Hydroxy-dihydropyridinone carboxamides as pesticides

Abstract

The invention relates to new hydroxy-dihydropyridinone carboxamides, to a method for the production thereof, and to the use thereof for controlling animal pests, primarily arthropods and in particular insects, arachnids and nematodes.

Description

[0001] Hydroxy-dihydropyridinone carboxamide as a pesticide

[0002] The present invention relates to novel hydroxy-dihydropyridinone carboxamides, processes for their production and their use for controlling animal pests, especially arthropods and in particular insects, arachnids and nematodes.

[0003] Certain hydroxy-dihydropyridinone carboxamides with insecticidal activity are already known (WO2021261562, WO2023127806, WO2024048778). However, the active ingredients already known according to the aforementioned publications have some disadvantages in their application, either because they have a narrow application range or because they do not exhibit satisfactory insecticidal activity.

[0004] Modern insecticides and acaricides must meet numerous requirements, such as the intensity, duration, and breadth of their effects and their potential applications. Factors such as toxicity, the impact on beneficial insects and pollinators, environmental properties, application rates, compatibility with other active ingredients or formulation aids, and the effort required for synthesis all play a role. Furthermore, resistance can develop, to name just a few parameters. For all these reasons, the search for new plant protection products cannot be considered complete, and there is a constant need for new compounds with properties that are improved compared to known compounds, at least in some aspects.

[0005] The object of the present invention was to provide compounds for use in the control of animal pests, thereby supplementing the range of pest control agents in various aspects.

[0006] It has now been surprisingly discovered that certain new hydroxy-dihydropyridinone carboxamides offer advantages over previously known compounds, such as improved biological and ecological properties, broader application methods, enhanced insecticidal and acaricidal activity, and good compatibility with crops. These new hydroxy-dihydropyridinone carboxamides can be used in combination with other agents to improve efficacy, particularly against difficult-to-control insects. The new compounds according to the invention have not previously been disclosed.

[0007] The subject of the present invention is therefore new compounds of formula (I)

[0008] wherein (design 1-1)

[0009] A for a 5- to 10-membered aromatic or heteroaromatic ring or a bicyclic ring system, each unsubstituted or substituted with 1 to 3 R A , stands; each one stands

[0010] R A independently for halogen, cyano, nitro, SF5, C(O)R a , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a , OC(O)R a , OSO2R a , or SO2NR b R c ; or for Ci-C6-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C-cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R fmay be substituted; or for phenyl or a 5- or 6-membered heteroaromatic ring, each unsubstituted or substituted with 1 to 3 R f ; or two adjacent R A together they form an unsubstituted or simple to 4-fold with halogen and / or possibly with R f substituted linear C;,-C -alkylcn groups, wherein independently one CH2 unit can be replaced by carbonyl and / or one to two CH2 units can be replaced by O or S;

[0011] X and Y can independently represent O or S;

[0012] R 1 H stands for; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C-cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f may be substituted; or for C(T)R a , C(O)OR a , C(T)NR b R c , OH, OR a , S(O) n R a or SO2NRb R c stands;

[0013] R 2 represents phenyl, naphthyl, or a 5- to 10-membered heteroaromatic ring, each either unsubstituted or substituted with 1 to 3 Rs 21 ; each one

[0014] R 21 independently for halogen, cyano, nitro, SF5, C(T)R a , C(N=OR b )R c , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a OC(O)R a , OSO2R a , or SO2NR b R c ; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f can be substituted; or two adjacent R 21 together they form an unsubstituted or simple to 4-fold halogen and / or possibly with 1 to 2 r fsubstituted linear Cs-C alkylcn groups, wherein independently one CH2 unit can be replaced by carbonyl and / or one to two CH2 units can be replaced by O or S;

[0015] R 3 stands for H; or for halogen, cyano, OH, OR. a or so) n R a stands for; or stands for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C-cycloalkyl, all of which may be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f They may be substituted;

[0016] R 4 and R 5 each independently stand for H; or for Ci-Ce-Alky 1, C2-Ce-Alkeny 1, C2-Ce-Alkynyl or Cs-C-Cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with 1 to 3 R f may be substituted; or R 4 and R 5together they form a C2-Ce alkyl chain and a 3- or 6-membered ring, which may optionally be combined with R f may be substituted and / or by O, S(O) n or NR d may be interrupted, or

[0017] R 3 and R 5 together they form a C3-C4 alkyl chain and a 5- or 6-membered ring, which may optionally be combined with R f may be substituted and / or by O, S(O) n or NR d may be interrupted;

[0018] R 6 stands for H; or for C(T)R a , C(O)OR a , C(T)NR b R c , OH, OR a or so) n R a stands for; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl or Ci-C-cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f They may be substituted;

[0019] R7 H stands for; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl or Ci-C-cycloalkyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R f may be substituted; or for C(O)R a , C(O)OR a , C(O)NR b R c , NR d R e , OR a , S(O) n R a or SO2NR b R c stands; or stands for phenyl or for a 4- to 7-membered saturated, partially saturated or aromatic heterocycle with 1 to 3 heteroatoms, each unsubstituted or substituted with 3 R f ; or represents a C2-C3 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point and which may optionally be linked to R f may be substituted and / or by O, S(O) n or NR d may be interrupted;

[0020] R 8H stands for; or for Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl or C5-C7-cycloalkenyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R. g may be substituted; or for C(O)R a , C(O)OR a , C(O)NR b R c , S(O) n R a or SO2NR b R c stands; or stands for a 4- to 7-membered saturated or partially saturated heterocycle with 1 to 3 heteroatoms, each unsubstituted or simply to 5-fold with halogen and / or with R f may be substituted; or

[0021] R 7 and R 8are linked together and form a 5- to 7-membered partially saturated heterocyclic ring with 2 to 3 heteroatoms, which may be unsubstituted or optionally substituted with C1-C4 alkyl, Cs-Ce cycloalkyl or Cs-Ce spirocycloalkyl, each of which may be unsubstituted or singly to triply substituted with halogen and / or optionally with R f can be substituted; each one is involved

[0022] T independently of each other for O or S;

[0023] R a independently of each other for Ci-Ce-alkyl, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, each of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with 1 to 3 R f They may be substituted;

[0024] R b and R cindependently of each other for H; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f ; or R b and R c together they form a ring with 3 to 7 segments;

[0025] R d and R e independently for H; or for C(T)R a , C(O)OR a or so) n R a ; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f ; or R d and R e together they form a ring with 3 to 7 segments;

[0026] R findependently for halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-Czi-alkylsulfmyl, Ci-Czi-Haloalkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Haloalkylsulfonyl, Ci-C4-Alky Icarbony 1, Ci-Czi-Alkoxy carbony 1;

[0027] R g independently of one another for halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfmyl, Ci-Czi-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, Ci-C4-alky icarbonyl, Ci-C4-alkoxy carbonyl, Ci-Czi-alky icarbonyl amino or Ci-C4-alkylamino carbonyl; or for a 4- to 7-membered saturated, partially saturated or aromatic heterocycle with 1 to 3 heteroatoms, each unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f; n independently for 0, 1 or 2.

[0028] Preferred (design 2-1) are the compounds of formula (I) in which

[0029] A for phenyl or for a heteroaromatic from the series furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, all unsubstituted or substituted with 1 to 3 R A , stands; each one stands

[0030] R A independently for halogen, cyano, nitro, SF5, C(O)R a , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a , OC(O)R a , OSO2R a , or SO2NR b R c; or for Ci-C6 alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C cycloalkyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0031] X and Y stand for O;

[0032] R 1 H stands for; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C-cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f may be substituted; or for C(T)R a , C(O)OR a or S(O)2R a stands;

[0033] R 2for phenyl or for a heteroaromatic from the series furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, all unsubstituted or substituted or substituted with 1 to 3 R 21 ; each one

[0034] R 21 independently for halogen, cyano, nitro, SF5, C(T)R a , C(N=OR b )R c , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a OC(O)R a , OSO2R a , or SO2NR b R c; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C cycloalkyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0035] R 3 H stands for; or for halogen, cyano or OH stands for; or for Ci-C4-alkyl or C2-C4-alkenyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f can be substituted; R 4 and R 5 each independently represent H; or represent Ci-C4-alkyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f may be substituted; or R 4 and R 5 together they form a C2-C6 alkyl chain and a 3- or 6-membered ring, which may optionally be combined with R f may be substituted and / or by O, S(O) nor NR d may be interrupted, 5-fold; or

[0036] R 3 and R 5 are jointly linked to form a C3-C4 alkyl chain and a 5- or 6-membered ring, which may optionally be combined with R f may be substituted and / or by O, S(O) n or NR d may be interrupted;

[0037] R 6 stands for H; or for C(T)R a , C(O)OR a or so) n R a stands; or stands for C1-C4 alkyl or C2-C6 alkenyl, each of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0038] R 7 H stands for; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkyny 1 or Cs-Cs-cycloalkyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R f may be substituted; or for C(O)Ra , C(O)OR a , C(O)NR b R c , NR d R e , OR a or so) n R a stands; or stands for a C2-C3 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point and which may optionally be linked to R f may be substituted;

[0039] R 8 H stands for; or for Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl or C5-C7-

[0040] Cycloalkenyl stands for all of which can be unsubstituted, or simply up to five times with halogen and / or possibly with R. g may be substituted; or for C(O)R a , C(O)OR a , or so) n R a stands; or for a heterocycle from the series oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl or thianyl, each unsubstituted or substituted with R f ; or

[0041] R7 and R 8 are linked together and form a 5- to 7-membered partially saturated heterocyclic ring with 2 to 3 heteroatoms, which may be unsubstituted or optionally substituted with Ci-C4 alkyl, in each case unsubstituted or singly to triplely with halogen and / or optionally with R f substituted; each one stands for

[0042] T independently for O or S; R a independently of each other for Ci-Ce-alkyl, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0043] R b and R c independently of each other for H; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f ; or R band R c together they form a ring with 3 to 6 segments;

[0044] R d and R e independently for H; or for C(T)R a , C(O)OR a ; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f ; or R d and R e together they form a ring with 3 to 5 segments;

[0045] R f independently for halogen, cyano, nitro, hydroxy; or for Ci-C4-alkyl, C;,-CT-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, Ci-C4-haloalkylsulfmyl, Ci-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, Ci-C4 alkylcarbonyl or Ci-C4 alkoxy carbonyl;

[0046] R gunabhängig voneinander für Halogen, Cyano, Nitro, Hydroxy, Ci-C4-Alkyl, Cs-Ce-Cycloalkyl, Ci-C4-Haloalkyl, Ci-C4-Alkoxy, Ci-C4-Haloalkoxy, Ci-C4-Alkylthio, Ci-C4-Haloalkylthio, Ci- C4- Alkylsulfinyl, Ci-C4-Haloalkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Haloalkylsulfonyl, Ci- C4-Alkylcarbonyl, Ci-C4-Alkoxy carbonyl, Ci-C4-Alkylcarbonylamino oder Ci-C4-Alkylamino- carbonyl;or for phenyl or for a heterocycle from the series furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, oxetanyl, Oxolanyl, Di-oxolanyl, Oxanyl, Dioxanyl, Thiethanyl, Thiolanyl, Thianyl or Morpholinyl, each unsubstituted or substituted with 1 to 3 halogens and / or optionally with R; f ; n independently for 0, 1 or 2.

[0047] Also preferred (design 2-2) are the compounds of formula (I), in which

[0048] A for phenyl or for a heteroaromatic from the series furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, all unsubstituted or substituted with 1 to 3 R A , stands; each R stands A independently for halogen, cyano, nitro, SF5, C(O)R a , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a , OC(O)R a , OSO2R a , or SO2NR b R c ; or for Ci-C6 alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C cycloalkyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R fThey may be substituted;

[0049] X and Y stand for O;

[0050] R 1 H stands for; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C-cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f may be substituted; or for C(T)R a , C(O)OR a or S(O)2R a stands;

[0051] R 2 for phenyl or for a heteroaromatic from the series furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, all unsubstituted or substituted or substituted with 1 to 3 R 21 ; each one

[0052] R21 independently for halogen, cyano, nitro, SF5, C(T)R a , C(N=OR b )R c , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a OC(O)R a , OSO2R a , or SO2NR b R c ; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C cycloalkyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0053] R 3 H stands for; or for halogen, cyano or OH stands for; or for Ci-C4-alkyl or C2-C4-alkenyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0054] R 4 and R 5each independently represent H; or represent Ci-C4-alkyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f may be substituted; or R 4 and R 5 together they form a C2-Ce alkyl chain and a 3- or 6-membered ring, which may optionally be combined with R f may be substituted and / or by O, S(O) n or NR d may be interrupted, 5-fold; or

[0055] R 3 and R 5 are jointly linked to form a C3-C4 alkyl chain and a 5- or 6-membered ring, which may optionally be combined with R f may be substituted and / or by O, S(O) n or NR d may be interrupted; R 6 stands for H; or for C(T)R a , C(O)OR a or so) n R astands; or stands for C1-C4 alkyl or C2-C6 alkenyl, each of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0056] R 7 H stands for; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkyny 1 or Cs-Cs-cycloalkyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R f may be substituted; or for C(O)R a , C(O)OR a , C(O)NR b R c , NR d R e , OR a or so) n R a stands; or stands for a C2-C3 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point and which may optionally be linked to R f may be substituted;

[0057] R 8H stands for; or for Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl or C5-C7-cycloalkenyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R. g may be substituted; or for C(O)R a , C(O)OR a , or so) n R a stands; or for a heterocycle from the series oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiethanyl-l-oxide, thiethanyl-l,l-dioxide, thiolanyl, thiany 1, thianyl-l-oxide or thiany 1-1,1-dioxide, all of which are unsubstituted or substituted with R f ; or

[0058] R 7 and R 8are linked together and form a 5- to 7-membered partially saturated heterocyclic ring with 2 to 3 heteroatoms, which may be unsubstituted or optionally substituted with Ci-C4 alkyl, in each case unsubstituted or singly to triplely with halogen and / or optionally with R f substituted; each one stands for

[0059] T independently of each other for O or S;

[0060] R a independently of each other for Ci-Ce-alkyl, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, each of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0061] R b and R c independently of each other for H; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f ; or R b and Rc together they form a ring with 3 to 6 segments; R d and R e independently for H; or for C(T)R a , C(O)OR a ; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f ; or R d and R e together they form a ring with 3 to 5 segments;

[0062] R f independently for halogen, cyano, nitro, hydroxy; or for Ci-C4-alkyl, CT-CT-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, Ci-C4-haloalkylsulfmyl, Ci-C4-alkylsulfonyl, C1-C4 haloalkylsulfonyl, Ci-C4 alkylcarbonyl or Ci-C4 alkoxy carbonyl;

[0063] R gunabhängig voneinander für Halogen, Cyano, Nitro, Hydroxy, Ci-C4-Alkyl, Cs-Ce-Cycloalkyl, Ci-C4-Haloalkyl, Ci-C4-Alkoxy, Ci-C4-Haloalkoxy, Ci-C4-Alkylthio, Ci-C4-Haloalkylthio, Ci- C4- Alkylsulfinyl, Ci-C4-Haloalkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Haloalkylsulfonyl, Ci- C4-Alkylcarbonyl, Ci-C4-Alkoxy carbonyl, Ci-C4-Alkylcarbonylamino oder Ci-C4-Alkylamino- carbonyl;or for phenyl or for a heterocycle from the series furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, oxetanyl, Oxolanyl, Di-oxolanyl, Oxanyl, Dioxanyl, Thiethanyl, Thiolanyl, Thianyl or Morpholinyl, each unsubstituted or substituted with 1 to 3 halogens and / or optionally with R; f ; n independently for 0, 1 or 2.

