Heteroaryl-substituted pyrazine derivatives as insecticides

Abstract

The present invention relates to novel heteroaryl-substituted pyrazine derivatives of the general formula (I), wherein the structural element R 1 、R 2 、R 3 、R 4 、R 5 and R 6 have the meaning given in the description and relate to preparations and compositions comprising such compounds, as well as their use in plant protection for controlling animal pests including arthropods and insects and their use for controlling ectoparasites on animals. #imgabs0#

Description

[0001] The present invention relates to novel heteroaryl-substituted pyrazine derivatives, to formulations and compositions comprising such compounds, and to their use in plant protection for controlling animal pests, including arthropods and insects, and to their use for controlling ectoparasites on animals.

[0002] Certain heteroaryl-triazole and heteroaryl-tetrazole compounds are disclosed in WO 2017 / 192385 for controlling ectoparasites on animals and in WO 2019 / 170626 and WO 2019 / 215198 for controlling animal pests in the field of plant protection.

[0003] In addition, patent applications WO 2019 / 201835 (PCT / EP 2019 / 059624), WO 2019 / 197468 (PCT / EP 2019 / 059089), WO 2019 / 202077 (PCT / EP 2019 / 060081), WO 2019 / 206799 (PCT / EP2019 / 060077), EP 19169209.4, EP 19187891.7 and EP 19187899.0 (the latter three not yet published) relate to triazole and tetrazole compounds and their use in crop protection and / or their use as insecticides.

[0004] WO 2020 / 002563, WO 2020 / 053364, WO 2020 / 053365, WO 2020 / 079198 and WO 2020 / 169445 describe azole-amide compounds, while WO 2020 / 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, persistence, pedigree and resistance-destroying properties. Toxicity issues, compatibility with other active compounds or formulation adjuvants, and the cost required for active compound synthesis all play a role. In addition, resistance may occur. For farm animals, as well as companion animals and crop pests, resistant parasites are an increasingly serious problem. For all these reasons, it cannot be considered that the exploration of novel crop protection compositions or veterinary ectoparasiticides is thorough, and there is also a continuous need for novel compounds whose performance is at least improved in individual aspects compared to known compounds. It is particularly necessary to find new insecticides and parasiticides that overcome resistance.

[0006] It is an object of the present invention to provide compounds which broaden the insecticide spectrum in various aspects.

[0007] Thus, in a first aspect (Aspect 1.1), the present invention relates to compounds of formula (I) and their salts and N-oxides

[0008]

[0009] in

[0010] R 1 is hydrogen; in each case optionally substituted C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl;

[0011] or phenyl-C1-C6 alkyl, wherein the phenyl group is optionally substituted with 1 to 5 substituents, each of which is independently selected from halogen, hydroxyl, -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 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, C1-C3 cyanoalkylsulfonyl;

[0012] or heterocyclyl-C1-C6 alkyl, wherein the heterocyclyl is selected from 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 optionally substituted with 1 to 5 substituents, each of which is independently selected from halogen, hydroxyl, -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 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, C1-C3 cyanoalkylsulfonyl

[0013] R2 is phenyl or a 5- or 6-membered heteroaryl, each of which is optionally substituted with 1, 2 or 3 substituents independently selected from

[0014] - Halogen, hydroxyl, -CN, -COOH, -NO2, -NH2, -SF5;

[0015] - and in each case optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C6-cycloalkyloxy, 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-cycloalkylsulfinimido, S-C2-C6-alkenylsulfinimido, S-C2-C 6-alkynylsulfimino, S-phenylsulfimino, S-heterocyclylsulfimino, S-heteroarylsulfimino, S-C1-C6 alkylsulfonimidoyl, S-C3-C6 cycloalkylsulfonimido, S-C2-C6 alkenylsulfonimido, S-C2-C6 alkynylsulfonimido, S-phenylsulfonimido, S-heterocyclylsulfonimido, S-heteroarylsulfonimido, -C(=NOC1-C6 alkyl)H, -C(=NOC1-C6 alkyl)-C1-C6 alkyl, (C1-C6 alkyl)3-silyl;

[0016] - and substructures S1-S9, wherein the bond to the phenyl group or the 5- or 6-membered heteroaryl group is marked with a #, and Z is CO or CS and Y is independently selected from CO or SO2;

[0017]

[0018] R 21 is hydrogen or optionally substituted C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, -C1-C6-alkyl-C3-C6-cycloalkyl, phenyl, heteroaryl and heterocyclyl;

[0019] 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;

[0020] R 23 independently selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl and phenyl, each of which is optionally substituted;

[0021] R24 is each optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, phenyl, heteroaryl and heterocyclyl;

[0022] or

[0023] R 21 and R 22 together with the nitrogen atom to which they are attached represent a monocyclic or polycyclic optionally substituted 3- to 12-membered saturated or unsaturated heterocyclic group which may contain further heteroatoms;

[0024] - and 3- to 6-membered heterocyclyl or 5- to 6-membered heteroaryl, each containing 1 or 2 heteroatoms selected from N, O and S, wherein the 3- to 6-membered heterocyclyl or the 5- to 6-membered heteroaryl substituent may optionally carry 1, 2, 3 or 4 substituents independently 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, Alkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, 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, C1-C3 cyanoalkylsulfonyl;

[0025] R 3 is hydrogen or C1-C6-alkyl optionally substituted by 1 to 3 substituents selected from halogen, C3-C6-cycloalkyl and C1-C6-alkoxy;

[0026] R 4 is a monocyclic heterocycle selected from 5-membered heteroaryl, 6-membered heteroaryl and 3-6 membered heterocyclyl, each of which contains 1 or 2 heteroatoms selected from N, O and S, and each of which is optionally substituted with 1, 2, 3 or 4 substituents independently selected from

[0027] - Halogen, hydroxyl, -CN, -COOH, -NO2, -NH2, -SF5;

[0028] - and in each case optionally substituted 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-cycloalkyloxy, C1-C6-haloalkoxy, hydroxy-C1-C6-alkyl, -NH(C1-C6-alkyl), -NH(C1-C6-alkyl-C3-C6-cycloalkyl), -N(C1-C6-alkyl), -N(C1-C6-alkyl)(C1-C6-alkyl-C3-C6-cycloalkyl), -CO2C1-C6-alkyl, S -C1-C6 alkylsulfimido, S-C3-C6 cycloalkylsulfimido, S-C2-C6 alkenylsulfimido, S-C2-C6 alkynylsulfimido, S-phenylsulfimido, S-heterocyclylsulfimido, S-heteroarylsulfimido, S-C1-C6 alkylsulfoximido, S-C3-C6 cycloalkylsulfoximido, S-C2-C6 alkenylsulfoximido, S-C2-C6 alkynylsulfoximido, S-phenylsulfoximido, S-heterocyclylsulfoximido, S-heteroarylsulfoximido, -C(=NOC1-C6 alkyl)H, -C(=NOC1-C6 alkyl)-C1-C6 alkyl;

[0029] - and a 3- to 6-membered heterocyclyl containing 1 or 2 heteroatoms selected from N, O and S, wherein the 3- to 6-membered heterocyclyl substituent may optionally carry 1, 2, 3 or 4 substituents independently 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-C 6-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, C1-C3 cyanoalkylsulfonyl;

[0030] - and the following substructures S10-S18, wherein the bond to the pyrazine is marked with # and Z is CO or CS and Y is independently selected from CO or SO2:

[0031]

[0032] R 41is hydrogen or optionally substituted C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, -C1-C6-alkyl-C3-C6-cycloalkyl, phenyl, heteroaryl and heterocyclyl;

[0033] R 42 is hydrogen or in each case optionally substituted C1-C6-alkyl, C1-C6-haloalkyl and C3-C6-cycloalkyl;

[0034] R 43 independently selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl and phenyl, each of which is optionally substituted;

[0035] R 44 is each optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, phenyl, heteroaryl and heterocyclyl;

[0036] or

[0037] R 41 and R 42 together with the nitrogen atom to which they are attached represent a monocyclic or polycyclic optionally substituted 3- to 12-membered saturated or unsaturated heterocyclic group which may contain further heteroatoms;

[0038] 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;

[0039] 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(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.

[0040] Any description of a compound of formula (I) anywhere herein also includes any diastereomers or enantiomers and E / Z isomers that exist, as well as salts and N-oxides of the compound of formula (I).

[0041] Depending on the nature of the substituents, the compounds of formula (I) described anywhere herein may also be in the form of stereoisomers, i.e. geometric and / or optical isomers or isomer mixtures of varying composition. The present invention provides both the pure stereoisomers and any desired mixtures of these isomers, although generally only the compounds of formula (I) will be discussed herein.

[0042] However, according to the present invention, preference is given to using optically active stereoisomeric forms of the compounds of formula (I) and their salts.

[0043] The present invention therefore relates both to the pure enantiomers and diastereomers and to their mixtures.

[0044] According to one embodiment of the present invention, dextrorotatory compounds of formula (I) are preferred, i.e., those isomers that rotate plane polarized light in a clockwise direction ((+)-direction). Such enantiomers are generally designated with "(+)". Methods for separating enantiomers are well known in the art, for example, by chiral chromatography.

[0045] In formula (I), R 3 The compounds of the present invention may have an R- or S-configuration (according to the Cahn-Ingold-Prelog rule) at the carbon atom of 3 Compounds of formula (I) having the S-configuration at the carbon atom of are preferred.

[0046] If appropriate, the compounds of the formula (I) may be present in various polymorphic forms or as mixtures of various polymorphic forms. Both the pure polymorphs and the polymorph mixtures are provided by the invention and can be used according to the invention.

[0047] The present invention further relates to preferred embodiments as defined in the following aspects of the invention:

[0048] Compounds of formula (I) according to the following embodiments are excluded from the present invention:

[0049] (i) According to one embodiment, compounds of formula (I) are excluded, wherein R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided that the substituents are not on any adjacent carbon to the carbon to which C=O is attached, and each substituent is independently selected from the group consisting of 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.

[0050] (ii) According to another embodiment, compounds of formula (I) are excluded, wherein R 2 is phenyl or pyridine, wherein the phenyl or pyridine is optionally substituted with one or two substituents, provided that the substituents are not on any adjacent carbon to the carbon to which C=O is attached, and each substituent is independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, and -CN;

[0051] or wherein preferably each substituent is selected from: C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy and halogen.

[0052] (iii) According to another embodiment, compounds of formula (I) are excluded, wherein R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C3-C4 cycloalkyl, halogen and hydroxy.

[0053] (iv) According to another embodiment, compounds of formula (I) are excluded, wherein R 4is pyridine or pyrimidine, wherein the pyridine or pyrimidine is optionally substituted with a substituent selected from C1-C3 alkyl, C3-C4 cycloalkyl or halogen or hydroxy;

[0054] or wherein preferably, the pyridine or pyrimidine is optionally substituted by a substituent selected from C3-C4 cycloalkyl or halogen and hydroxyl;

[0055] Or wherein more preferably, the pyridine or pyrimidine is optionally substituted by a substituent selected from C3-C4 cycloalkyl, F, Cl and Br.

[0056] (v) According to another embodiment, compounds of formula (I) are excluded, wherein

[0057] R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided that the substituents are not on any adjacent carbon to the carbon to which C=O is attached, and each substituent is independently selected from the group consisting of 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,

[0058] and at the same time

[0059] R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C3-C4 cycloalkyl, halogen or hydroxy.

[0060] (vi) According to another embodiment, compounds of formula (I) are excluded, wherein

[0061] R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided that the substituents are not on any adjacent carbon to the carbon to which C=O is attached, and each substituent is independently selected from the group consisting of 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;

[0062] and at the same time

[0063] R 4is pyridine or pyrimidine, wherein the pyridine or pyrimidine is optionally substituted with a substituent selected from C1-C3 alkyl, C3-C4 cycloalkyl or halogen or hydroxy;

[0064] or wherein preferably, the pyridine or pyrimidine is optionally substituted by a substituent selected from C3-C4 cycloalkyl or halogen and hydroxyl;

[0065] Or wherein more preferably, the pyridine or pyrimidine is optionally substituted by a substituent selected from C3-C4 cycloalkyl, F, Cl and Br.

[0066] (vii) According to another embodiment, compounds of formula (I) are excluded, wherein

[0067] R 2 is phenyl or pyridine, wherein the phenyl or pyridine is optionally substituted with one or two substituents, provided that the substituents are not on any adjacent carbon to the carbon to which C=O is attached, and each substituent is independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, and -CN;

[0068] or wherein preferably each substituent is selected from: C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy and halogen;

[0069] and at the same time

[0070] R 4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents independently selected from C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C3-C4 cycloalkyl, halogen or hydroxy.

[0071] (viii) According to another embodiment, compounds of formula (I) are excluded, wherein

[0072] R 2 is phenyl or pyridine, wherein the phenyl or pyridine is optionally substituted with one or two substituents, provided that the substituents are not on any adjacent carbon to the carbon to which C=O is attached, and each substituent is independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, halogen, and -CN;

[0073] or wherein preferably each substituent is selected from: C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 thiohaloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy and halogen;

[0074] and at the same time

[0075] R 4 is pyridine or pyrimidine, wherein the pyridine or pyrimidine is optionally substituted with a substituent selected from C1-C3 alkyl, C3-C4 cycloalkyl or halogen or hydroxy;

[0076] or wherein preferably, the pyridine or pyrimidine is optionally substituted by a substituent selected from C3-C4 cycloalkyl or halogen and hydroxyl;

[0077] Or wherein more preferably, the pyridine or pyrimidine is optionally substituted by a substituent selected from C3-C4 cycloalkyl, F, Cl and Br.

[0078] In another aspect (Aspect 1.2), the present invention relates to compounds of formula (I) and their salts and N-oxides

[0079]

[0080] in

[0081] R 1 is hydrogen; in each case optionally substituted 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;

[0082] or phenyl-C1-C6 alkyl, wherein the phenyl group is optionally substituted with 1 to 5 substituents, each of which is independently selected from halogen, hydroxyl, -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-C C1-C4 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, C1-C3 cyanoalkylsulfonyl;

[0083] R 2 is phenyl or a 5- or 6-membered heteroaryl, each of which is optionally substituted with 1, 2 or 3 substituents independently selected from 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 cycloalkyloxy, C1-C3 haloalkoxy, C1-C3 cyano C1-C3 cyanoalkylthio, C1-C3 cyanoalkylsulfinyl, C1-C3 cyanoalkylsulfonyl, alkenylthio, alkynylthio, -NH(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), -C1-C3 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) -C1-C4 alkyl), -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, -SO2NH2, -SO2NH(C1-C4 alkyl), benzenesulfonyl and 3- to 6-membered heterocyclic radicals containing 1 or 2 heteroatoms selected from N, O and S,

[0084] wherein the phenyl and 3- to 6-membered heterocyclyl substituents may optionally carry 1, 2, 3 or 4 substituents independently 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 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, C1-C3 cyanoalkylsulfonyl;

[0085] R 3 is hydrogen or optionally substituted C1-C6 alkyl;

[0086] R 4is a monocyclic heterocycle selected from 5-membered heteroaryl, 6-membered heteroaryl and 3-6 membered heterocyclyl, each of which contains 1 or 2 heteroatoms selected from N, O and S, and wherein each is optionally substituted with 1, 2, 3 or 4 substituents independently 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 cycloalkyloxy, 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), -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), -CO N(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, -SO2NH(C1-C4-alkyl), phenylsulfonyl and 3- to 6-membered heterocyclyl containing 1 or 2 heteroatoms selected from N, O and S, wherein the phenyl and 3- to 6-membered heterocyclyl substituents of the substituents may optionally carry 1, 2, 3 or 4 substituents,The substituents are independently 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, 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, C1-C3 cyanoalkylsulfonyl;

[0087] 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, -CO2C1-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;

[0088] R 6 is 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, -C(O)-C1-C3-alkoxy, -CH-(C1-C3-alkoxy)2, -CO2C1-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.

[0089] In another aspect (Aspect 2.1), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein

[0090] R 1 is hydrogen; or in each case optionally substituted 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, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 substituents independently selected from halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2 and C1-C6 alkyl;

[0091] or phenyl-C1-C6 alkyl, wherein the phenyl group is optionally substituted with 1-5 substituents, each of which is independently selected from halogen, hydroxyl, -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 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, C1-C3 cyanoalkylsulfonyl;

[0092] or heterocyclyl-C1-C3 alkyl, wherein the heterocyclyl is selected from tetrahydropyranyl, tetrahydrofuranyl, oxetanyl and azetidinyl or heteroaryl, wherein the heteroaryl is selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, furanyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl and oxazolyl, and wherein the heteroaryl or heterocyclyl is optionally substituted with 1 to 3 substituents, each of which is independently selected from halogen, hydroxyl, -CN, -COOH, -CONH2, -CSNH2, -NO2, -Si(CH3)3, -SF5, -NH2, C1-C6 alkyl, C 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, C1-C3 cyanoalkylsulfonyl;

[0093] R 2 is selected from 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

[0094] - Halogen, hydroxyl, -CN, -COOH, -NO2, -NH2, -SF5;

[0095] - and in each case optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C3-haloalkyl, C1-C4-alkoxy, C3-C6-cycloalkyloxy, 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 aforementioned optionally substituted groups are optionally substituted with up to 3 substituents independently selected from 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;

[0096] - and substructures S1, S4, S7, S8, and S9, wherein the bond to the aforementioned phenyl, pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, or thiophene is marked with a # and Z is CO or CS;

[0097] -

[0098] R 21 is hydrogen or optionally substituted C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, -C1-C4 alkyl-C3-C6 cycloalkyl and 3- to 6-membered heterocyclyl;

[0099] 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;

[0100] R 24 is each optionally substituted C1-C4 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, phenyl, heteroaryl and 3- to 6-membered heterocyclyl;

[0101] Among them in R 21 、R 22 and R 24 The aforementioned optionally substituted groups in the definition of are optionally substituted by up to 3 substituents independently selected from 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;

[0102] or

[0103] R 21 and R 22 Together with the nitrogen atom to which they are attached, represent a 4- to 12-membered saturated or unsaturated heterocyclic radical which may contain up to two further heteroatoms selected from oxygen, nitrogen and sulfur and which is optionally substituted by one to three substituents selected from

[0104] Halogen, =O (oxo), =S (thiocarbonyl), hydroxy, -CN, -NO2, -SF5 and -NH2;

[0105] 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, C1-C4 haloalkylsulfonyl;

[0106] - and 3- to 6-membered heterocyclyl or 5- to 6-membered heteroaryl, each containing 1 or 2 heteroatoms selected from N, O and S, wherein the 3- to 6-membered heterocyclyl or the 5- to 6-membered heteroaryl substituent may optionally carry 1, 2 or 3 substituents independently 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, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl;

[0107] R 3 is hydrogen or C1-C6 alkyl optionally substituted by halogen, cyano, C3-C6 cycloalkyl or C1-C4 alkoxy;

[0108] R 4 is selected from pyridine, pyrimidine, pyrazine, pyridazine and thiazole, pyrazole, pyrrole, oxazole, isothiazole, isoxazole, thiophene and imidazole, each of which is optionally substituted with 1, 2 or 3 substituents independently selected from

[0109] - Halogen, hydroxyl, -CN, -COOH, -NO2, -NH2, -SF5;

[0110] - and in each case optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C3-haloalkyl, C1-C4-alkoxy, C3-C6-cycloalkyloxy, 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) wherein the aforementioned optionally substituted groups are optionally substituted with up to 3 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;

[0111] - and substructures S10, S11, S13, S14, S16, S17, and S18, wherein the bond to the aforementioned pyridine, pyrimidine, pyrazine, pyridazine, thiazole, pyrazole, pyrrole, oxazole, isothiazole, isoxazole, thiophene, or imidazole is marked with a # and Z is CO or CS;

[0112]

[0113] R 41 is hydrogen or optionally substituted C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, -C1-C4 alkyl-C3-C6 cycloalkyl and 3- to 6-membered heterocyclyl;

[0114] 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;

[0115] R 43 independently selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl, and C3-C6 cycloalkyl, each optionally substituted;

[0116] R 44 is each optionally substituted C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, phenyl, heteroaryl and 3- to 6-membered heterocyclyl;

[0117] Among them in R 41 、R 42 、R 43 and R24 The aforementioned optionally substituted groups in the definition of are optionally substituted by up to 3 substituents independently selected from 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;

[0118] or

[0119] R 41 and R 42 Together with the nitrogen atom to which they are attached, represent a 4- to 12-membered saturated or unsaturated heterocyclic group which may contain up to two further heteroatoms selected from oxygen, nitrogen, sulfur and silicon and which is optionally substituted by one to three substituents selected from

[0120] Halogen, =O (oxo), =S (thiocarbonyl), hydroxy, -CN, -NO2, -SF5 and -NH2;

[0121] 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, C1-C4 haloalkylsulfonyl;

[0122] - and 3- to 6-membered heterocyclyl or 5- to 6-membered heteroaryl, each containing 1 or 2 heteroatoms selected from N, O and S, wherein the 3- to 6-membered heterocyclyl or the 5- to 6-membered heteroaryl substituent may optionally carry 1, 2 or 3 substituents independently 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, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl;

[0123] 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-C4 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 the aforementioned optionally substituted groups are optionally substituted with up to 3 substituents independently selected from halogen, hydroxyl, -CN, -NO2, -Si(CH3)3, -NH2 and C1-C3 alkyl;

[0124] 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-C4 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 the aforementioned optionally substituted groups are optionally substituted by up to 3 substituents independently selected from halogen, hydroxyl, -CN, -NO2, -Si(CH3)3, -NH2 and C1-C3 alkyl.

[0125] In another aspect (Aspect 2.2), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein

[0126] R 1 is hydrogen; or in each case optionally substituted 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;

[0127] or phenyl-C1-C6 alkyl, wherein the phenyl group is optionally substituted with 1 to 5 substituents, each of which is independently selected from halogen, hydroxyl, -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-C C1-C4 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, C1-C3 cyanoalkylsulfonyl;

[0128] R 2is selected from phenyl, pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene and imidazole, each of which is optionally substituted with 1, 2 or 3 substituents independently selected from 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 Alkoxy, 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), -CON H-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, -SO2NH2, -SO2NH(C1-C4-alkyl), benzenesulfonyl and 3- to 6-membered heterocyclic radicals containing 1 or 2 heteroatoms selected from N, O and S,

[0129] wherein the phenyl and 3- to 6-membered heterocyclyl substituents of the substituents may optionally carry 1, 2, 3 or 4 substituents independently 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, 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, C1-C3 cyanoalkylsulfonyl;

[0130] R 3 is hydrogen or optionally substituted C1-C6 alkyl;

[0131] R 4is selected from pyridine, pyrimidine, pyrazine, pyridazine and thiazole, each of which is optionally substituted with 1, 2, 3 or 4 substituents independently selected from 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 alkyl C3-C6 cycloalkyl), -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), -NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl), -NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl), -NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl), -NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl), -NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl), -NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl), -NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl), -NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl), -NHCO-C3-C6 cycloalkyl, -NHCO(C1-C4 alkyl), -NHCO -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(C -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, -SO2NH(C1-C4 alkyl), phenylsulfonyl and 3- to 6-membered heterocyclyl containing 1 or 2 heteroatoms selected from N, O and S, wherein the phenyl and 3- to 6-membered heterocyclyl substituents of the substituents may optionally carry 1, 2, 3 or 4 substituents,The substituents are independently 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, 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, C1-C3 cyanoalkylsulfonyl;

[0132] 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, -CO2C1-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;

[0133] R 6 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, -CO2C1-C4-alkoxy 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.

[0134] In another aspect (Aspect 3.1), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein

[0135] 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;

[0136] R 2 is selected from pyrazole, phenyl, pyridine, pyrimidine, pyrazine and pyridazine, each of which is optionally substituted with a total of 1, 2 or 3 substituents, wherein 1, 2 or 3 of the optional substituents are independently selected from Group A consisting of the following members

[0137] - Halogen, hydroxyl, -CN, -COOH, -NO2, -NH2, -SF5;

[0138] - 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;

[0139] And optionally one of the optional substituents may be selected from Group B consisting of the following members

[0140] - substructures S1, S4, S7, S8 and S9, in which the bond to the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is marked with # and Z is CO;

[0141]

[0142] R 21 is hydrogen or in each case optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl;

[0143] R 22 is hydrogen or in each case optionally substituted C1-C3 alkyl, C1-C3 haloalkyl and C3-C4 cycloalkyl;

[0144] R 24 is in each case optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl and phenyl;

[0145] Among them in R 21 、R 22 and R 24 The aforementioned optionally substituted groups in the definition of are optionally substituted by up to 3 substituents independently selected from halogen, -CN, -NO2, -Si(CH3)3, C1-C3 alkyl, C1-C3 haloalkyl;

[0146] R 3 is hydrogen or C1-C6 alkyl;

[0147] R 4 is selected from pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene and imidazole, wherein each of the aforementioned 6-membered heteroaryl groups is optionally substituted with 1, 2 or 3 substituents and each of the aforementioned 5-membered heteroaryl groups is optionally substituted with 1 or 2 substituents, wherein in each case up to all of the optional substituents are independently selected from the group consisting of:

[0148] - Halogen, hydroxyl, -CN, -COOH, -NO2, -NH2, -SF5;

[0149] - and C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C4 cyanocycloalkyl, C1-C3 alkoxy, C3-C4 cycloalkyloxy, 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;

[0150] And optionally one of the optional substituents may be selected from the group consisting of the following members

[0151] - Substructures S10, S13, S16, S17, and S18, wherein the bond to the aforementioned pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene, or imidazole is marked with a # and Z is CO;

[0152]

[0153] R 41 is hydrogen or optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, -C1-C2 alkyl-C3-C4 cycloalkyl and 3- to 6-membered heterocyclyl containing 1 heteroatom selected from N, O and S;

[0154] R 42is hydrogen or in each case optionally substituted C1-C3-alkyl, C1-C3-haloalkyl, -C1-C2-alkyl-C3-C4-cycloalkyl and C3-C4-cycloalkyl;

[0155] R 44 is in each case optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl;

[0156] Among them, R 41 、R 42 and R 44 The aforementioned optionally substituted groups defined are optionally substituted with up to 2 substituents independently selected from halogen, -CN, -NO2, -Si(CH3)3, C1-C3 alkyl, C1-C3 haloalkyl;

[0157] or

[0158] R 41 and R 42 Together with the nitrogen atom to which they are attached, they represent a monocyclic 4- to 8-membered saturated heterocyclic radical which may contain up to one further heteroatom selected from oxygen, nitrogen, sulfur and silicon and which is optionally substituted by one to three substituents selected from

[0159] Halogen, =O (oxo), =S (thiocarbonyl), hydroxy, -CN, -NO2, and -NH2;

[0160] and C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0161] R 5 is hydrogen, halogen, -CN, C1-C3-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, C1-C3-alkoxy, C1-C3-haloalkoxy;

[0162] R 6 It is hydrogen, halogen, -CN, C1-C3-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, C1-C3-alkoxy, C1-C3-haloalkoxy.

