Heteroaryl-substituted pyrazine derivatives as pesticides

Abstract

The present invention relates to compounds of general formula (I), wherein the structural element R 1 , R 2 , R 3 , R 4 , R 5 and R 6 has the meaning given to it herein), formulations and compositions containing such compounds, and their use in controlling pests (which includes arthropods and insects) in plant protection and for controlling ectoparasites of animals. [Formula 1] TIFF2022550996000211.tif6278

Description

[Technical Field]

[0001] The present invention relates to novel heteroaryl-substituted pyrazine 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] Certain heteroaryl-triazole and heteroaryl-tetrazole 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 in the field of plant protection.

[0003] Furthermore, patent applications WO2019 / 201835 (PCT / EP2019 / 059624), WO2019 / 197468 (PCT / EP2019 / 059089), WO2019 / 202077 (PCT / EP2019 / 060081), WO2019 / 206799 (PCT / EP2019 / 060077), EP19169209.4, EP19187891.7 and EP19187899.0 (the last three not yet published) relate to triazole and tetrazole compounds, their use in crop protection and / or their use as pesticides.

[0004] WO2020 / 002563, WO2020 / 053364, WO2020 / 053365, WO2020 / 079198 and WO2020 / 169445 describe azole-amide compounds, and WO2020 / 070049 relates to pyrazine compounds, all of which can be used as insecticides.

[0005] Modern plant protection products and veterinary ectoparasiticides must meet many requirements, for example, in terms of 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 an increasingly serious problem 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 to known compounds are constantly being sought. It is particularly desirable to find new pesticides and parasiticides that overcome resistance. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] WO2017 / 192385 [Patent Document 2] WO2019 / 170626 [Patent Document 3] WO2019 / 215198 [Patent Document 4] WO2019 / 201835(PCT / EP2019 / 059624) [Patent Document 5] WO2019 / 197468(PCT / EP2019 / 059089) [Patent Document 6] WO2019 / 202077(PCT / EP2019 / 060081) [Patent Document 7] WO2019 / 206799(PCT / EP2019 / 060077) [Patent Document 8] EP19169209.4 [Patent Document 9] EP19187891.7 [Patent Document 10] EP19187899.0 [Patent Document 11] WO2020 / 002563 [Patent Document 12] WO2020 / 053364 [Patent Document 13] WO2020 / 053365 [Patent Document 14] WO2020 / 079198 [Patent Document 15] WO2020 / 169445 [Patent Document 16] WO2020 / 070049 Summary of the Invention [Problem to be solved by the invention]

[0007] It was an object of the present invention to provide compounds that broaden the spectrum of pesticides in various respects. [Means for solving the problem]

[0008] Thus, in a first aspect (Aspect 1.1), the present invention provides compounds of general formula (I) [ka]

[0009] [During the ceremony, R 1 is hydrogen; 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, and 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 and optionally substituted by 1 to 5 substituents independently selected from the group consisting of -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. and; R 2is phenyl or a 5- or 6-membered heteroaryl, each of which is optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of: Halogen, hydroxy, -CN, -COOH, -NO2, -NH2, -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, each of which may be substituted. , 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, (C1-C6 alkyl)3-silyl; and Structures 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 or SO; [ka]

[0010] R 21is 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; 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, 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 additional 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 and optionally have 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; R 3 is hydrogen or C1-C6 alkyl, wherein the alkyl is optionally substituted with 1 to 3 substituents selected from halogen, C3-C6-cycloalkyl and C1-C6-alkoxy; R 4 is a monocyclic heterocycle selected from the group consisting of 5-membered heteroaryl, 6-membered heteroaryl, and 3- to 6-membered heterocyclyl, each of which contains 1 or 2 heteroatoms selected from the group consisting of N, O, and S, and each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from the group consisting of: 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, C3-C6 halocycloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C1-C6 haloalkoxy, 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, —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 and optionally having one, two, three, or four 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 Structures S10-S18 below, wherein the bond to the pyrazine is marked with a #, and Z is CO or CS, and Y is independently selected from CO or SO; [ka]

[0011] 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, in each case, optionally substituted C1-C6 alkyl, C1-C6 haloalkyl and 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; R44 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; R 5 is hydrogen, halogen, -CN 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) 2, -NHCO-C1-C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, -C(=NOC1-C4 alkyl)H, or -C(=NOC1-C4 alkyl)-C1-C4 alkyl, -NH2, -NH(C1-C3 alkyl), -N(C1-C3 alkyl)2, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylthio, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl; R 6is hydrogen, halogen, -CN or, in each case, optionally substituted C1-C3-alkyl, C1-C3-haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, -CO2(C1-C3 alkyl), -CH-(C1-C3 alkoxy)2, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N(C -C(=NOC1-C4 alkyl)CO-C1-C4 alkyl, -C(=NOC1-C4 alkyl)H, or -C(=NOC1-C4 alkyl)-C1-C4 alkyl, -NH2, -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.

[0012] The compounds of formula (I) described herein further include all diastereomers or enantiomers and E / Z isomers that may exist, as well as salts and N-oxides of the compounds of formula (I).

[0013] The compounds of formula (I) described herein may, depending on the type of their substituents, exist in stereoisomeric forms, i.e. in the form of geometric and / or optical isomers or in the form of isomeric mixtures of various compositions. 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.

[0014] However, according to the invention, the optically active stereoisomeric forms of the compounds of formula (I) and their salts are preferably used.

[0015] The invention therefore relates both to the pure enantiomers and diastereomers and to their mixtures.

[0016] According to an embodiment of the present invention, dextrorotatory compounds of formula (I), i.e., isomers that rotate plane-polarized light in a clockwise ((+)) direction, are preferred. Such enantiomers are typically designated "(+)". Methods for separating enantiomers are well known in the art (e.g., separation by chiral chromatography).

[0017] R 3 At the carbon atom in formula (I) having the group R, the compounds of the invention can have the R- or S-configuration (according to the Cahn-Ingold-Prelog rules). The invention relates to compounds having the R- or S-configuration at this position and mixtures of these isomers. According to a further embodiment, R 3 Compounds of formula (I) having the S configuration at the carbon atom having the formula: are preferred.

[0018] Where appropriate, the 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 and can be used in accordance with the present invention.

[0019] The present invention further relates to preferred embodiments defined in the following aspects of the invention.

[0020] According to the following embodiments, compounds of formula (I) are excluded from the present invention.

[0021] (i) According to one embodiment, a compound of formula (I), wherein R 2is phenyl, pyridine, pyrimidine, pyrazine, or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine, or pyridazine is optionally substituted with 1 to 3 substituents, provided that no substituents are present on either carbon adjacent to the carbon to which C=O is attached, and each substituent is independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, NO2, SF5, CN, CONH2, COOH, and C(S)NH2.

[0022] (ii) According to a further embodiment, a compound of formula (I), wherein R 2 is phenyl or pyridine, wherein the phenyl or pyridine is optionally substituted with one or two substituents, provided that no substituents are present on either carbon adjacent to the carbon to which C=O is attached, and each substituent is independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, and —CN; or, preferably, each substituent is selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, and halogen.

[0023] (iii) According to a further embodiment, a compound of formula (I), wherein R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with 1 to 3 substituents independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C3-C4 cycloalkyl, halogen and hydroxy.

[0024] (iv) According to a further embodiment, a compound of formula (I), wherein R 4is a pyridine or pyrimidine, wherein the pyridine or pyrimidine is optionally substituted with one substituent selected from C1-C3 alkyl, C3-C4 cycloalkyl, or halogen, or hydroxy; or, preferably, the pyridine or pyrimidine is optionally substituted with one substituent selected from C3-C4 cycloalkyl, or halogen and hydroxy; or, more preferably, the pyridine or pyrimidine is optionally substituted with one substituent selected from C3-C4 cycloalkyl, F, Cl, and Br.

[0025] (v) According to a further embodiment, a compound of formula (I) wherein: R 2 is phenyl, pyridine, pyrimidine, pyrazine, or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine, or pyridazine is optionally substituted with 1 to 3 substituents, provided that no substituents are present on either carbon adjacent to the carbon to which C=O is attached, and each substituent is independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, NO2, SF5, CN, CONH2, COOH, and C(S)NH2; and at the same time, R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with 1 to 3 substituents independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C3-C4 cycloalkyl, halogen or hydroxy.

[0026] (vi) According to a further embodiment, a compound of formula (I) R 2is phenyl, pyridine, pyrimidine, pyrazine, or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine, or pyridazine is optionally substituted with 1 to 3 substituents, provided that no substituents are present on either carbon adjacent to the carbon to which C=O is attached, and each substituent is independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, NO2, SF5, CN, CONH2, COOH, and C(S)NH2; and at the same time, R 4 is a pyridine or pyrimidine, wherein the pyridine or pyrimidine is optionally substituted with one substituent selected from C1-C3 alkyl, C3-C4 cycloalkyl, or halogen, or hydroxy; or, preferably, the pyridine or pyrimidine is optionally substituted with one substituent selected from C3-C4 cycloalkyl, or halogen and hydroxy; or, more preferably, the pyridine or pyrimidine is optionally substituted with one substituent selected from C3-C4 cycloalkyl, F, Cl, and Br.

[0027] (vii) According to a further embodiment, a compound of formula (I) R 2 is phenyl or pyridine, wherein the phenyl or pyridine is optionally substituted with one or two substituents, provided that no substituents are present on either carbon adjacent to the carbon to which C=O is attached, and each substituent is independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, and -CN; or, preferably, each substituent is selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, and halogen; and at the same time, R 4is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with 1 to 3 substituents independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C3-C4 cycloalkyl, halogen or hydroxy.

[0028] (viii) According to a further embodiment, a compound of formula (I) R 2 is phenyl or pyridine, wherein the phenyl or pyridine is optionally substituted with one or two substituents, provided that no substituents are present on either carbon adjacent to the carbon to which C=O is attached, and each substituent is independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, and -CN; or, preferably, each substituent is selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, and halogen; and at the same time, R 4 is a pyridine or pyrimidine, wherein the pyridine or pyrimidine is optionally substituted with one substituent selected from C1-C3 alkyl, C3-C4 cycloalkyl, or halogen, or hydroxy; or, preferably, the pyridine or pyrimidine is optionally substituted with one substituent selected from C3-C4 cycloalkyl, or halogen and hydroxy; or, more preferably, the pyridine or pyrimidine is optionally substituted with one substituent selected from C3-C4 cycloalkyl, F, Cl, and Br.

[0029] In a further aspect (Aspect 1.2), the present invention provides compounds of general formula (I) [ka]

[0030] [During the ceremony, R 1 is hydrogen; C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C3 alkoxyC1-C3 alkyl, C1-C3 alkylthioC1-C3 alkyl, C1-C3 alkylsulfinylC1-C3 alkyl, C1-C3 alkylsulfonylC1-C3 alkyl, C1-C3 haloalkyl, C1-C6 cyanoalkyl, in each case optionally substituted; or Phenyl-C1-C6 alkyl, wherein phenyl is selected from the group consisting of halogen, hydroxy, -CN, and 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 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. and; R 2is phenyl or 5- or 6-membered heteroaryl, wherein each of these is selected from the group consisting of halogen, hydroxy, CN, —COOH, —CONH2, —NO2, —NH2, SF5, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C6 cyanocycloalkyl, C1-C4 alkoxy, C3-C6 cycloalkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, hydroxy-C1-C4 alkyl, C1- C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylthio, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, C1-C3 cyanoalkylsulfonyl, alkenylthio, alkynylthio, -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) and optionally substituted by one, two, or three substituents independently selected from the group consisting of -CON(C-C alkyl), -CON(C-C cycloalkyl), -CON(C-C alkyl)-phenyl, -C(=NOC-C alkyl)H, -C(=NOC-C alkyl)-C-C alkyl, (C-C alkyl)-silyl, -SONH, -SONH(C-C alkyl), phenylsulfonyl, and 3- to 6-membered heterocyclyl, wherein the heterocyclyl contains one or two heteroatoms selected from the group consisting of N, O, and S; Here, the phenyl group of the above substituents and the above 3- to 6-membered heterocyclyl substituents are selected from halogen, hydroxy, -CN, -COOH, -CONH2, -CSNH2, -NO2, -Si(CH3)3, -SF5, -NH2, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C6 cyanocycloalkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C6 cyanocycloalkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C6 cyanocycloalkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C1-C3 cyanocycloalkyl, C1-C4 alkoxy, C1-C3 halo ... may have 1, 2, 3, or 4 substituents independently selected from the group consisting of alkoxy, 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 3 is hydrogen or optionally substituted C1-C6 alkyl; R 4is a monocyclic heterocycle selected from the group consisting of 5-membered heteroaryl, 6-membered heteroaryl, and 3- to 6-membered heterocyclyl, each of which contains 1 or 2 heteroatoms selected from the group consisting of N, O, and S, and each of which is selected from halogen, hydroxy, CN, -COOH, -CONH2, -NO2, -NH2, SF5, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C4 alkyl-C3-C6 cycloalkyl, C1-C3 haloalkyl , C1-C3 cyanoalkyl, C3-C6 halocycloalkyl, C3-C6 cyanocycloalkyl, C1-C4 alkoxy, C3-C6 cycloalkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, hydroxy-C1-C4 alkyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylthio, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C 3Haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, C1-C3 cyanoalkylsulfonyl, alkenylthio, alkynylthio, -NH(C1-C4 alkyl), -NH(C1-C4 alkyl-C3-C6 cycloalkyl), -N(C1-C4 alkyl)2, -N(C1-C4 alkyl)(C1-C4 alkyl-C3-C6 cycloalkyl), -NHCO-C1-C4 alkyl, NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl-C3-C6 cycloalkyl), -N HSO2(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(C1-C4 alkyl-C3-C6 cycloalkyl), -CONH-phenyl, -CONHSO2(C1-C4 alkyl), -CON(C1-C4 alkyl)2,and optionally substituted with 1, 2, 3, or 4 substituents independently selected from the group consisting of -CON(C1-C4 alkyl)(C3-C6 cycloalkyl), -CON(C1-C4 alkyl)(C1-C4 alkyl-C3-C6 cycloalkyl), -CON(C1-C4 alkyl)-phenyl, -CON(C1-C4 alkyl)SO2(C1-C4 alkyl), -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alkyl, -SON2NH2, -SON2NH(C1-C4 alkyl), phenylsulfonyl, and 3- to 6-membered heterocyclyl, wherein the heterocyclyl contains 1 or 2 heteroatoms selected from the group consisting of N, O, and S, and wherein the phenyl group and the 3- to 6-membered heterocyclyl substituents are 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 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; R 5is hydrogen, halogen, CN 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, -C(O)-C1-C3 alkoxy, -CH-(C1-C3 alkoxy)2, -CO 2C1-C4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, -C(=NOC1-C4 alkyl)H, or -C(=NOC1-C4 alkyl)-C1-C4 alkyl, NH2, NH(C1-C3 alkyl), N(C1-C3 alkyl)2, C1-C3 alkylthio, C3-C6 cycloalkylthio; R 6 is hydrogen, halogen, CN or, in each case, optionally substituted C-C-alkyl, C-C-haloalkyl, C-C-cycloalkyl, C-C-halocycloalkyl, C-C-alkoxy, C-C-haloalkoxy, —C(O)—C-C-alkoxy, —CH—(C-C-alkoxy)2, —CO-C-C-alkyl, —CONH(C-C-alkyl), —CON(C-C-alkyl)2, —NHCO-C-C-alkyl, —N(C-C-alkyl)CO-C-C-alkyl, —C(═NOC-C-alkyl)H or —C(═NOC-C-alkyl)-C-C-alkyl, NH2, NH(C-C-alkyl), N(C-C-alkyl)2, C-C-alkylthio, C-C-cycloalkylthio. and salts and N-oxides thereof. DETAILED DESCRIPTION OF THE INVENTION

[0031] In a further embodiment (embodiment 2.1), the present invention provides a compound of formula (I) as described above, wherein: R 1is hydrogen; or C1-C6 alkyl, C3-C6 cycloalkylC1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkylthioC1-C6 alkyl, C1-C6 alkylsulfinylC1-C6 alkyl, C1-C6 alkylsulfonylC1-C6 alkyl, in each case optionally substituted, wherein said optionally substituted radicals are optionally substituted with up to three substituents independently selected from the group consisting of halogen, hydroxy, —CN, —NO2, —Si(CH3)3, —NH2 and C1-C6 alkyl; or Phenyl-C1-C6 alkyl [wherein phenyl 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 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C1-C4 alkoxy, C1-C3 halo] optionally substituted by 1 to 5 substituents independently selected from the group consisting of alkoxy, 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-C3 alkyl, wherein the heterocyclyl is selected from the group consisting of tetrahydropyranyl, tetrahydrofuranyl, oxetanyl, and azetidinyl, or heteroaryl, wherein the heteroaryl is selected from the group consisting of pyridyl, pyrimidinyl, pyrazyl, pyridazinyl, thiophenyl, furanyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl, and oxazolyl, and wherein the heteroaryl or 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 and optionally substituted by 1 to 3 substituents independently selected from the group consisting of -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. and; R 2 is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, and thiophene, each of which is optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of: Halogen, hydroxy, -CN, -COOH, -NO2, -NH2, -SF5; and C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkoxy, C1-C3 haloalkoxy, hydroxy-C1-C4 alkyl, -CO2C1-C4 alkyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alkyl and (C1- C4 alkyl)3-silyl, wherein the optionally substituted radical is optionally substituted with up to three substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkylsulfonyl, C3-C4 cycloalkylsulfonyl, C1-C3 haloalkylthio, and C1-C3 haloalkylsulfonyl; and Structures S1, S4, S7, S8 and S9, wherein the bond to the phenyl, pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole or thiophene is marked with a #, and Z is CO or CS; [ka]

[0032] R 21 is hydrogen or, in each case, optionally substituted C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, -C1-C4 alkyl-C3-C6 cycloalkyl and 3- to 6-membered heterocyclyl; R 22 is hydrogen or, in each case, optionally substituted C1-C4 alkyl, C1-C4 haloalkyl, -C1-C4 alkyl-C3-C6 cycloalkyl and C3-C6 cycloalkyl; R 24is C1-C4 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, phenyl, heteroaryl and 3-6 membered heterocyclyl, each of which may be substituted; where R 21 , R 22 and R 24 The optionally substituted radical in the definition of is optionally substituted with up to three substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C3 alkylsulfonyl, C3-C4 cycloalkylsulfonyl, C1-C3 haloalkylthio and C1-C3 haloalkylsulfonyl; Or, R 21 and R 22 together with the nitrogen atom to which they are attached form a 4-12 membered saturated or unsaturated heterocyclyl, wherein the heterocyclyl can contain up to two additional heteroatoms selected from the group of oxygen, nitrogen, and sulfur, and the heterocyclyl can be selected from halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —NO2, —SF5, and —NH2; and C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, and C1-C4 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 can have one, two, or three substituents independently 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 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, 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 3 is hydrogen or C1-C6 alkyl, wherein the alkyl is optionally substituted with halogen, cyano, C3-C6 cycloalkyl, or C1-C4 alkoxy; R 4 is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine, and thiazole, pyrazole, pyrrole, oxazole, isothiazole, isoxazole, thiophene, and imidazole, each of which is optionally substituted with one, two, or three substituents independently selected from the group consisting of: Halogen, hydroxy, -CN, -COOH, -NO2, -NH2, -SF5; and C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkoxy, C1-C3 haloalkoxy, hydroxy-C1-C4 alkyl, -CO2C1-C4 alkyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alkyl and (C1-C4 alkyl)3-silyl, each of which may be substituted. wherein the optionally substituted radical is optionally substituted with up to three substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C3 alkylsulfonyl, C3-C4 cycloalkylsulfonyl, C1-C3 haloalkylthio, and C1-C3 haloalkylsulfonyl; and Structures S10, S11, S13, S14, S16, S17 and S18, wherein the bond to the pyridine, pyrimidine, pyrazine, pyridazine, thiazole, pyrazole, pyrrole, oxazole, isothiazole, isoxazole, thiophene or imidazole is marked with a #, and Z is CO or CS; [ka]

[0033] R 41 is hydrogen or, in each case, optionally substituted C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, -C1-C4 alkyl-C3-C6 cycloalkyl and 3- to 6-membered heterocyclyl; R 42 is hydrogen or, in each case, optionally substituted C1-C4 alkyl, C1-C4 haloalkyl, -C1-C4 alkyl-C3-C6 cycloalkyl and C3-C6 cycloalkyl; R43 are independently selected from C1-C4 alkyl, C1-C4 haloalkyl, and C3-C6 cycloalkyl, each of which may be substituted; R 44 is C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, phenyl, heteroaryl and 3- to 6-membered heterocyclyl, each of which may be substituted; where R 41 , R 42 , R 43 and R 24 The optionally substituted radical in the definition of is optionally substituted with up to three substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C3 alkylsulfonyl, C3-C4 cycloalkylsulfonyl, C1-C3 haloalkylthio and C1-C3 haloalkylsulfonyl; Or, R 41 and R 42together with the nitrogen atom to which they are attached form a 4-12 membered saturated or unsaturated heterocyclyl, wherein the heterocyclyl can contain up to two additional heteroatoms selected from the group of oxygen, nitrogen, sulfur, and silicon, and the heterocyclyl can be selected from halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —NO2, —SF5, and —NH2; and C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C4 haloalkyl, C1 -C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy-C1-C6 alkyl, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, and C1-C4 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 can have one, two, or three substituents independently 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 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, 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 5is hydrogen, halogen, -CN, -NH2 or, in each case, optionally substituted C1-C3-alkyl, C3-C4-cycloalkyl, C1-C3 alkoxy, -CO2(C1-C3 alkyl), -CH-(C1-C3 alkoxy)2, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, -C(=NOC1-C -4 alkyl)H, or -C(=NOC1-C4 alkyl)-C1-C4 alkyl, -NH(C1-C3 alkyl), -N(C1-C3 alkyl)2, C1-C3 alkylthio, C3-C6 cycloalkylthio, wherein said optionally substituted radical is optionally substituted with up to three substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2 and C1-C3 alkyl; R 6 is hydrogen, halogen, -CN, -NH2 or, in each case, optionally substituted C1-C3-alkyl, C3-C4-cycloalkyl, C1-C3 alkoxy, -CO2(C1-C3 alkyl), -CH-(C1-C3 alkoxy)2, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, -C(=NOC1-C -C(=NOC1-C4 alkyl)-C1-C4 alkyl, -NH(C1-C3 alkyl), -N(C1-C3 alkyl)2, C1-C3 alkylthio, C3-C6 cycloalkylthio, wherein the optionally substituted radical is optionally substituted with up to three substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2, and C1-C3 alkyl. and salts and N-oxides thereof.