[0064] Further preferred (design 3-1) are the compounds of formula (I), in which

[0065] A for phenyl or for a heteroaromatic from the series furanyl, thienyl, pyrazolyl, thiazolyl, pyridyl, pyrimidyl, pyridazinyl or pyrazinyl, all unsubstituted or substituted with 1 to 3 R A , stands; each one stands

[0066] R A independently for halogen, cyano, C(O)R a , C(O)OR a , C(O)NR b R c , OR a , S(O) n R a , OSO2R a , or SO2NR b R c ; or for C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl or Cs-Ce cycloalkyl, each of which may be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0067] X and Y stand for O;

[0068] R 1H stands for; or for Ci-C4-alkyl, C2-C4-alkenyl or C2-C4-alkynyl, all of which can be unsubstituted, or simply up to 3 times with halogen and / or optionally with R. f may be substituted; or for C(O)R a , C(O)OR a or S(O)2R a stands; R 2 for phenyl or for a heteroaromatic from the series thienyl, pyrazolyl, oxazolyl, thiazolyl, pyridyl, pyrimidyl, pyridazinyl or pyrazinyl, all unsubstituted or substituted or substituted with 1 to 3 R 21 ; each one

[0069] R 21 independently for halogen, cyano, nitro, C(O)R a , C(N=OR b )R c , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a OC(O)R a or SO2NR b R c; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C-Cr cycloalkyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0070] R 3 stands for H or for Ci-C4-alkyl;

[0071] R 4 and R 5 each independently stand for H or for Ci-C4 alkyl; or

[0072] R 3 and R 5 together they form a C3-C4 alkyl chain and a 5- or 6-membered ring;

[0073] R 6 stands for H; or for C(O)R a , C(O)OR a or so) n R a stands for; or stands for C1-C4 alkyl;

[0074] R 7H stands for; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkyny 1 or Cs-Cs-cycloalkyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R f may be substituted; or for C(O)R a , C(O)OR a , C(O)NR b R c , NR d R e , OR a or so) n R a stands; or stands for a C2-C3 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point;

[0075] R 8 H stands for; or for Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C5-C7-cycloalkenyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R. g may be substituted; or for C(O)R a , C(O)OR a , or so) n R astands for; or stands for a heterocycle from the series oxetanyl, oxolanyl or oxanyl; or

[0076] R 7 and R 8 are connected to each other and form a 5- to 6-membered partially saturated heterocyclic ring; each

[0077] T independently for O or S; R a independently of each other for C1-C4 alkyl, Cs-Ce-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, each of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0078] R b and R c independently for H; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with 1 to 2 R f ; or R b and R c together they form a ring with 3 to 6 segments;

[0079] R dand R e independently for H; or for C(T)R a , C(O)OR a ; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with 1 to 2 R f ; or R d and R e together they form a ring with 3 to 5 segments;

[0080] R f independently for halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfmyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, Ci-C4-alkylcarbonyl or Ci-C4-alkoxy carbonyl;

[0081] R gindependently of one another for halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfmyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, Ci-C4-alkylcarbonyl, Ci-C4-alkoxy carbonyl, Ci-C4-alkylcarbonylamino or Ci-C4-alkylamino-carbonyl; or for a heterocycle from the series oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl or morpholinyl, each unsubstituted or substituted with 1 to 3 halogens and / or optionally with R f ; n independently for 0, 1 or 2.

[0082] Also still preferred (design 3-2) are the compounds of formula (I), in which

[0083] A for phenyl or for a heteroaromatic from the series furanyl, thienyl, pyrazolyl, thiazolyl, pyridyl, pyrimidyl, pyridazinyl or pyrazinyl, all unsubstituted or substituted with 1 to 3 R A , stands; each one stands

[0084] R A independently for halogen, cyano, C(O)R a , C(O)OR a , C(O)NR b R c , OR a , S(O) n R a , OSO2R a , or SO2NR b R c ; or for C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl or Cs-Ce cycloalkyl, each of which may be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They can be substituted; X and Y stand for O;

[0085] R 1 H stands for; or for Ci-C4-alkyl, C2-C4-alkenyl or C2-C4-alkynyl, all of which can be unsubstituted, or simply up to 3 times with halogen and / or optionally with R. fmay be substituted; or for C(O)R a , C(O)OR a or S(O)2R a stands;

[0086] R 2 for phenyl or for a heteroaromatic from the series thienyl, pyrazolyl, oxazolyl, thiazolyl, pyridyl, pyrimidyl, pyridazinyl or pyrazinyl, all unsubstituted or substituted or substituted with 1 to 3 R 21 ; each one

[0087] R 21 independently for halogen, cyano, nitro, C(O)R a , C(N=OR b )R c , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a OC(O)R a or SO2NR b R c ; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C4-cycloalkyl, each of which may be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0088] R 3stands for H or for Ci-C4-alkyl;

[0089] R 4 and R 5 each independently stand for H or for Ci-C4 alkyl; or

[0090] R 3 and R 5 together they form a C3-C4 alkyl chain and a 5- or 6-membered ring;

[0091] R 6 stands for H; or for C(O)R a , C(O)OR a or so) n R a stands for; or stands for C1-C4 alkyl;

[0092] R 7 H stands for; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkyny 1 or Cs-Cs-cycloalkyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R f may be substituted; or for C(O)R a , C(O)OR a , C(O)NR b R c , NR d R e , OR a or so) n R astands; or stands for a C2-C3 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point;

[0093] R 8 H stands for; or for Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C5-C7-cycloalkenyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R. g may be substituted; or for C(O)R a , C(O)OR a , or so) n R a stands for; or stands for a heterocycle from the series oxetanyl, oxolanyl, oxanyl, thietanyl, thietanyl-1-oxide, thietanyl-1,1-dioxide, thianyl, thianyl-1-oxide or thiany-1-1,1-dioxide; or R 7 and R 8 are connected to each other and form a 5- to 6-membered partially saturated heterocyclic ring; each

[0094] T independently of each other for O or S;

[0095] R aindependently of each other for C1-C4 alkyl, Cs-Ce-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, each of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted;

[0096] R b and R c independently for H; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with 1 to 2 R f ; or R b and R c together they form a ring with 3 to 6 segments;

[0097] R d and R e independently for H; or for C(T)R a , C(O)OR a ; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with 1 to 2 R f ; or R d and R ebilden zusammen einen 3- bis 5-gliedrigen Ring;

[0098] R f unabhängig voneinander für Halogen, Cyano, Nitro, Hydroxy, Ci-C4-Alkyl, Cs-Ce-Cycloalkyl, Ci-C4-Haloalkyl, Ci-C4-Alkoxy, Ci-C4-Haloalkoxy, Ci-C4-Alkylthio, Ci-C4-Haloalkylthio, Ci- C4- Alkylsulfinyl, Ci-C4-Haloalkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Haloalkylsulfonyl, Ci- C4-Alkylcarbonyl oder Ci-C4-Alkoxy carbonyl;

[0099] R gindependently of one another for halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfmyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, Ci-C4-alkylcarbonyl, Ci-C4-alkoxy carbonyl, Ci-C4-alkylcarbonylamino or Ci-C4-alkylamino-carbonyl; or for a heterocycle from the series oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl or morpholinyl, each unsubstituted or substituted with 1 to 3 halogens and / or optionally with R f ; n independently for 0, 1 or 2.

[0100] Particularly preferred (design 4-1) are the compounds of formula (I) in which

[0101] A for phenyl or for a heteroaromatic from the series thienyl, pyrazolyl, thiazolyl, pyridyl, pyrimidyl, pyridazinyl or pyrazinyl, each unsubstituted or substituted with 1 to 3 RA , stands; each R stands A independently for halogen, cyano, OR a ; or for Ci-C4-alkyl, each unsubstituted or simply to 3-fold substituted with halogen;

[0102] X and Y stand for O;

[0103] R 1 stands for H; or for Ci-C4-alkyl; or for C(O)R a , C(O)OR a or S(O)2R a stands;

[0104] R 2 for phenyl thienyl, pyrazolyl, thiazolyl or pyridyl, all unsubstituted or substituted or substituted with 1 to 3 R 21 ; each one

[0105] R 21 independently for halogen, cyano, nitro, OR a , S(O) n R a or SO2NR b R c; or for Ci-C4-alkyl, either unsubstituted or simply to 5-fold substituted with fluorine or chlorine; or for cyclopropyl, unsubstituted or simply to 3-fold substituted with fluorine or chlorine or substituted with cyano;

[0106] R 3 H stands for;

[0107] R 4 and R 5 each stand independently for H;

[0108] R 6 stands for H; or for C(O)R a or C(O)OR a stands for; or stands for methyl or ethyl;

[0109] R 7 stands for H; or for Ci-C4-alkyl or QC-cycloalkyl; or for C(O)R a , C(O)OR a ,

[0110] C(O)NR b R c , NR d R e , OR a or so) n R a stands; or stands for a C2-C3 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point;

[0111] R 8H stands for; or for Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C5-C7-cycloalkenyl, all of which can be unsubstituted, or simply to fivefold with fluorine or chlorine and / or optionally with R g may be substituted; or for C(O)R a , C(O)OR a , or so) n R a stands; or for a heterocycle from the series oxolanyl or oxanyl, stands; or or R 8 stands together with R 7 for one of the leftovers where * represents the connection point to O and # represents the connection point to C; where each R a independently of each other for Ci-C4-alkyl or Cs-Ce-cycloalkyl, each unsubstituted or 1-fold to 5-fold substituted with fluorine or chlorine;

[0112] R b and R c independently for H; or for Ci-C4-alkyl, or Cs-Ce-cycloalkyl;

[0113] R d and R eindependently for H; or for Ci-C4-alkyl or Cs-Ce-cycloalkyl;

[0114] R g independently for halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, Ci-C4-alkylcarbonyl, Ci-C4-alkoxy carbonyl, Ci-C4-alkylcarbonylamino or Ci-C4-alkylamino-carbonyl; or for a heterocycle from the series oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl or morpholinyl; n independently for 0, 1 or 2.

[0115] Also particularly preferred (design 4-2) are the compounds of formula (I), in which

[0116] A for phenyl or for a heteroaromatic from the series thienyl, pyrazolyl, thiazolyl, pyridyl, pyrimidyl, pyridazinyl or pyrazinyl, each unsubstituted or substituted with 1 to 3 R A , stands; each one stands

[0117] R A independently for halogen, cyano, OR a ; or for Ci-C4-alkyl, each unsubstituted or simply to 3-fold substituted with halogen;

[0118] X and Y stand for O;

[0119] R 1 stands for H; or for Ci-C4-alkyl; or for C(O)R a , C(O)OR a or S(O)2R a stands;

[0120] R 2 for phenyl thienyl, pyrazolyl, thiazolyl or pyridyl, all unsubstituted or substituted or substituted with 1 to 3 R 21 ; each one

[0121] R 21 independently for halogen, cyano, nitro, OR a , S(O) n R a or SO2NRb R c ; or for Ci-C4-alkyl, either unsubstituted or simply to 5-fold substituted with fluorine or chlorine; or for cyclopropyl, unsubstituted or simply to 3-fold substituted with fluorine or chlorine or substituted with cyano;

[0122] R 3 H stands for;

[0123] R 4 and R 5 each stand independently for H;

[0124] R 6 stands for H; or for C(O)R a or C(O)OR a stands for; or stands for methyl or ethyl; R 7 H stands for; or for Ci-C4-alkyl or C,-Cs-cycloalkyl stands for; or for C(O)R a , C(O)OR a , C(O)NR b R c , NR d R e , OR a or so) n R a stands; or stands for a C2-C3 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point;

[0125] R 8H stands for; or for Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C5-C7-cycloalkenyl, all of which can be unsubstituted, or simply to fivefold with fluorine or chlorine and / or optionally with R g may be substituted; or for C(O)R a , C(O)OR a , or so) n R a stands for; or stands for a heterocycle from the series oxolanyl, oxanyl, thietanyl, thietanyl-1-oxide, thietanyl-1,1-dioxide, thianyl, thianyl-1-oxide or thiany-1-1,1-dioxide; or or R 8 stands together with R 7 for one of the leftovers where * represents the connection point to O and # represents the connection point to C; where each

[0126] R a independently of each other for Ci-C4-alkyl or C;,-C,-Cvcloalkvl, each unsubstituted or 1-fold to 5-fold substituted with fluorine or chlorine;

[0127] R b and R cindependently for H; or for Ci-C4-alkyl, or Cs-Ce-cycloalkyl;

[0128] R d and R e independently for H; or for Ci-C4-alkyl or Cs-Ce-cycloalkyl;

[0129] R g independently for halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfmyl, Ci-Czi-haloalkylsulfmyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, Ci-C4-alkylcarbonyl, Ci-C4-alkoxy carbonyl, Ci-C4-alkylcarbonylamino, or Ci-C4-alkylamino-carbonyl; or for a heterocycle from the series oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, or morpholinyl; n independently for 0, 1, or 2.

