms, such as phenyl, naphthyl, anthryl, phenanthrenyl, and preferably phenyl. Furthermore, aryl also denotes condensed polycyclic systems in which the bonding site is on the aromatic system, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenyl, etc. Aryl groups according to the present invention can be substituted with one or more identical or different radicals.

[0057] An example of a substituted aryl is arylalkyl, which is a C1-C4-alkyl moiety and / or a C6-C 14 The aryl moiety may likewise be substituted with one or more identical or different radicals. Examples of such arylalkyl include benzyl and phenyl-1-ethyl.

[0058] According to the present invention, the term "polycyclic" ring means fused, bridged and spirocyclic carbocyclic and heterocyclic rings, as well as ring systems linked via single or double bonds.

[0059] According to the present invention, a "heterocycle," "heterocyclic ring," or "heterocyclic ring system" refers to a carbocyclic ring system having at least one ring (which may be unsubstituted or substituted and the bonding site is on a ring atom) in which at least one carbon atom is replaced with a heteroatom (preferably a heteroatom selected from the group consisting of N, O, S, P, B, Si, and Se) and which is saturated, unsaturated, or heteroaromatic. Unless otherwise defined, the heterocyclic ring preferably contains 3 to 9 ring atoms (especially 3 to 6 ring atoms) and one or more (preferably 1 to 4, especially 1, 2, or 3) heteroatoms (preferably selected from the group consisting of N, O, and S) in the heterocyclic ring, provided that no two oxygen atoms are directly adjacent. The heterocyclic ring typically contains up to four nitrogen atoms and / or up to two oxygen atoms and / or up to two sulfur atoms. In the case of optionally substituted heterocyclyl, the invention also encompasses polycyclic ring systems such as, for example, 8-azabicyclo[3.2.1]octanyl, 1-azabicyclo[2.2.1]heptyl, 1-oxa-5-azaspiro[2.3]hexyl or 2,3-dihydro-1H-indole.

[0060] Heterocyclyl groups according to the present invention include, for example, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, thiazolidinyl, oxazolidinyl, dioxolanyl, dioxolyl, pyrazolidinyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, oxiranyl, azetidinyl, aziridinyl, oxazetidinyl, oxaziridinyl, oxazepanyl, oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl, oxomorpholinyl, oxopiperazinyl and oxepanyl.

[0061] Of particular importance are heteroaryls, i.e., heteroaromatic systems. According to the present invention, the term "heteroaryl" refers to heteroaromatic compounds, i.e., fully unsaturated aromatic heterocyclic compounds encompassed by the above definition of heterocycle. Preferred are 5- to 7-membered rings containing 1 to 3 (preferably 1 or 2) identical or different heteroatoms selected from the above group. Heteroaryl according to the invention is, for example, furyl, thienyl, pyrazolyl, imidazolyl, 1,2,3- and 1,2,4-triazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,3,4-, 1,2,4- and 1,2,5-oxadiazolyl, azepinyl, pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-, 1,2,4- and 1,2,3-triazinyl, 1,2,4-, 1,3,2-, 1,3,6-, and 1,2,6-oxazinyl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and 1,2,4-diazepinyl. Heteroaryl groups according to the present invention may also be substituted with one or more identical or different radicals.

[0062] According to the invention, the substituent =O (oxo) can replace the two hydrogen atoms of a methylene (CH2) group or the lone electron pair of sulfur, nitrogen and phosphorus atoms which only have non-hydrogen substituents. For example, the radical C2-alkyl can be, for example, substituted by =O (oxo) to give -COCH3, and the heterocycle thietan-3-yl can be, for example, 1-oxothietan-3-yl by substitution with one =O (oxo) group or 1,1-dioxothietan-3-yl by substitution with two =O (oxo) groups.

[0063] According to the invention, the substituent =S (thiono) can replace two hydrogen atoms of a methylene (CH2) group, for example, a radical C2-alkyl can be, for example, substituted by =S (thiono) to give -CSCH3.

[0064] As used herein, the phrase "optionally substituted" means that the optionally substituted group is either substituted with a further substituent or is not substituted with a further substituent.

[0065] The term "optionally substituted in each case" means that groups / substituents, such as alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radicals, are substituted, which means, for example, substituted radicals derived from an unsubstituted base structure, where the substituents (for example, one substituent or several substituents, preferably 1, 2, 3, 4, 5, 6 or 7 substituents) are, for example, amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C1-C4-carboxyl, carbonamido , SF5, aminosulfonyl, C1-C4-alkyl, C1-C4-haloalkyl, C3-C4-cycloalkyl, C2-C4-alkenyl, C5-C6-cycloalkenyl, C2-C4-alkynyl, N-mono-C1-C4-alkylamino, N,N-di-C1-C4-alkylamino, N-C1-C4-alkanoylamino, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C3-C4-cycloalkoxy, C5-C6-cycloalkenyloxy, C1-C4-alkoxycarbonyl, C2-C4-alkenyloxycarbonyl, C2-C4-alkynyloxycarbonyl, C6-aryloxycarbonyl, C 10 -aryloxycarbonyl, C 14 -aryloxycarbonyl, C1-C4-alkanoyl, C2-C4-alkenylcarbonyl, C2-C4-alkynylcarbonyl, C6-arylcarbonyl, C 10 -arylcarbonyl, C 14-arylcarbonyl, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C4-cycloalkylthio, C2-C4-alkenylthio, C5-C6-cycloalkenylthio, C2-C4-alkynylthio, C1-C4-alkylsulfinyl (wherein both enantiomers of a C1-C4-alkylsulfinyl group are included), C1-C4-haloalkylsulfinyl (wherein both enantiomers of a C1-C4-haloalkylsulfinyl group are included), C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, N-mono-C1-C4-alkylaminosulfonyl, N,N-di-C1-C4-alkylaminosulfonyl, C1-C4-alkylphosphinyl, C1-C4-alkylphosphonyl (wherein both the enantiomers of C1-C4-alkylphosphinyl and C1-C4-alkylphosphonyl are included), N-C1-C4-alkylaminocarbonyl, N,N-di-C1-C4-alkylaminocarbonyl, N-C1-C4-alkanoylaminocarbonyl, N-C1-C4-alkanoyl-N-C1-C4-alkylaminocarbonyl, C6-aryl, C 10 -aryl, C 14 -aryl, C6-aryloxy, C 10 -aryloxy, C 14 -aryloxy, benzyl, benzyloxy, benzylthio, C6-arylthio, C 10 -arylthio, C 14 -arylthio, C6-arylamino, C 10 -arylamino, C 14-arylamino, benzylamino, heterocyclyl and trialkylsilyl, substituents attached via a double bond (e.g., C1-C4-alkylidene (e.g., methylidene or ethylidene), oxo, imino and substituted imino). When two or more radicals form one or more rings, these can be carbocyclic, heterocyclic, saturated, partially saturated, unsaturated (including, for example, aromatic rings), and may be further substituted. The substituents listed above by way of example ("first substituent level"), if they contain a hydrocarbonaceous moiety, may have further substituents therein ("second substituent level"), such as one or more substituents each independently selected from halogen, hydroxyl, amino, nitro, cyano, isocyano, azido, acylamino, oxo and imino. The term "(optionally) substituted" group preferably includes only one or two substituent levels.

[0066] The halogen-substituted or halogenated chemical group (e.g., alkyl or alkoxy) according to the present invention is mono-substituted with halogen or poly-substituted with halogen up to the maximum possible number of substituents. Such a group is also referred to as a halo group (e.g., haloalkyl). When poly-substituted with halogen, the halogen atoms may be the same or different and may all be bonded to one carbon atom or to multiple carbon atoms. The halogen is, in particular, fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine. More particularly, the halogen-substituted group is monohalocycloalkyl, such as 1-fluorocyclopropyl, 2-fluorocyclopropyl, or 1-fluorocyclobutyl; monohaloalkyl, such as 2-chloroethyl, 2-fluoroethyl, 1-chloroethyl, 1-fluoroethyl, chloromethyl, or fluoromethyl; perhaloalkyl, such as trichloromethyl, trifluoromethyl, or CFCF; polyhaloalkyl, such as difluoromethyl, 2-fluoro-2-chloroethyl, dichloromethyl, 1,1,2,2-tetrafluoroethyl, or 2,2,2-trifluoroethyl. Further examples of haloalkyl are trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chloromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, pentafluoroethyl, 3,3,3-trifluoropropyl, and pentafluoro-t-butyl. Preferred is haloalkyl having 1 to 4 carbon atoms and 1 to 9 (preferably 1 to 5) identical or different halogen atoms selected from fluorine, chlorine and bromine. Particularly preferred is haloalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms selected from fluorine and chlorine (e.g., difluoromethyl, trifluoromethyl or 2,2-difluoroethyl, among others).Further examples of compounds substituted with halogen are haloalkoxy, such as OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3, OCH2CHF2 and OCH2CH2Cl, haloalkylsulfanyl, such as difluoromethylthio, trifluoromethylthio, trichloromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2,2,2-trifluoroethylthio or 2-chloro-1,1,2-trifluoroethylthio, haloalkylsulfinyl, such as difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, chlorodifluoromethylsulfinyl, 1-fluoroethylsulfinyl, 2-fluoroethylsulfinyl, 2,2-difluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and 2-chloro-1,1,2-trifluoroethylsulfinyl, haloalkylsulfinyl, such as difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, chlorodifluoromethylsulfinyl, 1-fluoroethylsulfinyl, 2-fluoroethylsulfinyl, 2,2-difluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and 2-chloro-1,1,2-trifluoroethylsulfinyl, haloalkylsulfonyl groups, such as difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, chlorodifluoromethylsulfonyl, 1-fluoroethylsulfonyl, 2-fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl and 2-chloro-1,1,2-trifluoroethylsulfonyl.

[0067] In the case of radicals having carbon atoms, preference is given to those having 1 to 4 carbon atoms (especially 1 or 2 carbon atoms). Generally, substituents selected from the group consisting of halogen (e.g., fluorine and chlorine), (C1-C4) alkyl (preferably methyl or ethyl), (C1-C4) haloalkyl (preferably trifluoromethyl), (C1-C4) alkoxy (preferably methoxy or ethoxy), (C1-C4) haloalkoxy, nitro and cyano are preferred. Particular preference is given here to the substituents methyl, methoxy, fluorine and chlorine.

[0068] Substituted amino (for example mono- or di-substituted amino) means a radical selected from the group of substituted amino radicals N-substituted by one or two identical or different radicals selected from the group alkyl, hydroxy, amino, alkoxy, acyl and aryl; preferably N-monoalkylamino and N,N-dialkylamino (for example methylamino, ethylamino, N,N-dimethylamino, N,N-diethylamino, N,N-di-n-propylamino, N,N-diisopropylamino or N,N-dibutylamino), N-monoalkoxyalkylamino or N,N-dialkoxyalkylamino groups (for example N-methoxy).

[0023] The term "amino" refers to, for example, optionally substituted aniline, acylamino, N,N-diacylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino, and also saturated N-heterocycles; where preference is given to alkyl radicals having 1 to 4 carbon atoms; where aryl is preferably phenyl or substituted phenyl; for acyl, the definition given further below applies, preferably (C1-C4)-alkanoyl. The same applies to substituted hydroxylamino or hydrazino.

[0069] Substituted amino also includes quaternary ammonium compounds (salts) having four organic substituents on the nitrogen atom.

[0070] Optionally substituted phenyl is preferably unsubstituted phenyl or is identical or different and selected from the group consisting of halogen, (C-C)-alkyl, (C-C)-alkoxy, (C-C)-alkoxy-(C-C)-alkoxy, (C-C)-alkoxy-(C-C)-alkyl, (C-C)-haloalkyl, (C-C)-haloalkoxy, (C-C)-alkylthio, (C-C)-haloalkylthio, (C-C)-alkylsulfinyl, (C-C)-haloalkylsulfinyl, (C-C)-alkylsulfonyl, (C-C)-haloalkylsulfonyl, cyano, isocyano and nitro. and 4-trifluoromethylphenyl, 2,4-dichlorophenyl, 3,5-dichlorophenyl, 2,5-dichlorophenyl, and 2,3-dichlorophenyl, o-methoxyphenyl, m-methoxyphenyl, and p-methoxyphenyl, 4-heptafluorophenyl.

[0071] Optionally substituted cycloalkyl is preferably unsubstituted cycloalkyl or cycloalkyl which is mono- or polysubstituted (preferably up to tri-substituted) by identical or different radicals selected from the group consisting of halogen, cyano, (C-C)-alkyl, (C-C)-alkoxy, (C-C)-alkoxy-(C-C)-alkoxy, (C-C)-alkoxy-(C-C)-alkyl, (C-C)-haloalkyl and (C-C)-haloalkoxy, in particular cycloalkyl substituted by one or two (C-C)-alkyl radicals.

[0072] The compounds of the present invention can be in preferred embodiments.The individual embodiments described herein can be combined with each other.Does not include the combination that is contrary to the law of nature, and therefore, those skilled in the art would exclude based on their own expertise.For example, the ring structure that has three or more adjacent oxygen atoms is excluded.

[0073] Isomers Depending on the type of substituents, the compounds of formula (I) can exist in the form of geometric isomers and / or optically active isomers or in the form of corresponding isomeric mixtures of different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The present invention therefore encompasses both the pure stereoisomers and any mixtures of these isomers.

[0074] isotopic variants The present invention also encompasses all suitable isotopic variations of compounds of formula (I). An isotopic variation of such a compound is understood to mean a compound of formula (I) in which at least one atom has been replaced by another atom having the same atomic number but an atomic mass different from the atomic mass normally or predominantly occurring in nature. Examples of isotopes that can be incorporated into compounds of formula (I) include isotopes of hydrogen, carbon, nitrogen, oxygen, phosphorus, sulfur, fluorine, chlorine, bromine and iodine, such as: 2H (deuterium), 3 H (tritium), 13 C. 14 C. 15 N, 17 O. 18 O. 32 P, 33 P, 33 S, 34 S, 35 S, 36 S, 18 F, 36 Cl, 82 Br, 123 I, 124 I, 129 I and 131 I. Certain isotopic variations of compounds of formula (I), such as, in particular, those having one or more radioisotopes incorporated therein, may be useful, for example, for studying the mechanism of action or distribution of the active ingredient (e.g., the mechanism of action or distribution of the active ingredient within the body of a pathogen); for this purpose, 3 H isotope or 14 Compounds labeled with C isotopes are particularly suitable due to their relative ease of preparation and detection. Furthermore, the incorporation of an isotope (e.g., deuterium) can provide advantages (e.g., increased half-life or reduced required effective dose), for example, as a result of increasing the metabolic stability of the compound. Therefore, isotopic modifications of compounds of formula (I) can also represent preferred embodiments of the present invention. Isotopic variants of compounds of formula (I) can be prepared by methods known to those skilled in the art, for example, by using appropriate isotopic modifications of individual reagents and / or starting compounds (isolated compounds) according to the methods and instructions provided in the representative embodiments described below.

[0075] Methods and Uses The present invention also relates to a method for controlling pests, in which a compound of formula (I) is applied to pests and / or their habitat. The control of pests is preferably carried out in agriculture and forestry, and in the protection of materials. Preferably, methods for surgical or therapeutic treatment of the human or animal body and diagnostic methods carried out on the human or animal body are excluded from the methods.

[0076] The present invention further relates to the use of compounds of formula (I) as pesticides, in particular as crop protection agents.

[0077] In the context of this application, the term "pesticide" always also encompasses the term "crop protection agent".

[0078] The compounds of formula (I), which are well tolerated by plants, have a desirable level of toxicity to warm-blooded animals and show good environmental compatibility, are suitable for protecting plants and plant organs against biotic and abiotic stressors, for increasing yields and improving the quality of harvested products, and for controlling pests, in particular insects, arachnids, helminths, especially nematodes, and mollusks, encountered in agriculture, horticulture, animal husbandry, aquaculture, forestry, gardens and leisure facilities, in the protection of stored products and materials, and in the field of hygiene.

[0079] In the context of this patent application, the term "hygiene" is understood to mean any and all means, methods and practices aimed at preventing diseases (in particular infectious diseases), as well as any and all means, methods and practices that serve to protect human and animal health and / or to protect the environment and / or to maintain cleanliness. According to the invention, this includes in particular means for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces (in particular surfaces made of glass, wood, concrete, porcelain, ceramic, plastic, or even metal(s)), as well as means for ensuring that these remain free from sanitary pests and / or their excrement. In this context, preferably, surgical or therapeutic procedures that can be performed on the human or animal body, as well as diagnostic methods performed on the human or animal body, are excluded from the scope of protection according to the invention.

[0080] The term "field of hygiene" therefore includes all areas, technical and industrial applications in which such hygienic means, methods and practices are important, such as, for example, all areas, technical and industrial applications relating to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, hospitals, stables, animal husbandry, etc.

[0081] Therefore, the term "sanitary pests" is understood to mean one or more pests whose presence is problematic in the field of hygiene, especially for health reasons.Therefore, the main objective is to avoid or minimize the presence of sanitary pests in the field of hygiene, and / or to avoid or minimize contact with sanitary pests.This can be achieved in particular by applying insecticides that can be used both to prevent outbreaks and to tackle existing outbreaks.It is also possible to use preparations that avoid or reduce contact with pests.Sanitation pests can include, for example, the organisms listed below.

[0082] Thus, the term "hygienic protection" includes all actions that maintain and / or improve such hygienic means, methods and practices.

[0083] The compounds of formula (I) can be preferably used as pesticides. They are effective against normally sensitive and resistant species and are active against all or some of the developmental stages of insects. Such pests include:

[0084] Pests from the phylum Arthropoda, in particular from the class Arachnida, for example Acarus spp., for example Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., for example Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp. spp., for example, Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., for example, Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp. e.g. Eutetranychus banksi, Eriophyes spp.), e.g., Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., e.g., Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp. spp.), Oligonychus spp., e.g., Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp.), for example, Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp. spp.), Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., e.g., Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., e.g., Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici;. From the class Chilopoda, for example, Geophilus spp., Scutigera spp.; From the order of the Collembola or class of the Springtails, for example, Onychiurus armatus; Sminthurus viridis; From the class Diplopoda, for example, Blaniulus guttulatus; From the class of Insecta, for example, from the order Blattodea, for example, Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., for example, Periplaneta americana, Periplaneta australasiae australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order Coleoptera, for example, Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp., for example, Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius, Agriotes spp., for example, Agriotes linneatus; linneatus, Agriotes mancus, Agriotes obscurus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anomala dubia, Anoplophora spp., e.g., Anoplophora glabripennis, Anthonomus spp., e.g., Anthonomus grandis, Anthrenus spp., Apion spp. spp.), Apogonia spp., Athous haemorrhoidales, Atomaria spp. e.g. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp.), for example, Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., for example, Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., for example, Chaetocnema confinis, Chaetocnema denticulata denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., for example, Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., for example, Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp.), Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dendroctonus spp., for example, Dendroctonus ponderosae, Dermestes spp., Diabrotica spp., for example, Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., e.g., Epilachna borealis, Epilachna varivestis, Epitrix spp., e.g., Epitrix cucumeris, Epitrix fuscula fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp.), Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hoplia argentea, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., e.g., Hypothenemus hampeii, hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa ​​decemlineata, Leucoptera spp., e.g., Leucoptera coffeella, Limonius ectipus ectypus, Lissorhoptrus oryzophilus, Listronotus spp. (= Hyperodes spp.), Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp.), for example, Megacyllene robiniae, Megascelis spp., Melanotus spp., for example, Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., for example, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp. spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp. such as Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp. spp., for example, Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp.), for example, Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., for example, Psylliodes affinis. ), Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Scolytus spp., e.g., Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp. spp., for example, Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., for example, Sternechus paludatus, Symphyletes spp., Tanymecus spp., for example, Tanymecus dilaticollis, Tanymecus indicus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp.), for example, Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., for example, Zabrus tenebrioides;. From the order Dermaptera, for example, Anisolabis maritime, Forficula auricularia, Labidura riparia; From the order of the Diptera, for example, Aedes spp., for example, Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., for example, Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., for example, Anopheles quadrimaculatus, Anopheles gumbiae, gambiae, Asphondylia spp., Bactrocera spp., e.g., Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp. spp.), Chrysozona pluvialis, Cochliomya spp., Contarinia spp.), for example, Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., for example, Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp. spp., Cuterebra spp., Dacus oleae, Dasineura spp., for example Dasineura brassicae, Delia spp., for example Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., for example Drosophila melanogaster, Drosophila suzukii suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp.), Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., e.g. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., e.g. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp. spp., for example, Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyia spp., for example, Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp. spp.), Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp.), for example, Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., for example, Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp. spp.), e.g. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; From the order of the Hemiptera, for example, Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., for example, Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., e.g., Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., e.g., Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp.), such as Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis bivulniphila viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp. e.g., Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp. spp.), Brevicoryne brassicae, Cacopsylla spp., e.g., Cacopsylla pyricola, Calligypona marginata, Capulinia spp.), Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp. such as Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri citri), Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp.), for example, Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., for example, Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., for example, Eriosoma americanum, americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp. e.g. Icerya purchasi, Idiocerus spp., Idioscopus spp.), Laodelphax striatellus, Lecanium spp., for example, Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., for example, Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., for example, Macrosiphum euphorbiae, Macrosiphum lily lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., e.g., Myzus ascalonicus, Myzus cerasi, Myzus ligustri ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp.), for example, Nephotettix cincticeps, Nephotettix nigropictus, Nettigonicella spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., for example, Paratrioza cockerelli, Parlatoria spp. spp.), Pemphigus spp., e.g., Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., e.g., Fena. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., for example, Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., for example, Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., for example, Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., for example, Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp.), for example, Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., for example, Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale rufiabdominale, Saissetia spp., e.g., Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp. spp.), Stictocephala festina, Siphoninus phillyreae, Tenalapha malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomasis spp.), Toxoptera spp., e.g., Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., e.g., Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;. From the order Heteroptera, for example, Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., for example Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilocerus pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., e.g., Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurydema spp. spp.), Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp.), Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., e.g., Lygocoris pabulinus, Lygus spp., e.g., Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum atratum, Nezara spp., e.g., Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., e.g., Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea castanea), Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.;. From the order of the Hymenoptera, for example, Acromyrmex spp., Athalia spp., for example, Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., for example, Diprion similis, Hoplocampa spp., for example, Hoplocampa cookei, Hoplocampa testudinea, Lasius spp. spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., for example Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., for example Vespa crabro crabro), Wasmannia auropunctata, Xeris spp.; From the order Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber; From the order Isoptera, for example, Coptotermes spp., for example Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermes spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., for example Reticulitermes flavipes flavipes), Reticulitermes hesperus; From the order of the Lepidoptera, for example, Achroia grisella, Acronicta major, Adoxophyes spp., for example, Adoxophyes orana, Aedia leucomelas, Agrotis spp., for example, Agrotis segetum, Agrotis ipsilon, Alabama spp., for example, Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp. spp., such as Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp.), e.g. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp. spp., e.g., Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., e.g., Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp. spp.), for example, Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp.), Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., for example Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracilaria spp., Grapholitha spp., for example Grapholitha molesta molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., for example, Helicoverpa armigera, Helicoverpa zea, Heliothis spp., for example, Heliothis virescens, Hepialus spp., for example, Hepialus humuli, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padera padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp.), for example, Leucoptera coffeella, Lithocolletis spp., for example, Lithocolletis blancardella, Lithophane antennata, Lobesia spp., for example, Lobesia botrana, Loxagrotis albicosta, Lymantria spp., for example, Lymantria dispar, Lyonetia spp., for example, Lyonetia clerkella, Malacosoma neustria neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp. spp., e.g., Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp., e.g., Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp.), for example, Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., for example, Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., for example, Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella macripennis), maculipennis), Podesia spp., for example, Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., for example, Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., for example, Schoenobius bipunctifer bipunctifer, Scirpophaga spp., e.g., Scirpophaga innotata, Scotia segetum, Sesamia spp., e.g., Sesamia inferens, Sparganothis spp., Spodoptera spp.), for example, Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea croacella cloacella), Tinea pellionella,. Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., e.g., Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.; From the order of the Orthoptera or Saltatoria, for example, Acheta domesticus, Dichroplus spp., Gryllotalpa spp., for example Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., for example Locusta migratoria, Melanoplus spp., for example Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; From the order Phthiraptera, for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; From the order Psocoptera, for example, Lepinotus spp., Liposcelis spp.; From the order of the Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp., for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order Thysanoptera, for example, Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., e.g., Thrips palmi, Thrips tabaci; From the order Zygentoma (= Thysanura), for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; From the class of the Symphyla, for example, Scutigerella spp., for example, Scutigerella immaculata; Pests from the phylum Mollusca, for example from the class Bivalvia, for example Dreissena spp.; and also From the class of the Gastropoda, for example, Arion spp., for example, Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., for example, Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; Plant pests (i.e. plant-parasitic nematodes) of the phylum Nematoda, in particular Aglenchus spp., for example Aglenchus agricola, Anguina spp., for example Anguina tritici, Aphelenchoides spp., for example Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., for example Belonolaimus gracilis, Belonolaimus longicaudatus, longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., for example, Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., for example, Cacopaurus pestis, Criconemella spp., for example, Criconemella curvata, Criconemella onoensis, Criconemella ornata ornata), Criconemella rusium, Criconemella xenoplax (=Mesocriconema xenoplax), Criconemoides spp.), for example, Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., for example, Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., for example, Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., for example, Helicotylenchus dihystera dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., for example, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., for example, Longidorus africanus, Meloidogyne spp., for example, Meloidogyne kitwooji chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp.), Paraphelenchus spp., Paratrichodorus spp., for example, Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., for example, Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., for example, Radopholus citrophilus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., for example, Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., for example, Tylenchorhynchus annulatus, Tylenchulus spp. spp.), for example, Tylenchulus semipenetrans, Xiphinema spp., for example, Xiphinema index.

[0085] The compounds of formula (I) may optionally also be used, at certain concentrations or at certain application rates, as herbicides, safeners, growth regulators or plant property-improving agents, or as microbicides or gametocides, for example as fungicides, antimycotics, bactericides or viricides (which also include agents acting against viroids), or as agents acting against MLOs (mycoplasma-like organisms) and RLOs (rickettsia-like organisms). Where appropriate, they may also be used as intermediates or precursors for the synthesis of further active compounds.

[0086] Formulation / Usage Form The present invention further relates to formulations, in particular formulations for controlling unwanted animal pests, which can be applied to the animal pests and / or their habitat.

[0087] The formulations of the present invention can be provided to the end user as a "ready-for-use" use form, i.e., the formulations can be applied directly to plants or seeds by suitable equipment, such as spraying or dusting equipment. Alternatively, the formulations can be provided to the end user in the form of a concentrate that requires dilution, preferably with water, before use. Thus, unless otherwise indicated, the expression "formulation" refers to such a concentrate, while the expression "use form" refers to the end user as a "ready-to-use" solution, i.e., usually as such a diluted formulation.

[0088] The formulations of the present invention can be prepared in a conventional manner, for example, by combining a compound of the present invention with one or more suitable adjuvants, such as those disclosed herein.

[0089] The formulations comprise at least one compound of the invention and at least one agriculturally suitable adjuvant (eg, carrier(s) and / or surfactant(s)).

[0090] Carriers are generally inert, solid or liquid, natural or synthetic organic or inorganic substances. Such carriers generally improve the application of the compound, for example, to plants, plant parts, or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, especially ammonium sulfate, ammonium phosphate, and ammonium nitrate; natural rock powders such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth; silica gel; and synthetic rock powders such as micronized silica, alumina, and silicates. Examples of solid carriers typically useful for preparing granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, and dolomite; synthetic granules made from inorganic and organic powders; and granules made from organic materials such as paper, sawdust, coconut shells, corn cobs, and tobacco stems. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof.Examples of suitable solvents include polar and non-polar organic chemical liquids, such as those selected from the following classes: aromatic and non-aromatic hydrocarbons (e.g., cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthylene, alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may optionally be substituted, etherified and / or esterified, e.g., ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or glycol), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone or cyclohexanone), ), esters (which include fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (for example dimethylformamide or fatty acid amides) and their esters, lactams (for example N-alkylpyrrolidones, in particular N-methylpyrrolidone) and lactones, sulfones and sulfoxides (for example dimethyl sulfoxide), oils of vegetable or animal origin, nitriles (alkyl nitriles, for example acetonitrile, propionotrile, butyronitrile, or aromatic nitriles, for example benzonitrile), carbonates (cyclic carbonates, for example ethylene carbonate, propylene carbonate, butylene carbonate, or dialkyl carbonates, for example dimethyl carbonate, diethyl carbonate, dipropyl carbonate, dibutyl carbonate, dioctyl carbonate). The carrier can also be a liquefied gas extender, that is, a liquid that is a gas at standard temperature and pressure, such as an aerosol propellant, eg, halohydrocarbons, butane, propane, nitrogen, and carbon dioxide.