[0034] In a further embodiment (embodiment 2.2), the present invention provides a compound of formula (I) as described above, wherein: R 1is hydrogen; or C1-C6 alkyl, C3-C6 cycloalkylC1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C3 alkoxyC1-C3 alkyl, C1-C3 alkylthioC1-C3 alkyl, C1-C3 haloalkyl, C1-C6 cyanoalkyl, in each case optionally substituted; or Phenyl-C1-C6 alkyl, wherein phenyl is selected from the group consisting of halogen, hydroxy, -CN, and 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 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. and; R 2is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene, and imidazole, wherein each of these is selected from the group consisting of halogen, hydroxy, CN, —COOH, —CONH2, —NO2, —NH2, SF5, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C6 cyanocycloalkyl, C1-C4 alkoxy, C1-C3 halo ... oxy, C1-C3 cyanoalkoxy, hydroxy-C1-C4 alkyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, C1-C3 cyanoalkylsulfonyl, -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)( optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of C3-C6 cycloalkyl), -CON(C1-C4 alkyl)-phenyl, -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alkyl, (C1-C4 alkyl)3-silyl, -SONH, -SONH(C1-C4 alkyl), phenylsulfonyl, and 3- to 6-membered heterocyclyl (wherein the heterocyclyl contains 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 of the above substituents may have 1, 2, 3, or 4 substituents independently 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 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; R 3 is hydrogen or optionally substituted C1-C6 alkyl; R 4is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine and thiazole, wherein each of these is selected from the group consisting of halogen, hydroxy, CN, -COOH, -CONH2, -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, hydroxy-C1-C4 Alkyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylthio, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, C1-C3 cyanoalkylsulfonyl, -NH(C1-C4 alkyl), -NH(C1-C4 alkyl-C3-C6 cycloalkyl), -N(C1 -C4 alkyl)2, -N(C1-C4 alkyl)(C1-C4 alkyl-C3-C6 cycloalkyl), -NHCO-C1-C4 alkyl, NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl-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(C1-C4 alkyl-C3-C6 cycloalkyl), -CONH-phenyl, -CONHSO2(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -CON(C1-C4 alkyl)(C3-C6 cycloalkyl), -CON(C1-C4 alkyl)(C1-C4 alkyl-C3-C6 cycloalkyl), -CON(C1-C4 alkyl)-phenyl, -CON(C1-C4 alkyl)SO2(C1-C4 alkyl), -C(=NOC1-C4 alkyl)H,and optionally substituted with 1, 2, 3, or 4 substituents independently selected from the group consisting of -C(=NOC1-C4 alkyl)-C1-C4 alkyl, -SON2NH2, -SON2NH(C1-C4 alkyl), phenylsulfonyl, and 3- to 6-membered heterocyclyl (wherein the heterocyclyl contains 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 substituents are selected from halogen, hydroxy, -CN, -COOH, -CONH2, -CSNH2, -NO2, -Si(CH3)3, -SF5, -NH2, C1-C6 alkyl, C3- may have 1, 2, 3, or 4 substituents independently selected from the group consisting of C6 cycloalkyl, 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; R 5 is hydrogen, halogen, CN 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, -C(O)-C1-C3 alkoxy, -CH-(C1-C3 alkoxy)2, -CO 2C1-C4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, -C(=NOC1-C4 alkyl)H or -C(=NOC1-C4 alkyl)-C1-C4 alkyl, NH2, NH(C1-C3 alkyl), N(C1-C3 alkyl)2, C1-C3 alkylthio, C3-C6 cycloalkylthio; R 6is hydrogen, halogen, CN 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, -C(O)-C1-C3 alkoxy, -CH-(C1-C3 alkoxy)2, -CO2 C1-C4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, -C(=NOC1-C4 alkyl)H or -C(=NOC1-C4 alkyl)-C1-C4 alkyl, NH2, NH(C1-C3 alkyl), N(C1-C3 alkyl)2, C1-C3 alkylthio, C3-C6 cycloalkylthio] and salts and N-oxides thereof.

[0035] In a further embodiment (embodiment 3.1), the present invention provides a compound of formula (I) as described above, wherein: R 1 is hydrogen; or C1-C6 alkyl, C3-C6 cycloalkylC1-C6 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C3 alkoxyC1-C3 alkyl, C1-C3 alkylthioC1-C3 alkyl, C1-C3 alkylsulfinylC1-C3 alkyl, C1-C3 alkylsulfonylC1-C3 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl; R 2 is selected from the group consisting of pyrazole, phenyl, pyridine, pyrimidine, pyrazine and pyridazine, each of which is optionally substituted with a total of 1, 2 or 3 substituents, wherein any 1, 2 or 3 of the substituents are independently selected from Group A consisting of: Halogen, hydroxy, -CN, -COOH, -NO2, -NH2, -SF5; and C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C3-C4 cyanocycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C4 cycloalkoxy, C1-C3 cyanoalkoxy, -CO2C1-C4 alkyl and (C1-C3 alkyl)3-silyl; And, optionally, one of the optional substituents may be selected from Group B consisting of: Structures S1, S4, S7, S8 and S9, wherein the bond to the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is marked with a # and Z is CO; [ka]

[0036] R 21 is hydrogen or, in each case, optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl; R 22 is hydrogen or, in each case, optionally substituted C1-C3 alkyl, C1-C3 haloalkyl and C3-C4 cycloalkyl; R 24 is C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl and phenyl, each of which may be substituted; where R 21 , R 22 and R 24 The optionally substituted radicals in the definition of are optionally substituted with up to three substituents independently selected from the group consisting of halogen, -CN, -NO2, -Si(CH3)3, C1-C3 alkyl, and C1-C3 haloalkyl; R 3 is hydrogen or C1-C6 alkyl; R 4is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene, and imidazole, wherein the 6-membered heteroaryl is each optionally substituted with 1, 2, or 3 substituents, and the 5-membered heteroaryl is each optionally substituted with 1 or 2 substituents, wherein in each case, up to all of the optional substituents are independently selected from Group D consisting of: Halogen, hydroxy, -CN, -COOH, -NO2, -NH2, -SF5; and C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C4 cyanocycloalkyl, C1-C3 alkoxy, C3-C4 cycloalkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, hydroxy-C1-C3 alkyl, -CO2C1-C3 alkyl, -NH(C1-C3 alkyl), -N(C1-C3 alkyl)2, -C(=NOC1-C3 alkyl)H, -C(=NOC1-C3 alkyl)-C1-C3 alkyl and (C1-C3 alkyl)3-silyl; And, optionally, one of the optional substituents may be selected from Group E consisting of: Structures S10, S13, S16, S17 and S18, wherein the bond to the pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene or imidazole is marked with a #, and Z is CO; [ka]

[0037] R 41is hydrogen or, in each case, optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, -C1-C2 alkyl-C3-C4 cycloalkyl and 3- to 6-membered heterocyclyl, wherein the heterocyclyl contains one heteroatom selected from the group consisting of N, O and S; R 42 is hydrogen or, in each case, optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, -C1-C2 alkyl-C3-C4 cycloalkyl and C3-C4 cycloalkyl; R 44 is C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, each of which may be substituted; where R 41 , R 42 and R 44 The optionally substituted substituents defined for are optionally substituted with up to two substituents independently selected from the group consisting of halogen, —CN, —NO, —Si(CH), C-C alkyl, C-C haloalkyl; Or, R 41 and R 42 together with the nitrogen atom to which they are attached, represent a monocyclic 4-8 membered saturated heterocyclyl, which may contain up to one additional heteroatom selected from the group of oxygen, nitrogen, sulfur, and silicon, and which is optionally substituted with 1-3 substituents selected from the group consisting of halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —NO2, and —NH2; and C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy; R 5 is hydrogen, halogen, —CN, C1-C3-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, C1-C3-alkoxy, C1-C3-haloalkoxy; R 6is hydrogen, halogen, —CN, C1-C3-alkyl, C1-C3-haloalkyl, C3-C4 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy] and salts and N-oxides thereof.

[0038] In a further embodiment (embodiment 3.2), the present invention provides a compound of formula (I) as described above, wherein: R 1 is hydrogen; or C1-C6 alkyl, C3-C6 cycloalkylC1-C6 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C3 alkoxyC1-C3 alkyl, C1-C3 alkylthioC1-C3 alkyl, C1-C3 alkylsulfinylC1-C3 alkyl, C1-C3 alkylsulfonylC1-C3 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl; R 2 is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine and pyridazine, each of which is optionally substituted with a total of 1, 2 or 3 substituents, wherein any 1, 2 or 3 of the substituents are independently selected from Group A consisting of: Halogen, hydroxy, -CN, -COOH, -NO2, -NH2, -SF5; and C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C3-C4 cyanocycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C4 cycloalkoxy, C1-C3 cyanoalkoxy, -CO2C1-C4 alkyl and (C1-C3 alkyl)3-silyl; And, optionally, one of the optional substituents may be selected from Group B consisting of: Structures S1, S4, S7, S8 and S9, wherein the bond to the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is marked with a # and Z is CO; [ka]

[0039] R 21 is hydrogen or, in each case, optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl; R 22 is hydrogen or, in each case, optionally substituted C1-C3 alkyl, C1-C3 haloalkyl and C3-C4 cycloalkyl; R 24 is C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl and phenyl, each of which may be substituted; where R 21 , R 22 and R 24 The optionally substituted radicals in the definition of are optionally substituted with up to three substituents independently selected from the group consisting of halogen, -CN, -NO2, -Si(CH3)3, C1-C3 alkyl, and C1-C3 haloalkyl; R 3 is hydrogen or C1-C6 alkyl; R 4 is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene, and imidazole, wherein the 6-membered heteroaryl is each optionally substituted with 1, 2, or 3 substituents, and the 5-membered heteroaryl is each optionally substituted with 1 or 2 substituents, wherein in each case, up to all of the optional substituents are independently selected from Group D consisting of: Halogen, hydroxy, -CN, -COOH, -NO2, -NH2, -SF5; and C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C4 cyanocycloalkyl, C1-C3 alkoxy, C3-C4 cycloalkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, hydroxy-C1-C3 alkyl, -CO2C1-C3 alkyl, -NH(C1-C3 alkyl), -N(C1-C3 alkyl)2, -C(=NOC1-C3 alkyl)H, -C(=NOC1-C3 alkyl)-C1-C3 alkyl and (C1-C3 alkyl)3-silyl; And, optionally, one of the optional substituents may be selected from Group E consisting of: Structures S10, S13, S16, S17 and S18, wherein the bond to the pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene or imidazole is marked with a #, and Z is CO; [ka]

[0040] R 41 is hydrogen or, in each case, optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, -C1-C2 alkyl-C3-C4 cycloalkyl and 3- to 6-membered heterocyclyl, wherein the heterocyclyl contains one heteroatom selected from the group consisting of N, O and S; R 42 is hydrogen or, in each case, optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, -C1-C2 alkyl-C3-C4 cycloalkyl and C3-C4 cycloalkyl; R 44 is C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, each of which may be substituted; where R 41 , R 42 and R 44The optionally substituted substituents defined above may be substituted with up to two substituents independently selected from the group consisting of halogen, —CN, —NO, —Si(CH), C-C alkyl, and C-C haloalkyl; Or, R 41 and R 42 together with the nitrogen atom to which they are attached, represent a monocyclic 4-8 membered saturated heterocyclyl, which may contain up to one additional heteroatom selected from the group of oxygen, nitrogen, sulfur, and silicon, and which is optionally substituted with 1-3 substituents selected from the group consisting of halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —NO2, and —NH2; and C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy; R 5 is hydrogen, halogen, —CN, C1-C3-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, C1-C3-alkoxy, C1-C3-haloalkoxy; R 6 is hydrogen, halogen, —CN, C1-C3-alkyl, C1-C3-haloalkyl, C3-C4 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy] and salts and N-oxides thereof.

[0041] In a further embodiment (embodiment 3.3), the present invention provides a compound of formula (I) as described above, wherein: R 1 is hydrogen; or C1-C6 alkyl, C3-C6 cycloalkylC1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C3 alkoxyC1-C3 alkyl, C1-C3 alkylthioC1-C3 alkyl, C1-C6 cyanoalkyl, each of which may be substituted; R 2is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine and pyridazine, wherein each of these is selected from the group consisting of halogen, hydroxy, CN, —COOH, —CONH2, —NO2, —NH2, SF5, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C6 cyanocycloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 cyanoalkoxy, hydroxy-C1-C4 alkyl, C1- C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylthio, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, NHCO-C3-C6 cycloalkyl, -NHSO2(C1-C4 alkyl) 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 and optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of (C-C alkyl)-phenyl, -C(=NOC-C alkyl)H, -C(=NOC-C alkyl)-C-C alkyl, (C-C alkyl)-silyl, -SONH, -SONH(C-C alkyl), phenylsulfonyl, and 3- to 6-membered heterocyclyl, wherein the heterocyclyl contains 1 or 2 heteroatoms selected from the group consisting of N, O, and S; wherein the phenyl group of the substituent and the 3- to 6-membered heterocyclyl substituent may have 1, 2, or 3 substituents independently selected from the group consisting of halogen, C1-C6 alkyl, and C1-C3 cyanoalkyl; R3 is hydrogen or optionally substituted C1-C6 alkyl; R 4is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine and thiazole, wherein each of these is selected from the group consisting of halogen, hydroxy, CN, -COOH, -CONH2, -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, hydroxy-C1-C4 Alkyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylthio, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, -NH(C1-C4 alkyl), -NH(C1-C4 alkyl-C3-C6 cycloalkyl), -N(C1-C4 alkyl)2, -N(C1-C4 alkyl)(C1-C4 alkyl-C3-C6 cycloalkyl), -NHC O-C1-C4 alkyl, NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl-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(C1-C4 alkyl-C3-C6 cycloalkyl), -CONH-phenyl, -CONHSO2(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -CON(C1-C4 alkyl)(C3-C6 cycloalkyl), -CON(C1-C4 alkyl)(C1-C4 alkyl-C3-C6 cycloalkyl), -CON(C1-C4 alkyl)-phenyl, -CON(C1-C4 alkyl)SO2(C1-C4 alkyl), -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alkyl, -SO2NH2, -SONH(C1-C4 alkyl),optionally substituted with 1, 2, 3, or 4 substituents independently selected from the group consisting of phenylsulfonyl and 3- to 6-membered heterocyclyl (wherein the heterocyclyl contains 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 substituents can have 1, 2, or 3 substituents independently selected from the group consisting of halogen, C1-C6 alkyl, and C1-C3 cyanoalkyl; R 5 is hydrogen, halogen, CN or C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-cycloalkyl, C-C-halocycloalkyl, C-C-cyanocycloalkyl, C-C-alkoxy, C-C-haloalkoxy, C-C-cyanoalkoxy, —C(O)—C-C-alkoxy, —CH—(C-C-alkoxy)2, —CO2C-C-alkyl, —CONH(C-C-alkyl), —CON(C-C-alkyl)2, —NHCO—C-C-alkyl, —N(C-C-alkyl)CO—C-C-alkyl, —C(═NOC-C-alkyl)H or —C(═NOC-C-alkyl)-C-C-alkyl; R 6 is hydrogen, halogen, CN or, in each case, optionally substituted C-C-alkyl, C-C-haloalkyl, C-C-cyanoalkyl, C-C-cycloalkyl, C-C-halocycloalkyl, C-C-cyanocycloalkyl, C-C-alkoxy, C-C-haloalkoxy, C-C-cyanoalkoxy, —C(O)—C-C-alkoxy, —CH—(C-C-alkoxy)2, —CO2C-C-alkyl, —CONH(C-C-alkyl), —CON(C-C-alkyl)2, —NHCO—C-C-alkyl, —N(C-C-alkyl)CO—C-C-alkyl, —C(═NOC-C-alkyl)H or —C(═NOC-C-alkyl)-C-C-alkyl. and salts and N-oxides thereof.

[0042] In a further embodiment (embodiment 4.1), the present invention provides a compound of formula (I) as described above, wherein: R 1 is hydrogen; methyl, ethyl, n-propyl, isopropyl, cyanomethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, methylsulfonylethyl, ethylsulfonylethyl; R 2 is selected from the group consisting of pyrazole, phenyl and pyridine, each of which may be substituted with one or two substituents independently selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxy, -CN, -COOH, -CONH2, -NO2, -NH2, -SF5, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, cyclobutyl, 1-cyanocyclopropyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, 1-cyano-1-methyleth-1-yl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, cyanomethoxy, methylthio, methylsulfinyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, (CH3)3-silyl, phenylsulfonyl (which may have fluorine, chlorine or methyl substituents); R 3 is hydrogen, methyl, ethyl, n-propyl or isopropyl; R 4is selected from the group consisting of pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrazin-3-yl, and 1,3-thiazol-2-yl, 1,3-oxazol-2-yl, 1,2-oxazol-3-yl, 1,2-thiazol-3-yl, 1H-pyrazol-1-yl, 1H-pyrazol-3-yl, 1H-imidazol-4-yl, each of which is selected from the group consisting of fluorine, chlorine, bromine, —CN, —COOH, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, cyanomethoxy, methylthio, methylsulfinyl, Methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, -COOCH3, -COOCH2CH3, and structure S13, wherein the bond to the pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrazin-3-yl, and 1,3-thiazol-2-yl, 1,3-oxazol-2-yl, 1,2-oxazol-3-yl, 1,2-thiazol-3-yl, 1H-pyrazol-1-yl, 1H-pyrazol-3-yl, 1H-imidazol-4-yl groups is marked with a #, and Z is CO; [ka]

[0043] R 41 is hydrogen, methyl, ethyl, n-propyl, propan-2-yl, butan-2-yl, 2,2,2-trifluoroethyl, 2-trifluoromethoxyethyl, cyanomethyl, cyclopropyl, cyclopropylmethyl or 2-methyl-n-propyl; R 42is hydrogen, methyl, ethyl, n-propyl, propan-2-yl, butan-2-yl, 2,2,2-trifluoroethyl, 2-trifluoromethoxyethyl, cyanomethyl, cyclopropyl, cyclopropylmethyl or 2-methyl-n-propyl; R 41 and R 42 together with the nitrogen atom to which they are attached, represent pyrrolidine, piperidine, azepane, morpholine, oxazepane, azacilloridine, azasilinane, and azacilepane (each of which may be substituted with one or two methyl groups); ; R 5 is hydrogen, fluorine, chlorine, bromine, iodine, —CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or cyanomethoxy; R 6 is hydrogen, fluorine, chlorine, bromine, iodine, —CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or cyanomethoxy. and salts and N-oxides thereof.

[0044] In a further embodiment (embodiment 4.2), the present invention provides a compound of formula (I) as described above, wherein: R 1 is hydrogen; methyl, ethyl, n-propyl, isopropyl, cyanomethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, methylsulfonylethyl, ethylsulfonylethyl; R 2is selected from the group consisting of phenyl and pyridine, wherein these are respectively fluorine, chlorine, bromine, iodine, hydroxy, -CN, -COOH, -CONH2, -NO2, -NH2, -SF5, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, cyclobutyl, 1-cyanocyclopropyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, 1-cyano-1-methyleth-1-yl (also referred to as 1-methyl-1-cyanoethyl), methoxy, ethoxy, difluoromethyl, ... optionally substituted with one or two substituents independently selected from the group consisting of cyclomethoxy, trifluoromethoxy, cyanomethoxy, methylthio, methylsulfinyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, (CH3)3-silyl, phenylsulfonyl (which may have fluorine, chlorine or methyl substituents); R 3 is hydrogen, methyl, ethyl, n-propyl or isopropyl; R 4is selected from the group consisting of pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrazin-3-yl, and 1,3-thiazol-2-yl, 1,3-oxazol-2-yl, 1,2-oxazol-3-yl, 1,2-thiazol-3-yl, 1H-pyrazol-1-yl, 1H-pyrazol-3-yl, 1H-imidazol-4-yl, each of which is selected from the group consisting of fluorine, chlorine, bromine, —CN, —COOH, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, cyanomethoxy, methylthio, methylsulfinyl, Methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, -COOCH3, -COOCH2CH3, and structure S13, wherein the bond to the pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrazin-3-yl, and 1,3-thiazol-2-yl, 1,3-oxazol-2-yl, 1,2-oxazol-3-yl, 1,2-thiazol-3-yl, 1H-pyrazol-1-yl, 1H-pyrazol-3-yl, 1H-imidazol-4-yl groups is marked with a #, and Z is CO; [ka]

[0045] R 41 is hydrogen, methyl, ethyl, n-propyl, propan-2-yl, butan-2-yl, 2,2,2-trifluoroethyl, 2-trifluoromethoxyethyl, cyanomethyl, cyclopropyl, cyclopropylmethyl or 2-methyl-n-propyl; R 42is hydrogen, methyl, ethyl, n-propyl, propan-2-yl, butan-2-yl, 2,2,2-trifluoroethyl, 2-trifluoromethoxyethyl, cyanomethyl, cyclopropyl, cyclopropylmethyl or 2-methyl-n-propyl; R 41 and R 42 together with the nitrogen atom to which they are attached, represent pyrrolidine, piperidine, azepane, morpholine, oxazepane, azacilloridine, azasirinane, or azacilepane (each of which may be substituted with one or two methyl groups). and optionally substituted with one substituent selected from the group consisting of: R 5 is hydrogen, fluorine, chlorine, bromine, iodine, —CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or cyanomethoxy; R 6 is hydrogen, fluorine, chlorine, bromine, iodine, —CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or cyanomethoxy. and salts and N-oxides thereof.

[0046] In a further embodiment (embodiment 4.3), the present invention provides a compound of formula (I) as described above, wherein: R 1 is hydrogen; methyl, ethyl, n-propyl, isopropyl, cyanomethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, methylthiomethyl, ethylthiomethyl; R 2is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine and pyridazine, wherein each of these is selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxy, CN, -COOH, -CONH2, -NO2, -NH2, SF5, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, cyanomethoxy, isopropan-2-ol, methylthio, methylsulfonyl ... phenylsulfonyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, (CH3)3-silyl, -SO2NH2, phenylsulfonyl (which may have fluorine, chlorine or methyl substituents), and oxetane, tetrahydropyran and piperazine (each of which may have methyl substituents); R 3 is hydrogen, methyl, ethyl, n-propyl or isopropyl; R 4is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine and thiazole, wherein each of these is selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxy, CN, -COOH, -CONH2, -NO2, -NH2, SF5, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, cyanomethoxy, isopropan-2-ol, methylthio, methylsulfonyl ... optionally substituted with one, two, or three substituents independently selected from the group consisting of phenyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, -NH(CH), -N(CH), -NHCO-CH, NHCO-cyclopropyl, -CON(CH)(CH-cyclopropyl), -SONH, and phenylsulfonyl, which may have fluorine, chlorine, methyl, or cyanomethyl substituents; R 5 is hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or cyanomethoxy; R 6 is hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or cyanomethoxy. and salts and N-oxides thereof.

[0047] In a further embodiment (embodiment 5.1), the present invention provides a compound of formula (I) as described above, wherein: R 1 is hydrogen or cyclopropylmethyl; R 2 is selected from the group consisting of pyrazole, phenyl and pyridine, each of which is optionally substituted with one or two substituents independently selected from the group consisting of fluorine, chlorine, bromine, iodine, —CN, —SF5, methyl, ethyl, n-propyl, isopropyl, tert-butyl, 1-cyano-1-methyleth-1-yl, cyclopropyl, 1-cyanocyclopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, 4-fluorophenylsulfonyl, difluoromethylsulfonyl; R 3 is methyl; R 4 is selected from the group consisting of pyridin-2-yl, pyrimidin-2-yl, 1,3-thiazol-2-yl, and 1H-pyrazol-1-yl, each of which is selected from fluorine, chlorine, bromine, -CN, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, -COOH, -COOCH3, -COOCH2CH3, and structure S13, wherein the bond marked with # is attached to the C-5 position of said pyridin-2-yl, pyrimidin-2-yl, or 1,3-thiazol-2-yl or the C-4 position of said 1H-pyrazol-1-yl; and Z is CO; [ka]

[0048] R 41 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl, cyclopropyl; R 42is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl; R 41 and R 42 together with the nitrogen atom to which they are attached represent pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane or (Si,Si-dimethyl)azasilinane; R 5 is hydrogen or methyl; R 6 is hydrogen or methyl. and salts and N-oxides thereof.

[0049] In a further embodiment (embodiment 5.2), the present invention provides a compound of formula (I) as described above, wherein: R 1 is hydrogen or cyclopropylmethyl; R 2 is selected from the group consisting of phenyl and pyridine, each of which is optionally substituted with one or two substituents independently selected from the group consisting of fluorine, chlorine, bromine, iodine, -CN, -SF5, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, and trifluoromethylsulfonyl; R 3 is methyl; R 4is selected from the group consisting of pyridin-2-yl, pyrimidin-2-yl, 1,3-thiazol-2-yl, and 1H-pyrazol-1-yl, each of which is selected from fluorine, chlorine, bromine, -CN, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, -COOH, -COOCH3, -COOCH2CH3, and structure S13, wherein the bond marked with # is attached to the C-5 position of said pyridin-2-yl, pyrimidin-2-yl, or 1,3-thiazol-2-yl or the C-4 position of said 1H-pyrazol-1-yl; and Z is CO; [ka]

[0050] R 41 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl; R 42 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl; R 41 and R 42 together with the nitrogen atom to which they are attached, represent pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane, (Si,Si-dimethyl)azasilinane] and optionally substituted with one substituent selected from the group consisting of: R 5 is hydrogen or methyl; R 6 is hydrogen or methyl. and salts and N-oxides thereof.