[0130] Particularly preferred (design 5-1) are the compounds of formula (I) in which

[0131] A for phenyl, pyridyl, pyrimidyl, pyrazinyl or thiazolyl, each unsubstituted or substituted with 1 to 3 R A , stands; each R stands A independently for fluorine, chlorine, bromine, cyano, methyl or methoxy;

[0132] X and Y stand for O;

[0133] R 1 stands for H; or for methyl or ethyl; or for C(O)R a or C(O)OR a stands;

[0134] R 2 For phenyl, thienyl or pyridyl, unsubstituted or substituted is indicated by 1 to 3 Rs. 21 ; each one

[0135] R 21 independently for fluorine, chlorine, bromine, cyano, methyl, methoxy, CF3, CHF2, OCF3, OCHF2, SCF3, S(O)CF3, SO2CF3, cyclopropyl, 1-cyanocyclopropyl, 4-fluorophenyl, 6-fluoropyrid-3-yl;

[0136] R 3 H stands for;

[0137] R 4 and R 5 stand for H;

[0138] R 6 H stands for;

[0139] R 7 for H; or for methyl, ethyl, n-propyl, i-propyl or c-propyl, C(O)NHCH3, OCH3, C(O)CH3, C(O)OCH3 or NH2; or for a CT-alkyl chain that is linked to A via a carbon atom adjacent to the attachment point;

[0140] R 8 H stands for; or for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, propenyl or propynyl, all of which can be unsubstituted, or optionally with R. g may be substituted; or for C(O)R a , C(O)OR a , or S(O)2R a stands for; or stands for oxanyl; or R 8 stands together with R 7 for one of the leftovers where * represents the connection point to O and # represents the connection point to C; where each

[0141] R aindependently of each other for methyl, ethyl, n-propyl, i-propyl, c-propyl or c-butyl, each unsubstituted or substituted with 1-5 fluorine;

[0142] R g independently of one another for methyl, ethyl, methoxy, ethoxy, c-propyl, c-butyl, cyano, C(O)NHCH3, C(O)CH3, C(O)-c-butyl, C(O)-c-propyl, C(O)CH2-c-propyl, C(O)-i-propyl, C(O)OCH3, C(O)OCH2CH3, SO2CH3; or for one of the heterocycles oxolanyl or oxanyl. Also particularly preferred (elaboration 5-2) are the compounds of formula (I) in which

[0143] A for phenyl, pyridyl, pyrimidyl, pyrazinyl or thiazolyl, each unsubstituted or substituted with 1 to 3 R A , stands; each one stands

[0144] R A independently for fluorine, chlorine, bromine, cyano, methyl or methoxy;

[0145] X and Y stand for O;

[0146] R 1 stands for H; or for methyl or ethyl; or for C(O)R a or C(O)ORa stands;

[0147] R 2 For phenyl, thienyl or pyridyl, unsubstituted or substituted is indicated by 1 to 3 Rs. 21 ; each one

[0148] R 21 independently for fluorine, chlorine, bromine, cyano, methyl, methoxy, CF3, CHF2,

[0149] OCF3, OCHF2, SCF3, S(O)CF3, SO2CF3, cyclopropyl, 1-cyanocyclopropyl;

[0150] R 3 H stands for;

[0151] R 4 and R 5 stand for H;

[0152] R 6 H stands for;

[0153] R 7 for H; or for methyl, ethyl, n-propyl, i-propyl or c-propyl, C(O)NHCH3, OCH3, C(O)CH3, C(O)OCH3 or NH2; or for a C2 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point;

[0154] R 8H stands for; or for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, propenyl or propynyl, all of which can be unsubstituted, or optionally with R. g may be substituted; or for C(O)R a , C(O)OR a , or S(O)2R a stands for; or stands for oxanyl, thietanyl-1,1-dioxide or thianyl-1,1-dioxide; or R 8 stands together with R 7 for one of the leftovers where * represents the connection point to O and # represents the connection point to C; where each

[0155] R a independently of each other for methyl, ethyl, n-propyl, i-propyl, c-propyl or c-butyl, each unsubstituted or substituted with 1-5 fluorine; R gindependently of each other for methyl, ethyl, methoxy, ethoxy, c-propyl, c-butyl, cyano, C(O)NHCH3, C(O)CH3, C(O)-c-butyl, C(O)-c-propyl, C(O)CH2-c-propyl, C(O)-i-propyl, C(O)OCH3, C(O)OCH2CH3, SO2CH3; or for one of the heterocycles oxolanyl or oxanyl.

[0156] Highlighted (design 6-1) are the connections of formula (I) in which

[0157] A represents one of the following residues Q1 to Q7. each unsubstituted or substituted with 1 to 2 R A , where * represents the connection point to N and # represents the connection point to C, and where each

[0158] R A independently stands for fluorine, chlorine, cyano or methoxy;

[0159] X and Y stand for O;

[0160] R 1 H stands for; or for Methyl, C(O)CH3, C(O)CH2CH3, C(O)OCH3, C(O)OEt, C(O)On-Propyl, C(O)Oc-Propyl, C(O)c-Propyl or C(O)Oi-Propyl; each substituted with 1 to 2 R21 ; where # represents the connection point to C; and where each

[0161] R 21 independently of each other for fluorine, chlorine, bromine, cyano, CF3, CHF2, OCF3, OCHF2, SCF3, SO2CF3; R 3 H stands for;

[0162] R 4 and R 5 stand for H;

[0163] R 6 H stands for;

[0164] R 7 for H; or for methyl, ethyl, n-propyl, i-propyl or c-propyl, C(O)NHCH3, OCH3, C(O)CH3, C(O)OCH3 or NH2; or for CH2CH2, which is bonded to Ql via a carbon atom adjacent to the point of attachment;

[0165] R 8for H; or for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, CH2-c-propyl, propynyl, CH2C(O)NHCH3, C(O)CH3, C(O)CH2CH3, C(O)-c-butyl, C(O)-c-propyl, C(O)CH2-c-propyl, C(O)-i-propyl, C(O)OCH2CH3, CH2CN, CH2CH2CN, CH2CH2CH2CN, SO2CH3, CH2CH2SO2CH3, CH2CH=CH2, CH2CH2OCH3, CHZCCH, CH(CH3)-c-propyl or CH(CH3)C(O)OCH3; or

[0166] R 8 represents one of the remains Here, * represents the connection point to O or is used together with R. 7 for one of the leftovers Here, * represents the connection point to O and # represents the connection point to C.

[0167] Also highlighted (design 6-2) are the connections of formula (I), in which

[0168] A represents one of the following residues Q1 to Q7.

[0169]

[0170] Q-5 Q-6 Q-7 each unsubstituted or substituted with 1 to 2 R A, where * represents the connection point to N and # represents the connection point to C, and where each

[0171] R A independently stands for fluorine, chlorine, cyano or methoxy;

[0172] X and Y stand for O;

[0173] R 1 H stands for; or for Methyl, C(O)CH3, C(O)Et, C(O)OCH3, C(O)OCH2CH3, C(O)On-Propyl,

[0174] C(O)Oc-Pr, C(O)c-Propyl or C(O)Oi-Propyl stands for;

[0175] R 2 one of the remnants U-1 - U-4 stands

[0176] U-1 U-2 U-3 U-4 each substituted with 1 to 3 R 21 ; where # represents the connection point to C; and where each

[0177] R 21 independently of each other for fluorine, chlorine, bromine, cyano, CF3, CHF2, OCF3, OCHF2, SCF3, SO2CF3;

[0178] R 3 H stands for;

[0179] R 4 and R 5 stand for H;

[0180] R 6 H stands for; R 7 for H; or for methyl, ethyl, n-propyl, i-propyl or c-propyl, C(O)NHCH3, OCH3, C(O)CH3, C(O)OCH3 or NH2; or for CH2CH2, which is bonded to Ql via a carbon atom adjacent to the point of attachment;

[0181] R 8 for H; or for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, CH2-c-propyl, propynyl, CH2C(O)NHCH3, C(O)CH3, C(O)CH2CH3, C(O)-c-butyl, C(O)-c-propyl, C(O)CH2-c-propyl, C(O)-i-propyl, C(O)OCH2CH3, CH2CN, CH2CH2CN, CH2CH2CH2CN, SO2CH3, CH2SO2CH3, CH2CH2SO2CH3, CH2CH2CH2SO2CH3, CH2CH=CH2, CH2CH2OCH3, CHzCCH, CH(CH3)-c-propyl or CH(CH3)C(O)OCH3; or

[0182] R 8 represents one of the remains where * represents the point of connection to O or

[0183] R 8 stands together with R 7 for one of the leftovers Here, * represents the connection point to O and # represents the connection point to C.

[0184] In a further preferred embodiment, the invention relates to compounds of the general formula (I- 1) in which the structural elements A, R 1 , R 2 , R 7 and R 8 the meanings indicated in design (1-1) or design (2-1) or design (2-2) or design (3-1) or design (3-2) or design (4-1) or design (4-2) or design (5-1) or design (5-2) or design (6-1) or design (6-2).

[0185] In a further preferred embodiment, the invention relates to compounds of the general formula (1-2) in which the structural elements R A , R 1 , R 2 , R 7 and R 8the meanings indicated in design (1-1) or in design (2-1) or in design (2-2) or in design (3-1) or in design (3-2) or in design (4-1) or in design (4-2) or in design (5-1) or in design (5-2) or in design (6-1) or in design (6-2) have and Q 1 and Q 2 Each can stand independently for N or CH.

[0186] In a further preferred embodiment, the invention relates to compounds of the general formula (1-3) in which the structural elements R A , R 1 , R 2 , R 6 , R 7 and R 8the meanings indicated in design (1-1), or in design (2-1), or in design (2-2), or in design (3-1), or in design (3-2), or in design (4-1), or in design (4-2), or in design (5-1), or in design (5-2), or in design (6-1), or in design (6-2) have and Q 1 and Q 2 Each isome can stand independently for N or CH.

[0187] Depending on the type of substituents, the compounds of formula (I) can exist as geometric and / or optically active isomers or corresponding mixtures of isomers in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers, or geometric isomers. The invention thus encompasses both pure stereoisomers and any mixtures of these isomers.

[0188] Preferably, however, the optically active, stereoisomeric forms of the compounds of formula (I) and their salts are used according to the invention.

[0189] The invention therefore relates to both the pure enantiomers and diastereomers, as well as their mixtures for combating animal pests, which include arthropods and in particular insects.

[0190] The compounds of formula (I) may optionally exist in various polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.

[0191] Unless otherwise defined elsewhere, the term "alkyl," either alone or in combination with other terms such as haloalkyl, is understood within the scope of the present invention to mean a residue of a saturated, aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may be branched or unbranched. Examples of C1-C12 alkyl residues are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, see α-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, and n-dodecyl. Of these alkyl groups, Ci-Ce alkyl groups are particularly preferred. Ci-C4 alkyl groups are especially preferred.

[0192] Unless otherwise defined elsewhere, the term "alkenyl," either alone or in combination with other terms, is understood according to the invention to mean a linear or branched C2-Ci2-alkenyl group having at least one double bond, for example vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, and 1,4-hexadienyl. C2-C6 alkenyl groups are preferred, and C2-C4 alkenyl groups are particularly preferred.

[0193] Unless otherwise defined elsewhere, the term "alkynyl," either alone or in combination with other terms, is understood according to the invention to mean a linear or branched C2-Ci2-alkynyl residue containing at least one triple bond, for example, ethynyl, 1-propynyl, and propargyl. Of these, C'a-Ce-alkynyl is preferred, and CAC1-alkynyl is particularly preferred. The alkynyl residue may also contain at least one double bond.

[0194] Unless otherwise defined elsewhere, the term "cycloalkyl," either alone or in combination with other terms, is understood according to the invention to mean a Cs-Cs cycloalkyl group, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Cs-Ce cycloalkyl groups are preferred.

[0195] Unless otherwise defined elsewhere, the term "aryl" shall, according to the invention, be understood to mean an aromatic residue with 6 to 14 carbon atoms, preferably phenyl, naphthyl, anthryl or phenanthrenyl, particularly preferably phenyl.

[0196] Unless otherwise defined elsewhere, the term "arylalkyl" means a combination of "aryl" and "alkyl" groups as defined by invention, wherein the group is generally bonded via the alkyl group, examples of which are benzyl, phenylethyl or α-methylbenzyl, with benzyl being particularly preferred.

[0197] Unless otherwise defined elsewhere, ‘hetaryl’ means a mono-, bi- or tricyclic heterocyclic group consisting of carbon atoms and at least one heteroatom, where at least one cycle is aromatic.Bevorzugt enthält die Hetaryl-Gruppe 3, 4, 5 oder 6 C-Atome ausgewählt aus der Reihe Furyl, Thienyl, Pyrrolyl, Pyrazolyl, Imidazolyl, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, 1,2,3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,3,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,2,3-Thiadiazolyl, 1,2,4-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, Pyridyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, 1,2,3-Triazinyl, 1,2,4-Triazinyl, 1,3,5-Triazinyl, Benzofuranyl, Benzisofuryl, Benzothienyl, Benzisothienyl, Indolyl, Isoindolyl, Indazolyl, Benzothiazolyl, Benzisothiazolyl, Benzo- xazolyl, Benzisoxazolyl, Benzimidazolyl, 2,1,3-Benzoxadiazole, Chinolinyl, Isochinolinyl, Cinnolinyl, Phthalazinyl, Chinazolinyl, Chinoxalinyl, Naphthyridinyl, Benzotriazinyl, Purinyl, Pteridinyl und Indo- lizinyl.Unless otherwise defined elsewhere, "heterocyclyl" means a monocyclic, saturated or partially saturated 4-, 5-, 6-, or 7-membered ring consisting of carbon atoms and at least one heteroatom in the ring. Preferably, the heterocyclyl group contains 3, 4, 5, or 6 carbon atoms and 1 or 2 heteroatoms from the series oxygen, sulfur, or nitrogen. Examples of heterocyclyl are azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, and tetrahydrofuryl.

[0198] Unless otherwise defined elsewhere, "oxo-heterocyclyl" and "dioxo-heterocyclyl" mean a heterocyclyl compound containing a ring atom substituted with one or two (=0) groups, respectively, at least at one position in the ring. Preferably, a heteroatom such as sulfur is substituted with one or two (=0) groups, resulting in the group -S(=0)- or -S(=0)2-, where the sulfur atom is part of the ring.

[0199] Within the scope of the present invention, halogen-substituted residues, for example "halogenalkyl", are understood to be residues halogenated singly or multiply up to the maximum possible number of substituents. In the case of multiple halogenation, the halogen atoms can be the same or different. "Halogen" here refers to fluorine, chlorine, bromine, or iodine, preferably fluorine or chlorine.

[0200] The term "alkoxy", either on its own or in combination with other terms such as haloalkoxy, refers here to an O-alkyl residue, with the term "alkyl" having the meaning given above.

[0201] Explanation of the processes and intermediate products

[0202] Procedure A

[0203] A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8They have the meanings described above. PG stands for an amino protecting group, such as the Boc group; L stands for CI, Br, or I; Alk stands for a Ci-C4 alkyl group; Z stands for O, S, or HN(R). b )(R c ). Thus, the general formula (1a) corresponds to the general formula (1) with X= O and Y=O.

[0204] Stage a)

[0205] Compounds of general formula (4) can consist of aldehydes (R 7= H) or ketones of general formula (3) and hydroxylamine or hydroxylamine hydrochloride, where PG represents a protecting group, such as the Boc group. The reaction takes place in a conventional inert solvent suitable under the prevailing reaction conditions, such as ethanol or methanol, and optionally in the presence of a base, such as pyridine or triethylamine. The compounds of formula (3) are either commercially available or can be prepared by known methods, for example, analogous to the procedure described in Europ. J. Med. Chem. 2002, 243, Art. No. 114706.