[0091] Preferred solid carriers are selected from clay, talc and silica.

[0092] Preferred liquid carriers are selected from water, fatty acid amides and their esters, aromatic and non-aromatic hydrocarbons, lactams, lactones, carbonates, ketones, (poly)ethers.

[0093] The amount of carrier is typically in the range of 1 to 99.99% by weight of the formulation, preferably in the range of 5 to 99.9% by weight, more preferably in the range of 10 to 99.5% by weight, and most preferably in the range of 20 to 99% by weight.

[0094] The liquid carrier is typically present in the range of 20 to 90% by weight of the formulation, for example, in the range of 30 to 80% by weight.

[0095] The solid carrier is typically present in the range of 0 to 50% by weight of the formulation, preferably in the range of 5 to 45% by weight, for example, in the range of 10 to 30% by weight.

[0096] When the formulation includes two or more carriers, the approximate range refers to the total amount of carriers.

[0097] The surfactant may be an ionic (cationic or anionic), zwitterionic or nonionic surfactant, such as an ionic or nonionic emulsifier, foam former, dispersant, wetting agent, penetration enhancer, or any mixture thereof. Examples of suitable surfactants include, but are not limited to, salts of polyacrylic acid, ethoxylated poly(α-substituted)acrylate derivatives, salts of lignosulfonic acid (e.g., sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and / or propylene oxide with or without alcohols or fatty acids or fatty amines (polyoxyethylene fatty acid esters, e.g., castor oil ethoxylate, polyoxyethylene fatty alcohol ethers, e.g., alkylaryl polyglycol ethers), substituted phenols (preferably alkyl esters), hydroxybenzoates, ... Examples of suitable salts include alkylphenols or arylphenols, salts of sulfosuccinates, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or polyethoxylated phenols, fatty esters of polyols (e.g., fatty acid esters of glycerol, sorbitol, or sucrose), sulfates (e.g., alkyl sulfates and alkyl ether sulfates), sulfonates (e.g., alkyl benzoates, aryl sulfonates, and alkylbenzene sulfonates), sulfonated polymers of naphthalene / formaldehyde, phosphoric acid esters, protein hydrolysates, lignosulfite waste liquors, and methylcellulose. References to salts in this paragraph preferably refer to the respective alkali, alkaline earth metal, and ammonium salts.

[0098] Preferred surfactants are selected from ethoxylated poly(α-substituted) acrylate derivatives, polycondensates of ethylene oxide and / or propylene oxide containing alcohols, polyoxyethylene fatty acid esters, alkylbenzenesulfonates, sulfonated polymers of naphthalene / formaldehyde, polyoxyethylene fatty acid esters such as castor oil ethoxylates, sodium lignosulfonates and arylphenol ethoxylates.

[0099] The amount of surfactant is typically in the range of 5 to 40% by weight of the formulation, for example in the range of 10 to 20% by weight.

[0100] Further examples of suitable adjuvants include: water repellents, drying agents, binders (adhesives, tackifiers, fixatives, e.g. carboxymethylcellulose, as well as natural and synthetic polymers in the form of powders or granules or latex, e.g. gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids, e.g. cephalin and lecithin, and synthetic phospholipids, polyvinylpyrrolidone and tylose), thickeners and secondary thickeners (e.g. cellulose ethers, acrylic acid derivatives, xanthan gum, cellulose acetate, cellulose acetate derivatives ... gums, modified clays, for example the products available under the name Bentone and micronized silica), stabilizers (for example low-temperature stabilizers, preservatives (for example dichlorophen, benzyl alcohol hemiformal, 1,2-benzisothiazolin-3-one, 2-methyl-4-isothiazolin-3-one), antioxidants, light stabilizers, in particular UV stabilizers, or other agents improving chemical and / or physical stability), dyes or pigments (for example inorganic pigments, for example iron oxide, titanium oxide and Prussian blue). Blue); organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes), antifoaming agents (such as silicone antifoams and magnesium stearate), antifreeze agents, fixing agents, gibberellins and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (which include micronutrients such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts), protective colloids, thixotropic substances, penetrating agents, sequestering agents and complex formers.

[0101] The choice of the adjuvant depends on the intended application method of the compound of the present invention and / or the physical properties of the compound.In addition, the adjuvant can also be selected to impart special properties (technical properties, physical properties and / or biological properties) to the formulation or the use form prepared from the formulation.By selecting the adjuvant, the formulation can be customized to meet specific needs.

[0102] The formulations contain an insecticidally / acaricidally / nematicidally effective amount of the compound(s) of the present invention. The term "effective amount" refers to an amount sufficient to control harmful insects / mites / nematodes on cultivated plants or to protect materials, without causing substantial damage to the treated plants. Such amounts can vary within a wide range and depend on various factors, such as the species of insects / mites / nematodes to be controlled, the cultivated plants or materials being treated, climatic conditions, and the particular compound of the present invention used. Typically, formulations according to the present invention contain 0.01 to 99% by weight, preferably 0.05 to 98% by weight, more preferably 0.1 to 95% by weight, even more preferably 0.5 to 90% by weight, and most preferably 1 to 80% by weight of the compound of the present invention. The formulations may contain two or more compounds of the present invention. In such cases, the approximate ranges refer to the total amount of the compound of the present invention.

[0103] The formulations of the present invention can be of any conventional formulation type, such as solutions (e.g., aqueous solutions), emulsions, aqueous and oily suspensions, dusts (e.g., wettable powders, soluble powders), dusts, pastes, granules (e.g., soluble granules, broadcast granules), suspoemulsions, natural or synthetic products impregnated with the compounds of the present invention, fertilizers, and even microencapsulated in polymeric materials. The compounds of the present invention can be present in suspended, emulsified, or dissolved form. Examples of specific suitable formulation types are solutions, water-soluble concentrates (e.g., SL, LS), dispersible concentrates (DC), suspensions and suspension concentrates (e.g., SC, OD, OF, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME, SE), capsules (e.g., CS, ZC), pastes, pastilles, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), pressings (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticidal products (e.g., LN), and gel formulations for treating plant propagation material (e.g., seeds) (e.g., GW, GF). These and further formulation types are defined by the Food and Agriculture Organization of the United Nations (FAO). An overview is provided in "Catalogue of pesticide formulation types and international coding system," Technical Monograph No. 2, 6th Ed. May 2008, Croplife International.

[0104] Preferably, the formulation of the present invention is in the form of one of the following types: EC, SC, FS, SE, OD, WG, WP, CS, more preferably EC, SC, OD, WG, CS.

[0105] Examples of formulation types and further details about their preparation are provided below. When two or more compounds of the invention are present, the approximate amount of compounds of the invention refers to the total amount of compounds of the invention. This also applies mutatis mutandis to any additional components of the formulation (e.g., wetting agent, binder), when two or more representatives of such components are present.

[0106] (i) Water-soluble thickeners (SL, LS) 10 to 60% by weight of at least one compound of the present invention and 5 to 15% by weight of a surfactant (e.g., an alcohol-containing polycondensate of ethylene oxide and / or propylene oxide) are dissolved in water and / or a water-soluble solvent (e.g., an alcohol such as propylene glycol, or a carbonate such as propylene carbonate) in an amount such that the total amount becomes 100% by weight. Before application, the concentrate is diluted with water.

[0107] (ii) Dispersible Thickener (DC) 5 to 25% by weight of at least one compound of the present invention and 1 to 10% by weight of a surfactant and / or binder (e.g., polyvinylpyrrolidone) are dissolved in an organic solvent (e.g., cyclohexanone) in an amount such that the total amount becomes 100% by weight. A dispersion is obtained by diluting with water.

[0108] (iii) Emulsifiable concentrate (EC) 15 to 70% by weight of at least one compound of the present invention and 5 to 10% by weight of a surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e.g., an aromatic hydrocarbon or a fatty acid amide) and, if necessary, an additional water-soluble solvent, in amounts such that the total amount becomes 100% by weight. An emulsion is obtained by diluting the solution with water.

[0109] (iv) Emulsifying agents (EW, EO, ES) 5-40% by weight of at least one compound of the present invention and 1-10% by weight of a surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, or a polycondensate of ethylene oxide and / or propylene oxide with or without alcohol) are dissolved in 20-40% by weight of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon). This mixture is added to water in an amount to make the total amount 100% by weight using an emulsifier. The resulting formulation is a homogeneous emulsion. Before application, the emulsion can be further diluted with water.

[0110] (v) Suspensions and suspension preparations (v-1) Water-based (SC, FS) In a suitable milling device (e.g., a stirred ball mill), 20-60% by weight of at least one compound of the present invention is milled with 2-10% by weight of surfactants (e.g., sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2% by weight of a thickener (e.g., xanthan gum), and water to obtain a finely divided active substance suspension. Water is added in an amount such that the total amount is 100% by weight. Dilution with water results in a stable suspension of the active substance. In FS-type formulations, up to 40% by weight of a binder (e.g., polyvinyl alcohol) is added.

[0111] (v-2) Oil-based (OD, OF) In a suitable milling device (e.g., an agitator ball mill), 20 to 60% by weight of at least one compound of the present invention is milled with 2 to 10% by weight of a surfactant (e.g., sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1 to 2% by weight of a thickener (e.g., modified clay, especially Bentone, or silica), and an organic carrier to obtain a finely divided active substance oil suspension. The organic carrier is added in such an amount that the total amount is 100% by weight. Dilution with water gives a stable dispersion of the active substance.

[0112] (vi) Water dispersible granules and water-soluble granules (WG, SG) 1 to 90% by weight (preferably 20 to 80% by weight, most preferably 50 to 80% by weight) of at least one compound of the present invention is pulverized with surfactants (e.g., sodium lignosulfonate and sodium alkylnaphthylsulfonate) and, optionally, carrier materials, and converted into water-dispersible granules or water-soluble granules using typical technical equipment (e.g., extrusion granulation, spray-drying granulation, fluidized-bed granulation). The surfactants and carrier materials are used in amounts such that the total amount is 100% by weight. Dilution with water gives a stable dispersion or solution of the active substance.

[0113] (vii) Wettable powders and water-soluble powders (WP, SP, WS) 50-80% by weight of at least one compound of the present invention is milled in a rotor-stator mill with 1-20% by weight of a surfactant (e.g., sodium lignosulfonate, sodium alkylnaphthylsulfonate) and a solid carrier (e.g., silica gel) in an amount sufficient to bring the total to 100% by weight. Dilution with water results in a stable dispersion or solution of the active substance.

[0114] (viii) Gel preparations (GW, GF) In a stirred ball mill, 5-25% by weight of at least one compound of the present invention is milled with 3-10% by weight of a surfactant (e.g., sodium lignosulfonate), 1-5% by weight of a binder (e.g., carboxymethylcellulose), and an amount of water to bring the total to 100% by weight. This results in a fine suspension of the active substance. Dilution with water results in a stable suspension of the active substance.

[0115] (ix) Microemulsifiers (MEs) 5-20% by weight of at least one compound of the present invention is added to 5-30% by weight of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a surfactant blend (e.g., polyoxyethylene fatty alcohol ether and arylphenol ethoxylate), and an amount of water such that the total amount is 100% by weight. The mixture is stirred for 1 hour to spontaneously form a thermodynamically stable microemulsion.

[0116] (x) Microcapsules (CS) An oil phase containing 5 to 50% by weight of at least one compound of the present invention, 0 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and 2 to 15% by weight of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Poly(meth)acrylate microcapsules are formed by radical polymerization initiated by a radical initiator. Alternatively, an oil phase containing 5 to 50% by weight of at least one compound of the present invention, 0 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol), thereby forming polyurea microcapsules. Optionally, polyamines (e.g., hexamethylenediamine) may also be added to form polyurea microcapsules. The monomer accounts for 1 to 10% of the total weight of the CS formulation.

[0117] (xi) dustable powders (DP, DS) 1 to 10% by weight of at least one compound of the present invention is finely ground and intimately mixed with a solid carrier (eg, finely divided kaolin) in an amount such that the total amount is 100% by weight.

[0118] (xii) Granules (GR, FG) 0.5 to 30% by weight of at least one compound of the present invention is finely ground and combined with a solid carrier (eg, silicate) in an amount such that the total amount is 100% by weight.

[0119] (xiii) Ultra-low volume liquids (UL) 1 to 50% by weight of at least one compound of the present invention is dissolved in an organic solvent (for example, an aromatic hydrocarbon) in an amount such that the total amount becomes 100% by weight.

[0120] Formulation types (i) to (xiii) may optionally contain further adjuvants, such as 0.1 to 1% by weight of a preservative, 0.1 to 1% by weight of an antifoaming agent, 0.1 to 1% by weight of a dye and / or pigment, and 5 to 10% by weight of an antifreeze agent.

[0121] mixture The compounds of formula (I) can also be used in mixtures with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiological agents, beneficial species, herbicides, fertilizers, bird repellents, phytotonic agents, sterilants, safeners, semiochemicals and / or plant growth regulators, for example to broaden the spectrum of action, increase the duration of action, increase the rate of action, prevent repulsion or prevent the development of resistance. Furthermore, such active compound combinations can improve plant growth and / or improve tolerance to abiotic factors (e.g., high or low temperatures), drought or increased moisture content or soil salinity. Furthermore, it may improve flowering and fruiting performance, optimize germination ability and root development, facilitate harvesting, increase yield, influence maturation, improve the quality and / or nutritional value of the harvested product, increase the shelf life of the harvested product, and / or improve the processability of the harvested product. Furthermore, the compounds of formula (I) can be present in a mixture with other active compounds or semiochemicals (e.g., attractants, and / or bird repellents, and / or plant activators, and / or growth regulators, and / or fertilizers). Similarly, the compounds of formula (I) can be used to improve plant properties (e.g., growth, yield, and quality of the harvest). In a particular embodiment according to the invention, the compound of formula (I) is present in the formulation or in the use form prepared from such a formulation in admixture with further compounds, preferably compounds described below.

[0122] If one of the compounds described below can exist in various tautomeric forms, these forms are also included in each case, even if not explicitly mentioned. Furthermore, all named mixing partners, if possible due to their functional groups, can also form salts with suitable bases or acids, as the case may be.

[0123] Insecticides / Acaricides / Nematicides Active compounds identified herein by "common name" are known and can be found, for example, in the pesticide handbook ("The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) or on the internet (e.g., http: / / www.alanwood.net / pesticides). The classification is based on the IRAC Mode of Action Classification Scheme, current at the time of filing this patent application.

[0124] (1) Acetylcholinesterase (AChE) inhibitors, preferably Carbamates, selected from alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or Organophosphates, including acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famfur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, and O-(methoxyaminothiophosphoryl) ) isopropyl salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion.

[0125] (2) GABA-regulated chloride channel blockers, preferably cyclodiene-organochlorines, selected from chlordane and endosulfan; or Phenylpyrazoles (fiproles), which are selected from ethiprole and fipronil.

[0126] (3) sodium channel modulators, preferably Pyrethroids, which include acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans-isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fen selected from propathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorotrin, permethrin, fenothrin [(1R)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin and transfluthrin; or DDT; or methoxychlor.

[0127] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, preferably Neonicotinoids, selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or nicotine; or sulfoximines, which are selected from sulfoxaflor; or butenolides, which are selected from flupyradifurone; or Mesoionics, which are selected from triflumezopyrim.

[0128] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators (site I), preferably Spinosyns, which are selected from spinetoram and spinosad.

[0129] (6) glutamate-gated chloride channel (GluCl) allosteric modulators, preferably Avermectins / milbemycins, which are selected from abamectin, emamectin benzoate, lepimectin and milbemectin.

[0130] (7) Juvenile hormone mimetics, preferably Juvenile hormone analogs, selected from hydroprene, kinoprene, and methoprene; or Fenoxycarb; or pyriproxyfen.

[0131] (8) Various unspecified (multi-site) inhibitors, preferably an alkyl halide, selected from methyl bromide and another alkyl halide; or Chloropicrin; or sulfuryl fluoride; or borax; or tartar emetic; or A methyl isocyanate generator, which is selected from diazomet and metham.

[0132] (9) Chordotonal organ TRPV channel modulators, preferably pyridine azomethanes, selected from pymetrozine and pyrifluquinazone; or Pyropenes, which are selected from afidopyropenes.

[0133] (10) A mite growth inhibitor acting on CHS1, which is selected from clofentezine, hexythiazox, diflobidazine, and etoxazole.

[0134] (11) Microbial disruptors of the insect gut membrane, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, and Bacillus thuringiensis subspecies tenebrionis, are known to disrupt the insect gut membrane. tenebrionis) and Bt plant proteins (which are selected from Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Ab1 / 35Ab1).

[0135] (12) Inhibitors of mitochondrial ATP synthase, preferably an ATP disruptor, which is selected from diafenthiuron; or organotin compounds, selected from azocyclotin, cyhexatin and fenbutatin oxide; or Propargite; or tetradifon.

[0136] (13) An uncoupler of oxidative phosphorylation by disrupting the proton gradient, which is selected from chlorfenapyr, DNOC, and sulfluramide.

[0137] (14) Nicotinic acetylcholine receptor channel blockers, which are selected from bensultap, cartap hydrochloride, thiocylam and thiosultap-sodium.

[0138] (15) A chitin biosynthesis inhibitor acting on CHS1, preferably Benzoylureas, selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0139] (16) Chitin biosynthesis inhibitors (type 1), which are selected from buprofezin.

[0140] (17) Molting disruptors (especially for Diptera, i.e., for dipterans), which are selected from cyromazines.

[0141] (18) Ecdysone receptor agonists, preferably Diacylhydrazines, selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0142] (19) Octopamine receptor agonists, which are selected from amitraz.

[0143] (20) Mitochondrial complex III electron transport inhibitors, which are selected from hydramethylnon, acequinocyl, fluacrypyrim, and bifenazate.

[0144] (21) Mitochondrial complex I electron transport inhibitors, preferably METI acaricides and insecticides, selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or Rotenone (Derris).

[0145] (22) Voltage-dependent sodium channel blockers, preferably an oxadiazine, selected from indoxacarb; or Semicarbazones, which are selected from metaflumizone.

[0146] (23) Acetyl-CoA carboxylase inhibitors, preferably Tetronic acid derivatives and tetramic acid derivatives, which are selected from spirodiclofen, spiromesifen, spiropydione and spirotetramat.

[0147] (24) Mitochondrial complex IV electron transport inhibitors, preferably phosphides, selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or The cyanide is selected from calcium cyanide, potassium cyanide and sodium cyanide.

[0148] (25) Mitochondrial complex II electron transport inhibitors, preferably β-ketonitrile derivatives, selected from cyenopyrafen and cyflumetofen; or Carboxanilides, which are selected from piflubumid.

[0149] (28) Ryanodine receptor modulators, preferably Diamides, selected from chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide and tetraliniliprole.

[0150] (29) Chordotonal organ modulators (target site not defined), which are selected from flonicamide.

[0151] (30) GABA-regulated chloride channel allosteric modulators, preferably Metadiamides, which are selected from broflanilide; or Isoxazoles, which are selected from fluxametamide.

[0152] (31) Baculovirus, preferably Granulosis viruses (GVs), selected from Cydia pomonella GV and Thaumatotibia leucotreta (GV); or Nuclear polyhedrosis viruses (NPVs), selected from Anticarsia gemmatalis MNPV, Flucypyriprole and Helicoverpa armigera NPV.

[0153] (32) Nicotinic acetylcholine receptor allosteric modulator (site II), which is selected from GS-omega / kappa HXTX-Hv1a peptides.

[0154] (33) Further active compounds selected from the following: acinonapyr, afoxolaner, azadirachtin, benclothiaz, benzoximate, benzpyrimoxane, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclobutrifluram, cycloxapride, cyetpyrafen, cyhalodiamide, cyproflanilide (CAS 2375110-88-4), dichloromezothiaz, dicofol, dimpropyridaz, ε-metofluthrin, ε-momfluthrin, flometoquin, fluazaindolizine, flucypyriprole (CAS 2375110-88-4). 1771741-86-6), Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Flupirimine, Fluralaner, Fufenozide, Flupentiofenox, Guadipyr, Heptafluthrin, Imidaclotiz, Iprodione, Isocycloceram, κ-Bifenthrin, κ-Tefluthrin, Lotilaner, Meperfluthrin, Nicofluprole (CAS 1771741-86-6) 1771741-86-6), oxazosulfil, paichongding, pyridalyl, pyrifluquinazone, pyriminostrobin, sarolaner, spidoxamat, spirobudiclofen, tetramethylfluthrin, tetrachlorantraniliprole, tigolaner, thioxazaphen, thiofluoximate, cyclopyrazoflor, iodomethane; in addition, preparations based on Bacillus firmus (I-1582, Votivo) and azadirachtin (BioNeem), and in addition, the following compound: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006 / 043635) (CAS 885026-50-6), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (known from EP2647626) (CAS 1440516-42-6), PF1364 (known from JP2010 / 018586) (CAS 1204776-60-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one (known from WO2013 / 144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxide-3-thietanyl)benzamide (known from WO2013 / 050317A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide and (-)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide (known from WO2013 / 162715A2, WO2013 / 162716A2, US2014 / 0213448A1) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (known from CN101337937A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN103109816A) (CAS 1232543-85-9; N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO2012 / 034403A1) (CAS 1268277-22-0), 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 (known from WO2011 / 085575A1) (CAS 1233882-22-8), 4-[3-[2,6-Dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN101337940A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (known from CN101715774A) (CAS 1232543-85-9); 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylic acid ester (known from CN103524422A) (CAS 1542271-46-4;(4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN102391261A) (CAS 1370358-69-2);6-deoxy-3-O-ethyl-2,4-di-O-methyl-,1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-Triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose (known from US2014 / 0275503A1) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 1253850-56-4), (8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 933798-27-7), (8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (known from WO2007040280A1 and WO2007040282A1) (CAS 934001-66-8), N-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from CN103265527A) (CAS 1452877-50-7), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (known from WO2014 / 187846A1) (CAS 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-carboxylic acid ethyl ester (known from WO2010 / 066780A1, WO2011151146A1) (CAS 1229023-00-0), N-[1-(2,6-difluorophenyl)-1H-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from WO2014 / 053450A1) (CAS 1594624-87-9), N-[2-(2,6-difluorophenyl)-2H-1,2,3-triazol-4-yl]-2-(trifluoromethyl)benzamide (known from WO2014 / 053450A1) (CAS 1594637-65-6), N-[1-(3,5-difluoro-2-pyridinyl)-1H-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from WO2014 / 053450A1) (CAS 1594626-19-3), (3R)-3-(2-chloro-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo[3,2-a]pyrimidinium inner salt (known from WO2018 / 177970A1) (CAS 2246757-58-2; 3-(2-chloro-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo[3,2-a]pyrimidinium inner salt (known from WO2018 / 177970A1) (CAS 2246757-56-0); N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-2-(methylsulfonyl)-propanamide (known from WO2019 / 236274A1) (CAS 2396747-83-2), N-[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-2-fluoro-3-[(4-fluorobenzoyl)amino]-benzamide (known from WO2019059412A1) (CAS 1207977-87-4), 3-bromo-1-(3-chloro-2-pyridinyl)-N-[4, ,6-Dichloro-3-fluoro-2-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide (Fluchlorodiamide; known from CN110835330A, CN106977494A) (CAS: 2129147-03-9).

[0155] nematicides Active compounds identified herein by "common name" are known and can be found, for example, in the pesticide handbook ("The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) or on the internet (e.g., http: / / www.alanwood.net / pesticides). The classification is based on the Nematicide IRAC Mode of Action Classification Groups, current at the time of filing this patent application.

[0156] (Group N-1) Acetylcholinesterase (AChE) inhibitors, preferably (N-1A) Carbamates, selected from aldicarb, benfuracarb, carbofuran, carbosulfan and thiodicarb; or (N-1B) Organophosphate esters, which are selected from cadusafos, ethoprophos, fenamiphos, fosthiazate, imidiafos, phorate and terbufos.

[0157] (Group N-2) Glutamate-gated chloride channel (GluCl) allosteric modulators, preferably The avermectins are selected from abamectin and emamectin benzoate.

[0158] (Group N-3) Mitochondrial complex II electron transport inhibitors, in particular, succinate-coenzyme Q reductase inhibitors, preferably Pyridinylmethyl-benzamides, which are selected from fluopyram.

[0159] (Group N-4) Lipid synthesis / growth regulation modulators, in particular, inhibitors of acetyl-CoA carboxylase, preferably Tetronic acid derivatives and tetramic acid derivatives, which are selected from spirotetramates.

[0160] (Group N-UN) Compounds with unknown or unspecified mechanisms of action involving various chemical reactions, selected from fluensulfone, fluazaindolizine, furfural, iprodione and thioxazaphen.

[0161] (Group N-UNX) Compounds with unknown or unspecified mechanism of action: putative multi-site inhibitors, preferably a volatile sulfur-yielding agent selected from carbon disulfide and dimethyl disulfide (DMDS); or a carbon disulfide release promoter, which is selected from sodium tetrathiocarbonate; or an alkyl halide, selected from methyl bromide and methyl iodide (iodomethane); or a halogenated hydrocarbon selected from 1,2-dibromo-3-chloropropane (DBCP) and 1,3-dichloropropene; or Chloropicrin; or A methyl isothiocyanate generating agent, which is selected from allyl isothiocyanate, dazomet, metam potassium and metam sodium.

[0162] (Group N-UNB) bacterial agents with unknown or unspecified mechanism of action (non-Bt), preferably Bacteria or bacteria-derived bacteria, selected from: Burkholderia spp., for example Burkholderia rinojensis A396, Bacillus spp., for example Bacillus firmus, Bacillus licheniformis, Bacillus amyloliquefaciens or Bacillus subtilis, Pasteuria spp., for example Pasteuria penetrans or Pasteuria nishizawae, Pseudomonas spp. spp., for example Pseudomonas chlororaphis or Pseudomonas fluorescens, and Streptomyces spp., for example Streptomyces lydicus, Streptomyces dicklowii or Streptomyces albogriseolus.

[0163] (Group N-UNF) Fungal agents with unknown or unspecified mechanism of action, preferably Fungi or fungal-derived organisms, selected from: Actinomyces spp., for example Actinomyces streptococcus, Arthrobotrys spp., for example Arthrobotrys oligospora, Aspergillus spp., for example Aspergillus niger, Muscodor spp., for example Muscodor albus, Myrothecium spp., for example Myrothecium verrucaria, Paecilomyces spp. spp., for example, Paecilomyces lilacinus (Purpureocillium lilacinum), Paecilomyces carneus or Paecilomyces fumosoroseus, Pochonia spp., for example, Pochonia chlamydosporia, and Trichoderma spp., for example, Trichoderma harzianum, Trichoderma virens, Trichoderma atroviride or Trichoderma viride.

[0164] (Group N-UNE) Plant or animal derived active substances with unknown or unspecified mechanisms of action (this includes synthetic extracts and unrefined oils), preferably An agent of plant or animal origin selected from the following: azadirachtin, camellia oil cake, essential oils, garlic extract, pongamia oil, terpenes (e.g., carvacrol), and Quillaja saponaria extract.

[0165] disinfectant Active ingredients identified herein by "common name" are known and are described, for example, in "The Pesticide Manual (16th Ed. British Crop Protection Council)" or can be found on the internet (e.g., www.alanwood.net / pesticides ). All biocidal mixing partners named in classes (1) to (15) can also optionally form salts with suitable bases or acids, if their functional groups allow. All mixing partners named in classes (1) to (15) can also include tautomeric forms, if appropriate.