[0163] In another aspect (Aspect 3.2), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein

[0164] R 1is 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;

[0165] R 2 is selected from phenyl, pyridine, pyrimidine, pyrazine and pyridazine, each of which is optionally substituted with a total of 1, 2 or 3 substituents, wherein 1, 2 or 3 of the optional substituents are independently selected from Group A consisting of the following members

[0166] - Halogen, hydroxyl, -CN, -COOH, -NO2, -NH2, -SF5;

[0167] - 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;

[0168] And optionally one of the optional substituents may be selected from Group B consisting of the following members

[0169] - substructures S1, S4, S7, S8 and S9, in which the bond to the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is marked with # and Z is CO;

[0170]

[0171] R 21 is hydrogen or in each case optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl;

[0172] R 22 is hydrogen or in each case optionally substituted C1-C3 alkyl, C1-C3 haloalkyl and C3-C4 cycloalkyl;

[0173] R 24 is in each case optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl and phenyl;

[0174] Among them in R 21 、R 22 and R 24The aforementioned optionally substituted groups in the definition of are optionally substituted by up to 3 substituents independently selected from halogen, -CN, -NO2, -Si(CH3)3, C1-C3 alkyl, C1-C3 haloalkyl;

[0175] R 3 is hydrogen or C1-C6 alkyl;

[0176] R 4 is selected from pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene and imidazole, wherein each of the aforementioned 6-membered heteroaryl groups is optionally substituted with 1, 2 or 3 substituents and each of the aforementioned 5-membered heteroaryl groups is optionally substituted with 1 or 2 substituents, wherein in each case up to all of the optional substituents are independently selected from the group consisting of:

[0177] - Halogen, hydroxyl, -CN, -COOH, -NO2, -NH2, -SF5;

[0178] - and C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C3-C4 cyanocycloalkyl, C1-C3 alkoxy, C3-C4 cycloalkyloxy, 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;

[0179] And optionally one of the optional substituents may be selected from the group consisting of the following members

[0180] - Substructures S10, S13, S16, S17, and S18, wherein the bond to the aforementioned pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene, or imidazole is marked with a # and Z is CO;

[0181]

[0182] R 41 is hydrogen or optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, -C1-C2 alkyl-C3-C4 cycloalkyl and 3- to 6-membered heterocyclyl containing 1 heteroatom selected from N, O and S;

[0183] R 42is hydrogen or in each case optionally substituted C1-C3-alkyl, C1-C3-haloalkyl, -C1-C2-alkyl-C3-C4-cycloalkyl and C3-C4-cycloalkyl;

[0184] R 44 is in each case optionally substituted C1-C3-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl.

[0185] Among them, R 41 、R 42 and R 44 The aforementioned optionally substituted groups defined are optionally substituted with up to 2 substituents independently selected from halogen, -CN, -NO2, -Si(CH3)3, C1-C3 alkyl, C1-C3 haloalkyl;

[0186] or

[0187] R 41 and R 42 Together with the nitrogen atom to which they are attached, they represent a monocyclic 4- to 8-membered saturated heterocyclic radical which may contain up to one further heteroatom selected from oxygen, nitrogen, sulfur and silicon and which is optionally substituted by one to three substituents selected from

[0188] Halogen, =O (oxo), =S (thiocarbonyl), hydroxy, -CN, -NO2, and -NH2;

[0189] and C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;

[0190] R 5 is hydrogen, halogen, -CN, C1-C3-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, C1-C3-alkoxy, C1-C3-haloalkoxy;

[0191] R 6 It is hydrogen, halogen, -CN, C1-C3-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, C1-C3-alkoxy, C1-C3-haloalkoxy.

[0192] In another aspect (Aspect 3.3), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein

[0193] R 1 is hydrogen; or in each case optionally substituted 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;

[0194] R 2 is selected from phenyl, pyridine, pyrimidine, pyrazine and pyridazine, each of which is optionally substituted with 1, 2 or 3 substituents independently selected from 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), -N (C1-C4 alkyl) CO-C1-C4 alkyl, -N (C1-C4 alkyl) CO-C3-C6 cycloalkyl, -N (C1-C4 alkyl) SO2C1-C4 alkyl, -N (SO2C1-C4 alkyl) 2, -CO2C1-C4 alkyl, -CONH (C1-C4 alkyl), -CONH (C3-C6 cycloalkyl), -CONH-phenyl, -CON( C1-C4 alkyl)2, -CON(C1-C4 alkyl)(C3-C6 cycloalkyl), -CON(C1-C4 alkyl)-phenyl, -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alkyl, (C1-C4 alkyl)3-silyl, -SO2NH2, -SO2NH(C1-C4 alkyl), phenylsulfonyl and 3- to 6-membered heterocyclic radicals containing 1 or 2 heteroatoms selected from N, O and S,

[0195] wherein the phenyl and 3- to 6-membered heterocyclyl substituents of the substituents may optionally carry 1, 2 or 3 substituents independently selected from halogen, C1-C6 alkyl and C1-C3 cyanoalkyl;

[0196] R 3 is hydrogen or optionally substituted C1-C6 alkyl;

[0197] R 4is selected from pyridine, pyrimidine, pyrazine, pyridazine and thiazole, each of which is optionally substituted with 1, 2, 3 or 4 substituents independently selected from 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-C C3-C6 cycloalkylsulfonyl, 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), -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, -C(=NOC1-C4-alkyl)-C1-C4-alkyl, -SO2NH2, -SO2NH(C1-C4-alkyl), phenylsulfonyl and 3- to 6-membered heterocyclyl containing 1 or 2 heteroatoms selected from N, O and S, wherein the phenyl and 3- to 6-membered heterocyclyl substituents of the substituents may optionally carry 1, 2 or 3 substituents independently selected from halogen, C1-C6-alkyl and C1-C3-cyanoalkyl;

[0198] 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), -CO2C1-C4-alkyl, -CONH(C1-C4-alkyl), -CON(C1-C4-alkyl), -NHCO-C1-C4-alkyl, -N(C1-C4-alkyl)CO-C1-C4-alkyl, -C(=NOC1-C4-alkyl)H or -C(=NOC1-C4-alkyl)-C1-C4-alkyl;

[0199] R 6 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), -CO2C1-C4-alkyl, -CONH(C1-C4-alkyl), -CON(C1-C4-alkyl), -NHCO-C1-C4-alkyl, -N(C1-C4-alkyl)CO-C1-C4-alkyl, -C(=NOC1-C4-alkyl)H or -C(=NOC1-C4-alkyl)-C1-C4-alkyl.

[0200] In another aspect (Aspect 4.1), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein

[0201] R 1 is hydrogen; methyl, ethyl, n-propyl, isopropyl, cyanomethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, methylsulfonylethyl, ethylsulfonylethyl;

[0202] R 2selected from pyrazole, phenyl and pyridine, each of which is optionally substituted with 1 or 2 substituents independently selected from 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 bear fluorine, chlorine or methyl substituents;

[0203] R 3 is hydrogen, methyl, ethyl, n-propyl or isopropyl;

[0204] R 4 is selected from the group consisting of pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrazin-3-yl and 1,3-thiazol-2-yl, 1,3-oxazol-2-yl, 1,2-oxazol-3-yl, 1,2-thiazol-3-yl, 1 H -pyrazol-1-yl, 1 H -pyrazol-3-yl, 1 H -imidazol-4-yl, each of which is optionally substituted by 1 substituent selected from 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, difluoromethyl Thio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, -COOCH3, -COOCH2CH3 and substructure S13, wherein the aforementioned 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, 1 H -pyrazol-1-yl, 1 H -pyrazol-3-yl, 1 H -The bond of imidazol-4-yl is marked with # and Z is CO;

[0205]

[0206] R 41is 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;

[0207] 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;

[0208] R 41 and R 42 Together with the nitrogen atom to which they are attached, they represent pyrrolidine, piperidine, azepane, morpholine, oxazepane, azasilolane, azasilinane, azasilepane, each of which is optionally substituted by 1 or 2 methyl groups;

[0209] 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;

[0210] 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.

[0211] In another aspect (Aspect 4.2), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein

[0212] R 1 is hydrogen; methyl, ethyl, n-propyl, isopropyl, cyanomethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, methylsulfonylethyl, ethylsulfonylethyl;

[0213] R 2selected from phenyl and pyridine, each of which is optionally substituted with 1 or 2 substituents independently selected from fluoro, chloro, bromo, iodo, 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-methylethyl-1-yl (also known as 1-methyl-1-cyanoethyl), methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, cyanomethoxy, methylthio, methylsulfinyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, (CH3)3-silyl, phenylsulfonyl which may carry fluorine, chlorine or methyl substituents;

[0214] R 3 is hydrogen, methyl, ethyl, n-propyl or isopropyl;

[0215] R 4 is selected from the group consisting of pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrazin-3-yl and 1,3-thiazol-2-yl, 1,3-oxazol-2-yl, 1,2-oxazol-3-yl, 1,2-thiazol-3-yl, 1 H -pyrazol-1-yl, 1 H -pyrazol-3-yl, 1 H -imidazol-4-yl, each of which is optionally substituted by 1 substituent selected from 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, difluoromethyl Thio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, -COOCH3, -COOCH2CH3 and substructure S13, wherein the aforementioned 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, 1 H -pyrazol-1-yl, 1 H -pyrazol-3-yl, 1 H -The bond of imidazol-4-yl is marked with # and Z is CO;

[0216]

[0217] R 41is 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;

[0218] 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;

[0219] R 41 and R 42 Together with the nitrogen atom to which they are attached, they represent pyrrolidine, piperidine, azepane, morpholine, oxazazepane, azasilacyclopentane, azasilacyclohexane, azasilacycloheptane, each of which is optionally substituted with 1 or 2 methyl groups.

[0220] 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;

[0221] 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.

[0222] In another aspect (Aspect 4.3), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein

[0223] R 1 is hydrogen; methyl, ethyl, n-propyl, isopropyl, cyanomethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, methylthiomethyl, ethylthiomethyl;

[0224] R 2selected from phenyl, pyridine, pyrimidine, pyrazine and pyridazine, each of which is optionally substituted with 1, 2 or 3 substituents independently selected from 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, trifluoromethyl, methyl thiophene ... methoxy, cyanomethoxy, isopropan-2-ol, methylthio, methylsulfinyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, (CH3)3-silyl, -SO2NH2, benzenesulfonyl which may carry fluorine, chlorine or methyl substituents, and oxetane, tetrahydropyran and piperazine, each of which may carry a methyl substituent;

[0225] R 3 is hydrogen, methyl, ethyl, n-propyl or isopropyl;

[0226] R 4 is selected from pyridine, pyrimidine, pyrazine, pyridazine and thiazole, each of which is optionally substituted with 1, 2 or 3 substituents independently selected from 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, methylsulfinyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulfinyl, trifluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, -NH(CH3), -N(CH3)2, -NHCO-CH3, NHCO-cyclopropyl, -CON(CH3)(CH3-cyclopropyl), -SO2NH2 and phenylsulfonyl which may carry fluorine, chlorine, methyl or cyanomethyl substituents;

[0227] 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;

[0228] R 6is 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.

[0229] In another aspect (Aspect 5.1), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein

[0230] R 1 is hydrogen or cyclopropylmethyl;

[0231] R 2 selected from pyrazole, phenyl and pyridine, each of which is optionally substituted with 1 or 2 substituents independently selected from 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;

[0232] R 3 It is a methyl group;

[0233] R 4 Selected from pyridin-2-yl, pyrimidin-2-yl, 1,3-thiazol-2-yl, 1 H -pyrazol-1-yl, each of which is optionally substituted with 1 substituent selected from fluoro, chloro, bromo, -CN, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, -COOH, -COOCH3, -COOCH2CH3, and substructure S13, wherein the bond marked with # is attached to the C-5 position of the aforementioned pyridin-2-yl, pyrimidin-2-yl, 1,3-thiazol-2-yl- or to the C-4-position in the aforementioned 1H-pyrazol-1-yl, and Z is CO;

[0234]

[0235] R 41 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl, cyclopropyl;

[0236] R 42 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl;

[0237] R 41 and R 42Together with the nitrogen atom to which they are attached, they represent pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane or ( Si , Si -dimethyl)azasilane;

[0238] R 5 is hydrogen or methyl;

[0239] R 6 is hydrogen or methyl.

[0240] In another aspect (Aspect 5.2), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein

[0241] R 1 is hydrogen or cyclopropylmethyl;

[0242] R 2 is selected from phenyl and pyridine, each of which is optionally substituted with 1 or 2 substituents independently selected from fluorine, chlorine, bromine, iodine, -CN, -SF5, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl;

[0243] R 3 It is a methyl group;

[0244] R 4 Selected from pyridin-2-yl, pyrimidin-2-yl, 1,3-thiazol-2-yl, 1 H -pyrazol-1-yl, each of which is optionally substituted with 1 substituent selected from fluoro, chloro, bromo, -CN, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, -COOH, -COOCH3, -COOCH2CH3, and substructure S13, wherein the bond marked with # is attached to the C-5 position of the aforementioned pyridin-2-yl, pyrimidin-2-yl, 1,3-thiazol-2-yl- or to the C-4-position in the aforementioned 1H-pyrazol-1-yl, and Z is CO;

[0245]

[0246] R 41 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl;

[0247] R 42 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl;

[0248] R41 and R 42 Together with the nitrogen atom to which they are attached, they represent pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane, ( Si , Si -dimethyl) azasilanol,

[0249] R 5 is hydrogen or methyl;

[0250] R 6 is hydrogen or methyl.

[0251] In another aspect (Aspect 5.3), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein

[0252] R 1 is hydrogen, methyl, cyclopropylmethyl, ethoxymethyl or ethylthiomethyl;

[0253] R 2 is selected from phenyl and pyridine, each of which is optionally substituted with 1, 2 or 3 substituents independently selected from fluorine, chlorine, bromine, CN, SF5, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, trifluoromethyl, cyanomethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, cyanomethoxy, isopropan-2-ol, (CH3)3-silyl, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, -SO2NH2, phenylsulfonyl which may carry a fluorine substituent, and oxetane, tetrahydropyran and piperazine, each of which may carry a methyl substituent;

[0254] R 3 It is a methyl group;

[0255] R 4 is selected from pyridine, pyrimidine, pyrazine, pyridazine, and thiazole, each of which is optionally substituted with 1 or 2 substituents independently selected from fluoro, chloro, bromo, 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;

[0256] 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;

[0257] 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.

[0258] In another aspect (Aspect 6), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein R 2 is phenyl, which may be substituted as defined anywhere above, and wherein the remaining substituents may have meanings as defined anywhere above.

[0259] In a preferred embodiment of aspect 6 of the present invention above, R 2 is the following substructure Q1, where the bond to the C=O- group is marked with #:

[0260]

[0261] in

[0262] R 25 is 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- C4-alkyl, -N(C1-C4-alkyl)CO-C3-C6-cycloalkyl, -N(C1-C4-alkyl)SO2C1-C4-alkyl, -N(SO2C1-C4-alkyl)2, -CO2C1-C4-alkyl, -CONH(C1-C4-alkyl), -CONH(C3-C6-cycloalkyl), -CONH-phenyl, -CON(C1-C4-alkyl)2, -CON(C1-C4-alkyl)(C3-C6-cycloalkyl), -CON(C1-C4-alkyl)-phenyl, -C(=NOC1-C4-alkyl)H, -C(=NOC1-C4-alkyl)-C1-C4-alkyl, (C1-C4-alkyl)3-silyl, -SO2NH(C1-C4-alkyl), phenylsulfonyl or a 3- to 6-membered heterocyclic group containing 1 or 2 heteroatoms selected from N, O and S,

[0263] wherein the phenyl and 3- to 6-membered heterocyclyl substituents of the aforementioned substituents may optionally carry 1, 2 or 3 substituents independently selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl and C1-C3 cyanoalkyl; and

[0264] R 26 It is 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.

[0265] R 25 and R 26 Preferably defined as follows:

[0266] R 25 is -SO2NH2, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, (CH3)3-silyl, cyanomethoxy, tert-butyl, cyclopropyl, cyanomethyl, 1-cyano-1-methylethan-1-yl, 1-cyanocyclopropyl, isopropan-2-ol, or phenylsulfonyl which may optionally carry a fluorine substituent; or

[0267] is oxetane, tetrahydropyran or piperazine, each of which may optionally carry a methyl substituent;

[0268] R 26 It is fluorine, chlorine, bromine, CN, SF5, methyl, ethyl, n-propyl, isopropyl, butyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, or cyclopropyl.

[0269] According to another embodiment, R 25 and R 26 Preferably defined as follows:

[0270] R 25 is -SO2NH2, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, (CH3)3-silyl, cyanomethoxy, tert-butyl, cyclopropyl, cyanomethyl, isopropan-2-ol, or phenylsulfonyl which may optionally carry a fluorine substituent; or

[0271] is oxetane, tetrahydropyran or piperazine, each of which may optionally carry a methyl substituent;

[0272] R 26 It is fluorine, chlorine, bromine, CN, SF5, methyl, ethyl, n-propyl, isopropyl, butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, or cyclopropyl.

[0273] R 25 and R 26 Particularly preferably defined as follows:

[0274] R 25 is methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, tert-butyl, cyclopropyl, 1-cyano-1-methyleth-1-yl, 1-cyanocyclopropyl, 4-fluorophenylsulfonyl; and

[0275] R 26 It is fluorine, chlorine, bromine, iodine, CN, SF5, methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, or cyclopropyl.

[0276] According to another embodiment, R 25 and R 26 Particularly preferably defined as follows:

[0277] R 25 is methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, tert-butyl, cyclopropyl; and

[0278] R 26 It is fluorine, chlorine, bromine, CN, SF5, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylsulfonyl, ethylsulfonyl, cyclopropylsulfonyl, trifluoromethylsulfonyl, or cyclopropyl.

[0279] In other embodiments of aspect 6 of the present invention above, R 2 is the following substructure Q2, wherein the bond to the C=O- group is marked with # and

[0280]

[0281] in

[0282] R 27is halogen, -CN, -COOH, -CONH2, -NO2, -SF5, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 haloalkylthio; and

[0283] R 28 It is halogen, -CN, -COOH, -CONH2, -NO2, -SF5, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 haloalkylthio.

[0284] R 27 and R 28 Preferably defined as follows:

[0285] R 27 is fluorine, chlorine, bromine, -CN, -SF5, methyl, ethyl, n-propyl, isopropyl, butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy;

[0286] R 28 It is fluorine, chlorine, bromine, -CN, -SF5, methyl, ethyl, n-propyl, isopropyl, butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy.

[0287] In another aspect (Aspect 7), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein R 2 is thiophene, pyrazole or imidazole, each of which may be substituted as defined anywhere above, and wherein the remaining substituents may have meanings as defined anywhere above.

[0288] In a preferred embodiment of aspect 7 of the present invention above, R 2 is selected from optionally substituted thiophene and pyrazole groups:

[0289]

[0290] in

[0291] R 9 is selected from halogen, preferably fluorine, chlorine and bromine, C1-C3 alkyl, preferably methyl, C1-C3 haloalkyl, preferably trifluoromethyl, and pentafluorosulfanyl;

[0292] n is an integer of 0, 1 or 2, preferably 1 or 2; and

[0293] Y represents hydrogen, C1-C3 alkyl, preferably methyl and ethyl, cycloalkyl, preferably cyclopropyl, C1-C3 haloalkyl, preferably trifluoromethyl.

[0294] Such a group R 2A preferred example is represented by the following formula:

[0295] .

[0296] In another aspect (Aspect 8), the present invention relates to compounds of formula (I) as described above, and salts and N-oxides thereof, wherein R 4 is selected from pyridine, pyrimidine, thiazole, pyrazole and pyrazine, each of which may be substituted as defined anywhere above, and wherein the remaining substituents may have meanings as defined anywhere above.

[0297] In a preferred embodiment of aspect 8 of the present invention above, R 4 is selected from pyridine, pyrimidine and thiazole, each of which may be substituted as defined anywhere above, and wherein the remaining substituents may have meanings as defined anywhere above, and salts and N-oxides thereof.

[0298] In a preferred embodiment of aspect 8 of the present invention above, the compound of formula (I) is characterized in that it has a structure according to formula (Ii), (I-ii) or (I-iii)

[0299]

[0300] in

[0301] R 1 、R 2 、R 3 、R 5 and R 6 has the meaning as defined in any of the Aspects above; and

[0302] R 8 represents 0, 1, 2, 3 or 4 of any of the aspects described anywhere above for R 4 The same or different substituents as defined above, preferably R 8 represents 0, 1 or 2 substituents, more preferably 0 or 1 substituent;

[0303] and their salts and N-oxides.

[0304] In another preferred embodiment of aspect 8 of the present invention above, the compound of formula (I) is characterized in that it has a structure according to formula (Ii) above, and R 1 、R 2 、R 3 、R 5 、R 6 has the meaning as defined in any of the aspects described above, and R 8represents 0, 1 or 2, preferably 0 or 1, identical or different substituents selected from fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, CONH cyclopropyl, CO-N-morpholinyl, CON(CH3(cyclopropylmethyl), CO-N-pyrrolidinyl, CON(CH3(CH2CN); and salts and N-oxides thereof.

[0305] In another preferred embodiment of aspect 8 of the present invention above, the compound of formula (I) is characterized in that it has a structure according to formula (Ii) above, and R 1 、R 2 、R 3 、R 5 、R 6 has the meaning as defined in any of the aspects described above, and R 8 represents 0, 1 or 2, preferably 0 or 1, identical or different substituents selected from -CN, -COOH, -COOCH3, -COOCH2CH3 and substructure S13, wherein the bond marked with # is attached to the pyridine, preferably in the C-5-position, and Z is CO;

[0306]

[0307] R 41 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl or cyclopropyl;

[0308] R 42 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl;

[0309] R 41 and R 42 Together with the nitrogen atom to which they are attached, they represent pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane, ( Si , Si -dimethyl) azasilanol,

[0310] and their salts and N-oxides.

[0311] In another preferred embodiment of aspect 8 of the present invention above, the compound of formula (I) is characterized in that it has a structure according to formula (I-ii) above, and R 1 、R 2 、R 3 、R 5 、R 6 has the meaning as defined in any of the aspects described above, and R 8represents 0, 1 or 2, preferably 0 or 1, identical or different substituents selected from fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, CONH cyclopropyl, CO-N-morpholinyl, CON(CH3(cyclopropylmethyl), CO-N-pyrrolidinyl, CON(CH3(CH2CN); and salts and N-oxides thereof.

[0312] In another preferred embodiment of aspect 8 of the present invention above, the compound of formula (I) is characterized in that it has a structure according to formula (I-ii) above, and R 1 、R 2 、R 3 、R 5 、R 6 has the meaning as defined in any of the aspects described above, and R 8 represents 0, 1 or 2, preferably 0 or 1, identical or different substituents selected from -CN, -COOH, -COOCH3, -COOCH2CH3 and substructure S13, wherein the bond marked with # is attached to the pyrimidine, preferably at the C-5-position, and Z is CO;

[0313]

[0314] R 41 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl or cyclopropyl;

[0315] R 42 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl;

[0316] R 41 and R 42 Together with the nitrogen atom to which they are attached, they represent pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane, ( Si , Si -dimethyl) azasilanol,

[0317] and their salts and N-oxides.

[0318] In another preferred embodiment of aspect 8 of the present invention above, the compound of formula (I) is characterized in that it has a structure according to formula (I-iii) above, and R 1 、R 2 、R 3 、R 5 、R 6 has the meaning as defined in any of the aspects described above, and R 8represents 0, 1 or 2, preferably 0 or 1, identical or different substituents selected from fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, CONH cyclopropyl, CO-N-morpholinyl, CON(CH3(cyclopropylmethyl), CO-N-pyrrolidinyl, CON(CH3(CH2CN); and salts and N-oxides thereof.

[0319] In another preferred embodiment of aspect 8 of the present invention above, the compound of formula (I) is characterized in that it has a structure according to formula (I-iii) above, and R 1 、R 2 、R 3 、R 5 、R 6 has the meaning as defined in any of the aspects described above, and R 8 represents 0, 1 or 2, preferably 0 or 1, identical or different substituents selected from fluorine, chlorine, bromine, -CN, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, -COOH, -COOCH3, -COOCH2CH3 and substructure S13, wherein the bond marked with # is attached to the thiazole, preferably to the C-5 position, and Z is CO;

[0320]

[0321] R 41 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl or cyclopropyl;

[0322] R 42 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl;

[0323] R 41 and R 42 Together with the nitrogen atom to which they are attached, they represent pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane, ( Si , Si -dimethyl) azasilanol,

[0324] and their salts and N-oxides.

[0325] In another preferred embodiment of aspect 8 of the present invention above, the compound of formula (I) is characterized in that it has a structure according to formula (I-iv)

[0326]

[0327] in

[0328] R 1 、R 2、R 3 、R 5 and R 6 has the meaning as defined in any of the Aspects above; and

[0329] R 8 represents 0, 1, 2 or 3 of any of the aspects described anywhere above for R 4 The same or different substituents as defined above, preferably R 8 represents 0, 1 or 2 substituents, more preferably 0 or 1 substituent;

[0330] and their salts and N-oxides.

[0331] In another preferred embodiment of aspect 8 of the present invention above, the compound of formula (I) is characterized in that it has a structure according to formula (I-iv) above, and R 1 、R 2 、R 3 、R 5 、R 6 has the meaning as defined in any of the aspects 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, CONH cyclopropyl, CO-N-morpholinyl, CON(CH3(cyclopropylmethyl), CO-N-pyrrolidinyl, CON(CH3(CH2CN); and salts and N-oxides thereof.