[0051] In a further embodiment (embodiment 5.3), the present invention provides a compound of formula (I) as described above, wherein: R 1 is hydrogen, methyl, cyclopropylmethyl, ethoxymethyl or ethylthiomethyl; R2 is selected from the group consisting of phenyl and pyridine, each of which is optionally substituted with one, two, or three substituents independently selected from the group consisting of fluorine, chlorine, bromine, CN, SF, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, trifluoromethyl, cyanomethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, cyanomethoxy, isopropan-2-ol, (CH)-silyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, —SONH, phenylsulfonyl (which may have fluorine substituents), and oxetane, tetrahydropyran, and piperazine (which may each have methyl substituents); R 3 is methyl; R 4 is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine and thiazole, each of which may be substituted with one or two substituents independently selected from the group consisting of fluorine, chlorine, bromine, CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, trifluoromethyl, cyanomethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, cyanomethoxy, isopropan-2-ol, -NHCO-CH3, NHCO-cyclopropyl, -CON(CH3)(CH3-cyclopropyl) and methylsulfonyl; R 5 is hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy; R 6is hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy. and salts and N-oxides thereof.

[0052] In a further embodiment (embodiment 6), the present invention provides a compound of formula (I) described above, wherein R 2 is phenyl which may be substituted as defined above, and the remaining substituents may have the meanings defined above, as well as salts and N-oxides thereof.

[0053] In a preferred embodiment of the above aspect 6 of the present invention, R 2 can be obtained by the following structure Q1, where the bond to the C=O-group is marked with a #: [ka]

[0054] where: R 25is hydroxy, -NH2, -SO2NH2, C4-C6 alkyl, C4 alkoxy, 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 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-C 4 alkyl, -N(C1-C4 alkyl)CO-C3-C6 cycloalkyl, -N(C1-C4 alkyl)S02C1-C4 alkyl, -N(S02C1-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-C4 alkyl)3-silyl, -SONH(C1-C4 alkyl), phenylsulfonyl or 3-6 membered heterocyclyl (containing 1 or 2 heteroatoms selected from the group consisting of N, O and S); wherein the phenyl group of the substituent and the 3- to 6-membered heterocyclyl substituent may have one, two, or three substituents independently selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C3 cyanoalkyl; and R 26is halogen, -CN, -COOH, -CONH2, -NO2, -SF5, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 haloalkylthio, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, C3-C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C3-C6 cycloalkyl, C1-C3 cyanoalkyl, C3-C6 cyanocycloalkyl] is.

[0055] R 25 and R 26 is preferably defined as follows: R 25 is -SO2NH2, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, (CH3)3-silyl, cyanomethoxy, tert-butyl, cyclopropyl, cyanomethyl, 1-cyano-1-methyleth-1-yl, 1-cyanocyclopropyl, isopropan-2-ol, phenylsulfonyl (which may have fluorine substituents); or oxetane, tetrahydropyran, or piperazine (each of which may have a methyl substituent); R 26 is fluorine, chlorine, bromine, CN, SF5, methyl, ethyl, n-propyl, isopropyl, butyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, cyclopropyl.

[0056] According to a further embodiment, R 25 and R 26 is preferably defined as follows: R 25is -SO2NH2, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, (CH3)3-silyl, cyanomethoxy, tert-butyl, cyclopropyl, cyanomethyl, isopropan-2-ol, phenylsulfonyl (which may have fluorine substituents); or is oxetane, tetrahydropyran, or piperazine (each of which may have a methyl substituent); R 26 is fluorine, chlorine, bromine, CN, SF5, methyl, ethyl, n-propyl, isopropyl, butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, cyclopropyl.

[0057] R 25 and R 26 is particularly preferably defined as follows: R 25 is methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, tert-butyl, cyclopropyl, 1-cyano-1-methyleth-1-yl, 1-cyanocyclopropyl, 4-fluorophenylsulfonyl; and R 26 is fluorine, chlorine, bromine, iodine, CN, SF5, methyl, ethyl, isopropyl, tert.-butyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, cyclopropyl.

[0058] According to a further embodiment, R 25 and R 26 is particularly preferably defined as follows: R 25is methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, tert-butyl, cyclopropyl; and R 26 is fluorine, chlorine, bromine, CN, SF5, methyl, ethyl, isopropyl, tert.-butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, cyclopropyl.

[0059] In a further embodiment of the above aspect 6 of the present invention, R 2 can be obtained by the following structure Q2, where the bond to the C=O-group is marked with a #: [ka]

[0060] where: R 27 is halogen, —CN, —COOH, —CONH 2 , —NO 2 , —SF 5 , C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 haloalkylthio; and R 28 is halogen, -CN, -COOH, -CONH2, -NO2, -SF5, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 haloalkylthio] is.

[0061] R 27 and R 28 is preferably defined as follows: R 27 is fluorine, chlorine, bromine, -CN, -SF5, methyl, ethyl, n-propyl, isopropyl, butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy; R 28is fluorine, chlorine, bromine, -CN, -SF5, methyl, ethyl, n-propyl, isopropyl, butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy.

[0062] In a further embodiment (embodiment 7), the present invention provides a compound of formula (I) described above, wherein R 2 is thiophene, pyrazole or imidazole, each of which may be substituted as defined above, and the remaining substituents may have the meanings defined above, as well as salts and N-oxides thereof.

[0063] In a preferred embodiment of the above aspect 7 of the present invention, R 2 is selected from optionally substituted thiophene and pyrazole groups: [ka]

[0064] where: R 9 is selected from halogen (preferably fluorine, chlorine and bromine), C1-C3 alkyl (preferably methyl), C1-C3 haloalkyl (preferably trifluoromethyl) and pentafluorosulfanyl; n is an integer of 0, 1 or 2 (preferably 1 or 2); and Y represents hydrogen, C1-C3 alkyl (preferably methyl and ethyl), cycloalkyl (preferably cyclopropyl), C1-C3 haloalkyl (preferably trifluoromethyl).

[0065] Such a group R 2 A preferred example is represented by the formula: [ka]

[0066] In a further embodiment (embodiment 8), the present invention provides a compound of formula (I) described above, wherein R4 is selected from the group consisting of pyridine, pyrimidine, thiazole, pyrazole and pyrazine, each of which may be substituted as defined above, and the remaining substituents may have the meanings defined above, as well as salts and N-oxides thereof.

[0067] In a preferred embodiment of the above aspect 8 of the present invention, R 4 is selected from the group consisting of pyridine, pyrimidine and thiazole, each of which may be substituted as defined above, and the remaining substituents may have the meanings defined above, as well as salts and N-oxides thereof.

[0068] In a preferred embodiment of the above aspect 8 of the present invention, the compound of formula (I) is characterized in that it has a structure of formula (Ii), formula (I-ii) or formula (I-iii): [ka]

[0069] In the above formula, R 1 , R 2 , R 3 , R 5 and R 6 has the meaning defined in any of the embodiments described above; and R 8 is R 4 represents 0, 1, 2, 3 or 4 identical or different substituents as defined in any of the embodiments described above with respect to R 8 represents 0, 1 or 2 substituents, more preferably 0 or 1 substituent; and its salts and N-oxides.

[0070] In a further preferred embodiment of the above aspect 8 of the present invention, the compound of formula (I) is characterized by having the structure of formula (Ii) above, and R 1 , R2 , R 3 , R 5 , R 6 has the meaning defined in any of the embodiments described above, and R 8 represents 0, 1 or 2 (preferably 0 or 1) identical or different substituents selected from fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, CONHcyclopropyl, CO-N-morpholinyl, CON(CH(cyclopropylmethyl), CO-N-pyrrolidinyl, CON(CH(CHCN)); and salts and N-oxides thereof.

[0071] In a further preferred embodiment of the above aspect 8 of the present invention, the compound of formula (I) is characterized by having the structure of formula (Ii) above, and R 1 , R 2 , R 3 , R 5 , R 6 has the meaning defined in any of the embodiments described above, and R 8 is -CN, -COOH, -COOCH3, -COOCH2CH3, and structure S13, wherein the bond marked with # is attached to the pyridine, preferably at the C-5 position, and Z is CO; [ka]

[0072] R 41 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl or cyclopropyl; R 42 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl; R 41 and R 42represent 0, 1 or 2 (preferably 0 or 1) identical or different substituents selected from the group consisting of: pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane, (Si,Si-dimethyl)azasilinane, together with the nitrogen atom to which they are attached; and salts and N-oxides thereof.

[0073] In a further preferred embodiment of the above aspect 8 of the present invention, the compound of formula (I) is characterized by having a structure represented by formula (I-ii) above, and R 1 , R 2 , R 3 , R 5 , R 6 has the meaning defined in any of the above-described embodiments, and R 8 represents 0, 1 or 2 (preferably 0 or 1) identical or different substituents selected from fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, CONHcyclopropyl, CO-N-morpholinyl, CON(CH(cyclopropylmethyl), CO-N-pyrrolidinyl, CON(CH(CHCN)); and salts and N-oxides thereof.

[0074] In a further preferred embodiment of the above aspect 8 of the present invention, the compound of formula (I) is characterized by having a structure represented by formula (I-ii) above, and R 1 , R 2 , R 3 , R 5 , R 6 has the meaning defined in any of the embodiments described above, and R 8 is -CN, -COOH, -COOCH3, -COOCH2CH3, and structure S13, wherein the bond marked with a # is attached to the pyrimidine, preferably at the C-5 position, and Z is CO; [ka]

[0075] R 41is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl or cyclopropyl; R 42 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl; R 41 and R 42 represent 0, 1 or 2 (preferably 0 or 1) identical or different substituents selected from the group consisting of: pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane, (Si,Si-dimethyl)azasilinane, together with the nitrogen atom to which they are attached; and salts and N-oxides thereof.

[0076] In a further preferred embodiment of the above aspect 8 of the present invention, the compound of formula (I) is characterized by having a structure represented by formula (I-iii) above, and R 1 , R 2 , R 3 , R 5 , R 6 has the meaning defined in any of the above-described embodiments, and R 8 represents 0, 1 or 2 (preferably 0 or 1) identical or different substituents selected from fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, CONHcyclopropyl, CO-N-morpholinyl, CON(CH(cyclopropylmethyl), CO-N-pyrrolidinyl, CON(CH(CHCN)); and salts and N-oxides thereof.

[0077] In a further preferred embodiment of the above aspect 8 of the present invention, the compound of formula (I) is characterized by having a structure represented by formula (I-iii) above, and R 1 , R 2 , R 3 , R 5 , R 6 has the meaning defined in any of the embodiments described above, and R8 is fluorine, chlorine, bromine, -CN, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, -COOH, -COOCH3, -COOCH2CH3, and structure S13, wherein the bond marked with # is attached to the thiazole, preferably at the C-5 position, and Z is CO; [ka]

[0078] R 41 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl or cyclopropyl; R 42 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl; R 41 and R 42 represent 0, 1 or 2 (preferably 0 or 1) identical or different substituents selected from the group consisting of: pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane, (Si,Si-dimethyl)azasilinane, together with the nitrogen atom to which they are attached; and salts and N-oxides thereof.

[0079] In a further preferred embodiment of the above aspect 8 of the present invention, the compound of formula (I) is characterized in that it has a structure of formula (I-iv): [ka]

[0080] In the above formula, R 1 , R 2 , R 3 , R 5 and R 6 has the meaning defined in any of the embodiments described above; and R8 is R 4 represents 0, 1, 2, 3 or 4 identical or different substituents as defined in any of the embodiments described above with respect to R 8 represents 0, 1 or 2 substituents, more preferably 0 or 1 substituent; and its salts and N-oxides.

[0081] In a further preferred embodiment of the above aspect 8 of the present invention, the compound of formula (I) is characterized by having a structure represented by formula (I-iv) above, and R 1 , R 2 , R 3 , R 5 , R 6 has the meaning defined in any of the above-described embodiments, and R 8 represents 0, 1 or 2 (preferably 0 or 1) identical or different substituents selected from fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, CONHcyclopropyl, CO-N-morpholinyl, CON(CH(cyclopropylmethyl), CO-N-pyrrolidinyl, CON(CH(CHCN)); and salts and N-oxides thereof.

[0082] In a further preferred embodiment of the above aspect 8 of the present invention, the compound of formula (I) is characterized by having a structure represented by formula (I-iv) above, and R 1 , R 2 , R 3 , R 5 , R 6 has the meaning defined in any of the embodiments described above, and R 8 is fluorine, chlorine, bromine, -CN, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, -COOH, -COOCH3, -COOCH2CH3, and structure S13, wherein the bond marked with # is attached to the thiazole, preferably at the C-5 position, and Z is CO; [ka]

[0083] R 41 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl, cyclopropyl; R 42 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl; R 41 and R 42 represent 0, 1 or 2 (preferably 0 or 1) identical or different substituents selected from the group consisting of: pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane, (Si,Si-dimethyl)azasilinane, together with the nitrogen atom to which they are attached; and salts and N-oxides thereof.

[0084] In a further aspect (Aspect 9), the present invention relates to a compound of formula (I) as described in any of the above aspects, wherein the compound has a structure of formula (Iv), (I-vi), or (I-vii): [ka]

[0085] In the above formula, R 1 , R 3 , R 5 and R 6 has the meaning defined in any of the embodiments set forth above; R 7 R is defined in any of the above-described embodiments. 2 represents the same or different substituents of R 8 R is defined in any of the above-described embodiments. 4 represents the same or different substituents of n represents an integer of 0, 1, or 2 (preferably, 0 or 1); m represents an integer of 0, 1 or 2 (preferably 1 or 2); and its salts and N-oxides.

[0086] According to a preferred embodiment of aspect 9, the present invention is directed to compounds of formula (Iv) as defined above.

[0087] According to a further preferred embodiment of aspect 9, the present invention is directed to compounds of formula (I-vi) as defined above.

[0088] According to a preferred embodiment of aspect 9, the present invention is directed to compounds of formula (I-vii) as defined above.

[0089] In a further aspect (Aspect 10), the present invention relates to a compound of Formula (I) as described in any of the preceding aspects, wherein the compound has a structure according to one of Formulas (I-viii), (I-ix), (Ix), (I-xi), and (I-xii): [ka]

[0090] In the above formula, R 1 , R 3 , R 5 and R 6 has the meaning defined in any of the embodiments set forth above; R 7 R is defined in any of the above-described embodiments. 2 represents the same or different substituents of R 8 R is defined in any of the above-described embodiments. 4 represents the same or different substituents of n represents an integer of 0, 1, or 2 (preferably, 0 or 1); m represents an integer of 0, 1 or 2 (preferably 1 or 2); and its salts and N-oxides.

[0091] According to a preferred embodiment of aspect 10, the present invention is directed to compounds of formula (I-viii) as defined above.

[0092] According to a further preferred embodiment of aspect 10, the present invention is directed to compounds of formula (I-ix) as defined above.

[0093] According to a preferred embodiment of aspect 10, the present invention is directed to compounds of formula (Ix) as defined above.

[0094] According to a preferred embodiment of aspect 10, the present invention is directed to compounds of formula (I-xi) as defined above.

[0095] According to a preferred embodiment of aspect 10, the present invention provides a compound of formula (I-xii), (I-xiii), (I-xiv), (I-xv), (I-xvi), (I-xvii), (I-xviii) or (I-xix) [ka]

[0096] TIFF0007778687000028.tif51131

[0097] [During the ceremony, R 1 , R 3 , R 5 and R 6 has the meaning defined in any of the embodiments set forth above; R 7 R is defined in any of the above-described embodiments. 2 represents the same or different substituents of R 8R is defined in any of the above-described embodiments. 4 represents the same or different substituents of R 81 represents C-C alkyl, C-C alkenyl, C-C alkynyl, C-C cycloalkyl, C-C haloalkyl, hydroxy-C-C alkyl, -COC-C alkyl, -C(=NOC-C alkyl)H, -C(=NOC-C alkyl)-C-C alkyl, in each case optionally substituted, wherein said optionally substituted radicals are optionally substituted with up to three substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO, -Si(CH), -NH, C-C alkyl, C-C haloalkyl, C-C cycloalkyl, C-C halocycloalkyl, C-C alkoxy, C-C haloalkoxy, C-C alkylsulfonyl, C-C cycloalkylsulfonyl, C-C haloalkylthio and C-C haloalkylsulfonyl; or a 3- to 6-membered heterocyclyl containing one or two heteroatoms selected from the group consisting of N, O, and S, wherein the 3- to 6-membered heterocyclyl 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 haloalkyl, C1-C3 cyanocycloalkyl; 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; R 81preferably represents C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C4 cyanocycloalkyl, hydroxy-C2-C3 alkyl, -CO2C1-C3 alkyl, -NH(C1-C3 alkyl), -N(C1-C3 alkyl)2, -C(=NOC1-C3 alkyl)H or -C(=NOC1-C3 alkyl)-C1-C3 alkyl; R 81 more preferably represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, difluoroethyl, trifluoroethyl, cyanomethyl, cyanoethyl, 2-hydroxyethyl, -COOCH3 or -COOCH2CH3; R 81 particularly preferably denotes methyl or ethyl; m represents an integer of 0, 1 or 2 (preferably 1 or 2). and salts and N-oxides thereof.

[0098] According to a preferred embodiment of aspect 10, the present invention is directed to compounds of formula (I-xii) as defined above.

[0099] According to a further preferred embodiment of aspect 10, the present invention is directed to compounds of formula (I-xiii) as defined above.

[0100] According to a preferred embodiment of aspect 10, the present invention is directed to compounds of formula (I-xiv) as defined above.

[0101] According to a preferred embodiment of aspect 10, the present invention is directed to compounds of formula (I-xv) as defined above.

[0102] According to a further preferred embodiment of aspect 10, the present invention is directed to compounds of formula (I-xvi) as defined above.

[0103] According to a preferred embodiment of aspect 10, the present invention is directed to compounds of formula (I-xvii) as defined above.

[0104] According to a preferred embodiment of aspect 10, the present invention is directed to compounds of formula (I-xviii) as defined above.

[0105] According to a preferred embodiment of aspect 10, the present invention is directed to compounds of formula (I-xix) as defined above.

[0106] According to one embodiment, the present invention provides a compound of formula (I), wherein R 5 represents hydrogen, and the remaining substituents can have any of the meanings described herein.

[0107] According to one embodiment, the present invention provides a compound of formula (I), wherein R 6 does not represent hydrogen, and the remaining substituents can have any of the meanings described herein.

[0108] A further (embodiment 11) of the present invention is a compound represented by formula (IX-1), formula (X) or formula (XIII) 3 , R 4 , R 5 and R 6 has the meaning defined in any of the above aspects of the invention. [ka]

[0109] Particularly preferred are the compounds described in the Examples below.

[0110] 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.

[0111] For all structures described herein including ring systems and groups, adjacent atoms must not be -OO- or -OS-.

[0112] 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).

[0113] 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 "C LL -C UL " or "LL~UL member" can be added to make it more specific.

[0114] In the definitions of the symbols given in the formula above, collective terms have been used which generally represent the following substituents:

[0115] 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.

[0116] Examples of heteroatoms are N, O, S, P, B, Si. Preferably, the term "heteroatom" relates to N, S and O.

[0117] 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.

[0118] 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.

[0119] 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.

[0120] 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.

[0121] 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.

[0122] 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.

[0123] According to the present invention, "hydroxyalkyl" denotes straight-chain or branched alcohols, preferably having 1 to 6 carbon atoms, such as methanol, ethanol, n-propanol, isopropanol (isopropan-2-ol), 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.

[0124] 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.

[0125] According to the present invention, "cycloalkoxy" denotes an -O-cycloalkyl group, where cycloalkyl has the meaning defined above. Preferred are cycloalkyls having 3, 4, 5, 6 or 7 carbon atoms, i.e., especially -O-cyclopropyl, -O-cyclobutyl, -O-cyclopentyl, -O-cyclohexyl, -O-cycloheptyl. The cycloalkoxy groups of the present invention can be substituted with one or more identical or different radicals, preferably any substituents selected from halogen.

[0126] 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.

[0127] 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 may be substituted with one or more identical or different radicals.

[0128] 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.

[0129] According to the present invention, "cycloalkylsulfonyl" denotes a monocyclic, bicyclic or tricyclic cycloalkylsulfonyl, preferably having 4 to 10 or 4 to 7 carbon atoms, such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl and cyclohexylsulfonyl. Preference is furthermore given to cycloalkylsulfonyl having 4, 5 or 7 carbon atoms, such as, in particular, cyclopropylsulfonyl or cyclobutylsulfonyl. Cycloalkylsulfonyl according to the present invention can be substituted with one or more identical or different radicals.

[0130] As used herein, the term "alkylcarbonyl" refers to a straight or branched alkyl-C(=O) group, preferably having 2 to 7 carbon atoms, such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl, and t-butylcarbonyl. Alkylcarbonyl groups having 1 to 4 carbon atoms are also preferred. The alkylcarbonyl group can be substituted with one or more identical or different radicals.

[0131] As used herein, the term "alkoxycarbonyl," alone or as a component of a chemical group, refers to straight-chain or branched-chain alkoxycarbonyl, preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkoxy portion, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl, and t-butoxycarbonyl. The alkoxycarbonyl group can be substituted with one or more identical or different radicals.

[0132] As used herein, the term "alkylaminocarbonyl" refers to a straight-chain or branched alkylaminocarbonyl group, preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl portion, such as methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, s-butylaminocarbonyl, and t-butylaminocarbonyl. The alkylaminocarbonyl group can be substituted with one or more identical or different radicals.

[0133] As used herein, the term "N,N-dialkylaminocarbonyl" refers to a straight-chain or branched N,N-dialkylaminocarbonyl group, preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl portion, 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 can be substituted with one or more identical or different radicals.

[0134] In general, the term "aryl" refers to a monocyclic, bicyclic, or polycyclic aromatic system, preferably having 6 to 14, especially 6 to 10, ring carbon atoms, such as phenyl, naphthyl, anthryl, or phenanthrenyl, and preferably phenyl. Aryl also refers to polycyclic systems (including fused polycyclic systems) in which the bonding site is on the aromatic system, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, or biphenyl. A fused polycyclic system has at least two fused rings, where these two fused rings share two adjacent atoms (or, in other words, the rings share one covalent bond). Phenyl is preferred. The aryl group (especially the phenyl group) according to the present invention can be substituted with one or more identical or different radicals.

[0135] 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.

[0136] 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 contains 3 to 12 ring atoms (preferably 3 to 9 ring atoms, particularly 3 to 6 ring atoms) and one or more (preferably 1 to 4, particularly 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. A heterocyclic ring typically contains up to four nitrogen atoms and / or up to two oxygen atoms and / or up to two sulfur atoms. Non-aromatic heterocycles herein are generally referred to as "saturated or unsaturated heterocycles." When a heterocyclyl radical or heterocyclic ring is optionally substituted, the heterocyclyl radical or heterocyclic ring may be fused to another carbocyclic or heterocyclic ring. In the case of optionally substituted heterocyclyls, the present invention also encompasses polycyclic systems such as 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. In the case of optionally substituted heterocyclyls, the present invention also encompasses spirocyclic systems such as 1-oxa-5-azaspiro[2.3]hexyl.

[0137] Preferred heterocyclyl groups of the invention are, 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. Most preferred are oxetanyl, tetrahydropyranyl, and piperazinyl.