[0166] (1) Inhibitors of ergosterol biosynthesis, for example, (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenbuconazole, (1.005) fenhexamid, (1.006) fenpropidin, (1.007) fenpropimorph, (1.008) fenpyrazamine, (1.009) fluquinconazole, (1.010) flutriafol, (1.011) hexaconazole, (1.012) imazalil, (1.013) imazalil sulfate, (1.01 4) Ipconazole, (1.015) Ipfentrifluconazole, (1.016) Mefentrifluconazole, (1.017) Metconazole, (1.018) Myclobutanil, (1.019) Paclobutrazol, (1.020) Penconazole, (1.021) Prochloraz, (1.022) Propiconazole, (1.023) Prothioconazole, (1.024) Pyrisoxazole, (1.025) Spiroxamine, (1.026) Tebuconazole, (1.027) Tetraconazole, (1.028) Triazine Menol, (1.029) Tridemorph, (1.030) Triticonazole, (1.031) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.032) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.033) (2R)-2-(1-chlorocyclopropyl) -4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.034)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.035)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.036) (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.037) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.038) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1 -yl)propan-2-ol, (1.039)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.040)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.041)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, yl](pyridin-3-yl)methanol, (1.042) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.043) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.044) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.045) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.046) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.047) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy- 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4 -triazole-3-thione, (1.052) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.053) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.054) 2-[(2S,4S,5S)-1-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.055) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.056) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.057) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.058) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.059) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl yl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.060) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.061) 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, (1.062) 4-[[6-[rac- (2R)-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]-benzonitrile, (1.063) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.064) 5-(arylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxy]-benzonitrile, silan-2-yl]methyl}-1H-1,2,4-triazole, (1.065) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.066) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluoro-phenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.067) Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate, (1.068) N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.069) N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidoformamide, (1.070) N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)phenyl]- (1.071) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (1.072) N'-{5-bromo-2-methyl-6-[(1-propoxypropan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.073) N'-{5-bromo-6-[(1R)-1-(3,5-difluoromethyl)pyridin-3-yl]pyridin-3-yl}- (1.074) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.075) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, 1.076) N'-{5-bromo- 6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.077) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.078) N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methylimidoformamide.

[0167] (2) Inhibitors of the respiratory chain at complex I or complex II, such as (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) cyclobutrifluram, (2.006) fluveneteram, (2.007) fluindapyr, (2.008) fluopyram, (2.009) flutolanil, (2.010) fluxapyroxad, (2.011) furametpyr, (2.012) inpirfluxam, (2.013) isofetamide, (2.014) isoflucipram, (2.015) ) Isopyrazam, (2.016) Penflufen, (2.017) Penthiopyrad, (2.018) Pydiflumetofen, (2.019) Pyrapropoin, (2.020) Pyraziflumide, (2.021) Sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide , (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1 -methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.028) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.029) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.030) 3-(Difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.031) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.032) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.033) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.034) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-[rac-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide.

[0168] (3) Inhibitors of the respiratory chain in complex III, such as (3.001) ametoctrazine, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) fenpicoxamide, (3.012) florylpicoxamide, (3.013) Flufenoxystrobin, (3.014) Fluoxastrobin, (3.015) Kresoxim-methyl, (3.016) Mandestrobin, (3.014) Metominostrobin, (3.018) Methyltetraprole, (3.019) Orysastrobin, (3.020) Picoxystrobin, (3.021) Pyraclostrobin, (3.022) Pyrametstrobin, (3.023) Pyraoxystrobin, (3.024) Trifloxystrobin, (3.025) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-flu (3.026) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.027) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.028) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.031) methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate.

[0169] (4) Mitosis and cell division inhibitors, for example, (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) fluopimomide, (4.006) metrafenone, (4.007) pencycuron, (4.008) pyridaclomethyl, (4.009) pyriophenone (chlazafenone), (4.010) thiabendazole, (4.011) thiophanate-methyl, (4.012) zoxamide, (4.013) 3-chloro-5-( 4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.014) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)- (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.023) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.024) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.026) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.027) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.028) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.029) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.030) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.031) 4-(2-chloro-4-fluorophenyl)-N-(024) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.026) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.027) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.028) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

[0170] (5) Compounds capable of acting at multiple sites, for example (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper chloride dibasic, (5.009) copper(2+) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc zinc), (5.017) oxine copper, (5.018) propineb, (5.019) sulfur and sulfur agents, for example, calcium polysulfide, (5.020) thiuram, (5.021) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

[0171] (6) Compounds capable of inducing host defenses, such as (6.001) acibenzolar-S-methyl, (6.002) fosetyl-aluminium, (6.003) fosetyl-calcium, (6.004) fosetyl-sodium, (6.005) isotianil, (6.006) phosphorous acid and its salts, (6.003) probenazole, (6.004) tiadinil.

[0172] (7) Inhibitors of amino acid and / or protein biosynthesis, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil.

[0173] (8) Inhibitors of ATP production, for example, (8.001) silthiofam.

[0174] (9) Inhibitors of cell wall synthesis, for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamide, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[0175] (10) Inhibitors of lipid synthesis or transport or membrane synthesis, for example (10.001) fluoxapiproline, (10.002) natamycin, (10.003) oxathiapiproline, (10.004) propamocarb, (10.005) propamocarb hydrochloride, (10.006) propamocarb-fosetylate, (10.007) tolclofos-methyl, (10.008) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1 -yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (10.009) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (10.010) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(propan-2 -yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (10.011) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (10.012) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (10.013) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (10.014) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (10.015) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (10.016) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (10.017)014) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (10.015) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl Methanesulfonate, (10.016) 3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl Methanesulfonate, (10.017) 9-Fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl Methanesulfonate, (10.018) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (10.019) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate.

[0176] (11) Inhibitors of melanin biosynthesis, for example, (11.001) tolprocarb, (11.002) tricyclazole.

[0177] (12) Inhibitors of nucleic acid synthesis, such as (12.001) benalaxyl, (12.002) benalaxyl-M (chiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0178] (13) Signal transduction inhibitors, such as (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.

[0179] (14) Compounds that can act as uncouplers, for example, (14.001) fluazinam, (14.002) meptyldinocap.

[0180] (15) Further compounds, for example (15.001) abscisic acid, (15.002) aminopyrifen, (15.003) benthiazole, (15.004) bethoxadin, (15.005) capsimycin, (15.006) carvone, (15.007) chinomethionate, (15.008) khuflaneb, (15.009) cyflufenamid, (15.010) cymoxanil, (15.011) cyprosulfamide, (15.012) dipimethitrone, (15.013) fluthianil, (15.014) ipflufenamid Noxin, (15.015) Methyl isothiocyanate, (15.016) Mildiomycin, (15.017) Nickel dimethyldithiocarbamate, (15.018) Nitrothal-isopropyl, (15.019) Oxyfenthiin, (15.020) Pentachlorophenol and salts, (15.021) Picarburazox, (15.022) Quinofumelin, (15.023) D-Tagatose, (15.024) Tebufloquine, (15.025) Tecloftalam, (15.026) Tolnifanide nifanide), (15.027) 2-(6-benzylpyridin-2-yl)quinazoline, (15.028) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.029) 2-phenylphenol and salts, (15.030) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.031) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.032) 5-amino-1,3 ,4-Thiadiazole-2-thiol, (15.033) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide, (15.034) 5-fluoro-2-[(4-fluorobenzyl)oxy]-pyrimidin-4-amine, (15.035) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.036) 5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one, (15.037) But-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.038) Ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.039) Phenazine-1-carboxylic acid, (15.040) Propyl 3,4,5-trihydroxybenzoate, (15.041) Quinolin-8-ol, (15.042) Quinolin-8-ol Sulfate (2:1), (15.043) 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.044) 1-(5-(fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.045) 1-(5,6-dimethylpyridin-3-yl)- 4,4-Difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.046) 1-(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.047) 1-(6-(difluoromethyl)-5-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.0 48) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.049) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.050) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline phosphorus, (15.051) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-8-fluoroquinoline, (15.052) 3-(4,4-difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)quinoline, (15.053) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.054) 5-Bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline, (15.055) 8-Fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)-quinoline, (15.056) 8-Fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-quinoline, (15.057) 8-Fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline Quinoline-3-carboxamide, (15.058) 8-Fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3-carboxamide, (15.059) 9-Fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.060) N-(2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide, (15.061) N-[(2S)-2,4-dimethyl-1-phenyl [4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.062) 1,1-diethyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.063) 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.064) 1-[[3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl] methyl]azepan-2-one, (15.065) 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.066) 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.067) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.068) 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.069) 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, (15.070) 3,3-Dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.071) 3-Ethyl-1-methoxy-1-[[4-[5 -(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.072) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.073) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.074) 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl Dimethyl carbamate, (15.075) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.076) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.077) ethyl 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylate, (15.078) methyl{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate, (15.079) N-(1-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.080) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.081) N-(2-Fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.082) N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.083) N,N-Dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine, (15.084) N-[(E)- N-[(E)-N-Methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.085) N-[(E)-N-Methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.086) N-[(Z)-Methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.087) N-[(Z)-N-Methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide benzoimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.088) N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide, (15.089) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.090) N-[4-[5-(trifluoromethyl)-1,2 ,4-oxadiazol-3-yl]phenyl]cyclopropanecarboxamide, (15.091) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide, (15.092) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}cyclopropanecarboxamide, (15.093) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propanamide, (15.094) N-Allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide, (15.095) N-Allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.096) N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.097) N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.098) N. -Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.099) N-Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, (15.100) N-Methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide.

[0181] Biological pesticides as mixture components The compounds of formula (I) may be combined with a biological pesticide.

[0182] Biological pesticides include, inter alia, bacteria, fungi, yeasts, plant extracts and products formed by microorganisms (eg, proteins and secondary metabolites).

[0183] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.

[0184] Examples of such bacteria that have been or can be used as biological pesticides are: Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM I-1562, or Bacillus firmus strain I-1582 (accession number CNCM I-1582), or Bacillus pumilus, in particular strain GB34 (accession number ATCC 700814) and strain QST2808 (accession number NRRL B-30087), or Bacillus subtilis, in particular strain GB03 (accession number ATCC SD-1397), or Bacillus subtilis strain QST713 (accession number NRRL B-21661), or Bacillus subtilis strain OST 30002 (accession number NRRL B-50421), Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (antigenic type H-14) strain AM65-52 (accession number ATCC 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or Bacillus thuringiensis B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.Rotylenchulus reniformis nematode (nematode)-PR3 (accession number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (QRD 31.013, NRRL B-50550), and Streptomyces galbus strain AQ 6047 (accession number NRRL 30232).

[0185] Examples of fungi and yeasts that have been or can be used as biological pesticides are: Beauveria bassiana, in particular strain ATCC 74040, Coniothyrium minitans, in particular strain CON / M / 91-8 (accession number DSM-9660), Lecanicillium spp., in particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (now: Isaria fumosorosea), in particular the strain IFPC 200613 or the strain Apopka 97 (accession number ATCC 20874), Paecilomyces lilacinus, in particular the P. lilacinus strain 251 (AGAL 89 / 030550), Talaromyces flavus, in particular the strain V117b, Trichoderma atroviride, in particular the strain SC1 (accession number CBS 122089), Trichoderma harzianum, in particular the strain IFPC 200613 or the strain Apopka 97 (accession number ATCC 20874), harzianum), in particular Trichoderma harzianum rifai (T. harzianum rifai) T39 (accession number CNCM I-952).

[0186] Examples of viruses that have been or can be used as biological pesticides are: Smaller apple tortrix (Adoxophyes orana) granulosis virus (GV), codling moth (Cydia pomonella) granulosis virus (GV), cotton bollworm (Helicoverpa armigera) nuclear polyhedrosis virus (NPV), beet armyworm (Spodoptera exigua) mNPV, fall armyworm (Spodoptera frugiperda) mNPV, and African cotton leafworm (Spodoptera littoralis) NPV.

[0187] Also included are bacteria and fungi that are added as "inoculants" to plants or plant parts or plant organs and that, by virtue of their specific properties, promote plant growth and plant health. Examples that may be mentioned are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp. or Gigaspora monosporum, Glomus spp., Laccaria spp. spp.), Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.

[0188] Examples of plant extracts and products formed by microorganisms (including proteins and secondary metabolites) that have been or can be used as biological pesticides are: Garlic (Allium sativum), Wormwood (Artemisia absinthium), Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, American anthelminticum (Chenopodium anthelminticum), Chitin, Armour-Zen, Dryopteris filix-mas, Horsetail (Equisetum arvense), Fortune Aza, Fungastop, Heads Up (Quinoa (Chenopodium quinoa) Saponin Extract), Pyrethrum (Pyrethrum / Pyrethrins), Quassia amara, Quercus spp., Quillaja spp., Regalia, ("Requiem" TM Insecticide), rotenone, ryania / ryanodine, comfrey (Symphytum officinale), tansy (Tanacetum vulgare), thymol, Triact 70, TriCon, nasturtium (Tropaeulum majus), nettle (Urtica dioica), Veratrin, mistletoe (Viscum album), Brassicaceae extracts, in particular rapeseed powder or mustard powder, as well as bio-insecticidal / acaricidal active substances with carbon chain length C obtained from olive oil, in particular those contained as active ingredients, for example, in products with the trade name FLiPPER®. 16 -C 20 Unsaturated fats / carboxylic acids with

[0189] Safeners as blend components The compounds of formula (I) can be combined with safeners such as benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4), and the like.

[0190] Plants and plant parts All plants and plant parts can be treated according to the invention, where plants are understood to mean all plants and plant parts, such as desirable and undesirable wild plants or crop plants (including naturally occurring crop plants), such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, kidney beans, Brassica oleracea (e.g., cabbage) and other vegetable species, cotton, tobacco, rapeseed, and also fruit plants (fruit-bearing plants, apples, pears, citrus fruits, and grapevines). Crop plants may be plants obtainable by conventional breeding and optimization methods, or by biotechnological and genetic engineering methods, or by a combination of these methods. Such crop plants also include transgenic plants, as well as plant varieties that may or may not be protected by proprietary rights. Plants are understood to mean all developmental stages, from seeds, seedlings, and young plants (immature plants) to mature plants. Plant parts are understood to mean all parts and organs of the aboveground and underground parts of the plant, such as shoots, leaves, flowers, and roots. Examples include leaves, needles, stems, trunks, flowers, fruiting bodies, fruits, and seeds, as well as tubers, roots, and rhizomes. Plant parts also include harvested plants or harvested plant parts, as well as vegetative and generative propagation material, such as seedlings, tubers, rhizomes, cuttings and seeds.

[0191] The treatment of plants and plant parts with the compounds of formula (I) according to the invention is carried out by customary treatment methods, for example by immersion, spraying, vaporization, fogging, broadcasting, painting, injecting, etc., either directly or by applying the compounds to the surroundings, the environment or the storage space of the plants and plant parts, and also, in the case of propagation material, in particular seeds, by applying one or more coatings.

[0192] As already mentioned above, all plants and their parts can be treated according to the present invention. In a preferred embodiment, wild plant species and plant cultivars or plant species and cultivars obtained by conventional biological breeding methods, such as hybridization or protoplast fusion, and also their parts are treated. In yet another preferred embodiment, transgenic plants and plant cultivars (genetically modified organisms) and their parts obtained by genetic engineering methods, where appropriate in combination with conventional methods, are treated. The terms "parts" or "parts of plants" or "plant parts" have already been explained above. The present invention is particularly preferably used to treat plants of conventional cultivars that are commercially available or in use, respectively. Plant cultivars are understood to mean plants with new properties ("traits") obtained by conventional breeding or mutagenesis or recombinant DNA techniques. They can be cultivars, varieties, biotypes or genotypes.

[0193] Transgenic plants, seed treatments and integration events According to the present invention, compounds of formula (I) can be advantageously used to treat transgenic plants, plant cultivars, or plant parts that have received genetic material that confers advantageous and / or useful properties (traits) to those plants, plant cultivars, or plant parts. It is therefore contemplated that the present invention can be combined with one or more recombinant traits or transgenic events, or combinations thereof. For purposes of this application, a transgenic event is created by inserting a specific recombinant DNA molecule into a specific location (locus) within a chromosome of the plant genome. This insertion results in the formation of a novel DNA sequence, referred to as an "event," and is characterized by the inserted recombinant DNA molecule and a certain amount of genomic DNA adjacent to / flanking both ends of the inserted DNA. Such traits or transgenic events include, but are not limited to, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production and herbicide tolerance, where the trait is measured relative to a plant lacking such trait or transgenic event. Specific examples of such advantageous and / or useful properties (traits) are improved plant growth, vigor, stress tolerance, standability, lodging resistance, nutrient uptake, plant nutrition and / or yield, in particular improved growth, improved tolerance to high or low temperatures, improved tolerance to drought or water or soil salinity levels, enhanced flowering performance, improved ease of harvesting, accelerated maturation, increased yield, improved quality and / or improved nutritional value of the harvested product, improved shelf life and / or improved processability of the harvested product, and improved resistance or tolerance to harmful animals and microorganisms (e.g. insects, arachnids, nematodes, mites, slugs and snails).

[0194] Among the DNA sequences encoding proteins that confer resistance or tolerance to such pests, particularly insects, there may be mentioned in particular the genetic material from Bacillus thuringiensis that encodes the Bt proteins, which are widely described in the literature and well known to those skilled in the art, as well as proteins extracted from bacteria such as Photorhabdus (WO 97 / 17432 and WO 98 / 08932).In particular, the following may be mentioned: Bt Cry proteins or VIP proteins (which may include CryA, CryIAb, CryIAc, CryIIA, CryIIIA, CryIIIB2, Cry9c, and CryIF proteins) or toxic fragments thereof, and further hybrids or combinations thereof, in particular CrylF proteins or hybrids derived from CrylF proteins (e.g., hybrid CrylA-CrylF proteins or toxic fragments thereof), CrylA-type proteins or toxic fragments thereof, preferably CrylAc proteins or hybrids derived from CrylAc proteins (e.g., hybrid CrylAb-CrylAc proteins), or CrylAb or Bt2 proteins or toxic fragments thereof, Cry2Ae, Cry2Af or Cry2Ag proteins or toxic fragments thereof, CrylA.105 protein or toxic fragments thereof, VIP3Aa19 protein, VIP3Aa20 protein, VIP3A protein produced in COT202 or COT203 cotton events, Estruch et al. (1996), Proc Natl Acad Sci USA. 28;93(11):5389-94 or a toxic fragment thereof, the Cry protein described in WO2001 / 47952, an insecticidal protein from Xenorhabdus (described in WO98 / 50427), an insecticidal protein from Serratia (in particular the insecticidal protein from S. entomophila), or an insecticidal protein from a species of Photorhabdus, for example the Tc protein from Photorhabdus described in WO98 / 08932.Also encompassed herein are any variants or mutations of these proteins which differ by several amino acids (1 to 10, preferably 1 to 5) from the sequences listed above (especially the sequences of their toxic fragments) or which are fused to a signal peptide (e.g., a plastid signal peptide) or to another protein or peptide.

[0195] Another particularly important example of such a trait is the conferring of resistance to one or more herbicides (e.g., imidazolinones, sulfonylureas, glyphosate, or phosphinothricin). Among DNA sequences encoding proteins that confer the trait of resistance to a particular herbicide to transformed plant cells and plants, mention may be made in particular of the following: the bar gene or PAT gene described in WO 2009 / 152359, which confers resistance to the herbicide glufosinate, or the Streptomyces coelicolor gene, or a suitable EPSPS (e.g., α-glucan-2-phosphate dehydrogenase) gene, which confers resistance to herbicides targeting EPSPS (e.g., glyphosate and its salts). 5-enolpyruvylshikimate-3-phosphate synthase ), a gene encoding glyphosate-n-acetyltransferase, or a gene encoding glyphosate oxidoreductase. Additional suitable herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g., WO 2007 / 024782), a mutant Arabidopsis ALS / AHAS gene (e.g., U.S. Pat. No. 6,855,533), a gene encoding a 2,4-D-monooxygenase that confers tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid), and a gene encoding a dicamba monooxygenase that confers tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid).

[0196] Yet another particularly important example of such a trait is improved resistance to plant pathogenic fungi, bacteria and / or viruses, e.g., by systemic acquired resistance (SAR), systemin, phytoalexins, inducers and also resistance genes and the proteins and toxins expressed thereby.

[0197] Particularly useful transgenic events in transgenic plants or plant cultivars that can be preferably treated according to the invention include event 531 / PV-GHBK04 (cotton, insect control, described in WO 2002 / 040677), event 1143-14A (cotton, insect control, not deposited, described in WO 2006 / 128569); event 1143-51B (cotton, insect control, not deposited, described in WO 2006 / 128570); event 1445 (cotton, herbicide resistance, not deposited, described in US-A2002-120964 or WO 2002 / 034946); event 17053 (rice, herbicide resistance, deposited as PTA-9843, described in WO 2010 / 117737); event 17314 (rice, herbicide resistance, PTA-98 44, described in WO2010 / 117735); Event 281-24-236 (cotton, insect control - herbicide resistance, deposited as PTA-6233, described in WO2005 / 103266 or US-A2005-216969); Event 3006-210-23 (cotton, insect control - herbicide resistance, deposited as PTA-6233, described in US-A2007-143876 or WO200 5 / 103266); Event 3272 (maize, quality traits, deposited as PTA-9972, described in WO2006 / 098952 or US-A2006-230473); Event 33391 (wheat, herbicide resistance, deposited as PTA-2347, described in WO2002 / 027004), Event 40416 (maize, insect control - herbicide resistance, deposited as ATCC PTA-11508, described in WO11 / 075593); Event 43A47 (maize, insect control - herbicide resistance, deposited as ATCC PTA-11509, described in WO2011 / 075595); Event 5307 (maize, insect control, deposited as ATCC PTA-9561, described in WO2010 / 077816);Event ASR-368 (bentgrass, herbicide-resistant, deposited as ATCC PTA-4816, described in US-A2006-162007 or WO2004 / 053062); Event B16 (maize, herbicide-resistant, not deposited, described in US-A2003-126634); Event BPS-CV127-9 (soybean, herbicide-resistant, deposited as NCIMB No. 41603, described in WO2010 / 080829); Event BLR1 (oilseed rape, male sterility restoration, deposited as NCIMB 41193, described in WO2005 / 074671); Event CE43-67B (cotton, insect control, DSM ACC2724, described in US-A2009-217423 or WO2006 / 128573); Event CE44-69D (cotton, insect control, not deposited, described in US-A2010-0024077); Event CE44-69D (cotton, insect control, not deposited, described in WO2006 / 128571); Event CE46-02A (cotton, insect control, not deposited, described in WO2006 / 128572); Event COT102 (cotton, insect control, not deposited, described in US-A2006 -130175 or described in WO2004 / 039986); event COT202 (cotton, insect control, not deposited, described in US-A2007-067868 or WO2005 / 054479); event COT203 (cotton, insect control, not deposited, described in WO2005 / 054480); event DAS21606-3 / 1606 (soybean, herbicide resistance, deposited as PTA-11028, described in WO2012 / 033794), event DAS40278 (maize, herbicide resistance, deposited as ATCC PTA-10244, described in WO2011 / 022469);Event DAS-44406-6 / pDAB8264.44.06.l (soybean, herbicide-resistant, deposited as PTA-11336, described in WO2012 / 075426), Event DAS-14536-7 / pDAB8291.45.36.2 (soybean, herbicide-resistant, deposited as PTA-11335, described in WO2012 / 075429), Event DAS-59122-7 (maize, insect control-herbicide-resistant, deposited as ATCC PTA 11384, described in US-A2006-070139); Event DAS-59132 (maize, insect control-herbicide-resistant, not deposited, described in WO2009 / 100188); Event DAS68416 (soybean, herbicide-resistant, ATCC Event DP-098140-6 (maize, herbicide resistance, deposited as ATCC PTA-8296, described in US-A2009-137395 or WO08 / 112019); Event DP-305423-1 (soybean, quality traits, not deposited, described in US-A2008-312082 or WO2008 / 054747); Event DP-32138-1 (maize, hybridization line, deposited as ATCC PTA-9158, described in US-A2009-0210970 or WO2009 / 103049); Event DP-356043-5 (soybean, herbicide resistance, deposited as ATCC PTA-8287, described in US-A2010-0184079 or WO2008 / 002872); Event EE-I (eggplant, insect control, not deposited, described in WO07 / 091277); Event Fil 17 (maize, herbicide resistance, deposited as ATCC 209031, described in US-A2006-059581 or WO98 / 044140);Event FG72 (soybean, herbicide-resistant, deposited as PTA-11041, described in WO2011 / 063413), event GA21 (maize, herbicide-resistant, deposited as ATCC 209033, described in US-A2005-086719 or WO98 / 044140); event GG25 (maize, herbicide-resistant, deposited as ATCC 209032, described in US-A2005-188434 or WO98 / 044140); event GHB119 (cotton, insect control-herbicide-resistant, deposited as ATCC PTA-8398, described in WO2008 / 151780); event GHB614 (cotton, herbicide-resistant, deposited as ATCC PTA-6878, described in US-A2010-050282 or WO2007 / 017186); event GJ11 (maize, herbicide resistant, deposited as ATCC 209030, described in US-A2005-188434 or WO98 / 044140); event GM RZ13 (sugar beet, virus resistant, deposited as NCIMB-41601, described in WO2010 / 076212); event H7-1 (sugar beet, herbicide resistant, deposited as NCIMB 41158 or NCIMB 41159, described in US-A2004-172669 or WO2004 / 074492); event JOPLINl (wheat, disease resistant, not deposited, described in US-A2008-064032); event LL27 (soybean, herbicide resistant, deposited as NCIMB41658, described in WO2006 / 108674 or US-A2008-320616); event LL55 (soybean, herbicide resistant, deposited as NCIMB41660, described in WO2006 / 108675 or US-A2008-196127); event LLcotton25 (cotton, herbicide resistant, deposited as ATCC PTA-3343, described in WO2003 / 013224 or US-A2003-097687);Event LLRICE06 (rice, herbicide resistance, deposited under ATCC 203353, described in US 6,468,747 or WO2000 / 026345); event LLRice62 (rice, herbicide resistance, deposited under ATCC 203352, described in WO2000 / 026345); event LLRICE601 (rice, herbicide resistance, deposited under ATCC PTA-2600, described in US-A2008-2289060 or WO2000 / 026356); event LY038 (maize, quality traits, ATCC PTA-5623, described in US-A2007-028322 or WO2005 / 061720); event MIR162 (corn, insect control, deposited as PTA-8166, described in US-A2009-300784 or WO2007 / 142840); event MIR604 (corn, insect control, not deposited, described in US-A2008-167456 or WO2005 / 103301); event MON15985 (cotton, insect control, ATCC Event MON810 (maize, insect control, not deposited, described in US-A2002-102582); Event MON863 (maize, insect control, deposited as ATCC PTA-2605, described in WO2004 / 011601 or US-A2006-095986); Event MON87427 (maize, pollination control, deposited as ATCC PTA-7899, described in WO2011 / 062904); Event MON87460 (maize, stress tolerance, deposited as ATCC PTA-8910, described in WO2009 / 111263 or US-A2011-0138504); event MON87701 (soybean, insect control, deposited as ATCC PTA-8194, described in US-A2009-130071 or WO2009 / 064652);Event MON87705 (soybean, quality traits - herbicide tolerance, deposited as ATCC PTA-9241, described in US-A2010-0080887 or WO2010 / 037016); Event MON87708 (soybean, herbicide tolerance, deposited as ATCC PTA-9670, described in WO2011 / 034704); Event MON87712 (soybean, yield, deposited as PTA-10296, described in WO2012 / 051199), Event MON87754 (soybean, quality traits, deposited as ATCC PTA-9385, described in WO2010 / 024976); Event MON87769 (soybean, quality traits, ATCC PTA-8911, described in US-A2011-0067141 or WO2009 / 102873); event MON88017 (maize, insect control-herbicide resistant, deposited as ATCC PTA-5582, described in US-A2008-028482 or WO2005 / 059103); event MON88; 913 (cotton, herbicide-resistant, deposited as ATCC PTA-4854, described in WO2004 / 072235 or US-A2006-059590); event MON88302 (oilseed rape, herbicide-resistant, deposited as PTA-10955, described in WO2011 / 153186), event MON88701 (cotton, herbicide-resistant, deposited as PTA-11754, described in WO2012 / 134808), event MON89034 (maize, insect control, deposited as ATCC PTA-7455, described in WO07 / 140256 or US-A2008-260932); event MON89788 (soybean, herbicide-resistant, deposited as ATCC PTA-6708, described in US-A2006-282915 or WO2006 / 130436); event MS1 1 (oilseed rape, pollination control - herbicide resistant, deposited as ATCC PTA-850 or PTA-2485, described in WO2001 / 031042); event MS8 (oilseed rape, pollination control - herbicide resistant, deposited as ATCC PTA-730, described in WO2001 / 041558 or US-A2003-188347); event NK603 (maize, herbicide resistant, deposited as ATCC PTA-2478, described in US-A2007-292854); Event PE-7 (rice, insect control, not deposited, described in WO2008 / 114282); Event RF3 (oilseed rape, pollination control - herbicide resistance, ATCC PTA-730, described in WO2001 / 041558 or US-A2003-188347); event RT73 (oilseed rape, herbicide resistant, not deposited, described in WO2002 / 036831 or US-A2008-070260); event SYHT0H2 / SYN-000H2-5 (soybean, herbicide resistant, deposited as PTA-11226, described in WO2012 / 082548), event T227-1 (sugar beet, herbicide resistant, not deposited, described in WO2002 / 44407 or US-A2009-265817); event T25 (maize, herbicide resistant,Event T304-40 (cotton, insect control - herbicide resistance, deposited as ATCC PTA-8171, described in US-A2010-077501 or WO2008 / 122406); Event T342-142 (cotton, insect control, not deposited, described in WO2006 / 128568); Event TC1507 (maize, insect control - herbicide resistance, not deposited, described in US-A2005-039226 or WO2004 / 099447); Event VIP1034 (maize, insect control - herbicide resistance, deposited as ATCC Event 32316 (maize, insect control-herbicide resistant, deposited as PTA-11507, described in WO2011 / 084632), Event 4114 (maize, insect control-herbicide resistant, deposited as PTA-11506, described in WO2011 / 084621), Event EE-GM3 / FG72 (soybean, herbicide resistant, ATCC Accession No. PTA-11041) (which is optionally stacked with Event EE-GM1 / LL27 or Event EE-GM2 / LL55) (WO2011 / 063413A2), Event DAS-68416-4 (soybean, herbicide resistant, ATCC Accession No. PTA-10442, described in WO2011 / 063413A2), ... 11 / 066360Al), event DAS-68416-4 (soybean, herbicide resistance, ATCC accession number PTA-10442, WO2011 / 066384Al), event DP-040416-8 (maize, insect control, ATCC accession number PTA-11508, WO2011 / 075593Al), event DP-043A47-3 (maize, insect control, ATCC accession number PTA-11509, WO2011 / 075595Al), event DP-004114-3 (maize, insect control, ATCC accession number PTA-11506, WO2011 / 084621Al), event DP-032316-8 (maize, insect control, ATCC accession number PTA-11507, WO2011 / 084632Al), event MON-88302-9 (oilseed rape,Event DAS-21606-3 (soybean, herbicide tolerance, ATCC accession number PTA-10955, WO2011 / 153186A1), Event DAS-21606-3 (soybean, herbicide tolerance, ATCC accession number PTA-11028, WO2012 / 033794A2), Event MON-87712-4 (soybean, quality traits, ATCC accession number PTA-10296, WO2012 / 051199A2), Event DAS-44406-6 (soybean, stacked herbicide tolerance, ATCC accession number PTA-11336, W WO2012 / 075426Al), event DAS-14536-7 (soybean, stacked herbicide resistance, ATCC accession number PTA-11335, WO2012 / 075429Al), event SYN-000H2-5 (soybean, herbicide resistance, ATCC accession number PTA-11226, WO2012 / 082548A2), event DP-061061-7 (oilseed rape, herbicide resistance, accession number not available, WO2012071039Al), event DP-073496-4 (oilseed rape, herbicide resistance event 8264.44.06.1 (soybean, stacked herbicide resistance, accession number PTA-11336, WO2012075426A2), event 8291.45.36.2 (soybean, stacked herbicide resistance, accession number PTA-11335, WO2012075429A2), event SYHT0H2 (soybean, ATCC accession number PTA-11226, WO2012 / 082548A2), event MON88701 (soybean, stacked herbicide resistance, accession number PTA-113 ...MON88701 (soybean, stacked herbicide resistance, accession number PTA-11336, WO2012 / 082548A2), event SYHT0H2 (soybean, ATCC accession number PTA-11226, WO2012 / 082548A2), event MON88701 (soybean, stacked herbicide resistance, accession number PTA Event KK179-2 (alfalfa, ATCC accession number PTA-11754, WO2012 / 134808Al), event KK179-2 (alfalfa, ATCC accession number PTA-11833, WO2013 / 003558Al), event pDAB8264.42.32.1 (soybean, stacked herbicide resistance, ATCC accession number PTA-11993, WO2013 / 010094Al), event MZDT09Y (maize, ATCC accession number PTA-13025, WO2013 / 012775Al).