[0332] In another preferred embodiment of aspect 8 of the present invention above, the compound of formula (I) is characterized in that it has a structure according to formula (I-iv) above, and R 1 、R 2 、R 3 、R 5 、R 6 has the meaning as defined in any of the aspects described above, and R 8 represents 0, 1 or 2, preferably 0 or 1, identical or different substituents selected from fluorine, chlorine, bromine, -CN, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, -COOH, -COOCH3, -COOCH2CH3 and substructure S13, wherein the bond marked with # is attached to the thiazole, preferably to the C-5 position, and Z is CO;

[0333]

[0334] R 41 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl, cyclopropyl;

[0335] R42 is hydrogen, methyl, ethyl, propan-2-yl, 2,2,2-trifluoroethyl, cyanomethyl, cyclopropylmethyl, 2-methyl-n-propyl;

[0336] R 41 and R 42 Together with the nitrogen atom to which they are attached, they represent pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane, ( Si , Si -dimethyl) azasilanol,

[0337] and their salts and N-oxides.

[0338] In another aspect (Aspect 9), the present invention relates to compounds of formula (I) as described in any of the above aspects, and salts and N-oxides thereof, characterized in that they have a structure according to formula (IV), (I-vi) or (I-vii)

[0339]

[0340] in

[0341] R 1 、R 3 、R 5 and R 6 has the meaning as defined in any of the above aspects;

[0342] R 7 represents R as defined in any of the aspects described above 2 the same or different substituents;

[0343] R 8 represents R as defined in any of the aspects described above 4 the same or different substituents;

[0344] n represents an integer of 0, 1 or 2, preferably 0 or 1;

[0345] m represents an integer of 0, 1 or 2, preferably 1 or 2.

[0346] According to a preferred embodiment of aspect 9, the present invention relates to compounds of formula (Iv) as defined above.

[0347] According to a further preferred embodiment of aspect 9, the present invention relates to compounds of formula (I-vi) as defined above.

[0348] According to a preferred embodiment of aspect 9, the present invention relates to compounds of formula (I-vii) as defined above.

[0349] In another aspect (Aspect 10), the present invention relates to compounds of formula (I) as described in any of the above aspects, and salts and N-oxides thereof, characterized in that they have a structure according to one of formulas (I-viii), (I-ix), (Ix), (I-xi) and (I-xii).

[0350]

[0351] in

[0352] R 1 、R 3 、R 5 and R 6 has the meaning as defined in any of the above aspects;

[0353] R 7 represents R as defined in any of the aspects described above 2 the same or different substituents;

[0354] R 8 represents R as defined in any of the aspects described above 4 the same or different substituents;

[0355] n represents an integer of 0, 1 or 2, preferably 0 or 1;

[0356] m represents an integer of 0, 1 or 2, preferably 1 or 2.

[0357] According to a preferred embodiment of aspect 10, the present invention relates to compounds of formula (I-viii) as defined above.

[0358] According to a further preferred embodiment of aspect 10, the present invention relates to compounds of formula (I-ix) as defined above.

[0359] According to a preferred embodiment of aspect 10, the present invention relates to compounds of formula (Ix) as defined above.

[0360] According to a preferred embodiment of aspect 10, the present invention relates to compounds of formula (I-xi) as defined above.

[0361] According to a preferred embodiment, aspect 10 of the present invention relates to compounds of formula (I-xii), (I-xiii), (I-xiv), (I-xv), (I-xvi), (I-xvii), (I-xviii) or (I-xix), and salts and N-oxides thereof

[0362]

[0363]

[0364] in

[0365] R 1 、R 3 、R 5 and R 6 has the meaning as defined in any of the above aspects;

[0366] R 7 represents R as defined in any of the aspects described above 2 the same or different substituents;

[0367] R 8 represents R as defined in any of the aspects described above 4 the same or different substituents;

[0368] R 81 represents in each case optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C3-haloalkyl, hydroxy-C2-C4-alkyl, -CO2C1-C4-alkyl, -C(=NOC1-C4-alkyl)H, -C(=NOC1-C4-alkyl)-C1-C4-alkyl, wherein the aforementioned optionally substituted groups are optionally replaced by up to 3 substituents wherein the substituents are independently selected from 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;

[0369] or represents a 3- to 6-membered heterocyclic group containing 1 or 2 heteroatoms selected from N, O and S, wherein the 3- to 6-membered heterocyclic group may optionally carry 1, 2, 3 or 4 substituents independently 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 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, C1-C3 cyanoalkylsulfonyl;

[0370] R 81 Preferably 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;

[0371] R 81 More preferably represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, difluoroethyl, trifluoroethyl, cyanomethyl, cyanoethyl, 2-hydroxyethyl, -COOCH3 or -COOCH2CH3,

[0372] R 81 Particularly preferably represents a methyl or ethyl group,

[0373] m represents an integer of 0, 1 or 2, preferably 1 or 2.

[0374] According to a preferred embodiment of aspect 10, the present invention relates to compounds of formula (I-xii) as defined above.

[0375] According to a further preferred embodiment of aspect 10, the present invention relates to compounds of formula (I-xiii) as defined above.

[0376] According to a preferred embodiment of aspect 10, the present invention relates to compounds of formula (I-xiv) as defined above.

[0377] According to a preferred embodiment of aspect 10, the present invention relates to compounds of formula (I-xv) as defined above.

[0378] According to a further preferred embodiment of aspect 10, the present invention relates to compounds of formula (I-xvi) as defined above.

[0379] According to a preferred embodiment of aspect 10, the present invention relates to compounds of formula (I-xvii) as defined above.

[0380] According to a preferred embodiment of aspect 10, the present invention relates to compounds of formula (I-xviii) as defined above.

[0381] According to a preferred embodiment of aspect 10, the present invention relates to compounds of formula (I-xix) as defined above.

[0382] According to one embodiment, the invention relates to compounds of formula (I) as described in the various aspects and embodiments herein, wherein R 5 represents hydrogen and the other substituents may have any meanings described herein.

[0383] According to one embodiment, the invention relates to compounds of formula (I) as described in the various aspects and embodiments herein, wherein R 6 does not represent hydrogen and the other substituents may have any meaning described herein.

[0384] Another aspect of the present invention (Aspect 11) relates to intermediate compounds according to Formula IX-1, X or XIII, wherein R 3 、R 4 、R 5 and R 6 has the meaning as defined above in any aspect of the invention.

[0385]

[0386] Particularly preferred are the compounds according to the Examples hereinafter.

[0387] definition

[0388] Those skilled in the art know that, if not explicitly stated, the expressions "a" or "an" as used in this application may mean "one (1)", "one (1) or more" or "at least one (1)" depending on the circumstances.

[0389] For all structures described herein, such as ring systems and groups, adjacent atoms cannot be -OO- or -OS-.

[0390] Structures with a variable number of possible carbon atoms (C atoms) may be referred to in this application as C 碳原子的下限 -C 碳原子的上限 Structure (C LL -C UL Example: an alkyl group may consist of 3 to 10 carbon atoms and in this case corresponds to a C3-C 10 Alkyl. A ring structure composed of carbon atoms and heteroatoms can be referred to as a "LL to UL membered" structure. An example of a 6-membered ring structure is toluene (a 6-membered ring structure substituted with a methyl group).

[0391] If the collective term for substituents (e.g. C LL -C UL Alkyl) is located in a composite substituent (e.g. C LL -C UL Cycloalkyl-C LL -C UL alkyl) at the end of the composite substituent, then the component at the starting end of the composite substituent (e.g. C LL -C ULCycloalkyl) may be identically or differently and independently substituted by subsequent substituents (e.g. C LL -C UL All collective terms used in this application for chemical groups, ring systems and cyclic groups can be replaced by adding "C LL -C UL ” or “LL- to UL-element” and is more specifically specified.

[0392] In the definitions of the symbols given in the above formulae, collective terms are used which generally represent the following substituents:

[0393] Halogen refers to elements of main group 7, preferably fluorine, chlorine, bromine and iodine, more preferably fluorine, chlorine and bromine, and even more preferably fluorine and chlorine.

[0394] Examples of heteroatoms are N, O, S, P, B, Si. Preferably, the term "heteroatom" relates to N, S and O.

[0395] According to the invention, “alkyl” (on its own or as part of a chemical group) represents a straight-chain or branched hydrocarbon preferably having 1 to 6 carbon atoms, for example 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. Also preferred are alkyl radicals having 1 to 4 carbon atoms, such as, in particular, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl. The alkyl radicals according to the invention may be substituted by one or more identical or different radicals.

[0396] According to the invention, “alkenyl” (on its own or as part of a chemical group) represents a straight-chain or branched hydrocarbon preferably having 2 to 6 carbon atoms and at least one double bond, for example ethenyl, 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-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 Alkenyl of the present invention may be substituted with one or more identical or different groups.

[0397] According to the invention, "alkynyl" (on its own or as part of a chemical group) represents a straight-chain or branched hydrocarbon preferably having 2 to 6 carbon atoms and at least one triple bond, for example 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- Alkynyl, 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-hexadiynyl.Also preferred are alkynyls with 2 to 4 carbon atoms, such as especially ethynyl, 2-propynyl or 2-butynyl-2-propenyl.Alkynyl of the present invention may be substituted by one or more identical or different groups.

[0398] According to the invention, "cycloalkyl" (either by itself or as part of a chemical group) represents a monocyclic, bicyclic or tricyclic hydrocarbon preferably having 3 to 10 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl or adamantyl. Also preferred are cycloalkyl groups having 3, 4, 5, 6 or 7 carbon atoms, such as, in particular, cyclopropyl or cyclobutyl. The cycloalkyl groups according to the invention may be substituted by one or more identical or different groups.

[0399] According to the invention, "alkylcycloalkyl" represents a monocyclic, bicyclic or tricyclic alkylcycloalkyl group preferably having 4 to 10 or 4 to 7 carbon atoms, for example methylcyclopropyl, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. Also preferred are alkylcycloalkyl groups having 4, 5 or 7 carbon atoms, such as, in particular, ethylcyclopropyl or 4-methylcyclohexyl. The alkylcycloalkyl groups according to the invention may be substituted by one or more identical or different radicals.

[0400] According to the invention, "cycloalkylalkyl" represents a monocyclic, bicyclic or tricyclic cycloalkylalkyl group preferably having 4 to 10 or 4 to 7 carbon atoms, for example cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and cyclopentylethyl. Also preferred are cycloalkylalkyl groups having 4, 5 or 7 carbon atoms, such as, in particular, cyclopropylmethyl or cyclobutylmethyl. The cycloalkylalkyl groups according to the invention may be substituted by one or more identical or different radicals.

[0401] According to the present invention, "hydroxyalkyl" represents a linear or branched alcohol preferably having 1 to 6 carbon atoms, for example methanol, ethanol, n-propanol, isopropanol (isopropan-2-ol), n-butanol, isobutanol, sec-butanol and tert-butanol. Also preferred are hydroxyalkyl groups having 1 to 4 carbon atoms. The hydroxyalkyl groups according to the invention may be substituted by one or more identical or different groups.

[0402] According to the present invention, "alkoxy" represents a straight-chain or branched O-alkyl group preferably having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy. Alkoxy groups having 1 to 4 carbon atoms are also preferred. The alkoxy groups according to the present invention may be substituted by one or more identical or different groups.

[0403] According to the present invention, "cycloalkoxy" represents -O-cycloalkyl, where cycloalkyl has the meaning as defined above. Preference is given to cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms, i.e. in particular -O-cyclopropyl, -O-cyclobutyl, -O-cyclopentyl, -O-cyclohexyl, -O-cycloheptyl. The cycloalkoxy groups according to the present invention may be substituted by one or more identical or different groups, preferably selected from the group consisting of halogen optional substituents.

[0404] According to the present invention, "alkylthio" or "alkylsulfanyl" represents a linear or branched S-alkyl group preferably having 1 to 6 carbon atoms, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio and tert-butylthio. Alkylthio groups having 1 to 4 carbon atoms are also preferred. The alkylthio groups according to the present invention may be substituted by one or more identical or different groups.

[0405] According to the present invention, "alkylsulfinyl" represents a straight-chain or branched alkylsulfinyl group preferably having 1 to 6 carbon atoms, for example methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl and tert-butylsulfinyl. Also preferred are alkylsulfinyl groups having 1 to 4 carbon atoms. The alkylsulfinyl groups according to the present invention may be substituted by one or more identical or different groups.

[0406] According to the present invention, "alkylsulfonyl" represents a straight-chain or branched alkylsulfonyl group preferably having 1 to 6 carbon atoms, for example methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl and tert-butylsulfonyl. Also preferred are alkylsulfonyl groups having 1 to 4 carbon atoms. The alkylsulfonyl groups according to the present invention may be substituted by one or more identical or different groups.

[0407] According to the invention, "cycloalkylsulfonyl" represents a monocyclic, bicyclic or tricyclic cycloalkylsulfonyl group preferably having 4 to 10 or 4 to 7 carbon atoms, such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl and cyclohexylsulfonyl. Also preferred are cycloalkylsulfonyl groups having 4, 5 or 7 carbon atoms, such as especially cyclopropylsulfonyl or cyclobutylsulfonyl. The cycloalkylsulfonyl groups according to the invention may be substituted by one or more identical or different radicals.

[0408] As used herein, the term "alkylcarbonyl" represents a linear or branched alkyl-C(=O) group preferably having 2 to 7 carbon atoms, such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, sec-butylcarbonyl and tert-butylcarbonyl. Also preferred are alkylcarbonyl groups having 1 to 4 carbon atoms. Alkylcarbonyl groups may be substituted with one or more identical or different groups.

[0409] As used herein, the term "alkoxycarbonyl" (alone or as part of a chemical group) represents a straight-chain or branched alkoxycarbonyl group preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkoxy moiety, for example methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, sec-butoxycarbonyl and tert-butoxycarbonyl. The alkoxycarbonyl group may be substituted by one or more identical or different groups.

[0410] As used herein, the term "alkylaminocarbonyl" represents a straight-chain or branched alkylaminocarbonyl group preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl portion, for example, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, sec-butylaminocarbonyl and tert-butylaminocarbonyl. The alkylaminocarbonyl group may be substituted by one or more identical or different groups.

[0411] If used in this document, the term " N,N "-dialkylaminocarbonyl" represents a straight or branched chain preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl portion N,N -dialkylaminocarbonyl groups, for example N,N -dimethylaminocarbonyl, N,N -diethylaminocarbonyl, N,N -di(n-propylamino)carbonyl, N,N -di(isopropylamino)carbonyl and N,N -di-(sec-butylamino)carbonyl. N,N A dialkylaminocarbonyl group may be substituted by one or more identical or different groups.

[0412] Typically, the term "aryl" represents a monocyclic, bicyclic or polycyclic aromatic system preferably having 6 to 14, particularly 6 to 10, ring carbon atoms, such as phenyl, naphthyl, anthracenyl, phenanthrenyl, preferably phenyl. Aryl can also represent a polycyclic system, including fused polycyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenyl, wherein the bonding point is on the aromatic system. A fused polycyclic system has at least two fused rings, wherein the two fused rings share two adjacent atoms (or, in other words, the rings share a covalent bond). Phenyl is preferred. The aryl groups of the present invention, especially phenyl groups, can be substituted by one or more identical or different groups.

[0413] The term "polycyclic" ring according to the present invention refers to fused, bridged and spirocyclic carbocyclic and heterocyclic rings as well as ring systems connected by single or double bonds.

[0414] According to the invention, "heterocycle", "heterocyclic ring" or "heterocyclic ring system" means a carbocyclic ring system having at least one ring in which at least one carbon atom is replaced by a heteroatom, preferably by a heteroatom selected from N, O, S, P, B, Si, Se, and the ring is saturated, unsaturated or heteroaromatic and may be unsubstituted or substituted, wherein the point of bonding is located on a ring atom. Unless defined differently, the heterocycle contains 3 to 12 ring atoms, preferably 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and contains one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocycle, which are preferably selected from N, O and S, although no two oxygen atoms are directly adjacent. The heterocycle usually contains not more than 4 nitrogen atoms and / or not more than 2 oxygen atoms and / or not more than 2 sulfur atoms. Non-aromatic heterocycles are generally referred to herein as "saturated or unsaturated heterocycles". When a heterocyclyl group or a heterocycle is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, the invention also includes polycyclic ring systems, for example 8-azabicyclo[3.2.1]octanyl, 1-azabicyclo[2.2.1]heptyl, 1-oxa-5-azaspiro[2.3]hexyl or 2,3-dihydro-1 H -indole. In the case of optionally substituted heterocyclyl, the invention also includes spirocyclic systems, for example 1-oxa-5-azaspiro[2.3]hexyl.

[0415] Preferred heterocyclic groups of the present invention are, for example, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, thiazolidinyl, oxazolidinyl, dioxolanyl, dioxolenyl, pyrazolidinyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, oxirane, azetidinyl, aziridine, oxazetidinyl, oxaziridine, oxazepanyl, oxazinyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl, oxomorpholinyl, oxopiperazinyl and oxepanyl. Most preferred are oxetanyl, tetrahydropyranyl and piperazinyl.

[0416] Of particular importance are heteroaryl groups, i.e. heteroaromatic systems. According to the invention, the term heteroaryl represents heteroaromatic compounds, i.e. fully unsaturated aromatic heterocyclic compounds that fall within the above definition of heterocycle. For clarification, if the definition of a substituent in this document includes "heterocycle" (or "heterocyclyl") as well as "heteroaryl" (or "heteroaromatic"), this means that the term "heterocycle" (or "heterocyclyl") does not include "heteroaryl" (or "heteroaromatic") groups, so as to avoid overlapping definitions. Preferred are 5- to 7-membered rings, more preferably 6- or 6-membered rings, which have 1 to 3, preferably 1 or 2, identical or different heteroatoms from the above groups. Heteroaryl groups according to the invention are, 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, azepine, pyrrolyl, pyridinyl, 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, thiepineyl, 1,2,4-triazolone and 1,2,4-diazacyclopentinyl. Preferred are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyrazolyl, pyrrolyl, thiazolyl, oxazolyl, isothiazolyl, and isoxazolyl. More preferred are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyrazolyl, pyrrolyl, and thiazolyl. The heteroaryl groups of the present invention may also be substituted with one or more identical or different groups.

[0417] The term "optionally substituted at each occurrence" means that groups / substituents such as alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl groups etc. may be substituted, meaning, for example, a substituted group derived from an unsubstituted base structure, wherein the substituents (e.g. one (1) substituent or a plurality of substituents, preferably 1, 2, 3, 4, 5, 6 or 7 substituents, more preferably 1, 2, 3 or 4 substituents, more preferably 1, 2 or 3 substituents, even more preferably 1 or 2 substituents) are independently selected from amino, hydroxy, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C1-C4 carboxyl, carbonamide, 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-, C 10 -、C 14 -aryloxycarbonyl, C1-C4alkanoyl, C2-C4alkenylcarbonyl, C2-C4alkynylcarbonyl, C6-, C 10 -、C 14 -arylcarbonyl, C1-C4 alkylthio, C1-C4 haloalkylthio, C3-C4 cycloalkylthio, C2-C4 alkenylthio, C5-C6 cycloalkenylthio, C2-C4 alkynylthio, C1-C4 alkylsulfinyl (including both enantiomers of C1-C4 alkylsulfinyl), C1-C4 haloalkylsulfinyl (including both enantiomers of C1-C4 haloalkylsulfinyl), C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, N -mono-C1-C4 alkylaminosulfonyl, N,N -di-C1-C4 alkylaminosulfonyl, C1-C4 alkylphosphinyl, C1-C4 alkylphosphinyl (including C1-C4 alkylphosphinyl and two enantiomers of C1-C4 alkylphosphinyl), N -C1-C4 alkylaminocarbonyl, N,N -di-C1-C4 alkylaminocarbonyl, N-C1-C4 alkanoylaminocarbonyl, N-C1-C4 alkanoyl-N-C1-C4 alkylaminocarbonyl, C6-, C 10 -、C 14 -aryl, C6-, C10 -、C 14 -aryloxy, benzyl, benzyloxy, benzylthio, C6-, C 10 -、C 14 -Arylthio, C6-, C 10 -、C 14 -arylamino, benzylamino, heterocyclic and trialkylsilyl ((C1-C4 alkyl)3-silyl), double-bonded substituents such as C1-C4 alkylene (e.g., methylene or ethylene), oxo, imino, and substituted imino groups. When two or more groups form one or more rings, these may be carbocyclic, heterocyclic, saturated, partially saturated, or unsaturated, and may include, for example, aromatic rings and be further substituted. The substituents mentioned as examples ("first substituent group") may (if they contain a hydrocarbon-containing component) optionally be further substituted therein ("second substituent group"), for example, with 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" group preferably includes only one or two substituent groups.

[0418] The chemical group or the halo group (such as alkyl, cycloalkyl, alkoxy, alkylthio, alkyl sulfinyl or alkyl sulfonyl etc.) of halogen replacement of the present invention are substituted by halogen or polysubstituted, up to the maximum possible number of substituents. Such group is also referred to as halo group (such as haloalkyl, halogenated cycloalkyl, haloalkoxy, haloalkylthio, haloalkyl sulfinyl or haloalkyl sulfonyl etc.). When substituted by halogen, the halogen atom can be identical or different, and can all be bonded to a carbon atom or can be bonded to multiple carbon atoms. Halogen is particularly fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, and more preferably fluorine or chlorine, even more preferably fluorine. More specifically, the halogen-substituted group is a monohalocycloalkyl such as 1-fluorocyclopropyl, 2-fluorocyclopropyl or 1-fluorocyclobutyl, a monohaloalkyl such as 2-chloroethyl, 2-fluoroethyl, 1-chloroethyl, 1-fluoroethyl, chloromethyl or fluoromethyl; a perhaloalkyl such as trichloromethyl or trifluoromethyl or CF2CF3, a polyhaloalkyl such as difluoromethyl, 2-fluoro-2-chloroethyl, dichloromethyl, 1,1,2,2-tetrafluoroethyl or 2,2,2-trifluoroethyl. Other 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 tert-butyl. Preference is given to haloalkyl radicals 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. Particular preference is given to haloalkyl radicals having 1 or 2 carbon atoms and 1 to 5, identical or different, halogen atoms selected from fluorine and chlorine, such as, in particular, difluoromethyl, trifluoromethyl or 2,2-difluoroethyl.Other examples of halogen-substituted compounds are haloalkoxy groups such as OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3, OCH2CHF2 and OCH2CH2Cl; haloalkylsulfanyl groups such as difluoromethylsulfanyl, trifluoromethylsulfanyl, trichloromethylsulfanyl, chlorodifluoromethylsulfanyl, 1-fluoroethylsulfanyl, 2-fluoroethylsulfanyl, 2,2-difluoroethylsulfanyl, 1,1,2,2-tetrafluoroethylsulfanyl, 2,2,2-trifluoroethylsulfanyl or 2-chloro-1,1,2-trifluoroethylsulfanyl; haloalkylsulfinyl groups such as difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfin ... fluoromethylsulfinyl, 1-fluoroethylsulfinyl, 2-fluoroethylsulfinyl, 2,2-difluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and 2-chloro-1,1,2-trifluoroethylsulfinyl; halogenated alkylsulfonyl 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.

[0419] The cyano-substituted chemical groups of the present invention (e.g., alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfinyl, or alkylsulfonyl, etc.) are preferably monosubstituted with a cyano group. Such cyano-substituted groups are also referred to as cyano groups (e.g., cyanoalkyl, cyanocycloalkyl, cyanoalkoxy, cyanoalkylthio, cyanoalkylsulfinyl, cyanoalkylsulfonyl, etc.). If the number of carbon atoms in such a cyano group is specified, e.g., C LL - UL If the cyanoalkyl group is present, the carbon atom of the cyano group will not be counted; for example, C 1-3 The cyanoalkyl group includes a cyanopropyl group.

[0420] In the case of groups having carbon atoms, preference is given to those having 1 to 4 carbon atoms, especially 1 or 2 carbon atoms. Substituents selected from the group consisting of halogen, such as 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 generally preferred. Particularly preferred are the substituents methyl, methoxy, fluorine, chlorine, bromine and cyano.

[0421] Substituted amino (e.g. monosubstituted or disubstituted amino) means a radical from a substituted amino group which is N-substituted, for example substituted by one or two identical or different radicals selected from alkyl, hydroxy, amino, alkoxy, acyl and aryl; preferably N-monoalkylamino and N,N-dialkylamino (e.g. 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 (e.g. N-methoxy The present invention also includes methylamino, N-methoxyethylamino, N,N-di(methoxymethyl)amino or N,N-di(methoxyethyl)amino), N-monoarylamino and N,N-diarylamino groups, such as optionally substituted aniline, acylamino, N,N-diacylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino, and saturated N-heterocycles; preference is given to alkyl groups having 1 to 4 carbon atoms; aryl is preferably phenyl or substituted phenyl; for acyl, the definition given further below applies, preferably (C1-C4)-alkanoyl. The same applies to substituted hydroxyamino or hydrazine groups.

[0422] Substituted amino groups also include quaternary ammonium compounds (salts) having four organic substituents on the nitrogen atom.

[0423] Optionally substituted phenyl is preferably unsubstituted phenyl or phenyl which is monosubstituted or polysubstituted, preferably up to trisubstituted, by the same or different groups 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) alkyl Sulfinyl, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, cyano, isocyano and nitro, for example o-, m- and p-tolyl, dimethylphenyl, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-fluorophenyl, 2-, 3- and 4-trifluoromethylphenyl and 4-trichloromethylphenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl, 4-heptafluorophenyl.

[0424] Optionally substituted cycloalkyl is preferably unsubstituted cycloalkyl or cycloalkyl which is mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals selected from the group consisting of halogen, cyano, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)haloalkyl and (C1-C4)haloalkoxy, in particular substituted by one or two (C1-C4)alkyl radicals.

[0425] The compounds of the present invention may be present in preferred embodiments. The various embodiments described herein may be combined with one another. Combinations that violate the laws of nature and that would be excluded by a person skilled in the art based on his / her expertise are not included. For example, ring structures having three or more adjacent oxygen atoms are excluded.

[0426] Isomers

[0427] Depending on the nature of the substituents, the compounds of formula (I) may be in the form of geometric isomers and / or optically active isomers or corresponding isomer mixtures of varying composition. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Therefore, the present invention encompasses both the pure stereoisomers and any mixtures of these isomers.

[0428] Methods and uses

[0429] The present invention further relates to a method for controlling animal pests, wherein a compound of formula (I) is applied to the animal pests and / or their habitat. The control of animal pests is preferably carried out in agriculture and forestry, as well as in the protection of materials. Surgery or therapeutic treatment methods performed on the human or animal body, as well as diagnostic methods performed on the human or animal body, are preferably excluded herein.