[0138] 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. For clarity, when the definition of a substituent herein includes "heterocycle" (or "heterocyclyl") and "heteroaryl" (or "heteroaromatic"), this means that the term "heterocycle" (or "heterocyclyl") does not encompass "heteroaryl" (or "heteroaromatic") groups, in order to avoid overlapping definitions. Preferred are 5- to 7-membered rings (more preferably 6- to 6-membered rings) having 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. Preferred are pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyrazolyl, pyrrolyl, thiazolyl, oxazolyl, isothiazolyl and isoxazolyl. More preferred are pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyrazolyl, pyrrolyl and thiazolyl. Heteroaryl groups according to the present invention may also be substituted with one or more identical or different radicals.

[0139] 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, may be substituted, for example, meaning substituted radicals derived from an unsubstituted base structure, where the substituents (e.g., one substituent or multiple substituents, preferably 1, 2, 3, 4, 5, 6 or 7 substituents, more preferably 1, 2, 3 or 4 substituents, even more preferably 1, 2 or 3 substituents, even more preferably 1 or 2 substituents) are selected from the group consisting of amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, methyl ... , 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 ((C1-C4 alkyl)3-silyl), 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 may 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 (the "first substituent level"), when they contain a hydrocarbonaceous moiety, may have further substituents therein (the "second substituent level"), such as one or more substituents each independently selected from halogen, hydroxyl, C1-C6 alkyl, amino, nitro, cyano, isocyano, azido, acylamino, oxo, and imino. The term "optionally substituted" groups preferably includes only one or two substitution levels.

[0140] The halogen-substituted or halogenated chemical group according to the present invention (e.g., alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfinyl, or alkylsulfonyl) is mono-substituted 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, halocycloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, or haloalkylsulfonyl). 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. Halogen is, in particular, fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine, and even 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 are haloalkyls having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms selected from fluorine and chlorine (e.g., especially difluoromethyl, trifluoromethyl, or 2,2-difluoroethyl). Further examples of halogen-substituted compounds include 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, and the like. sulfinyl, 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.

[0141] Cyano-substituted chemical groups (e.g., alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfinyl, or alkylsulfonyl) according to the present invention are preferably mono-substituted with cyano. Such cyano-substituted groups are also referred to as cyano groups (e.g., cyanoalkyl, cyanocycloalkyl, cyanoalkoxy, cyanoalkylthio, cyanoalkylsulfinyl, cyanoalkylsulfonyl, etc.). When the number of carbon atoms in such cyano groups is specified (e.g., C LL-UL cyanoalkyl), the carbon atoms of the cyano group are not counted; e.g., C 1-3 Cyanoalkyl includes cyanopropyl groups.

[0142] 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, chlorine, bromine and cyano.

[0143] 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.

[0144] Substituted amino also includes quaternary ammonium compounds (salts) having four organic substituents on the nitrogen atom.

[0145] Optionally substituted phenyl is preferably unsubstituted phenyl or one of the following selected from the group consisting of halogen, SF5, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, hydroxy-C1-C4-alkyl, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, cyano, isocyano and nitro. Phenyl which is mono- or polysubstituted (preferably up to three times) by selected identical or different radicals, such as o-tolyl, m-tolyl and p-tolyl, dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl and 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl and 4-fluorophenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl and 4-trifluoromethylphenyl, and 4-trichloromethylphenyl, 2,4-dichlorophenyl, 3,5-dichlorophenyl, 2,5-dichlorophenyl and 2,3-dichlorophenyl, o-methoxyphenyl, m-methoxyphenyl and p-methoxyphenyl, 4-heptafluorophenyl.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] The present invention further relates to the use of compounds of formula (I) as pesticides, in particular as crop protection agents.

[0151] In the context of this application, the term "pesticide" always also encompasses the term "crop protection agent".

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] Thus, the term "hygienic protection" includes all actions that maintain and / or improve such hygienic means, methods and practices.

[0157] 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: 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, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., e.g., Anoplophora glabripennis, Anthonomus spp., e.g., Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp. spp., for example, Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., for example, Bruchus pisorum, Bruchus rufimanus, Cassida spp.), Cerotoma trifurcata, Ceutorrhynchus spp., e.g., Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., e.g., Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp. 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, Cryptolestes pusillus, Cryptorhynchus lapati 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. spp.), Dicladistella armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., e.g., Epilachna borealis, Epilachna varivestis, Epitrix spp., e.g., Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp.), Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp. such as Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae oryzae, Lathridius spp., Lema spp., Leptinotarsa ​​decemlineata, Leucoptera spp. e.g. Leucoptera coffeella, Limonius ectypus, Lissorhoptrus oryzophilus, Listronotus spp. (= Hyperodes spp.), Lixus spp., Luperodes spp., Luperomorpha xanthodella xanthodera, Lyctus spp., Megacyllene spp., e.g., Megacyllene robiniae, Megascelis spp., Melanotus spp., e.g., Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp.), for example, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., for example, Otiorhynchus cribricollis cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp. such as Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp. such as Phyllophaga helleri, Phyllotreta spp. spp.), for example, Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp.), Prostephanus truncatus, Psylliodes spp. e.g. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ve. ntralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Scolytus spp., e.g., Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp., e.g., Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., for example, Sternechus paludatus, Symphyletes spp., Tanymecus spp., for example, Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp. spp.), e.g., Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.), e.g., 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., e.g., Helicoverpa armigera, Helicoverpa zea, Heliothis spp., e.g., Heliothis virescens, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp. spp.), Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., e.g., 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, Maruca testulalis, Mamestra brassicae, Melanitis leda leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., e.g. Ostrinia nubilalis, Panolis flammea, Parnara spp. 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.

[0158] 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.

[0159] formulation The present invention further relates to formulations, compositions and application forms comprising at least one compound of formula (I) as defined above. Such formulations and compositions are in particular prepared as pesticides (e.g., drench solutions, drip solutions and spray solutions) comprising at least one compound of formula (I). Such formulations may further comprise at least one further compound selected from adjuvants, excipients, solvents and / or additional pharmaceutically active agents. Optionally, the formulation or use form contains further pesticides and / or action-enhancing adjuvants, for example penetrating agents such as vegetable oils (e.g. rapeseed oil, sunflower oil), mineral oils (e.g. paraffin oil), vegetable fatty acid alkyl esters (e.g. rapeseed oil methyl ester or soybean oil methyl ester) or alkanol alkoxylates, and / or spreading agents such as alkylsiloxanes and / or salts, for example organic or inorganic ammonium or phosphonium salts (e.g. ammonium sulfate or diammonium hydrogen phosphate), and / or retention promoters (e.g. dioctyl sulfosuccinate or hydroxypropyl guar polymers), and / or wetting agents (e.g. glycerol), and / or fertilizers (e.g. ammonium-, potassium- or phosphorus-containing fertilizers).

[0160] Conventional formulations are, for example, water-soluble solutions (SL), emulsifiable concentrates (EC), oil-in-water emulsions (EW), suspension concentrates (SC, SE, FS, OD), water dispersible granules (WG), granules (GR), and capsule concentrates (CS); these and other possible formulations are described, for example, in Crop Life International and in Pesticide Specifications, Manual on the development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers -173 (produced by the FAO / WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576). In addition to one or more compounds of formula (I), the formulations may optionally contain further pesticidal active compounds.

[0161] These are preferably formulations or use forms that contain auxiliary substances such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, frost protectants, biocides, thickeners and / or other auxiliary substances (e.g., adjuvants). In this context, an adjuvant is a component that enhances the biological effect of the formulation, but does not itself have a biological effect. Examples of adjuvants are agents that promote retention, spreading, adhesion to the leaf surface or agents that promote penetration.

[0162] These formulations are prepared in known manner, for example by mixing a compound of formula (I) with auxiliaries (e.g., extenders, solvents and / or solid carriers, and / or further auxiliaries, e.g., surfactants). Such formulations are prepared in suitable equipment or prepared before or during application.

[0163] The adjuvants used may be substances suitable for imparting special properties, such as particular physical, technical and / or biological properties, to the formulation of the compound of formula (I) or to the use forms prepared from such formulations (e.g. ready-to-use pesticides, such as spray solutions or seed dressing products).

[0164] Suitable extenders are, for example, water and polar and non-polar organic chemical liquids, such as those selected from the following classes: aromatic and non-aromatic hydrocarbons (for example paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may, where appropriate, be substituted, etherified and / or esterified), ketones (for example acetone, cyclohexanone), esters (which include fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides, lactams (for example N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (for example dimethyl sulfoxide), carbonates and nitriles.

[0165] When the extender used is water, for example, organic solvent can also be used as auxiliary solvent.Suitable liquid solvents are essentially the following: aromatic compounds, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, such as mineral oil fractions, mineral oils and vegetable oils, alcohols, such as butanol or glycols and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents, such as dimethylformamide or dimethyl sulfoxide, carbonates, such as propylene carbonate, butylene carbonate, diethyl carbonate or dibutyl carbonate, or nitriles, such as acetonitrile or propanenitrile.

[0166] In principle, all suitable solvents can be used.Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane, paraffins, petroleum fractions, mineral oil and vegetable oil, alcohols, such as methanol, ethanol, isopropanol, butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents, such as dimethyl sulfoxide, carbonates, such as propylene carbonate, butylene carbonate, diethyl carbonate or dibutyl carbonate, nitriles, such as acetonitrile or propanenitrile, and also water.

[0167] In principle, any suitable carrier can be used. Useful carriers include, inter alia: ammonium salts and crushed natural minerals, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth; and crushed synthetic materials, such as finely divided silica, alumina, and natural or synthetic silicates, resins, waxes, and / or solid fertilizers. Mixtures of such carriers can also be used. Useful carriers for granules include, for example, crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, and dolomite, as well as synthetic granules made from inorganic and organic meal, and also granules made from organic materials (such as sawdust, paper, coconut shells, corn cobs, and tobacco stems).

[0168] It is also possible to use liquefied gas extenders or solvents. Particularly suitable extenders or carriers are those that are gaseous at ambient temperature and atmospheric pressure, such as aerosol propellant gases, such as halohydrocarbons, and also butane, propane, nitrogen and carbon dioxide.

[0169] Examples of emulsifiers and / or foam-forming agents, dispersants or wetting agents with ionic or non-ionic properties, or mixtures of these surfactants are: salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and fatty alcohols or fatty acids or fatty amines, polycondensates of ethylene oxide and substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), isethionate derivatives, phosphate esters of polyethoxylated alcohols or phosphate esters of polyethoxylated phenols, fatty esters of polyols, and derivatives of these compounds containing sulfate, sulfonate and phosphate anions, such as alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignosulfite waste liquors and methylcellulose. If one of the compounds of formula (I) and / or one of the inert carriers is water-insoluble and application is carried out in water, it is advantageous to have a surfactant present.

[0170] As further auxiliaries in the preparations and the use forms derived therefrom, it is possible to use colorants, for example inorganic pigments such as iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, as well as nutrients and micronutrients such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts.

[0171] Further components may be stabilizers (e.g., low-temperature stabilizers), preservatives, antioxidants, light stabilizers, or other agents that improve chemical and / or physical stability. Additionally, foam-forming or anti-foaming agents may also be present.

[0172] Additional adjuvants may also be present in the formulations and the use forms derived therefrom, such as adhesives, for example, carboxymethylcellulose, and natural and synthetic polymers, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, in the form of powders, granules or latex, or natural phospholipids, for example, cephalin and lecithin, and synthetic phospholipids. Further possible adjuvants are mineral oil and vegetable oil.

[0173] Optionally, further auxiliaries may be present in the formulation and the use forms derived therefrom. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrating agents, retention promoters, stabilizers, sequestering agents, complexing agents, wetting agents, spreading agents, etc. In general, the compound of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.

[0174] Useful retention aids include any material that reduces dynamic surface tension (eg, dioctyl sulfosuccinate) or increases viscoelasticity (eg, hydroxypropyl guar polymers).

[0175] In the context of the present invention, suitable penetrants are all substances commonly used to improve the penetration of pesticidal active compounds into plants. In this context, penetrants are defined by their ability to penetrate into the plant cuticle from the (usually aqueous) application solution and / or from the spray coating, thereby enhancing the mobility of the active compound within the cuticle. To confirm this property, the method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used. Examples include alcohol alkoxylates, such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters, such as rapeseed oil methyl ester or soybean oil methyl ester, fatty amine alkoxylates, such as tallow amine ethoxylate (15), or ammonium and / or phosphonium salts, such as ammonium sulfate or diammonium hydrogen phosphate.

[0176] The formulation preferably contains 0.00000001% to 98% by weight of the compound represented by formula (I), or particularly preferably 0.01% to 95% by weight of the compound represented by formula (I), and even more preferably 0.5% to 90% by weight of the compound represented by formula (I), based on the weight of the formulation.

[0177] The content of the compound of formula (I) in the use form prepared from the formulation (especially a pesticide) can vary within a wide range. The concentration of the compound of formula (I) in the use form is generally 0.00000001% to 95% by weight, preferably 0.00001% to 1% by weight, based on the weight of the use form. The compound is used in a conventional manner suitable for the use form.

[0178] 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.

[0179] 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).

[0180] 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.

[0181] 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.

[0182] 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.

[0183] (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.

[0184] (2) GABA-regulated chloride channel blockers, preferably cyclodiene-organochlorines, selected from chlordane and endosulfan; or Phenylpyrazoles (fiproles), which are selected from ethiprole and fipronil.

[0185] (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.

[0186] (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.

[0187] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, preferably Spinosyns, which are selected from spinetoram and spinosad.

[0188] (6) glutamate-gated chloride channel (GluCl) allosteric modulators, preferably Avermectins / milbemycins, which are selected from abamectin, emamectin benzoate, lepimectin and milbemectin.

[0189] (7) Juvenile hormone mimetics, preferably Juvenile hormone analogs, selected from hydroprene, kinoprene, and methoprene; or Fenoxycarb; or pyriproxyfen.

[0190] (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.

[0191] (9) Chordotonal organ TRPV channel modulators, which are selected from pymetrozine and pyrifluquinazone.

[0192] (10) Mite growth inhibitors, which are selected from clofentezine, hexythiazox, diflobidazine and etoxazole.

[0193] (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).

[0194] (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.

[0195] (13) An uncoupler of oxidative phosphorylation by disrupting the proton gradient, which is selected from chlorfenapyr, DNOC, and sulfluramide.

[0196] (14) Nicotinic acetylcholine receptor channel blockers, which are selected from bensultap, cartap hydrochloride, thiocylam and thiosultap-sodium.

[0197] (15) Chitin biosynthesis inhibitors (type 0), which are selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[0198] (16) Chitin biosynthesis inhibitors (type 1), which are selected from buprofezin.

[0199] (17) Molting disruptors (especially for Diptera, i.e., for dipterans), which are selected from cyromazines.

[0200] (18) Ecdysone receptor agonists, which are selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0201] (19) Octopamine receptor agonists, which are selected from amitraz.

[0202] (20) Mitochondrial complex III electron transport inhibitors, which are selected from hydramethylnon, acequinocyl, and fluacrypyrim.

[0203] (21) Mitochondrial complex I electron transport inhibitors, preferably METI acaricides, selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or Rotenone (Derris).

[0204] (22) Voltage-gated sodium channel blockers, which are selected from indoxacarb and metaflumizone.

[0205] (23) Acetyl-CoA carboxylase inhibitors, preferably Tetronic acid derivatives and tetramic acid derivatives, which are selected from spirodiclofen, spiromesifen and spirotetramat.

[0206] (24) Mitochondrial complex IV electron transport inhibitors, preferably phosphine-based, selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or The cyanide is selected from calcium cyanide, potassium cyanide and sodium cyanide.

[0207] (25) Mitochondrial complex II electron transport inhibitors, preferably β-ketonitrile derivatives, which are selected from cyenopyrafen and cyflumetofen; and Carboxanilides, which are selected from piflubumid.

[0208] (28) Ryanodine receptor modulators, preferably Diamides, selected from chlorantraniliprole, cyantraniliprole and flubendiamide.

[0209] (29) Chordotonal organ modulators (target site not defined), which are selected from flonicamide.

[0210] (30) Additional active ingredients selected from the following: acinonapyr, afidopiropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, benzpyrimoxane, bifenazate, brofuranilide, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dichloromezothiaz, dicofol, dimpropyridaz, epsilon-metofluthrin, epsilon-momfluthrin, flometoquin, fluazaindolizine, fluensulfone, flufenerim, flufenoxis strobin, flufiprole, fluhexafon, fluopyram, flupirimine, fluralaner, fluxamethamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, isocycloceram, kappa-bifenthrin, kappa-tefluthrin, lotilaner, meperfluthrin, oxazosulfil, paichongding, pyridalyl, pyrifluquinazone, pyriminostrobin, spirobudiclofen, spiropidione, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tigolaner, thioxazaphen, thiofluoximate, iodomethane; Furthermore, preparations based on Bacillus firmus (I-1582, BioNeem, Votivo) and, furthermore, the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO 2006 / 043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003 / 106457) (CAS 637360-23-7), 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), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004 / 099160) (CAS 792914-58-0), 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-oxido-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-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propanamide (known from WO2015 / 058021A1 and WO2015 / 058028A1) (CAS 1477919-27-9), and 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), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (known from WO2013 / 115391A1) (CAS 1449021-97-9), 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), 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[(4R)-2-ethyl-3-oxo-4-isoxazolidinyl]-2-methyl-benzamide (known from WO2011 / 067272, WO2013 / 050302) (CAS 1309959-62-3).

[0211] 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).

[0212] 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.

[0213] (1) Inhibitors of ergosterol biosynthesis, for example, (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) mitomycin, Clobutanil, (1.015) Paclobutrazol, (1.016) Prochloraz, (1.017) Propiconazole, (1.018) Prothioconazole, (1.019) Pyrisoxazole, (1.020) Spiroxamine, (1.021) Tebuconazole, (1.022) Tetraconazole, (1.023) Triadimenol, (1.024) Tridemorph, (1.025) Triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H- 1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.029) (2R)-2-(1-chlorocyclopropyl)- 4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl) (1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl )-1H-1,2,4-triazole, (1.038) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.039) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.042) 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, (1.043) 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, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 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, (1.046) 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, (1.047) 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, (1.048) 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, (1.049) 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. 050) 2-[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-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) Mefentrifluconazole, (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2, 4-Triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058) 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, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2- Methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)- 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.067) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyl Imidoformamide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N -ethyl-N-methylimidoformamide, (1.071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.073) N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.074) N'-[5 -bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (1.076) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.077) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.078) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.079) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.080) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide. Mido, (1.081) Ipfentrifluconazole.

[0214] (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) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) isofetamide, (2.010) isopyrazam (anti-epimer enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimer enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimer racemate 1RS,4SR,9SR), (2.013) Isopyrazam (mixture of syn-epimeric racemate (1RS,4SR,9RS) and anti-epimeric racemate (1RS,4SR,9SR)), (2.014) Isopyrazam (syn-epimeric enantiomers 1R,4S,9R), (2.015) Isopyrazam (syn-epimeric enantiomers 1S,4R,9S), (2.016) Isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (2.017) Penflufen, (2.018) Penthiopyrad, (2.019) Pydiflumetofen, (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 boxamide, (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-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.029) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1 3-(Difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) Fluindapyr, (2.031) 3-(Difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(Difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole 1H-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3- (Difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) Isoflucipram, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl] -3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]- (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-N-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl) -5-Fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) Pyrapropoine.

[0215] (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) Flufenoxystrobin, (3.012) Fluoxastrobin, (3.013) Kresoxim-methyl, (3.014) Metominostrobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametstrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin, (3.021) (2E)-2-{ 2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5-dimethyl (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) Methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) Methyltetraprole, (3.031) Florylpicoxamide.

[0216] (4) Mitosis and cell division inhibitors, for example, (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)- )-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.014) 4-(2-bromo -4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1 ,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

[0217] (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.

[0218] (6) Compounds capable of inducing host defenses, such as (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.

[0219] (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, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

[0220] (8) Inhibitors of ATP production, for example, (8.001) silthiofam.

[0221] (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.

[0222] (10) Inhibitors of lipid and membrane synthesis, for example, (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

[0223] (11) Inhibitors of melanin biosynthesis, for example, (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

[0224] (12) Inhibitors of nucleic acid synthesis, such as (12.001) benalaxyl, (12.002) benalaxyl-M (chiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0225] (13) Signal transduction inhibitors, such as (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.

[0226] (14) Compounds that can act as uncouplers, for example, (14.001) fluazinam, (14.002) meptyldinocap.

[0227] (15) Further compounds, for example (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxadin, (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionate, (15.007) kufuraneb, (15.008) cyflufenamid, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) fluthianil, (15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, 15.014) Fosetyl sodium, (15.015) Methyl isothiocyanate, (15.016) Metrafenone, (15.017) Mildiomycin, (15.018) Natamycin, (15.019) Nickel dimethyldithiocarbamate, (15.020) Nitrothal-isopropyl, (15.021) Oxamocarb, (15.022) Oxathiapiproline, (15.023) Oxyfenthiin, (15.024) Pentachlorophenol and salts, (1 5.025) Phosphorous acid and its salts, (15.026) Propamocarb-fosetylate, (15.027) Pyriophenone (chlazafenone), (15.028) Tebufloquine, (15.029) Tecloftalam, (15.030) Tolnifanide, (15.031) 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, (15.032) 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, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) dipimethitrone, (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.036) 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, (15.037) 2-[3,5-bis(difluoro Methyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.038) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.039) 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, (15.040) 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, (15.041) Ipflufenoquine, (15.042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) 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}-3-chlorophenyl methanesulfonate, (15.044) 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, (15.045) 2-phenylphenol and salts, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047) quinofumeline, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.049) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050) 5-amino-1,3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene 2-Sulfonohydrazide, (15.052) 5-Fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-Fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-Fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055) But-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.056) (2Z)-3-amino-2-cyano-3-furan Ethylphenylacrylate, (15.057) Phenazine-1-carboxylic acid, (15.058) Propyl 3,4,5-trihydroxybenzoate, (15.059) Quinolin-8-ol, (15.060) Quinolin-8-ol sulfate (2:1), (15.061) tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.062) 5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one, (15.063) Aminopyrifen.

[0228] Biological pesticides as mixture components The compounds of formula (I) may be combined with a biological pesticide.

[0229] Biological pesticides include, inter alia, bacteria, fungi, yeasts, plant extracts and products formed by microorganisms (eg, proteins and secondary metabolites).

[0230] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.

[0231] 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).

[0232] 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).

[0233] 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, armyworm (Spodoptera frugiperda) mNPV, and African cotton leafworm (Spodoptera littoralis) NPV.

[0234] 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.

[0235] 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, especially rapeseed powder or mustard powder.

[0236] 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.

[0237] 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.

[0238] 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.

[0239] 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.

[0240] Transgenic plants, seed treatments, and integration events All plants that have received, via genetic modification, genetic material that confers on them particularly advantageous and beneficial properties ("traits") are encompassed among the transgenic plants or plant varieties (obtained by genetic engineering) that are preferably treated according to the present invention. Examples of such properties are improved plant growth, improved tolerance to high or low temperatures, improved tolerance to drought or salinity levels present in the water or soil, increased flowering ability, improved ease of harvesting, accelerated maturation, increased yield, improved quality and / or nutritional value of the harvested product, improved shelf life and / or improved processability of the harvested product, etc. Yet another particularly important example of such a property is improved resistance of plants to pests and harmful microorganisms (e.g., insects, arachnids, nematodes, mites, slugs and snails), for example by toxins formed within the plant, in particular by Bacillus thuringiensis (Bacillus Improved plant resistance to pests and harmful microorganisms (e.g., insects, arachnids, nematodes, mites, slugs, and snails) and also to plant pathogenic fungi, bacteria, and / or viruses, due to toxins formed in plants by genetic material derived from Cryptomeria thuringiensis (e.g., genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb, and CryIF, and combinations thereof). Improved plant resistance to fungi, bacteria, and / or viruses, for example, through systemic acquired resistance (SAR), systemin, phytoalexins, inducers, and further resistance genes and the proteins and toxins expressed thereby, and further improved plant tolerance to certain herbicidally active compounds (e.g., imidazolinones, sulfonylureas, glyphosate, or phosphinothricin) (e.g., "PAT" genes). Genes conferring the desired traits can also be present in combination with one another in transgenic plants.Examples of transgenic plants that may be mentioned include important crop plants, such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soybean, potato, sugar beet, sugarcane, tomato, pea and other types of vegetables, cotton, tobacco, rapeseed, and also fruit plants (fruit-bearing ones, apple, pear, citrus fruits and grapes), with maize, soybean, wheat, rice, potato, cotton, sugarcane, tobacco and rapeseed being of particular importance. A particularly important trait is the improved resistance of the plant to insects, arachnids, nematodes and slugs and snails.