[0206] Level b)

[0207] Compounds of general formula (6) can be prepared from compounds of general formula (4) and an alkylating agent of formula (5), where L represents a halogen, such as Cl or Br. The reaction is carried out in a conventional inert solvent suitable under the prevailing reaction conditions, such as acetonitrile, THF, or dimethylformamide, and optionally in the presence of a base, such as cesium carbonate or potassium carbonate.

[0208] The compounds of formula (5) are either commercially available or can be prepared by generally known methods.

[0209] Level c)

[0210] Compounds of general formula (2) can be obtained from compounds of general formula (6) and an acid such as trifluoroacetic acid. The reaction takes place in a typical inert solvent suitable under the prevailing reaction conditions, such as dichloromethane.

[0211] Stage d)

[0212] Compounds of general formula (2) can be obtained from carbonyl compounds of general formula (7) and a substituted hydroxylamine or hydroxylamine hydrochloride of formula (8). The reaction takes place in the presence or absence of a suitable inert solvent under the prevailing reaction conditions. If necessary, a base, such as pyridine or potassium carbonate, can be added, or the reaction can be carried out in a basic solvent, such as pyridine.

[0213] The compounds of formula (7) are either commercially available or can be prepared by known methods, for example analogous to the methods described in W0200860907 or US200727184.

[0214] The compounds of formula (8) are either commercially available or can be prepared by known methods, for example analogous to the methods described in US7030119.

[0215] Stage e)

[0216] Compounds of general formula (10) can be obtained from carbonyl compounds of general formula (9) and a substituted hydroxylamine or hydroxylamine hydrochloride of formula (8). The reaction takes place in the presence or absence of a suitable inert solvent under the prevailing reaction conditions. If necessary, a base, such as pyridine or potassium carbonate, can be added, or the reaction can be carried out in a basic solvent, such as pyridine.

[0217] The compounds of formula (9) are either commercially available or can be prepared by known methods, for example analogous to the procedures described in W020047491.

[0218] Level f)

[0219] Compounds of general formula (2a) can be obtained from nitro compounds of general formula (10) and a conventional reducing agent, such as iron in the presence of hydrochloric acid or hydrogen in the presence of a catalyst, such as palladium on carbon. The reaction takes place in a conventional inert solvent suitable under the prevailing reaction conditions, such as ethanol or methanol.

[0220] Level g)

[0221] Compounds of general formula (11) can be obtained from nitro compounds of general formula (9) and a substituted hydroxylamine or hydroxylamine hydrochloride of formula (8). The reaction takes place in the presence or absence of a suitable inert solvent under the prevailing reaction conditions. If necessary, a base, such as pyridine or potassium carbonate, can be added, or the reaction can be carried out in a basic solvent, such as pyridine.

[0222] Level h)

[0223] Compounds of general formula (12) can be obtained by analogy to Bioorg. Med. Chem. Lett. 2013, 23, 6629-6635 from oximes of general formula (11) and a chlorinating agent, such as N-chlorosuccinimide. The reaction takes place in the presence of a common inert solvent suitable for the prevailing reaction conditions, such as dimethylformamide.

[0224] Stage i)

[0225] Compounds of general formula (10a) can be obtained by analogy to J. Am. Chem. Soc. 2018, 140, 11202-11205 from compounds of general formula (12) and an alcohol, a thio compound, or an amine of formula (13). The reaction is carried out in the presence of a common inert solvent suitable under the prevailing reaction conditions, such as tetrahydrofuran. If necessary, a base, such as pyridine, triethylamine, or potassium carbonate, can be added. The compounds of formula (13) are commercially available.

[0226] Level j)

[0227] Compounds of general formula (1a) can be obtained analogously to WO2021261562 from ester compounds of general formula (1) and an amino compound of formula (2). The reaction takes place in the presence of a suitable inert solvent under the prevailing reaction conditions, such as toluene.

[0228] The compounds of formula (1) can be prepared by known methods, for example analogous to the methods described in WO2021261562, WO2023127806, W02007041362 or Heterocycles (1989), 28(2), 1015-35.

[0229] Procedure B

[0230] A, R a , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 have the meanings described above. R la stands for C(O)R a , C(O)OR a or R a L stands for CI, Br, or I. The general formula (Ib) corresponds to the general formula I with R. 1= H and the general formula (Ic) of the general formula (I) with R 1 = C(O)R a , C(O)OR a or R a where X and Y each represent O.

[0231] Compounds of general formula (Ic) can be obtained from compounds of general formula (Ib) and an alkylating or acylating reagent of formulas (14), (15), or (16). The reaction is carried out in the presence of a suitable inert solvent under the prevailing reaction conditions, such as dichloromethane or acetonitrile. If necessary, a base, such as pyridine or triethylamine, may be added. The compounds of formula (Ib) can be obtained according to the methods given in Procedure A for compounds of formula (1a).

[0232] The compounds of formula (14), (15) and (16) are commercially available.

[0233] Procedure C

[0234] A, R a , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8have the meanings described above. L stands for CI, Br, or I. The general formula (Id) corresponds to the general formula I with R. 8 =H. The general formulas (le) and (If) corresponding to general formula (I) with R 1 = C(O)R a or C(O)OR a where X and Y each represent O.

[0235] Stage a)

[0236] Compounds of general formula (Id) can be prepared from compounds of general formula (1) and oximes of general formula (4a). The reaction is carried out analogously to the procedure described in procedure A, step j).

[0237] Compounds of general formula (4a) can be obtained by analogy to the procedure described in procedure A, step a) for compounds of formula (4).

[0238] Stages b) and c)

[0239] Compounds of general formula (le) and (If) can be prepared from compounds of general formula (Id) and compounds of general formulas (14) and (15). The conversion is carried out analogously to the procedure described in Procedure B, steps a) and b).

[0240] A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 They have the meanings described above. The general formula (Ig) corresponds to the general formula I with X=O and Y=S.

[0241] Stage a)

[0242] Compounds of general formula (17) can be prepared from compounds of general formula (2a) by reaction with thiocarbonyl dichloride according to generally known methods, for example the method described in W020146066 or J. Am. Chem. Soc. 2008, 130, 16464-16465.

[0243] Compounds of general formula (2a) can be obtained by analogy to the procedure described in procedure A, step d).

[0244] Level b)

[0245] Compounds of general formula (Ig) can be prepared from compounds of general formula (17) and compounds of general formula (18) in analogy to the procedure described in WO2021261562.

[0246] Compounds of general formula (18) are known or can be prepared by known methods, for example analogous to the methods described in WO2021261562.

[0247] Procedure E A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 They have the meanings described above. The general formula (Ih) corresponds to the general formula I with X = S and Y = O.

[0248] Stage a)

[0249] Compounds of the general formula (Ih) can be prepared from compounds of formula (a) using a sulfurizing reagent, such as Lawesson's reagent, by analogy to the procedure described in WO2021261562, according to generally known methods, for example the procedure described in Tetrahedron Lett. 2008, 4579 or Org. Lett. 2019, 5848.

[0250] Procedure F

[0251] A, R 1 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 have the meanings described above. The general formula (li) corresponds to the general formula I, where Hal-R 2 for R 2 with the meaning described above, and wherein at least one substituent R 21 for CI, Br or I. The general formula (Ij) corresponds to the general formula I, where CN-R 2 for R 2with the meaning described above, and wherein at least one substituent R 21 stands for a nitrile.

[0252] Stage a)

[0253] Compounds of general formula (Ij) can be prepared from compounds of formula (li) with a cyanide salt, such as zinc cyanide. The reaction is carried out according to methods known in principle, such as those described in W0200537809, in the presence of a common inert solvent suitable for the prevailing reaction conditions, such as N,N-dimethylformamide, as well as in the presence of a palladium catalyst, such as tris(dibenzylideneacetone)dipalladium, and a suitable ligand, such as bis(diphenylphosphino)ferrocene. If necessary, a base, such as pyridine or diisopropylethylamine, can be added.

[0254] Compounds of the general formula (li) can be obtained by analogy to the procedure described under Procedure A. Procedure and uses

[0255] The invention also relates to methods for controlling animal pests, in which compounds of formula (I) are applied to animal pests and / or their habitat. The control of animal pests is preferably carried out in agriculture, forestry, and material protection. Methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods performed on the human or animal body are preferably excluded.

[0256] The invention further relates to the use of the compounds of formula (I) as pesticides, in particular plant protection products.

[0257] Within the scope of this application, the term pesticide always includes the term plant protection product.

[0258] The compounds of formula (I) are suitable, with good plant compatibility, favorable warm-blooded toxicity and good environmental compatibility, for the protection of plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the harvested crop and for controlling animal pests, especially insects, arachnids, helminths, especially nematodes, and molluscs, which occur in agriculture, horticulture, animal breeding, aquaculture, forestry, gardens and recreational facilities, stored product and material protection and in the hygiene sector.

[0259] Within the scope of this patent application, the term "hygiene" is to be understood as encompassing any and all measures, regulations, and procedures aimed at preventing diseases, particularly infectious diseases, and serving to protect the health of humans and animals, and / or the environment, and / or to maintain cleanliness. According to the invention, this includes, in particular, measures for cleaning, disinfecting, and sterilizing, for example, textiles or hard surfaces, especially surfaces made of glass, wood, cement, porcelain, ceramics, plastic, or metal(s), to ensure that these are free from pests and / or their excretions.Preferably excluded from the scope of protection of the invention are, in this respect, surgical or therapeutic treatment instructions and diagnostic instructions applicable to the human body or the bodies of animals.

[0260] The term "hygiene sector" encompasses all areas, technical fields, and industrial applications where hygiene measures, regulations, and procedures are important, for example, with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, hospitals, stables, animal farms, etc. The term "hygiene pest" should therefore be understood to mean one or more animal pests whose presence in the hygiene sector is problematic, particularly for health reasons. A primary objective is thus to prevent or minimize the presence of hygiene pests and / or exposure to them in the hygiene sector. This can be achieved, in particular, through the application of a pesticide that can be used both to prevent infestation and to control an existing infestation.Preparations that prevent or reduce exposure to pests can also be used. Hygiene pests include, for example, the organisms mentioned below.

[0261] The term "hygiene protection" therefore covers all actions by which these hygiene measures, regulations and procedures are maintained and / or improved.

[0262] The compounds of formula (I) can preferably be used as pesticides. They are effective against normally susceptible and resistant species, as well as against all or individual developmental stages. The pests mentioned above include:

[0263] Pests from the phylum Arthropoda, especially from the class Arachnida, e.g. Acarus spp., e.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., e.g. Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., e.g. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., e.g. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., e.g. Eutetranychus banksi, Eriophyes spp., e.g. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., z. B. Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., z. B.Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Omithodorus spp., Omithonyssus spp., Panonychus spp., z. B. Panonychus citri (=Metatetra- nychus 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., z. B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., z. B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; from the class of Chilopoda e.g. Geophilus spp., Scutigera spp.; from the order or class of Collembola e.g. Onychiurus armatus; Sminthurus viridis; from the class of Diplopoda e.g.Blaniulus guttulatus; from the class of Insecta, e.g. from the order of Blattodea e.g. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., e.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera e.g. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp., e.g. Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius, Agriotes spp., e.g. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., e.g. B. Anoplophora glabripennis, Anthonomus spp., e.g. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., e.g. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., e.g.Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., e.g. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., e.g. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., e.g. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., e.g. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferruginous, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus fumissi, Dendroctonus spp., e.g. B. Dendrocton ponderosae, Dermestes spp., Diabrotica spp., z. B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epi- lachna spp., z. B. Epilachna borealis, Epilachna varivestis, Epitrix spp., z. B. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gna- thocerus comutus, He Hula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylot- rupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z. B. Hypothenemus ham- pei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnostema consanguinea, Lasioderma ser- ricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa ​​decemlineata, Leucoptera spp., z. B. Leucoptera coffeella, Limonius ectypus, Lissorhoptrus oryzophilus, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., z. B. Megacyllene robiniae, Megascelis spp., Melanotus spp., z. B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., z. B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xan- thographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., e.g. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., e.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., e.g. Phyllotreta armoraciae, Phyllotreta pusilia, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., e.g. B. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Scolytus spp., e.g. Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp., e.g.Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium panicum, Sternechus spp., e.g. Sternechus paludatus, Symphyletes spp., Tanymecus spp., e.g. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides maureta- nicus, Tribolium spp., e.g. Tribolium audax, Tribolimn castaneum, Tribolimn confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., e.g. Zabrus tenebrioides; from the order of Dermaptera e.g. Anisolabis maritime, Forficula auricularia, Labidura riparia; from the order of Diptera e.g. Aedes spp., e.g. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., e.g. B. Agromyza frontella, Agromyza parvicomis, Anastrepha spp., Anopheles spp., z. B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., z. B.Bactrocera Cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., z. B. Contariniajohnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropo- phaga, Cricotopus sylvestris, Culex spp., z. B. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., z. B. Dasineura brassicae, Delia spp., z. B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., z. B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., z. B.Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., e.g. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musea spp., e.g. Musea domestica, Musea domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterbomiella subcincta, Pegomya or Pegomyia spp., e.g. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., e.g. Rhagoletis cingulata, Rha- goletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., e.g. B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., e.g. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; from the order of Hemiptera e.g. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiphon spp., e.g. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Ago- noscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus flocco- sus, Allocaridara malayensis, Amrasca spp., z. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., z. B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., z. B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis vibumiphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidi- otus spp., z. B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., e.g. Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Cameocephala ful- gida, Ceratovacuna lanigera, Cercopidae, Ceropiastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halb, Coccus spp., e.g. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., e.g. Dysaphis apiifolia, Dysaphis plant- taginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., e.g. B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., z. B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolima spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., z. B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., z. B. Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., z. B. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., z. B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costa- lis, Monelliopsis pecanis, Myzus spp., z. B. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus omatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., e.g. Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Onco- metopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., z. B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., z. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., z. B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., z. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Pianococcus spp., z. B. Pianococcus citri, Prosopidopsylla flava, Pro- topulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., z. B. Pseudococcus calceola- riae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus vibumi, Psyllopsis spp., Psylla spp., z. B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvi- naria spp., Pyrilla spp., Quadraspidiotus spp., z. B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastroccus spp., Rhopalosiphum spp., z.B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdo- minale, Saissetia spp., e.g. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., e.g. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., e.g. Trioza dio- spyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; from the suborder of Heteroptera e.g. B. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., e.g. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., z. B. Euschistus he- ros, 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., z. B. Lygocoris pabulinus, Lygus spp., z. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., z. B. Nezara viridula, Nysius spp., Oebalus spp., Pen- tomidae, Piesma quadrata, Piezodorus spp., z. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; from the order of Hymenoptera e.g. Acromyrmex spp., Athalia spp., e.g. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., e.g. Diprion similis, Hoplocampa spp., e.g. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., e.g. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., e.g. Vespa crabro, Wasmannia auropunctata, Xeris spp.; from the order of Isopoda e.g. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of Isoptera e.g. Coptotermes spp., e.g. B. Coptotermes formosanus, Comitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., e.g. Reticulitermes flavipes, Reticulitermes hesperus; from the order of Lepidoptera e.g. Achroia grisella, Acronicta major, Adoxophyes spp., e.g. Adoxophyes orana, Aedia leucomelas, Agrotis spp., e.g.Agrotis segetum, Agrotis ipsilon, Alabama spp., z. B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., z. B. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., z. B. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., z. B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., z. B. Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., z. B.Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., z. B. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., z. B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., z. B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., z. B. Heliothis virescens, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., z. B. Leucoptera coffeella, Lithocolletis spp., z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., z. B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., z. B. Lymantria dispar, Lyonetia spp., z. B.Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., z. B. Ostrinia nubilalis, Panolis flammea, Pamara spp., Pectinophora spp., z. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., z. B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., z. B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., z. B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutella maculipennis), Podesia spp., z. B. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., z. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., z. B. Schoenobius bipunctifer, Scirpophaga spp., z. B.Scirpophaga innotata, Scotia segetum, Sesamia spp., e.g. Sesamia inferens, Sparganothis spp., Spodoptera spp., e.g. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineolabisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., e.g. Trichoplusiani, Tryporyza incertulas, Tuta absoluta, Virachola spp.; from the order of Orthoptera or Sanatoria e.g. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., e.g. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., e.g. B. Locusta migratoria, Melanoplus spp., e.g. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order Phthiraptera e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; from the order of Psocoptera e.g. Lepinotus spp., Liposcelis spp.; from the order of Siphonaptera e.g. Ceratophyllus spp., Ctenocephalides spp., e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera e.g. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., e.g. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., e.g. B. Thrips palmi, Thrips tabaci; from the order of Zygentoma (= Thysanura), e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla, e.g. Scutigerella spp., e.g.Scutigerella Immaculata;