[0198] Additionally, a list of such transgenic events is provided by the United States Department of Agriculture (USDA) Animal and Plant Health Inspection Service (APHIS) and is available on the World Wide Web at their website: aphis.usda.gov ". For the purposes of this application, the status of that list as it exists / existed on the filing date of this application is relevant.

[0199] The genes / events that confer the desired traits can also be present in combination with each other in transgenic plants. Examples of transgenic plants that can be mentioned include important crop plants, such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peas and other types of vegetables, cotton, tobacco, rapeseed, and also fruit plants (fruit-bearing plants, apples, pears, citrus fruits and grapes), with corn, soybeans, wheat, rice, potatoes, cotton, sugarcane, tobacco and rapeseed being particularly important. Particularly important traits are improved plant resistance to insects, arachnids, nematodes, slugs and snails, and improved plant resistance to one or more herbicides.

[0200] Commercially available examples of such plants, plant parts or plant seeds which may preferably be treated according to the present invention include commercial products (e.g. plant seeds) sold or marketed under the following trade names: GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY®, VT DOUBLE PRO®, VT TRIPLE PRO®, BOLLGARD II®, ROUNDUP READY 2 YIELD®, YIELDGARD®, ROUNDUP READY 2® XTEN. DTM , INTACTA RR2 PRO®, VISTIVE GOLD®, and / or XTENDFLEXTM .

[0201] Crop protection - types of treatment The treatment of plants and plant parts with the compounds of formula (I) is carried out using customary treatment methods, for example by immersion, spraying, atomizing, irrigating, vaporizing, dusting, fogging, broadcasting, foaming, painting, spreading-on, injecting, watering (drenching), drip irrigation, etc., directly, or by applying the compounds to the surroundings, habitat or storage space of the plants and plant parts, and also in the case of propagation material, in particular seeds, as powders for dry seed treatment, solutions for liquid seed treatment, water-soluble powders for slurry treatment, by coating, by coating with one or more films, etc. Furthermore, the compounds of formula (I) can also be applied by ultra-low volume methods, or the application forms or the compounds of formula (I) themselves can be injected into the soil.

[0202] A preferred direct treatment of plants is foliar application (i.e., application of a compound of formula (I) to the foliage), in which case the frequency and rate of treatment should be adapted according to the level of infestation of the pest in question.

[0203] In the case of systemically active compounds, the compounds of formula (I) also reach plants via their root systems. In this case, the plants are treated by applying the compounds of formula (I) to the plant's habitat. This can be done, for example, by drenching, by mixing with the soil or nutrient solution (i.e., by impregnating the plant's growing area (for example, soil or a hydroponic system) with a liquid form of the compounds of formula (I)), by soil application (i.e., by introducing the compounds of formula (I) according to the invention in solid form (for example, in granular form) into the plant's growing area), or by drip application (often also called "chemigation") (i.e., by applying the compounds of formula (I) according to the invention together with varying amounts of water in liquid form to a defined location near the plant, from the ground surface or underground drip line, for a specific period of time). In the case of rice crops, this can also be done by metering a compound of formula (I) in solid application form (for example as granules) into flooded rice fields.

[0204] Digital Technology The compounds of the present invention can be used in combination with models, for example, models incorporated into computer programs for site-specific crop management, satellite farming, precision farming, or precision agriculture. Such models support site-specific management of agricultural fields using data from various sources, such as soil, weather, crops (e.g., type, growth stage, plant health), weeds (e.g., type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield, etc., with the aim of optimizing profitability, sustainability, and environmental protection. In particular, such models are useful for optimizing agronomic decisions, controlling the accuracy of pesticide application, and recording the work carried out.

[0205] As an example, if a model models pest infestation and calculates that a threshold has been reached at which it is recommended to apply a compound of the present invention to a crop plant, the compound of the present invention can be applied to the crop plant according to an appropriate dosing regimen.

[0206] Commercially available systems that include agronomic models include FieldScripts from The Climate Corporation. TM , Xarvio by BASF TM , AGLogic by John Deere TM etc.

[0207] The compounds of the present invention can also be used in combination with computerized spraying devices, such as spot spraying devices or precision spraying devices, attached to or housed in farm vehicles (e.g., tractors, robots, helicopters, airplanes, unmanned aerial vehicles (UAVs), e.g., drones, etc.). Such devices usually include an input sensor (e.g., a camera) and a processing device (configured to analyze input data and, based on the analysis of the input data, to provide a decision to apply the compounds of the present invention to crop plants (respectively, weeds) in a specific and precise manner). The use of such computerized spraying devices usually requires a location system (e.g., a GPS receiver) for locating the recorded data and for guiding or controlling the farm vehicle, a geographic information system (GIS) for displaying information on a clear map, and a suitable farm vehicle for carrying out the necessary agricultural work, such as spraying.

[0208] For example, pests can be detected from images captured by a camera. For example, the pests can be identified and / or classified based on the images. Such identification and / or classification can use image processing algorithms. Such image processing algorithms can utilize machine learning algorithms, such as trained neural networks, decision trees, and the like, and can utilize artificial intelligence algorithms. In this way, the compounds described herein can be applied only where needed.

[0209] Seed treatment Controlling pests by treating plant seeds has been known for a long time and has been continuously improved.However, seed treatment is accompanied by a series of problems that cannot always be solved satisfactorily.Therefore, it is desirable to develop a method for protecting seeds and germinating plants, which does not require or at least significantly reduces the need for additional application of pesticides during plant storage, after sowing or after emergence.In addition, it is also desirable to optimize the amount of active compound used, so that seeds and germinating plants are optimally protected from pest attack without causing damage to the plant itself by the active compound used.In particular, seed treatment methods should also take into account the intrinsic insecticidal or nematicidal properties of pest-resistant transgenic plants or pest-resistant transgenic plants, so as to achieve optimal seed protection using the minimum amount of pesticide, and also achieve optimal protection of germinating plants.

[0210] Therefore, the present invention also relates to a method for protecting seeds and germinating plants from attack by pests, in particular by treating the seeds with one of the compounds of formula (I). The method of the present invention for protecting seeds and germinating plants from attack by pests also includes a method in which the seeds are treated with the compound of formula (I) and the mixed components simultaneously or sequentially in one operation. It also includes a method in which the seeds are treated with the compound of formula (I) and the mixed components at different times.

[0211] The present invention further relates to the use of compounds of formula (I) for treating seeds to protect the seeds and the plants resulting from said seeds against pests.

[0212] The present invention also relates to seeds treated with a compound of formula (I) according to the present invention to protect against pests. The present invention also relates to seeds treated simultaneously with the compound of formula (I) and the mixture. The present invention also relates to seeds treated at different times with the compound of formula (I) and the mixture. When the seeds are treated at different times with the compound of formula (I) and the mixture, the individual substances may be present in different layers on the surface of the seed. In this case, the layers containing the compound of formula (I) and the mixture may optionally be separated by an intermediate layer. The present invention also relates to seeds to which the compound of formula (I) and the mixture are applied as components of a coating or as an additional layer or layers in addition to the coating.

[0213] Furthermore, the present invention also relates to seeds that have been treated with a compound of formula (I) and then subjected to a film coating process to prevent the seeds from being abraded by dust.

[0214] One advantage of the systemically acting compounds of formula (I) is the fact that by treating the seeds not only the seeds themselves are protected against pests but also the plants that result from them after emergence, thus avoiding the need to treat the crop directly at or shortly after sowing.

[0215] It should be regarded as a further advantage that by treating seeds with compounds of formula (I), the germination and emergence of the treated seeds may be enhanced.

[0216] It is also considered advantageous that the compounds of formula (I) can be used, in particular, also on transgenic seeds.

[0217] Additionally, compounds of formula (I) can be used in combination with signaling technology compositions or compounds to improve colonization by symbionts (e.g., rhizobia, mycorrhizal fungi, and / or endophytic bacteria or fungi) and / or optimize nitrogen fixation.

[0218] The compounds of formula (I) are suitable for protecting the seeds of all plant varieties used in agriculture, greenhouses, forests or horticulture.In particular, these are the seeds of cereals (e.g., wheat, barley, rye, millet and oats), corn, cotton, soybeans, rice, potatoes, sunflowers, coffee, tobacco, canola, rapeseed, beets (e.g., sugar beets and fodder beets), peanuts, vegetables (e.g., tomatoes, cucumbers, beans, cruciferous vegetables, onions and lettuce), fruit plants, turf and ornamental plants.It is particularly important to treat the seeds of cereals (e.g., wheat, barley, rye and oats), corn, soybeans, cotton, canola, rapeseed, vegetables and rice.

[0219] As already mentioned above, the treatment of transgenic seeds with compounds of formula (I) is also particularly important. These are seeds of plants that generally contain at least one heterologous gene controlling the expression of a polypeptide with insecticidal and / or nematicidal properties. These heterologous genes in transgenic seeds can be derived from microorganisms such as Bacillus species, Rhizobium species, Pseudomonas species, Serratia species, Trichoderma species, Clavibacter species, Glomus species, or Gliocladium species. The present invention is particularly suitable for treating transgenic seeds containing at least one heterologous gene derived from Bacillus species. It is particularly preferred that the heterologous gene be derived from Bacillus thuringiensis.

[0220] In the context of the present invention, the compound of formula (I) is applied to seeds. Preferably, the seeds are treated in a state sufficiently stable to avoid damage during treatment. Generally, the seeds can be treated at any time between harvesting and sowing. The seeds generally used are separated from the plant and have had the cob, husk, petiole, husk, hair, or pulp removed. For example, seeds that have been harvested, cleaned, and dried to a moisture content that allows storage can be used. Alternatively, seeds that have been treated with, for example, water after drying and then dried again (e.g., primed) can also be used. In the case of rice seeds, seeds that have been soaked, for example, in water, until they reach a certain stage of the rice embryo (pigeon breast stage) can also be used, which stimulates germination and makes emergence more uniform.

[0221] When treating seeds, care must generally be taken to select the amount of compound of formula (I) and / or the amount of further additives applied to the seeds so that seed germination is not adversely affected or the resulting plants are not damaged. This must be ensured, in particular, in the case of active compounds that may exhibit phytotoxic effects at certain application rates.

[0222] Generally, the compounds of formula (I) are applied to the seeds in a suitable formulation. Suitable formulations and methods for treating seeds are known to those skilled in the art.

[0223] The compounds of formula (I) can be converted into conventional seed dressing formulations, such as solutions, emulsions, suspensions, dusts, foams, slurries or other coating compositions for seeds, and can also be converted into ULV formulations.

[0224] These formulations are prepared in known manner by mixing the compounds of formula (I) with customary additives, such as customary extenders and further solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins, etc., and further mixing with water.

[0225] Colorants that can be present in the seed dressing formulations that can be used according to the invention are all colorants that are customary for such purposes. Pigments that are poorly soluble in water or dyes that are soluble in water can be used. Examples include the colorants known under the names "Rhodamin B," "CI Pigment Red 112," and "CI Solvent Red 1."

[0226] Useful wetting agents that can be present in the seed dressing formulations that can be used according to the invention are all substances that promote wetting that are customarily used in the formulation of agrochemically active compounds. Preferably, alkylnaphthalenesulfonates, such as diisopropylnaphthalenesulfonate or diisobutylnaphthalenesulfonate, are used.

[0227] Useful dispersants and / or emulsifiers that can be present in the seed dressing formulations usable in accordance with the present invention include all nonionic, anionic, and cationic dispersants customarily used in formulating pesticide active ingredients. Preferably, nonionic or anionic dispersants or mixtures of nonionic and anionic dispersants are used. Suitable nonionic dispersants include, in particular, ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers, and tristryrylphenol polyglycol ethers, as well as their phosphorylated or sulfated derivatives. Suitable anionic dispersants include, in particular, lignosulfonates, polyacrylates, and arylsulfonate / formaldehyde condensates.

[0228] Antifoaming agents that can be present in the seed dressing formulations that can be used according to the invention are all foam-inhibiting substances that are customarily used for the formulation of pesticide active ingredients. Preferably, silicone antifoaming agents and magnesium stearate are used.

[0229] Preservatives that can be present in the seed dressing formulations that can be used according to the invention are all substances that can be used for this purpose in pesticide compositions, such as dichlorophene and benzyl alcohol hemiformal.

[0230] Secondary thickeners that may be present in the seed dressing formulations that can be used according to the invention are all substances that can be used for this purpose in agrochemical compositions, with cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and micronized silica being preferred.

[0231] Adhesives that can be present in the seed dressing formulations that can be used according to the invention are all conventional binders that can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

[0232] Gibberellins that can be present in the seed dressing formulations that can be used according to the invention are preferably gibberellin A1, gibberellin A3 (=gibberellic acid), gibberellin A4 and gibberellin A7; particularly preferably, gibberellic acid is used. Gibberellins are known (cf. R. Wegler "Chemie der Pflanzenschutz- and Schadlingsbekampfungsmittel", Vol. 2, Springer Verlag, 1970, pp. 401-412).

[0233] The seed dressing formulations usable in accordance with the present invention can be used directly or after dilution with water to treat a wide variety of seeds. For example, concentrates or preparations obtainable from concentrates by dilution with water can be used to dress cereal seeds, such as wheat, barley, rye, oats, and triticale, as well as corn, rice, rapeseed, peas, kidney beans, cotton, sunflowers, soybeans, and beets, or to dress a wide variety of vegetable seeds. The seed dressing formulations usable in accordance with the present invention or their diluted application forms can also be used to dress the seeds of transgenic plants.

[0234] When treating seeds with the seed dressing formulation usable according to the present invention or the application form prepared by adding water from the seed dressing formulation, all mixing devices that are conventionally used for seed dressing are useful. Specifically, the procedure for seed dressing is to place seeds in a mixer (which can be operated batchwise or continuously), add the desired amount of seed dressing formulation either directly or after diluting it with water, and mix everything until the formulation is evenly distributed on the surface of the seeds. If appropriate, a drying process is then carried out.

[0235] The application rate of the seed dressing formulations that can be used according to the present invention can vary within a relatively wide range, depending on the specific content of the compound of formula (I) in the formulation and the seed. The application rate of the compound of formula (I) is generally 0.001 to 50 g per kg of seeds, preferably 0.01 to 15 g per kg of seeds.

[0236] animal health In the field of animal health, i.e., veterinary medicine, the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term "endoparasites" includes in particular helminths and protozoans (e.g., coccidia). Ectoparasites are typically and preferably arthropods, in particular insects or mites.

[0237] In the field of veterinary medicine, the compounds of formula (I) which have a favorable degree of toxicity to warm-blooded animals are suitable in animal breeding and animal husbandry for controlling parasites which occur in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals, and they are active against all or specific developmental stages of the parasites.

[0238] Agricultural livestock may, for example, include mammals, such as sheep, goats, horses, donkeys, camels, water buffalo, rabbits, reindeer, fallow deer, and in particular cattle and pigs; or poultry, such as turkeys, ducks, geese, and in particular chickens; or fish or crustaceans, for example fish or crustaceans in aquaculture; or possibly insects, such as bees.

[0239] Domestic animals may include, for example: mammals, such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and, in particular, dogs, cats; caged birds; reptiles; amphibians; or aquarium fish.

[0240] In certain embodiments, a compound of Formula (I) is administered to a mammal.

[0241] In another particular embodiment, the compounds of formula (I) are administered to birds, ie to caged birds, or, in particular, poultry.

[0242] The use of the compounds of formula (I) to control animal parasites is intended to reduce or prevent illness, death, and loss of performance (meat, milk, wool, leather, eggs, honey, etc.) in the animals, resulting in more economical and easier animal rearing and better animal health.

[0243] The terms "control" or "controlling," as used herein in the context of the animal health field, mean that the compounds of formula (I) are effective in reducing the incidence of individual parasites in infected animals to harmless levels. More specifically, "control," as used herein, means that the compounds of formula (I) are effective in killing, inhibiting the growth of, or inhibiting the proliferation of individual parasites.

[0244] Representative arthropods include, but are not limited to: from the order Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example, Bovicola spp., Damalina spp., Felicola spp.; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp.; From the order Diptera and the suborder Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp. spp.), Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp., Odagmia spp. spp.), Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.; From the order Siphonapterida, for example, Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.; From the order Heteropterida, for example, Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp.; and harmful and hygiene pests from the order Blattaria.

[0245] Furthermore, among arthropods, examples that may be mentioned include, but are not limited to, the following mites: From the subclass Acari (Acarina) and the order Metastigmata, for example from the family Argasidae, for example Argas spp., Ornithodorus spp., Otobius spp., from the family Ixodidae, for example Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp. spp.), Rhipicephalus spp. (the original genus of multi-host mites); from the order Mesostigmata, for example, Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilelaps spp., Varroa spp.; from the order Actinedida (Prostigmata), for example, Acarapis spp., Cheyletiella spp. spp.), Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp.; and from the order Acaridida (Astigmata), for example, Acarus spp., Caloglyphus spp., Chorioptes spp.), Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp..

[0246] Representative parasitic protozoa include, but are not limited to: Mastigophora (Flagellata), for example: Metamonada: of the order Diplomonadida, e.g., Giardia spp., Spironucleus spp.; Parabasala: from the order Trichomonadida, for example, Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.; Euglenozoa: from the order Trypanosomatida, e.g., Leishmania spp., Trypanosoma spp.; the subphylum Sarcomastigophora (class Rhizopoda), for example, the family Entamoebidae, for example Entamoeba spp., the family Centramoebidae, for example Acanthamoeba spp., the family Euamoebidae, for example Hartmanella spp.; Alveolata, for example, Apicomplexa (Sporozoa), for example, Cryptosporidium spp.; from the order of the Eimeriida, for example, Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; from the order of the Adeleida, for example, Hepatozoon spp., Klossiella spp.; from the order of the Haemosporida, for example, Leucocytozoon spp., Plasmodium spp.; from the order of the Piroplasmida, for example, Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; from the order of the Vesibuliferida, for example, Balantidium spp., Buxtonella spp.; Microspora, for example Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., and also, for example, Myxozoa spp.

[0247] Helminths that are pathogenic to humans or animals include, for example, Acanthocephala, Nematoda, Pentastoma, and Platyhelminths (e.g., Monogenea, Cestodes, and Trematodes).

[0248] Representative helminths include, but are not limited to: Monogenea: for example: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglocephalus spp.; Cestodes: from the order Pseudophyllidea, for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp., Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.; From the order of the Cyclophyllida, for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp. spp.), Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.; Trematodes: from the subclass Digenea, for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp., Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp. spp.), Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp. spp.), Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp.), Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.;. Nematodes: from the order Trichinellida, for example: Capillaria spp., Eucoleus spp., Paracapillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.; From the order Tylenchida, for example: Micronema spp., Parastrongyloides spp., Strongyloides spp.; From the order of the Rhabditina, for example: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp. spp.), Cyclodontostomum spp., Cyclocercus spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp. spp.), Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp.), Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paraclenosoma spp., Parafilaroides spp., Parelaphostrongylus spp. spp.), Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp. spp.), Troglostrongylus spp., Uncinaria spp.;. From the order of the Spirurida, for example: Acanthocheilonema spp., Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp. spp.); Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp. spp.), Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp., Stephanofilaria spp., Strongyluris spp.), Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp.;. Acantocephala: from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp.; from the order Moniliformida, for example: Moniliformis spp.; From the order of the Polymorphida, for example: Filicollis spp.; From the order of the Echinorhynchida, for example: Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.; Phylum Pentastoma: Order Porocephalida, for example, Linguatula spp.

[0249] In the field of veterinary medicine and animal husbandry, the administration of the compounds of formula (I) is carried out by methods generally known in the art, for example, enterally, parenterally, transdermally or intranasally in the form of suitable preparations. Administration can be carried out prophylactically, methaphylactically or therapeutically.

[0250] Thus, one embodiment of the present invention relates to a compound of formula (I) for use as a medicament.

[0251] Another aspect relates to compounds of formula (I) for use as antiendoparasitical agents.

[0252] Another particular embodiment relates to compounds of formula (I) for use as antihelmintic agents, more particularly as nematicides, platyhelminthicidal agents, acanthocephalicidal agents or pentastomicidal agents.

[0253] Another particular embodiment relates to compounds of formula (I) for use as antiprotozoal agents.

[0254] Another aspect relates to compounds of formula (I) for use as antiectoparasitical agents, in particular for use as arthropodicidal agents, more particularly for use as insecticides or acaricides.

[0255] A further aspect of the invention is a veterinary formulation comprising an effective amount of at least one compound of formula (I) and at least one of the following: a pharmaceutically acceptable excipient (e.g. a solid or liquid diluent), a pharmaceutically acceptable adjuvant (e.g. a surfactant), in particular a pharmaceutically acceptable excipient customarily used in veterinary formulations, and / or a pharmaceutically acceptable adjuvant customarily used in veterinary formulations.

[0256] A related aspect of the invention is a method for preparing the veterinary formulations described herein, which method comprises mixing at least one compound of formula (I) with a pharmaceutically acceptable excipient and / or adjuvant (in particular a pharmaceutically acceptable excipient customarily used in veterinary formulations and / or a pharmaceutically acceptable adjuvant customarily used in veterinary formulations).

[0257] Another particular aspect of the present invention is a veterinary formulation selected from the group of the ectoparasiticidal and endoparasiticidal formulations according to the above aspects, more particularly a veterinary formulation selected from the group of anthelmintic formulations, antiprotozoal formulations and arthropodicidal formulations, even more particularly a veterinary formulation selected from the group of nematicide formulations, platyhelminthicidal formulations, acanthocephalicidal formulations, pentastomicidal formulations, insecticide formulations and acaricide formulations, and methods for preparing them.

[0258] Another aspect relates to a method of treating parasitic infections, particularly infections by parasites selected from the group of ectoparasites and endoparasites described herein, by administering to an animal (particularly a non-human animal) in need of such treatment an effective amount of a compound of formula (I).

[0259] Another aspect relates to a method of treating a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites described herein, by administering to an animal (in particular a non-human animal) in need of such treatment a veterinary formulation as defined herein.

[0260] Another aspect relates to the use of compounds of formula (I) in the treatment of parasitic infections in animals (particularly non-human animals), particularly infections caused by parasites selected from the group of ectoparasites and endoparasites described herein.

[0261] In relation to the field of animal health or veterinary medicine, the term "treatment" includes prophylactic, metaphylactic or therapeutic treatment.

[0262] In certain embodiments, the veterinary field is provided with a mixture of at least one compound of formula (I) with another active ingredient, particularly an endoparasiticide and an ectoparasiticide.

[0263] In the field of animal health, "mixture" does not only mean that two (or more) different active ingredients are formulated into a common formulation and then applied together, but also means a product that contains an independent formulation for each active compound.Therefore, when three or more active compounds are applied, all active compounds can be formulated into a common formulation, or all active compounds can be formulated into separate formulations; also, a mixed form in which some active compounds are formulated together and some active compounds are formulated separately is possible.In separate formulations, the active compounds can be applied separately or sequentially.

[0264] The active compounds identified herein by "common name" are known and are described, for example, in the Pesticide Manual (see above) or can be found on the internet (e.g., http: / / www.alanwood.net / pesticides).

[0265] Representative active ingredients selected from the ectoparasiticide group as a mixture partner include, but are not limited to, the insecticides and acaricides described in detail above. Additional active ingredients that can be used are listed below according to the above classification based on the current "IRAC Mode of Action Classification Scheme": (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) nicotinic acetylcholine receptor (nAChR) competitive modulators; (5) nicotinic acetylcholine receptor (nAChR) allosteric modulators; (6) glutamate-controlled chloride channel (GluCl) allosteric modulators; (7) juvenile hormone mimetics; (8) various unspecified (multi-site) inhibitors; (9) chordotonal organ modulators; (10) mite growth inhibitors; (12) mitochondrial ATP synthase inhibitors, e.g., ATP disruptors; (13) proton gradient inhibitors. (14) nicotinic acetylcholine receptor channel blockers; (15) chitin biosynthesis inhibitors (type 0); (16) chitin biosynthesis inhibitors (type 1); (17) molting disruptors (especially for Diptera (i.e., Diptera)); (18) ecdysone receptor agonists; (19) octopamine receptor agonists; (21) mitochondrial complex I electron transport inhibitors; (25) mitochondrial complex II electron transport inhibitors; (20) mitochondrial complex III electron transport inhibitors; (22) voltage-gated sodium channel blockers; (23) inhibitors of acetyl-CoA carboxylase; (28) ryanodine receptor modulators; and (30) GABA-regulated chloride channel allosteric modulators.