[0241] 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., either 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.

[0242] 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.

[0243] 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.

[0244] 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.

[0245] 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.

[0246] 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.

[0247] 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.

[0248] 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.

[0249] 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.

[0250] 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.

[0251] It is also considered advantageous that the compounds of formula (I) can be used, in particular, also on transgenic seeds.

[0252] 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.

[0253] 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.

[0254] 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.

[0255] 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.

[0256] 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.

[0257] 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.

[0258] 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.

[0259] 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.

[0260] 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."

[0261] 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.

[0262] 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.

[0263] 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.

[0264] 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.

[0265] 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.

[0266] 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.

[0267] 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).

[0268] 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.

[0269] 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.

[0270] 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.

[0271] animal health In the field of animal health, i.e. veterinary medicine, the compounds of formula (I) are active against animal parasites, in particular against ecto- or endoparasites, which are typically and preferably arthropods, in particular insects or mites.

[0272] In the field of veterinary medicine, the compounds of formula (I) which have a favorable level of toxicity to warm-blooded animals are suitable in animal breeding and animal husbandry for controlling parasites which occur in livestock animals, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals (companion animals), and they are active against all or specific developmental stages of the parasites.

[0273] Agricultural livestock (farm animals) may include, for example, mammals such as sheep, goats, horses, donkeys, camels, water buffalo, rabbits, reindeer, fallow deer, and especially cattle and pigs; or poultry such as turkeys, ducks, geese, and especially chickens; or fish or crustaceans, for example fish or crustaceans in aquaculture; or possibly insects, such as bees.

[0274] Domestic or companion 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.

[0275] In certain embodiments, a compound of Formula (I) is administered to a mammal.

[0276] In another particular embodiment, the compounds of formula (I) are administered to birds, ie to caged birds, or, in particular, poultry.

[0277] In certain other embodiments, compounds of formula (I) are administered to livestock or companion animals, particularly companion animals such as cats and dogs.

[0278] 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.

[0279] 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.

[0280] 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.

[0281] 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..

[0282] In certain embodiments, the compounds of formula (I) are effective in reducing the incidence of parasites selected from Arthropods (more particularly, parasites selected from Acari and Insecta) in animals infected with such parasites to harmless levels.

[0283] 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.

[0284] Thus, one embodiment of the present invention relates to a compound of formula (I) for use as a pharmaceutical.

[0285] Another aspect relates to compounds of formula (I) for use as antiendoparasitical agents.

[0286] 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.

[0287] 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.

[0288] 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).

[0289] Another particular aspect of the present invention is a veterinary formulation selected from the group of ectoparasiticidal and endoparasiticidal formulations according to the above aspects, more particularly a veterinary formulation selected from the group of 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.

[0290] 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).

[0291] 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.

[0292] 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.

[0293] In relation to the field of animal health or veterinary medicine, the term "treatment" includes prophylactic, metaphylactic or therapeutic treatment.

[0294] 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.

[0295] 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.

[0296] 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).

[0297] 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) miscellaneous unspecified (multi-site) inhibitors; (9) chordotonal organ modulators; (10) mite growth inhibitors; (12) mitochondrial ATP synthase inhibitors, e.g., ATP synthase inhibitors. Slaptors; (13) uncouplers of oxidative phosphorylation by disrupting the proton gradient; (14) nicotinic acetylcholine receptor channel blockers; (15) inhibitors of chitin biosynthesis (type 0); (16) inhibitors of chitin biosynthesis (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; 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; another class of compounds, for example, butacarb, dimethylan, cloetocarb, phosphocarb, pirimiphos(-ethyl), parathion(-ethyl), methacrifos, isopropyl o-salicylate, trichlorfon, tigolaner, sulprofos, propafos, cebufos, pyridathion, protoate, diclofenthion, demeton-S-methylsulfone, isazophos, cyanofenphos, dialifos, carbophenothion, autathiofos, allomfenvinphos(-methyl), azinphos(-ethyl), chlorpyrifos(-ethyl), fosmetilan, iodofenphos, dioxabenzophos, formothion, fonofos, flupyrazophos, fensulfothion, etrimphos; Organochlorines, such as camphechlor, lindane, and heptachlor; or phenylpyrazoles, such as acetoprole, pyrafluprole, pyriprole, vaniliprole, and cisapronil; or isoxazolines, such as sarolaner, afoxolaner, lotilaner, and fluralaner; 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; Bee hive varroa acaricides, for example, organic acids, for example, formic acid, oxalic acid.

[0298] 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.

[0299] 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.

[0300] 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.

[0301] All named mixing partners, if their functional groups allow, can optionally form salts with suitable bases or acids.

[0302] 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).

[0303] 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.

[0304] 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.

[0305] 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.

[0306] If the compounds of formula (I) are resistance-breaking, vector control is likewise possible.

[0307] 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.

[0308] 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).

[0309] 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.

[0310] In a further embodiment, the compounds of formula (I) are used together with at least one further insecticide and / or at least one fungicide.

[0311] 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.

[0312] 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.

[0313] 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.

[0314] 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.

[0315] 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. [Table 1]

[0316] TIFF0007778687000031.tif81164

[0317] Description of preparation methods and intermediates Compounds of formula (I) can be prepared as shown in Scheme 1 below, where R 1 , R 2 , R 3 ,R 4 , R 5 , R 6 is as defined above.

[0318] Scheme 1 [ka]

[0319] The synthesis involves the residue R 5 and R 6 and one group X 1 The first conversion starts with pyrazine of formula (II) having X, which can be chlorine, bromine or iodine. These compounds are commercially available or can be prepared according to methods described in the art. 1The hydrogen atom adjacent to (III) is removed and replaced with a metal fragment consisting of a main group metal (e.g., Li, Mg, Zn) and an appropriate ligand, L. An example of such a transformation is given by F. Buron, N. Pie, A. Turck, G. Queguigner, J. Org. Chem. 2005, 70, 2616-2621, which shows the lithiation of 2-chloropyrazine using Li-TMP (2,2,6,6-tetramethylpiperidyl-lithium base) in THF. Other TMP-based reagents are summarized in a review by T. Klatt, J.T. Markiewicz, C. Samann, P. Knochel, J. Org. Chem. 2014, 79, 4253-4269. The metallated intermediate (III) is then trapped in situ with an aldehyde (IV) to generate a secondary alcohol (V). The metallation and reaction with the aldehyde are typically carried out in one pot in a polar aprotic solvent (e.g., THF, diethyl ether, dioxane). The temperature of the metallation step is typically below 0°C, preferably -78°C in a dry ice bath. After addition of the aldehyde, the temperature can be allowed to warm to 0°C or to room temperature. As an alternative to the one-pot procedure, the organometallic intermediate can be prepared in advance and then added to a solution of the aldehyde in a suitable aprotic solvent (e.g., THF, ether, or toluene).

[0320] The next step is to replace the hydroxy group of intermediate (V) with a fully protected nitrogen to produce an intermediate of formula (VII): PG 1 and PG 2 can be two independent protecting groups or can be combined to form a cyclic protecting group. Depending on the reaction and the protecting groups used, PG 1 and P.G. 2The other of the groups may represent hydrogen. Examples of protecting groups suitable for the protection of amino functions can be found in "T.W. Greene, P.G.M. Wuts "Protective Groups in Organic Chemistry" 3rd edition, Wiley Interscience, New York 1999, e.g., the Boc-group." The phthalimide protecting group is preferably used. The substitution of the hydroxy group can be carried out by converting the alcohol to a halide by methods known in the art (e.g., Appel reaction), by treatment with, for example, sulfuryl chloride followed by nucleophilic substitution with phthalimide, or by directly converting intermediate (V) with phthalimide in a Mitsunobu reaction with DIAD and triphenylphosphine in a suitable solvent (e.g., THF) at temperatures ranging from -40°C to 100°C (preferably, 0°C to room temperature).

[0321] R 4 The introduction of the leaving group X 2 This is carried out using a cross-coupling reaction with a reagent (VIII) having the formula: X 2 is a trialkylstannyl residue, a boronic acid, a boronic ester or a metal fragment M(L n ) [which has a metal such as Ni, Zn, Mg, etc. and a suitable ligand L]. The cross-coupling reaction is typically catalyzed by a transition metal catalyst (e.g., a palladium catalyst or a copper catalyst) and a suitable ligand. An extensive review of cross-coupling reactions is available in F. Diederich, A. de Meijere, "Metal catalyzed Cross Coupling Reactions, Second Edition", Wiley Online Library, online ISBN: 9783527619535.

[0322] A variant of the cross-coupling reaction involves the use of trialkyltrialkylstannyl residues, boronic acids, boronic esters or metal fragments M(L n) [which has a metal such as Ni, Zn, Mg, etc. and a suitable ligand L] to form the moiety X of intermediate (VII). 1 In this case, intermediate (VIII) may be substituted with a group X selected from, for example, Cl, Br, I, triflate or the like. 2 It will be necessary to have

[0323] X 1 =Cl, Br or I and X 2 Suitable conditions for the coupling of ═trialkylstannyl, boronic acid, or boronate ester include the use of 0.01-0.5 equivalents of a palladium source (e.g., PdCl(dppf)xDCM, palladium diacetate, tetrakistriphenylphosphine palladium, or another compound) along with a ligand. The ligand can be selected from phosphine or N-heterocyclic carbene ligands; a summary of some ligands is given in R. Martin, S.L. Buchwald, Acc. Chem. Res. 2008, 61, 1461-1473.

[0324] The product of the cross-coupling reaction (IX) must be deprotected in the next step. If a phthalimide protecting group is used, this can be achieved by reacting (IX) with hydrazine hydrate in a suitable solvent (e.g., ethanol) at or above room temperature.

[0325] The compound of formula (I) can be prepared by converting intermediate (X) into carboxylic acid derivative (XI) [wherein X 3is Cl, O-acyl or OH. When X is Cl or O-acyl, (X) and (XI) are reacted directly in a solvent (e.g., DMF, THF or the like) in the presence of a base (e.g., DIPEA, triethylamine or N-methylmorpholine). When X is OH, the acid (XI) needs to be activated using a coupling agent (e.g., HATU, TBTU, TCTU, PyBOP, etc.) before reacting with (X), or alternatively, converted to the corresponding acid chloride or acid anhydride. The resulting product (Ia) can be obtained by reacting R 1 is H. R other than hydrogen is a compound of the present invention. 1 An alkylation reaction with an alkylating agent (XII) can be used to achieve a compound having the formula: Examples of leaving groups LG include Cl, Br, I, tosylate, mesylate, or triflate. The reaction can be carried out by mixing reagents (Ia) and (XII) together with a base (e.g., KCO or DIPEA) in a suitable solvent (e.g., acetonitrile or DMF) and reacting them at a temperature ranging from 20 to 100 °C. The compound of formula (Ib) can then be isolated and, if necessary, purified using techniques well known in the art (e.g., chromatography).

[0326] In compound (I), R 4 is a pyridine group, in the above scheme 1, preferably X 1 is Cl and X 2 is Zn—Cl, the Pd catalyst is Pd 2 (dba) 3 catalyst, and the ligand L is X-Phos.

[0327] In compound (I), R 4 is a pyrimidine group, in the above scheme 1, preferably X 1 is Cl and X 2 is SnBu3, the Pd catalyst is PdCl2*2APhos catalyst, and ZnCl2 is added as an additive.

[0328] In compound (I), R 4 is a thiazole group, in the above scheme 1, preferably X 1 is Cl and X 2 is SnBu3, the Pd catalyst is PdCl2*2PPh3 catalyst, and the ligand L is PPh3.

[0329] Scheme 2 [ka]

[0330] In a variation of the synthetic route described above, the Mitsunobu reaction and cross-coupling reactions can be applied in reverse order, as shown in Scheme 2. In this case, R 4 Introduction of the group PG leads to intermediate XIII, which is then further converted to intermediate IX by a Mitsunobu reaction as described above. In some cases, this can be advantageous in yield or feasibility. 1 and PG 2 Please refer to the definition above for the meaning of

[0331] R 4 is attached to the pyrazine moiety by a nitrogen atom, X in intermediates V and VII 1 is preferentially halogen (in particular Cl, Br or I), and X 2 is R 4 In particular, this is the hydrogen bonded to the nitrogen atom in R 4This is true when the aryl group is an optionally substituted pyrazole or imidazole. A general strategy for these molecules can follow the order of steps shown in either Scheme 1 or Scheme 2. Preferentially, the introduction of the pyrazole or imidazole is carried out before the introduction of the amine, as shown in Scheme 2. The current cross-coupling step is carried out using a metal catalyst, optionally a ligand, a base, and a solvent. Metal catalysts useful in this step include copper(I) salts and copper(II) salts, preferentially copper(I) halides, such as copper(I) iodide. The use of a ligand can be beneficial. The selection of an appropriate ligand depends on the metal catalyst. In the case of copper(I) salts, 1,2-diamines, such as TMEDA or trans-N,N,N',N'-tetramethylcyclohexane-1,2-diamine, are used. Catalytic amounts of the metal catalyst and ligand are used, typically in the range of 0.01 to 0.5 molar equivalents, respectively. The base can be an alkali or alkaline earth carbonate, such as calcium carbonate, sodium carbonate, potassium carbonate, or cesium carbonate. The solvent can be DMF, THF, 1,4-dioxane, toluene, chlorobenzene, or other organic solvents commonly used in cross-coupling reactions. The reaction is carried out at room temperature or above, preferably at 100 to 120°C.

[0332] R 4 When is a pyrazole, the preferred conditions for the cross-coupling are 0.3 equivalents of copper(I) iodide, 0.3 equivalents of trans-N,N,N',N'-tetramethylcyclohexane-1,2-diamine, and an excess of potassium carbonate in refluxing toluene.

[0333] In certain cases, the compounds of the present invention comprise R 4 These manipulations can be achieved by modifying the substituents after the introduction of R 2 Alternatively, the reaction can be carried out in the presence of a moiety R 2(See Scheme I) For example, R 4 The ester group located at can be saponified by standard methods. Preferred methods for saponifying esters include lithium or sodium hydroxide in a mixture of solvents (e.g., methanol and THF) and water at temperatures ranging from room temperature to reflux, or lithium iodide in pyridine at temperatures above 100°C. The resulting carboxylic acid can be converted to a carboxamide using a coupling agent (e.g., TBTU, HATU, EDCI, or other reagents known in the art). The carboxylic acid ester can also be converted to a cyanide using Burgess's reagent. Alternatively, the carboxylic acid can be converted to an amine using a Curtius rearrangement, and the resulting amino group can then be acylated using a coupling agent (e.g., TBTU, HATU, EDCI, or other reagents known in the art) to provide R via the nitrogen atom. 4 can be used to generate a carboxamide linked to

[0334] The process according to the present invention for preparing a compound of formula (I) is preferably carried out using a diluent. Useful diluents for carrying out the process according to the present invention include water and all inert solvents. Examples thereof include halohydrocarbons (e.g., chlorohydrocarbons such as tetrachloroethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichloroethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene), alcohols (e.g., methanol, ethanol, isopropanol, butanol), ethers (e.g., ethyl propyl ether, methyl tert-butyl ether, anisole, phenetole, cyclohexylmethyl ether), and the like. dimethyl ether, diethyl ether, dipropyl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, 1,4-dioxane, dichlorodiethyl ether, and polyethers of ethylene oxide and / or propylene oxide), amines (e.g., trimethylamine, triethylamine, tripropylamine, tributylamine, N-methylmorpholine, pyridine, and tetramethylenediamine), nitrohydrocarbons (e.g., nitromethane, nitroethane, nitropropane, nitrobenzene, chloronitrobenzene, o-nitrotoluene);Nitriles (e.g., acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile), tetrahydrothiophene dioxide, dimethyl sulfoxide, tetramethylene sulfoxide, dipropyl sulfoxide, benzyl methyl sulfoxide, diisobutyl sulfoxide, dibutyl sulfoxide, diisoamyl sulfoxide, sulfones (e.g., dimethyl sulfone, diethyl sulfone, dipropyl sulfone, dibutyl sulfone, diphenyl sulfone, dihexyl sulfone, methyl ethyl sulfone, ethyl propyl sulfone, ethyl isobutyl sulfone, and pentamethylene sulfone), aliphatic, alicyclic, or aromatic hydrocarbons (e.g., pentane, hexane, heptane, octane, nonane, and industrial hydrocarbons), and also so-called "white spirits", which contain components having a boiling point in the range of, for example, 40°C to 250°C. Methionine, petroleum fractions boiling in the range of 70 to 190 ° C, cyclohexane, methylcyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, esters (e.g., methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, dimethyl carbonate, dibutyl carbonate, and ethylene carbonate); amides (e.g., hexamethylphosphoric triamide, formamide, N-methylformamide, N,N-dimethylformamide, N,N-dipropylformamide, N,N-dibutylformamide, N-methylpyrrolidine, N-methylcaprolactam, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidine, octylpyrrolidone, octylcaprolactam, 1,3-dimethyl-2-imidazolinedione, N-formylpiperidine, N,N'-diformylpiperazine), and ketones (e.g., acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone);

[0335] The preparation process according to the invention can also be carried out in a mixture of the solvents and diluents mentioned above.

[0336] When carrying out the preparation method according to the present invention, the reaction temperature can be varied within a relatively wide range. Generally, the temperature used is from -30°C to +150°C, preferably from -10°C to +100°C.

[0337] The process according to the invention is generally carried out under atmospheric pressure, but it can also be carried out under elevated or reduced pressure, generally at an absolute pressure between 0.1 bar and 15 bar.

[0338] To carry out the preparation method of the present invention, the starting materials are generally used in approximately equimolar amounts.However, it is also possible to use one of the components in a relatively large excess amount.The reaction is generally carried out in a suitable diluent, in the presence of a reaction aid, optionally under a protective gas atmosphere (for example, under nitrogen, argon or helium), and the reaction mixture is generally stirred at the required temperature for several hours.Post-treatment is carried out in a conventional manner (see Preparation Examples).

[0339] The basic reaction auxiliary used to carry out the preparation process according to the invention can be any suitable acid-binding agent. Examples include alkaline earth metal compounds or alkali metal compounds (e.g., hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium), amidine bases or guanidine bases (e.g., 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD); diazabicyclo[4.3.0]nonene (DBN), diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]undecene (DBU), cyclohexyltetrabutylguanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), N,N,N,N-tetramethyl-1,8-naphthalenediamine, pentamethylpiperidine), and amines, especially tertiary amines (e.g., triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine, triamylamine, trihexylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, N,N-dimethyl-p-aminopyridine, N-methylpyrrolidine, N-methylpiperidine, N-methylimidazole, N-methylpyrazole, N-methylmorpholine, N-methylhexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylaminopyridine, quinoline, 2-picoline, 3-picoline, pyrimidine, acridine, N,N,N',N'-tetramethylenediamine, N,N,N',N'-tetraethylenediamine, quinoxaline, N-propyldiisopropylamine, N-ethyldiisopropylamine, N,N'-dimethylcyclohexylamine, 2,6-lutidine, 2,4-lutidine or triethylenediamine).

[0340] Acidic reaction auxiliaries used to carry out the preparation process according to the invention include all mineral acids (for example hydrohalic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid, and also sulfuric acid, phosphoric acid, phosphorous acid, nitric acid), Lewis acids (for example aluminum(III) chloride, boron trifluoride or its etherate, titanium(IV) chloride, tin(IV) chloride), and organic acids (for example formic acid, acetic acid, propionic acid, malonic acid, lactic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, tartaric acid, oleic acid, methanesulfonic acid, benzoic acid, benzenesulfonic acid or paratoluenesulfonic acid).

[0341] The following examples further illustrate and explain the present invention without limiting it. [Example]

[0342] Preparation Examples Analysis method Method 1 (LC-MS) Instrument: Agilent MS Quad 6150; HPLC: Agilent 1290; Column: Waters Acquity UPLC HSS T3 1.8 μm 50 × 2.1 mm; Eluent A: 1 L water + 0.25 mL 98% formic acid, Eluent B: 1 L acetonitrile + 0.25 mL 99% formic acid; Gradient: 0.0 min 90% A → 0.3 min 90% A → 1.7 min 5% A → 3.0 min 5% A; Oven temperature: 50 °C; Flow rate: 1.20 mL / min; UV detection: 205-305 nm.

[0343] Method 2 (LC-MS) Instrument MS: Thermo Scientific FT-MS; Instrument for UHPLC+: Thermo Scientific UltiMate 3000; Column: Waters, HSST3, 2.1 × 75 mm, C18 1.8 μm; Eluent A: 1 L water + 0.01% formic acid; Eluent B: 1 L acetonitrile + 0.01% formic acid; Gradient: 0.0 min 10% B → 2.5 min 95% B → 3.5 min 95% B; Oven temperature: 50 °C; Flow rate: 0.90 mL / min; UV detection: 210 nm / optimal integration path 210-300 nm.

[0344] Method 3 (LC-MS) Instrument: Waters Single Quad MS System; Instrument Waters UPLC Acquity; Column: Waters BEH C18 1.7μ 50 × 2.1 mm; Eluent A: 1 L water + 1.0 mL 25% ammonia, Eluent B: 1 L acetonitrile; Gradient: 0.0 min 92% A → 0.1 min 92% A → 1.8 min 5% A → 3.5 min 5% A; Oven temperature: 50 °C; Flow rate: 0.45 mL / min; UV detection: 210 nm.

[0345] Method 4 (LC-MS) Analysis method E Instrument: SHIMADZU LCMS - UFLC 20-AD - LCMS 2020 MS Detector; Column: Ascentis Express C18 2.7 μm, 50 × 3.0 mm; Eluent A: water + 0.05% by volume trifluoroacetic acid, Eluent B: acetonitrile + 0.05% by volume trifluoroacetic acid; Gradient: assigned for each compound; Flow rate: 1.2 mL / min; Temperature: 40 °C; PDA scan: 190-400 nm.

[0346] Method 5 (LC-MS) Analysis method E1 Instrument: SHIMADZU LCMS - UFLC 20-AD - LCMS 2020 MS detector; Column: Ascentis Express C18 2.7 μm, 50 × 2.1 mm; Eluent A: water + 0.1% by volume formic acid, Eluent B: acetonitrile + 0.1% by volume formic acid; Gradient: assigned for each compound; Flow rate: 1.5 mL / min; Temperature: 40 °C; PDA scan: 190-400 nm.

[0347] Method 6 (LC-MS) Analysis method F Instrument: SHIMADZU LCMS - UFLC 20-AD - LCMS 2020 MS detector; Column: Shim-pack XR-ODS, 2.2 μm, 3.0 × 50 mm; Eluent A: water + 0.05% trifluoroacetic acid (volume), Eluent B: acetonitrile + 0.05% trifluoroacetic acid (volume); Gradient: assigned for each compound; Flow rate: 1.5 mL / min; Temperature: 40 °C; PDA scan: 190-400 nm. Method 7 (Chiral HPLC) Column: Daicel Chiralpak ID, 5 μm 250×4.6 mm; eluent A: iso-hexane, eluent B: 2-propanol, isocratic A:B=1:1, 40° C.; flow rate: 1.0 mL / min; UV detection: 220 nm.