[0264] Pests from the phylum Mollusca, e.g., from the class Bivalvia, e.g., Dreissena spp.; as well as from the class Gastropoda, e.g., Arion spp., e.g., Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., e.g., Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.;

[0265] Plant pests from the phylum Nematoda, i.e. plant parasitic nematodes, in particular Aglenchus spp., e.g. Aglenchus agricola, Anguina spp., e.g. Anguina tritici, Aphelenchoides spp., e.g. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., e.g. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., e.g. Bursaphelenchus coco- philus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., e.g. Cacopaurus pestis, Criconemella spp., e.g. Criconemella curvata, Criconemella onoensis, Criconemella omata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., e.g. B. Crico- nemoides ferniae, Criconemoides onoense, Criconemoides omatum, Ditylenchus spp., e.g. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., e.g. Globodera pallida, Globodera rostochiensis, Helico- tylenchus spp., e.g. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Hete- rodera spp., e.g. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., e.g. Longidorus africanus, Meloidogyne spp., e.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacob- bus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., e.g. Para- ratrichodorus minor, Paratylenchus spp., Pratylenchus spp., e.g. Pratylenchus penetrans, Pseudoha- lenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., e.g. B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., z. B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., z. B. Tylenchorhynchus annulatus, Tylenchulus spp., z. B. Tylenchulus semipenetrans, Xiphinema spp., z. B. Xiphinema index.

[0266] Formulations

[0267] The present invention further relates to formulations, in particular formulations for controlling unwanted animal pests. The formulation can be applied to the animal pest and / or in its habitat.

[0268] The formulation according to the invention can be provided to the end user as a ready-to-use “application form”, i.e., the formulations can be applied directly to the plants or seeds using a suitable device such as a sprayer or duster. Alternatively, the formulations can be provided to the end user in the form of concentrates that are preferably to be diluted with water before application. Unless otherwise specified, the term “formulation” thus refers to such a concentrate, while the term “application form” refers to a solution ready for use by the end user, i.e., usually such a diluted formulation.

[0269] The formulation according to the invention can be produced in a conventional manner, for example by mixing the compound according to the invention with one or more suitable excipients such as those disclosed herein.

[0270] The formulation comprises at least one compound according to the invention and at least one agriculturally useful auxiliary material, e.g. carriers and / or surfactants.

[0271] A carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert. The carrier generally improves the release of compounds, for example, onto plants, plant parts, or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, especially ammonium sulfates, ammonium phosphates, and ammonium nitrates; ground natural rocks such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth; silica gel; and ground synthetic rocks such as finely divided silicon dioxide, aluminum oxide, and silicates. Examples of typical suitable solid carriers for the production of granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, and dolomite.Suitable liquid carriers include synthetic granules of inorganic and organic flours and granules of organic materials such as paper, sawdust, coconut shells, corncobs, and tobacco stalks. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include polar and nonpolar organic chemical liquids, for example, from the classes of aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatics, or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes, or methylene chloride), alcohols and polyols (which may also be substituted, etherified, and / or esterified, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, or glycol), and ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, or cyclohexanone).Esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (such as dimethylformamide or fatty acid amides) and esters thereof, lactams (such as N-alkylpyrrolidones, especially N-methylpyrrolidone) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide), oils of vegetable or animal origin, nitriles (alkyl nitriles such as acetonitrile, propionitrile, butyronitrile, or aromatic nitriles such as benzonitrile), carbonic acid esters (cyclic carbonic acid esters such as ethylene carbonate, propylene carbonate, butylene carbonate, or dialkyl carboxylic acid esters such as dimethyl carbonate, diethyl carbonate, dipropyl carbonate, dibutyl carbonate, dioctyl carbonate). The carrier can also be a liquefied gaseous extender, i.e., a liquid that is gaseous at normal temperature and pressure, for example, aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen, and carbon dioxide.

[0272] Preferred solid supports are selected from clays, talc and silicon dioxide.

[0273] Preferred liquid carriers are selected from water, fatty acid amides and esters thereof, aromatic and non-aromatic hydrocarbons, lactams, lactones, carbonic acid esters, ketones, (poly)etheme.

[0274] The amount of carrier is typically in the range of 1 to 99.99 wt.%, preferably 5 to 99.9 wt.%, particularly preferably 10 to 99.5 wt.%, and most preferably 20 to 99 wt.% of the formulation. Liquid carriers are typically present in the range of 20 to 90 wt.%, for example, 30 to 80 wt.% of the formulation.

[0275] Solid carriers are typically present in a range of 0 to 50 wt.%, preferably 5 to 45 wt.%, for example 10 to 30 wt.% of the formulation.

[0276] If the formulation includes two or more carriers, the outlined areas refer to the total number of carriers.

[0277] The surfactant can be an ionic (cationic or anionic), amphoteric or non-ionic surfactant such as ionic or non-ionic emulsifiers, foaming agents, dispersants, wetting agents, penetration enhancers and any mixtures thereof. Examples of suitable surfactants include, but are not limited to, salts of polyacrylic acid, ethoxylated poly(alpha-substituted)acrylate derivatives, salts of lignosulfonic acid (such as sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and / or propylene oxide with or without alcohols, fatty acids or fatty amines (for example, polyoxyethylene fatty acid esters such as castor oil ethoxylate, polyoxyethylene fatty alcohol ethers, for example, alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric acid esters of polyethoxylated alcohols or phenols.Fatty acid esters of polyols (such as fatty acid esters of glycerol, sorbitol, or sucrose), sulfates (such as alkyl sulfates and alkyl ether sulfates), sulfonates (for example, alkyl sulfonates, aryl sulfonates, and alkylbenzenesulfonates), sulfonated polymers of naphthalene / formaldehyde, phosphate esters, protein hydrolysates, lignosulfonate liquors, and methylcellulose are included. Where reference is made to salts in this paragraph, this preferably refers to the relevant alkali, alkaline earth, and ammonium salts.

[0278] Preferred surfactants are selected from ethoxylated poly(alpha-substituted) acrylate derivatives, polycondensates of ethylene oxide and / or propylene oxide with alcohols, polyoxyethylene fatty acid esters, alkylbenzenesulfonates, sulfonated polymers of naphthalene / formaldehyde, polyoxyethylene fatty acid esters such as castor oil ethoxylate, sodium lignosulfonate and arylphenol ethoxylate.

[0279] The amount of surfactant is typically in the range of 5 to 40 wt%, for example 10 to 20 wt%, of the formulation.

[0280] Other examples of suitable additives include water-repellent substances, desiccants, binders (adhesives, bonding agents, fixatives such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latizes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone and Tylose), thickeners and secondary thickeners (such as cellulose ethers, acrylic acid derivatives, xanthan gum, modified clays, e.g. the products available under the name Bentone, and finely divided silicon dioxide), stabilizers (e.g. cold stabilizers, preservatives (e.g.Dichlorophon, benzyl alcohol hemiformal, 1,2-benzisothiazolin-3-one, 2-methyl-4-isothiazolin-3-one), antioxidants, light stabilizers, especially UV stabilizers, and other agents that improve chemical and / or physical stability), dyes or pigments (such as inorganic pigments, e.g., iron oxide, titanium dioxide, and Prussian blue; organic dyes, e.g., alizarin, azo, and metal phthalocyanine dyes), antifoaming agents (e.g., silicone antifoaming agents and magnesium stearate), antifreeze, adhesives, gibberellins, and processing aids, mineral and vegetable oils, perfumes, waxes, nutrients (including trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc), protective colloids, thixotropic substances, penetrating agents, sequestrants, and complexing agents.

[0281] The selection of excipients depends on the intended application of the compound and / or the physical properties of the compound(s). Furthermore, excipients can be chosen to impart specific properties (technical, physical, and / or biological properties) to the formulations or the resulting application forms. The selection of excipients may allow formulations to be tailored to specific needs.

[0282] The formulation comprises an insecticidal / acaricidal / nematicidal effective amount of the inventive compound(s). The term "effective amount" refers to an amount sufficient to control insect pests / mites / nematodes on cultivated plants or for material protection, without causing significant damage to the treated plants. Such an amount can vary widely and depends on various factors, such as the insect / mite / nematode species to be controlled, the cultivated plant or material being treated, the climatic conditions, and the specific inventive compound used. The inventive formulation typically contains 0.01 to 99 wt.%, preferably 0.05 to 98 wt.%, particularly preferably 0.1 to 95 wt.%, even more preferably 0.5 to 90 wt.%, and most preferably 1 to 80 wt.% of the inventive compound. It is possible for a formulation to include two or more inventive combinations.In such a case, the outlined areas refer to the total quantity of compounds of the present invention.

[0283] The formulation according to the invention can be in any conventional formulation type, such as solutions (e.g., aqueous solutions), emulsions, water- and oil-based suspensions, powders (e.g., spray powders, soluble powders), dusts, pastes, granules (e.g., soluble granules, granules for spreading), suspoemulsion concentrates, natural or synthetic products impregnated with the compound according to the invention, fertilizers, and also microencapsulations in polymeric substances. The compound according to the invention can be in suspended, emulsified, or dissolved form. Examples of certain suitable formulation types include solutions, water-soluble concentrates (e.g., SL, LS), dispersion concentrates (DC), suspensions and suspension concentrates (e.g., SC, OD, OF, FS), emulsion concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME, SE), capsules (e.g., CS, ZC), pastes, lozenges, spray powders or dusts (e.g., WP, SP, WS, DP, DS), and pressed parts (e.g.,BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticidal articles (e.g., LN), and gel formulations for treating plant reproductive material such as seeds (e.g., GW, GF). These and other formulation types are defined by the Food and Agriculture Organization of the United Nations (FAO). An overview can be found in the "Catalogue of pesticide formulation types and international coding system," Technical Monograph No. 2, May 6, 2008, Croplife International.

[0284] Preferably, the formulation according to the invention is in the form of one of the following types: EC, SC, FS, SE, OD, WG, WP, CS, particularly preferably EC, SC, OD, WG, CS.

[0285] Further details on examples of formulation types and their preparation can be found below. If two or more compounds according to the invention are present, the outlined quantity of the compound according to the invention refers to the total quantity of the compounds of the present invention. Conversely, this also applies to all other components of the formulation if two or more representatives of such a component, e.g., a wetting agent or binder, are present. i) Water-soluble concentrates (SL, LS)

[0286] 10-60 wt% of at least one compound according to the invention and 5-15 wt% surfactant (e.g., polycondensates of ethylene oxide and / or propylene oxide with alcohols) are dissolved in such a quantity of water and / or water-soluble solvent (e.g., alcohols such as propylene glycol and carbonates such as propylene carbonate) as to result in a total amount of 100 wt%. The concentrate is diluted with water before use. ii) Dispersion concentrates (DC)

[0287] 5-25 wt% of at least one compound according to the invention and 1-10 wt% of surfactant and / or binder (e.g., polyvinylpyrrolidone) are dissolved in such an amount of organic solvent (e.g., cyclohexane) that a total of 100 wt% is obtained. Dilution with water yields a dispersion. iii) Emulsifiable Concentrates (EC)

[0288] 15-70 wt% of at least one compound according to the invention and 5-10 wt% of surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in such an amount of water-insoluble organic solvent (e.g., aromatic hydrocarbon or fatty acid amide) and, if necessary, additional water-soluble solvent, as to achieve a total amount of 100 wt%. Dilution with water yields an emulsion. iv) Emulsions (EW, EO, ES)

[0289] 5-40 wt% of at least one compound according to the invention and 1-10 wt% surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, or polycondensates of ethylene oxide and / or propylene oxide with or without alcohols) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g., aromatic hydrocarbon). The mixture is added to water using an emulsifying machine to achieve a total volume of 100 wt%. The resulting formulation is a homogeneous emulsion. Before use, the emulsion can be further diluted with water. v) Suspensions and Suspension Concentrates v-1) Water-based (SC, FS)

[0290] In a suitable grinding device, e.g., a ball mill, 20–60 wt.% of at least one compound according to the invention are ground to a fine active ingredient suspension with the addition of 2–10 wt.% surfactant (e.g., sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1–2 wt.% thickener (e.g., xanthan gum), and water. Water is added in such a quantity as to obtain a total of 100 wt.%. Dilution with water yields a stable suspension of the active ingredient. For FS-type formulations, up to 40 wt.% binder (e.g., polyvinyl alcohol) is added. v-2) Oil-based (OD, OF)

[0291] In a suitable grinding device, e.g., a ball mill, 20-60 wt.% of at least one compound according to the invention are ground to a fine active ingredient-oil suspension with the addition of 2-10 wt.% surfactant (e.g., sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2 wt.% thickening agent (e.g., modified clay, in particular bentone, or silicon dioxide), and an organic carrier. The organic carrier is added in such an amount as to obtain a total quantity of 100 wt.%. Dilution with water yields a stable dispersion of the active ingredient. vi) Water-dispersible granules and water-soluble granules (WG, SG)