[0266] Active compounds with unknown or unspecified mechanism of action, for example, fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, chinomethionate, triatene, clothiazoben, tetrasul, potassium oleate, petroleum, methoxadiazone, gossypurle, flutenzin, bromopropylate, cryolite;

[0267] Another class of compounds: Butacarb, Dimethilan, Cloetocarb, Phosphocarb, Pirimiphos (-ethyl), Parathion (-ethyl), Methacrifos, Isopropyl o-salicylate, Trichlorfon, Sulprofos, Propaphos, Cebufos, Pyridathione, Protoate, Diclofenthion, Demeton-S-methylsulfone, Isazophos, Cyanofenphos, Dialifos, Carbophenothion, Autathiofos, Allomfenvinphos (-methyl), Azinphos (-ethyl), Chlorpyrifos (-ethyl), Fosmetilan, Iodofenphos, Dioxabenzophos, Formothion, Fonofos, Flupyrazophos, Fensulfothion, Etrimphos; Organochlorine compounds, such as camphechlor, lindane, heptachlor; Phenylpyrazoles, such as acetoprole, pyrafluprole, pyriprole, vaniliprole, cisapronil; Isoxazolines, such as afoxolaner, fluralaner, lotilaner, sarolaner; Pyrazolyl-arylamides, for example, nicofluprole, tigolaner; Pyrethroids, such as (cis-, trans-)metofluthrin, profluthrin, flufenprox, flubrocythrinate, fubufenprox, fenfluthrin, protrifenbut, pyresmethrin, RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin, clocithrin, cyhalothrin (lambda-), clovaporthrin, or halogenated hydrocarbons (HCHs); Neonicotinoids, for example, nithiazine; Dichloromezotiaz, triflumezopyrim; Macrocyclic lactones, such as nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin oxime; Triplene, epofenonane, diofenolan; Biological agents, hormones, or pheromones, such as natural products, e.g., thuringiensin, codlemone, or neem components; Dinitrophenols, such as dinocap, dinobuton, binapacryl; Benzoylureas, for example, fluazuron, penfluron; Amidine derivatives, such as chlormebuform, cymiazole, demiditraz; Beehive varroa acaricides, for example, organic acids, e.g., formic acid, oxalic acid.

[0268] Representative active ingredients selected from the group of endoparasitic agents as mixing partners include, but are not limited to, anthelmintic active compounds and antiprotozoal active compounds.

[0269] The anthelmintic active compounds may include, but are not limited to, the following nematicidal, flukecidal and / or cestocidal compounds: From the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin, milbemycin; From the class of the benzimidazoles and probenzimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flubendazole; From the class of the depsipeptides, preferably from the class of the cyclic depsipeptides, in particular from the class of the 24-membered cyclic depsipeptides, for example: emodepside, PF1022A; From the class of the tetrahydropyrimidines, for example: morantel, pyrantel, oxantel; From the class of imidazothiazoles, for example: butamisole, levamisole, tetramisole; From the class of aminophenylamidines, for example: amidantel, deacylated amidantel (dAMD), tribendimidine; From the class of the aminoacetonitriles, for example: monepantel; From the class of the paraherquamides, for example: paraherquamide, delquantel; From the class of the salicylanilides, for example: tribromsalan, bromoxanide, brothianide, clioxanide, closantel, niclosamide, oxyclozanide, lafoxanide; From the class of substituted phenols, for example: nitroxynil, bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan; From the class of organophosphates, for example: trichlorfon, naphthalofos, dichlorvos / DDVP, crufomate, coumaphos, haloxon; From the class of the piperazinones / quinolines, for example: praziquantel, epsiprantel; From the class of piperazines, for example: piperazine, hydroxyzine; From the class of tetracyclines, for example: tetracycline, chlortetracycline, doxycycline, oxytetracycline, rolitetracycline; From various other classes, for example: bunamidine, niridazole, resorantel, omfalotin, oltipraz, nitroscanate, nitroxynil, oxamniquine, mirasan, miracil, lucanthone, hycanthone, hetolin, emetine, diethylcarbamazine, dichlorophene, diamfenetide, clonazepam, bephenium, amoscanate, clorsulon.

[0270] Antiprotozoal active compounds include, but are not limited to, the following active compounds: From the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; From the class of polyether ionophores, for example: monensin, salinomycin, maduramycin, narasin; From the class of macrocyclic lactones, for example: milbemycin, erythromycin; From the class of quinolones, for example: enrofloxacin, pradofloxacin; From the class of quinines, for example: chloroquine; From the class of pyrimidines, for example: pyrimethamine; From the class of sulfonamides, for example: sulfaquinoxaline, trimethoprim, sulfaclozine; From the class of thiamines, for example: amprolium; From the class of lincosamides, for example: clindamycin; From the class of carbanilides, for example: imidocarb; From the class of nitrofurans, for example: nifurtimox; From the class of quinazolinone alkaloids, for example: halofuginone; Of various different classes, for example: oxamniquine, paromomycin; From the class of vaccines or microbial antigens, for example: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus.

[0271] All named mixing partners, if their functional groups allow, can optionally form salts with suitable bases or acids.

[0272] Vector control The compounds of formula (I) can also be used in the control of vectors. For the purposes of the present invention, vectors are arthropods (e.g., insects or arachnids) capable of transporting pathogens (e.g., viruses, worms, single-celled organisms, and bacteria) from a reservoir (e.g., plant, animal, human) to the host. The pathogens can be transported to the host mechanically (e.g., trachoma by non-biting flies) or by injection into the host (e.g., malaria parasites by mosquitoes).

[0273] Examples of vectors and the diseases or pathogens they carry are: (1) Mosquitoes Anopheles mosquitoes: malaria, filariasis; Culex mosquitoes: Carrying Japanese encephalitis, other viral diseases, filariasis, and other helminths; Aedes mosquitoes: yellow fever, dengue fever, other viral diseases, filariasis; Black flies (Simuliidae): Carrying helminths (especially Onchocerca volvulus); · House flies (Psychodidae): transmission of leishmaniasis; (2) Lice: skin infections, epidemic typhus; (3) Fleas: contagious diseases, typhus, tapeworms; (4) Flies: sleeping sickness (trypanosomiasis); cholera, another bacterial disease; (5) Ticks: Acariosis, epidemic typhus, rickettsial smallpox, tularemia, St. Louis encephalitis, tick-borne encephalitis (TBE), Crimean-Congo hemorrhagic fever, borreliosis; (6) Ixodid ticks: borellioses, e.g., Lyme disease Borrelia (Borrelia burgdorferi sensu lato), Dutton's relapsing fever Borrelia (Borrelia duttoni), tick-borne encephalitis, Q fever (Coxiella burnetii), babesiosis (Babesia canis canis), ehrlichiosis.

[0274] In the sense of the present invention, examples of vectors are insects capable of transmitting plant viruses to plants, such as aphids, flies, leafhoppers or thrips. Further vectors capable of transmitting plant viruses are spider mites, lice, beetles and nematodes.

[0275] Further examples of vectors within the meaning of the present invention are insects and arachnids capable of transmitting pathogens to animals and / or humans, such as mosquitoes (in particular Aedes mosquitoes, Anopheles mosquitoes, such as A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex mosquitoes), psychodids, such as Phlebotomus sandflies, Lutzomyia, lice, fleas, flies, mites and ticks.

[0276] If the compounds of formula (I) are resistance-breaking, vector control is likewise possible.

[0277] The compounds of formula (I) are suitable for use in the prevention of diseases and / or vector-borne pathogens. Thus, a further aspect of the invention is the use of compounds of formula (I) for controlling vectors, for example in agriculture, in horticulture, in gardens and leisure facilities, and also in the protection of materials and stored products.

[0278] Protection of industrial materials The compounds of formula (I) are suitable for protecting industrial materials against attack or destruction by insects (e.g. insects of the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma).

[0279] In the context of the present invention, industrial materials are understood to mean non-living materials such as, preferably, plastics, adhesives, sizes, paper and cardboard, leather, wood, engineered wood products and paints, etc. The present invention is particularly preferably used for protecting wood.

[0280] In a further embodiment, the compounds of formula (I) are used together with at least one further insecticide and / or at least one fungicide.

[0281] In a further embodiment, the compounds of formula (I) are present as ready-to-use pesticides, i.e., they can be applied to the material without further modification. Suitable additional insecticides or fungicides are, in particular, those listed above.

[0282] It has also been found, surprisingly, that the compounds of formula (I) can be used to protect against fouling items that come into contact with seawater or brackish water, in particular ship hulls, screens, nets, buildings, mooring equipment, signaling systems, etc. Likewise, the compounds of formula (I) can be used as antifouling agents, either alone or in combination with other active compounds.

[0283] Pest control in the sanitation sector The compounds of formula (I) are suitable for controlling pests in the hygiene field.In particular, the present invention can be applied in the home field, hygiene field, and in the protection of stored products, especially to control insects, arachnids, ticks and mites encountered in enclosed spaces (for example, dwellings, factory corridors, offices, vehicle compartments, livestock farming).To control pests, the compounds of formula (I) are used alone or in combination with other active compounds and / or adjuvants.They are preferably used in household insecticide products.The compounds of formula (I) are effective against sensitive and resistant species, and are also effective against all developmental stages.

[0284] These pests include, for example, pests from the orders Scorpiones, Araneae and Opiliones of the class Arachnida, pests from the classes Chilopoda and Diplopoda, pests from the classes Insecta such as Blattodea, Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Examples include pests of the orders Orthoptera, Siphonaptera and Zygentoma, as well as pests of the order Isopoda in the class Malacostraca.

[0285] They are used, for example, in aerosols, non-pressurized spray products such as pump sprays and atomizing sprays, automatic fogging systems, foggers, foams, gels, evaporator products with cellulose or plastic evaporator tablets, liquid evaporators, gel and film evaporators, propeller-driven evaporators, energy-free or passive evaporation systems, moth papers, moth bags and moth gels, or as granules or dusts, in broadcast baits or in bait stations.

[0286] [Table 1] TIFF2024516278000020.tif119158

[0287] Description of preparation methods and intermediates Compounds of formula (I) can be prepared as illustrated in Scheme 1 below, where X is O and R 1 is H, and A 1 , A 2 , A 3 , A 4 , R 2 , R 3 , R 4 , R 5 is as defined above, PG is an amino protecting group, Hal is fluorine, chlorine, bromine or iodine, and Q 1 , Q 2 is hydroxy or chlorine.

[0288] Scheme 1 [ka]

[0289] As shown in Scheme 1, the introduction of the heterocyclic amine group can be carried out by aromatic nucleophilic substitution of the halogen of nitroazine (1) with heterocyclic amine (2) in the presence of a base such as CsCO or pyridine in various solvents such as acetonitrile, DMF, dioxane, or THF. Alternatively, the heterocyclic amine can be introduced by Buchwald reaction conditions using various palladium catalysts and appropriate ligands, such as those described in US 2010 / 29638 A1 or WO 2012 / 41476 A1. In the subsequent reaction, reduction of the nitro group can be achieved by various reduction methods, such as hydrogen / Pd—C, SnCl dihydrate, or iron / NH Cl, according to methods known in the art. The resulting amine derivative (4) can be further converted to a methyl group by using conventional coupling reagents such as HATU / DIPEA, or by first converting the methyl group to an amino acid (5Q). 1 =OH) to the corresponding reactive mixed acid anhydrides using, for example, chloroformate and N-methylmorpholine, to afford Boc-protected amino acids or the respective acid chlorides (5 Q 1=OH or Cl) to give the corresponding amide (6). Intermediate (6) can be cyclized under acidic conditions at elevated temperatures (e.g., boiling in acetic acid) to give the cyclic imidazole intermediate (7). When an enantiopure amino acid is used as the starting material, partial racemization can occur during the cyclization. The Boc protecting group can be removed under acidic conditions (e.g., HCl in dioxane or trifluoroacetic acid) to give the cyclic imidazolylalkylamine or the respective salt (8). Finally, intermediate (8) can be further reacted with a substituted benzoic acid or the corresponding acid chloride to give the final product IA.

[0290] Q 2 =OH : The imidazole compound represented by formula (8) is reacted with the compound represented by formula (9) (Q 2 ═OH) to form a compound of formula IA. For example, an imidazole of formula (8) is reacted with a carboxylic acid of formula (9) (Q 2 ═OH) with a suitable coupling reagent (e.g., T3P®, HATU, or DCC / HOBt) and a suitable base (e.g., triethylamine or DIPEA) at a temperature ranging from about 0° C. to 100° C. to provide a compound of formula IA. This compound can then be isolated and, if necessary, purified using techniques well known in the art, such as chromatography.

[0291] Q 2 =Cl : The imidazole compound represented by formula (8) is reacted with the compound represented by formula (9) (Q 2 =Cl) to form a compound of formula IA. For example, an imidazole of formula (8) may be reacted with an imidazole of formula (9) (Q 2=Cl) and a suitable base (e.g., triethylamine or DIPEA) at a temperature ranging from about 0 to 100°C to provide a compound of formula IA. This compound can then be isolated and, if necessary, purified using techniques well known in the art, such as chromatography.

[0292] Thioamides of formula (I) (wherein X=S) can be obtained by treating compounds of formula (IA) with Lawesson's reagent in boiling toluene, as described, for example, in WO2005009435.

[0293] Equation (9)(Q 2 =OH) and a carboxylic acid represented by formula (9) (Q 2 =Cl) are commercially available or can be synthesized by methods known to those skilled in the art.

[0294] More specifically, the synthesis of the amine intermediate INT-1 is described in Scheme 1a.

[0295] As shown in Scheme 1a, starting material (1A) is reacted with 6-aminopyridine-3-carbonitrile in DMA at 80 °C in the presence of CSCO as a base. The nitro group is reduced in the next step using SnCl dihydrate. Amide formation from amine (4a) and (S)-Boc-Ala is carried out using HATU as the coupling reagent and DIPEA as the base. The resulting amide (6a) is cyclized under acidic conditions to give the Boc-protected amine intermediate (7a), which is then deprotected at room temperature using 4N HCl in dioxane to give the amine hydrochloride salt (INT-1), which is further derivatized. In the case of partial racemization, art-known chiral separation methods are applied to isolate the pure (S)-enantiomer of 6a, 7a, or INT-1.

[0296] Scheme 1a [ka]

[0297] a. Cs2CO3, DMA; 80 °C, 16 h; b. SnCl2*2H2O, EtOAc, 70 °C, 1 h; c. (S)-Boc-Ala, HATU, DIPEA, DMF, room temperature, 16 h; d. AcOH / dioxane, 100 °C, 4 days; e. 4N HCl in dioxane, room temperature.

[0298] Compounds of formula (I) can be prepared as illustrated in Scheme 2 below, where X is O and R 1 is H, and A 1 , A 2 , A 3 , A 4 , R 2 , R 3 , R 4 , R 5 is as defined above, PG is an amino protecting group, Hal is fluorine, chlorine, bromine or iodine, and Q 1 , Q 2 is hydroxy or chlorine.

[0299] Scheme 2 [ka]

[0300] As shown in Scheme 2, the introduction of the heterocyclic amine group can be carried out by aromatic nucleophilic substitution of the halogen of heterocyclic halide (11) with amino-nitro-azine (10) in the presence of a base such as CsCO or pyridine in various solvents such as acetonitrile, DMF, dioxane, or THF. Alternatively, the heterocyclic amine can be introduced by Buchwald reaction conditions using various palladium catalysts and appropriate ligands, such as those described in US 2010 / 29638 A1 or WO 2012 / 41476 A1. Subsequent conversion to compounds of formula (IA) can be carried out as previously described in Scheme 1.

[0301] In some cases, further derivatization may be possible. For example, R 4 The methyl ester or ethyl ester functional group in 41 R 42 where R 41 and R 42 is as defined above. [Example]

[0302] Intermediates 6-[2-[(1S)-1-Aminoethyl]imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile hydrochloride (INT-1) Step 1: Synthesis of 6-[(3-nitropyridin-2-yl)amino]nicotinonitrile [ka]

[0303] A solution of 2-chloro-3-nitropyridine (8.60 g, 54.24 mmol) in 80 mL of DMA was added dropwise to a stirred solution of 6-aminopyridine-3-carbonitrile (7.11 g, 59.67 mmol) and CsCO (35.35 g, 108.49 mmol) in 150 mL of DMA, and the reaction mixture was stirred at 80 °C overnight. The mixture was cooled to room temperature. The reaction was quenched with ice water at room temperature. The resulting mixture was extracted several times with EtOAc. The combined organic layers were washed with H2O and dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting with cyclohexane / EtOAc (2:1)) to give the desired product (5.60 g, 35.7%). 1H-NMR(400.2 MHz, d6-DMSO, ピークリスト): δ=10.6624 (9.4); 8.7054 (7.9); 8.7011 (16.0); 8.6938 (15.8); 8.6896 (8.9); 8.6107 (7.8); 8.6065 (7.6); 8.5900 (8.3); 8.5858 (7.6); 8.5785 (0.5); 8.5558 (0.3); 8.2566 (6.1); 8.2509 (5.9); 8.2430 (0.4); 8.2346 (9.9); 8.2289 (9.8); 8.1653 (12.2); 8.1447 (6.8); 8.1432 (7.5); 7.3306 (8.8); 7.3190 (8.5); 7.3099 (8.4); 7.2983 (8.4); 5.7578 (0.7); 4.0562 (1.1); 4.0384 (3.2); 4.0206 (3.3); 4.0028 (1.1); 3.3300 (57.6); 2.6775 (0.4); 2.6729 (0.6); 2.6684 (0.4); 2.5265 (1.4); 2.5218 (2.0); 2.5130 (28.0); 2.5085 (59.2); 2.5040 (79.6); 2.4995 (56.6); 2.4950 (26.3); 2.3354 (0.4); 2.3308 (0.5); 2.3263 (0.4); 1.9900 (14.4); 1.3971 (3.5); 1.1935 (3.8); 1.1757 (7.7); 1.1579 (3.7); -0.0002 (4.5) ESI mass [m / z]: 241.9 [M +H] +

[0304] Step 2: 6-[(3-aminopyridin-2-yl)amino]nicotinonitrile

change

[0305] To a stirring solution of 6-[(3-nitropyridin-2-yl)amino]nicotinonitrile (1.25 g, 5.19 mmol) in 20 mL of ethyl acetate was added tin chloride dihydrate (5.86 g, 25.90 mmol), and the reaction mixture was stirred at 70 °C for 1 h. When the mixture was cooled to room temperature, the reaction was quenched with water and basified to pH 9-10 with aqueous sodium carbonate. The mixture was extracted several times with ethyl acetate. The combined organic layers were dried over anhydrous NaSO. After filtration, the filtrate was concentrated under reduced pressure. The crude material was used in the next step without further purification (1.0 g, 72.7% purity, 66% yield). 1H-NMR (400.2 MHz, d6-DMSO, peak list): δ=9.2833 (0.4); 9.2385 (11.2); 9.0450 (0.6); 8.6368 (0.3); 8.6270 (1.1); 8.6221 (1.2); 8.6090 (0.7); 8.6016 (8.4); 8.5999 (9.5); 8.5960 (9.7); 8.5941 (9.4); 8.5820 (0.3); 8.5689 (0.4); 8.3828 (0.7); 8.1775 (0.5); 8.1430 (0.7); 8.1367 (0.8); 8.1333 (0.6); 8.1252 (0.4); 8.0504 (0.4); 8.0447 (0.5); 8.0280 (0.7); 8.0223 (0.8); 8.0149 (0.3); 7.9948 (7.2); 7.9889 (7.2); 7.9724 (9.3); 7.9665 (9.5); 7.9304 (0.7); 7.9081 (0.6); 7.8491 (12.1); 7.8268 (8.7); 7.6360 (7.7); 7.6323 (8.5); 7.6244 (7.9); 7.6206 (8.4); 7.4959 (0.3); 7.4761 (0.4); 7.2761 (0.6); 7.2722 (0.6); 7.2637 (0.6); 7.2598 (0.6); 7.2342 (0.4); 7.2128 (0.4); 7.0990 (0.4); 7.0762 (7.6); 7.0723 (8.4); 7.0567 (9.6); 7.0528 (9.9); 6.9059 (8.3); 6.8942 (7.9); 6.8864 (6.8); 6.8747 (6.4); 6.6969 (0.5); 6.6930 (0.5); 6.6783 (0.6); 6.6744 (0.6); 6.3806 (0.6); 6.3682 (0.6); 6.3621 (0.6); 6.3496 (0.5); 5.3611 (1.1); 5.3242 (16.0); 5.2441 (0.6); 4.6521 (0.4); 4.0575 (0.6); 4.0397 (1.7); 4.0219 (1.7); 4.0042 (0.6); 3.3470 (14.4); 2.5301 (0.4); 2.5255 (0.6); 2.5165 (7.0); 2.5122 (15.4); 2.5077 (21.3); 2.5033 (15.9); 1.9920 (7.4); 1.3021 (0.4); 1.2595 (0.6); 1.2280 (1.2); 1.1942 (2.5); 1.1764 (4.4); 1.1586 (2.2); -0.0002 (5.4). ESI mass [m / z]: 212.2 [M +H] +

[0306] Step 3: tert-butyl [(2S)-1-({2-[(5-cyanopyridin-2-yl)amino]pyridin-3-yl}amino)-1-oxopropan-2-yl]carbamate [ka]

[0307] A mixture of (2S)-2-[(tert-butoxycarbonyl)amino]propanoic acid (806.20 mg, 4.26 mmol), N,N-diisopropylethylamine (2.17 mL, 12.78 mmol), and HATU (1.94 g, 5.11 mmol) in 3 mL of DMF was stirred at room temperature for 10 minutes, then 6-[(3-aminopyridin-2-yl)amino]nicotinonitrile (900.0 mg, 4.26 mmol) was added and the reaction was stirred at room temperature overnight. The mixture was directly purified by preparative HPLC to give the desired product (1.15 g, 65%). 1H-NMR (400.2 MHz, d6-DMSO, ピークリスト): δ=9.8273 (1.1); 9.4949 (0.8); 8.6284 (2.1); 8.6263 (2.1); 8.1999 (1.2); 8.1886 (1.3); 8.0893 (0.9); 8.0676 (1.1); 7.9605 (1.1); 7.9408 (1.2); 7.8617 (0.8); 7.8398 (0.7); 7.2510 (0.7); 7.2371 (0.7); (0.7); 7.1797 (0.8); 7.1746 (0.8); 7.1610 (0.6); 5.7590 (2.2); 4.1516 (0.5); 4.1352 (0.7); 4.1183 (0.5); 3.6981 (0.6); 2.5057 (34.9); 2.5027 (35.1); 1.3945 (0.9); 1.3699 (16.0); 1.3281 (0.7); 1.2840 (3.8); 1.2664 (3.7); 0.0024 (5.8); -0.0002 (6.5) ESI mass [m / z]: 383.5 [M +H] +

[0308] Step 4: tert-butyl {(1S)-1-[3-(5-cyanopyridin-2-yl)-3H-imidazo[4,5-b]pyridin-2-yl]ethyl}carbamate

change

[0309] To a stirring mixture of tert-butyl [(2S)-1-({2-[(5-cyanopyridin-2-yl)amino]pyridin-3-yl}amino)-1-oxopropan-2-yl]carbamate (10.00 g, 26.11 mmol) in dioxane (150.00 mL) was added AcOH (40.00 mL), and the mixture was stirred at 100° C. for 4 days. The mixture was basified to pH 8 with saturated NaHCO (aqueous). The resulting mixture was extracted several times with EtOAc, and the combined organic layers were washed with brine and dried over anhydrous NaSO. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with petroleum ether / EtOAc (3:1)) and then by prep-HPLC to give a mixture of both enantiomers. This partial racemate was purified by prep-SFC to give tert-butyl {(1S)-1-[3-(5-cyanopyridin-2-yl)-3H-imidazo[4,5-b]pyridin-2-yl]ethyl}carbamate (1.59 g, 4.37 mmol, 16.71%). ESI mass [m / z]: 365.2 [M +H] +

[0310] Step 5: 6-[2-[(1S)-1-aminoethyl]imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile hydrochloride (INT-1) [ka]

[0311] tert-Butyl N-[(1S)-1-[3-(5-cyano-2-pyridyl)imidazo[4,5-b]pyridin-2-yl]ethyl]carbamate (200 mg, 0.54 mmol) was dissolved in 4 mL of dioxane, and 4 M HCl in dioxane (1.37 mL) was added. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the remaining residue was used directly in the next step. ESI mass [m / z]: 265.2 [amine +H] +

[0312] Methyl 6-[2-(1-aminoethyl)-3H-imidazo[4,5-b]pyridin-3-yl]nicotinate hydrochloride (INT-5) Step 1: Methyl 6-[(3-nitropyridin-2-yl)amino]nicotinate [ka]

[0313] To a solution of 5.1 g (33.3 mmol) of methyl 6-aminonicotinate and 20.5 g (62.8 mmol) of cesium carbonate in 80 mL of acetonitrile, 4.1 g (26.1 mmol) of 2-chloro-3-nitropyridine was added dropwise, and the mixture was stirred at 80 °C overnight. After cooling to room temperature, the mixture was treated with ice water and extracted several times with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting with cyclohexane / ethyl acetate) to give 780 mg (10.2%) of the title compound. 1 H-NMR (400.2 MHz, CD3CN, peak list): δ=10.5963 (0.8); 8.8964 (2.0); 8.8913 (2.1); 8.6382 (1.7); 8.6297 (3.8); 8.6074 (3.2); 8.3169 (1.4); 8.3113 (1.4); 8.2948 (1.2); 8.2892 (1.2); 7.1545 (1.4); 7.1430 (1.4); 7.1338 (1.4); 7.1222 (1.4); 3.8870 (16.0); 2.1768 (32.9); 2.1643 (0.5); 1.9547 (2.2); 1.9487 (4.3); 1.9426 (6.2); 1.9365 (4.3); 1.9304 (2.2); -0.0002 (2.8) ESI mass [m / z]: 275.3 [M+H] +

[0314] Step 2: Methyl 6-[(3-aminopyridin-2-yl)amino]nicotinate [ka]

[0315] 728.0 mg (2.66 mmol) of methyl 6-[(3-nitropyridin-2-yl)amino]nicotinate was dissolved in 13 mL of ethyl acetate, and then 3.0 g (13.3 mmol) of tin chloride dihydrate was added, and the reaction mixture was stirred at 70 °C for 1.5 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and basified to pH 9-10 with saturated Na2CO3 (aqueous). The aqueous phase was extracted several times with ethyl acetate, and the combined organic layers were washed with brine and dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure, and the crude material was used in the next step without further purification (645 mg, 94% yield). 1 H-NMR (400.2 MHz, d6-DMSO, peak list): δ=9.0965 (3.0); 8.7376 (2.6); 8.7332 (2.4); 8.7318 (2.7); 8.1034 (1.4); 8.0976 (1.4); 8.0810 (1.8); 8.0752 (1.8); 7.9141 (3.0); 7.8918 (2.4); 7.6317 (1.9); 7.6294 (1.8); 7.6200 (1.9); 7.6176 (1.8); 7.0557 (1.7); 7.0534 (1.7); 7.0363 (2.1); 7.0339 (2.0); 6.8727 (1.7); 6.8609 (1.7); 6.8533 (1.4); 6.8416 (1.4); 5.3151 (4.0); 4.0378 (0.4); 4.0201 (0.4); 3.8258 (16.0); 3.3346 (10.2); 2.5039 (14.4); 2.5003 (11.0); 1.9899 (1.7); 1.1933 (0.4); 1.1920 (0.5); 1.1754 (0.9); 1.1742 (0.9); 1.1577 (0.4); 1.1564 (0.4); -0.0002 (5.8); -0.0015 (5.7) ESI mass [m / z]: 245.1[M+H] +

[0316] Step 3: Methyl 6-[(3-{[N-(tert-butoxycarbonyl)alanyl]amino}pyridin-2-yl)amino]nicotinate [ka]

[0317] To a solution of 0.33 g (1.74 mmol) of N-(tert-butoxycarbonyl)alanine in 17 mL of dichloromethane, 0.92 mL (5.23 mmol) of N,N-diisopropylethylamine (DIPEA, Hunig's base) and 0.80 g (2.1 mmol) of [O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate] (HATU) were added, and the mixture was stirred at room temperature for 10 minutes. Then, 0.64 g (2.62 mmol) of methyl 6-[(3-aminopyridin-2-yl)amino]nicotinate was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with 5% sodium dihydrogen phosphate (aqueous), and extracted several times with dichloromethane. The combined organic layers were washed with saturated NaHCO (aq) and brine, dried over anhydrous NaSO, and filtered. The filtrate was concentrated under reduced pressure. The reaction mixture was then directly purified by preparative HPLC (eluting with water / acetonitrile) to afford 497 mg (62.0%) of the title compound. 1H-NMR (400.2 MHz, d6-DMSO, peak list): δ = 8.7905 (1.4); 8.7856 (1.4); 8.1732 (1.0); 8.1686 (1.1); 8.1515 (0.9); 8.1465 (0.9); 8.0346 (0.6); 7.8287 (0.5); 7.0894 (0.4); 7.0726 (0.5); 7.0608 (0.4); 5.8359 (0.3); 4.1648 (0.5); 4.1481 (0.7); 4.1308 (0.5); 4.0679 (0.9); 4.0501 (0.9); 3.8569 (15.4); 2.1828 (2.7); 1.9728 (4.0); 1.9657 (0.4); 1.9538 (4.1); 1.9476 (7.9); 1.9415 (11.4); 1.9353 (7.8); 1.9292 (4.0); 1.4053 (16.0); 1.3747 (5.8); 1.3567 (5.6); 1.2215 (1.0); 1.2038 (2.0); 1.1859 (1.0); -0.0002 (2.4) ESI mass [m / z]: 416.3 [M+H] +