[0348] Method 8 (optical rotation) Equipment: Anton Paar Polarimeter MCP200 Specific rotation [α] (depending on wavelength, temperature, light path, solvent and concentration).

[0349] Method 9 (HPLC-MS) System MS: Waters TOF instrument; System UPLC: Waters Acquity I-CLASS; Column: Waters Acquity UPLC HSS T3 1.8 μm 50 × 1 mm; Eluent A: 1 L water + 0.100 mL 99% IgE formic acid, Eluent B: 1 L acetonitrile + 0.100 mL 99% IgE formic acid; Gradient: 0.0 min 90% A → 1.2 min 5% A → 2.0 min 5% A; Oven: 50 °C; Flow rate: 0.40 mL / min; UV detection: 210 nm.

[0350] Method 10 (HPLC-MS) System MS: Waters TOF instrument; System UPLC: Waters Acquity I-CLASS; Column: Waters Acquity UPLC HSS T3 1.8 μm 50 × 1 mm; Eluent A: 1 L water + 0.100 mL 99% IgE formic acid, Eluent B: 1 L acetonitrile + 0.100 mL 99% IgE formic acid; Gradient: 0.0 min 95% A → 6.0 min 5% A → 7.5 min 5% A; Oven: 50 °C; Flow rate: 0.35 mL / min; UV detection: 210 nm.

[0351] Method 11 (HPLC-MS) Instrument: Waters ACQUITY SQD UPLC System; Column: Waters Acquity UPLC HSS T3 1.8 μm 50 × 1 mm; Eluent A: 1 L water + 0.25 mL 99% IgE formic acid, Eluent B: 1 L acetonitrile + 0.25 mL 99% IgE formic acid; Gradient: 0.0 min 90% A → 1.2 min 5% A → 2.0 min 5% A; Oven: 50 °C; Flow rate: 0.40 mL / min; UV detection: 210 nm.

[0352] General synthesis method General synthesis method 1 Synthesis of MIDA boronate MIDA boronate was synthesized according to the method described in the literature (GR Dick, DM Knapp, EP Gillis, MD Burke, Org. Lett. 2010, 12, 2314-2317).

[0353] On a scale of approximately 100 mmol (calculated based on the 2-bromopyridine derivative), the procedure worked as described herein. The 2-bromopyridine derivative (1 equiv.) and tripropan-2-yl borate (1.4 equiv.) were dissolved in THF (200 mL), and the solution was cooled to −78°C. n-Butyllithium (2.5 M in hexanes, 1.2 equiv.) was added slowly over 90 min. Stirring at −78°C was maintained for an additional 60 min, after which the cooling bath was removed and the mixture was allowed to warm to ambient temperature. In a separate three-neck round-bottom flask equipped with a distillation apparatus and internal thermometer, a solution of 2,2′-(methylimino)diacetic acid (1.6 equiv.) in DMSO (dried over 3 Å molecular sieves, 150 mL) was heated to 125–130°C. The suspension of boronate in THF was added slowly over approximately 2 hours, and the THF was distilled off, maintaining the temperature in the range of 115-125° C. Finally, the mixture was stirred for a further 20 minutes and then allowed to stand overnight. DMSO was distilled off under reduced pressure, and the residue was absorbed onto diatomaceous earth and chromatographed on 340 g of silica using a ternary gradient of dichloromethane-ethyl acetate and then ethyl acetate-THF.

[0354] General synthesis method 2 Cross-coupling of MIDA boronates with halogenated pyrazines (rac)-1-(3-bromopyrazin-2-yl)ethan-1-ol (1 equivalent), MIDA boronate (1.2 equivalents), and diethanolamine (1.0 equivalents) were dissolved in DMF (approximately 4 mL per mmol of pyrazine halide) under argon. XPhos Pd G2 (0.1 equivalents), copper(II) acetate (0.5 equivalents), and potassium phosphate (3.0 equivalents) were added. The mixture was heated to 110 °C in a single-mode microwave reactor. It was then poured into water and extracted three times with MTBE. The organic extract was dried over anhydrous sodium sulfate, evaporated, and purified by silica gel chromatography using a cyclohexane-ethyl acetate gradient to give the title compound.

[0355] General synthesis method 3 Mitsunobu reaction Substituted (pyrazin-2-yl)ethan-1-ol (1 equivalent) was dissolved in THF (approximately 3.0 mL / mmol), and 1H-isoindole-1,3(2H)-dione (1.50 equivalents) and triphenylphosphine (1.50 equivalents) were added. The mixture was cooled to 0°C, and then DIAD (1.50 equivalents) was slowly added, and the mixture was stirred for an additional 30 minutes. The solvent was distilled, and the crude product was purified by preparative HPLC (RP C-18, water-acetonitrile gradient with 0.1% TFA) to give the title compound.

[0356] General synthesis method 4 Hydrazinolysis of phthalimide groups The phthalimide-protected amine (1 equiv.) was dissolved in ethanol (approximately 10 mL / mmol) and hydrazine hydrate (80% in water, 5 equiv.) was added. The mixture was heated to reflux for 1 h, then poured into water and extracted three times with dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and evaporated. In some cases, the crude product was purified by flash chromatography to afford the pure title compound.

[0357] General synthesis method 5 Amide Coupling Amine (1.0 equiv.), carboxylic acid (1.3 equiv.), and DIPEA (3.0 equiv.) were dissolved in DMF (approximately 0.17 mmol of amine per mL of DMF). The solution was cooled to 0°C on an ice-water bath, and HATU (1.5 equiv.) was added. The cooling bath was removed, and the mixture was stirred for 30 min. Water was then added. The precipitated product was collected in a filter funnel, dried under vacuum, and finally purified by preparative HPLC (RP-C18, water-acetonitrile gradient with 0.1% TFA).

[0358] General synthesis method 6 Copper-catalyzed coupling of azoles (rac)-1-(3-Bromopyrazin-2-yl)ethan-1-ol (Intermediate 22A, 1 equiv.) was dissolved in toluene (3.0 mL per 1.0 mmol of bromopyrazine), and azole (1.5 equiv.), potassium carbonate (2.5 equiv.), copper(I) iodide (0.3 equiv.), and trans-N,N,N',N'-tetramethylcyclohexane-1,2-diamine (0.3 equiv.) were added. The mixture was heated to reflux for 1 h and then poured into water. It was extracted three times with ethyl acetate, and the combined organic extracts were washed twice with 20% aqueous ammonia, once with water, and finally once with brine. The organic phase was dried over anhydrous sodium sulfate, evaporated, and the residue was purified on silica gel using a cyclohexane-ethyl acetate gradient. In some cases, the crude product was repurified by preparative HPLC (RP-C18 column with a water-acetonitrile gradient containing 0.1% TFA) to afford the title compound.

[0359] Synthetic Intermediates Intermediate 1A (rac)1-(3-chloropyrazin-2-yl)ethan-1-ol [ka]

[0360] The reaction was carried out in flame-dried glassware under dry argon. 2,2,6,6-Tetramethylpiperidine (11 mL, 65 mmol) was dissolved in THF and cooled to -78 °C in an acetone-dry ice bath. n-Butyllithium (2.5 M in hexanes, 25 mL, 64 mmol) was added dropwise so that the temperature did not exceed -70 °C. Stirring was then maintained at -78 °C for 30 minutes. 2-Chloropyrazine (5.73 g, 50.0 mmol) was then added dropwise, and the mixture was stirred for 1 hour. After this time, acetaldehyde (5.6 mL, 100 mmol) was added, and the mixture was allowed to warm to room temperature and stirred for an additional 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using a gradient of cyclohexane and 0-40% ethyl acetate to give 4.60 g (100% pure, 58% yield) of the title compound.

[0361] LC-MS (Method 1): R t = 0.51 min; low ionization was observed. 1 H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.415 (15.85), 1.431 (16.00), 1.989 (0.55), 5.076 (0.46), 5.092 (1.88), 5.108 (2.88), 5.124 (1.97), 5.140 (0.51), 5.399 (4.89), 5.414 (4.45), 8.436 (3.29), 8.442 (3.57), 8.661 (3.47), 8.667 (3.40).

[0362] Intermediate 2A (rac)-2-[1-(3-chloropyrazin-2-yl)ethyl]-1H-isoindole-1,3(2H)-dione [ka]

[0363] (rac)1-(3-chloropyrazin-2-yl)ethan-1-ol (Intermediate 1A, 4.60 g, 29.0 mmol) was dissolved in THF (110 mL), and 1H-isoindole-1,3(2H)-dione (6.40 g, 43.5 mmol) and triphenylphosphine (11.4 g, 43.5 mmol) were added at room temperature. The mixture was then cooled on an ice bath, and DIAD (7.8 mL, 95% purity, 44 mmol) was added slowly. The reaction was allowed to warm to ambient temperature and stirred for 2 hours. The solvent was distilled, and the residue was directly loaded onto a silica gel column (100 g of silica gel) and chromatographed using a gradient of cyclohexane and 0-35% ethyl acetate. 5.37 g (98% purity, 63% yield) of the title compound was obtained.

[0364] LC-MS (Method 2): R t = 1.69 min; MS (ESIpos): m / z = 288 [M+H] + 1 H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.208 (0.56), 1.219 (0.86), 1.231 (0.50), 1.793 (5.84), 1.805 (5.93), 5.696 (0.41), 5.708 (1.33), 5.720 (1.34), 5.731 (0.43), 7.868 (16.00), 8.490 (2.02), 8.494 (2.14), 8.702 (2.31), 8.706 (2.29).

[0365] Intermediate 3A (rac)-2-{1-[3-(pyridin-2-yl)pyrazin-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione [ka]

[0366] The reaction was carried out in flame-dried glassware under dry argon. The organozinc reagent (solution A) was prepared as described in M.R. Luzung, J.S. Patel, J. Yin, J. Org. Chem. 2010, 75, 8330-8332.

[0367] Solution A: A three-necked round-bottom flask equipped with a stir bar was charged with isopropylmagnesium chloride (2.0 M in THF, 2.75 mL, 5.5 mmol). To this mixture was added neat 2-bromopyridine (0.476 mL, 5.0 mmol, 1.0 equiv) dropwise at a temperature not exceeding 30°C. The mixture was stirred at room temperature for 3 hours. Then, zinc chloride (1.9 M in THF, 3.16 mL, 6.0 mmol) was added dropwise at a temperature not exceeding 30°C, and stirring was continued at room temperature for an additional 60 minutes. This solution was used directly in the subsequent cross-coupling reaction.

[0368] Solution B: Pd2(dba)3 (18.3 mg, 20.0 μmol) and dicyclohexyl[2',4',6'-tri(propan-2-yl)biphenyl-2-yl]phosphane (XPhos, 38.1 mg, 80.0 μmol) were dissolved in THF (2.0 mL). The mixture was heated to 65°C for 10 min, and then (rac)-2-[1-(3-chloropyrazin-2-yl)ethyl]-1H-isoindole-1,3(2H)-dione (Intermediate 2A, 288 mg, 1.00 mmol) was added, and stirring at 65°C was continued for an additional 15 min.

[0369] Finally, an aliquot of solution A (2.0 mL, 1.5 mmol) was added to solution B in one portion, and the mixture was stirred at 65° C. for 7 h. Water (3.0 mL) and concentrated aqueous sodium bicarbonate (3.0 mL) were added, the mixture was extracted with ethyl acetate, and the organic extract was washed with brine, dried over anhydrous sodium sulfate, and evaporated. The crude product was purified by preparative HPLC using RP C-18 10 μm material and a gradient of water (+0.1% TFA)-acetonitrile (+0.1% TFA) (90:10 → 5:95). 219 mg (99% pure, 66% yield) of the title compound was obtained.

[0370] LC-MS (Method 2): R t = 1.51 min; MS (ESIpos): m / z = 331 [M+H] + 1 H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.700 (15.91), 1.712 (16.00), 5.747 (3.09), 6.358 (1.15), 6.369 (3.78), 6.381 (3.73), 6.393 (1.13), 7.345 (2.24), 7.358 (2.63), 7.366 (2.41), 7.714 (4.89), 7.719 (5.36), 7.723 (6.03), 7.728 (7.85), 7.735 (1.21), 7.757 (3.00), 7.773 (10.68), 7.778 (6.32), 7.782 (5.81), 7.787 (5.19), 7.796 (2.95), 7.809 (3.67), 7.822 (1.46), 8.542 (3.70), 8.550 (3.71), 8.666 (4.22), 8.669 (8.32), 8.677 (7.99).

[0371] Intermediate 4A (rac)-1-[3-(pyridin-2-yl)pyrazin-2-yl]ethan-1-amine [ka]

[0372] (rac)-2-{1-[3-(pyridin-2-yl)pyrazin-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione (Intermediate 3A, 218 mg, 660 μmol) was dissolved in ethanol (3.3 mL), hydrazine hydrate (160 μL, 3.3 mmol) was added, and the mixture was heated to reflux for 2 h. The solvent was evaporated, ethyl acetate was added, and the mixture was stirred at room temperature for 30 min. The precipitate was filtered off, and the filtrate was evaporated. The crude title compound (143 mg, 87% purity, 94% yield) was used in the next step without further purification.

[0373] LC-MS (Method 3): R t = 0.92 min; MS (ESIneg): m / z = 199 [MH] - 1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.035 (0.48), 1.046 (0.48), 1.107 (1.71), 1.177 (0.45), 1.188 (0.44), 1.416 (15.78), 1.428 (16.00), 1.745 (4.66), 2.070 (3.46), 3.078 (0.63), 3.309 (1.12), 3.395 (0.61), 4.898 (0.98), 4.909 (3.05), 4.920 (3.04), 4.931 (1.00), 7.529 (1.82), 7.533 (1.81), 7.537 (1.96), 7.540 (2.67), 7.544 (2.03), 7.548 (1.92), 7.552 (1.89), 8.016 (0.84), 8.019 (0.84), 8.030 (3.14), 8.033 (3.26), 8.041 (7.28), 8.043 (6.99), 8.052 (0.99), 8.709 (6.08), 8.713 (7.38), 8.725 (2.35), 8.727 (3.04), 8.729 (2.35), 8.733 (2.36), 8.735 (3.49), 8.737 (2.14), 8.749 (6.63), 8.753 (5.60).

[0374] Intermediate 5A (rac)-2-(1-(3-(thiazol-2-yl)pyrazin-2-yl)ethyl)isoindoline-1,3-dione [Chemical formula]

[0375] To a solution of (rac)-2-[1-(3-chloropyrazin-2-yl)ethyl]-1H-isoindole-1,3(2)-dione (Intermediate 2A, 1.2 g, 4.17 mmol) and dichlorobis(triphenylphosphine)palladium(II) (293 mg, 0.42 mmol) in N,N-dimethylformamide (24 mL) was added 2-(tributylstannyl)thiazole (1.9 g, 5.01 mmol) at room temperature under a N atmosphere. The resulting mixture was stirred overnight at 85 °C under a N atmosphere. After cooling to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:petroleum ether = 1:3) to afford 512 mg (31% purity) of the product as a white solid.

[0376] LC-MS (Method 6, gradient 0.01-1.50 min 5-100% B): R t = 0.873 min; MS (ESIpos): m / z = 337 [M+H] + .

[0377] Intermediate 6A (rac)-1-(3-(thiazol-2-yl)pyrazin-2-yl)ethan-1-amine; [ka]

[0378] To a solution of (rac)-2-(1-(3-(thiazol-2-yl)pyrazin-2-yl)ethyl)isoindoline-1,3-dione (Intermediate 5A, 520 mg, 0.48 mmol, 31% purity) in ethanol (8 mL) was added hydrazine monohydrate (120 mg, 2.40 mmol). The resulting mixture was stirred at 95° C. for 2 hours. After cooling to room temperature, the solvent was removed under reduced pressure, ethyl acetate was added, and the solution was stirred for 30 minutes. The solid was then filtered, and the filtrate was concentrated to give 300 mg of crude product as a yellow solid.

[0379] LC-MS (Method 6, gradient 0.01-1.50 min 5-100% B): R t = 0.572 min; MS (ESIpos): m / z = 207 [M+H] + .

[0380] Intermediate 7A 5-tert-butylnicotinic acid [ka]

[0381] To a solution of 5-bromonicotinic acid (4.0 g, 19.99 mmol) and copper(I) iodide (380 mg, 2.00 mmol) in tetrahydrofuran (100 mL) was added dropwise a solution of tert-butylmagnesium chloride in tetrahydrofuran (1.7 M, 29.4 mL, 50.0 mmol) at −70° C. under a N atmosphere. The mixture was then stirred at room temperature overnight. The reaction was quenched by careful addition of ammonium chloride solution. The resulting mixture was concentrated, poured into water, and then extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography to give 80 mg of the desired product as a white solid.

[0382] LC-MS (Method 4, gradient 0.01-2.50 min 5-100% B): R t = 0.718 min; MS (ESIpos): m / z = 180 [M+H] + .

[0383] Intermediate 8A (rac)-2-(1-(3-(pyrimidin-2-yl)pyrazin-2-yl)ethyl)isoindoline-1,3-dione [ka]

[0384] To a solution of (rac)-2-[1-(3-chloropyrazin-2-yl)ethyl]-1H-isoindole-1,3(2)-dione (Intermediate 2A, 1.3 g, 4.52 mmol) in N,N-dimethylformamide (39 mL) was added Pd(AMPhos)Cl (CAS RN 887919-35-9, 0.3 g, 0.45 mmol), ZnCl (0.6 g, 4.52 mmol), and 2-(tributylstannyl)pyrimidine (2.5 g, 6.78 mmol) under a N atmosphere. The resulting mixture was stirred at 120 °C overnight. After cooling to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layer was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:petroleum ether = 1:5) to afford 600 mg of the product (40% yield) as a white solid.

[0385] Intermediate 9A (rac)-1-(3-(pyrimidin-2-yl)pyrazin-2-yl)ethan-1-amine [ka]

[0386] To a solution of rac-2-(1-(3-(pyrimidin-2-yl)pyrazin-2-yl)ethyl)isoindoline-1,3-dione (Intermediate 8A, 600 mg, 1.81 mmol) in ethanol (8 mL) was added hydrazine monohydrate (453 mg, 9.05 mmol). The resulting mixture was stirred at 95° C. for 2 hours. After cooling to room temperature, the solvent was removed under reduced pressure, ethyl acetate was added, and the solution was stirred for 30 minutes. The solid was then filtered, and the filtrate was concentrated to give 312 mg (85%) of crude product as a yellow solid.

[0387] LC-MS (Method 4, gradient 0.01-1.80 min 5-100% B): R t = 0.457 min; MS (ESIpos): m / z = 202 [M+H] + .

[0388] Intermediate 10A 2-(5-chloropyridin-2-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione [ka]

[0389] Following General Synthesis Method 1, 13.6 g (100% purity, 49% yield) of the title compound was synthesized from 2-bromo-5-chloropyridine (20.0 g, 104 mmol) obtained as a crystalline solid.

[0390] LC-MS (Method 2): R t = 0.96 min; MS (ESIpos): m / z = 269 [M+H] + 1 H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.106 (16.00), 1.122 (0.51), 2.823 (0.67), 3.077 (4.92), 4.060 (2.24), 4.102 (2.85), 4.376 (2.77), 4.419 (2.18), 7.572 (1.12), 7.592 (1.29), 7.862 (0.88), 7.868 (0.88), 7.882 (0.78), 7.888 (0.77), 8.724 (1.09), 8.729 (1.07).

[0391] Another MIDA boronate prepared by general method 1: Intermediate 11A 6-Methyl-2-[5-(trifluoromethyl)pyridin-2-yl]-1,3,6,2-dioxazaborocane-4,8-dione [ka]

[0392] Following General Synthesis Method 1, 2.56 g (100% purity, 38% yield) of the title compound was synthesized from 2-bromo-5-trifluoromethylpyridine (5.00 g, 22.1 mmol) obtained as a crystalline solid.

[0393] LC-MS (Method 2): Rt = 1.19 min; MS (ESIpos): m / z = 303 [M+H] + 1 H-NMR (600 MHz, DMSO-d6) δ [ppm]: 0.871 (0.42), 0.884 (0.42), 1.107 (3.20), 1.121 (1.66), 2.575 (16.00), 2.783 (1.36), 2.800 (0.66), 2.826 (0.55), 2.919 (2.76), 3.078 (0.89), 3.995 (0.46), 4.024 (0.68), 4.103 (5.55), 4.132 (6.70), 4.157 (0.77), 4.167 (1.28), 4.187 (0.57), 4.196 (1.58), 4.342 (1.31), 4.370 (0.96), 4.417 (6.51), 4.445 (5.50), 7.790 (2.61), 7.804 (2.83), 8.142 (2.22), 8.155 (2.13), 9.052 (3.80).

[0394] Intermediate 12A 2-(5-Methoxypyridin-2-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione [ka]

[0395] Following General Synthesis Method 1, 3.25 g (95% purity, 22% yield) of the title compound was synthesized from 2-bromo-5-methoxypyridine (10.0 g, 53.2 mmol) obtained as a crystalline solid.

[0396] LC-MS (Method 3): R t = 0.88 min; MS (ESIpos): m / z = 265 [M+H] + 1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 2.514 (13.24), 2.663 (1.41), 3.823 (16.00), 3.824 (15.35), 3.844 (1.76), 4.032 (4.59), 4.061 (5.40), 4.333 (5.36), 4.362 (4.47), 4.392 (0.52), 4.420 (0.44), 7.305 (1.32), 7.308 (1.37), 7.318 (1.53), 7.322 (1.56), 7.474 (0.57), 7.488 (2.76), 7.502 (2.35), 8.140 (0.56), 8.407 (2.61), 8.411 (2.53).

[0397] Intermediate 13A (rac)-1-[3-(5-chloropyridin-2-yl)pyrazin-2-yl]ethan-1-ol [ka]

[0398] According to general synthetic method 2, 410 mg (purity 96%, yield 17%) of the title compound was obtained from (rac)-1-(3-bromopyrazin-2-yl)ethan-1-ol (2.00 g, 9.85 mmol) and 2-(5-chloropyridin-2-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (Intermediate 10A, 3.31 g, purity 96%, 11.8 mmol).

[0399] LC-MS (Method 9): R t = 0.72 min; MS (ESIpos): m / z = 236 [M+H] + 1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.439 (5.75), 1.449 (5.77), 3.289 (16.00), 5.164 (1.86), 5.175 (2.20), 5.283 (0.97), 5.294 (1.39), 5.304 (0.88), 8.005 (1.56), 8.019 (1.94), 8.132 (1.18), 8.136 (1.20), 8.146 (0.99), 8.150 (0.99), 8.666 (1.85), 8.670 (2.07), 8.728 (2.02), 8.732 (1.83), 8.771 (1.74), 8.775 (1.72).

[0400] Intermediate 14A (rac)-1-{3-[5-(trifluoromethyl)pyridin-2-yl]pyrazin-2-yl}ethan-1-ol [ka]

[0401] According to general synthetic method 2, 736 mg (purity 98%, yield 35%) of the title compound was obtained from (rac)-1-(3-bromopyrazin-2-yl)ethan-1-ol (1.55 g, 7.63 mmol) and 6-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]-1,3,6,2-dioxazaborocane-4,8-dione (Intermediate 11A, 2.65 g, 8.78 mmol).

[0402] LC-MS (Method 2): R t = 1.46 min; MS (ESIpos): m / z = 270 [M+H] + 1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.463 (16.00), 1.474 (16.00), 4.337 (0.42), 5.296 (1.07), 5.307 (3.14), 5.318 (3.12), 5.328 (1.05), 8.175 (2.20), 8.189 (2.47), 8.412 (2.79), 8.415 (2.76), 8.426 (2.55), 8.428 (2.50), 8.713 (3.36), 8.780 (3.42), 9.116 (3.28).