[0292] 1-90 wt.%, preferably 20-80 wt.%, most preferably 50-80 wt.% of at least one compound according to the invention are finely ground with the addition of a surfactant (e.g., sodium lignosulfonate and sodium alkyl inaphthylsulfonate) and optionally a carrier material, and converted into water-dispersible or water-soluble granules by means of typical technical processes such as extrusion, spray drying, or fluidized bed granulation. The surfactant and carrier material are used in such quantities as to obtain a total of 100 wt.%. Dilution with water yields a stable dispersion or solution of the active ingredient. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0293] 50-80 wt% of at least one compound according to the invention are milled in a rotor-stator mill with the addition of 1-20 wt% surfactant (e.g., sodium lignosulfonate, sodium alkylnaphthylsulfonates) and an amount of solid support, e.g., silica gel, sufficient to achieve a total of 100 wt%. Dilution with water yields a stable dispersion or solution of the active ingredient. viii) Gel (GW, GF)

[0294] In a ball mill, 5-25 wt% of at least one compound according to the invention are ground with the addition of 3-10 wt% surfactant (e.g., sodium lignosulfonate), 1-5 wt% binder (e.g., carboxymethylcellulose), and enough water to reach a total of 100 wt%. This yields a fine suspension of the active ingredient. Dilution with water produces a stable suspension of the active ingredient. ix) Microemulsion (ME)

[0295] 5-20 wt% of at least one compound according to the invention are added to 5-30 wt% of an organic solvent mixture (e.g., fatty acid dimethylamide and cyclohexanone), 10-25 wt% of a surfactant mixture (e.g., polyoxyethylene fatty alcohol ether and arylphenol ethoxylate), and enough water to reach a total of 100 wt%. This mixture is stirred for 1 h, during which a thermodynamically stable microemulsion spontaneously forms. x) Microcapsules (CS)

[0296] An oil phase containing 5-50 wt% of at least one compound according to the invention, 0-40 wt% of water-insoluble organic solvent (e.g., aromatic hydrocarbon), and 2-15 wt% of acrylic monomers (e.g., methyl methacrylate, methacrylic acid, and a di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Radical polymerization initiated with a radical initiator leads to the formation of poly(methyl)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of at least one compound according to the invention, 0-40 wt% of water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol), leading to the formation of polyurea microcapsules. Optionally, the addition of a polyamine (e.g.,Hexamethylenediamine) is used to induce the formation of polyhydroxy microcapsules. The monomers constitute 1-10 wt% of the total CS formulation. xi) Dust powder (DP, DS).

[0297] 1-10 wt% of at least one compound according to the invention are finely ground and thoroughly mixed with such an amount of solid carrier, e.g., finely divided kaolin, that a total quantity of 100 wt% is achieved. xii) Granules (GR, FG)

[0298] 0.5–30 wt.% of at least one compound according to the invention are finely ground and associated with such an amount of solid support (e.g., silicate) that a total of 100 wt.% is achieved. xiii) Ultra-low volume liquids (UL)

[0299] 1-50 wt.% of at least one compound according to the invention are dissolved in such an amount of organic solvent, e.g. aromatic hydrocarbon, that a total amount of 100 wt.% is achieved.

[0300] Formulation types i) to xiii) may include further excipients such as 0.1-1 wt.% preservatives, 0.1-1 wt.% antifoaming agents, 0.1-1 wt.% colorants and / or pigments and 5-10 wt.% antifreeze.

[0301] Mixtures

[0302] The compounds of formula (I) can also be used in mixtures with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiological agents, beneficial organisms, herbicides, fertilizers, bird repellents, phytotonics, sterilizants, safeners, semiochemicals, and / or plant growth regulators to, for example, broaden the spectrum of activity, prolong the duration of action, increase the speed of action, prevent repellency, or prevent the development of resistance. Furthermore, such combinations of active ingredients can improve plant growth and / or tolerance to abiotic factors such as high or low temperatures, drought, or increased water or soil salinity.It is also possible to improve flowering and fruiting behavior, optimize germination and rooting, facilitate harvesting and increase yield, influence ripening, increase the quality and / or nutritional value of the harvested products, extend storage life and / or improve the processing of the harvested products.

[0303] Furthermore, the compounds of formula (I) may be present in mixtures with other active ingredients or semiochemicals, such as attractants and / or bird repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of formula (I) may be used to improve plant characteristics such as growth, yield, and the quality of the emtegu tes.

[0304] In a particular embodiment of the invention, the compounds of formula (I) are present in formulations or in application forms prepared from these formulations in mixture with other compounds, preferably such as those described below.

[0305] If any of the compounds mentioned below can exist in different tautomeric forms, these forms are also included, even if they are not explicitly named in every case. Furthermore, all the mixture components mentioned can, if their functional groups allow, form salts with suitable bases or acids.

[0306] Insecticides / Acaricides / Nematicides

[0307] The active ingredients listed here by their "common name" are well-known and described, for example, in the Pesticide Manual ("The Pesticide Manual," 16th ed., British Crop Protection Council 2012) or can be found online (e.g., http: / / www.alanwood.net / pesticides). The classification is based on the IRAC Mode of Action Classification Scheme valid at the time of filing this patent application.

[0308] (1) Acetylcholinesterase(AChE)-Inhibitoren, vorzugsweise Carbamate ausgewählt aus Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanat, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamat, Trimethacarb, XMC und Xylylcarb, oder Organophosphate ausgewählt aus Acephat, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos-methyl, Coumaphos, Cyano- phos, Demeton-S-methyl, Diazinon, Dichlorvos / DDVP, Dicrotophos, Dimethoat, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazat, Hep- tenophos, Imicyafos, Isofenphos, Isopropyl-O-(methoxyaminothio-phosphoryl)salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoat, Oxydemeton-methyl, Parathion-methyl,Phenthoate, phorate, phosalon, phosmet, phosphamidone, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and Vamidothione.,

[0309] (2) GABA-gated chloride channel blockers, preferably cyclodiene organochlorines selected from chlordane and endosulfan, or phenylpyrazoles (fiproles) selected from ethiprol and fipronil.

[0310] (3) Natrium-Kanal-Modulatoren, vorzugsweise Pyrethroide ausgewählt aus Acrinathrin, Allethrin, d- cis-trans-Allethrin, d-trans-Allethrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentenyl-Isomer, Bi- oresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma- Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta-Cyper- methrin, Cyphenothrin [(lR)-trans-Isomer], Deltamethrin, Empenthrin [(EZ)-(lR)-Isomer], Esfenvale- rat, Etofenprox, Fenpropathrin, Fenvalerat, Flucythrinat, Flumethrin, tau-Fluvalinat, Halfenprox, Imiprothrin, Kadethrin, Momfluorothrin, Permethrin, Phenothrin [(lR)-trans-Isomer], Prallethrin, Pyrethrine (Pyrethrum), Renofluthrin, Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)-Isomer], Tralomethrin und Transfluthrin, oder DDT oder Methoxychlor.

[0311] (4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), preferably neonicotinoids selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoximines selected from sulfoxaflor, or butenolides selected from flupyradifurone, or mesoionics selected from dicloromezotiaz and triflumezopyrim, or pyridylidenes selected from flupyrimine.

[0312] (5) Allosteric modulators of the nicotinic acetylcholine receptor (nAChR, binding site I), preferably spinosynes selected from spinetoram and spinosad.

[0313] (6) Allosteric modulators of the glutamate-dependent chloride channel (GluCl), preferably avermectins / milbemycins selected from abamectin, emamectin benzoate, lepimectin and mitbemycin.

[0314] (7) Juvenile hormone mimetics, preferably juvenile hormone analogues selected from hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.

[0315] (8) Various non-specific (multi-site) inhibitors, preferably alkyl halides selected from methyl bromide and other alkyl halides, or chloropicrin or sulfuryl fluoride or borax or tartar emetic or methyl isocyanate generators selected from diazomet and metam.

[0316] (9) TRPV channel modulators of chordotonal organs, preferably pyridinazomethanes selected from pymetrozine and pyrifluquinazone or pyropenes selected from afidopyropene. (10) CHS1-related mite growth inhibitors selected from clofentezine, hexythiazox, diflovidazine and etoxazole.

[0317] (11) Microbial disruptors of the insect intestinal membrane selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and Bt plant proteins selected from CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb and Cry 34 Ab 1 / 35 Abi.

[0318] (12) Inhibitors of mitochondrial ATP synthase, preferably ATP disruptors selected from diafenthiuron, or organotin compounds selected from azocyclotin, cyhexatin and fenbutatin oxide, or propargite or tetradifone.

[0319] (13) Uncouplers of oxidative phosphorylation by disturbance of the proton gradient selected from chlorfenapyr, DNOC and sulfuramide.

[0320] (14) Blockers of the nicotinic acetylcholine receptor channel selected from Bensultap, Cartap hydrochloride, thiocyclam and Thio sultap sodium.

[0321] (15) Inhibitors of chitin biosynthesis relating to CHS1, preferably benzoyl inhibitors selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0322] (16) Inhibitors of chitin biosynthesis, type 1 selected from buprofezin.

[0323] (17) Molting disruptors (especially in Diptera, i.e., true flies) selected from cyromazine.

[0324] (18) Ecdysone receptor agonists, preferably diacylhydrazines selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0325] (19) Octopamine receptor agonists selected from amitraz.

[0326] (20) Mitochondrial complex III electron transport inhibitors selected from hydramethylnone, acequinocyl, fluacrypyrim and bifenazate.

[0327] (21) Mitochondrial complex I electron transport inhibitors, preferably METI acaricides and insecticides selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris). (22) Voltage-gated sodium channel blockers, preferably oxadiazines selected from indo-xacarb or semicarbazones selected from metaflumizone.

[0328] (23) Inhibitors of acetyl-CoA carboxylase, preferably tetronic and tetramic acid derivatives selected from spirodiclofen, spiromesifen, spiropide ion and spirotetramate.

[0329] (24) Inhibitors of mitochondrial complex IV electron transport, preferably phosphides selected from aluminium phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides selected from calcium cyanide, potassium cyanide and sodium cyanide.

[0330] (25) Inhibitors of mitochondrial complex II electron transport, preferably beta-ketonitrile derivatives selected from cyenopyrafen and cyflumetofen, or carboxanilides selected from pyflubumide.

[0331] (28) Ryanodine receptor modulators, preferably diamides selected from chloroantraniliproles, cyantraniliproles, cyclaniliproles, flubendiamides and tetraniliproles.

[0332] (29) Chordotonal organs: Nicotinamidase inhibitors selected from flonicamide.

[0333] (30) Allosteric modulators of the GABA-dependent chloride channel, preferably meta-diamides selected from broflanilide or isoxazoles selected from fluxametamide and isocycloseram.

[0334] (31) Baculoviruses, preferably granuloviruses (GVs) selected from Cydia pomonella GV and Thaumatibia leucotreta (GV) or nucleopolyhedroviruses (NPVs) selected from Anticarsia gemmatalis MNPV, Flucypyriprol and Helicoverpa armigera NPV.

[0335] (32) Allosteric modulators (binding site II) of the nicotinic acetylcholine receptor selected from GS-omega / kappa-HXTX-Hvla peptide.

[0336] (33) Calcium-activated potassium channel KCa2 modulators selected from Acynonapyr.

[0337] (34) Mitochondrial complex III electron transport inhibitors (non-Qo binding site) selected from flometoquine.

[0338] (36) Modulators of chordotonal organs (Undefined binding site), selected from dimpropyridaz.

[0339] (UN) Compounds with an unknown or unclear mechanism of action (the target protein responsible for the biological activity is unknown or uncharacterized), selected from azadirachtin, benzoximates, benzopyrimoxane, bromopropylates, quinomethionate, dicofol, mancozeb, oxazosulfyl, pyridalyl, sulfur, and lime sulfur. (UNB) Bacterial agents (non-Bt) with an unknown or unclear mechanism of action (the target protein responsible for the biological activity is unknown or uncharacterized), selected from Burkholderia spp. and Wolbachia pipientis (ZAP).

[0340] (UNE) Botanical essences, including synthetic, extracted and unrefined oils of unknown or unclear mechanism of action (the target protein responsible for biological activity is unknown or not characterized), selected from Chenopodium ambrosioides near ambrosioides extracts and glycerol and propanediol fatty acid monoesters of neem oil.

[0341] (UNF) Fungal agents of unknown or unclear mechanism of action (the target protein responsible for biological activity is unknown or uncharacterized), selected from Beauveria bassiana strains, Metarhizium anisopliae strain F52, and Paecilomyces fumosoroseus Apopka strain 97.

[0342] (UNM) Non-specific mechanical and physical disruptors (the target protein responsible for biological activity is unknown or uncharacterized), selected from silica and mineral oil.

[0343] (UNP) Peptides with unknown mechanism of action, selected from Ul-AGTX-Talb-QA.

[0344] Inhibitory nucleic acid molecules, preferably inhibitory ribonucleic acid molecules (RNAi), preferably inhibitory ribonucleic acid molecules (RNAi) selected from Vadescana (Varroa destructor calmodulin gene-specific double-stranded interfering EP15).