[0318] Step 5: Methyl 6-(2-{1-[(tert-butoxycarbonyl)amino]ethyl}-3H-imidazo[4,5-b]pyridin-3-yl)nicotinate [ka]

[0319] To a solution of 490.0 mg (1.18 mmol) of methyl 6-[(3-{[N-(tert-butoxycarbonyl)alanyl]amino}pyridin-2-yl)amino]nicotinate in 8 mL of dioxane was added 0.7 mL (11.8 mmol) of acetic acid, and the reaction mixture was stirred at 100° C. overnight. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with water, and basified to pH 8 with saturated NaHCO (aq). The organic layer was washed with brine and dried over anhydrous NaSO. After filtration, the filtrate was concentrated under reduced pressure, and the crude material was used in the next step without further purification (450 mg, 93% yield). 1 H-NMR(400.2 MHz, CD3CN, ピークリスト): δ=9.1696 (1.2); 9.1645 (1.2); 8.5775 (1.0); 8.5718 (1.0); 8.5565 (1.1); 8.5507 (1.1); 8.3537 (0.9); 8.3503 (1.0); 8.3417 (1.0); 8.3383 (1.0); 8.0907 (1.2); 8.0871 (1.2); 8.0803 (0.6); 8.0706 (1.3); 8.0671 (1.2); 8.0597 (0.5); 7.3741 (1.0); 7.3620 (1.0); 7.3541 (0.9); 7.3421 (0.9); 4.0677 (0.4); 4.0499 (0.4); 3.9547 (11.7); 3.8410 (0.8); 3.6005 (16.0); 2.1979 (1.1); 2.1832 (75.4); 1.9725 (1.7); 1.9658 (0.4); 1.9538 (6.8); 1.9476 (13.1); 1.9414 (18.6); 1.9352 (12.5); 1.9291 (6.3); 1.5206 (1.4); 1.5038 (1.3); 1.2917 (5.9); 1.2216 (0.6); 1.2039 (1.0); 1.1860 (0.6); -0.0002 (4.3) ESI mass [m / z]: 398.5 [M+H] +

[0320] Step 6: Methyl 6-[2-(1-aminoethyl)-3H-imidazo[4,5-b]pyridin-3-yl]nicotinate hydrochloride (INT-4)

change

[0321] To a solution of 409 mg (1.02 mmol) of methyl 6-(2-{1-[(tert-butoxycarbonyl)amino]ethyl}-3H-imidazo[4,5-b]pyridin-3-yl)nicotinate in 21 mL of dioxane was added 5.15 mL (20.5 mmol) of 4 N HCl in dioxane. The reaction mixture was stirred at room temperature for 3 days. The solvent was evaporated and the remaining residue was used directly in the next step (420 mg, 100% yield). 1 H-NMR (400.2 MHz, d6-DMSO, peak list): δ = 9.1796 (0.8); 9.1741 (0.8); 8.7544 (0.6); 8.7433 (0.6); 8.7018 (0.6); 8.6959 (0.6); 8.6804 (0.7); 8.6746 (0.7); 8.5325 (0.6); 8.5289 (0.7); 8.5205 (0.7); 8.5169 (0.7); 8.4530 (0.9); 8.4318 (0.8); 8.3304 (0.7); 8.3268 (0.7); 8.3103 (0.8); 8.3067 (0.7); 7.5540 (0.6); 7.5421 (0.6); 7.5339 (0.6); 7.5219 (0.6); 3.9584 (5.6); 3.8563 (0.7); 3.7551 (0.4); 3.7107 (0.3); 3.7004 (0.4); 3.6803 (0.5); 3.6707 (0.5); 3.6663 (0.5); 3.6560 (0.5); 3.6503 (0.5); 3.6113 (0.4); 3.5988 (0.4); 3.5820 (0.4); 3.5682 (16.0); 2.5259 (0.8); 2.5211 (1.0); 2.5122 (14.7); 2.5078 (31.5); 2.5033 (42.5); 2.4988 (30.6); 2.4944 (14.6); 1.9097 (0.4); 1.6162 (2.1); 1.5994 (2.1); 1.2341 (0.6); -0.0002 (10.6); -0.0085 (0.3) ESI mass [m / z]: 298.4 [M+H-HCl]+

[0322] 1-[1-(5-chloro-2-pyridyl)imidazo[4,5-c]pyridin-2-yl]ethanamine hydrochloride (INT-7) Step 1: 5-chloro-N-(3-nitro-4-pyridyl)pyridin-2-amine [ka]

[0323] A solution of 3-nitropyridin-4-amine (2.00 g, 14.4 mmol) in 30 mL of DMA was added dropwise to a stirred solution of 5-chloro-2-fluoropyridine (2.27 g, 17.3 mmol) and CsCO (9.37 g, 28.8 mmol) in 30 mL of DMA at 80 °C, and the reaction mixture was stirred at 80 °C overnight. The mixture was cooled to room temperature. The reaction was quenched with ice water at room temperature. The resulting mixture was extracted several times with EtOAc. The combined organic layers were washed with H2O and dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The crude material was used in the next step without further purification (3.60 g, 88.3% yield). ESI mass [m / z]: 251.2 [M +H] +

[0324] Step 2: N-(5-chloropyridin-2-yl)pyridine-3,4-diamine [ka]

[0325] To a stirring solution of 5-chloro-N-(3-nitro-4-pyridyl)pyridin-2-amine (3.60 g, 14.3 mmol) in 72 mL of ethyl acetate was added tin chloride dihydrate (16.2 g, 71.7 mmol), and the reaction mixture was stirred at 70 °C for 1 h. When the mixture cooled to room temperature, the reaction was quenched with water and basified to pH 9-10 with aqueous sodium carbonate. The mixture was extracted several times with ethyl acetate. The combined organic layers were dried over anhydrous NaSO. After filtration, the filtrate was concentrated under reduced pressure. The crude material was used in the next step without further purification (2.51 g, 69.8% yield). ESI mass [m / z]: 221.2 [M +H] +

[0326] Step 3: tert-butyl [1-({4-[(5-chloropyridin-2-yl)amino]pyridin-3-yl}amino)-1-oxopropan-2-yl]carbamate [ka]

[0327] A mixture of N-(tert-butoxycarbonyl)alanine (2.58 g, 13.7 mmol), N,N-diisopropylethylamine (5.94 mL, 34.1 mmol), and HATU (5.19 g, 13.7 mmol) in 30 mL of DMF was stirred at room temperature for 10 min, and then N 4 -(5-Chloropyridin-2-yl)pyridine-3,4-diamine (2.51 g, 11.4 mmol) was added and the reaction was stirred at room temperature overnight. Saturated NaHCO3 (aq) was added and the precipitate was removed by filtration. The filtrate was extracted with EtOAc (3 x 100 mL), and the combined organic layers were dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude product was directly purified by preparative HPLC (eluting with water / acetonitrile) to give the desired product (472 mg, 10.5% yield). ESI mass [m / z]: 392.4 [M +H] +

[0328] Step 4: tert-butyl {1-[1-(5-chloropyridin-2-yl)-1H-imidazo[4,5-c]pyridin-2-yl]ethyl}carbamate [ka]

[0329] To a stirring mixture of tert-butyl [1-({4-[(5-chloropyridin-2-yl)amino]pyridin-3-yl}amino)-1-oxopropan-2-yl]carbamate (815 mg, 2.08 mmol) in dioxane (20.00 mL) was added AcOH (2.38 mL), and the mixture was stirred at 100° C. for 22 h. Further dioxane (10.00 mL) and AcOH (2.38 mL) were added, and the mixture was stirred at 100° C. for 44 h. The mixture was basified to pH 8 with saturated NaHCO (aq). The resulting mixture was extracted several times with EtOAc, and the combined organic layers were washed with brine and dried over anhydrous NaSO. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC (eluted with water / acetonitrile) to afford 446 mg (46.5% yield) of the title compound. ESI mass [m / z]: 374.4 [M +H] +

[0330] Step 5: 1-[1-(5-chloro-2-pyridyl)imidazo[4,5-c]pyridin-2-yl]ethanamine hydrochloride (INT-7) [ka]

[0331] tert-Butyl {1-[1-(5-chloropyridin-2-yl)-1H-imidazo[4,5-c]pyridin-2-yl]ethyl}carbamate (446 mg, 1.19 mmol) was dissolved in 8 mL of dioxane, and 4 M HCl in dioxane (5.97 mL) was added. The reaction mixture was stirred at room temperature overnight. The precipitate (240 mg) was collected by filtration and used in the next step without further purification. ESI mass [m / z]: 274.3 [amine +H] + 1 H-NMR: See NMR peak list (Table 2).

[0332] 1-[1-(5-chloropyridin-2-yl)-1H-imidazo[4,5-b]pyridin-2-yl]ethanamine trifluoroacetate (INT-8) Step 1: 5-chloro-N-(2-nitropyridin-3-yl)pyridin-2-amine [ka]

[0333] 12.5 g (95.0 mmol) of 5-chloro-2-fluoropyridine and 56.3 g (172.8 mmol) of cesium carbonate were suspended in 100 mL of DMA, and the reaction mixture was stirred at 80 °C. Then, 12.0 g (86.4 mmol) of 2-nitropyridin-3-amine dissolved in 100 mL of DMA was added dropwise, and the mixture was stirred at 80 °C overnight. After cooling to room temperature, the mixture was treated with ice water and extracted several times with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting with cyclohexane / EtOAc) to give 13.83 g (72.2%) of the title compound. 1H-NMR (400.2 MHz, d6-DMSO, ピークリスト): δ=9.6748 (13.6); 8.4673 (9.4); 8.4637 (10.7); 8.4464 (10.4); 8.4428 (11.1); 8.3187 (0.3); 8.1982 (11.6); 8.1945 (12.3); 8.1874 (12.9); 8.1837 (12.3); 8.1273 (13.6); 8.1207 (13.9); 7.8018 (12.2); 7.7951 (11.6); 7.7797 (12.9); 7.7731 (12.8); 7.7646 (11.2); 7.7538 (10.5); 7.7438 (10.5); 7.7330 (10.1); 7.0951 (16.0); 7.0841 (0.4); 7.0730 (15.0); 3.3849 (0.4); 3.3524 (223.7); 3.3306 (1.0); 2.6774 (0.7); 2.6729 (1.0); 2.6684 (0.7); 2.6640 (0.3); 2.5264 (2.2); 2.5217 (3.4); 2.5129 (53.2); 2.5085 (115.2); 2.5039 (156.8); 2.4994 (111.7); 2.4949 (51.7); 2.3397 (0.3); 2.3354 (0.7); 2.3308 (1.0); 2.3263 (0.7); 2.3218 (0.3); 2.0769 (0.4); -0.0002 (0.6) ESI mass [m / z]: 251.1 [M+H] +

[0334] Stage 2: N 3 -(5-chloropyridin-2-yl)pyridine-2,3-diamine

change

[0335] 10.7 g (42.8 mmol) of 5-chloro-N-(2-nitropyridin-3-yl)pyridin-2-amine was dissolved in 200 mL of ethyl acetate, and then 48.3 g (214.1 mmol) of tin chloride dihydrate was added, and the reaction mixture was stirred at 70 °C for 1 hour. After cooling to room temperature, the mixture was treated with water and basified to pH 9-10 with saturated Na2CO3 (aqueous). The resulting mixture was extracted several times with EtOAc and dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure, and the crude material was used in the next step without further purification (6.13 g, 65% yield). 1 H-NMR (400.2 MHz, d6-DMSO, peak list): δ=8.1607 (7.2); 8.0648 (7.2); 8.0583 (7.3); 7.7234 (16.0); 7.7149 (3.7); 7.7107 (7.2); 7.7046 (6.3); 7.7009 (3.1); 7.6080 (5.4); 7.6013 (5.2); 7.5857 (5.7); 7.5790 (5.5); 6.7264 (7.9); 6.7041 (7.6); 6.5794 (5.1); 6.5664 (4.5); 6.5610 (4.7); 6.5480 (4.9); 5.7173 (8.1); 3.3361 (16.7); 2.6718 (0.4); 2.5254 (1.0); 2.5117 (21.7); 2.5074 (45.4); 2.5029 (60.6); 2.4984 (43.0); 2.4940 (19.9); 2.3296 (0.4); 1.9896 (0.8); 1.1748 (0.4); 0.0079 (1.6); -0.0002 (49.2); -0.0085 (1.6) ESI mass [m / z]: 221.1 [M+H] +

[0336] Step 3: tert-butyl [1-({3-[(5-chloropyridin-2-yl)amino]pyridin-2-yl}amino)-1-oxopropan-2-yl]carbamate [ka]

[0337] 2.68 g (14.2 mmol) of N-(tert-butoxycarbonyl)alanine, 7.2 mL (42.5 mmol) of N,N-diisopropylethylamine (DIPEA, Hunig's base), and 6.45 g (17.0 mmol) of [O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate] (HATU) were dissolved in 30 mL of dichloromethane and stirred at room temperature for 10 min. Then, 3.12 g (14.18 mmol) of N 3 N-(5-chloropyridin-2-yl)pyridine-2,3-diamine was added, and the reaction mixture was stirred at room temperature overnight. An additional 3 mL of dimethylformamide was added, and the mixture was stirred at room temperature for another 4 h. Finally, a solution of 1.34 g (7.08 mmol) of N-(tert-butoxycarbonyl)alanine, 3.22 g (8.5 mmol) of HATU, and 3.1 mL of DIPEA in dichloromethane, which had been stirred for 10 min, was added, and the mixture was stirred at room temperature overnight. The reaction mixture was treated with water and extracted several times with dichloromethane. The combined organic layers were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure. The residue was first purified by silica gel column chromatography (eluted with cyclohexane / EtOAc) and then by prep-HPLC to give 978.0 mg (17.0%) of the title compound. 1H-NMR (400.2 MHz, d6-DMSO, peak list): δ=10.2788 (1.0); 8.4417 (0.8); 8.4227 (0.8); 8.1456 (1.3); 8.1397 (1.4); 8.0827 (0.9); 8.0743 (0.9); 8.0333 (1.2); 7.6869 (0.9); 7.6804 (0.9); 7.6647 (1.0); 7.6582 (1.0); 7.3070 (1.3); 7.2954 (1.3); 7.2866 (1.4); 7.2750 (1.9); 7.2621 (0.7); 6.9163 (1.0); 6.8941 (1.0); 4.1486 (0.4); 4.1317 (0.6); 4.1154 (0.4); 3.3175 (15.4); 2.5239 (0.4); 2.5192 (0.7); 2.5106 (9.7); 2.5061 (20.5); 2.5015 (27.5); 2.4969 (19.2); 2.4924 (8.8); 1.3919 (16.0); 1.2698 (3.5); 1.2521 (3.4); -0.0002 (4.4) ESI mass [m / z]: 392.1 [M+H] +

[0338] Step 4: tert-butyl {1-[1-(5-chloropyridin-2-yl)-1H-imidazo[4,5-b]pyridin-2-yl]ethyl}carbamate [ka]

[0339] To a solution of 739 g (1.88 mmol) of tert-butyl [1-({3-[(5-chloropyridin-2-yl)amino]pyridin-2-yl}amino)-1-oxopropan-2-yl]carbamate in dioxane was added 1 mL of acetic acid, and the reaction mixture was stirred at 100° C. for 2 days. The mixture was evaporated under reduced pressure, and the crude material was used in the next step without further purification (702 mg, 76% yield, 76.5% purity). 1H-NMR (400.2 MHz, d6-DMSO, peak list): δ=12.0060 (0.4); 8.7398 (1.3); 8.7341 (1.3); 8.4797 (1.4); 8.4761 (1.6); 8.4679 (1.5); 8.4643 (1.6); 8.2799 (0.8); 8.2737 (0.8); 8.2582 (0.9); 8.2525 (0.8); 8.2456 (0.6); 7.8147 (1.0); 7.8049 (1.6); 7.7967 (1.1); 7.7838 (1.4); 7.3692 (0.7); 7.3488 (0.8); 7.3113 (1.2); 7.2994 (1.2); 7.2911 (1.2); 7.2792 (1.1); 5.2270 (0.5); 5.2204 (0.4); 5.2018 (0.6); 5.1837 (0.4); 4.9090 (1.1); 4.8399 (0.4); 4.3289 (0.8); 4.3252 (0.4); 4.0010 (0.7); 3.8322 (0.4); 3.8024 (0.5); 3.6092 (0.7); 3.6014 (1.1); 3.5951 (0.6); 3.5900 (0.5); 3.5834 (0.4); 3.5727 (0.5); 3.5669 (0.7); 3.5568 (0.5); 3.5508 (0.6); 3.5460 (0.5); 3.5296 (0.7); 3.5213 (0.8); 3.4993 (0.6); 3.4939 (0.9); 3.4317 (0.3); 3.4276 (0.4); 3.4045 (0.4); 3.3090 (3.6); 3.1705 (0.5); 3.1541 (0.5); 3.1427 (0.4); 3.1261 (0.4); 2.9943 (1.0); 2.8135 (0.5); 2.6908 (2.8); 2.5195 (0.4); 2.5108 (7.7); 2.5064 (16.8); 2.5019 (23.4); 2.4974 (17.2); 2.4931 (8.5); 2.0819 (0.3); 2.0512 (0.6); 1.5027 (2.9); 1.4857 (2.8); 1.3748 (0.6); 1.3654 (2.2); 1.3279 (0.8); 1.2527 (16.0); 1.1257 (0.7); 1.1088 (0.6); 1.0466 (0.8); 1.0314 (0.8); -0.0002 (1.8). ESI mass [m / z]: 374.1 [M+H] +

[0340] Step 5: 1-[1-(5-chloropyridin-2-yl)-1H-imidazo[4,5-b]pyridin-2-yl]ethanamine trifluoroacetate (INT-8) [ka]

[0341] To a solution of 700 mg of tert-butyl {1-[1-(5-chloropyridin-2-yl)-1H-imidazo[4,5-b]pyridin-2-yl]ethyl}carbamate in 25 mL of dioxane was added 2.88 mL (37.4 mmol) of TFA. The reaction mixture was stirred for 3 hours at room temperature overnight. The solvent was evaporated, and the remaining residue was used directly in the next step (735 mg, 100% yield). 1H-NMR (600.1 MHz, d6-DMSO, peak list): δ=8.8227 (1.9); 8.8220 (1.9); 8.8184 (2.0); 8.8176 (1.9); 8.7373 (1.4); 8.7313 (1.4); 8.6617 (0.1); 8.6299 (0.1); 8.6251 (0.1); 8.5961 (1.6); 8.5937 (1.7); 8.5883 (1.8); 8.5858 (1.7); 8.4440 (0.1); 8.3713 (1.7); 8.3669 (1.6); 8.3570 (1.8); 8.3526 (1.7); 8.3167 (0.2); 8.2605 (0.2); 8.2498 (0.2); 8.2288 (0.1); 8.2119 (0.1); 8.1415 (0.2); 8.1378 (0.4); 8.1266 (0.2); 8.1222 (0.1); 8.0741 (1.6); 8.0716 (1.7); 8.0604 (1.8); 8.0579 (1.8); 7.9260 (2.2); 7.9252 (2.1); 7.9117 (2.1); 7.9109 (2.0); 7.7110 (0.1); 7.7065 (0.1); 7.6963 (0.1); 7.6917 (0.1); 7.4599 (1.6); 7.4520 (1.6); 7.4462 (1.6); 7.4383 (1.6); 4.9961 (0.2); 4.9873 (0.4); 4.9778 (0.5); 4.9671 (0.4); 4.9570 (0.2); 4.7158 (1.1); 4.5296 (0.1); 4.5224 (0.1); 4.5145 (0.1); 4.3305 (0.1); 4.0693 (0.2); 3.7756 (0.2); 3.7713 (0.1); 3.7681 (0.2); 3.7650 (0.1); 3.7606 (0.1); 3.7139 (0.7); 3.6822 (0.1); 3.6743 (0.1); 3.6664 (0.1); 3.5698 (16.0); 3.3937 (0.1); 3.0159 (1.1); 2.8890 (1.0); 2.6922 (4.5); 2.6205 (0.2); 2.6174 (0.3); 2.6144 (0.2); 2.5564 (0.1); 2.5471 (0.2); 2.5378 (0.2); 2.5264 (0.7); 2.5233 (0.8); 2.5202 (0.8); 2.5115 (14.5); 2.5085 (32.2); 2.5054 (45.2); 2.5023 (32.4); 2.4993 (14.8); 2.3924 (0.2); 2.3893 (0.3); 2.3862 (0.2); 1.9102 (0.3); 1.5564 (5.1); 1.5450 (5.1); 1.5359 (0.5); 1.4161 (0.3); 1.4045 (0.3); 1.3942 (0.2); 1.3822 (0.2); 1.3577 (0.3); 1.3088 (0.5); 1.2973 (0.5); 1.2365 (0.4); 1.1125 (0.2); 1.0446 (0.2); 1.0345 (0.2); 0.0968 (0.3); 0.0054 (2.1); -0.0001 (72.5); -0.0057 (2.3); -0.1003 (0.3). ESI mass [m / z]: 274.3 [M +H-TFA] +

[0342] Example N-[(1S)-1-[3-(5-cyano-2-pyridyl)imidazo[4,5-b]pyridin-2-yl]ethyl]-3-methylsulfonyl-5-(trifluoromethoxy)benzamide (Example I-1)

change

[0343] To a solution of 35.5 mg (0.13 mmol) of 3-(1-cyano-1-methyl-ethyl)-5-(trifluoromethoxy)benzoic acid in 1 mL of N,N-dimethylformamide (DMF), 0.06 mL (0.33 mmol) of N,N-diisopropylethylamine (DIPEA; Hunig's base) and 86.3 mg (0.22 mmol) of [O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate] (HATU) were added. The mixture was stirred at room temperature for 10 minutes. Next, 39.1 mg (0.13 mmol) of 6-[2-[(1S)-1-aminoethyl]imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile hydrochloride was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then directly purified by preparative HPLC (eluting with water / acetonitrile) to give 29.1 mg (41.4% yield) of the title compound. ESI mass [m / z]: 520.2 [M+H] + 1 H-NMR: See the NMR peak list (Table 1).

[0344] Methyl 6-(2-{1-[3,5-bis(trifluoromethyl)benzamido]ethyl}-3H-imidazo[4,5-b]pyridin-3-yl)nicotinate (Example I-22) [ka]

[0345] To a solution of 485.0 mg (1.45 mmol) of methyl 6-[2-(1-aminoethyl)-3H-imidazo[4,5-b]pyridin-3-yl]nicotinate hydrochloride in 10 mL of dichloromethane, 0.61 mL (4.36 mmol) of triethylamine was added, and the mixture was stirred at room temperature for 30 minutes. Subsequently, 442.0 mg (1.60 mmol) of 3,5-bis(trifluoromethyl)benzoyl chloride, previously dissolved in 2 mL of dichloromethane, was added. The reaction mixture was stirred overnight at room temperature. The mixture was washed with 5% sodium dihydrogen phosphate (aqueous) and extracted several times with dichloromethane. The combined organic layers were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure. The crude material was suspended in 6 mL of acetonitrile, and the corresponding precipitate was filtered and dried, while the filtrate was then purified by preparative HPLC (eluted with water / acetonitrile) to give 288 mg (36.0%) of the title compound. ESI mass [m / z]: 538.2 [M+H]+ 1 H-NMR: See the NMR peak list (Table 1).

[0346] 6-(2-{1-[3,5-bis(trifluoromethyl)benzamido]ethyl}-3H-imidazo[4,5-b]pyridin-3-yl)-N,N-dimethylnicotinamide (Example I-26) Step 1: 6-(2-{1-[3,5-bis(trifluoromethyl)benzamido]ethyl}-3H-imidazo[4,5-b]pyridin-3-yl)nicotinic acid [ka]

[0347] To a solution of 270 mg (0.50 mmol) of methyl 6-(2-{1-[3,5-bis(trifluoromethyl)benzamido]ethyl}-3H-imidazo[4,5-b]pyridin-3-yl)nicotinate (from Example I-22) in a mixture of THF / water (6 mL / 0.6 mL) was added 42 mg (1.0 mmol) of lithium hydroxide, and the mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and acidified with HCl 10%. The aqueous phase was separated and extracted several times with ethyl acetate. The combined organic layers were dried over anhydrous NaSO, filtered, and the filtrate was concentrated under reduced pressure. The crude material was used in the next step without further purification to yield 260 mg (82.0%) of the title compound. 1H-NMR (400.2 MHz, CD3CN, peak list): δ=9.1430 (4.6); 9.1376 (4.8); 8.8535 (0.4); 8.6401 (0.9); 8.5111 (3.1); 8.5054 (3.0); 8.4903 (4.0); 8.4844 (3.4); 8.4396 (0.5); 8.4351 (0.5); 8.4076 (3.3); 8.4045 (3.4); 8.3955 (3.4); 8.3927 (3.5); 8.2350 (1.1); 8.1991 (10.3); 8.1806 (0.7); 8.1666 (0.4); 8.1485 (0.4); 8.1406 (3.3); 8.1374 (3.3); 8.1205 (8.0); 8.0573 (5.6); 8.0364 (5.8); 8.0222 (1.3); 7.9346 (0.7); 7.5910 (0.4); 7.4266 (3.1); 7.4145 (3.1); 7.4065 (3.0); 7.3944 (2.9); 6.9744 (0.8); 6.0060 (0.6); 5.9886 (2.3); 5.9706 (3.4); 5.9526 (2.3); 5.9355 (0.5); 4.0862 (0.5); 4.0679 (1.5); 4.0502 (1.5); 4.0319 (0.5); 3.9236 (0.4); 3.1779 (0.3); 2.9701 (0.3); 2.9638 (0.3); 2.9029 (0.4); 2.8856 (0.4); 2.8600 (0.4); 2.8542 (0.4); 2.8504 (0.4); 2.8003 (0.5); 2.7166 (0.7); 2.6825 (0.8); 2.6260 (1.0); 2.5965 (1.2); 2.5664 (1.4); 2.5415 (1.6); 2.4809 (3.2); 2.4762 (4.2); 2.4717 (5.0); 2.4670 (4.4); 2.4629 (3.7); 2.2422 (43.0); 2.1221 (8.4); 2.1150 (8.3); 2.1089 (8.3); 2.1027 (7.3); 2.0964 (6.3); 2.0526 (4.0); 1.9994 (2.3); 1.9933 (2.2); 1.9728 (8.9); 1.9657 (7.3); 1.9538 (124.1); 1.9477 (207.5); 1.9415 (297.5); 1.9354 (205.2); 1.9292 (106.5); 1.8818 (1.4); 1.8742 (1.4); 1.8369 (1.0); 1.8190 (1.0); 1.8022 (1.1); 1.7826 (1.6); 1.7762 (2.2); 1.7648 (16.0); 1.7476 (15.0); 1.6748 (1.7); 1.6569 (1.6); 1.6204 (0.5); 1.6009 (0.6); 1.5826 (0.6); 1.5701 (0.5); 1.5591 (0.8); 1.5408 (0.8); 1.5038 (1.1); 1.4860 (1.1); 1.4495 (0.4); 1.4322 (0.4); 1.3869 (11.4); 1.3552 (0.5); 1.3402 (1.0); 1.3156 (1.0); 1.2851 (1.8); 1.2699 (5.2); 1.2405 (1.0); 1.2218 (2.4); 1.2164 (2.4); 1.2039 (4.3); 1.2001 (3.4); 1.1863 (2.1); 1.1637 (0.4); 1.1463 (0.4); 1.0830 (0.5); 1.0607 (0.6); 0.8980 (0.5); 0.8818 (1.1); 0.8590 (1.1); 0.8415 (0.8); 0.1462 (1.2); 0.0080 (7.3); -0.0002 (234.6); -0.0078 (9.7); -0.0411 (0.4); -0.1497 (1.1). ESI mass [m / z]: 524.3 [M+H] +

[0348] Step 2: 6-(2-{1-[3,5-bis(trifluoromethyl)benzamido]ethyl}-3H-imidazo[4,5-b]pyridin-3-yl)-N,N-dimethylnicotinamide (Example I-26)

change

[0349] To a solution of 60 mg (0.11 mmol) of 6-(2-{1-[3,5-bis(trifluoromethyl)benzamido]ethyl}-3H-imidazo[4,5-b]pyridin-3-yl)nicotinic acid in 2.0 mL of dichloromethane, 0.06 mL (0.32 mmol) of N,N-diisopropylethylamine (DIPEA, Hunig's base) and 52.0 mg (0.14 mmol) of [O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate] (HATU) were added, and the mixture was stirred at room temperature for 30 minutes. Next, 0.086 mL (0.17 mmol) of dimethylamine (2 M solution in THF) predissolved in 1 mL of dichloromethane was added, and the reaction mixture was stirred at room temperature overnight. After evaporation of the solvent under reduced pressure, the crude material was directly purified by preparative HPLC (eluted with water / acetonitrile) to afford 40 mg (64.0%) of the title compound. ESI mass [m / z]: 551.2 [M+H] + 1 H-NMR: See the NMR peak list (Table 1).