[0430] The invention further relates to the use of the compounds of the formula (I) as pesticides, in particular crop protection agents.

[0431] In the context of this application, the term "pesticide" always also includes the term "crop protection agent" in each case.

[0432] The compounds of the formula (I) having good plant tolerance, favorable homeothermic animal toxicity and good environmental compatibility are suitable for protecting plants and plant organs against biotic and abiotic stress factors, increasing harvest yield, improving the quality of harvested material and controlling animal pests encountered in agriculture, horticulture, animal husbandry, aquaculture, forestry, gardening and leisure facilities, protection of stored products and materials, and in the hygiene sector, in particular insects, arachnids, helminths, in particular nematodes and molluscs.

[0433] In the context of this patent application, the term "hygiene" is understood to mean any and all measures, methods and practices intended to prevent diseases, in particular infectious diseases, and to protect human and animal health and / or the environment and / or to maintain cleanliness. According to the present invention, this includes in particular measures for cleaning, disinfecting and sterilizing surfaces such as textiles or hard surfaces, in particular glass, wood, cement, porcelain, ceramics, plastics or also metals, and for ensuring that these surfaces are free of hygienic pests and / or their secretions. In this regard, the scope of the present invention preferably excludes surgical or therapeutic treatment methods applied to the human or animal body, as well as diagnostic methods performed on the human or animal body.

[0434] The term "hygiene sector" therefore covers all areas, technical fields and industrial applications in which these hygiene measures, methods and practices are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, hospitals, stables, animal husbandry, etc.

[0435] The term "hygiene pest" is therefore understood to mean one or more animal pests whose presence in the sanitary sector is problematic, particularly for health reasons. Therefore, the primary objective is to prevent or minimize the presence of and / or contact with sanitary pests in the sanitary sector. This can be achieved, in particular, by applying pesticides, which can be used both to prevent infestations and to treat existing infestations. Formulations that prevent or reduce contact with pests can also be used. Hygiene pests include, for example, the organisms mentioned below.

[0436] The term "hygiene protection" therefore covers all actions that maintain and / or improve these hygiene measures, methods and practices.

[0437] The compounds of formula (I) can preferably be used as insecticides. They are active against normally sensitive and resistant species and against all or some developmental stages. The pests mentioned above include:

[0438] Pests from the phylum Arthropoda, in particular 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., for example Brevipalpus sphoenicis; Bryobia graminum; Bryobia praetiosa; Centruroides spp.; Chorioptes spp.; Dermanyssus gallinae; Dermatophagoides pteronyssinus; Dermatophagoides farinae; Dermacentor spp.; Eotetranychus spp., for example, Eotetranychus shicoriae and Epitrimerus pyri; Eutetranychus spp., for example, Eutetranychus banksi; Eriophyes spp., for example, Eriophyes pyri; Glycyphagus domesticus); Halotydeus destructor; Hemitarsonemus spp., for example Hemitarsonemus latus (= Polyphagotarsonemus latus); Hyalomma spp.; Ixodes spp.; Latrodectus spp.; Loxosceles spp.); Neutrombicula autumnalis; Nuphersa spp.; Oligonychus spp., for example, Oligonychus coffeae, Oligonychus coniferarum, Oligonychus silicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi; Ornithodorus spp.; Ornithonyssus spp.; Panonychus spp., for example, Panonychus citri (= Metatetranychus citri) citri), Panonychus ulmi (= Metatetranychus ulmi); Phyllocoptruta oleivora; Platytetranychus multidigituli; Polyphagotarsonemus latus; Psoroptes spp.; Rhipicephalus spp.; Rhizoglyphus spp.; Sarcoptes spp.; Scorpio maurus; Steneotarsonemus spp.; Steneotarsonemus spinki; Tarsonemus spp., for example Tarsonemus confusus), Tarsonemus pallidus; Tetranychus spp., such as Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae; Trombicula alfreddugesi; Vaejovis spp.); Tomato gall mite (Vasates lycopersici);.

[0439] Pests from the class Chilopoda, such as Geophilus spp. and Scutigera spp.;

[0440] Pests from the order Collembola or class Collembola, for example, Onychiurus sarmatus and Sminthurus viridis;

[0441] Pests from the class Diplopoda, such as the millipede (Blaniulus guttulatus);

[0442] pests from the class Insecta, for example from the order Blattodea, for example, the Oriental cockroach (Blatta orientalis); the Asian cockroach (Blattella asahinai); the German cockroach (Blattella germanica); the Madeira cockroach (Leucophaea maderae); Lobopteradecipiens; the house cockroach (Neostylopyga rhombifolia); the Cuban cockroach (Panchlora spp.); the cockroach (Parcoblatta spp.); the Periplaneta spp., for example, the American cockroach (Periplaneta americana), the Australian cockroach (Periplaneta australasiae); the Surinam cockroach (Pycnoscelus surinamensis); the brown-banded cockroach (Supella longipalpa);

[0443] Pests from the order Coleoptera, for example, the striped squash beetle (Acalymma vittatum); the bean weevil (Acanthoscelides obtectus); the Adoretus spp.; the small honeycomb beetle (Aethinatumida); the cottonwood leaf beetle (Agelastica alni); the narrow beetle (Agrilus spp.), for example, the narrow ash beetle (Agrilus planipennis), the narrow chestnut beetle (Agrilus coxalis), the chestnut two-lined beetle (Agrilus bilineatus), the birch copper beetle (Agrilus anxius); the Agriotes spp., for example, the straight-striped click beetle (Agriotes linneatus), the wheat wireworm (Agriotes mancus); the black fungus beetle (Alphitobius diaperinus); the potato beetle (Amphimallon solstitialis); the furniture beetle (Anobium punctatum; Anoplophora spp., for example, Anoplophora glabripennis; Anthonomus spp., for example, Anthonomus grandis; Anthrenus spp.; Apion spp.; Apogonia spp.; Atomaria spp., for example, Atomaria linearis; Attagenus spp.; Baris caerulescens; Bruchidius obtectus; Bruchus spp., for example, Bruchus pisorum and Bruchus rufimanus; Cassida spp.); bean leaf beetles (Cerotoma trifurcata); Ceuthorrhynchus spp., such as Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, and Ceutorrhynchus rapae; Chaetocnema spp.), such as the sweet potato flea beetle (Chaetocnema confinis), the American tooth flea beetle (Chaetocnema denticulata), and the wasteland corn flea beetle (Chaetocnema ectypa); Cleonus mendicus; Conoderus spp.; Cosmopolites spp., such as the banana weevil (Cosmopolites sordidus); Costelytra zealandica; Ctenicera spp.; Curculio spp., such as the walnut weevil (Curculio caryae), the large chestnut weevil (Curculio caryatrypes), the American hazelnut weevil (Curculioobtusus), and the small chestnut weevil (Curculio sayi); Cryptolestes spp. ferrugineus; long-horned flat grain beetle (Cryptolestespus illus); poplar stem weevil (Cryptorhynchus lapathi); mango pit weevil (Cryptorhynchus mangiferae); twig weevil (Cylindrocopturus spp.); dense-spotted twig weevil (Cylindrocopturus adspersus); pine twig weevil (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, Diabrotica virgifera zeae; Dichocrocis spp.; Dicladispa armigera; Diloboderus spp.; Epicaerus spp.; Epilachna spp.), such as the squash beetle (Epilachna borealis) and the Mexican bean beetle (Epilachna varivestis); Epitrix spp., such as the cucumber flea beetle (Epitrix cucumeris), the eggplant leaf beetle (Epitrix fuscula), the tobacco flea beetle (Epitrix hirtipennis), the American potato flea beetle (Epitrix subcrinita), and the tuber flea beetle (Epitrix tuberis); borers (Faustinus spp.); the naked spider beetle (Gibbium psylloides); the broad-horned flour beetle (Gnathocerus cornutus); the cabbage borer (Hellulaundalis); the black sugarcane beetle (Heteronychus arator); the Heteronyx spp.; the Hylamorpha elegans; the North American longhorn beetle (Hylotrupes bajulus); the purple clover leaf beetle (Hypera postica; Hypomeces squamosus; Hypothenemus spp., for example, Hypothenemushampei, Hypothenemus obscurus, and Hypothenemus pubescens; Lachnosterna consanguinea; Lasioderma serricorne; Latheticus oryzae; Lathridius spp.; Lema spp.; Leptinotarsa decemlineata; Leucoptera spp., for example, Leucoptera coffee leafminer; Limonius ectypus, Lissorhoptrus spp. oryzophilus; Listronotus (=Hyperodes) spp.; Lixus spp.; Luperodes spp.; Luperomorpha xanthodera; Lyctus spp.; Megacyllene spp., for example, Megacyllene obiniae; Megascelis spp.); Melanotus spp., for example, Melanotus longulus oregonensis; Meligethes aeneus; Melolontha spp., for example, Melolontha melolontha; Migdolus spp.; Monochamus spp.; Naupactus xanthographus; Necrobia spp.; Neogalerucella spp.; Niptus hololeucus; Oryctes rhinoceros; Oryzaephilus surinamensis, Oryzaphagus oryzae; Otiorrhynchus spp.), for example, Otiorhynchus cribricollis (apple ear beak), Otiorhynchus ligustici (large clover ear beak), Otiorhynchus ovatus (large clover ear beak), Otiorhynchus rugosostriarus (rough strawberry ear beak), Otiorhynchus sulcatus (black grape ear beak); Oulema spp., for example, Oulema melanopus (black horned mud beetle), Oulema oryzae (rice mud beetle); Oxycetonia jucunda (small blue beetle); Phaedon cochleariae (horseradish monkey leaf beetle); Phyllophaga spp.; Phyllophaga helleri (gill beetle); Phyllotreta spp. spp.), such as the horseradish flea beetle (Phyllotreta armoraciae), the western black flea beetle (Phyllotreta pusilla), the beautiful striped flea beetle (Phyllotreta ramosa), and the yellow-striped flea beetle (Phyllotretastriolata); the Japanese beetle (Popillia japonica); the Andean potato weevil (Premnotrypes spp.); the large grain borer (Prostephanus truncatus); the flea beetle (Psylliodes spp.), for example, potato flea beetle (Psylliodes affinis), rapeseed flea beetle (Psylliodes chrysocephala), and hop flea beetle (Psylliodes punctulata); spider beetles (Ptinus spp.); dusky ladybugs (Rhizobius ventralis); grain borers (Rhizopertha dominica); cryptognathus spp.; red palm weevils (Rhynchophorus ferrugineus); palm weevils (Rhynchophorus palmarum); Scolytus spp., for example, European elm weevil (Scolytus multistriatus); Sinoxylon perforans; Sitophilus spp., for example, wheat weevils (Sitophilus granarius), tamarind weevils (Sitophilus linearis), Sitophilus oryzae, Sitophilus zeamais; Sphenophorus spp.; Stegobium paniceum; Sternechus spp., for example, Sternechus paludatus; Symphyletes spp.; Tanymecus spp., for example, Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus; Tenebriomolitor; Tenebrioides mauretanicus; Tribolium spp., for example, Tribolium audax, Tribolium rubrum, Tribolium truncatum ... castaneum), Tribolium confusum; Trogoderma spp.; Tychius spp.; Xylotrechus spp.; Zabrus spp., such as the corn beetle (Zabrus tenebrioides);

[0444] Pests from the order Dermaptera, such as Anisolabis maritime, Forficula auricularia, and Labidura riparia;

[0445] Pests from the order of 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 gambiae; Asphondylia spp.; Bactrocera spp.), for example, Bactrocera cucurbitae, Bactrocera adorsalis, Bactrocera oleae; Bibio hortulanus; Calliphora erythrocephala; Calliphora vicina; Ceratitis capitata; Chironomus spp., Chrysomya spp.; Chrysops spp.; Chrysozona pluvialis; Cochliomyia spp.; Contarinia spp., for example, Contarinia johnsoni, Contarinia nasturtii, Contarinia spp. pyrivora), sunflower gall midge (Contarinia schulzi), sorghum gall midge (Contariniasorghicola), wheat midge (Contariniatritici); Cordylobia anthropophaga, Cricotopus sylvestris; Culex spp., such as Culex pipiens and Culex quinquefasciatus; Culicoides spp.; Culiseta 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, Drosphila melanogaster, Drosophila suzukii; Echinocnemus spp.; Euleia heraclei; Fannia spp.; Gasterophilus spp.; Glossina spp.); Haematopotas spp.; Hydrellia spp.; Hydrellia griseola; Hylemya spp.; Hippobosca spp.; Hypoderma spp.; Liriomyza spp., for example, Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae; Lucilia spp., for example, Lucilia cuprina; Lutzomyia spp.; Mansonia spp.; Musca 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.; Piophila casei; Platyparea poeciloptera; Prodiplosis spp.; Psilarosae (carrot stem fly); Rhagoletis spp., for example, Rhagoletis cingulata (cherry fruit fly), Rhagoletis completa (walnut fruit fly), Rhagoletis fausta (black cherry fruit fly), Rhagoletis indifferens (European sweet cherry fruit fly), Rhagoletis simendax (blueberry fruit fly), Rhagoletis pomonella (apple fruit fly); Sarcophaga spp.; Simulium spp., for example, Simulium meridionale (southern fruit fly); Stomoxys spp.); Tabanus spp.; Tetanops spp.; Tipula spp., such as Tipula paludosa and Tipula simplex; and Toxotrypana curvicauda.

[0446] Pests from the order Hemiptera, for example Acizzia acaciae baileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiphon spp., for example Acyrthosiphon pisum; Acrogonia spp.; Aeneolamia spp.; Agonascena spp.; Aleurocanthus spp.; Aleyrodes proletella; Aleurolobus barodensis; Aleurothrixus floccosus; Allocaridaramalayensis; Amrasca spp. spp.), for example, Amrasca bigutulla, Amrasca cadevastans; Anuraphis cardui; Aonidiella spp., for example, Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata; Aphanostigmapiri; Aphis spp., for example, Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis shederae, Aphis illinoisensis, Aphis spp. middletoni), buckthorn potato aphid (Aphis nasturtii), oleander aphid (Aphis nerii), apple aphid (Aphis pomi), spiraea aphid (Aphisspiraecola), viburnum aphid (Aphis viburniphila); grape sawfly (Arboridia apicalis); Arytainilla spp.; Aspidiella spp.); Aspidiotus spp., for example, Aspidiotus nerii; Atanus spp.; Aulacorthum solani; Bemisia tabaci; Blastopsylla occidentalis; Boreoglycaspis melaleucae; Brachycaudus helichrysi; Brachycolus spp.; Brevicoryne brassicae; Cacopsyllas spp., for example, Cacopsylla pyricola; Calligypona marginata; Capulinia spp.; Carneocephala fulgida; sugarcane woolly aphid (Ceratovacunalanigera); Cercopidae; Ceroplastes spp.; strawberry aphid (Chaetosiphon fragaefolii); sugarcane yellow snow shield scale (Chionaspis tegalensis); tea leaf wasp (Chlorita onukii); Taiwan giant locust (Chondracris rosea); walnut black-spotted aphid (Chromaphis juglandicola); brown round scale (Chrysomphalus aonidum); black brown round scale (Chrysomphalus ficus); corn leafhopper (Cicadulina mbila); Coccomytilus halli; soft scale (Coccus spp.), such as brown soft wax scale (Coccus hesperidum), long oval soft scale (Coccus longulus), Coccus pseudomagnoliarum, Coccus viridis; Cryptomyzus ribis; Cryptonossa spp.; Ctenarytaina spp.; Dalbulus spp.; Dialeurodes chittendeni; Dialeurodes citri; Diaphorina 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 castevensi; Eriosoma spp., for example, Eriosoma americana americanum), Eriosoma lanigerum (apple aphid), Eriosoma pyricola (pear root aphid); Erythroneura spp.; Eucalyptolyma spp.; Euphylluras spp.; Euscelis bilobatus; Ferrisia spp.; Fiorinia spp.; Furcaspis oceanica; Geococcus coffeae; Glycaspis spp.; Heteropsylla cubana; Heteropsylla spinulosa; Homalodisca coagulata; Hyalopterus arundinis (peach aphid); Hyalopterus spp. pruni); Icerya spp., for example, 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; Lycormadelicatula; Macrosiphum spp., for example, Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae; Macrosteles facifrons; Mahanarva spp.; Melanaphis sacchari; Metcalfiella spp.; Metcalfapruinosa; Metopolophium dirhodum; Monellia costalis; Monelliopsis pecanis; Myzus spp., for example, Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzusornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri; Neomaskellia spp., Nephotettix spp., for example, Nephotettix cincticeps, Nephotettix nigropictus, Nettigonicllaspectra; Nilaparvata lugens; Oncometopia spp.; Ortheziapraelonga; Oxya chinensis); Pachypsylla spp.; Parabemisia myricae; Paratrioza spp., such as the potato psyllid (Paratrioza cockerelli); Parlatoria spp.; Pemphigus spp.), for example, Pemphigus bursarius, Pemphigus populivenae; Peregrinus maidis; Perkinsiella spp.; Phenacoccus spp., for example, Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli; Phylloxera spp., for example, Phylloxeradevastatrix, Phylloxeranotabilis; Pinnaspisaspidistrae; Planococcus spp., for example, Planococcus mealybugs citri); Prosopidopsylla flava; Protopulvinaria 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 spp. pyri); Pteromalus spp.; Pulvinaria spp.; Pyrilla spp.; Quadraspidiotus spp., such as Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, and Quadraspidiotus perniciosus; Quesada gigas; Rastrococcus spp.; Rhopalosiphum spp.), for example, Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale; Saissetia spp., for example, Saissetia coffieae, Saissetia miranda, Saissetia eglecta, Saissetia oleae; grape leafhopper (Scaphoideus titanus); wheat aphid (Schizaphis graminum); thorny shield scale (Selenaspidusarticulatus); yellow false hair aphid (Sipha flava); wheat long-spiked aphid (Sitobion avenae); long-lipped planthopper (Sogata planthopper) spp.); white-backed planthopper (Sogatellafurcifera); Sogatodes spp.; Stictocephalafestina; tree whitefly (Siphoninus phillyreae); Tenalaphara malayensis; Tetragonocephela spp.; pecan aphid (Tinocallis caryaefoliae); Tomaspis spp.; citrus aphid (Toxoptera spp.), for example, Toxoptera aurantii and Toxoptera citricidus; greenhouse whitefly (Trialeurodes vaporariorum); Trioza spp., for example, Triozadiospyri; Typhlocyba spp.); Unaspis spp.; Viteus vitifolii; Zygina spp.;

[0447] Pests from the order Heteroptera, for example, Aelia spp.; Anasatristis; Antestiopsis spp.; Boisea spp.; Blissus spp.; Calocoris spp.; Campylomma livida; Cavelerius spp.; Cimex spp., for example, Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus; Collaria spp.; Creontiades spp. dilutus; Dasynus piperis; Dichelops furcatus, Diconocorishewetti; Dysdercus spp.; Euschistus spp., for example, Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius; Eurydema spp.; Eurygaster spp.; Halyomorpha halys; Heliopeltis spp.; Horcias nobilellus; Leptocorisa spp.; Leptocorisa varicornis; Leptoglossus occidentalis; Leptoglossus phyllopus; Lygocoris spp., for example, Lygocoris pabulinus; Lygus spp., for example, Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus; Megacopta cribraria; Miridae; Monalonion atratum; Nezaras spp.), such as Nezara viridula; Nysius spp.; Oebalus spp.; Pentomidae; Piesma quadrata; Piezodorus spp., such as Piezodorus guildinii; Psallus spp.; Pseudacysta persea; Rhodnius spp.; Sahlbergella singularis; Scaptocoris castanea; Scotinophora spp., Stephanitis nashi; Tibraca spp.; Triatoma spp.;

[0448] Pests 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 acookei, Hoplocampa testudinea; Lasius spp.; Linepithema (Iridiomyrmex) humile; Monomorium spp. 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; Wasmannia auropunctata; Xeris spp.;

[0449] Pests from the order Isopoda, such as Armadillidium vulgare, Oniscus asellus, and Porcellio scaber;

[0450] Pests from the order of the 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 and Reticulitermes hesperus;

[0451] Pests from the order of the Lepidoptera, for example, Achroia grisella; Acronicta major; Adoxophyes spp., for example, Adoxophyesorana; Aedialeucomelas, Agrotis spp., for example, Agrotissegetum, Agrotis ipsilon; Alabama spp., for example, Alabama argillacea; Amyelois transitella; Anarsia spp.; Anticarsia spp., for example, Anticarsia gemmatalis; Argyroploce spp.; Autographa spp.); Cabbage armyworm (Barathrabrassicae); Apple marrow moth (Blastodacna atra); Grain butterfly (Borbo cinnara); Cotton miner (Bucculatrix thurberiella); Pine looper (Bupalus piniarius); Brown borer (Busseola spp.); Cacoecia spp.; Tea moth (Caloptilia theivora); Tobacco moth (Capua reticulana); Codling moth (Carpocapsa pomonella); Peach fruit moth (Carposina niponensis); Winter moth (Cheimatobia brumata); Grass borer (Chilo spp.), such as Chiloplejadellus and Chilosuppressalis; Apple dance moth (Choreutis pariana); Colored moth (Choristoneura) spp.); Chrysodeixis chalcites; Clysia ambiguella; Cnaphalocerus spp.; Cnaphalocrocis medinalis; Cnephasia spp.; Conopomorpha spp.; Conotrachelus spp.); Copitarsia spp.; Cydia spp., for example, Cydianigricana, Cydia pomonella; Dalaca noctuides; Diaphania spp.; Diparopsis spp.; Diatraea saccharalis; Dioryctria spp., for example, Dioryctria zimmermani; Earias spp., Ecdytolophaaurantium; Elasmopalpus lignosellus; Eldanas accharina; Ephestia spp., for example, Ephestia spp. elutella), Mediterranean mealybug (Ephestia kuehniella); Epinotia spp.; Epiphyas postvittana; Erannis spp.; Erschoviella musculana (Asian walnut moth); Etiella spp.; Eudocima spp.; Eulia spp.; Eupocilia ambiguella; Euproctis spp., such as Euproctis chrysorrhoea; Euxoa spp.; Feltia spp.; Galleria mellonella; Gracillaria spp.), Grapholitha spp., for example, Grapholita molesta (pear borer) and Grapholita prunivora (apricot borer); Hedyleptas spp.; Helicoverpa spp., for example, Helicoverpa armigera (cotton bollworm) and Helicoverpa zea (American cotton bollworm); Heliothis spp., for example, Heliothis virescens (tobacco budworm); Hofmannophila pseudospretella (brown weaver), Homoeosoma spp.); Homona spp.; Hyponomeuta padella (apple nest moth); Kakivoria flavofasciata (persimmon calyx beetle); Lampides spp.; Laphygma spp.; Laspeyresia molesta (Laspeyresia molesta); Leucinodes orbonalis (eggplant borer); Leucoptera spp., for example, Leucoptera coffeella (coffee leafminer); Lithocolletis spp., for example, Lithocolletis blancardella (apple leafminer); Lithophane antennata (green fruit armyworm); Lobesia spp., for example, Lobesia botrana (grape leafminer); Loxagrotis albicosta (bean rootworm); Lymantria spp. spp., such as Lymantria dispar; Lyonetia spp., such as Lyonetia clerkella; Malacosoma neustria; Maruca testulalis; Mamestra brassicae; Melanitis leda; Mocis spp.; Monopsiobviella; Mythimnaseparata; Nemapogon cloacellus; Nymphula spp.; Oiketicus spp.; Omphisa spp.; Operophtera spp.; Orias spp.; Orthaga spp.); Ostrinia spp., for example, Ostrinianubilalis; Panolis flammea; Parnara spp.; Pectinophora spp., for example, Pectinophora gossypiella; Perileucoptera spp.; Phthorimaea spp.), for example, the potato tuber moth (Phthorimaea operculella); the citrus leafminer (Phyllocnistis citrella); the small leafminer (Phyllonorycter spp.), for example, the spotted leafminer (Phyllonorycter blancardella), the hawthorn leafminer (Phyllonorycter crataegella); the cabbage butterfly (Pieris spp.), for example, the cabbage butterfly (Pieris rapae); the Dutch pink moth (Platynota stultana); the Indian meal moth (Plodia interpunctella); the goldworm (Plusia spp.); the diamondback moth (Plutella xylostella) (=Plutella maculipennis); the Podesia spp., for example, the Podesia syringae; the Prays spp. spp.); Prodenia spp.; Protoparce spp.; Pseudaletia spp., for example, Pseudaletia unipuncta; Pseudoplusia includens; Pyraustanubilalis; Rachiplusia nu; Schoenobius spp., for example, Schoenobius bipunctifer; Scirpophaga spp., for example, Scirpophaga innotata; Scotia segetum; Sesamia spp., for example, Sesamia inferens; Sparganothis spp. spp.); Spodoptera spp., such as Spodopteraeradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica; Stathmopoda spp.; Stenoma spp.; Stomopteryx subsecivella; Synanthedon spp.); Andean potato tuber moth (Tecia solanivora); Thaumetopoeas spp.; Thermesia gemmatalis; Tinea cloacella; Tineapellionella; Tineolabisselliella; Tortrix spp.; Trichophaga tapetzella; Trichoplusia spp., such as Trichoplusia ni; Tryporyza incertulas; Tuta absoluta; Virachola spp.;

[0452] Pests from the order Orthoptera or Saltatoria, for example, house crickets (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; and Desert locust (Schistocerca gregaria).