[0345] Other active ingredients selected from Afoxolaner, Bentioflumen, Bisulflufen, Chloroprallethrin, Cryolite, Cybenzoxasulfyl, Cycloxapride, Cyetpyrafen, Cyhalodiamides, Cyproflanilide (CAS 2375110-88-4), Esa-foxolaner, epsilon-Metofluthrin, epsilon-Momfluthrin, Fenmezoditiaz, Fluchlordiniliprole, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafone, Fluralaner, Fufenozide, Flupentiofenox, Flupyroxystrobin, Guadipyr, Heptafluthrin, Imidaclothiz, Indazapyroxamet, Iprodione, Isoflualanam, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin Mivorilaner, Modoflaner, Nicofluprole (CAS 1771741-86-6), Paichongding, Pioxaniliprole, Piperflanilide, Pyriminostrobin, Sarolaner, Spidoxamate, Spirobudifen, Sulfiflumine, Tetramethylfluthrin, Tetrachlorantraniliprole, Tigolaner, Tiapyrachlor, Tiorantraniliprole, thiofluoximates, tyclopyrazoflor, umifoxolaner; iodomethane;Furthermore, preparations based on Bacillus firmus (1-1582, Votivo), azadirachtin (BioNeem) and Ledprona (Calantha®), pelargonic acid (known from WO 2023148028 Al) and the following compounds: l-{2-Fhior-4-methyl-5-[(2,2,2-trifhiorethyl)sulfinyl]phenyl}-3-(trifhiormethyl)-lH-l,2,4-triazol-5-amine (known from WO 2006043635) (CAS 885026-50-6), 2-chloro-N-[2-{l-[(2E)-3-(4-chlorophenyl)prop-2-en-l-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl] isonicotinamide (known from WO 2006003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3-(4-Chloro-2,6-dimethylphenyl)-8-methoxy-;

[0346] 2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus EP 2647626) (CAS1440516-42-6), PF1364 (bekannt aus JP 2010018586) (CAS 1204776-60-2), (3E)-3-[l-[(6-Chlor-3-pyridyl)methyl]-2- pyridyliden]-l,l,l-trifluorpropan-2-on (bekannt aus WO 2013144213) (CAS 1461743-15-6), N-[3- (Benzylcarbamoyl)-4-chlorphenyl]-l-methyl-3-(pentafluorethyl)-4-(trifluomiethyl)-lH-pyrazol-5-car- boxamid (bekannt aus WO 2010051926) (CAS 1226889-14-0), 5-Brom-4-chlor-N-[4-chlor-2-methyl- 6-(methylcarbamoyl)phenyl]-2-(3-chlor-2-pyridyl)pyrazol-3 -carboxamid (bekannt aus CN 103232431) (CAS 1449220-44-3), 4-[5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluomiethyl)-3-isoxazolyl]-2-nie- thyl-N-(cis-l-oxido-3-thietanyl)benzamid, 4-[5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluomiethyl)-3- isoxazolyl]-2-methyl-N-(trans-l-oxido-3-thietanyl)benzamid und 4-[(5S)-5-(3,5-Dichlorphenyl)-4,5- dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N-(cis-l-oxido-3-thietanyl)benzamid (bekannt aus WO 2013050317 Al) (CAS 1332628-83-7), N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3- [(3,3,3-trifluorpropyl)sulfinyl]propanamid, (+)-N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-,

[0347] 3-[(3,3,3-trifluorpropyl)sulfinyl]propanamid und (-)-N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N- ethyl-3-[(3,3,3-trifluorpropyl)sulfinyl]propanamid (bekannt aus WO 2013162715 A2, WO 2013162716 A2, US 20140213448 Al) (CAS 1477923-37-7), 5-[[(2E)-3-Chlor-2-propen-l-yl]amino]-l-[2,6-dich- lor-4-(trifluormethyl)phenyl]-4-[(trifluomiethyl)sulfinyl]-lH-pyrazol-3-carbonitrile (bekannt aus CN 101337937 A) (CAS 1105672-77-2), 3-Brom-N-[4-chlor-2-methyl-6-[(methylamino)thioxome- thyl]phenyl]-l-(3-chlor-2-pyridinyl)-lH-pyrazol-5-carboxamid, (Liudaibenjiaxuanan, bekannt aus CN 103109816 A) (CAS 1232543-85-9), N-[4-Chlor-2-[[(l,l-dimethylethyl)amino]carbonyl]-6-methyl- phenyl]-l-(3-chlor-2-pyridinyl)-3-(fluormethoxy)-lH-pyrazol-5-carboxamid (bekannt aus WO 2012034403 Al) (CAS 1268277-22-0), N-[2-(5-Amino-l,3,4-thiadiazol-2-yl)-4-chlor-6-methylphe- nyl]-3-brom-l-(3-chlor-2-pyridinyl)-lH-pyrazol-5-carboxamid (bekannt aus WO 2011085575 Al) (CAS 1233882-22-8), 4-[3-[2,6-Dichlor-4-[(3,3-dichlor-2-propen-l-yl)oxy]phenoxy]propoxy]-2-me- thoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN 101337940 A) (CAS 1108184-52-6), (2E)- und 2(Z)-2-[2-(4-Cyanophenyl)-l-[3-(trifluormethyl)phenyl]ethyliden]-N-[4-(difluormethoxy)phenyl]hyd- razincarboxamid (bekannt aus CN 101715774 A) (CAS 1232543-85-9), Cyclopropancarbonsäure-3- (2,2-dichlorethenyl)-2,2-dimethyl-4-(lH-benzimidazol-2-yl)phenylester (bekannt aus CN 103524422 A) (CAS 1542271-46-4), (4aS)-7-Chlor-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluorme- thyl)thio]phenyl]amino]carbonyl]indeno[l,2-e][l,3,4]oxadiazin-4a(3H)-carbonsäuremethylester (bekannt aus CN 102391261 A) (CAS 1370358-69-2), 6-Desoxy-3-O-ethyl-2,4-di-O-methyl-l-[N-[4-[l- [4-( 1 , 1 ,2,2,2-pentafluorethoxy)pheny 1] - 1H- 1 ,2,4-triazol-3 -y l]phenyl]carbamat] -a-L-mannopyranose (bekannt aus US 2014 / 0275503 Al) (CAS 1181213-14-8), 8-(2-Cyclopropylmethoxy-4-trifluormethyl- phenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octan (CAS 1253850-56-4),(8-anti)- 8-(2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluomiethylpyridazin-3-yl)-3- azabicyclo[3.2.1]octan (CAS 933798-27-7), (8-syn)-8-(2-Cyclopropylmethoxy-4-trifluormethylphen- oxy)-3-(6-trifluormethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octan (bekannt aus WO 2007040280 Al, WO 2007040282 Al) (CAS 934001-66-8), N- [4- (Aminothioxomethyl) - 2- methyl- 6- [(methylamino) carbonyl] phenyl] - 3- brom- 1- (3- chlor- 2- pyridinyl) - lH-pyrazol-5-carboxamid (bekannt aus CN 103265527 A) (CAS 1452877-50-7), 3- (4- Chlor- 2, 6- dimethylphenyl) - 8- methoxy- 1- methyl-1,8- diazaspiro[4.5]decan-2,4-dion (bekannt aus WO 2014187846 Al) (CAS 1638765-58-8), 3- (4- Chlor- 2, 6- dimethylphenyl) - 8- methoxy- 1- methyl- 2- oxo- 1, 8- diazaspiro[4.5] dec- 3- en- 4- yl-carbon- säureethylester (bekannt aus WO 2010066780 Al, WO 2011151146 Al) (CAS 1229023-00-0), N- [1- (2, 6- Difluorphenyl) - 1H- pyrazol- 3- yl] - 2- (trifluormethyl) benzamid (bekannt aus WO 2014053450 Al) (CAS 1594624-87-9),N- [2- (2, 6- Difluorphenyl) - 2H- 1, 2, 3- triazol- 4- yl] - 2- (trifluormethyl) benzamid (bekannt aus WO 2014053450 Al) (CAS 1594637-65-6), N- [1- (3, 5-Difluor- 2- pyridinyl),

[0348] - 1H- pyrazol- 3- yl] - 2- (trifluormethyl) benzamid (bekannt aus WO 2014053450 Al) (CAS 1594626- 19-3), A-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-2-(methylsulfonyl)-propanamid (bekannt aus WO 2019 / 236274 Al) (CAS 2396747-83-2), N- [2- Brom- 4- [1, 2, 2, 2- tetrafluor- 1- (trifluormethyl) ethyl]

[0349] - 6- (trifluormethyl) phenyl] - 2- fluor- 3- [(4- fluorbenzoyl) amino] -benzamid (bekannt aus WO 2019059412 Al) (CAS 1207977-87-4), 2-(5-Cyclopropyl-3-ethylsulfonyl-2-pyridyl)-5-(trifluormethyl- sulfinyl)-l,3-benzoxazol (bekannt aus WO 2017146226 Al) (CAS 2128706-04-5), 6-(5-Cyclopropyl- 3-ethylsulfonyl-2-pyridyl)-2,2-difluor-7-methyl-[l,3]dioxolo[4,5-f]benzimidazol (bekannt aus WO 2020013147 Al) (CAS 2408220-91-5), l-[6-(2,2-Difluor-7-methyl-[l,3]dioxol[4,5-f|benzimidazol-6- yl)-5-ethylsulfonyl-3-pyridyl]cyclopropan-carbonitril (bekannt aus WO 2020013147 Al) (CAS 2408220-94-8), 2-(3-Ethylsulfonyl-2-pyridyl)-5-(2,2,3,3,3-pentafluorpropoxy)pyrazin (bekannt aus WO 2017065228 Al) (CAS 2095470-94-1), 5-[[(lR,3R)-3-[3,5-Bis(trifluormethyl)phenyl]-2,2-dich- lor-cyclopropancarbonyl]amino]-2-chlor-N-[3-[(2,2-difluoracetyl)amino]-2,4-difluor-phe- nyl]benzamid (bekannt aus WO 2022072650 Al) (CAS 2649032-72-2), 2-Chlor-N-[3-[(2,2-diflu- oracetyl)amino]-2,4-difluor-phenyl]-5-[[rel-(lR,3R)-3-[3,5-bis(trifluoromethyl)phenyl]-2,2-dichlorocyclopropanecarbonyl]amino]benzamide (known from WO 2018071327 Al) (CAS 2220132-55-6).,

[0350] Fungicides

[0351] The active ingredients specified here by their “Common Name” are known and are described, for example, in the “Pesticide Manual” (16th edition, British Crop Protection Council) or can be researched on the Internet (e.g., www.alanwood.net / pesticides).

[0352] All the aforementioned mixture components of classes (1) to (15) can, if their functional groups allow, form salts with suitable bases or acids. If one of the mixture components can exist in tautomeric form, such a compound is to be understood as including corresponding tautomeric forms in the preceding and subsequent sections.

[0353] 1) Inhibitoren der Ergosterol-Biosynthese, beispielsweise (1.001) Cyproconazol, (1.002) Difenocona- zol, (1.003) Epoxiconazol, (1.004) Fenbuconazol, (1.005) Fenhexamid, (1.006) Fenpropidin, (1.007) Fenpropimorph, (1.008) Fenpyrazamin, (1.009) Fluoxytioconazol, (1.010) Fluquinconazol, (1.011) Flu- triafol, (1.012) Hexaconazol, (1.013) Imazalil, (1.014) Imazalilsulfat, (1.015) Ipconazol, (1.016) Ipfen- trifluconazol, (1.017) Mefentrifluconazol, (1.018) Metconazol, (1.019) Myclobutanil, (1.020) Paclobu- trazol, (1.021) Penconazol, (1.022) Prochloraz, (1.023) Propiconazol, (1.024) Prothioconazol, (1.025) Pyrisoxazol, (1.026) Spiroxamin, (1.027) Tebuconazol, (1.028) Tetraconazol, (1.029) Triadimenol, (1.030) Tridemorph, (1.031) Triticonazol, (1.032) 4-[[6-[(2R)-2-(2,4-Difluorphenyl)-l,l-difluor-2-hy- droxy-3-(5-thioxo-4H-l,2,4-triazol-l-yl)propyl]-3-pyridyl]oxy]-benzo-nitril, (1.033) 4-[[6-[(2S)-2- (2,4-Difluorpheny 1)- 1 , 1 -difluor-2-hy droxy-3-(5 -thioxo-4H- 1 ,2,4-triazol- 1 -yl)propyl] -3 -py- ridyl]oxy]benzonitril, (1.034) (2R)-2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)-phenyl]-l-(lH-l,2,4-tria- zol-l-yl)propan-2-ol, (1.035) (2S)-2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)-phenyl]-l-(lH-l,2,4-tria- zol-l-yl)propan-2-ol, (1.036) l-({(2R,4S)-2-[2-Chlor-4-(4-chlorphenoxy)-phenyl]-4-methyl-l,3- dioxolan-2-yl}methyl)-lH-l,2,4-triazol, (1.037) l-({(2S,4S)-2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-4- methyl-l,3-dioxolan-2-yl}methyl)-lH-l,2,4-triazol, (1.038) 2-[6-(4-Brom-phenoxy)-2-(trifluor- methyl)-3-pyridyl]-l-(l,2,4-triazol-l-yl)propan-2-ol, (1.039) 2-[6-(4-Chlor-phenoxy)-2-(trifluor- methyl)-3-pyridyl]-l-(l,2,4-triazol-l-yl)propan-2-ol, (1.040) 3-[2-(l-Chlorcyclo-propyl)-3-(3-chlor-2- fluorphenyl)-2-hydroxy propyl] imidazol-4-carbonitril, ( 1.041) 2- [2-Chlor-4-(4-chlorphenoxy)pheny 1] - 2-hydroxy-3-(lH-l,2,4-triazol-l-yl)propansäuremethylester, (1.042) (2R)-2-[2-Chlor-4-(4-chlorphe- noxy)phenyl]-2-hydroxy-3-(lH-l,2,4-triazol-l-yl)propansäure-methyl-ester, (1.043) (S)-2-[2-Chlor-4- (4-chlorphenoxy)phenyl]-2-hydroxy-3-(lH-l,2,4-triazol-l-yl)propan-säure-methyl-ester, (1.044) N'- (2,5-Dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methyl-formimidamid, (1.045) N'-(2-Chlor-4-(4- cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamid, (1.046) N'-(2-Chlor-4-(4- methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamid, (1.047) N'-(2-Chlor-5-methyl-4- phenoxyphenyl)-N-ethyl-N-methylimido-formamid, (1.048) N'-(4-Benzyl-2-chlor-5-methyl-phenyl)- N-ethyl-N-methylformimidamid, (1.049) N'-[2-Chlor-4-(2-fluorphenoxy)-5-methylphenyl]-N-ethyl-N- methylimidoformamid, (1.050) N'-[5-Brom-6-(2,3-dihydro-lH-inden-2-yloxy)-2-methyl-pyridin-3-yl]- N-ethyl-N-methylimidoformamid, (1.051) N'-{4-[(4,5-Dichlor-l,3-thiazol-2-yl)oxy]-2,5-di- methylphenyl}-N-ethyl-N-methylimidoformamid, (1.052) N'-{5-Brom -2 -methyl-6-[(l -propoxy -pro- pan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylimido-formamid, (1.053) N'-{5-Brom-6-[(lR)-l-(3,5-di- fluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.054) N'-{5-Brom-6- [(lS)-l-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.055) N'-{5-Brom-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyl-imido-for- mamid, (1.056) N'-{5-Brom-6-[(trans-4-isopropyl-cyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N- methylimidoformamid, (1.057) N'-{5-Brom-6-[l-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N- ethyl-N-methylimidoformamid, (1.058) N-Isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluor-l-hy- droxy-l-phenylethyl)phenyl]-N-methyl-imido-formamid, (1.059) 4-[(E)-[Ethyl(methyl)-amino]methy- lenamino]-2,5-dimethyl-benzoesäure-p-tolylmethylester, (1.060) N'-(2,5-Dimethyl-4-phenoxy- phenyl)-N-ethyl-N-methyl-formamidin.