[0403] Intermediate 15A (rac)-1-[3-(5-methoxypyridin-2-yl)pyrazin-2-yl]ethan-1-ol [ka]

[0404] According to general synthetic method 2, 480 mg (100% purity, 44% yield) of the title compound was obtained from (rac)-1-(3-bromopyrazin-2-yl)ethan-1-ol (961 mg, 4.73 mmol) and 2-(5-methoxypyridin-2-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (Intermediate 12A, 1.50 g, 5.68 mmol).

[0405] LC-MS (Method 2): R t = 1.12 min; MS (ESIpos): m / z = 232 [M+H] + 1H-NMR (500 MHz, DMSO-d6) δ [ppm]: 1.434 (6.13), 1.447 (6.14), 3.824 (0.47), 3.927 (16.00), 5.244 (0.96), 5.256 (1.47), 5.269 (0.99), 5.504 (2.39), 5.517 (2.16), 7.614 (1.28), 7.620 (1.29), 7.632 (1.38), 7.638 (1.39), 8.016 (2.04), 8.033 (1.85), 8.439 (1.91), 8.444 (1.84), 8.633 (2.32), 8.638 (3.22), 8.659 (2.97), 8.664 (2.08).

[0406] Intermediate 16A (rac)-2-{1-[3-(5-chloropyridin-2-yl)pyrazin-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione [ka]

[0407] Following general synthetic method 3, (rac)-1-[3-(5-chloropyridin-2-yl)pyrazin-2-yl]ethan-1-ol (Intermediate 13A, 410 mg, 1.74 mmol) gave 458 mg (100% purity, 72% yield) of the title compound.

[0408] LC-MS (Method 2): R t = 1.91 min; MS (ESIpos): m / z = 365 [M+H] + 1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.171 (0.62), 1.187 (0.72), 1.201 (0.57), 1.217 (0.50), 1.709 (15.98), 1.727 (16.00), 1.739 (0.74), 1.757 (0.48), 2.072 (0.99), 6.275 (1.08), 6.292 (4.05), 6.310 (4.02), 6.327 (1.07), 7.726 (4.85), 7.733 (5.58), 7.740 (4.92), 7.747 (9.26), 7.757 (1.56), 7.778 (2.12), 7.788 (9.71), 7.797 (5.84), 7.801 (9.05), 7.809 (5.73), 7.821 (5.58), 7.830 (0.77), 7.924 (4.64), 7.931 (4.68), 7.946 (3.38), 7.952 (3.50), 8.571 (3.68), 8.577 (3.67), 8.698 (15.93), 8.704 (2.65).

[0409] Intermediate 17A (rac)-2-[1-{3-[5-(trifluoromethyl)pyridin-2-yl]pyrazin-2-yl}ethyl]-1H-isoindole-1,3(2H)-dione [ka]

[0410] Following general synthetic method 3, (rac)-1-{3-[5-(trifluoromethyl)pyridin-2-yl]pyrazin-2-yl}ethan-1-ol (Intermediate 14A, 736 mg, 2.73 mmol) gave 897 mg (100% purity, 82% yield) of the title compound.

[0411] LC-MS (Method 2): R t = 1.99 min; MS (ESIpos): m / z = 399 [M+H] + .

[0412] Intermediate 18A (rac)-2-{1-[3-(5-methoxypyridin-2-yl)pyrazin-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione [ka]

[0413] Following general synthetic method 3, (rac)-1-[3-(5-methoxypyridin-2-yl)pyrazin-2-yl]ethan-1-ol (Intermediate 15A, 230 mg, 1.00 mmol) gave 325 mg (97% purity, 88% yield) of the title compound.

[0414] LC-MS (Method 2): R t = 1.65 min; MS (ESIpos): m / z = 361 [M+H] + 1 H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.164 (0.74), 1.176 (2.18), 1.188 (2.01), 1.709 (6.41), 1.721 (6.32), 1.988 (1.52), 3.820 (16.00), 6.399 (0.46), 6.411 (1.51), 6.423 (1.49), 6.435 (0.44), 7.399 (1.31), 7.404 (1.33), 7.414 (1.41), 7.419 (1.40), 7.550 (0.84), 7.555 (0.69), 7.562 (0.69), 7.567 (0.58), 7.606 (0.87), 7.611 (0.49), 7.618 (0.69), 7.625 (1.26), 7.639 (0.82), 7.741 (1.97), 7.746 (2.26), 7.750 (2.33), 7.755 (3.40), 7.762 (0.55), 7.781 (0.63), 7.788 (3.47), 7.793 (2.38), 7.797 (2.30), 7.802 (2.07), 7.807 (2.62), 7.822 (2.27), 8.259 (2.29), 8.263 (2.25), 8.588 (2.48), 8.592 (2.89), 8.631 (2.64), 8.635 (2.25).

[0415] Intermediate 19A (rac)-1-[3-(5-chloropyridin-2-yl)pyrazin-2-yl]ethan-1-amine [ka]

[0416] Following general procedure 4, (rac)-2-{1-[3-(5-chloropyridin-2-yl)pyrazin-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione (Intermediate 16A, 457 mg, 1.25 mmol) gave 285 mg (100% purity, 97% yield) of the title compound.

[0417] LC-MS (Method 2): R t = 0.69 min; MS (ESIpos): m / z = 235 [M+H] + 1 H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.178 (1.08), 1.188 (1.03), 1.235 (0.56), 1.335 (15.63), 1.346 (16.00), 1.542 (0.57), 1.554 (0.54), 3.239 (2.07), 4.581 (0.99), 7.880 (0.43), 7.995 (9.27), 8.009 (11.43), 8.061 (0.42), 8.070 (0.50), 8.127 (7.67), 8.131 (7.76), 8.141 (6.36), 8.146 (6.35), 8.633 (4.91), 8.667 (0.45), 8.671 (0.50), 8.724 (2.87), 8.769 (10.46), 8.773 (10.19).

[0418] Intermediate 20A (rac)-1-{3-[5-(trifluoromethyl)pyridin-2-yl]pyrazin-2-yl}ethan-1-amine [ka]

[0419] Following General Procedure 4, (rac)-2-[1-{3-[5-(trifluoromethyl)pyridin-2-yl]pyrazin-2-yl}ethyl]-1H-isoindole-1,3(2H)-dione (Intermediate 17A, 895 mg, 2.25 mmol) gave 600 mg (94% purity, 94% yield) of the title compound.

[0420] LC-MS (Method 2): R t = 0.83 min; MS (ESIpos): m / z = 269 [M+H] + 1 H-NMR (400 MHz, DMSO-d6) δ [ppm]: -0.149 (0.45), 0.146 (0.47), 1.150 (0.53), 1.157 (0.64), 1.174 (1.96), 1.188 (1.70), 1.338 (15.76), 1.355 (16.00), 1.988 (1.27), 2.082 (1.11), 2.710 (0.40), 4.485 (0.83), 4.502 (2.44), 4.518 (2.42), 4.534 (0.82), 8.166 (3.45), 8.187 (4.18), 8.410 (2.44), 8.416 (2.48), 8.431 (2.19), 8.436 (2.21), 8.664 (5.15), 8.669 (5.67), 8.767 (5.57), 8.773 (5.03), 9.121 (3.56), 9.123 (3.60).

[0421] Intermediate 21A (rac)-1-[3-(5-methoxypyridin-2-yl)pyrazin-2-yl]ethan-1-amine [ka]

[0422] Following general procedure 4, (rac)-2-[1-{3-[5-(methoxy)pyridin-2-yl]pyrazin-2-yl}ethyl]-1H-isoindole-1,3(2H)-dione (Intermediate 18A, 325 mg, 0.90 mmol) gave 220 mg (60% purity, 64% yield) of the title compound.

[0423] LC-MS (Method 2): R t = 0.60 min; MS (ESIpos): m / z = 321 [M+H] + .

[0424] Intermediate 22A (rac)-1-(3-bromopyrazin-2-yl)ethan-1-ol [ka]

[0425] A solution of 2,2,6,6-tetramethylpiperidine (21 mL, 120 mmol) in THF (260 mL) was cooled to −78°C. A solution of n-butyllithium (2.5 M in hexanes, 48 ​​mL, 120 mmol) was slowly added, and stirring was maintained at −78°C for 30 minutes. 2-Bromopyrazine (8.5 mL, 94 mmol) was then added dropwise, maintaining the temperature at −70°C. Stirring was continued at −78°C for 1 hour. Acetaldehyde (11 mL, 190 mmol) was added dropwise, the cooling bath was removed, and the mixture was allowed to warm slowly to room temperature. The reaction mixture was poured into water (500 mL), acidified with 1 M hydrochloric acid, and extracted six times with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, the solvent was carefully distilled off on a rotary evaporator (bath temperature 40°C, 140 mbar) and finally purified by silica gel flash chromatography using a cyclohexane-ethyl acetate gradient to give 12.6 g (61% of theory) of the title compound.

[0426] LC-MS (Method 2): R t = 0.81 min; MS (ESIpos): m / z = 203 [M+H] + 1 H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.164 (2.79), 1.176 (5.67), 1.187 (2.84), 1.407 (15.63), 1.418 (16.00), 1.907 (0.49), 1.987 (10.52), 4.013 (0.83), 4.025 (2.50), 4.037 (2.49), 4.049 (0.82), 5.076 (0.53), 5.087 (2.14), 5.097 (3.28), 5.108 (2.23), 5.119 (0.58), 5.353 (5.76), 5.363 (5.33), 5.744 (1.31), 8.400 (4.78), 8.404 (4.96), 8.670 (4.87), 8.674 (4.75).

[0427] Intermediate 23A (rac)-2-[1-(3-bromopyrazin-2-yl)ethyl]-1H-isoindole-1,3(2H)-dione [ka]

[0428] Following general synthetic method 3, (rac)-1-(3-bromopyrazin-2-yl)ethan-1-ol (Intermediate 22A, 10.0 g, 49.3 mmol) gave 12.8 g (98% purity, 77% yield).

[0429] LC-MS (Method 2): R t = 1.75 min; MS (ESIpos): m / z = 332 [M+H] + 1 H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.179 (0.88), 1.189 (0.84), 1.786 (5.16), 1.798 (5.17), 5.655 (1.17), 5.667 (1.14), 7.867 (16.00), 8.452 (1.85), 8.457 (1.83), 8.708 (2.09), 8.712 (1.94).

[0430] Intermediate 24A (rac)-Methyl 6-{3-[-1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]pyrazin-2-yl}pyridine-3-carboxylate [ka]

[0431] Solution A - [5-(methoxycarbonyl)pyridin-2-yl]zinc chloride in THF: In a flame-dried three-necked round-bottom flask, methyl 6-iodopyridine-3-carboxylate (1.88 g, 7.15 mmol) was suspended in THF (8.0 mL) and then cooled to -30 °C. A solution of isopropylmagnesium chloride x lithium chloride (1.3 M in THF, 7.1 mL, 9.3 mmol) was added dropwise, and the mixture was stirred for 5 minutes. Zinc dichloride (4.5 mL, 1.9 M in methyl-THF, 8.6 mmol) was then added. This solution was then used directly in the cross-coupling reaction.

[0432] To this end, (rac)-2-[-(3-bromopyrazin-2-yl)ethyl]-1H-isoindole-1,3(2H)-dione (Intermediate 23A, 780 mg, 2.34 mmol) and 1,1-bis(diphenylphosphino)-ferrocenedichloropalladium(II) (192 mg, 234 μmol) were placed in two separate microwave reactor vials under argon, solution A was added, and the mixture was heated to 110° C. for 90 min in a single-mode microwave. After cooling, the mixture was loaded onto silica gel, evaporated, and then purified by flash chromatography using a cyclohexane-ethyl acetate gradient to give 97.0 mg (97% purity, 11% yield) of the title compound.

[0433] LC-MS (Method 9): R t = 0.92 min; MS (ESIpos): m / z = 389 [M+H] + 1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.719 (4.11), 1.731 (4.05), 2.069 (0.45), 3.289 (16.00), 3.901 (9.08), 3.934 (0.75), 6.306 (1.05), 6.318 (1.04), 7.690 (1.45), 7.696 (1.59), 7.699 (1.63), 7.705 (1.97), 7.764 (2.09), 7.769 (1.71), 7.773 (1.54), 7.778 (1.40), 7.912 (1.49), 7.926 (1.61), 8.247 (0.99), 8.250 (0.93), 8.260 (0.92), 8.264 (0.85), 8.726 (2.04), 8.738 (2.11), 8.742 (1.29), 8.985 (1.57), 8.987 (1.53).

[0434] Intermediate 25A (rac)-Methyl 6-{3-[1-aminoethyl]pyrazin-2-yl}pyridine-3-carboxylate [ka]

[0435] Following general synthetic method 4, (rac)-methyl 6-{3-[1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]pyrazin-2-yl}pyridine-3-carboxylate (Intermediate 24A, 160 mg, 412 μmol) gave 115 mg (79% purity, 85% yield).

[0436] LC-MS (Method 2): R t = 0.76 min; MS (ESIpos): m / z = 259 [M+H] + .

[0437] Intermediate 26A (rac)-(6-{3-[1-aminoethyl]pyrazin-2-yl}pyridin-3-yl)(morpholin-4-yl)methanone [ka]

[0438] LC-MS (Method 2): R t = 0.46 min; MS (ESIpos): m / z = 314 [M+H] + .

[0439] Intermediate 27A (rac)-Methyl 2-{3-[1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]pyrazin-2-yl}-1,3-thiazole-5-carboxylate [ka]

[0440] Solution A: Methyl 2-bromo-1,3-thiazole-5-carboxylate (2.00 g, 9.00 mmol) was dissolved in THF (9.0 mL). The mixture was cooled to -40 °C, and isopropyl magnesium chloride x lithium chloride (8.3 mL, 1.3 M in THF, 11 mmol) was added. The temperature was adjusted to -70 °C, and a solution of zinc dichloride (5.2 mL, 1.9 M in methyl-THF, 9.9 mmol) was added while maintaining the temperature within the range of -50 to -70 °C. This solution was used immediately i...

Claims

1. General formula (I) 【Chemistry 1】 [During the ceremony, R １ is hydrogen; or optionally substituted C １ -C ６ Alkyl, C ３ -C ６ Cycloalkyl C １ -C ６ Alkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Alkini Lu, C １ -C ６ Alkoxy C １ -C ６ Alkyl, C １ -C ６ Alkylthio C １ -C ６ Al Kill, C １ -C ６ Alkylsulfinyl C １ -C ６ Alkyl, C １ -C ６ Alkyl sulfonate Nil C １ -C ６ alkyl [wherein the optionally substituted radical is halogen, hydroxy, —CN, —NO ２ , -Si(CH ３ ) ３ , -NH ２ and C １ -C ６ and optionally substituted with up to three substituents independently selected from the group consisting of alkyl; 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, C １ -C ３ and optionally substituted with 1 to 5 substituents independently selected from the group consisting of cyanoalkylsulfonyl; Or, Heterocyclyl-C １ -C ３ alkyl, wherein the heterocyclyl is selected from the group consisting of tetrahydropyranyl, tetrahydrofuranyl, oxetanyl, and azetidinyl, or heteroaryl, wherein the heteroaryl is selected from the group consisting of pyridyl, pyrimidinyl, pyrazyl, pyridazinyl, thiophenyl, furanyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl, and oxazolyl, and wherein the heteroaryl or the heterocyclyl is selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH ２ , -CSNH ２ , -NO ２ , -Si(CH ３ ) ３ , S.F. 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, C １ -C ３ and cyanoalkylsulfonyl. and R ２ is selected from the group consisting of phenyl, pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, and thiophene, each of which is optionally substituted with one, two, or three substituents independently selected from the group consisting of: Halogen, hydroxy, -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 ３ Haloalkyl, C １ -C ４ Alkoxy, C ３ -C ６ Cycloalkoxy, C １ -C ３ Haloalkoxy, hydroxy-C １ -C ４ Alkyl, —CO ２ C １ -C ４ Alkyl, —NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -C(=NOC １ -C ４ alkyl)H, -C(=NOC １ -C ４ alkyl)-C １ -C ４ Alkyl and (C １ -C ４ alkyl) ３ -silyl [wherein the optionally substituted radical is halogen, hydroxy, -CN, -NO ２ , -Si(CH ３ ) ３ , -NH ２ , C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ Cycloalkyl, C ３ -C ４ Halocycloalkyl, C １ -C ３ Alkylsulfonyl, C ３ -C ４ Cycloalkylsulfonyl, C １ -C ３ Haloalkylthio and C １ -C ３ and optionally substituted with up to three substituents independently selected from the group consisting of haloalkylsulfonyl; and, Structures S1, S4, S7, S8 and S9 【Chemistry 4】 wherein the bond to the phenyl, pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole or thiophene is marked with a #, and Z is CO or CS; R ２１ is hydrogen or, in either case, optionally substituted C １ -C ４ Alkyl, C １ -C ４ Haloalkyl, C ３ -C ６ Cycloalkyl, —C １ -C ４ Alkyl-C ３ -C ６ cycloalkyl and 3-6 membered heterocyclyl; R ２２ is hydrogen or, in either case, optionally substituted C １ -C ４ Alkyl, C １ -C ４ Haloalkyl, —C １ -C ４ Alkyl-C ３ -C ６ Cycloalkyl and C ３ -C ６ is cycloalkyl; R ２４ is optionally substituted C １ -C ４ Alkyl, C ２ -C ６ Alkenyl, C ２ -C ６ Alkynyl, C １ -C ４ Haloalkyl, C ３ -C ６ cycloalkyl, phenyl, heteroaryl, and 3- to 6-membered heterocyclyl; Here, R ２１ , R ２２ and R ２４ The optionally substituted radicals in the definition of ２ , -Si(CH ３ ) ３ , -NH ２ , C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ Cycloalkyl, C ３ -C ４ Halocycloalkyl, C １ -C ４ Alkoxy, C １ -C ４ Haloalkoxy, C １ -C ３ Alkylsulfonyl, C ３ -C ４ Cycloalkylsulfonyl, C １ -C ３ Haloalkylthio and C １ -C ３ and optionally substituted with up to three substituents independently selected from the group consisting of haloalkylsulfonyl; Or, R ２１ and R ２２ together with the nitrogen atom to which they are attached form a 4- to 12-membered saturated or unsaturated heterocyclyl, wherein the heterocyclyl can contain up to two additional heteroatoms selected from the group of oxygen, nitrogen, and sulfur, and wherein the heterocyclyl is selected from halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —NO ２ , -SF ５ and -NH ２ and C １ -C ４ Alkyl, C ３ -C ６ Cycloalkyl, C １ -C ４ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ４ Haloalkoxy, C １ -C ４ Alkylthio, C １ -C ４ Alkylsulfinyl, C １ -C ４ Alkylsulfonyl, C ３ -C ６ Cycloalkylsulfanyl, C ３ -C ６ Cycloalkylsulfinyl, C ３ -C ６ Cycloalkylsulfonyl, C １ -C ４ Haloalkylthio, C １ -C ４ Haloalkylsulfinyl, C １ -C ４ haloalkylsulfonyl, optionally substituted with 1 to 3 substituents selected from the group consisting of: 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, —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 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 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]; R ３ is 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 ４ optionally substituted with alkoxy; R ４ is selected from the group consisting of pyridine, pyrimidine, pyrazine and pyridazine, each of which is substituted with one, two or three substituents independently selected from the group consisting of: ・ -COOH、-NO ２ 、-NH ２ 、-SF ５ ; and, C, which may in any case be substituted ２ -C ６ Alkenyl, C ２ -C ６ Alkynyl, C ３ -C ６ Cycloalkoxy, hydroxy-C １ -C ４ Alkyl, —CO ２ C １ -C ４ Alkyl, —NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -C(=NOC １ -C ４ alkyl)H and -C(=NOC １ -C ４ alkyl)-C １ -C ４ alkyl [wherein the optionally substituted radical is halogen, hydroxy, —CN, —NO ２ , -Si(CH ３ ) ３ , -NH ２ , C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ Cycloalkyl, C ３ -C ４ Halocycloalkyl, C １ -C ４ Alkoxy, C １ -C ４ Haloalkoxy, C １ -C ３ Alkylsulfonyl, C ３ -C ４ Cycloalkylsulfonyl, C １ -C ３ Haloalkylthio and C １ -C ３ and optionally substituted with up to three substituents independently selected from the group consisting of haloalkylsulfonyl; and, Structures S10, S11, S13, S14, S16, S17 and S18 【Transformation 5】 wherein the bond to the pyridine, pyrimidine, pyrazine or pyridazine is marked with a #, and Z is CO or CS; R ４１ is hydrogen or, in either case, optionally substituted C １ -C ４ Alkyl, C １ -C ４ Haloalkyl, C ３ -C ６ Cycloalkyl, —C １ -C ４ Alkyl-C ３ -C ６ cycloalkyl and 3-6 membered heterocyclyl; R ４２ is hydrogen or, in either case, optionally substituted C １ -C ４ Alkyl, C １ -C ４ Haloalkyl, —C １ -C ４ Alkyl-C ３ -C ６ Cycloalkyl and C ３ -C ６ is cycloalkyl; R ４３ is optionally substituted C １ -C ４ Alkyl, C １ -C ４ Haloalkyl and C ３ -C ６ independently selected from cycloalkyl; R ４４ is optionally substituted C １ -C ４ Alkyl, C １ -C ４ Haloalkyl, C ３ -C ６ cycloalkyl, phenyl, heteroaryl, and 3- to 6-membered heterocyclyl; Here, R ４１ , R ４２ , R ４３ and R ２４ The optionally substituted radicals in the definition of ２ , -Si(CH ３ ) ３ , -NH ２ , C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ Cycloalkyl, C ３ -C ４ Halocycloalkyl, C １ -C ４ Alkoxy, C １ -C ４ Haloalkoxy, C １ -C ３ Alkylsulfonyl, C ３ -C ４ Cycloalkylsulfonyl, C １ -C ３ Haloalkylthio and C １ -C ３ and optionally substituted with up to three substituents independently selected from the group consisting of haloalkylsulfonyl; Or, R ４１ and R ４２ together with the nitrogen atom to which they are attached form a 4- to 12-membered saturated or unsaturated heterocyclyl, wherein the heterocyclyl can contain up to two additional heteroatoms selected from the group of oxygen, nitrogen, sulfur, and silicon, and the heterocyclyl can be selected from halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —NO ２ , -SF ５ and -NH ２ and C １ -C ４ Alkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cycloalkyl-C １ -C ６ Alkyl, C １ -C ４ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ４ Haloalkoxy, C １ -C ４ Alkoxy-C １ -C ６ Alkyl, C １ -C ４ Alkylthio, C １ -C ４ Alkylsulfinyl, C １ -C ４ Alkylsulfonyl, C ３ -C ６ Cycloalkylsulfanyl, C ３ -C ６ Cycloalkylsulfinyl, C ３ -C ６ Cycloalkylsulfonyl, C １ -C ４ Haloalkylthio, C １ -C ４ Haloalkylsulfinyl, C １ -C ４ haloalkylsulfonyl, optionally substituted with 1 to 3 substituents selected from the group consisting of: 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, —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 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 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 ４ is selected from the group consisting of thiazole, pyrazole, pyrrole, oxazole, isothiazole, isoxazole, thiophene and imidazole, Each may be optionally substituted with one, two, or three substituents independently selected from the group consisting of: Halogen, hydroxy, -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 ３ Haloalkyl, C １ -C ４ Alkoxy, C ３ -C ６ Cycloalkoxy, C １ -C ３ Haloalkoxy, hydroxy-C １ -C ４ Alkyl, —CO ２ C １ -C ４ Alkyl, —NH(C １ -C ４ alkyl), -N(C １ -C ４ alkyl) ２ , -C(=NOC １ -C ４ alkyl)H, -C(=NOC １ -C ４ alkyl)-C １ -C ４ Alkyl and (C １ -C ４ alkyl) ３ -silyl [wherein the optionally substituted radical is halogen, hydroxy, -CN, -NO ２ , -Si(CH ３ ) ３ , -NH ２ , C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ Cycloalkyl, C ３ -C ４ Halocycloalkyl, C １ -C ４ Alkoxy, C １ -C ４ Haloalkoxy, C １ -C ３ Alkylsulfonyl, C ３ -C ４ Cycloalkylsulfonyl, C １ -C ３ Haloalkylthio and C １ -C ３ and optionally substituted with up to three substituents independently selected from the group consisting of haloalkylsulfonyl; and, Structures S10, S11, S13, S14, S16, S17 and S18 【Transformation 5】 wherein the bond to the thiazole, pyrazole, pyrrole, oxazole, isothiazole, isoxazole, thiophene or imidazole is marked with a #, and Z is CO or CS; R ４１ is hydrogen or, in either case, optionally substituted C １ -C ４ Alkyl, C １ -C ４ Haloalkyl, C ３ -C ６ Cycloalkyl, —C １ -C ４ Alkyl-C ３ -C ６ cycloalkyl and 3-6 membered heterocyclyl; R ４２ is hydrogen or, in either case, optionally substituted C １ -C ４ Alkyl, C １ -C ４ Haloalkyl, —C １ -C ４ Alkyl-C ３ -C ６ Cycloalkyl and C ３ -C ６ is cycloalkyl; R ４３ is optionally substituted C １ -C ４ Alkyl, C １ -C ４ Haloalkyl and C ３ -C ６ independently selected from cycloalkyl; R ４４ is optionally substituted C １ -C ４ Alkyl, C １ -C ４ Haloalkyl, C ３ -C ６ cycloalkyl, phenyl, heteroaryl, and 3- to 6-membered heterocyclyl; Here, R ４１ , R ４２ , R ４３ and R ２４ The above-mentioned optionally substituted groups in the definition of Dichlor is halogen, hydroxy, -CN, -NO ２ , -Si(CH ３ ) ３ , -NH ２ , C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ Cycloalkyl, C ３ -C ４ Halocycloalkyl, C １ -C ４ Alkoxy, C １ -C ４ Haloalkoxy, C １ -C ３ Alkylsulfonyl, C ３ -C ４ Cycloalkylsulfonyl, C １ -C ３ Haloalkylthio and C １ -C ３ and optionally substituted with up to three substituents independently selected from the group consisting of haloalkylsulfonyl; Or, R ４１ and R ４２ together with the nitrogen atom to which they are attached form a 4- to 12-membered saturated or unsaturated heterocyclyl, wherein the heterocyclyl can contain up to two additional heteroatoms selected from the group of oxygen, nitrogen, sulfur, and silicon, and the heterocyclyl can be selected from halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —NO ２ , -SF ５ and -NH ２ and C １ -C ４ Alkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Cycloalkyl-C １ -C ６ Alkyl, C １ -C ４ Haloalkyl, C １ -C ４ Alkoxy, C １ -C ４ Haloalkoxy, C １ -C ４ Alkoxy-C １ -C ６ Alkyl, C １ -C ４ Alkylthio, C １ -C ４ Alkylsulfinyl, C １ -C ４ Alkylsulfonyl, C ３ -C ６ Cycloalkylsulfanyl, C ３ -C ６ Cycloalkylsulfinyl, C ３ -C ６ Cycloalkylsulfonyl, C １ -C ４ Haloalkylthio, C １ -C ４ Haloalkylsulfinyl, C １ -C ４ haloalkylsulfonyl, optionally substituted with 1 to 3 substituents selected from the group consisting of: 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, —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 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 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]; R ５ is hydrogen, halogen, -CN, NH ２ or optionally substituted C in either case １ -C ３ -Alkyl, C ３ -C ４ -cycloalkyl, C １ -C ３ Alkoxy, —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, or -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 ３ -C ６ Cycloalkylthio [wherein the optionally substituted radical is halogen, hydroxy, —CN, —NO ２ , -Si(CH ３ ) ３ , -NH ２ and C １ -C ３ and optionally substituted with up to three substituents independently selected from the group consisting of alkyl; R ６ is hydrogen, halogen, -CN, NH ２ or optionally substituted C in either case １ -C ３ -Alkyl, C ３ -C ４ -cycloalkyl, C １ -C ３ Alkoxy, —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, or -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 ３ -C ６ Cycloalkylthio [wherein the optionally substituted radical is halogen, hydroxy, —CN, —NO ２ , -Si(CH ３ ) ３ , -NH ２ and C １ -C ３ and optionally substituted with up to three substituents independently selected from the group consisting of alkyl. and salts and N-oxides thereof.