[0453] Pests from the order of the Phthiraptera, for example, Damalinia spp.; Haematopinus spp.; Linognathus spp.; Pediculus spp.; Phylloxeravastatrix; Phthirus pubis; Trichodectes spp.;

[0454] Pests from the order Psocoptera, for example, Lepinotus spp.; Liposcelis spp.;

[0455] Pests from the order Siphonaptera, for example, Ceratophyllus spp.; Ctenocephalides spp., for example, Ctenocephalides canis, Ctenocephalides felis; Pulex irritans; Tunga penetrans; Xenopsylla cheopis;

[0456] Pests 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, Frankliniella vaccinii, Frankliniella williamsi; Haplothrips spp.; Heliothrips spp.); Greenhouse Thrips (Hercinothrips femoralis); Kakothrips spp.; Grape Thrips (Rhipiphorothrips cruentatus); Scirtothrips spp.; Cardamom Thrips (Taeniothrips cardamomi); Thrips spp., such as Thrips palmi and Thrips tabaci;

[0457] Pests from the order Zygentoma (= Thysanura), for example Ctenolepisma spp.; Lepisma saccharina; Lepismodes inquilinus; Thermobia domestica;

[0458] Pests from the class Symphyla, for example Scutigerella spp., for example Scutigerella immaculata;

[0459] Pests from the phylum Mollusca, for example, the class Bivalvia, for example, Dreissena spp.;

[0460] and pests from the class Gastropoda, for example Arion spp., such as Arion ater rufus; Biomphalaria spp.; Bulinus spp.; Deroceras spp., such as Deroceras laeve; Galba spp.; Lymnaea spp.; Oncomelania spp.; Pomacea spp.; Succinea spp.;

[0461] Plant pests from the phylum Nematoda, i.e. phytoparasitic nematodes, in particular Aglenchus spp., for example Aglenchus agricola; Anguinas spp., for example Anguina tritici; Aphelenchoides spp., for example Aphelenchoides arachidis, Aphelenchoides fragariae; Belonolaimus spp., for example Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni; Bursaphelenchus spp., for example 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, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax); Criconemoides spp., for example, Criconemoides ferniae, Criconemoides sonoense, Criconemoides ornatum; Ditylenchus spp., for example, Ditylenchus dipsaci; Dolichodorus spp.; Globodera spp.), for example, Globodera pallida and Globodera rostochiensis; Helicotylenchus spp., for example, Helicotylenchus dihystera; Hemicriconemoides spp.; Hemicycliophora spp.; Heterodera spp., for example, Heterodera avenae, Heteroderaglycines, and Heterodera schachtii; Hirschmaniella spp.; Hoplolaimus spp.; Longidorus spp., for example, Longidorus africanus. africanus; Meloidogyne spp., for example, Meloidogyne 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.), such as Pratylenchus penetrans; Pseudohalenchus spp.; Psilenchus spp.; Punctodera spp.; Quinisulcius spp.; Radopholus spp.), for example, Radopholus citrophilus and Radopholus similis; Rotylenchulus spp.; Rotylenchus spp.; Scutellonema spp.; Subanguina spp.; Trichodorus spp., for example, Trichodorus obtusus and Trichodorus primitivus; Tylenchorhynchus spp., for example, Tylenchorhynchus annulatus; Tylenchulus spp., for example, Tylenchulus semipenetrans; Xiphinema spp. spp.), such as the standard Xiphinema index.

[0462] At certain concentrations or application rates, the compounds of formula (I) can optionally also be used as herbicides, safeners, growth regulators or agents that improve plant performance, as microbicides or gametocides, for example as fungicides, antifungals, bactericides, viricides (including agents against viroids) or as agents against MLOs (mycoplasma-like) and RLOs (rickettsia-like). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.

[0463] preparation

[0464] The present invention further relates to formulations, compositions and use forms comprising at least one compound of formula (I) as defined anywhere above. Such formulations and compositions are particularly prepared as insecticides, such as soaks, drip irrigation solutions and sprays, comprising at least one compound of formula (I). Such formulations may further comprise at least one other compound selected from among adjuvants, excipients, solvents and / or other pharmaceutically active agents. In some cases, the formulations or use forms comprise further insecticides and / or adjuvants to improve the action, such as penetrants, for example vegetable oils (e.g. rapeseed oil, sunflower oil), mineral oils (e.g. paraffin oil), alkyl esters of vegetable fatty acids (e.g. rapeseed oil methyl ester or soybean oil methyl ester) or alkanol alkoxylates; and / or spreaders, for example alkylsiloxanes and / or salts, for example organic or inorganic ammonium salts or phosphonium salts, for example ammonium sulfate or diammonium hydrogen phosphate; and / or retention promoters, for example dioctyl sulfosuccinate or hydroxypropyl guar polymers; and / or humectants, for example glycerol; and / or fertilizers, for example ammonium-, potassium- or phosphorus-containing fertilizers.

[0465] Conventional formulations are, for example, water-soluble liquids (SL), emulsifiable concentrates (EC), emulsions in water (EW), suspensions (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); these formulations and other possible formulation types are described, for example, in Crop Life International and in the following documents: Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers-173 (prepared by the Joint FAO / WHO Meeting on Pesticide Specifications, 2004, ISBN: 9251048576). In addition to one or more compounds of formula (I), the formulations optionally contain other agrochemically active compounds.

[0466] These are preferably formulations or use forms comprising auxiliary agents, such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, frost protectants, biocides, thickeners and / or other auxiliary agents (e.g. adjuvants). An adjuvant in the context of the present invention is a component that enhances the biological effect of a formulation without itself having any biological effect. Examples of adjuvants are agents that promote retention, spreading, adhesion to leaf surfaces, or penetration.

[0467] These preparations are prepared in a known manner, for example by mixing a compound of formula (I) with an auxiliary agent, such as, for example, an extender, a solvent and / or a solid carrier and / or other auxiliary agents, such as, for example, a surfactant. The preparation is prepared in a suitable device or before or during application.

[0468] The adjuvants used may be substances which are suitable for imparting specific properties (e.g. certain physical, technical and / or biological properties) to the formulations of the compounds of formula (I) or to the use forms prepared therefrom (e.g. ready-to-use insecticides such as spray liquids or seed dressing products).

[0469] Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the group of aromatic and nonaromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which, if appropriate, may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide), carbonates and nitriles.

[0470] If the extender used is water, it is also possible to adopt, for example, an organic solvent as auxiliary solvent. Basically, suitable liquid solvents are: aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons such as chlorobenzenes, vinyl chlorides or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffin, for example mineral oil fractions, mineral oils and vegetable oils, alcohols such as butanol or ethylene glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, highly 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 propionitrile.

[0471] In principle, all suitable solvents can be used. Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride or dichloromethane; aliphatic hydrocarbons, such as cyclohexane, paraffin, petroleum fractions, mineral oils and vegetable oils; alcohols, such as methanol, ethanol, isopropanol, butanol or ethylene glycol and their ethers and esters; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; highly polar solvents, such as dimethyl sulfoxide; carbonates, such as propylene carbonate, butylene carbonate, diethyl carbonate or dibutyl carbonate; nitriles, such as acetonitrile or propionitrile; and also water.

[0472] In principle, all suitable carriers can be used. Useful carriers include, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, as well as ground synthetic materials such as finely divided silicon dioxide, aluminum oxide, and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Carriers that can be used for granules include, for example, crushed and classified natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic particles of inorganic and organic powders, as well as particles of organic materials such as sawdust, paper, coconut shells, corn cobs and tobacco stalks.

[0473] Liquefied gaseous extenders or solvents may also be used. Particularly suitable extenders or carriers are those which are gaseous at ambient temperature and atmospheric pressure, for example aerosol propellant gases such as halogenated hydrocarbons, and also butane, propane, nitrogen and carbon dioxide.

[0474] Examples of emulsifiers and / or foam-formers, dispersants or wetting agents having ionic or nonionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of ligninsulfonic acid, salts of phenolsulfonic acid or salts of naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, polycondensates of ethylene oxide with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinates, taurine derivatives (preferably alkyl taurates), isethionate derivatives, phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of compounds containing sulfates, sulfonates and phosphoric acid esters, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates, protein hydrolysates, ligninsulfite waste liquors and methylcellulose. The presence of a surfactant is advantageous if one of the compounds of formula (I) and / or one of the inert carriers is insoluble in water and when application is carried out in water.

[0475] In the preparations and the use forms derived therefrom, it is possible to use the following as further auxiliaries: colorants, such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue; and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes; and nutrients and trace nutrients, such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts.

[0476] Other components may be stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents that improve chemical and / or physical stability.Foaming agents or defoamers may also be present.

[0477] The following substances may also be present as additional adjuvants in the formulations and the use forms derived therefrom: adhesives such as carboxymethylcellulose, and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural phospholipids such as cephalin and lecithin, as well as synthetic phospholipids. Other possible adjuvants are mineral oils and vegetable oils.

[0478] Optionally, other auxiliary agents may also be present in the formulation and the use-forms obtained therefrom. Examples of such additives include spices, protective colloids, adhesives, tackifiers, thickeners, thixotropic agents, penetrants, retention promoters, stabilizers, chelating agents, complexing agents, wetting agents, spreading agents. Typically, the compound of formula (I) may be combined with any solid or liquid additive that is typically used for formulation purposes.

[0479] Useful retention promoters include all those substances which reduce the dynamic surface tension, such as dioctyl sulfosuccinate, or all those substances which increase the viscoelasticity, such as hydroxypropyl guar polymers.

[0480] In the context of the present invention, suitable penetrants are all substances which are usually used to improve the penetration of agrochemical active compounds into plants. In the context of the present invention, penetrants are defined by their ability to penetrate into the plant cuticle from the (usually aqueous) application liquid and / or from the spray coating and thus increase the mobility of the active compound in the cuticle. This property can be determined using the method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152). Examples include alcohol alkoxylates such as coconut fat 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 tallowamine ethoxylate (15); or ammonium salts and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.

[0481] The preparation preferably contains 0.00000001% to 98% by weight of the compound of formula (I), or particularly preferably 0.01% to 95% by weight of the compound of formula (I), more preferably 0.5% to 90% by weight of the compound of formula (I), based on the weight of the preparation.

[0482] In the use forms prepared from the formulations, in particular insecticides, the content of the compound of formula (I) can vary within a wide range. In the use forms, the concentration of the compound of formula (I) is generally from 0.00000001% to 95% by weight, preferably from 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.

[0483] mixture

[0484] The compounds of formula (I) can also be used in the form of mixtures with one or more suitable following substances: fungicides, bactericides, acaricides, molluscicides, nematocides, insecticides, microorganisms, beneficial species, herbicides, fertilizers, bird repellents, phytotoxins (phytotonics), sterilants (sterilants), safeners, chemical semiochemicals and / or plant growth regulators, thereby, for example, broadening the spectrum of action, prolonging the duration of action, increasing the rate of action, preventing repulsion or preventing the development of resistance. In addition, such active compound combinations can improve plant growth and / or increase tolerance to abiotic factors (e.g., high or low temperatures), tolerance to drought or to increased water content or soil salinity. It can also improve flowering and fruiting performance, optimize germination ability and root development, promote harvesting and increase yield, influence maturity, improve the quality and / or nutritional value of the harvested product, extend the shelf life of the harvested product and / or improve the processing properties of the harvested product.

[0485] In addition, the compounds of formula (I) can be present in the form of a mixture with other active compounds or semiochemicals such as 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 performance, such as, for example, the growth, yield and quality of the harvested material.

[0486] In a particular embodiment according to the invention, the compounds of formula (I) are present in the formulations or the use forms prepared from these formulations in the form of a mixture with other compounds, preferably those as described below.

[0487] If one of the compounds mentioned below can exist in different tautomeric forms, these are also included, even if not explicitly mentioned in each case. Furthermore, all of the mixing components mentioned can optionally form salts with suitable bases or acids if their functional groups are capable of forming salts with suitable bases or acids.

[0488] Insecticides / Acaricides / Nematicides

[0489] The active compounds identified herein by their common names are known and described, for example, in the Pesticide Manual ("The Pesticide Manual", 16th edition, British Crop Protection Council 2012), or can be found 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.

[0490] (1) Acetylcholinesterase (AChE) inhibitors, preferably selected from the following carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, fenamiprid formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb;or an organophosphate selected from the following: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, cyanophos, demeton-S-methyl, diazinon, dichlorvos ) / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate pylO-(methoxyaminothiophosphoryl)salicylate), isoxathion, malathion, mecarbam, methidathion, mevinphos, naled, omethoate, oxydemeton-methyl, phenthoate, phorate, phosalone, phosmet, phoxim, methylpyrimidine pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, tebupirimfos, temephos, tetrachlorvinphos, thiometon-methyl, triazophos, triclorfon, and vamidothion.

[0491] (2) GABA-gated chloride channel blockers, preferably selected from the following cyclopentadienyl organochlorines: chlordane and endosulfan; or selected from the following phenylpyrazoles (fiproles): ethiprole and fipronil.

[0492] (3) Sodium channel modulators, preferably selected from the group consisting of the following pyrethroids: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomer] isomer]), deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans isomer] isomer]), prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)isomer], tralomethrin, transfluthrin, or methoxychlor.

[0493] (4) Competitive modulators of nicotinergic acetylcholine receptors (nAChRs), preferably selected from the following neonicotinoids: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine; or sulfoximines selected from sulfoxaflor; or butenolids selected from flupyradifurone; or mesoionics selected from triflumezopyrim.

[0494] (5) Nicotinergic acetylcholine receptor (nAChR) allosteric modulators, preferably spinosyns selected from the group consisting of spinetoram and spinosad.

[0495] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators, preferably selected from the following avermectins / milbemycins: abamectin, emamectin benzoate, lepimectin and milbemectin.

[0496] (7) Juvenile hormone mimetics, preferably selected from the following juvenile hormone analogs: hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.

[0497] (8) Various non-specific (multi-site) inhibitors, preferably alkyl halides selected from the group consisting of methyl bromide and other alkyl halides; or chloropicrine or sulphuryl fluoride or borax or tartar emetic; or methyl isocyanate generators selected from the group consisting of diazomet and metam.

[0498] (9) A chordotonal organ TRPV channel modulator selected from pymetrozine and pyrifluquinazone.

[0499] (10) A mite growth inhibitor selected from the group consisting of clofentezine, hexythiazox, diflovidazin and etoxazole.

[0500] (11) An insect gut membrane microbial disruptor selected from the group consisting of: Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and a Bt plant protein selected from the group consisting of: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, and Cry34Ab1 / 35Ab1.

[0501] (12) Mitochondrial ATP synthase inhibitors, preferably ATP disruptors selected from diafenthiuron; or organotin compounds selected from the following: azocyclotin, cyhexatin and fenbutatinoxide, or propargite, or tetradifon.

[0502] (13) An oxidative phosphorylation uncoupler that acts via a staggered proton gradient, selected from the group consisting of chlorfenapyr, dinitrocresol (DNOC) and sulfluramid.

[0503] (14) Nicotinic acetylcholine receptor channel blockers selected from the group consisting of bensultap, cartap hydrochloride, thiocylam and thiosultap-sodium.

[0504] (15) Type O chitin biosynthesis inhibitors selected from the group consisting of bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[0505] (16) Type 1 chitin biosynthesis inhibitor selected from: buprofezin.

[0506] (17) Molting disruptors (especially for Diptera, i.e., two-winged insects), selected from: cyromazine.

[0507] (18) An ecdysone receptor agonist selected from the group consisting of chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0508] (19) Octopamine receptor agonist selected from amitraz.

[0509] (20) A mitochondrial complex III electron transport inhibitor selected from the group consisting of hydramethylnone, acequinocyl and fluacrypyrim.

[0510] (21) Mitochondrial complex I electron transport inhibitors, preferably selected from the following METI acaricides: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).

[0511] (22) A voltage-dependent sodium channel blocker selected from the group consisting of indoxacarb and metaflumizone.

[0512] (23) Acetyl Coenzyme A (CoA) carboxylase inhibitors, preferably selected from the group consisting of tetronic acid and tetramic acid derivatives: spirodiclofen, spiromesifen and spirotetramat.

[0513] (24) Mitochondrial complex IV electron transport inhibitors, preferably selected from the following phosphine compounds: aluminum phosphide, phosphine; or selected from the following cyanide compounds: calcium cyanide, potassium cyanide and sodium cyanide.

[0514] (25) Mitochondrial complex II electron transport inhibitors, preferably beta-keto nitrilederivatives selected from the group consisting of cyenopyrafen and cyflumetofen; and carboxanilides selected from the group consisting of pyflubumide.

[0515] (28) A ryanodine receptor modulator, preferably a diamide selected from the group consisting of chlorantraniliprole, cyantraniliprole and flubendiamide.

[0516] (29) String organ modulator (with undefined target site), selected from: flonicamid.

[0517] (30) Other active compounds selected from the group consisting of: Acynonapyr, Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Benzpyrimoxan, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite e), Cyclaniliprole, Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, Dimpropyridaz, epsilon-Metofluthrin, epsilon-Momfluthrin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxyst robin), Flufiprole, Fluhexafon, Fluopyram, Flupyrimin, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Isocycloseram, kappa-Bifenthrin, kappa-Tefluthrin, Lot ilaner, Meperfluthrin, Oxazosulfyl, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Spiropyridion, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Tioxazafen,Thiofluoximate iodomethane; another preparation based on Bacillus firmus (I-1582, BioNeem, Votivo), and 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 WO2006 / 043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidinyl]-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 EP 2647626) (CAS-1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004 / 099160) (CAS792914-58-0), PF1364 (known from JP2010 / 018586) (CAS1204776-60-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylene]-1,1,1-trifluoropropan-2-one (known from WO20 13 / 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 (from WO 2013 / 050317) A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propionamide, (+)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propionamide and (-)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propionamide (from WO 2013 / 162715 A2, WO 2013 / 162716 A2, US2014 / 0213448 A1) (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 CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thiomethyl]phenyl]-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO 2012 / 034403 A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from WO 2011 / 085575 A1) (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 CN 101337940 A) (CAS 1108184-52-6); (2E)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (known from CN 101715774A) (CAS 1232543-85-9); 3-(2,2-dichlorovinyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylate (known from CN 103524422 A) (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 CN 102391261 A) (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 (from US 2014 / 0275503 A1) (CAS1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS1253850-56-4), (8-trans)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS933798-27-7), (8-cis)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propionamide (from WO 2015 / 058021 A1,WO 2015 / 058028 A1) (CAS 1477919-27-9) and N-[4-(aminothiomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxane-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]pyrimidine (known from WO 2013 / 115391A1) (CAS1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (known from WO2014 / 187846 A1) (CAS1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl carbonate (known from WO 2010 / 066780 A1, WO2011151146 A1) (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 WO 2011 / 067272 and WO 2013 / 050302) (CAS 1309959-62-3).

[0518] fungicides

[0519] The active ingredients designated herein by their common names are known and described, for example, in The Pesticide Manual (16th edition, British Crop Protection Council) or can be found on the Internet (e.g.: http: / / www.alanwood.net / pesticides) Search on.

[0520] If the functional groups of the fungicidal mixture components are capable of forming salts with suitable bases or acids, all of the fungicidal mixture components mentioned in classes (1) to (15) may optionally form salts with suitable bases or acids. Where applicable, all of the mixture components mentioned in classes (1) to (15) may include tautomeric forms.

[0521] 1) Ergosterol biosynthesis inhibitors, such as (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 sulfate), (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (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) trichlorfonazole 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] (pyridine -3-yl)methanol, (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-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate Cyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptane-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-trimethylheptane-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-trimethylheptane-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-trimethylheptane-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-trimethylheptane-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-trimethylheptane-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-trimethylheptane-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-trimethylheptane-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptane-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) Mefentrifluconazol ole), (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-methylimidocarboxamide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidocarboxamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidocarboxamide, (1. 066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidocarboxamide, (1.067) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidocarboxamide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidocarboxamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N -ethyl-N-methylimidocarboxamide, (1.070) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidocarboxamide, (1.071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidocarboxamide, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidocarboxamide, (1.073) N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidocarboxamide, (1.074) N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidocarboxamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidocarboxamide, (1.076) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidocarboxamide, (1.077) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidocarboxamide N-ethyl-N-methylimidocarboxamide, (1.078) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidocarboxamide, (1.079) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidocarboxamide, (1.080) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidocarboxamide, (1.081) Ipfentrifluconazole.

[0522] 2) Inhibitors of respiratory chain complex I or II, for example (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) isofetamid, (2.010) pyrimidine Isopyrazam (trans epimers 1R, 4S, 9S), (2.011) Isopyrazam (trans epimers 1S, 4R, 9R), (2.012) Isopyrazam (trans epimers 1RS, 4SR, 9SR), (2.013) Isopyrazam (mixture of cis epimers 1RS, 4SR, 9RS and trans epimers 1RS, 4SR, 9SR), (2.014) Isopyrazam (cis epimers 1R, 4S, 9R), (2.015) Isopyrazam (cis epimers 1S, 4R, 9S), (2.016) Isopyrazam (cis epimers racemic isomers 1RS, 4SR, 9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.028) 3-(difluoromethyl)-1-methyl-N-[(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-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-( (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-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.039) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.040) 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) isoflucypram, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-naphthylene-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylene)-1, 2,3,4-tetrahydro-1,4-naphthylene-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxyprop-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]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-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-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide (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-carboxamide, (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 Amide, (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) pyrapropoyne.

[0523] 3) Respiratory chain complex III inhibitors, such as (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone ne), (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) pyrametostrobin obin), (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-dimethylpentyl]oxy}phenyl}-2-(methoxyimino)-N,3-dimethylpent-3-enamide methylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (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-dioxacyclononan-7-yl 2-methylpropanoate, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-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) metyltetraprole, (3.031) florylpicoxamid.

[0524] 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.

[0525] 5) Compounds capable of multi-site action, such as (5.001) Bordeaux mixture, (5.002) Captafol, (5.003) Captan, (5.004) Chlorothalonil, (5.005) Copper hydroxide, (5.006) Copper naphthenate, naphthenate), (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper (2+) sulfate, (5.010) dicyanoanthraquinone (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 preparations including calcium polysulfide, (5.020) thiram, (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.

[0526] 6) Compounds capable of inducing host defense, such as (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, and (6.004) tiadinil.

[0527] 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.

[0528] 8) ATP production inhibitors, for example (8.001) silthiofam.

[0529] 9) Cell wall synthesis inhibitors, for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (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.

[0530] 10) Lipid and membrane synthesis inhibitors, for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

[0531] 11) Melanin biosynthesis inhibitors, for example (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl {3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

[0532] 12) Nucleic acid synthesis inhibitors, for example (12.001) benalaxyl, (12.002) kiralaxyl, (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0533] 13) Signal transduction inhibitors, for example, (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, and (13.006) vinclozolin.

[0534] 14) Compounds that can act as uncouplers, for example (14.001) fluazinam and (14.002) meptyldinocap.

[0535] 15) Other compounds, such as (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid, (15.0 09) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Flutianil, (15.012) Fosetyl-aluminum, (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) oxathiapiprolin, (15.023) oxyfenthiin, (15.024) pentachlorophenol and its salts, (15.025) phosphorous acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pyrophosphate riofenone (chlazafenone), (15.028) isobutylethoxyquinoline (tebufloquin), (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}piperidin-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) dipymetitrone, (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(difluoromethyl)-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) Ipflufenoquin, (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) quinofumelin, (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-thiadiol Oxazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazide, (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-benzoxepin 、(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-phenylacrylate, (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.

[0536] Biopesticides as mixing components

[0537] The compounds of formula (I) may be combined with biopesticides.

[0538] Biopesticides include, in particular, bacteria, fungi, yeasts, plant extracts and products formed by microorganisms, including proteins and secondary metabolites.

[0539] Biopesticides include bacteria, such as spore-forming bacteria, root-colonizing bacteria, and bacteria that act as bioinsecticides, fungicides, or nematicides.

[0540] Examples of such bacteria that are or can be used as biopesticides are:

[0541] Bacillus amyloliquefaciens, strain FZB42 (DSM 231179); or Bacillus cereus, in particular Bacillus cereus strain CNCM 1-1562; or Bacillus firmus, strain I-1582 (accession number CNCM 1-1582); 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 Bacillus thuringiensis, in particular Bacillus thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (accession number ATCC 1276), or Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or Bacillus thuringiensis subsp. kurstaki strain HD-1, or Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428); Pasteuria penetrans; Pasteuria spp. (Rotylenchulus reniformis nematode))-PR3 (accession number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (=QRD31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (accession number NRRL30232).

[0542] Examples of fungi and yeasts that are or can be used as biopesticides are:

[0543] 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 (DSM 3884 / ATCC 90448); Metschnikowia fructicola, in particular strain NRRL Y-30752; Paecilomyces fumosoroseus (now known as Isaria fumosorosea), in particular strain IFPC 200613 or strain Apopka 97 (accession number ATCC 20874); Paecilomyces lilacinus, in particular Paecilomyces lilacinus strain 251 (AGAL 89 / 030550); Talaromyces flavus, in particular strain V117b; Trichoderma atroviride, in particular strain SC1 (accession number CBS122089); Trichoderma harzianum, in particular T. harzianum rifai T39 (accession number CNCM 1-952).

[0544] Examples of viruses that are or can be used as biopesticides are: Adoxophyes orana (summer fruit tortrix) granulovirus (GV), Cydia pomonella (codling moth) granulovirus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV, Spodoptera littoralis (African cotton leafworm) NPV.

[0545] Also included are bacteria and fungi that are added to plants or plant parts or plant organs as "inoculants" and that promote plant growth and plant health through their specific properties. 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 Gigasporamonosporum, Glomus spp.; Laccaria spp.; Lactobacillus buchneri; Paraglomus spp.; Pisolithus tinctorus; Pseudomonas spp.; Rhizobium spp., in particular Rhizobium trifolii; Rhizopogon spp.; Scleroderma spp.; Suillus spp.; Streptomyces spp.

[0546] Examples of plant extracts and products formed by microorganisms (including proteins and secondary metabolites) that are or can be used as biopesticides are: Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, "Requiem TM "Insecticides," rotenone, ryania / ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extracts (particularly rapeseed or mustard meal).

[0547] As a safener for mixed components

[0548] The compounds of formula (I) may be combined with safeners such as, for example, benoxacor, cloquintocet(-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole(-ethyl), fenclorim, flurazole, fluxofenim, furilazole, dichlormethane, fenthiophene, fenthiophene-1-oxazolidinone ... 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).

[0549] Plants and plant parts

[0550] All plants and plant parts can be processed according to the present invention.In this article, plant should be understood to mean all plants and plant parts, such as needed and unwanted wild plants or crop plants (comprising naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybean, potato, beet, sugarcane, tomato, pepper, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, kidney bean, Brassica oleracea (such as cabbage) and other vegetable species, cotton, tobacco, rape and fruit plants (fruit is apple, pear, citrus fruit and grapevine (grapevine)).Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnology and genetic engineering methods or the combination of these methods, including genetically modified plants and including plant varieties that can or are not protected by variety property rights.Plant should be understood to mean all developmental stages, such as seed, seedling, young (immature) plant until mature plant. Plant parts are understood to mean all parts and organs of plants above and below ground, such as buds, leaves, flowers and roots, examples being leaves, needles, petioles, stems, flowers, fruiting bodies, fruits and seeds, as well as tubers, roots and rhizomes. Plant parts also include harvested plants or harvested plant parts and vegetative and sexual propagation material, such as seedlings, tubers, rhizomes, cuttings and seeds.