[0350] N-[1-[1-(5-chloro-2-pyridyl)imidazo[4,5-b]pyridin-2-yl]ethyl]-3-cyclopropyl-5-(trifluoromethoxy)benzamide (Example I-33) [ka]

[0351] To a solution of 67.0 mg (0.27 mmol) of 3-cyclopropyl-5-(trifluoromethoxy)benzoic acid in 2 mL of N,N-dimethylformamide, 0.12 mL (0.70 mmol) of N,N-diisopropylethylamine (DIPEA, Hunig's base) and 180.0 mg (0.47 mmol) of [O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate] (HATU) were added, and the mixture was stirred at room temperature for 10 minutes. Then, 104.7 mg (0.27 mmol) of 1-[1-(5-chloropyridin-2-yl)-1H-imidazo[4,5-b]pyridin-2-yl]ethanamine trifluoroacetate was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then directly purified by preparative HPLC (eluting with water / acetonitrile). The resulting product was dissolved in DCM and filtered through a basic cartridge. The filtrate was evaporated under reduced pressure to give 53 mg (38.0%) of the title compound. ESI mass [m / z]: 502.2 [M+H] + 1 H-NMR: See the NMR peak list (Table 1).

[0352] N-[1-[1-(5-chloro-2-pyridyl)imidazo[4,5-c]pyridin-2-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide (Example I-39) [ka]

[0353] To a solution of 50.0 mg (0.194 mmol) of 3,5-bis(trifluoromethyl)benzoic acid in 2 mL of N,N-dimethylformamide (DMF), 0.05 mL (0.27 mmol) of N,N-diisopropylethylamine (DIPEA; Hunig's base) and 88.4 mg (0.23 mmol) of [O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate] (HATU) were added. The mixture was stirred at room temperature for 30 minutes. Next, 79.5 mg (0.29 mmol) of rac-1-[1-(5-chloro-2-pyridyl)imidazo[4,5-c]pyridin-2-yl]ethanamine hydrochloride (INT-7) was added, and the reaction mixture was stirred at room temperature overnight. Another solution of 50.0 mg (0.194 mmol) of 3,5-bis(trifluoromethyl)benzoic acid in 1 mL of N,N-dimethylformamide (DMF) was mixed with 0.05 mL (0.27 mmol) of N,N-diisopropylethylamine (DIPEA; Hunig's base) and 88.4 mg (0.23 mmol) of [O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate] (HATU), stirred at room temperature for 30 minutes, and added to the previous reaction mixture. The mixture was stirred at room temperature for 3 days. The reaction mixture was then directly purified by preparative HPLC (eluted with water / acetonitrile) to afford 6.8 mg (6.1% yield) of the title compound. ESI mass [m / z]: 514.3 [M+H] + 1 H-NMR: See the NMR peak list (Table 1).

[0354] Analysis method The analytical methods described below represent all information throughout this document, except where the procedure for each analytical measurement is described separately.

[0355] mass spectrometry [M+H] by LC-MS under acidic chromatographic conditions+ or M - The measurements were carried out using 1 mL of formic acid per liter of acetonitrile and 0.9 mL of formic acid per liter of Millipore water as the eluent. A Zorbax Eclipse Plus C18 50 mm x 2.1 mm column was used. The column oven temperature was 55°C.

[0356] device: LC-MS3 Waters UPLC with SQD2 mass spectrometer and SampleManager autosampler. Linear gradient: 0.0 → 1.70 min 10% acetonitrile → 95% acetonitrile, 1.70 → 2.40 min constant 95% acetonitrile. Flow rate: 0.85 mL / min.

[0357] LC-MS6 and LC-MS7 Agilent 1290LC, Agilent MSD, HTS PAL autosampler. Linear gradient: 0.0 → 1.80 min 10% acetonitrile → 95% acetonitrile, 1.80 → 2.50 min constant 95% acetonitrile. Flow rate: 1.0 mL / min.

[0358] [M+H] by LC-MS under neutral chromatographic conditions + The measurements were carried out using acetonitrile and Millipore water (containing 79 mg / L of ammonium carbonate) as the eluent.

[0359] device: LC-MS4 Waters IClass Acquity with a QDA mass spectrometer and FTN autosampler (Waters Acquity 1.7 μm 50 mm × 2.1 mm column, oven temperature: 45 °C). Linear gradient: 0.0 → 2.10 min 10% acetonitrile → 95% acetonitrile, 2.10 → 3.00 min constant 95% acetonitrile, flow rate: 0.7 mL / min.

[0360] LC-MS8Waters IClass Acquity with a QDA mass spectrometer and FTN autosampler (Waters Acquity 1.7 μm 50 mm × 2.1 mm column, oven temperature: 45 °C). Linear gradient: 0.0 → 2.10 min 10% acetonitrile → 95% acetonitrile, 2.10 → 3.00 min constant 95% acetonitrile, flow rate: 0.7 mL / min.

[0361] Retention time indices were calculated in all cases based on a homologous series of straight-chain alkan-2-ones having 3 to 16 carbons, where the index of the first alkanone was set to 300, the index of the last alkanone was set to 1600, and corresponding indices in between were calculated using linear interpolation between the values ​​of successive alkanones.

[0362] NMR 1 H-NMR data were measured using a Bruker Avance III 400 MHz spectrometer equipped with a 1.7 mm TCI probehead, using tetramethylsilane as the reference standard (0.00 ppm), and measurements were typically recorded from solutions in CDCN, CDCl, or dDMSO. Alternatively, a Bruker Avance III 600 MHz instrument equipped with a 5 mm CPNMP probehead or a Bruker Avance NEO 600 MHz instrument equipped with a 5 mm TCI probehead was used for the measurements. Generally, the measurements were performed at a probehead temperature of 298 K. Alternative measurement temperatures are specified.

[0363] The NMR data for selected examples is presented in conventional form (δ values, multiplet splitting, number of hydrogen atoms) or as an NMR peak list.

[0364] NMR peak list method Selected Examples 1 H-NMR data is 1The data are listed in the form of a H-NMR peak list. For each signal peak, the δ value (ppm) and the signal intensity in parentheses are listed. A semicolon is used as a separator between pairs of δ value and signal intensity.

[0365] Thus, one example peak list takes the form: δ1(Intensity 1);δ2(Intensity 2);...;δ i (strength i );...;δ n (strength n ).

[0366] The intensity of the sharp signal is 1 It correlates with the signal height (cm) in the printed diagram of the H-NMR spectrum, showing the true relationship of signal intensity. Several peaks from a broad signal or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.

[0367] 1 To calibrate the chemical shifts for the H spectrum, tetramethylsilane is used, or if the sample does not contain tetramethylsilane, the chemical shifts of the solvent are used. 1 In the H-NMR peak list, the peak for tetramethylsilane may be present, but it is not necessary.

[0368] 1 The list of H-NMR peaks is given by the classical 1 It is equivalent to a H-NMR print and is usually 1 It contains all peaks that are described in the classical interpretation of H-NMR.

[0369] Furthermore, they are classical 1 Like the H-NMR print, it may also show signals of the solvent, signals of stereoisomers of the compound (which are also optionally part of the subject matter of the present invention) and / or signals of impurity peaks.

[0370] 1 The 1 H-NMR solvent signals, the tetramethylsilane signals and the water signals in the corresponding solvents have very high intensity values ​​and are therefore excluded from the relative intensity calibration.

[0371] On average, the peaks of stereoisomers and / or impurity peaks of the compounds according to the invention usually have lower intensities than the peaks of the compounds of the invention (e.g., compounds of the invention having a purity of more than 90%).

[0372] Such stereoisomers and / or impurities may be specific to a particular preparation method, and therefore the corresponding peaks may help to verify the reproducibility of the preparation method by "side-product fingerprints."

[0373] An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, and also using empirically evaluated expectation values) can assign the peaks of the target compounds, optionally using additional intensity filters, if necessary. This assignment is 1 This would be similar to the usual peak picking in classical interpretation of H-NMR.

[0374] The solvent used can be extracted from the JCAMP file using the parameters "solvent", spectrometer frequency "observation frequency" and spectrometer type "spectrometer / data system".

[0375] 13 C-NMR data is 1 Similar to the H-NMR data, broadband decoupled 13 Shown as a peak list from the C-NMR spectrum. 13 The C-NMR solvent signals and tetramethylsilane are excluded from the relative intensity calibration because these signals can have very high intensities.

[0376] Further details regarding the description of NMR data by peak lists are disclosed in the publication "Citation of NMR Peaklist Data within Patent Applications," Research Disclosure Database Number 564025.

[0377] The compounds of the present invention described in Table 1 below can also be obtained by the above-described preparation examples or by methods similar to the preparation examples, and can be obtained by the above-described preparation examples. 1 is hydrogen and X is oxygen.

[0378] [ka]

[0379] [Table 2] TIFF2024516278000052.tif225166TIFF2024516278000053.tif233166TIFF2024516278000054.tif236167TIFF20245162780 00055.tif226167TIFF2024516278000056.tif204167TIFF2024516278000057.tif199166TIFF2024516278000058.tif206166 TIFF2024516278000059.tif252166TIFF2024516278000060.tif208166TIFF2024516278000061.tif249165TIFF20245162780 00062.tif209166TIFF2024516278000063.tif249168TIFF2024516278000064.tif238165TIFF2024516278000065.tif218167

[0380] [Table 3] TIFF2024516278000067.tif242167

[0381] Biological Examples Rhipicephalus (Boophilus) microplus - In vitro contact test Larval bullfrog tick (Parkhurst strain resistant to synthetic pyrethroids) 9 mg of compound is dissolved in 1 mL of acetone and diluted with acetone to the desired concentration. 250 μL of the test solution is placed in a 25 mL glass test tube and uniformly distributed on the inner wall by rotating and tilting on a shaker (30 rpm for 2 hours). 900 ppm compound concentration, 44.7 cm 2 The inner surface and uniform distribution of 5 μg / cm 2 A dose of 100 mg / kg is achieved.

[0382] After the solvent has evaporated, 20-50 larval bullfrog ticks (Rhipicephalus microplus) are placed in each tube, which are then closed with perforated lids and incubated horizontally in an incubator at 85% relative humidity and 27°C. Efficacy is determined after 48 hours. The larvae are gently tapped to the bottom of the tube, and negative geotaxis is recorded. Larvae that climb to the top of the vial in the same manner as untreated control larvae are recorded as alive; larvae that do not climb in the same manner as untreated control larvae but only exhibit jerky or twitching leg movements are recorded as dying; and tick larvae that remain completely motionless at the bottom are counted as dead.

[0383] A compound is 5 μg / cm 2 A compound shows good efficacy against Rhipicephalus microplus if an efficacy of at least 80% is monitored at a compound concentration of 100%. 100% efficacy means that all Rhipicephalus larvae are dead or dying; 0% means that no Rhipicephalus larvae are dead or dying.

[0384] In this test, for example, the following compound of the Preparation Examples was tested at 5 μg / cm 2(=500g / ha) showed 100% good activity: I-2. In this test, for example, the following compound of the Preparation Examples was tested at 5 μg / cm 2 (=500g / ha) showed good activity of 90%: I-3. In this test, for example, the following compound of the Preparation Examples was tested at 5 μg / cm 2 (=500g / ha) showed good activity of 80%: I-1. In this test, for example, the following compound of the Preparation Examples was tested at 1 μg / cm 2 At an application rate of (=100 g / ha), the following plants showed good activity of 100%: I-2, I-8, I-14, I-15, I-16, I-31. In this test, for example, the following compound of the Preparation Examples was tested at 1 μg / cm 2 At an application rate of (=100 g / ha), the following plants showed good activity of 90%: I-1, I-3, I-6, I-7, I-11, I-13. In this test, for example, the following compound of the Preparation Examples was tested at 1 μg / cm 2 (=100g / ha) showed good activity of 80%: I-9.

[0385] Rhipicephalus (Boophilus) microplus - injection test Solvent: Dimethyl sulfoxide To prepare a suitable preparation of the active compound, 10 mg of the active compound are dissolved in 0.5 ml of solvent and the concentrate obtained is diluted with solvent to the desired concentration.

[0386] Five engorged adult female bull ticks (Rhipicephalus microplus) are injected with 1 μL of compound solution into their abdomens, transferred to replica plates, and incubated in a climate chamber.

[0387] After 7 days, the eggs are monitored for fertilized eggs. Eggs that are not obviously fertilized are kept in a climate chamber until they hatch after approximately 42 days. 100% efficacy means that all eggs are infertile; 0% means that all eggs are fertilized.

[0388] In this test, for example, the following compounds of the Preparation Examples showed 100% good activity at an application rate of 4 μg per tick: I-1, I-2, I-3.

[0389] Cat flea (Ctenocephalides felis) - Oral test Solvent: Dimethyl sulfoxide To prepare a suitable preparation of the active compound, 10 mg of the active compound is dissolved in 0.5 mL of solvent and the resulting concentrate is diluted with citrated bovine blood to the desired concentration.

[0390] Approximately 20 unfed adult cat fleas (Ctenocephalides felis) are placed in a flea chamber covered with gauze on the top and bottom. A blood-compound solution is placed in a chamber whose bottom is sealed with parafilm and placed on top of the flea chamber, allowing the cat fleas to suck the blood. The blood chamber is heated to 37°C, and the flea chamber is maintained at room temperature.

[0391] After two days, the mortality rate (%) is calculated: 100% means that all cat fleas have been killed; 0% means that no cat fleas have been killed.

[0392] In this test, for example, the following compounds of the Preparation Examples showed 100% good activity at an application rate of 100 ppm: I-1.

[0393] Cat flea (Ctenocephalides felis) - In vitro contact test Adult cat flea 9 mg of compound is dissolved in 1 mL of acetone and diluted with acetone to the desired concentration. 250 μL of the test solution is placed in a 25 mL glass test tube and uniformly distributed on the inner wall by rotating and tilting on a shaker (30 rpm for 2 hours). 900 ppm compound concentration, 44.7 cm 2 The inner surface and uniform distribution of 5 μg / cm 2 A dose of 100 mg / kg is achieved.

[0394] After the solvent has evaporated, 5-10 adult cat fleas (Ctenocephalides felis) are placed in each test tube, which is then closed with a perforated lid and incubated in a horizontal position at room temperature and relative humidity. Efficacy is determined after 48 hours. The cat fleas are tapped to the bottom of the test tube and incubated on a heating plate at 45-50°C for a maximum of 5 minutes. Cat fleas that remain immobile or move jerkily and are unable to escape the heat by crawling are scored as dead or dying.

[0395] A compound is 5 μg / cm 2 A compound exhibits good efficacy against cat fleas (Ctenocephalides felis) if at least 80% efficacy is monitored at a compound concentration of 100%. 100% efficacy means that all cat fleas are dead or dying; 0% means that no cat fleas are dead or dying.

[0396] In this test, for example, the following compound of the Preparation Examples was tested at 1 μg / cm 2 (=100g / ha) showed good activity of 80%: I-15.

[0397] Brown dog tick (Rhipicephalus sanguineus) - In vitro contact test using adult Brown dog ticks 9 mg of compound is dissolved in 1 mL of acetone and diluted with acetone to the desired concentration. 250 μL of the test solution is placed in a 25 mL glass test tube and uniformly distributed on the inner wall by rotating and tilting on a shaker (30 rpm for 2 hours). 900 ppm compound concentration, 44.7 cm 2 The inner surface and uniform distribution of 5 μg / cm 2 A dose of 100 mg / kg is achieved.

[0398] After the solvent has evaporated, 5-10 adult Brown Dog Ticks (Rhipicephalus sanguineus) are placed in each test tube, which is then closed with a perforated lid and incubated in a horizontal position at room temperature and relative humidity. Efficacy is determined after 48 hours. The Brown Dog Ticks are then gently tapped to the bottom of the tube and incubated on a heating plate at 45-50°C for a maximum of 5 minutes. Ticks that remain immobile or move jerkily and are unable to escape the heat by crawling are scored as dead or dying.

[0399] A compound is 5 μg / cm 2 A compound exhibits good efficacy against Rhipicephalus sanguineus if at least 80% efficacy is monitored at a compound concentration of 100%. 100% efficacy means that all Rhipicephalus sanguineus ticks are dead or dying; 0% means that no Rhipicephalus sanguineus ticks are dead or dying.

[0400] In this test, for example, the following compound of the Preparation Examples was tested at 1 μg / cm 2 (=100g / ha) showed 100% good activity: I-17. In this test, for example, the following compound of the Preparation Examples was tested at 1 μg / cm 2 At an application rate of (=100 g / ha), the following plants showed good activity of 80%: I-8, I-13, I-15.

[0401] Cotton aphid (Aphis gossypii) - oral test Solvent: 100 parts by weight acetone To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the above-mentioned amount of solvent and the concentrate obtained is diluted with water to the desired concentration.

[0402] 50 μL of compound solution was placed into a microtiter plate and 150 μL of IPL41 insect medium (33% + 15% sugar) was added for a total volume of 200 μL / well, after which the plate was sealed with parafilm through which a mixed population of cotton aphids (Aphis gossypii) could suck the compound preparation.

[0403] After 5 days, the mortality rate (%) is calculated, where 100% means that all cotton aphids have died, and 0% means that no cotton aphids have died.

[0404] In this test, for example, the following compounds of the Preparation Examples showed 100% good activity at an application rate of 100 ppm: I-4, I-5, I-7, I-9, I-10, I-24, I-27.

[0405] Diabrotica balteata - spray test Solvent: 78.0 parts by weight acetone 1.5 parts by weight of dimethylformamide Emulsifier: Alkylaryl polyglycol ether To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the above amount of solvent, and the resulting concentrate is diluted with water containing an emulsifier at a concentration of 1000 ppm to the desired concentration. Further test concentrations are prepared by diluting with water containing an emulsifier.

[0406] Soaked wheat (Triticum aestivum) seeds are placed in a multi-well plate filled with agar and a small amount of water and incubated for one day to germinate (5 seeds per well). The germinated wheat seeds are sprayed with a test solution containing the desired concentration of active ingredient. Each unit is then infested with 10-20 Diabrotica balteata larvae.

[0407] After 7 days, efficacy (%) is determined: 100% means that all wheat seedlings grew similarly to the untreated, uninfested control; 0% means that no wheat seedlings grew.

[0408] In this test, for example, the following compounds of the Preparation Examples showed 100% good activity at an application rate of 100 g / ha (=32 μg / well): I-1, I-3, I-4, I-8, I-9, I-11, I-12, I-15, I-16, I-31, I-34, I-35, I-36, I-37, I-38, I-39, I-40, I-41.

[0409] Meloidogyne incognita - Test Solvent: 125.0 parts by weight acetone To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the above-mentioned amount of solvent and the concentrate obtained is diluted with water to the desired concentration.

[0410] A container is placed containing sand, a solution of the active ingredient, a suspension containing eggs and larvae of the sweet potato root-knot nematode (Meloidogyne incognita), and lettuce seeds. The lettuce seeds germinate and seedlings grow. Galls appear on the roots.

[0411] After 14 days, the nematicidal efficacy (%) was determined by gall formation: 100% means that no galls were observed, and 0% means that the number of galls observed on the roots of treated plants was equal to the number of galls observed on the roots of untreated control plants.

[0412] In this test, for example, the following compounds of the Preparation Examples showed good activity of 90% at an application rate of 20 ppm: I-25, I-27, I-38.

[0413] Green peach aphid (Myzus persicae) - Oral test Solvent: 100 parts by weight acetone To prepare a suitable preparation of the active compound, 1 part by weight of the active...

Claims

1. General formula (I) 【Chemistry 1】 [During the ceremony, X is O or S; A １ is N or CR ５ and A ２ is N or CR ５ and A ３ is N or CR ５ and A ４ is N or CR ５ and Here, A １ , A ２ , A ３ , A ４ at least one or two of represent nitrogen (N); R １ is hydrogen; or, in each case, optionally substituted C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cycloalkyl C １ -C ６ Alkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Haloalkenyl, C ２ -C ６ Alkynyl, C ２ -C ６ is haloalkynyl; or phenyl-C １ -C ６ Alkyl [wherein phenyl is halogen, hydroxy, -CN, -COOH, -CONH ２ , -CSNH ２ , -NO ２ , -Si(CH ３ ) ３ , -SF ５ , -NH ２ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cyanocycloalkyl, C ３ -C ６ Halocycloalkyl, C ３ -C ６ Cycloalkyl-C １ -C ６ Alkyl, C １ -C ３ Haloalkyl, C １ -C ３ Cyanoalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl, C １ -C ３ Haloalkylsulfonyl, C １ -C ３ Cyanoalkylthio, C １ -C ３ Cyanoalkylsulfinyl and C １ -C ３ cyanoalkylsulfonyl; or Heterocyclyl-C １ -C ６ alkyl, wherein the heterocyclyl is selected from the group consisting of saturated and partially unsaturated 3- to 10-membered heterocyclyl, 5-membered heteroaryl, 6-membered heteroaryl, 9-membered heteroaryl, and 10-membered heteroaryl, and wherein the heterocyclyl is selected from the group consisting of halogen, hydroxy, -CN, -COOH, -CONH ２ , -CSNH ２ , -NO ２ , -Si(CH ３ ) ３ , -SF ５ , -NH ２ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cyanocycloalkyl, C ３ -C ６ Halocycloalkyl, C ３ -C ６ Cycloalkyl-C １ -C ６ Alkyl, C １ -C ３ Haloalkyl, C １ -C ３ Cyanoalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl, C １ -C ３ Haloalkylsulfonyl, C １ -C ３ Cyanoalkylthio, C １ -C ３ Cyanoalkylsulfinyl and C １ -C ３ cyanoalkylsulfonyl; R ２ is phenyl or 5- or 6-membered heteroaryl, each of which is Halogen, hydroxyl, -CN, -COOH, -NO ２ , -NH ２ , -SO ２ N.H. ２ , -SF ５ ; And, C, which may in any case be substituted １ -C ６ Alkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Alkynyl, C ３ -C ６ Cycloalkyl, C １ -C ６ Haloalkyl, C １ -C ６ Alkoxy, C ３ -C ６ Cycloalkoxy, C １ -C ６ Haloalkoxy, Hydroxy-C １ -C ６ Alkyl, -CO ２ C １ -C ６ Alkyl, -NH(C １ -C ６ alkyl), -N(C １ -C ６ Alkyl) ２ , S.C. １ -C ６ Alkyl sulfinimidoyl, S-C ３ -C ６ Cycloalkylsulfinimidoyl, S-C ２ -C ６ Alkenylsulfinimidoyl, S-C ２ -C ６ Alkynylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S-C １ -C ６ Alkyl sulfonimidoyl, S-C ３ -C ６ Cycloalkylsulfonimidoyl, S-C ２ -C ６ Alkenylsulfonimidoyl, S-C ２ -C ６ Alkynylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, -C(=NOC １ -C ６ Alkyl)H, -C(=NOC １ -C ６ Alkyl)-C １ -C ６ Alkyl and (C １ -C ６ Alkyl) ３ - silyl; and Substructures S1-S9, where the bond to the phenyl or 5- or 6-membered heteroaryl is marked with a #, and Z is CO or CS, and Y is CO and SO ２ are independently selected from: 【Chemistry 2】 [where: R ２１ is hydrogen or, in each case, optionally substituted C １ -C ６ Alkyl, C １ -C ６ Haloalkyl, C ３ -C ６ Cycloalkyl, -C １ -C ６ Alkyl-C ３ -C ６ cycloalkyl, phenyl, heteroaryl and heterocyclyl; R ２２ is hydrogen or, in each case, optionally substituted C １ -C ６ Alkyl, C １ -C ６ Haloalkyl, -C １ -C ６ Alkyl-C ３ -C ６ Cycloalkyl and C ３ -C ６ is cycloalkyl; R ２３ is optionally substituted C １ -C ６ Alkyl, C １ -C ６ Haloalkyl, C ３ -C ６ independently selected from cycloalkyl and phenyl; R ２４ is optionally substituted C １ -C ６ Alkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Alkynyl, C １ -C ６ Haloalkyl, C ３ -C ６ cycloalkyl, phenyl, heteroaryl and heterocyclyl; or R ２１ and R ２２ together with the nitrogen atom to which they are attached represent an optionally substituted mono- or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl, which may contain further heteroatoms; and - 3-6 membered heterocyclyl or 5-6 membered heteroaryl, each containing 1 or 2 heteroatoms selected from the group consisting of N, O and S, wherein the 3-6 membered heterocyclyl substituent or the 5-6 membered heteroaryl substituent is selected from halogen, hydroxy, -CN, -COOH, -CONH ２ , -CSNH ２ , -NO ２ , -Si(CH ３ ) ３ , -SF ５ , -NH ２ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cyanocycloalkyl, C ３ -C ６ Halocycloalkyl, C ３ -C ６ Cycloalkyl-C １ -C ６ Alkyl, C １ -C ３ Haloalkyl, C １ -C ３ Cyanoalkyl, C ３ -C ６ Cyanocycloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl, C １ -C ３ Haloalkylsulfonyl, C １ -C ３ Cyanoalkylthio, C １ -C ３ Cyanoalkylsulfinyl and C １ -C ３ cyanoalkylsulfonyl; R ３ is hydrogen or C １ -C ６ Alkyl [wherein the alkyl is selected from the group consisting of halogen, —CN, C ３ -C ６ -Cycloalkyl and C １ -C ６ -, optionally substituted with 1 to 3 substituents selected from alkoxy; R ４ is a monocyclic heterocycle selected from the group consisting of 5-membered heteroaryl and 6-membered heteroaryl, each of which contains 1 or 2 heteroatoms selected from the group consisting of N, O and S, and each of which is Halogen, hydroxyl, -CN, -COOH, -NO ２ , -NH ２ , -SF ５ ; And, C, which may in any case be substituted １ -C ６ Alkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Alkynyl, C ３ -C ６ Cycloalkyl, -C １ -C ６ Alkyl-C ３ -C ６ Cycloalkyl, C １ -C ６ Haloalkyl, C １ -C ６ Alkoxy, C ３ -C ６ Cycloalkoxy, C １ -C ６ Haloalkoxy, C １ -C ６ Cyanoalkoxy, hydroxy-C １ -C ６ Alkyl, -NH(C １ -C ６ alkyl), -NH(C １ -C ６ Alkyl-C ３ -C ６ cycloalkyl), -N(C １ -C ６ Alkyl) ２ , -N(C １ -C ６ Alkyl) (C １ -C ６ Alkyl-C ３ -C ６ Cycloalkyl), -CO ２ C １ -C ６ Alkyl, S-C １ -C ６ Alkyl sulfinimidoyl, S-C ３ -C ６ Cycloalkylsulfinimidoyl, S-C ２ -C ６ Alkenylsulfinimidoyl, S-C ２ -C ６ Alkynylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S-C １ -C ６ Alkyl sulfonimidoyl, S-C ３ -C ６ Cycloalkylsulfonimidoyl, S-C ２ -C ６ Alkenylsulfonimidoyl, S-C ２ -C ６ Alkynylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, -C(=NOC １ -C ６ Alkyl)H and -C(=NOC １ -C ６ Alkyl)-C １ -C ６ Alkyl; and - 3-6 membered heterocyclyl containing 1 or 2 heteroatoms selected from the group consisting of N, O and S, wherein the 3-6 membered heterocyclyl substituents are halogen, hydroxy, -CN, -COOH, -CONH ２ , -CSNH ２ , -NO ２ , -Si(CH ３ ) ３ , -SF ５ , -NH ２ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cyanocycloalkyl, C ３ -C ６ Halocycloalkyl, C ３ -C ６ Cycloalkyl-C １ -C ６ Alkyl, C １ -C ３ Haloalkyl, C １ -C ３ Cyanoalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl, C １ -C ３ Haloalkylsulfonyl, C １ -C ３ Cyanoalkylthio, C １ -C ３ Cyanoalkylsulfinyl and C １ -C ３ cyanoalkylsulfonyl; and The following substructures S10-S18, where the bonds to the 5-membered and 6-membered heteroaryls are marked with #, and Z is CO or CS, and Y is CO and SO ２ are independently selected from: 【Chemistry 3】 [where: R ４１ is hydrogen or, in each case, optionally substituted C １ -C ６ Alkyl, C １ -C ６ Haloalkyl, C ３ -C ６ Cycloalkyl, -C １ -C ６ Alkyl-C ３ -C ６ cycloalkyl, phenyl, heteroaryl and heterocyclyl; R ４２ is hydrogen or, in each case, optionally substituted C １ -C ６ Alkyl, C １ -C ６ Haloalkyl, C １ -C ６ Cyanoalkyl, -C １ -C ６ Alkyl-C ３ -C ６ Cycloalkyl or C ３ -C ６ is cycloalkyl; R ４３ is optionally substituted C １ -C ６ Alkyl, C １ -C ６ Haloalkyl, C ３ -C ６ independently selected from cycloalkyl and phenyl; R ４４ is optionally substituted C １ -C ６ Alkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Alkynyl, C １ -C ６ Haloalkyl, C ３ -C ６ cycloalkyl, phenyl, heteroaryl and heterocyclyl; or R ４１ and R ４２ together with the nitrogen atom to which they are attached represent an optionally substituted mono- or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl, which may contain additional heteroatoms; R ５ is hydrogen, halogen, -CN, -NH ２ or in each case optionally substituted C １ -C ３ -Alkyl, C １ -C ３ -Haloalkyl, C １ -C ３ Cyanoalkyl, C ３ -C ４ -Cycloalkyl, C ３ -C ４ Halocycloalkyl, C ３ -C ６ Cyanocycloalkyl, C １ -C ３ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkoxy, -CO ２ (C １ -C ３ alkyl), -CH-(C １ -C ３ Alkoxy) ２ , -CONH(C １ -C ４ alkyl), -CON(C １ -C ４ Alkyl) ２ , -NHCO-C １ -C ４ Alkyl, -N(C １ -C ４ Alkyl)CO-C １ -C ４ Alkyl, -C(=NOC １ -C ４ Alkyl)H, -C(=NOC １ -C ４ Alkyl)-C １ -C ４ Alkyl, -NH(C １ -C ３ alkyl), -N(C １ -C ３ Alkyl) ２ , C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C ３ -C ６ Cycloalkylthio, C ３ -C ６ Cycloalkylsulfinyl or C ３ -C ６ cycloalkylsulfonyl. and salts and N-oxides thereof.