2. R １ is hydrogen; or C １ -C ６ Alkyl, 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 Haloalkynyl, 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, C １ -C ３ Alkylsulfonyl C １ -C ３ Alkyl, C １ -C ６ Haloalkyl, C １ -C ６ is cyanoalkyl; R ２ is selected from the group consisting of pyrazole, phenyl, pyridine, pyrimidine, pyrazine and pyridazine, each of which is optionally substituted with a total of 1, 2 or 3 substituents, wherein any 1, 2 or 3 of the substituents are independently selected from Group A consisting of: Halogen, hydroxy, -CN, -COOH, -NO ２ , -NH ２ , -SF ５ ; and, ・C １ -C ４ Alkyl, C １ -C ３ Haloalkyl, C １ -C ３ Cyanoalkyl, C ３ -C ４ Cycloalkyl, C ３ -C ４ Halocycloalkyl, C ３ -C ４ Cyanocycloalkyl, C １ -C ３ Alkoxy, C １ -C ３ Haloalkoxy, C ３ -C ４ Cycloalkoxy, C １ -C ３ Cyanoalkoxy and —CO ２ C １ -C ４ Alkyl; And, optionally, one of the optional substituents may be selected from Group B consisting of: Structures S1, S4, S7, S8 and S9 【Transformation 6】 wherein the bond to the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is marked with a # and Z is CO; R ２１ is hydrogen or, in either case, optionally substituted C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ is cycloalkyl; R ２２ is hydrogen or, in either case, optionally substituted C １ -C ３ Alkyl, C １ -C ３ Haloalkyl and C ３ -C ４ is cycloalkyl; R ２４ is optionally substituted C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ cycloalkyl and phenyl; Here, R ２１ , R ２２ and R ２４ The optionally substituted radical in the definition of ２ , -Si(CH ３ ) ３ , C １ -C ３ Alkyl, C １ -C ３ and optionally substituted with up to three substituents independently selected from the group consisting of haloalkyl; R ３ is C １ -C ６ is alkyl; R ４ is selected from the group consisting of pyridine, pyrimidine, pyrazine and pyridazine, wherein said 6-membered heteroaryl is each substituted with 1, 2 or 3 substituents, wherein in each case up to all of said optional substituents are independently selected from group D consisting of: ・ -COOH、-NO ２ 、-NH ２ 、-SF ５ ; and, ・C １ -C ３ Cyanoalkyl, C ３ -C ４ Cyanocycloalkyl, C ３ -C ４ Cycloalkoxy, C １ -C ３ Cyanoalkoxy, hydroxy-C １ -C ３ Alkyl, —CO ２ C １ -C ３ Alkyl, —NH(C １ -C ３ alkyl), -N(C １ -C ３ alkyl) ２ , -C(=NOC １ -C ３ alkyl)H, -C(=NOC １ -C ３ alkyl)-C １ -C ３ Alkyl and (C １ -C ３ alkyl) ３ - Cyril; And, optionally, one of the optional substituents may be selected from Group E consisting of: Structures S10, S13, S16, S17 and S18 【Transformation 7】 wherein the bond to the pyridine, pyrimidine, pyrazine or pyridazine is marked with a # and Z is CO; R ４１ is hydrogen or, in either case, optionally substituted C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ Cycloalkyl, —C １ -C ２ Alkyl-C ３ -C ４ cycloalkyl and 3-6 membered heterocyclyl, wherein the heterocyclyl contains one heteroatom selected from the group consisting of N, O, and S; R ４２ is hydrogen or, in either case, optionally substituted C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, —C １ -C ２ Alkyl-C ３ -C ４ Cycloalkyl and C ３ -C ４ is cycloalkyl; R ４４ is optionally substituted C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ is cycloalkyl; Here, R ４１ , R ４２ and R ４４ The optionally substituted substituents defined for ２ , -Si(CH ３ ) ３ , C １ -C ３ Alkyl, C １ -C ３ and optionally substituted with up to two substituents independently selected from the group consisting of haloalkyl; Or, R ４１ and R ４２ together with the nitrogen atom to which they are attached form a monocyclic 4- to 8-membered saturated heterocyclyl, which may contain up to one additional heteroatom selected from the group of oxygen, nitrogen, sulfur, and silicon, and which heterocyclyl is selected from halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —NO ２ and -NH ２ and C １ -C ３ Alkyl, C ３ -C ４ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ３ Alkoxy, C １ -C ３ haloalkoxy); Or, R ４ is selected from the group consisting of pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene and imidazole, wherein the 5-membered heteroaryl is each optionally substituted with 1 or 2 substituents, wherein in each case up to all of the optional substituents are independently selected from group D consisting of: Halogen, hydroxy, -CN, -COOH, -NO ２ , -NH ２ , -SF ５ ; and, ・C １ -C ３ Alkyl, C ３ -C ４ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ３ Cyanoalkyl, C ３ -C ４ Cyanocycloalkyl, C １ -C ３ Alkoxy, C ３ -C ４ Cycloalkoxy, C １ -C ３ Haloalkoxy, C １ -C ３ Cyanoalkoxy, hydroxy-C １ -C ３ Alkyl, —CO ２ C １ -C ３ Alkyl, —NH(C １ -C ３ alkyl), -N(C １ -C ３ alkyl) ２ , -C(=NOC １ -C ３ alkyl)H, -C(=NOC １ -C ３ alkyl)-C １ -C ３ Alkyl and (C １ -C ３ alkyl) ３ - Cyril; And, optionally, one of the optional substituents may be selected from Group E consisting of: Structures S10, S13, S16, S17 and S18 【Transformation 7】 wherein the bond to the thiazole, pyrazole, pyrrole, oxazole, isothiazole, isoxazole, thiophene, or imidazole is marked with a #, and Z is CO; R ４１ is hydrogen or, in either case, optionally substituted C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ Cycloalkyl, —C １ -C ２ Alkyl-C ３ -C ４ cycloalkyl and 3-6 membered heterocyclyl, wherein the heterocyclyl contains one heteroatom selected from the group consisting of N, O, and S; R ４２ is hydrogen or, in either case, optionally substituted C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, —C １ -C ２ Alkyl-C ３ -C ４ Cycloalkyl and C ３ -C ４ is cycloalkyl; R ４４ is optionally substituted C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ is cycloalkyl; Here, R ４１ , R ４２ and R ４４ The optionally substituted substituents defined for ２ , -Si(CH ３ ) ３ , C １ -C ３ Alkyl, C １ -C ３ and optionally substituted with up to two substituents independently selected from the group consisting of haloalkyl; Or, R ４１ and R ４２ together with the nitrogen atom to which they are attached form a monocyclic 4- to 8-membered saturated heterocyclyl, which may contain up to one additional heteroatom selected from the group of oxygen, nitrogen, sulfur, and silicon, and which heterocyclyl is selected from halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —NO ２ and -NH ２ and C １ -C ３ Alkyl, C ３ -C ４ Cycloalkyl, C １ -C ３ Haloalkyl, C １ -C ３ Alkoxy, C １ -C ３ haloalkoxy); R ５ is hydrogen, halogen, -CN, C １ -C ３ -Alkyl, C １ -C ３ -haloalkyl, C ３ -C ４ -cycloalkyl, C １ -C ３ Alkoxy, C １ -C ３ haloalkoxy; R ６ is hydrogen, halogen, -CN, C １ -C ３ -Alkyl, C １ -C ３ -haloalkyl, C ３ -C ４ Cycloalkyl, C １ -C ３ Alkoxy, C １ -C ３ haloalkoxy; The compound of claim 1, and its salts and N-oxides.

3. R １ is hydrogen; methyl, ethyl, n-propyl, isopropyl, cyanomethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, methylsulfonylethyl, ethylsulfonylethyl; R ２ is selected from the group consisting of pyrazole, phenyl, and pyridine, where each of these is selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxy, —CN, —COOH, —NO ２ , -NH ２ , -SF ５ , methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, cyclobutyl, 1-cyanocyclopropyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, 1-cyano-1-methyleth-1-yl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, cyanomethoxy, methylthio, methylsulfinyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, (CH ３ ) ３ - optionally substituted with 1 or 2 substituents independently selected from the group consisting of silyl, phenylsulfonyl (which may have fluorine, chlorine or methyl substituents); R ３ is methyl, ethyl, n-propyl or isopropyl; R ４ is selected from the group consisting of pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, and pyrazin-3-yl, wherein these are selected from the group consisting of -COOH, cyanomethyl, cyanomethoxy, methylthio, methylsulfinyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, -COOCH ３ , -COOCH ２ CH ３ , and structure S13 【Transformation 8】 [wherein the above-mentioned pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl or The bond to the pyrazin-3-yl is marked with # and Z is CO; R ４１ is hydrogen, methyl, ethyl, n-propyl, propan-2-yl, butan-2-yl, 2,2,2-trifluoroethyl, 2-trifluoromethoxyethyl, cyanomethyl, cyclopropyl, cyclopropylmethyl or 2-methyl-n-propyl; R ４２ is hydrogen, methyl, ethyl, n-propyl, propan-2-yl, butan-2-yl, 2,2,2-trifluoroethyl, 2-trifluoromethoxyethyl, cyanomethyl, cyclopropyl, cyclopropylmethyl or 2-methyl-n-propyl; R ４１ and R ４２ together with the nitrogen atom to which they are attached, represent pyrrolidine, piperidine, azepane, morpholine, oxazepane, azacilloridine, azasirinane, or azacilepane (each of which may be substituted with one or two methyl groups). and is substituted with one substituent selected from the group consisting of: Or, R ４ is selected from the group consisting of 1,3-thiazol-2-yl, 1,3-oxazol-2-yl, 1,2-oxazol-3-yl, 1,2-thiazol-3-yl, 1H-pyrazol-1-yl, 1H-pyrazol-3-yl and 1H-imidazol-4-yl, wherein each of these is selected from the group consisting of fluorine, chlorine, bromine, —CN, —COOH, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, cyanomethoxy, methylthio, methylsulfinyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, —COOCH ３ , -COOCH ２ CH ３ , and structure S13 【Transformation 8】 wherein the bond to the 1,3-thiazol-2-yl, 1,3-oxazol-2-yl, 1,2-oxazol-3-yl, 1,2-thiazol-3-yl, 1H-pyrazol-1-yl, 1H-pyrazol-3-yl or 1H-imidazol-4-yl is marked with a #, and Z is CO; R ４１ is hydrogen, methyl, ethyl, n-propyl, propan-2-yl, butan-2-yl, 2,2,2-trifluoroethyl, 2-trifluoromethoxyethyl, cyanomethyl, cyclopropyl, cyclopropylmethyl or 2-methyl-n-propyl; R ４２ is hydrogen, methyl, ethyl, n-propyl, propan-2-yl, butan-2-yl, 2,2,2-trifluoroethyl, 2-trifluoromethoxyethyl, cyanomethyl, cyclopropyl, cyclopropylmethyl or 2-methyl-n-propyl; R ４１ and R ４２ together with the nitrogen atom to which they are attached, represent pyrrolidine, piperidine, azepane, morpholine, oxazepane, azacilloridine, azasirinane, or azacilepane (each of which may be substituted with one or two methyl groups). and optionally substituted with one substituent selected from the group consisting of: R ５ is hydrogen, fluorine, chlorine, bromine, iodine, —CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or cyanomethoxy; R ６ is hydrogen, fluorine, chlorine, bromine, iodine, —CN, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyanomethyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or cyanomethoxy; 3. The compound according to claim 1 or 2, and its salts and N-oxides.

4. R １ is hydrogen or cyclopropylmethyl; R ２ is selected from the group consisting of pyrazole, phenyl, and pyridine, where each of these is selected from the group consisting of fluorine, chlorine, bromine, iodine, —CN, —SF ５ , methyl, ethyl, n-propyl, isopropyl, tert-butyl, 1-cyano-1-methyleth-1-yl, cyclopropyl, 1-cyanocyclopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, 4-fluorophenylsulfonyl, and difluoromethylsulfonyl; R ３ is methyl; R ４ is selected from the group consisting of pyridin-2-yl and pyrimidin-2-yl, where these are —COOH, —COOCH ３ , -COOCH ２ CH ３ , and Structure S13 【Chemistry 9】 wherein the bond marked with # is attached to the C-5 position of the pyridin-2-yl or pyrimidin-2-yl, and Z is CO; R ４１ is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl, cyclopropyl; R ４２ is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl; R ４１ and R ４２ together with the nitrogen atom to which they are attached, represent pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane or (Si,Si-dimethyl)azasilinane. and is substituted with one substituent selected from the group consisting of: Or, R ４ is selected from the group consisting of 1,3-thiazol-2-yl and 1H-pyrazol-1-yl, where these are fluorine, chlorine, bromine, —CN, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, —COOH, —COOCH ３ , -COOCH ２ CH ３ , and structure S13 【Chemistry 9】 wherein the bond marked with # is attached to the C-5 position of the 1,3-thiazol-2-yl- or the C-4 position of the 1H-pyrazol-1-yl, and Z is CO; R ４１ is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl, cyclopropyl; R ４２ is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl; R ４１ and R ４２ together with the nitrogen atom to which they are attached, represent pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane or (Si,Si-dimethyl)azasilinane. and optionally substituted with one substituent selected from the group consisting of: R ５ is hydrogen or methyl; R ６ is hydrogen or methyl; A compound according to claim 1, 2 or 3, and its salts and N-oxides.

5. R ２ is selected from the group consisting of phenyl, pyridyl, thiophene, pyrazole and imidazole, which can be substituted as defined in any one of claims 1 to 4, as well as salts and N-oxides thereof.

6. R ４ is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine, each of which is substituted as defined in any one of claims 1 to 5, as well as salts and N-oxides thereof.

7. R ４ is selected from the group consisting of thiazole, pyrazole, pyrrole, oxazole, isothiazole, isoxazole, thiophene and imidazole, each of which may be substituted as defined in any of claims 1 to 5. A compound according to any one of claims 1 to 5, and salts and N-oxides thereof.

8. R ４ is selected from the group consisting of thiazole, pyrazole, isothiazole and imidazole, each of which can be substituted as defined in any of claims 1 to 5. A compound according to any one of claims 1 to 5, and salts and N-oxides thereof.

9. R ４ is selected from the group consisting of thiazole, pyrazole, each of which can be substituted as defined in any of claims 1 to 5, A compound according to any one of claims 1 to 5, and salts and N-oxides thereof.

10. R ２ is represented by the structure Q1, where the bond to the C=O-group is marked with a #: 【Chemistry 10】 where: R ２５ is hydroxy, -NH ２ , -SO ２ NH ２ , C ４ -C ６ Alkyl, C ４ Arco Kishi, C １ -C ３ Cyanoalkyl, C ３ -C ６ Cycloalkyl, C ３ -C ６ Halocycloa Lukil, C ３ -C ６ Cyanocycloalkyl, C １ -C ３ Alkylthio, C １ -C ３ Archi Rusulfinyl, C １ -C ３ Alkylsulfonyl, C ３ -C ６ Cycloalkylsulfanyl, C ３ -C ６ Cycloalkylsulfinyl, C ３ -C ６ Cycloalkylsulfonyl, 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 3-6 membered heterocyclyl (which contains 1 or 2 heteroatoms selected from the group consisting of N, O, and S); Here, the phenyl group of the above substituents and the 3- to 6-membered heterocyclyl substituents are not limited to halogen, CN, C １ -C ６ Alkyl, C １ -C ６ Haloalkyl and C １ -C ３ cyanoalkyl; and R ２６ is a halogen, -CN, -COOH, -CONH ２ , -NO ２ , -SF ５ , C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C １ -C ３ Alkoxy, C １ -C ３ Haloal Kokisi, C. １ -C ３ Haloalkylthio, C １ -C ３ Alkylthio, C １ -C ３ Alkyls Rufinil, C １ -C ３ Alkylsulfonyl, 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, C ３ -C ６ is a cyanocycloalkyl. The compound according to any one of claims 1 to 9,

11. Formula (I-vii) to Formula (I-xix) 【Chemistry 11】 【change】 [During the ceremony, R １ , R ３ , R ５ and R ６ has the meaning defined in any of claims 1 to 9; R ７ are the same or different, and in any of claims 1 to 9, R ２ the meaning of the substituents in phenyl or 5- or 6-membered heteroaryl defined in relation to R ８ are the same or different, and in any of claims 1 to 9, R ４ has the meaning of the substituents in monocyclic heterocycles defined with respect to R ８１ is optionally substituted C １ -C ６ Alkyl, C ２ -C ６ a Alkenyl, C ２ -C ６ Alkynyl, C ３ -C ６ Cycloalkyl, C １ -C ３ Haloalkyl , hydroxy-C ２ -C ４ Alkyl, —CO ２ C １ -C ４ Alkyl, -C(=NOC １ - C ４ alkyl)H, -C(=NOC １ -C ４ alkyl)-C １ -C ４ alkyl [wherein the optionally substituted radical is halogen, hydroxy, —CN, —NO ２ , -Si(CH ３ ) ３ , -NH ２ , C １ -C ３ Alkyl, C １ -C ３ Haloalkyl, C ３ -C ４ Cycloalkyl, C ３ -C ４ Halocycloalkyl, C １ -C ４ Alkoxy, C １ -C ４ Haloalkoxy, C １ -C ３ Alkylsulfonyl, C ３ -C ４ Cycloalkylsulfonyl, C １ -C ３ Haloalkylthio and C １ -C ３ haloalkylsulfonyl; a 3- to 6-membered heterocyclyl containing one or two heteroatoms selected from the group consisting of N, O, and S, wherein the 3- to 6-membered heterocyclyl 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 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, C １ -C ３ cyanoalkylsulfonyl; n represents an integer of 0, 1 or 2; m represents an integer of 1 or 2. The compound according to any one of claims 1 to 9, characterized in that it has a structure represented by the following formula: and a salt and N-oxide thereof.

12. Formulations for controlling pests, protecting crops or controlling vectors, comprising at least one compound of formula (I) as defined in any one of claims 1 to 11, and Said formulation may comprise at least one further compound selected from fillers, surfactants, adjuvants, excipients, solvents and / or additional pharmaceutically active agents.

13. A compound of formula (I) according to any one of claims 1 to 11 or a formulation according to claim 12 for use as a medicament.

14. A compound of formula (I) according to any one of claims 1 to 11 or a formulation according to claim 12 for use as an anti-endoparasite, anti-ectoparasite, arthropodicide, insecticide or acaricide.

15. for controlling pests or in the field of animal health (wherein methods of treating the animal body by surgery or therapy and diagnostic methods performed on the animal body are excluded), Or the use of a compound of formula (I) according to any one of claims 1 to 11 or a formulation according to claim 12 for the protection of crops or in vector control.

16. 16. The use according to claim 15, wherein the pest comprises or is an insect or an arachnid.

17. A method for controlling pests, characterized in that a compound of formula (I) according to any one of claims 1 to 11 or a formulation according to claim 12 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; or A method for protecting seeds or germinating plants from pests, the method comprising the step of contacting said seeds with a compound of formula (I) as defined in any one of claims 1 to 9 or with a formulation as defined in claim 12.

18. 18. The method of claim 17, wherein the pest is an insect pest.

19. 19. The method of claim 17 or 18, wherein the pest is selected from animal pests selected from the group consisting of insects and arachnids.

20. Seeds obtained by the method according to any one of claims 17 to 19.

21. Formula (IX-1), Formula (X) or Formula (XIII) 【Chemistry 12】 [In the formula, R ３ , R ４ , R ５ and R ６ has the meaning defined in any one of claims 1 to 9. An intermediate compound represented by the formula:

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