[0551] The treatment of plants and plant parts with the compounds of formula (I) according to the invention is carried out directly or by allowing the compounds to act on their surroundings, environment or storage space by customary treatment methods, such as immersion, spraying, evaporation, fogging, scattering, coating, injection and, in the case of propagation materials, in particular seeds, also by applying one or more coatings.

[0552] As mentioned above, all plants and their parts can be treated according to the present invention. In a preferred embodiment, wild plant varieties and plant cultivars or those plants and their parts obtained by conventional biological breeding methods such as hybridization or protoplast fusion are treated. In another preferred embodiment, transgenic plants and plant cultivars (genetically modified organisms) and their parts obtained by genetic engineering methods, if suitable in combination with conventional methods, are treated. The terms "parts" or "parts of plants" or "plant parts" have been explained above. The present invention is particularly preferably used to treat plants of various commercially available conventional cultivars or those plants in use. Plant cultivars should be understood to mean plants with new characteristics ("traits") and obtained by conventional breeding, mutagenesis or recombinant DNA technology. They can be cultivars, variants, biotypes or genotypes.

[0553] Transgenic plants, seed treatments, and integration events

[0554] Transgenic plants or plant cultivars (those obtained by genetic engineering) that are preferably treated according to the invention include all plants that have received genetic material by genetic modification, which imparts particularly advantageous, useful properties ("traits") to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity levels, enhanced flowering performance, easier harvesting, accelerated maturation, higher harvest yield, higher quality and / or higher nutritional value of the harvested product, better shelf life and / or processing properties of the harvested product. Other and particularly emphasized examples of such properties are: enhanced resistance of plants to animal pests and microbial pests, such as insects, arachnids, nematodes, mites, slugs and snails, due to, for example, toxins formed in the plants, in particular those formed in the plants by genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and combinations thereof), and, moreover, enhanced resistance of plants to phytopathogenic fungi, bacteria and / or viruses, due to, for example, systemic acquired resistance (SAR), systemins, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, and increased tolerance of plants to certain herbicidally active compounds, such as imidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example the "PAT" gene). The genes contemplated for conferring the desired traits can also be present in combination with one another in transgenic plants. Examples of transgenic plants that may be mentioned are important crop plants such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other vegetable species, cotton, tobacco, rapeseed, and fruit plants (fruits such as apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed. Traits that are particularly emphasized are increased resistance of the plants to insects, arachnids, nematodes, slugs and snails.

[0555] Crop protection - types of treatments

[0556] The treatment of plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their surroundings, habitat or storage space using customary treatment methods, such as impregnation, spraying, atomization, irrigation, evaporation, dusting, misting, broadcasting, foaming, coating, spreading-on, injection, watering (drenching), drip irrigation, and in the case of propagation materials, in particular seeds, as powders for dry seed treatment, solutions for liquid seed treatment, water-soluble powders for slurry treatment, by coating with a shell, by coating with one or more coatings, etc. Furthermore, it is also possible to apply the compounds of formula (I) by the ultra-low volume method or to inject the application forms or the compounds of formula (I) themselves into the soil.

[0557] A preferred direct treatment of plants is foliar application, ie application of the compounds of formula (I) to the leaves, the frequency of treatment and the application rate being adjusted to the level of infestation by the pest in question.

[0558] For systemic active compounds, the compound of formula (I) also enters plant through the root system.Then by acting on the habitat of plant with the compound of formula (I) to process plant.This can be completed, for example, by being soaked in or by being mixed into soil or nutrient solution, i.e., impregnating plant locale (such as soil or hydroponic system) with the liquid form of the compound of formula (I), or by soil application, completed, i.e., being introduced into plant locale with solid form (such as in the form of granules) according to the compound of formula (I) of the present invention, or by drip irrigation application (also commonly referred to as "chemical irrigation"), completed, i.e., by ground drip pipe or underground drip pipe at a designated location near plant over a certain period of time, the compound of formula (I) of the present invention and different amounts of water are applied together with the liquid.For rice crops, this can also be completed by being metered into paddy field with the compound of formula (I) in solid application form (such as in the form of granules).

[0559] Seed treatment

[0560] The process of treating the seeds of plants to prevent and control animal pests has long been known and is a subject of continuous improvement. However, the treatment of seeds has caused a series of problems that can never be solved in a satisfactory manner. Therefore, it is desirable to develop a method for protecting seeds and budding plants, which method does not require or at least significantly reduces the use of additional insecticides during storage, after sowing, or after plant emergence. In addition, it is desirable to optimize the amount of the active compound used in this way: provide optimal protection for seeds and budding plants from infection by animal pests, while the active compound used does not damage the plant itself. In particular, the method for seed treatment should also take into account the inherent insecticide properties or nematode properties of transgenic plants that resist or tolerate insects, so as to achieve optimal protection for seeds and budding plants using a minimum amount of insecticides.

[0561] The present invention therefore also relates in particular to a method for protecting seeds and germinating plants from infestation by pests by treating the seeds with one of the compounds of formula (I). The method according to the invention for protecting seeds and germinating plants from infestation by pests also includes methods in which the seeds are treated simultaneously with the compound of formula (I) and the mixture components in a single operation or in a sequential manner. It also includes methods in which the seeds are treated with the compound of formula (I) and the mixture components at different times.

[0562] The invention likewise relates to the use of the compounds of the formula (I) for treating seed for protecting the seed and the resulting plant from infestation by animal pests.

[0563] In addition, the present invention relates to seeds treated with a compound of formula (I) according to the present invention to provide protection against infestation by animal pests. The present invention also relates to seeds treated simultaneously with a compound of formula (I) and a mixture of ingredients. The present invention also relates to seeds treated at different times with a compound of formula (I) and a mixture of ingredients. For seeds treated at different times with a compound of formula (I) and a mixture of ingredients, the substances may be present on the seeds in different layers. In this context, the layers comprising the compound of formula (I) and the mixture of ingredients may optionally be separated by intermediate layers. The present invention also relates to seeds to which the compound of formula (I) and the mixture of ingredients are applied as a component of a coating or as another layer or layers in addition to the coating.

[0564] Furthermore, the present invention relates to seeds which, after being treated with the compound of formula (I), are film-coated to protect the seeds from dust abrasion.

[0565] One of the advantages of using systemically acting compounds of formula (I) is that by treating the seeds, not only the seeds themselves are protected, but also the plants produced therefrom are protected from infestation by animal pests after emergence. In this way, it is possible to dispense with the immediate treatment of the crops at sowing or shortly thereafter.

[0566] Another advantage that must be taken into account is that the treatment of seed with compounds of formula (I) can enhance germination and emergence of the treated seeds.

[0567] It is likewise considered to be advantageous that the compounds of the formula (I) can also be used, in particular, in transgenic seeds.

[0568] Furthermore, compounds of formula (I) may be used in combination with signaling technology compositions or compounds to allow for better colonization by symbionts (such as, for example, rhizobia, mycorrhizae and / or endophytic bacteria or fungi) and / or to optimize nitrogen fixation.

[0569] The compound of formula (I) is suitable for protecting the seed of any plant variety used in agriculture, greenhouse, forestry or gardening.Especially, the seed is in the following form: the seed of cereal (for example wheat, barley, rye, millet and oat), corn, cotton, soybean, rice, potato, sunflower, coffee, tobacco, Canada rape (canola), rape, beet (for example sugar beet and fodder beet), peanut, vegetables (for example tomato, cucumber, kidney bean, cruciferous vegetables, onion and lettuce), fruit plant, lawn plant and ornamental plant.The processing of the seed of cereal (as wheat, barley, rye and oat), corn, soybean, cotton, Canada rape, rape, vegetables and rice is particularly important.

[0570] As mentioned above, the treatment of transgenic seeds with compounds of formula (I) is also particularly important. They are generally in the form of seeds of plants containing at least one heterologous gene that controls the expression of a polypeptide having, in particular, insecticidal and / or nematocidal properties. The heterologous gene in transgenic seeds can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly suitable for treating transgenic seeds containing at least one heterologous gene derived from Bacillus. It is particularly preferably a heterologous gene derived from Bacillus thuringiensis.

[0571] In the context of the present invention, the compound of formula (I) is applied to the seed. Preferably, the seed is treated in a state where the seed is sufficiently stable to avoid damage during treatment. Typically, the seed can be treated at any time point between harvesting and sowing. The seeds commonly used have been separated from the plant and the cob, shell, handle, epidermis, hair or pulp have been 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 and then dried, such as priming, after drying can also be used. For rice seeds, seeds that have been soaked in, for example, water to a certain stage of the rice embryo ("endosperm stage") can also be used to stimulate germination and make emergence more uniform.

[0572] When treating seed, care must generally be taken to select the amount of compound of formula (I) and / or other additives applied to the seed so that germination of the seed is not adversely affected or the resulting plant is not damaged. This must be ensured in particular for active compounds that may exhibit phytotoxic effects at certain application rates.

[0573] Typically, the compound of formula (I) is applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.

[0574] The compounds of formula (I) can be converted into customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seeds, and ULV formulations.

[0575] These formulations are prepared in a known manner by mixing the compounds of formula (I) with conventional additives, such as, for example, conventional extenders and also solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, binders, gibberellins and water.

[0576] Colorants that may be present in the seed dressing formulations that can be used according to the invention are all colorants customary for such purposes. Pigments that are sparingly soluble in water or dyes that are soluble in water can be used. Examples include the dyes known under the names Rhodamine B, CI Pigment Red 112, and CI Solvent Red 1.

[0577] Useful wetting agents that may be present in the seed dressing formulations which can be used according to the invention are all substances which promote wetting and are customarily used for the formulation of agrochemically active compounds. Preference is given to using alkyl naphthalenesulfonates, such as diisopropyl naphthalenesulfonate or diisobutyl naphthalenesulfonate.

[0578] Useful dispersants and / or emulsifiers that may be present in the seed dressing formulations that can be used according to the invention are all nonionic, anionic, and cationic dispersants commonly used for the formulation of active agrochemical ingredients. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants include, in particular, ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and their phosphated or sulfated derivatives. Suitable anionic dispersants are, in particular, ligninsulfonates, polyacrylates, and arylsulfonate / formaldehyde condensates.

[0579] Defoamers that may be present in the seed dressing formulations which can be used according to the invention are all foam-inhibiting substances which are customary for the formulation of active agrochemical ingredients. Preference is given to using silicone defoamers and magnesium stearate.

[0580] Preservatives that may be present in the seed dressing formulations which can be used according to the invention are all substances which can be employed for such purposes in agrochemical compositions. Examples include dichlorophen and benzyl alcohol hemiformal.

[0581] Secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays and also finely divided silica.

[0582] Binders that may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in seed dressing products. Polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and methylcellulose (tylose) may be mentioned as preferred.

[0583] The gibberellins that may be present in the seed dressing formulations which can be used according to the invention are preferably gibberellins A1, A3 (= gibberellic acid), A4 and A7; gibberellic acid is particularly preferably used. Gibberellins are known (cf. R. Wegler "Chemie der Pflanzenschutz-and Volume 2, Springer-Verlag, 1970, pp. 401-412).

[0584] The seed dressing formulations that can be used according to the invention can be used directly or after prior dilution with water to treat a wide variety of seed types. For example, the concentrates or formulations derived therefrom by dilution with water can be used to dress the seeds of cereals such as wheat, barley, rye, oats, and triticale, as well as corn, rice, rapeseed, peas, beans, cotton, sunflower, soybeans, and sugar beets, or a wide variety of vegetable seeds. The seed dressing formulations that can be used according to the invention, or diluted forms thereof, can also be used to dress the seeds of genetically modified plants.

[0585] For seed treatment using the seed dressing formulations that can be used according to the invention or the use forms prepared therefrom by adding water, all mixing units that are generally used for seed dressing are suitable. Specifically, the seed dressing process involves placing the seeds in a mixer, operating batchwise or continuously, adding the specific desired amount of the seed dressing formulation (either as such or after prior dilution with water), and mixing all substances until the formulation is evenly distributed over the seeds. If appropriate, this is followed by a drying operation.

[0586] The application rate of the seed dressing formulations that can be used according to the invention can vary within a relatively wide range. This depends on the specific content of the compound of formula (I) in the formulation and the seeds. The application rate of the compound of formula (I) is generally 0.001 to 50 g per kilogram of seed, preferably 0.01 to 15 g per kilogram of seed.

[0587] Animal Health

[0588] In the field of animal health, ie veterinary medicine, the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. Ectoparasites are generally and preferably arthropods, in particular insects or mites.

[0589] In the field of veterinary medicine, the compounds of formula (I) having a favorable toxicity in warm-blooded animals are suitable for controlling parasites that occur in animal breeding and animal husbandry of livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals (companion animals). They are active against all or specific developmental stages of parasites.

[0590] Agricultural livestock (farm animals) include, for example, mammals, such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, deer, and in particular cattle and pigs; or poultry, such as turkeys, ducks, geese, and in particular chickens; or fish or crustaceans, for example in aquaculture; or, as the case may be, insects such as bees.

[0591] Domestic animals or companion animals include, for example, mammals, such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, or in particular dogs, cats, caged birds; reptiles; amphibians or ornamental fish.

[0592] According to a specific embodiment, the compound of formula (I) is administered to a mammal.

[0593] According to another specific embodiment, the compounds of formula (I) are administered to birds, ie caged birds or in particular poultry.

[0594] According to another specific embodiment, the compounds of formula (I) are administered to farm animals or companion animals, in particular companion animals such as cats and dogs.

[0595] By using compounds of formula (I) to control animal parasites, it is intended to reduce or prevent disease, mortality and performance decline (in the case of meat, milk, wool, hides, eggs, honey, etc.), making more economical and simpler animal husbandry possible and achieving better animal health.

[0596] As used herein in the field of animal health, the terms "control" or "controlling" mean that the compounds of formula (I) can effectively reduce the incidence of the respective parasite in animals infected with such parasites to a harmless level. More specifically, "controlling" as used herein means that the compounds of formula (I) can effectively kill the respective parasite, inhibit its growth, or inhibit its reproduction.

[0597] Exemplary arthropods include, but are not limited to, arthropods from the order Anoplurida, such as Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.;

[0598] Arthropods from the order 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.;

[0599] Arthropods from the order Diptera and the suborders 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., Glossina spp., Haematobia spp., Haematopota spp. spp.), Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp.), Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.;

[0600] Arthropods from the order Siphonapterida, for example, Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.;

[0601] Arthropods from the order Heteropterida, for example, Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp.; and nuisance and hygiene pests from the order Blattodea.

[0602] Furthermore, among the arthropods, the following acari may be mentioned by way of example and without limitation: arthropods from the classes Acari (order Acarina) and Metastigmata, for example the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus (Boophilus) spp., spp.) (the genus of the multi-host tick); arthropods from the order Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilelaps spp., Varroa spp.; arthropods from the order Actinedida (Prostigmata), such as Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp. spp.), Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp.; and arthropods from the order Acaridida (order 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.

[0603] In a particular aspect, the compounds of formula (I) are effective in reducing the incidence of parasites selected from arthropods, more particularly from the order Acari and insects, in animals infected with such parasites to harmless levels.

[0604] In the field of veterinary medicine and animal husbandry, the compounds of formula (I) are administered by methods generally known in the art, such as enteral, parenteral, dermal or nasal administration in the form of suitable formulations. Administration can be carried out prophylactically, methaphylactically or therapeutically.

[0605] Therefore, one embodiment of the present invention relates to compounds of formula (I) for use as medicaments.

[0606] Another aspect relates to compounds of formula (I) for use as antiendoparasitical agents.

[0607] Another aspect relates to compounds of formula (I) for use as antiectoparasiticalagents, in particular arthropodicidal agents, more in particular insecticides or acaricides.

[0608] Another aspect of the present invention is a veterinary formulation comprising an effective amount of at least one compound of formula (I) and at least one of the following substances: 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 and / or a pharmaceutically acceptable adjuvant commonly used in veterinary formulations.

[0609] A related aspect of the invention is a process for preparing a veterinary formulation as described herein, comprising the steps of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or adjuvants, in particular with pharmaceutically acceptable excipients and / or adjuvants typically used in veterinary formulations.

[0610] Another particular aspect of the present invention is a veterinary preparation and a process for their preparation, wherein, according to the aforementioned aspect, the veterinary preparation is chosen from ectoparasiticidal preparations and endoparasiticidal preparations, more particularly from arthropodicidal preparations, even more particularly from nematocidal preparations, flatwormicidal preparations, acanthocephalicidal preparations, linguicidal preparations, insecticidal preparations and acaricidal preparations.

[0611] Another aspect relates to a method for treating parasitic infections, in particular infections by parasites selected from the ectoparasites and endoparasites mentioned herein, by administering an effective amount of a compound of formula (I) to an animal, in particular a non-human animal, in need thereof.

[0612] Another aspect relates to a method for treating a parasitic infection, in particular a parasitic infection selected from the group consisting of the ectoparasites and endoparasites mentioned herein, by administering a veterinary formulation as defined herein to an animal, in particular a non-human animal, in need thereof.

[0613] Another aspect relates to the use of a compound of formula (I) for treating parasitic infections in animals, especially non-human animals, especially parasitic infections selected from the group consisting of ectoparasites and endoparasites mentioned herein.

[0614] In the context of the animal health or veterinary fields of this application, the term "treatment" includes prophylactic, remedial preventive or therapeutic treatment.

[0615] In a particular embodiment, mixtures of at least one compound of the formula (I) with other active ingredients, in particular with endoparasiticides and ectoparasiticides, are provided for the veterinary field.

[0616] In the field of animal health, "mixture" refers not only to two (or more) different active ingredients formulated in a combined formulation and correspondingly administered together, but also to products comprising separate formulations of the individual active compounds. Thus, if more than two active compounds are to be administered, all active compounds can be formulated in a combined formulation or all active compounds can be formulated in separate formulations; also possible are mixed forms in which some active compounds are formulated in combination and some are formulated separately. Separate formulations allow the active compounds in question to be administered separately or sequentially.

[0617] The active compounds designated herein by their "common names" are known and are described, for example, in the Pesticide Manual (see above) or can be retrieved on the Internet (eg: http: / / www.alanwood.net / pesticides).

[0618] Exemplary active ingredients selected from the group consisting of ectoparasiticides as admixtures include, but are not limited to, the insecticides and acaricides listed in detail above. Other active ingredients that may be used are listed below, based on the above classification based on the current IRAC Mode of Action Classification: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-gated chloride channel blockers; (3) sodium channel modulators; (4) nicotinic acetylcholine receptor (nAChR) competitive modulators; (5) nicotinic acetylcholine receptor (nAChR) allosteric modulators; (6) glutamate-gated chloride channel (GluCl) allosteric modulators; (7) juvenile hormone mimetics; (8) various nonspecific (multi-site) inhibitors; (9) chord organ modulators; (10) mite growth inhibitors; (12) mitochondrial ATP synthase inhibitors, such as ATP disruptors; (13) 3) Oxidative phosphorylation uncouplers that disrupt the proton gradient; (14) Nicotinic acetylcholine receptor channel blockers; (15) Type 0 chitin biosynthesis inhibitors; (16) Type 1 chitin biosynthesis inhibitors; (17) Molting disruptors (especially for Diptera, i.e., two-winged insects); (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-dependent sodium channel blockers; (23) Acetyl coenzyme A (CoA) carboxylase inhibitors; (28) Ryanodine receptor modulators;

[0619] Active compounds with an unknown or undefined mode of action, for example, fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplure, flutenzin, bromopropylate, cryolite;

[0620] Compounds from other classes, for example, butacarb, dimetilan, cloethocarb, phosphocarb, pirimiphos (-ethyl), methacrifos, isopropyl o-salicylate, trichlorfon, tigolaner, sulprofos, propaphos, sebufos, pyridathion, prothoate, dichlofenthion, demeton-S-methylsulphone, isazofos, cyanofenphos, dialifos, carbophen othion), autathiofos, aromfenvinfos(-methyl), azinphos(-ethyl), chlorpyrifos(-ethyl), fosmethilan, iodofenphos, dioxabenzofos, formothion, fonofos, flupyrazofos, fensulfothion, and etrimfos;

[0621] Organochlorine compounds, such as lindane and heptachlor; or phenylpyrazoles, such as acetoprole, pyrafluprole, pyriprole, vaniliprole, and sisapronil; or isoxazolines, such as sarolaner, afoxolaner, lotilaner, and fluralaner;

[0622] Pyrethroids, for example (cis, trans) metofluthrin, profluthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbute, pyresmethrin, RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrin, cis-cypermethrin, cis- Permethrin (cis-permethrin), clocythrin, cyhalothrin (lamda-), chlovaporthrin, or halogenated hydrocarbon compounds (HCH), neonicotinoids, such as nithiazine dicloromezotiaz, triflumezopyrim, macrolides, such as nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate, benzoate; milbemycin oxime, triprene, epofenonane, diofenolan; biological agents, hormones or pheromones, for example natural products such as thuringiensin, codlemone or neem components; dinitrophenols, for example dinocap, dinobuton, binapacryl; benzoylureas, for example fluazuron, penfluron; amidine derivatives, for example chlormebuform, cymiazole, demiditraz; bee hive varroa acaricides, for example organic acids, for example formic acid, oxalic acid.

[0623] Exemplary active ingredients selected from endoparasiticides as admixtures include, but are not limited to, anthelmintic active compounds and antiprotozoal active compounds.

[0624] Antihelmintic active compounds include, but are not limited to, the following nematicidal active compounds, fluke-killing active compounds and / or tapeworm-killing active compounds:

[0625] From the macrolide class, for example, eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin, and milbemycin;

[0626] From the benzimidazoles and probenzimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole-sulphoxide, albendazole, flubendazole;

[0627] Depsipeptides, preferably cyclic depsipeptides, especially 24-membered cyclic depsipeptides, such as emodepside and PF1022A;

[0628] from the tetrahydropyrimidine class, such as morantel, pyrantel, and oxantel;

[0629] From the imidazothiazole class, such as butamisole, levamisole, and tetramisole;

[0630] From the aminophenylamidine class, such as amidantel, deacylated amidantel (dAMD), and tribendimidine;

[0631] From aminoacetonitriles, such as monepantel;

[0632] From paraherquamide, for example: paraherquamide, derquantel;

[0633] From the salicylanilide class, such as tribromsalan, bromoxanide, brotianide, clioxanide, closantel, niclosamide, oxyclozanide, and rafoxanide;

[0634] From substituted phenols, for example: nitroxynil, bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan;

[0635] From organophosphates, such as trichlorfon, naphthalofos, dichlorvos / DDVP, crufomate, and haloxon;

[0636] From piperazinones / quinolines, such as praziquantel and epsiprantel;

[0637] From the piperazine class, e.g. piperazine, hydroxyzine;

[0638] From the tetracycline family, such as tetracycline, chlorotetracycline, doxycycline, oxytetracyclin, and rolitetracycline;

[0639] From various other classes, for example: bunamidine, niridazole, resorantel, omphalotin, oltipraz, nitroscanate, nitroxynile, oxamniquine, mirasan, miracil, lucanthone, hycanthone, hetolin, emetine, diethylcarbamazine, diclofenac, diamfenetide, clonazepam, bephenium, amoscanate, clorsulon.

[0640] Antiprotozoal active compounds include, but are not limited to, the following active compounds:

[0641] From the triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril;

[0642] From the class of polyether ionophores, such as monensin, salinomycin, maduramicin, and narasin;

[0643] From macrolides, such as milbemycin and erythromycin;

[0644] From the quinolone class, such as enrofloxacin and pradofloxacin;

[0645] From the quinine family, such as chloroquine;

[0646] From the pyrimidine class, for example: pyrimethamine;

[0647] From the sulfonamide class, such as sulfaquinoxaline, trimethoprim, and sulfaclozin;

[0648] From thiamines, such as amprolium;

[0649] From the lincosamide class, such as clindamycin;

[0650] From carbonylanilides, such as imidocarb;

[0651] From the nitrofuran class, such as nifurtimox;

[0652] From quinazolinone alkaloids, such as halofuginone;

[0653] From various other species, for example: oxamniquin, paromomycin;

[0654] From microbial vaccines or antigens, such as Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria toxicophilus, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, and Dictyocaulus viviparus.

[0655] All mixing components mentioned can optionally form salts with suitable bases or acids, if their functional groups are capable of forming salts with suitable bases or acids.

[0656] Vector control

[0657] The compounds of formula (I) can also be used for disease vector control. For the purposes of the present invention, a disease vector is an arthropod, particularly an insect or arachnid, that is capable of transmitting pathogens (such as viruses, worms, single-cell organisms, and bacteria) from a reservoir (plants, animals, humans, etc.) to a host. Pathogens can be transmitted to the host mechanically (e.g., by trachoma transmitted by non-biting flies) or by injection (e.g., by mosquito-transmitted Plasmodium).

[0658] Examples of vectors and the diseases or pathogens they transmit are:

[0659] 1)Mosquito

[0660] - Anopheles: malaria, filariasis;

[0661] - Culex mosquitoes: transmission of Japanese encephalitis, other viral diseases, filariasis, and other helminths;

[0662] - Aedes mosquito: yellow fever, dengue fever, other viral diseases, filariasis;

[0663] - Simuliidae: transmission of worms, especially Onchocerca volvulus;

[0664] - Psychodidae: transmission of leishmaniasis

[0665] 2) Lice: skin infection, epidemic typhus;

[0666] 3) Fleas: plague, endemic typhus, tapeworms;

[0667] 4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterial diseases;

[0668] 5) Mites: mite disease, epidemic typhus, rickettsial pox, tularemia, St. Louis encephalitis, tick-borne encephalitis (TBE), Crimean-Congo hemorrhagic fever, borreliosis;

[0669] 6) Ticks: borellioses such as Borrelia burgdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), babesiosis (Babesia canis subsp.), ehrlichiosis.

[0670] Examples of disease vectors within the meaning of the present invention are insects that can transmit plant viruses to plants, such as aphids, flies, leafhoppers or thrips. Other disease vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.

[0671] Further examples of disease vectors in the sense of the present invention are insects and arachnids capable of transmitting pathogens to animals and / or humans, such as mosquitoes, in particular Aedes; Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria); and Culex; psychoodids, such as Phlebotomus, Lutzomyia; lice; fleas; flies; mites and ticks.

[0672] Vector control is also possible if the compounds of the formula (I) are resistance-breaking.