2. X is O or S; A １ is N or CR ５ and A ２ is N or CR ５ and A ３ is N or CR ５ and A ４ is N or CR ５ where A １ , A ２ , A ３ , A ４ one or two of represent nitrogen (N); R １ is hydrogen; or C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cycloalkyl C １ -C ６ Alkyl [wherein each of these is a halogen, —CN, C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Alkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl and C １ -C ３ alkylsulfonyl; or C ２ -C ６ Alkenyl, C ２ -C ６ Haloalkenyl, C ２ -C ６ Alkynyl, C ２ -C ６ haloalkynyl; or Phenyl-C １ -C ３ Alkyl [wherein phenyl is halogen, —CN, —NO ２ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl and C １ -C ３ haloalkylsulfonyl; or Heterocyclyl-C １ -C ３ alkyl, wherein the heterocyclyl is selected from the group consisting of saturated or partially unsaturated 3- to 10-membered heterocyclyl, 5-membered heteroaryl, 6-membered heteroaryl, 9-membered heteroaryl, and 10-membered heteroaryl, and the heterocyclyl is selected from the group consisting of halogen, —CN, —NO ２ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl and C １ -C ３ haloalkylsulfonyl; R ２ is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine, pyridazine, thiophene and pyrazole, each of which is Halogen, hydroxyl, -CN, -COOH, -NO ２ , -NH ２ , -SO ２ N.H. ２ , -SF ５ ; -CN, -OH or C ３ -C ６ C optionally substituted with cycloalkyl １ -C ６ Alkyl; C optionally substituted with halogen and -CN ２ -C ６ Alkenyl; C optionally substituted with halogen and -CN ２ -C ６ Alkynyl; halogen, -CN, C １ -C ３ Alkyl or C １ -C ３ C optionally substituted with haloalkyl ３ -C ６ Cycloalkyl; -CN or C １ -C ６ C optionally substituted with alkoxy １ -C ６ Haloalkyl; C optionally substituted with -CN １ -C ６ Alkoxy; C optionally substituted with halogen or -CN ３ -C ６ Cycloalkoxy; C １ -C ６ Haloalkoxy, —CO ２ C １ -C ６ Alkyl, -NH(C １ -C ６ Alkyl), -N(C １ -C ６ Alkyl) ２ , S.C. １ -C ６ Alkyl sulfinimidoyl, S-C ３ -C ６ Cycloalkylsulfinimidoyl, S-C ２ -C ６ Alkenylsulfinimidoyl, S-C ２ -C ６ Alkynylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S-C １ -C ６ Alkyl sulfonimidoyl, S-C ３ -C ６ Cycloalkylsulfonimidoyl, S-C ２ -C ６ Alkenylsulfonimidoyl, S-C ２ -C ６ Alkynylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, -C(=NOC １ -C ６ Alkyl)H, -C(=NOC １ -C ６ Alkyl)-C １ -C ６ Alkyl and (C １ -C ６ Alkyl) ３ - silyl; and Substructures S1-S9, where the bonds to phenyl, pyridine, pyrimidine, pyrazine, pyridazine, thiophene and pyrazole are marked with # and Z is CO or CS and Y is CO and SO ２ are independently selected from: 【Chemistry 4】 [where: R ２１ is hydrogen, C １ -C ６ Alkyl, C １ -C ６ Cyanoalkyl, C １ -C ６ Haloalkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cyanocycloalkyl, -C １ -C ６ Alkyl-C ３ -C ６ cycloalkyl, phenyl, heteroaryl or heterocyclyl, where phenyl, heteroaryl and heterocyclyl are halogen, —CN, —NO ２ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl and C １ -C ３ haloalkylsulfonyl; R ２２ is hydrogen, C １ -C ６ Alkyl, C １ -C ６ Haloalkyl, -C １ -C ６ Alkyl-C ３ -C ６ Cycloalkyl or C ３ -C ６ is cycloalkyl; R ２３ is optionally substituted C １ -C ６ Alkyl, C １ -C ６ Haloalkyl, C ３ -C ６ independently selected from cycloalkyl and phenyl; R ２４ is C １ -C ６ Alkyl, C １ -C ６ Cyanoalkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Alkynyl, C １ -C ６ Haloalkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cyanocycloalkyl, phenyl, heteroaryl and heterocyclyl, where phenyl, heteroaryl and heterocyclyl are halogen, —CN, —NO ２ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl, C １ -C ３ haloalkylsulfonyl; or R ２１ and R ２２ together with the nitrogen atom to which they are attached represent a mono- or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl, which may contain further heteroatoms, and the mono- or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl may each be selected from the group consisting of halogen, -CN, -C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl and C １ -C ３ haloalkylsulfonyl; and - 3-6 membered heterocyclyl or 5-6 membered heteroaryl, each containing 1 or 2 heteroatoms selected from the group consisting of N, O and S, wherein the 3-6 membered heterocyclyl substituent or the 5-6 membered heteroaryl substituent is selected from halogen, hydroxy, -CN, C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cyanocycloalkyl, C ３ -C ６ Halocycloalkyl, C ３ -C ６ Cycloalkyl-C １ -C ６ Alkyl, C １ -C ３ Haloalkyl, C １ -C ３ Cyanoalkyl, C ３ -C ６ Cyanocycloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl, C １ -C ３ Haloalkylsulfonyl, C １ -C ３ Cyanoalkylthio, C １ -C ３ Cyanoalkylsulfinyl and C １ -C ３ cyanoalkylsulfonyl; and optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of: R ３ is hydrogen or C １ -C ６ Alkyl [wherein the alkyl is selected from the group consisting of halogen, —CN, C ３ -C ６ -Cycloalkyl and C １ -C ６ -, optionally substituted with 1 to 3 substituents selected from the group consisting of alkoxy; R ４ is a monocyclic heterocycle selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine and thiazole, each of which is Halogen, hydroxyl, -CN, -COOH, -NO ２ , -NH ２ , -SF ５ ; ・C １ -C ６ Alkyl, C １ -C ６ Cyanoalkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Alkynyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cyanocycloalkyl, C ３ -C ６ Halocycloalkyl, -C １ -C ６ Alkyl-C ３ -C ６ Cycloalkyl, C １ -C ６ Haloalkyl, C １ -C ６ Alkoxy, C ３ -C ６ Cycloalkoxy, C １ -C ６ Haloalkoxy, C １ -C ６ Cyanoalkoxy, hydroxy-C １ -C ６ Alkyl, -NH(C １ -C ６ alkyl), -NH(C １ -C ６ Alkyl-C ３ -C ６ cycloalkyl), -N(C １ -C ６ Alkyl) ２ , -N(C １ -C ６ Alkyl) (C １ -C ６ Alkyl-C ３ -C ６ Cycloalkyl), -CO ２ C １ -C ６ Alkyl, S-C １ -C ６ Alkyl sulfinimidoyl, S-C ３ -C ６ Cycloalkylsulfinimidoyl, S-C ２ -C ６ Alkenylsulfinimidoyl, S-C ２ -C ６ Alkynylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S-C １ -C ６ Alkyl sulfonimidoyl, S-C ３ -C ６ Cycloalkylsulfonimidoyl, S-C ２ -C ６ Alkenylsulfonimidoyl, S-C ２ -C ６ Alkynylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl and -C(=NOC １ -C ６ Alkyl)H, -C(=NOC １ -C ６ Alkyl)-C １ -C ６ Alkyl; and The following substructures S10-S18, where the bonds to the 5-membered and 6-membered heteroaryls are marked with #, and Z is CO or CS, and Y is CO and SO ２ are independently selected from: 【Chemistry 5】 [where: R ４１ is hydrogen, C １ -C ６ Alkyl, C １ -C ６ Cyanoalkyl, C １ -C ６ Haloalkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cyanocycloalkyl, -C １ -C ６ Alkyl-C ３ -C ６ cycloalkyl, phenyl, heteroaryl or heterocyclyl, where phenyl, heteroaryl and heterocyclyl are halogen, —CN, —NO ２ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl and C １ -C ３ haloalkylsulfonyl; R ４２ is hydrogen, C １ -C ６ Alkyl, C １ -C ６ Haloalkyl, C １ -C ６ Cyanoalkyl, -C １ -C ６ Alkyl-C ３ -C ６ Cycloalkyl or C ３ -C ６ is cycloalkyl; R ４３ is optionally substituted C １ -C ６ Alkyl, C １ -C ６ Haloalkyl, C ３ -C ６ independently selected from cycloalkyl and phenyl; R ４４ is C １ -C ６ Alkyl, C １ -C ６ Cyanoalkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Alkynyl, C １ -C ６ Haloalkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ cyanocycloalkyl, phenyl, heteroaryl or heterocyclyl, where phenyl, heteroaryl and heterocyclyl are halogen, —CN, —NO ２ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl and C １ -C ３ haloalkylsulfonyl; Or, R ４１ and R ４２ together with the nitrogen atom to which they are attached represent a mono- or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl, which may contain further heteroatoms, and the mono- or polycyclic 3- to 12-membered saturated or unsaturated heterocyclyl may each be selected from the group consisting of halogen, -CN, -C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl and C １ -C ３ haloalkylsulfonyl; and optionally substituted with 1 or 2 substituents independently selected from the group consisting of: R ５ is hydrogen, halogen, -CN, -NH ２ , C １ -C ３ -Alkyl, C １ -C ３ -Haloalkyl, C １ -C ３ Cyanoalkyl, C ３ -C ４ -Cycloalkyl, C ３ -C ４ Halocycloalkyl, C ３ -C ６ Cyanocycloalkyl, C １ -C ３ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkoxy, -NH(C １ -C ３ Alkyl), -N(C １ -C ３ Alkyl) ２ , C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C ３ -C ６ Cycloalkylthio, C ３ -C ６ Cycloalkylsulfinyl or C ３ -C ６ cycloalkylsulfonyl; The compound of claim 1 and its salts and N-oxides.

3. X is O or S; A １ is N; A ２ is N or CR ５ and A ３ is N or CR ５ and A ４ is N or CR ５ or A １ is N or CR ５ and A ２ is N; A ３ is N or CR ５ and A ４ is N or CR ５ or A １ is N or CR ５ and A ２ is N or CR ５ and A ３ is N; A ４ is N or CR ５ or A １ is N or CR ５ and A ２ is N or CR ５ and A ３ is N or CR ５ and A ４ is N; or A １ is N; A ２ is N or CR ５ and A ３ is N or CR ５ and A ４ is N; R １ is hydrogen, C １ -C ６ Alkyl, C １ -C ３ Cyanoalkyl, C １ -C ３ Haloalkyl, C ３ -C ６ Cycloalkyl C １ -C ３ Alkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Alkynyl, C １ -C ３ Alkoxy C １ -C ３ Alkyl, C １ -C ３ Alkylthio C １ -C ３ Alkyl, C １ -C ３ Alkylsulfinyl C １ -C ３ Alkyl or C １ -C ３ Alkylsulfonyl C １ -C ３ is alkyl; R ２ is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine, pyridazine and pyrazole, where each of these is selected from the group consisting of halogen, hydroxy, -CN, -COOH, -CONH ２ , -NO ２ , -NH ２ , -SO ２ N.H. ２ , -SF ５ , C １ -C ４ Alkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Halocycloalkyl, C ３ -C ６ Cyanocycloalkyl, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C ３ -C ６ Cycloalkylsulfanyl, C ３ -C ６ Cycloalkylsulfinyl, C ３ -C ６ Cycloalkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl, C １ -C ３ Haloalkylsulfonyl, C １ -C ３ Cyanoalkoxy, hydroxy-C １ -C ４ Alkyl, -NH(C １ -C ４ alkyl), -N(C １ -C ４ Alkyl) ２ , -NHCO-C １ -C ４ Alkyl, NHCO-C ３ -C ６ Cycloalkyl, -NHSO ２ (C １ -C ４ Alkyl), -N(C １ -C ４ Alkyl)CO-C １ -C ４ Alkyl, -N(C １ -C ４ Alkyl)CO-C ３ -C ６ Cycloalkyl, -N(C １ -C ４ Alkyl)SO ２ C １ -C ４ Alkyl, -N(SO ２ C １ -C ４ Alkyl) ２ , -CO ２ C １ -C ４ Alkyl, -CONH(C １ -C ４ alkyl), -CONH(C ３ -C ６ cycloalkyl), -CONH-phenyl, -CON(C １ -C ４ Alkyl) ２ , -CON(C １ -C ４ Alkyl) (C ３ -C ６ cycloalkyl), -CON(C １ -C ４ alkyl)-phenyl, -C(=NOC １ -C ４ Alkyl)H, -C(=NOC １ -C ４ Alkyl)-C １ -C ４ Alkyl, (C １ -C ４ Alkyl) ３ -Silyl, -SO ２ NH (C １ -C ４ alkyl), phenylsulfonyl, and 3- to 6-membered heterocyclyl containing one or two heteroatoms selected from the group consisting of N, O, and S, where the phenyl group and the 3- to 6-membered heterocyclyl substituents in the above-mentioned substituents are not limited to halogen, —CN, C １ -C ４ Alkyl, C １ -C ３ Haloalkyl, C １ -C ３ Alkoxy and C １ -C ３ haloalkoxy; R ３ is hydrogen, C １ -C ６ Alkyl [wherein the alkyl is selected from the group consisting of halogen, C ３ -C ６ -Cycloalkyl or C １ -C ６ -, optionally substituted with 1 to 3 substituents selected from alkoxy; R ４ is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine and thiazole, each of which is selected from the group consisting of halogen, —CN, —COOH, —NO ２ , -NH ２ , -SF ５ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ４ Alkyl-C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ３ Cyanoalkyl, C ３ -C ６ Halocycloalkyl, C ３ -C ６ Cyanocycloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkoxy and -CO ２ C １ -C ６ or, optionally substituted with 1 or 2 substituents independently selected from the group consisting of alkyl; R ４ is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine and thiazole, each of which is selected from the group consisting of halogen, —CN, —COOH, —NO ２ , -NH ２ , -SF ５ , C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ４ Alkyl-C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ３ Cyanoalkyl, C ３ -C ６ Halocycloalkyl, C ３ -C ６ Cyanocycloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkoxy and -CO ２ C １ -C ６ and wherein each of these is further defined as the following substructures S10-S18, in which the bonds to the pyridine, pyrimidine, pyrazine, pyridazine and thiazole are marked with a #, and Z is CO or CS, and Y is CO and SO. ２ are independently selected from: 【Chemistry 6】 [where: R ４１ is hydrogen, C １ -C ４ Alkyl, C １ -C ３ Cyanoalkyl, C １ -C ３ Haloalkyl, C ３ -C ６ Cycloalkyl or -C １ -C ３ Alkyl-C ３ -C ６ is cycloalkyl; R ４２ is hydrogen, C １ -C ４ Alkyl, C １ -C ３ Cyanoalkyl, C １ -C ３ Haloalkyl, C ３ -C ６ Cycloalkyl or -C １ -C ３ Alkyl-C ３ -C ６ is cycloalkyl; R ４３ is C １ -C ４ Alkyl, C １ -C ３ Haloalkyl or C ３ -C ６ is cycloalkyl; R ４４ is C １ -C ４ Alkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Alkynyl, C １ -C ３ Haloalkyl or C ３ -C ６ is cycloalkyl; Or, R ４１ and R ４２ together with the nitrogen atom to which they are attached represent a mono- or polycyclic 5- to 6-membered saturated or unsaturated heterocyclyl, which may contain further heteroatoms, and the mono- or polycyclic 1- to 6-membered saturated or unsaturated heterocyclyl may each be selected from the group consisting of halogen, -CN, -C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl and C １ -C ３ haloalkylsulfonyl; and is substituted with one substituent selected from the group consisting of: R ５ is hydrogen, halogen, -CN, C １ -C ６ -Alkyl, C １ -C ３ -Haloalkyl, C ３ -C ４ -Cycloalkyl, C １ -C ３ Alkoxy or C １ -C ３ haloalkoxy; 3. The compound according to claim 1 or 2, and its salts and N-oxides.

4. X is O or S; A １ is N; A ２ is N or CR ５ and A ３ is N or CR ５ and A ４ is N or CR ５ or A １ is N or CR ５ and A ２ is N; A ３ is N or CR ５ and A ４ is N or CR ５ or A １ is N or CR ５ and A ２ is N or CR ５ and A ３ is N; A ４ is N or CR ５ or A １ is N or CR ５ and A ２ is N or CR ５ and A ３ is N or CR ５ and A ４ is N; or A １ is N; A ２ is N or CR ５ and A ３ is N or CR ５ and A ４ is N; R １ is hydrogen, methyl, ethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, methoxyethyl, methylthioethyl, methylsulfinylethyl or methylsulfonylethyl; R ２ gives the substructures Q1, Q2 and Q3 (where the bond to the C=X-group is marked with a #): 【Chemistry 7】 [where: R ２５ is hydroxy, -CN, -NH ２ , -SO ２ N.H. ２ , C １ -C ４ Alkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Halocycloalkyl, C ３ -C ６ Cyanocycloalkyl, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C ３ -C ６ Cycloalkylsulfanyl, C ３ -C ６ Cycloalkylsulfinyl, C ３ -C ６ Cycloalkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl, C １ -C ３ Haloalkylsulfonyl, C １ -C ３ Cyanoalkoxy, hydroxy-C １ -C ４ Alkyl, -NH(C １ -C ４ Alkyl), -N(C １ -C ４ Alkyl) ２ , -NHCO-C １ -C ４ Alkyl, NHCO-C ３ -C ６ Cycloalkyl, -NHSO ２ (C １ -C ４ Alkyl), -N(C １ -C ４ Alkyl)CO-C １ -C ４ Alkyl, -N(C １ -C ４ Alkyl)CO-C ３ -C ６ Cycloalkyl, -N(C １ -C ４ Alkyl)SO ２ C １ -C ４ Alkyl, -N(SO ２ C １ -C ４ Alkyl) ２ , -CO ２ C １ -C ４ Alkyl, -CONH(C １ -C ４ alkyl), -CONH(C ３ -C ６ cycloalkyl), -CONH-phenyl, -CON(C １ -C ４ Alkyl) ２ , -CON(C １ -C ４ Alkyl) (C ３ -C ６ cycloalkyl), -CON(C １ -C ４ alkyl)-phenyl, -C(=NOC １ -C ４ Alkyl)H, -C(=NOC １ -C ４ Alkyl)-C １ -C ４ Alkyl, (C １ -C ４ Alkyl) ３ -Silyl, -SO ２ NH (C １ -C ４ alkyl), phenylsulfonyl, or 3- to 6-membered heterocyclyl containing one or two heteroatoms selected from the group consisting of N, O, and S, where the phenyl group and the 3- to 6-membered heterocyclyl substituents of the above substituents are not limited to halogen, —CN, C １ -C ４ Alkyl, C １ -C ３ Haloalkyl, C １ -C ３ Alkoxy and C １ -C ３ haloalkoxy); and R ２６ is hydrogen, halogen, -CN, -COOH, -CONH ２ , -NO ２ , C １ -C ４ Alkyl, C １ -C ３ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Alkylthio, C １ -C ３ Alkylsulfinyl, C １ -C ３ Alkylsulfonyl, C １ -C ３ Haloalkylthio, C １ -C ３ Haloalkylsulfinyl, C １ -C ３ Haloalkylsulfonyl, C ３ -C ６ Cycloalkylsulfanyl, C ３ -C ６ Cycloalkylsulfinyl, C ３ -C ６ Cycloalkylsulfonyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Cyanoalkyl or C ３ -C ６ is cyanocycloalkyl; R ２７ is hydrogen or C １ -C ４ is alkyl] Selected from: R ３ is methyl; R ４ is selected from the group consisting of pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrazin-3-yl, and 1,3-thiazol-2-yl, each of which is optionally substituted with one substituent independently selected from the group consisting of fluorine, chlorine, bromine, -CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, difluoroethoxy, methoxycarbonyl, and ethoxycarbonyl; or The following structure S13 (wherein the bonds to the pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrazin-3-yl and 1,3-thiazol-2-yl are marked with # and Z is CO): 【Chemistry 8】 [where: R ４１ is hydrogen, methyl, ethyl, cyclopropylmethyl, cyanomethyl, cyclopropyl, difluoroethyl or trifluoroethyl; R ４２ is hydrogen, methyl, ethyl, cyclopropylmethyl, cyanomethyl, cyclopropyl, difluoroethyl or trifluoroethyl; or R ４１ and R ４２ together with the nitrogen atom to which they are attached represent morpholine which may be substituted with 1 to 4 methyl; R ５ is hydrogen, fluorine, chlorine, bromine, iodine, --CN, methyl, ethyl, isopropyl, difluoromethyl, trifluoromethyl, cyclopropyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy; compounds according to claim 1 or 2, as well as salts and N-oxides thereof.

5. X is O; A １ is N; A ２ is CR ５ and A ３ is CR ５ and A ４ is CR ５ or A １ is CR ５ and A ２ is CR ５ and A ３ is N; A ４ is CR ５ or A １ is CR ５ and A ２ is CR ５ and A ３ is CR ５ and A ４ is N; R １ is hydrogen; R ２ are 3-chloro-5-(trifluoromethoxy)phenyl, 3-bromo-5-(trifluoromethoxy)phenyl, 3-cyano-5-(trifluoromethoxy)phenyl, 3,5-bis(difluoromethyl)phenyl, 3,5-bis-(trifluoromethyl)phenyl, 3,5-bis(difluoromethoxy)phenyl, 3,5-bis-(trifluoromethoxy)phenyl, 3-(1,1-difluoroethyl)-5-(trifluoromethoxy)phenyl, 3-cyclopropyl-5-(trifluoromethoxy)phenyl, 3-cyano-5-(1-cyano-1-methyl-ethyl)phenyl, 3-(1-cyano-1-methyl-ethyl)phenyl, 3-(1-cyanocyclopropyl)-5-(trifluoromethoxy)phenyl, 3-cyclopropyl-5-(trifluoromethoxy)phenyl, 3-cyano-5-(1-cyanocyclopropyl)phenyl, 3-(1-cyanocyclopropyl)-5-(trifluoromethoxy)phenyl, (3-chloro-5-methylsulfonylphenyl), 3-methylsulfonyl-5-(trifluoromethoxy)phenyl, 3-(difluoromethylsulfonyl)-5-(trifluoromethoxy)phenyl, 3,5-bis(difluoromethylsulfonyl)phenyl and 5-(difluoromethyl)-1-methyl-pyrazol-3-yl; R ３ is methyl; R ４ is selected from the group consisting of pyrimidin-2-yl, 5-chloro-pyridin-2-yl, 5-cyano-pyridin-2-yl, 5-methoxycarbonyl-2-pyridyl, 5-(aminocarbonyl)pyridin-2-yl, 5-(methylcarbamoyl)pyridin-2-yl and 5-(dimethylaminocarbonyl)pyridin-2-yl; R ５ is selected from hydrogen, fluorine and methyl; 3. The compound according to claim 1 or 2, and its salts and N-oxides.

6. Formula (I-a) 【Chemistry 9】 [In the formula, structural element A １ , A ２ , A ３ , A ４ , R １ , R ２ , R ３ , R ４ and X has the meaning given in claim 1 or the meaning given in claim 2. The compound according to claim 1 or 2, characterized in that it has a structure represented by:

7. Formula (Ib) 【Chemistry 10】 [In the formula, structural element A １ , A ２ , A ３ , A ４ , R １ , R ２ , R ３ , R ４ and X has the meaning given in claim 1 or the meaning given in claim 2. The compound according to claim 1 or 2, characterized in that it has a structure represented by:

8. Compound: 6-[2-[(1S)-1-aminoethyl]imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile hydrochloride; 1-[3-(5-chloro-2-pyridyl)imidazo[4,5-b]pyridin-2-yl]ethanamine; 2,2,2-trifluoroacetic acid; 6-[2-(1-aminoethyl)-7-methyl-imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile hydrochloride; Methyl 6-[2-(1-aminoethyl)imidazo[4,5-b]pyridin-3-yl]pyridine-3-carboxylate hydrochloride; 6-[2-[1-aminoethyl]-6-methyl-imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile hydrochloride; 6-[2-[1-aminoethyl]-5-methyl-imidazo[4,5-b]pyridin-3-yl]pyridine-3-carbonitrile hydrochloride; 1-[1-(5-chloro-2-pyridyl)imidazo[4,5-c]pyridin-2-yl]ethanamine hydrochloride; 1-[1-(5-chloropyridin-2-yl)-1H-imidazo[4,5-b]pyridin-2-yl]ethanamine trifluoroacetate.

9. 13. Formulation, in particular an agrochemical formulation, comprising at least one compound of formula (I) according to claim 1.

10. 10. The formulation of claim 9, further comprising at least one bulking agent and / or at least one surfactant.

11. 11. Formulation according to claim 9 or 10, characterized in that the compound of formula (I) is mixed with at least one further active compound.

12. A method for controlling pests (particularly insect pests), characterized in that a compound of formula (I) according to claim 1 or 2 or a formulation according to claim 9 or 10 is applied to the pests and / or their habitat, wherein methods of treating the animal body by surgery or therapy and diagnostic methods carried out on the animal body are excluded.

13. 13. The method of claim 12, wherein the pest is a pest and includes or is an insect, arachnid or nematode.

14. Use of a compound of formula (I) as defined in claim 1 or 2 or a formulation as defined in claim 9 or 10 for controlling pests, in which methods of treating the animal body by surgery or therapy and diagnostic methods performed on the animal body are excluded.

15. 15. The use according to claim 14, characterized in that the pest comprises or is an insect, an arachnid or a nematode.

16. 15. Use according to claim 14 in crop protection.

17. 15. The use according to claim 14 in the field of animal health.

18. 15. Use of a compound or salt according to claim 14 in vector control.

19. A method for protecting seeds or germinating plants against pests, in particular insect pests, comprising the method step of contacting the seeds with a compound of formula (I) as defined in claim 1 or 2 or with a formulation as defined in claim 9 or 10.

20. A seed obtained by the method according to claim 19.

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