[0673] The compounds of formula (I) are suitable for preventing diseases and / or pathogens borne by vectors. Therefore, another aspect of the present invention is the use of the compounds of formula (I) for vector control, for example in agriculture, gardening, landscapes and leisure facilities, and in the protection of materials and stored products.

[0674] Protection of industrial materials

[0675] The compounds of the formula (I) are suitable for protecting industrial materials against infestation or destruction by insects, for example from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Pseudocoptera and Gnaphalidae.

[0676] Industrial materials in the context of the present invention are understood to mean inanimate materials such as preferably plastics, adhesives, sizes, paper and card, leather, wood, processed wood products and coating compositions. Particular preference is given to the use according to the invention for protecting wood.

[0677] In another embodiment, the compounds of formula (I) are used together with at least one other insecticide and / or at least one fungicide.

[0678] In a further embodiment, the compounds of the formula (I) are in the form of ready-to-use insecticides, ie they can be applied to the material in question without further modification. Suitable further insecticides or fungicides are in particular those mentioned above.

[0679] Surprisingly, it has also been found that compounds of formula (I) can be used to protect objects that come into contact with saltwater or brackish water (in particular hulls, screens, nets, buildings, moorings and signaling systems) from fouling. Likewise, compounds of formula (I) can be used alone or in combination with other active compounds as antifouling agents.

[0680] Control of animal pests in the health sector

[0681] The compounds of formula (I) are suitable for controlling animal pests in the sanitary sector. In particular, the present invention can be applied to indoor areas, sanitary areas, and the protection of stored products, especially for controlling insects, arachnids, ticks, and mites encountered in enclosed spaces (such as homes, factory floors, offices, vehicle cabins, and animal breeding facilities). To control animal pests, the compounds of formula (I) are used alone or in combination with other active compounds and / or adjuvants. They are preferably used in indoor insecticide products. The compounds of formula (I) are effective against sensitive and resistant species and against all developmental stages.

[0682] These pests include, for example, pests from the class Arachnida, from the orders Scorpiones, Araneae and Opiliones; from the classes Chilopoda and Diplopoda; from the class Insecta, from the order Blattodea; from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Pediculus, Psoralea, Hoplites or Orthoptera, Siphonaptera and Silverfish; and pests from the order Malacostraca, etc.

[0683] They are used, for example, in the following ways: aerosols, non-pressurized spray products (such as pump sprays and atomizer sprays), automatic fogging systems, sprays, foams, gels, evaporation products with evaporation tablets made of cellulose or plastic, liquid evaporators, gel and film evaporators, propeller-driven evaporators, unpowered or passive evaporation systems, moth-trapping papers, moth-trapping bags and moth-trapping glue, as granules or powders, in baits for broadcasting or in bait stations.

[0684] Abbreviations and symbols

[0685] AcOH: acetic acid

[0686] aq.: containing water

[0687] BINAP: 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

[0688] br.: broad peak

[0689] d: Twin Peaks

[0690] dppf: 1,1'-bis(diphenylphosphino)ferrocene

[0691] DCC: N,N'-dicyclohexylcarbodiimide

[0692] DCM: dichloromethane

[0693] DIPEA: diisopropylethylamine

[0694] DIAD : diisopropyl azodicarboxylate

[0695] DMF: N , N -Dimethylformamide

[0696] DMSO: dimethyl sulfoxide

[0697] ee: enantiomeric excess

[0698] eq.: equivalent

[0699] ES: electrospray ionization

[0700] EtOAc: ethyl acetate

[0701] HATU: 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate

[0702] HOBt: 1-Hydroxybenzotriazole hydrate

[0703] HPLC: High Performance Liquid Chromatography

[0704] i PrOH: isopropyl alcohol

[0705] J : coupling constant

[0706] LCMS: Liquid chromatography-mass spectrometry

[0707] m / z : mass-to-charge ratio

[0708] M: molar concentration

[0709] m: multiple peaks

[0710] MeCN: acetonitrile

[0711] MeOH: methanol

[0712] MTBE: tert-butyl methyl ether

[0713] NMR: Nuclear Magnetic Resonance

[0714] q: quartet

[0715] rt: room temperature

[0716] R t : Retention time

[0717] s: single peak

[0718] sat.: saturated

[0719] T: temperature

[0720] TMP: 2,2,6,6-tetramethylpiperidine

[0721] t: triplet

[0722] T3P ® :Propylphosphonic anhydride

[0723] THF: Tetrahydrofuran

[0724] wt.: weight

[0725] XantPHOS: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (CAS RN 161265-03-8)

[0726] δ: chemical shift

[0727] λ: wavelength.

[0728] Description of Methods and Intermediates

[0729] Compounds of formula I can be prepared as shown in Scheme 1 below, wherein R 1 、R 2 、R 3 、R 4 、R 5 、R 6 As defined above.

[0730] Solution 1

[0731]

[0732] The synthesis begins with the residue R 5 and R 6 A pyrazine of formula (II) and a group X which may be chlorine, bromine or iodine 1 These compounds are commercially available or can be prepared according to methods described in the art. In the first transformation, 1 The adjacent hydrogen atoms are removed and replaced by metal fragments consisting of a main group metal such as Li, Mg, Zn and a suitable ligand L. F. Buron, N. Pié, A. Turck, G, Quéguigner, J . Org . Chem . 2005, 70 An example of such a transformation is given in , 2616-2621, which demonstrates the lithiation of 2-chloropyrazine with Li-TMP (2,2,6,6-tetramethylpiperidinyl-lithium base) in THF. T. Klatt, JT Markiewicz, C. Sämann, P. Knochel, J . Org . Chem. 2014, 79 , 4253-4269 are summarized in the review of other TMP-based reagents. The metallated intermediate (III) is then trapped in situ with the aldehyde (IV) to produce the secondary alcohol (V). The metallation and reaction with the aldehyde are usually carried out in one pot in a polar aprotic solvent such as THF, diethyl ether, or dioxane. The temperature in the metallation step is usually below 0°C, preferably at -78°C in a dry ice bath. After the addition of the aldehyde, the temperature can be raised to 0°C or even room temperature. Instead of a one-pot procedure, the organometallic intermediate can also be prepared in advance and then added to a solution of the aldehyde in a suitable aprotic solvent (such as, for example, THF, diethyl ether, or toluene).

[0733] The subsequent step is to replace the hydroxyl group of intermediate (V) with a fully protected nitrogen to obtain the intermediate of formula (VII). 1 and PG 2 There may be two independent protecting groups or they may be linked to form a cyclic protecting group. 1 and PG 2 The other one in can also represent hydrogen. Examples of protecting groups suitable for protecting amino functional groups can be found in TW Greene, PGM Wuts "Protective Groups in Organic Chemistry" 3rd edition, Wiley Interscience, New York 1999, such as the Boc- group. Preferably, a phthalimide protecting group is used. The hydroxyl group can be replaced as follows: by methods known in the art, such as Appel reaction, treatment with sulfuryl chloride, etc., the alcohol is converted into a halide and then nucleophilically substituted with phthalimide, or preferably, at a temperature of from -40°C to 100°C, preferably from 0°C to room temperature, in a suitable solvent such as THF, in a Mitsunobu reaction with DIAD and triphenylphosphine, the intermediate (V) is directly converted with phthalimide.

[0734] R 4 The introduction occurs using a leaving group X 2 In the next step of the cross-coupling reaction of reagent (VIII). 2 It can be a trialkylstannyl residue, a boronic acid, a boric acid ester or a metal fragment M (L) containing a metal such as Ni, Zn, Mg and a suitable ligand L. nCross-coupling reactions are typically catalyzed by transition metal catalysts, such as palladium or copper catalysts with appropriate ligands. 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.

[0735] A variant of the cross-coupling reaction can be to use a trialkyltrialkylstannyl residue, a boronic acid, a boronate ester or a metal fragment M (L) with a metal such as Ni, Zn, Mg and a suitable ligand L. n ) replaces the moiety X from intermediate (VII) 1 In this case, the intermediate (VIII) must carry a group X selected from, for example, Cl, Br, I, triflate or the like. 2 .

[0736] X 1 = Cl, Br or I and X 2 = Suitable conditions for the coupling of trialkylstannyl, boronic acid or boronate may involve the use of 0.01-0.5 equivalents of a palladium source such as PdCl2(dppf) x DCM, palladium diacetate, tetrakis(triphenylphosphine)palladium or other compounds with the ligand. The ligand may be selected from a phosphine ligand or N -Heterocyclic carbene ligands, for an overview of some ligands see R. Martin, SL Buchwald, Acc . Chem . Res . 2008, 61 , 1461-1473.

[0737] The product of the cross-coupling reaction (IX) must be deprotected in the next step. In the case of a phthalimide protecting group, this can be achieved by reacting (IX) with hydrazine hydrate in a suitable solvent such as ethanol at or above room temperature.

[0738] The compound of formula (I) can be obtained by reacting the intermediate (X) with a carboxylic acid derivative (XI), wherein X 3 Is Cl, O-acyl or OH. In the case where X is Cl or O-acyl, in the presence of a base such as, for example, DIPEA, triethylamine or N(X) and (XI) are reacted directly in the presence of methylmorpholine in a solvent such as DMF, THF or the like. In the case where X is OH, the acid (XI) needs to be activated using a coupling agent such as HATU, TBTU, TCTU, PyBOP, etc., or it can be converted into the corresponding acid chloride or anhydride before reacting it with (X) as described above. The resulting product (Ia) is a compound of the present invention, wherein R 1 is H. In order to obtain R 1 For compounds other than hydrogen, an alkylation reaction with an alkylating agent (XII) can be used. Examples of leaving groups LG are Cl, Br, I, tosylate, mesylate, or triflate. The reaction can be carried out by mixing reagents (Ia) and (XII) with a base such as K2CO3 or DIPEA in a suitable solvent such as acetonitrile or DMF and allowing them to react at a temperature ranging from 20 to 100°C. The compound of formula (Ib) can then be isolated and, if necessary and desired, purified using techniques well known in the art such as chromatography.

[0739] If in compound (I) R 4 is a pyridine-group, then in the above scheme 1, it is preferred that X 1 is Cl, X 2 is Zn-Cl, the Pd-catalyst is Pd2(dba)3catalyst and the ligand L is X-Phos.

[0740] If in compound (I) R 4 is a pyrimidine-group, then in the above scheme 1, it is preferred that X 1 is Cl, X 2 is SnBu3, the Pd-catalyst is PdCl2*2APhos catalyst and ZnCl2 is added as an additive.

[0741] If in compound (I) R 4 is a thiazole-group, then in the above scheme 1, it is preferred that X 1 is Cl, X 2 is SnBu3, the Pd-catalyst is PdCl2*2PPh3 catalyst and the ligand L is PPh3.

[0742] Option 2

[0743]

[0744] In a variation of the synthetic route described above, the Mitsunobu reaction and the cross-coupling reaction can be applied in the reverse order as shown in Scheme 2. In this case, R 4Introducing one of the above cross-coupling methods produces intermediate XIII, which is then further converted to intermediate IX by the Mitsunobu reaction as described above. In some cases, this may offer advantages in terms of yield or practicality. 1 and PG 2 For the meaning of , see the definition above.

[0745] In R 4 In the case of the combination of the nitrogen atom and the pyrazine moiety, X in intermediates V and VII 1 is preferably halogen (especially Cl, Br or I), and X 2 Is with R 4 Specifically, this applies to R 4 is the case of an optionally substituted pyrazole or imidazole. The general strategy for these molecules can follow the order of steps shown in Scheme 1 or Scheme 2. Preferably, the introduction of the pyrazole or imidazole is performed before the introduction of the amine, as shown in Scheme 2. The actual cross-coupling step is performed using a metal catalyst, an optional ligand, a base and a solvent. Metal catalysts that can be used for this step include copper (I) and copper (II) salts, preferably copper (I) halides, such as copper (I) iodide. The use of a ligand may be beneficial, and the choice of a suitable 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. A catalytic amount of the metal catalyst and ligand is used, typically in the range of 0.01-0.5 molar equivalents of each. As the base, an alkali metal or alkaline earth metal carbonate, such as calcium carbonate, sodium carbonate, potassium carbonate, or cesium carbonate, can be used. Solvents include 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 higher, preferably at 100-120°C.

[0746] If R 4 is pyrazole, then preferred conditions for the cross coupling include the use of 0.3 equivalents of copper (I) iodide, 0.3 equivalents of trans- N,N,N',N' -Tetramethylcyclohexane-1,2-diamine, excess potassium carbonate.

[0747] In some cases, the compounds of the present invention can be prepared by introducing R 4 These operations can be performed on the R 2 part, or as an alternative, in the presence of R 2 This was previously done using a suitably protected intermediate according to formula IX (see Scheme I). For example, at R 4The ester groups on R can be saponified by standard methods. Preferred methods for ester saponification include lithium hydroxide or sodium hydroxide in solvents such as methanol and mixtures of 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 by using a coupling agent such as TBTU, HATU, EDCI or other reagents known in the art. Carboxylic acid esters can also be converted to cyanides using Burgess reagent. Alternatively, the carboxylic acid can be converted to an amine using a Curtius rearrangement, and the resulting amino group can then be acylated to produce an amino group attached to R via a nitrogen atom by using a coupling agent such as TBTU, HATU, EDCI or other reagents known in the art. 4 of carboxamide.

[0748] The process according to the invention for preparing the compound of formula (I) is preferably carried out using a diluent. Useful diluents for carrying out the process according to the invention, like water, are inert solvents. Examples include: halogenated hydrocarbons (e.g. chlorinated hydrocarbons such as tetrachloroethylene, tetrachloroethane, dichloropropane, dichloromethane, 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, phenethyl ether, cyclohexyl methyl ether, dimethyl ether, diethyl ether, dipropyl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, 1,4-dimethoxy-1,4-diol ...

[0014] The present invention also includes but is not limited to: cyclopentane, dioxane, dichlorodiethyl ether and polyethers of ethylene oxide and / or propylene oxide), amines (for example trimethylamine, triethylamine, tripropylamine, tributylamine, N-methylmorpholine, pyridine and tetramethylenediamine), nitrohydrocarbons (for example nitromethane, nitroethane, nitropropane, nitrobenzene, chloronitrobenzene, o-nitrotoluene); nitriles (for example 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 (for example dimethyl sulfone, diethyl sulfone, dipropyl sulfoxide, sulfone, dibutyl sulfone, diphenyl sulfone, dihexyl sulfone, methyl ethyl sulfone, ethyl propyl sulfone, ethyl isobutyl sulfone and pentamethylene sulfone), aliphatic, alicyclic or aromatic hydrocarbons (for example pentane, hexane, heptane, octane, nonane and technical hydrocarbons), and so-called "white spirits", the components of which have a boiling point range of, for example, 40° C. to 250° C., cymene, petroleum fractions with a boiling point range of 70° C. to 190° C., cyclohexane, methylcyclohexane, petroleum ether, light petroleum, benzene, toluene, xylene, esters (for example methyl acetate, ethyl acetate, butyl acetate and ethyl acetate) isobutyl carbonate, dimethyl carbonate, dibutyl carbonate and ethylene carbonate), amides (such as 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-imidazolidinedione, N-formylpiperidine, N,N'-diformylpiperazine) and ketones (such as acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone).

[0749] It is also possible to carry out the process according to the invention in mixtures of the solvents and diluents mentioned.

[0750] When carrying out the process according to the invention, the reaction temperature can be varied within a relatively wide range. Typically, temperatures of -30°C to +150°C, preferably -10°C to +100°C, are employed.

[0751] The process according to the invention is usually carried out at atmospheric pressure. However, it is also possible to carry out the process according to the invention at elevated or reduced pressure (usually at an absolute pressure of 0.1 to 15 bar).

[0752] To carry out the method according to the invention, the starting materials are generally used in approximately equimolar amounts. However, a relatively large excess of one of the components may also be used. The reaction is generally carried out in a suitable diluent in the presence of a reaction aid, optionally also under a protective gas atmosphere (e.g., nitrogen, argon, or helium), and the reaction mixture is generally stirred at the desired temperature for several hours. Post-processing is carried out by conventional methods (see the Preparation Examples).

[0753] The basic reaction auxiliaries used for carrying out the process according to the invention may be all suitable acid binders. Examples include: alkaline earth metal or alkali metal compounds (e.g. hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium), amidine 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, in particular tertiary amines (e.g. triethylamine, trimethylamine, tribenzylamine, triisopropylamine). (e.g., 1,2-dimethylenediamine ...

[0754] Acidic reaction auxiliaries for carrying out the process according to the invention include all inorganic acids (for example hydrohalic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid, as well as sulfuric acid, phosphoric acid, phosphorous acid, nitric acid), Lewis acids (for example aluminum(III) chloride, boron trifluoride or its etherates, 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 p-toluenesulfonic acid).

[0755] The following examples further illustrate and describe the present invention without limiting the present invention.

[0756] Preparation Example

[0757] Analytical methods

[0758] Method 1 (LC-MS)

[0759] Instrument: Agilent MS Quad 6150; HPLC: Agilent 1290; column: Waters Acquity UPLCHSS T3 1.8 μm 50 x 2.1 mm; eluent A: 1 L water + 0.25 mL 99% 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, column oven temperature: 50°C; flow rate: 1.20 mL / min; UV-detection: 205-305 nm.

[0760] Method 2 (LC-MS)

[0761] MS instrument: Thermo Scientific FT-MS; UHPLC+ instrument: Thermo Scientific UltiMate 3000; column: Waters, HSST3, 2.1 x 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; column oven temperature: 50°C; flow rate: 0.90 mL / min; UV-detection: 210 nm / optimal integration path 210-300 nm.

[0762] Method 3 (LC-MS)

[0763] Instrument: Waters Single Quad MS system; instrument: Waters UPLC Acquity; column: Waters BEHC18 1.7 μ50 x 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; column oven temperature: 50°C; flow rate: 0.45 mL / min; UV-detection: 210 nm.

[0764] Method 4 (LC-MS) Analytical Method E

[0765] Instrument: SHIMADZU LCMS-UFLC 20-AD-LCMS 2020 MS detector; column: Ascentis ExpressC18 2.7 μm, 50 x 3.0 mm; eluent A: water + 0.05 vol% trifluoroacetic acid, eluent B: acetonitrile + 0.05 vol% trifluoroacetic acid; gradient: specified for each compound; flow rate 1.2 mL / min; temperature: 40°C; PDA scan: 190-400 nm.

[0766] Method 5 (LC-MS) Analytical Method E1

[0767] Instrument: SHIMADZU LCMS-UFLC 20-AD-LCMS 2020 MS detector; column: Ascentis ExpressC18 2.7 μm, 50 x 2.1 mm; eluent A: water + 0.1 vol% formic acid, eluent B: acetonitrile + 0.1 vol% formic acid; gradient: specified for each compound; flow rate 1.5 mL / min; temperature: 40°C; PDA scan: 190-400 nm.

[0768] Method 6 (LC-MS) Analytical Method F

[0769] 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 vol% trifluoroacetic acid, eluent B: acetonitrile + 0.05 vol% trifluoroacetic acid; gradient: specified for each compound; flow rate 1.5 mL / min; temperature: 40°C; PDA scan: 190-400 nm.

[0770] Method 7 (Chiral HPLC)

[0771] Column: Daicel Chiralpak ID, 5 μm 250 x 4.6 mm; eluent A: isohexane, eluent B: 2-propanol, A:B isocratic = 1:1, 40°C; flow rate: 1.0 mL / min; UV-detection: 220 nm.

[0772] Method 8 (Optical Rotation)

[0773] Device: Anton Paar polarimeter MCP200

[0774] Specific optical rotation [α] (depends on wavelength, temperature, optical approach, solvent and concentration).

[0775] Method 9 (HPLC-MS)

[0776] MS system: Waters TOF instrument; UPLC system: Waters Acquity I-CLASS; column: Waters Acquity UPLC HSS T3 1.8 μm 50 x 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; column oven: 50°C; flow rate: 0.40 ml / min; UV-detection: 210 nm.

[0777] Method 10 (HPLC-MS)

[0778] MS system: Waters TOF instrument; UPLC system: Waters Acquity I-CLASS; column: Waters Acquity UPLC HSS T3 1.8 μm 50 x 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; column oven: 50°C; flow rate: 0.35 ml / min; UV-detection: 210 nm.

[0779] Method 11 (HPLC-MS)

[0780] Instrument: Waters ACQUITY SQD UPLC system; column: Waters Acquity UPLC HSS T3 1.8 μm 50 x 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 Column oven: 50°C; flow rate: 0.40 ml / min; UV-detection: 210 nm.

[0781] General synthetic methods

[0782] General Synthesis Method 1

[0783] Synthesis of MIDA boronate

[0784] 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.

[0785] The procedure was carried out as described herein on a scale of approximately 100 mmol (calculated based on the 2-bromopyridine derivative). The 2-bromopyridine derivative (1 equivalent) and tripropan-2-yl borate (1.4 equivalents) were dissolved in THF (200 mL) and the solution was cooled to -78°C. n-Butyllithium (2.5 M in hexane, 1.2 equivalents) was slowly added over 90 minutes. Stirring at -78°C was maintained for an additional 60 minutes, after which the cooling bath was removed and the mixture allowed to warm to ambient temperature. In a separate 3-necked round-bottom flask equipped with a distillation apparatus and a fixed internal thermometer, a solution of 2,2'-(methylimino)diacetic acid (1.6 equivalents) in DMSO (dried over 3-μm molecular sieves, 150 mL) was heated to 125-130°C. The suspension of the borate ester in THF was slowly added over approximately 2 hours, distilling the THF while maintaining the temperature between 115-125°C. Finally, the mixture was stirred for a further 20 min and then overnight.DMSO was distilled under vacuum and the residue was adsorbed on Celite and chromatographed on 340 g of silica gel using a ternary gradient of dichloromethane-ethyl acetate followed by ethyl acetate-THF.

[0786] General Synthesis Method 2

[0787] Cross-coupling of MIDA boronates with halogenated pyrazines

[0788] Under argon, (rac)-1-(3-bromopyrazin-2-yl)ethane-1-ol (1 equivalent), MIDA boronate (1.2 equivalents) and diethanolamine (1.0 equivalents) were dissolved in DMF (approximately 4 mL / mmol of halopyrazine). 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 with 3 portions of MTBE. The organic extract was dried over anhydrous sodium sulfate, evaporated, and purified by chromatography on silica gel using a cyclohexane-ethyl acetate gradient to give the title compound.

[0789] General Synthesis Method 3

[0790] Mitsunobu reaction

[0791] The substituted (pyrazin-2-yl)ethan-1-ol (1 equivalent) was dissolved in THF (about 3.0 mL / mmol), and 1 H -isoindole-1,3(2 H )-dione (1.50 equiv) and triphenylphosphine (1.50 equiv). The mixture was cooled to 0°C, then DIAD (1.50 equiv) was slowly added and the mixture was stirred for another 30 min. 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.

[0792] General Synthesis Method 4

[0793] Hydrazinolysis of phthalimide groups

[0794] The phthalimide-protected amine (1 equivalent) was dissolved in ethanol (approximately 10 mL / mmol) and hydrazine hydrate (80% in water, 5 equivalents) was added. The mixture was heated to reflux for 1 hour, then poured into water and extracted with 3 parts of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and evaporated. Optionally, the crude product was purified by flash chromatography to produce the pure title compound.

[0795] General Synthesis Method 5

[0796] Amide coupling

[0797] Amine (1.0 equivalent), carboxylic acid (1.3 equivalents) and DIPEA (3.0 equivalents) were dissolved in DMF (approximately 0.17 mmol amine / mL DMF). The solution was cooled to 0°C on an ice-water bath and HATU (1.5 equivalents) was added. The cooling bath was removed and the mixture was stirred for 30 min. Water was then added. The precipitated product was collected on a filter funnel, dried under vacuum and finally purified by preparative HPLC (RP-C18, water-acetonitrile gradient with 0.1% TFA).

[0798] General Synthesis Method 6

[0799] Copper-catalyzed coupling of azoles

[0800] (Race)-1-(3-bromopyrazin-2-yl)ethan-1-ol (Intermediate 22A, 1 eq) was dissolved in toluene (3.0 mL / 1.0 mmol of bromopyrazine), and oxazole (1.5 eq), potassium carbonate (2.5 eq), copper (I) iodide (0.3 eq) and trans- N,N,N',N' -tetramethylcyclohexane-1,2-diamine (0.3 equivalent). The mixture is heated to reflux and kept for 1 h and then poured into water. It is extracted with three parts of ethyl acetate, the combined organic extracts are washed twice with 20% ammonia water, washed once with water, and finally washed once with salt water. The organic phase is dried over anhydrous sodium sulfate, evaporated and the residue is purified by cyclohexane-ethyl acetate gradient on silica gel. Optionally, the crude product is purified another time by preparative HPLC (RP-C18 column, with water-acetonitrile gradient with 0.1% TFA) to obtain the title compound.

[0801] Synthetic intermediates

[0802] Intermediate 1A

[0803] (Racemic)1-(3-chloropyrazin-2-yl)ethan-1-ol

[0804]

[0805] 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 on an acetone-dry ice bath. n-Butyl lithium (2.5 M in hexane, 25 mL, 64 mmol) was added dropwise so that the temperature did not exceed -70°C. Then, stirring was maintained at -78°C for 30 min. Then, 2-chloropyrazine (5.73 g, 50.0 mmol) was added dropwise and the mixture was stirred for 1 h. After this time, acetaldehyde (5.6 mL, 100 mmol) was added and the mixture was warmed to room temperature and stirred for another 4 h. 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 vacuum. The crude product was purified by chromatography on silica gel using a gradient of cyclohexane and 0-40% ethyl acetate. This afforded 4.60 g (100% purity, 58% yield) of the title compound.

[0806] LC-MS (Method 1): R t = 0.51 min; low ionization observed.

[0807] ¹H-NMR (400 MHz, DMSO- d 6 ) 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).

[0808] Intermediate 2A

[0809] (rac)-2-[1-(3-chloropyrazin-2-yl)ethyl]-1 H -Isoindole-1,3(2)-dione

[0810]

[0811] (Racemic) 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-(2 H)-diketone (6.40 g, 43.5 mmol) and triphenylphosphine (11.4 g, 43.5 mmol), then the mixture is cooled on ice bath, and lentamente DIAD (7.8 mL, 95% purity, 44 mmol) is added. Reactant is warmed to ambient temperature and stirred for 2 h. The distillation solvent is also directly loaded onto silica gel column (100 g silica gel) with resistates, and uses the gradient of cyclohexane and 0-35% ethyl acetate to carry out chromatography separation. Obtain 5.37 g (98% purity, 63% yield) title compound.

[0812] LC-MS (Method 2): R t = 1.69 min; MS (ESIpos): m / z = 288 [M+H] +

[0813] ¹H-NMR (600 MHz, DMSO- d 6 ) 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).

[0814] Intermediate 3A

[0815] (rac)-2-{1-[3-(pyridin-2-yl)pyrazin-2-yl]ethyl}-1 H -isoindole-1,3(2 H )-dione

[0816]

[0817] Reactions were performed in flame-dried glassware under dry argon. J . Org . Chem . 2010, 75 , 8330-8332, the preparation of the organozinc reagent (solution A) was carried out.

[0818] Solution A: Charge isopropylmagnesium chloride (2.0 M in THF, 2.75 mL, 5.5 mmol) to a 3-necked round-bottom flask with a stir bar. Add neat 2-bromopyridine (0.476 mL, 5.0 mmol, 1.0 equiv) dropwise to the mixture at a temperature not exceeding 30°C. Stir the mixture at room temperature for 3 h. Then, add zinc chloride (1.9 M in THF, 3.16 mL, 6.0 mmol) dropwise at a temperature not exceeding 30°C, and continue stirring at room temperature for an additional 60 min. Use this solution as is in the subsequent cross-coupling reaction.

[0819] 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]-1-[ ... H -isoindole-1,3(2 H )-dione (Intermediate 2A, 288 mg, 1.00 mmol) and stirring was continued at 65 °C for another 15 min.

[0820] Finally, an aliquot of solution A (2.0 mL, 1.5 mmol) was added all at once to solution B, and the mixture was stirred at 65°C for 7 hours. Water (3.0 mL) and concentrated aqueous sodium bicarbonate solution (3.0 mL) were added, and the mixture was extracted with ethyl acetate. 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). This yielded 219 mg (99% purity, 66% yield) of the title compound.

[0821] LC-MS (Method 2): R t = 1.51 min; MS (ESIpos): m / z = 331 [M+H] +

[0822] ¹H-NMR (600 MHz, DMSO- d 6) 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).

[0823] Intermediate 4A

[0824] (rac)-1-[3-(pyridin-2-yl)pyrazin-2-yl]ethan-1-amine

[0825]

[0826] (rac)-2-{1-[3-(pyridin-2-yl)pyrazin-2-yl]ethyl}-1 H -isoindole-1,3(2 H )-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.

[0827] LC-MS (Method 3): R t = 0.92 min; MS (ESIneg): m / z = 199 [MH] -

[0828] ¹H-NMR (600 MHz, DMSO- d 6) 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).

[0829] Intermediate 5A

[0830] (rac)-2-(1-(3-(thiazol-2-yl)pyrazin-2-yl)ethyl)isoindoline-1,3-dione

[0831]

[0832] Under N2 atmosphere, at room temperature, (rac)-2-[1-(3-chloropyrazin-2-yl)ethyl]-1 H -isoindole-1,3(2)-dione (Intermediate 2A, 1.2 g, 4.17 mmol), dichlorobis(triphenylphosphine)palladium(II) (293 mg, 0.42 mmol) were reacted in N , N-2-(tributylstannyl)thiazole (1.9 g, 5.01 mmol) was added to a solution of dimethylformamide (24 mL). The resulting mixture was stirred at 85 ° C overnight under an N2 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 vacuum. The residue was purified by silica gel chromatography (ethyl acetate: petroleum ether = 1: 3) to provide 512 mg (31% purity) of the product as a white solid.

[0833] 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] + .

[0834] Intermediate 6A

[0835] (rac)-1-(3-(thiazol-2-yl)pyrazin-2-yl)ethan-1-amine;

[0836]

[0837] 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 h. After cooling to room temperature, the solvent was removed in vacuo, ethyl acetate was added, and the solution was stirred for 30 min. The solid was then filtered off, and the filtrate was concentrated to give 300 mg of crude product as a yellow solid.

[0838] 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] + .

[0839] Intermediate 7A

[0840] 5-tert-Butylnicotinic acid

[0841]

[0842] Under N2 atmosphere at-70 ℃ to 5-bromonicotinic acid (4.0 g, 19.99 mmol) and cuprous iodide (I) (380 mg, 2.00 mmol) in tetrahydrofuran (100 mL) solution of tert-butylmagnesium chloride in tetrahydrofuran (1.7 M, 29.4 mL, 50.0 mmol) was added dropwise. Then the mixture was stirred at room temperature overnight. By carefully adding ammonium chloride solution, the reaction was quenched. The mixture obtained was concentrated and poured into water, then extracted with ethyl acetate. The organic layers were merged, dried over anhydrous sodium sulfate and concentrated. Residue was purified by silica gel chromatography to produce 80 mg of the desired product as a white solid.

[0843] 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] + .

[0844] Intermediate 8A

[0845] (rac)-2-(1-(3-(pyrimidin-2-yl)pyrazin-2-yl)ethyl)isoindoline-1,3-dione

[0846]

[0847] Under N2 atmosphere, (rac)-2-[1-(3-chloropyrazin-2-yl)ethyl]-1 H -isoindole-1,3(2)-dione (Intermediate 2A, 1.3 g, 4.52 mmol) N,N -A solution in dimethylformamide (39 mL) was added Pd(AMPhos)2Cl2 (CAS RN 887919-35-9, 0.3 g, 0.45 mmol), ZnCl2 (0.6 g, 4.52 mmol) and 2-(tributylstannyl)pyrimidine (2.5 g, 6.78 mmol). 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 organic layers were combined and concentrated under vacuum. The residue was purified by silica gel chromatography (ethyl acetate: petroleum ether = 1:5) to provide 600 mg of product as a white solid (40% yield).

[0848] Intermediate 9A

[0849] (rac)-1-(3-(pyrimidin-2-yl)pyrazin-2-yl)ethan-1-amine

[0850]

[0851] 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 h. After cooling to room temperature, the solvent was removed in vacuo, ethyl acetate was added, and the solution was stirred for 30 min. The solid was then filtered off, and the filtrate was concentrated to yield 312 mg (85%) of the crude product as a yellow solid.

[0852] 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] + .

[0853] Intermediate 10A

[0854] 2-(5-chloropyridin-2-yl)-6-methyl-1,3,6,2-dioxazaboroctane-4,8-dione

[0855]

[0856] 13.6 g (100% purity, 49% yield) of the title compound were synthesized from 2-bromo-5-chloropyridine (20.0 g, 104 mmol) according to General Synthesis Method 1 and obtained as a crystalline solid.

[0857] LC-MS (Method 2): R t = 0.96 min; MS (ESIpos): m / z = 269 [M+H] +

[0858] ¹H-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).

[0859] Other MIDA boronates were prepared by General Synthetic Method 1:

[0860] Intermediate 11A

[0861] 6-Methyl-2-[5-(trifluoromethyl)pyridin-2-yl]-1,3,6,2-dioxazaboroctane-4,8-dione

[0862]

[0863] 2.56 g (100% purity, 38% yield) of the title compound were synthesized from 2-bromo-5-trifluoromethylpyridine (5.00 g, 22.1 mmol) according to General Synthesis Method 1 and obtained as a crystalline solid.

[0864] LC-MS (Method 2): R t = 1.19 min; MS (ESIpos): m / z = 303 [M+H] +

[0865] ¹H-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).

[0866] Intermediate 12A

[0867] 2-(5-Methoxypyridin-2-yl)-6-methyl-1,3,6,2-dioxazaboroctan-4,8-dione

[0868]

[0869] 3.25 g (95% purity, 22% yield) of the title compound were synthesized from 2-bromo-5-methoxypyridine (10.0 g, 53.2 mmol) according to General Synthesis Method 1 and obtained as a crystalline solid.

[0870] LC-MS (Method 3): R t = 0.88 min; MS (ESIpos): m / z = 265 [M+H] +

[0871] 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).

[0872] Intermediate 13A

[0873] (rac)-1-[3-(5-chloropyridin-2-yl)pyrazin-2-yl]ethan-1-ol

[0874]

[0875] Following General Synthesis Method 2, 410 mg (96% purity, 17% yield) 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-dioxazaborolane-4,8-dione (Intermediate 10A, 3.31 g, 96% purity, 11.8 mmol).

[0876] LC-MS (Method 9): R t = 0.72 min; MS (ESIpos): m / z = 236 [M+H] +

[0877] 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).

[0878] Intermediate 14A

[0879] (rac)-1-{3-[5-(trifluoromethyl)pyridin-2-yl]pyrazin-2-yl}ethan-1-ol

[0880]

[0881] Following General Synthesis Method 2, 736 mg (98% purity, 35% yield) 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-dioxazaborolane-4,8-dione (Intermediate 11A, 2.65 g, 8.78 mmol).

[0882] LC-MS (Method 2): R t = 1.46 min; MS (ESIpos): m / z = 270 [M+H] +

[0883] 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).

[0884] Intermediate 15A

[0885] (rac)-1-[3-(5-methoxypyridin-2-yl)pyrazin-2-yl]ethan-1-ol

[0886]

[0887] Following General Synthesis 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-dioxazaborolane-4,8-dione (Intermediate 12A, 1.50 g, 5.68 mmol).

[0888] LC-MS (Method 2): R t = 1.12 min; MS (ESIpos): m / z = 232 [M+H] +

[0889] 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).

[0890] Intermediate 16A

[0891] (rac)-2-{1-[3-(5-chloropyridin-2-yl)pyrazin-2-yl]ethyl}-1 H -isoindole-1,3(2 H )-dione

[0892]

[0893] According to General Synthesis Method 3, 458 mg (100% purity, 72% yield) of the title compound were obtained from (rac)-1-[3-(5-chloropyridin-2-yl)pyrazin-2-yl]ethan-1-ol (Intermediate 13A, 410 mg, 1.74 mmol).

[0894] LC-MS (Method 2): R t = 1.91 min; MS (ESIpos): m / z = 365 [M+H] +

[0895] 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).

[0896] Intermediate 17A

[0897] (rac)-2-[1-{3-[5-(trifluoromethyl)pyridin-2-yl]pyrazin-2-yl}ethyl]-1-[ ... H -isoindole-1,3(2 H )-dione

[0898]

[0899] Following General Synthetic Method 3, 897 mg (100% purity, 82% yield) of the title compound was obtained from (rac)-1-{3-[5-(trifluoromethyl)pyridin-2-yl]pyrazin-2-yl}ethan-1-ol (Intermediate 14A, 736 mg, 2.73 mmol).

[0900] LC-MS (Method 2): R t = 1.99 min; MS (ESIpos): m / z = 399 [M+H] + .

[0901] Intermediate 18A

[0902] (rac)-2-{1-[3-(5-methoxypyridin-2-yl)pyrazin-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione

[0903]

[0904] According to General Synthesis Method 3, 325 mg (97% purity, 88% yield) of the title compound was obtained from (rac)-1-[3-(5-methoxypyridin-2-yl)pyrazin-2-yl]ethan-1-ol (Intermediate 15A, 230 mg, 1.00 mmol).

[0905] LC-MS (Method 2): R t = 1.65 min; MS (ESIpos): m / z = 361 [M+H] +

[0906] ¹H-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).

[0907] Intermediate 19A

[0908] (rac)-1-[3-(5-chloropyridin-2-yl)pyrazin-2-yl]ethan-1-amine

[0909]

[0910] Following General Procedure 4, 285 mg (100% purity, 97% yield) of the title compound was obtained from (rac)-2-{1-[3-(5-chloropyridin-2-yl)pyrazin-2-yl]ethyl}-1-isoindole-1,3(2H)-dione (Intermediate 16A, 457 mg, 1.25 mmol).

[0911] LC-MS (Method 2): R t = 0.69 min; MS (ESIpos): m / z = 235 [M+H] +

[0912] ¹H-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).

[0913] Intermediate 20A

[0914] (rac)-1-{3-[5-(trifluoromethyl)pyridin-2-yl]pyrazin-2-yl}ethan-1-amine

[0915]

[0916] According to General Procedure 4, (rac)-2-[1-{3-[5-(trifluoromethyl)pyridin-2-yl]pyrazin-2-yl}ethyl]-1 H -isoindole-1,3(2H )-dione (Intermediate 17A, 895 mg, 2.25 mmol) to afford 600 mg (94% purity, 94% yield) of the title compound.

[0917] LC-MS (Method 2): R t = 0.83 min; MS (ESIpos): m / z = 269 [M+H] +

[0918] ¹H-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).

[0919] Intermediate 21A

[0920] (rac)-1-[3-(5-methoxypyridin-2-yl)pyrazin-2-yl]ethan-1-amine

[0921]

[0922] According to General Procedure 4, (rac)-2-[1-{3-[5-(methoxy)pyridin-2-yl]pyrazin-2-yl}ethyl]-1 H -isoindole-1,3(2 H )-dione (Intermediate 18A, 325 mg, 0.90 mmol) to afford 220 mg (60% purity, 64% yield) of the title compound.

[0923] LC-MS (Method 2): R t= 0.60 min; MS (ESIpos): m / z = 321 [M+H] + .

[0924] Intermediate 22A

[0925] (rac)-1-(3-bromopyrazin-2-yl)ethan-1-ol

[0926]

[0927] 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 hexane, 48 mL, 120 mmol) was slowly added and stirred 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 one hour. Acetaldehyde (11 mL, 190 mmol) was added dropwise, the cooling bath was removed, and the mixture was slowly warmed to room temperature. The reaction mixture was poured into water (500 mL), acidified with 1 M hydrochloric acid, and extracted with 6 portions of ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, the solvent was carefully distilled on a rotary evaporator (40° C. bath temperature, 140 mbar) and finally purified by flash chromatography on silica gel with a cyclohexane-ethyl acetate gradient to result in 12.6 g (61% of theory) of the title compound.

[0928] LC-MS (Method 2): R t = 0.81 min; MS (ESIpos): m / z = 203 [M+H] +

[0929] ¹H-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).

[0930] Intermediate 23A

[0931] (rac)-2-[1-(3-bromopyrazin-2-yl)ethyl]-1 H -isoindole-1,3(2 H )-dione

[0932]

[0933] Following General Synthesis Method 3, 12.8 g (98% purity, 77% yield) was obtained from (rac)-1-(3-bromopyrazin-2-yl)ethan-1-ol (Intermediate 22A, 10.0 g, 49.3 mmol).

[0934] LC-MS (Method 2): R t = 1.75 min; MS (ESIpos): m / z = 332 [M+H] +

[0935] ¹H-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).

[0936] Intermediate 24A

[0937] Methyl (rac)-6-{3-[-1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]pyrazin-2-yl}pyridine-3-carboxylate

[0938]

[0939] Solution A - [5-(Methoxycarbonyl)pyridin-2-yl]zinc chloride in THF: In a flame-dried 3-necked round-bottom flask, methyl 6-iodopyridine-3-carboxylate (1.88 g, 7.15 mmol) was suspended in THF (8.0 mL) and 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. Then, zinc dichloride (4.5 mL, 1.9 M in methyl-THF, 8.6 mmol) was added. This solution was then used directly in t...

Claims

1. Compounds of general formula (I) and salts thereof, in R 1 is hydrogen or optionally substituted C3-C6 cycloalkylC1-C6 alkyl, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2 and C1-C6 alkyl; R 2 is 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, -CN, -SF5; - and in each case optionally substituted C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 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 substructure S9, wherein the bond to the phenyl group or the 5- or 6-membered heteroaryl group is marked with a #; R 24 is in each case optionally substituted C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, phenyl, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 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; R 3 is a C1-C6 alkyl group; R 4 is a 5-membered heteroaryl group, wherein the 5-membered heteroaryl group contains 1 or 2 heteroatoms selected from the group consisting of N, O and S, wherein each 5-membered heteroaryl is optionally substituted with 1 substituent independently selected from the group consisting of: -halogen, -CN, -COOH; - and in each case optionally substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, -CO2C1-C6-alkyl, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 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 the following substructure S13, wherein the bond to the five-membered heteroaryl is marked with # and Z is CO: 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; R 42 is hydrogen or in each case optionally substituted C1-C6-alkyl, C1-C6-haloalkyl and C3-C6-cycloalkyl; The aforementioned R 41 、R 42 The optionally substituted groups in the definition are optionally substituted by up to 3 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 42 Together with the nitrogen atom to which they are attached, they represent a monocyclic optionally substituted 3- to 12-membered saturated heterocyclic group, It may contain up to two other heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur and silicon, which are optionally substituted with one to three substituents selected from the group consisting of: Halogen, =O (oxo), =S (thiocarbonyl), 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, C1-C4 haloalkylsulfonyl; R 5 is hydrogen or in each case optionally substituted C1-C3-alkyl, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2 and C1-C3-alkyl; R 6 is hydrogen or in each case optionally substituted C1-C3-alkyl, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2 and C1-C3-alkyl; The following compounds are excluded:

2. The compound and salt thereof according to claim 1, wherein R 1 is hydrogen; or optionally substituted C3-C6 cycloalkylC1-C6 alkyl, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2 and C1-C6 alkyl; 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, -CN, -SF5; - and in each case optionally substituted C1-C6-alkyl, C3-C6-cycloalkyl, C1-C3-haloalkyl, C1-C3-haloalkoxy, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 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 substructure S9, wherein the bond connecting the aforementioned phenyl, pyridine, pyrimidine, pyrazine, pyridazine, pyrazole, pyrrole, thiazole, oxazole or thiophene is marked with #; R 24 is in each case optionally substituted C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, phenyl; Among them in R 24 The aforementioned optionally substituted groups in the definition of are optionally substituted by up to 3 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; R 3 is a C1-C6 alkyl group; R 4 is selected from the group consisting of thiazole, pyrazole, pyrrole, oxazole, isothiazole, isoxazole, thiophene, and imidazole, each of which is optionally substituted with 1 substituent independently selected from the group consisting of: -halogen, -CN, -COOH; - and in each case optionally substituted C1-C6-alkyl, C1-C3-haloalkyl, C1-C4-alkoxy, -CO2C1-C4-alkyl, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 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 substructure S13, wherein the bond to the aforementioned thiazole, pyrazole, pyrrole, oxazole, isothiazole, isoxazole, thiophene, or imidazole is marked with # and Z is CO; 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; R 42 is hydrogen or in each case optionally substituted C1-C4-alkyl, C1-C4-haloalkyl and C3-C6-cycloalkyl; Among them in R 41 、R 42 The aforementioned optionally substituted groups in the definition of are optionally substituted by up to 3 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 42 Together with the nitrogen atom to which they are attached, they represent a monocyclic 4- to 12-membered saturated heterocyclic group which may contain up to two further heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur and silicon, and which is optionally substituted by one to three substituents selected from the group consisting of: Halogen, =O (oxo), =S (thiocarbonyl), 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, C1-C4 haloalkylsulfonyl; R 5 is hydrogen, or in each case optionally substituted C1-C3-alkyl, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2 and C1-C3-alkyl; R 6 is hydrogen, or in each case optionally substituted C1-C3-alkyl, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 substituents independently selected from the group consisting of halogen, hydroxy, -CN, -NO2, -Si(CH3)3, -NH2 and C1-C3-alkyl.

3. The compound and salt thereof according to claim 1 or 2, wherein R 1 is hydrogen; or C3-C6 cycloalkyl C1-C6 alkyl; 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 1, 2, or 3 of the optional substituents are independently selected from the group consisting of: -halogen, -CN, -SF5; - and C1-C4 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C1-C3 haloalkoxy; and - Substructure S9, in which the bond to the pyrazole, phenyl, pyridine, pyrimidine, pyrazine or pyridazine is marked with #; R 24 is in each case optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl and phenyl; Among them in R 24 The aforementioned optionally substituted groups in the definition are optionally substituted by up to 3 substituents independently selected from the group consisting of halogen, -CN, -NO2, -Si(CH3)3, C1-C3 alkyl, C1-C3 haloalkyl; R 3 is a C1-C6 alkyl group; R 4 is selected from the group consisting of pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene and imidazole, wherein each of the aforementioned 5-membered heteroaryl groups is optionally substituted with 1 substituent, wherein at each occurrence up to all of the optional substituents are independently selected from the group consisting of: -halogen, -CN, -COOH; - and C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, -CO2C1-C3 alkyl; and - Substructure S13, wherein the bond to the aforementioned pyrazole, pyrrole, thiazole, oxazole, isothiazole, isoxazole, thiophene or imidazole is marked with # and Z is CO; 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; R 42 is hydrogen or in each case optionally substituted C1-C3 alkyl, C1-C3 haloalkyl, and C3-C4 cycloalkyl; Among them, R 41 、R 42 The aforementioned optionally substituted groups defined are optionally substituted with up to 2 substituents independently selected from the group consisting of halogen, -CN, -NO2, -Si(CH3)3, C1-C3 alkyl, C1-C3 haloalkyl; or R 41 and R 42 Together with the nitrogen atom to which they are attached, they represent a monocyclic 4- to 8-membered saturated heterocyclic ring which may contain up to one further heteroatom selected from the group consisting of oxygen, nitrogen, sulfur and silicon, and which is optionally substituted by one to three substituents selected from the group consisting of: Halogen, =O (oxo), =S (thiocarbonyl), hydroxy, -CN, -NO2 and -NH2; and C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy; R 5 is hydrogen, C1-C3-alkyl; R 6 It is hydrogen, C1-C3-alkyl.

4. The compound and salt thereof according to claim 1, wherein R 1 is hydrogen; cyclopropylmethyl; R 2 Selected from the group consisting of pyrazole, phenyl, and pyridine, each of which is optionally substituted with 1 or 2 substituents independently selected from the group consisting of fluoro, chloro, bromo, iodo, -CN, -SF5, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, cyclobutyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy; R 3 is methyl, ethyl, n-propyl or isopropyl; 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, each of which is optionally substituted with 1 substituent selected from the group consisting of fluoro, chloro, bromo, -CN, -COOH, methyl, ethyl, n-propyl, isopropyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, and substructure S13, wherein the bonds binding the aforementioned 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 groups are 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, they represent pyrrolidine, piperidine, azepane, morpholine, oxazazepane, azasilacyclopentane, azasilacyclohexane, azasilacycloheptane, each of which is optionally substituted by 1 or 2 methyl groups; R 5 are hydrogen, methyl, ethyl, n-propyl, isopropyl; R 6 It is hydrogen, methyl, ethyl, n-propyl, isopropyl.

5. The compound and salt thereof according to claim 1, wherein R 1 is hydrogen or cyclopropylmethyl; R 2 Selected from the group consisting of pyrazole, phenyl, and pyridine, each of which is optionally substituted with 1 or 2 substituents independently selected from the group consisting of fluoro, chloro, bromo, iodo, -CN, -SF5, methyl, ethyl, n-propyl, isopropyl, tert-butyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, difluoromethoxy, trifluoromethoxy; R 3 It is a methyl group; R 4 is selected from the group consisting of 1,3-thiazol-2-yl and 1H-pyrazol-1-yl, each of which is optionally substituted with 1 substituent selected from the group consisting of fluoro, chloro, bromo, -CN, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, and substructure S13, wherein the bond marked with # is attached to the C-5 position of the aforementioned 1,3-thiazol-2-yl or the C-4 position of the aforementioned 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, they represent pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine, oxazepane or (Si,Si-dimethyl)azasilacyclohexane; R 5 is hydrogen or methyl; R 6 is hydrogen or methyl.

6. The compound and salt thereof according to claim 1, wherein R 2 is selected from the group consisting of phenyl, pyridyl, thiophene, pyrazole and imidazole, which may be substituted as defined in claim 1.

7. The compound and salt thereof according to claim 1, wherein R 4 Each selected from the group consisting of thiazole, pyrazole, pyrrole, oxazole, isothiazole, isoxazole, thiophene and imidazole, each of which may be substituted as defined in claim 1.

8. The compound according to claim 7, wherein R 4 Selected from the group consisting of thiazole and pyrazole, each of which may be substituted as defined in claim 7.

9. The compound according to claim 1, wherein R 2 is the substructure Q1, where the bond to the C=O- group is marked with #: in R 25 is C4-C6 alkyl, C1-C3 cyanoalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cyanocycloalkyl, C1-C3 alkylsulfonyl, C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylsulfonyl, hydroxy-C1-C4 alkyl, or benzenesulfonyl; and R 26 It is halogen, -CN, -SF5, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C3-C6 cycloalkylsulfonyl, C3-C6 cycloalkyl, C1-C3 cyanoalkyl, C3-C6 cyanocycloalkyl.

10. The compound and salt thereof according to claim 1, characterized in that Having a structure according to formula (I-vii)-(I-xix) in R 1 、R 3 、R 5 and R 6 has the meaning as defined in claim 1; R 7 are the same or different and have the same or different characteristics as those in claim 1 2 The meaning of the substituents on the defined phenyl or 5- or 6-membered heteroaryl groups; R 8 are the same or different and have the same 4 The meaning of the substituents on the defined 5-membered heteroaryl group; R 81 represents in each case optionally substituted C1-C6-alkyl, C1-C3-haloalkyl, wherein the aforementioned optionally substituted groups are optionally substituted by up to 3 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; n represents an integer of 0 or 1; m represents an integer of 1 or 2.

11. A formulation comprising at least one compound of formula (I) according to any one of claims 1 to 10, which may further comprise at least one further compound selected from the group consisting of bulking agents, surface-active substances, adjuvants, excipients, solvents and / or further pharmaceutically active agents.

12. Use of a compound of formula (I) according to any one of claims 1 to 10 or a formulation according to claim 11 for the preparation of a medicament for use as an anti-endoparasitic agent, anti-ectoparasitic agent, arthropodicide, insecticide or acaricide.

13. Use of a compound of formula (I) according to any one of claims 1 to 10 or a formulation according to claim 11 for controlling animal pests or in the field of animal health, wherein methods of treating the animal body by surgical intervention or therapeutic and diagnostic methods practiced on the animal body are excluded, or for use in crop protection or in disease vector control.

14. The use according to claim 13, wherein - The animal pest is an insect or an arachnid.

15. A method for controlling pests, characterized in that Allowing the compound of formula (I) according to any one of claims 1 to 10 or the formulation according to claim 11 to act on the pests and / or their habitat, wherein methods of treating the animal body by surgery or therapeutic and diagnostic methods practiced on the animal body are excluded; or a method for protecting seeds or germinating plants from pests, which comprises a method step in which the seeds are brought into contact with a compound of formula (I) according to any one of claims 1 to 10 or with a formulation according to claim 11.

16. The method of claim 15, wherein the pests are selected from animal pests selected from the group consisting of insects and arachnids.

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