[0354] 2) Inhibitoren der Atmungskette am Komplex I oder II, beispielsweise (2.001) Benzovindiflupyr, (2.002) Bixafen, (2.003) Boscalid, (2.004) Carboxin, (2.005) Cyclobutrifluram, (2.006) Flubeneteram, (2.007) Fluindapyr, (2.008) Fluopyram, (2.009) Flutolanil, (2.010) Fluxapyroxad, (2.011) Furametpyr, (2.012) Inpyrfluxam, (2.013) Isofetamid, (2.014) Isoflucypram, (2.015) Isopyrazam, (2.016) Penflufen, (2.017) Penthiopyrad, (2.018) Pydiflumetofen, (2.019) Pyrapropoyn, (2.020) Pyraziflumid, (2.021) Se- daxan, (2.022) Thifluzamid (auch bekannt als Trifluzamid), (2.023) 5,8-Difhior-N-[2-(2-fluor-4-{[4- (trifluormethyl)pyridin-2-yl]oxy}phenyl)ethyl]chinazolin-4-amin, (2.024) 5-Chlor-N-[2-[l-(4- chlorpheny l)py razol-3 -y 1] oxy ethyl] -6-ethy Ipy rimidin-4-amin, (2.025) N-[2-[l -(4-Chlorpheny l)py ra- zol-3-yl]oxyethyl]chinazolin-4-amin, (2.026) l-Methyl-3-(trifhiormethyl)-N-[2'-(trifluor- methyl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (2.027) 2-Fhior-6-(trifhiormethyl)-N-(l,l,3-tri- methyl-2,3-dihydro-lH-inden-4-yl)benzamid, (2.028) 3-(Difhiormethyl)-l-methyl-N-(l,l,3-trimethyl-.

[0355] 2.3-dihydro-lH-inden-4-yl)-lH-pyrazol-4-carboxamid, (2.029) 3-(Difluormethyl)-l-methyl-N-[(3S)-

[0356] 1.1.3 -trimethy 1-2,3 -dihy dro- lH-inden-4-y 1] - 1 H-pyrazol-4-carboxamid, (2.030) 3 -(Difluormethyl)-N- [(3R)-7-fluor-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazol-4-carboxamid, (2.031)

[0357] 3-(Difhiormethyl)-N-[(3S)-7-fhior-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazol-

[0358] 4-carboxamid, (2.032) N-[(lR,4S)-9-(Dichlormethylen)-l,2,3,4-tetrahydro-l,4-methanonaphthalin-5- yl] -3 -(difluormethyl)-l -methyl- lH-pyrazol-4-carboxamid, (2.033) N-[(lS,4R)-9-(Dichlormethylen)- l,2,3,4-tetrahydro-l,4-methanonaphthalin-5-yl]-3-(difluormethyl)-l-methyl-lH-pyrazol-4-carboxa- mid, (2.034) N-[l-(2,4-Dichlorphenyl)-l-methoxypropan-2-yl]-3-(difluormethyl)-l-methyl-lH-pyra- zol-4-carboxamid, (2.035) 5-Chlor-l,3-dimethyl-N-[(3S)-l,l,3-trimethyl-3H-isobenzofuran-4-yl]pyra- zol-4-carboxamid, (2.036) 5-Chlor-l,3-dimethyl-N-[(3R)-l,l,3-trimethyl-3H-isobenzofuran-4-yl]pyra- zol-4-carboxamid, (2.037) N-[2-[(lS)-l,3-Dimethylbutyl]phenyl]-5-fluor-l,3-dimethyl-pyrazol-4-car- boxamid, (2.038) N-[2-[(lR)-l,3-Dimethylbutyl]phenyl]-5-fluor-l,3-dimethyl-pyrazol-4-carboxamid, (2.039) 3-(Difhiormethyl)-N-methoxy-l-methyl-N-[(lS)-l-methyl-2-(2,4,6-trichlorphenyl)ethyl]pyra- zol-4-carboxamid, (2.040) 3-(Difhiormethyl)-N-methoxy-l-methyl-N-[(lR)-l-methyl-2-(2,4,6-tri- chlorphenyl)ethyl]pyrazol-4-carboxamid, (2.041) N-[2-[(lS)-l,3-Dimethylbutyl]-3-thienyl]-l-methyl- 3 -(trifluormethyl)pyrazol-4-carboxamid, (2.042) N-[2- [(1 R)- 1 ,3-Dimethy Ibutyl] -3 -thienyl] - 1 -methy 1- 3-(trifluormethyl)pyrazol-4-carboxamid, (2.043) N-[rac-(lS,2S)-2-(2,4-Dichlor-phenyl)cyclobutyl]-2- (trifluormethy l)nicotinamid, (2.044) 2-(Difluormethy 1) -N -(3 -ethyl- 1 , 1 -dimethy l-indan-4-y l)py ridin-3 - carboxamid.

[0359] 3) Inhibitoren der Atmungskette am Komplex III, beispielsweise (3.001) Ametoctradin, (3.002) Ami- sulbrom, (3.003) Azoxystrobin, (3.004) Coumethoxystrobin, (3.005) Coumoxystrobin, (3.006) Cyazofa- mid, (3.007) Dimoxystrobin, (3.008) Enoxastrobin, (3.009) Famoxadon, (3.010) Fenamidon, (3.011) Fenpicoxamid, (3.012) Florylpicoxamid, (3.013) Flufenoxystrobin, (3.014) Fluoxastrobin, (3.015) Kre- soxim-methyl, (3.016) Mandestrobin, (3.017) Metarylpicoxamid, (3.018) Metominostrobin, (3.019) Metyltetraprol, (3.020) Orysastrobin, (3.021) Picoxystrobin, (3.022) Pyraclostrobin, (3.023) Pyrame- tostrobin, (3.024) Pyraoxystrobin, (3.025) Pyribencarb, (3.026) Trifloxystrobin, (3.027) (2E)-2-{2- [({[(lE)-l-(3-{[(E)-l-fluor-2-phenylvinyl]oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2- (methoxyimino)-N-methylacetamid, (3.028) (2E,3Z)-5-{[l-(4-Chlor-2-fluorphenyl)-lH-pyrazol-3- yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamid, (3.029) (2E,3Z)-5-{[l-(4-Chlorphenyl)-lH- pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamid, (3.030) (2R)-2-{2-[(2,5-Di- methylphenoxy)methyl]phenyl}-2 -methoxy -N-methylacetamid, (3.031) (2S)-2-{2-[(2,5-Dimethylphe- noxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.032) (Z,2E)-5-[l-(2,4-Dichlorphenyl)pyrazol-.

[0360] 3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enamid, (3.033) (Z)-2-(5-Cyclohexyl-2-methylphe- noxy)-3-methoxyprop-2-ensäuremethylester, (3.034) (Z)-2-(5-Cyclopentyl-2-methylphenoxy)-3- methoxyprop-2-ensäuremethylester, (3.035) (Z)-3 -Methoxy -2-[2-methy 1-5 -(3 -propy Ipyrazol- 1 -y l)phe- noxy]prop-2-ensäuremethylester, (3.036) (Z)-3-Methoxy-2-[2-methyl-5-[3-(trifluormethyl)pyrazol-l- yl]phenoxy]prop-2-ensäuremethylester, (3.037) (Z)-2-[5-(3-Isopropyl-pyrazol-l-yl)-2-methyl-phe- noxy] -3 -methoxy -prop-2 -ensäureethy tester, (3.038) {5-[3-(2,4-Dimethylphenyl)-lH-pyrazol-l-yl]-2- methylbenzyl}carbamidsäuremethylester, (3.039) (2E)-2-Methoxyimino-N-methyl-2-[3-methyl-2- [[(E)-l-[3-(trifluormethyl)phenyl]ethylideneamino]oxy-methyl]phenyl]-acetamid, (3.040) (2E)-2-[2- [[(E)-l-(3,5-Difluorphenyl)ethylideneamino]oxymethyl]-3-methyl-phenyl] -2-methoxy-imino-N- methyl-acetamid, (3.041) (2S)-2-[(3-Hydroxy-4-methoxypyridin-2-carbonyl)amino]-propansäure[rac- 2-(4-brom-7-fluorindol-l-yl)-l-methylpropyl]ester, (3.042) (2S)-2-[(3-Acetoxy-4-methoxypyridin-2- carbonyl)amino]propansäure[rac-2-(7-brom-4-fluorindol-l-yl)-l-methylpropyl]-ester, (3.043) (2S)-2- [(3-Hydroxy-4-methoxypyridin-2-carbonyl)amino]propansäure-[rac-2-(7-bromindol-l-yl)-l-methyl- propyl]ester, (3.044) (2S)-2-[(3-Hydroxy-4-methoxypyridin-2-carbonyl)-amino]-propansäure[rac-2- (3,5-dichlor-2-pyridyl)-l-methylpropyl]-ester, (3.045) (2S)-2-[(3-Acetoxy-4-methoxypyridin-2-carbo- nyl)amino]propansäure- [(1 S)- 1 - [ 1 -(1 -naphthyl)cyclopropy 1] -ethyl] -ester, (3.046) (2S)-2- [(3 -Hydroxy -.

[0361] 4-methoxypyridin-2-carbonyl)amino]propansäure[(lS)-l-[l-(l-naphthyl)cyclo-propyl]-ethyl]ester, (3.047) (2S)-2-[[3-(Acetoxymethoxy)-4-methoxypyridin-2-carbonyl]amino]-propan-säure[(lS)-l-[l- (l-naphthyl)cyclopropyl] -ethyl] ester, (3.048) 2-Methyl-propansäure-[2-[[(lS)-2-[(lRS,2SR)-2-(3,5-di- chlor-2 -pyridyl)- 1 -methylpropoxy] - 1 -methy 1-2 -oxo-ethyl] -carbamoyl] -4-methoxy-3-py- ridyl]oxy -methylester, (3.049) 2-[Cyan-(2,6-difluor-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5- methyl-thiazol-4-carboxamid, (3.050) 2-[Cyan-(2,6-difluor-4-pyridyl)amino]-5-methyl-N- spiro[3.4]octan-3-yl-thiazol-4-carboxamid, (3.051) 2-[Cyan-(2,6-difluor-4-pyridyl)amino]-N-hexyl-5- methyl-thiazol-4-carboxamid, (3.052) 2-[Acetyl-(2,6-difluor-4-pyridyl)amino]-N-(2,2-dimethyl-cyclo- butyl)-5-methyl-thiazol-4-carboxamid, (3.053) 2-[(2,6-Difluor-4-pyridyl)-(2-methylpropa- noyl)-amino] -N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamid, (3.054) 2-[(2,6-Difluor-4- pyridyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamid, (3.055) 2-[(2,6-Difluor-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5- methyl-N-(tetrahydrofuran-3-carbonyl)thiazol-4-carboxamid, (3.056) 2-[(2,6-Difluor-4-pyridyl)-(tetra- hydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamid, (3.057) 2- [(2,6-Difluor-4-pyridyl)-(oxetan-3-carbonyl)amino]-N-(2,2-dimethyl-cyclobutyl)-5-methyl-thiazol-4- carboxamid, (3.058) 2-[(2,6-Difluor-4-pyridyl)-(tetrahydro-pyran-4-carbonyl)amino]-N-(2,2-dimethyl- cyclobutyl)-5-methyl-thiazol-4-carboxamid, (3.059) N-(3-Ethyl-3,5,5-trimethylcyclohexyl)-3-for- mamido-2-hydroxy-benzamid.

[0362] 4) Inhibitoren der Mitose und Zellteilung, beispielsweise (4.001) Carbendazim, (4.002) Diethofencarb, (4.003) Ethaboxam, (4.004) Fluopicolid, (4.005) Fluopimomid, (4.006) Metrafenon, (4.007) Pency- curon, (4.008) Pyridachlometyl, (4.009) Pyriofenon (Chlazafenon), (4.010) Thiabendazol, (4.011) Thio- phanat-methyl, (4.012) Zoxamid, (4.013) 3-Chlor-5-(4-chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpy- ridazin, (4.014) 3-Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4-(2,4,6-trifluorphenyl)pyridazin, (4.015) 4- (2-Brom-4-fluorphenyl)-N-(2,6-difluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.016) 4-(2-Brom-4- fluorphenyl)-N-(2-brom-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.017) 4-(2-Brom-4- fluorphenyl)-N -(2-brompheny 1)- 1 ,3 -dimethyl- 1 H-pyrazol-5 -amin, (4.018) 4-(2-Brom-4-fluorphenyl)- N-(2-chlor-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.019) 4-(2-Brom-4-fluorphenyl)-N-(2- chlorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.020) 4-(2-Brom-4-fluorphenyl)-N-(2-fluorphenyl)- l,3-dimethyl-lH-pyrazol-5-amin, (4.021) 4-(2-Chlor-4-fluorphenyl)-N-(2,6-difluorphenyl)-l,3-di- methyl-lH-pyrazol-5-amin, (4.022) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)-l,3-di- methyl-lH-pyrazol-5-amin, (4.023) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlorphenyl)-l,3-dimethyl-lH-py- razol-5-amin, (4.024) 4-(2-Chlor-4-fluorphenyl)-N-(2-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.025) 4-(4-Chlorphenyl)-5-(2,6-difluorphenyl)-3,6-dimethylpyridazin, (4.026) N-(2-Brom-6- fluorphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.027) N-(2-Bromphenyl)- 4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.028) N-(4-Chlor-2,6-difluorphenyl)-4- (2-chlor-4-fluorpheny 1)- 1 ,3-dimethyl- 1 H-pyrazol-5 -amin.

[0363] 5) Compounds capable of multisite action, for example (5.001) Bordeaux mixture, (5.002) Captafol, (5.003) Captan, (5.004) Chlorothalonil, (5.005) Copper hydroxide, (5.006) Copper maphthenate, (5.007) Copper oxide, (5.008) Copper oxychloride, (5.009) Copper(II) sulfate, (5.010) Dithianon, (5.011) Dodine, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, (5.016) Metiram 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][l,4]dithiino[2,3-c][l,2]thiazole-3-carbonitrile.

[0364] 6) Compounds capable of triggering host defense, for example (6.001) acibenzo-lar-S-methyl, (6.002) fosetyl aluminum, (6.003) fosetyl calcium, (6.004) fosetyl sodium, (6.005) isotianil, (6.006) phosphorous acid and its salts, (6.007) probenazol, (6.008) tiadinil.

[0365] 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.

[0366] 8) Inhibitors of ATP production, for example (8.001) Silthiofam.

[0367] 9) Inhibitors of cell wall synthesis, 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.

[0368] 10) Inhibitoren der Lipid-Synthese oder des Lipid-Transports oder der Membran-Synthese, beispielsweise (10.001) Fluoxapiprolin, (10.002) Natamycin, (10.003) Oxathiapiprolin, (10.004) Propamo- carb, (10.005) Propamocarb-hydrochlorid, (10.006) Propamocarb-fosetylat, (10.007) Tolclofos-methyl, (10.008) l-(4-{4-[(5R)-5-(2,6-Difluorphenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin- l-yl)-2-[5-methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]ethanon, (10.009) l-(4-{4-[(5S)-5-(2,6-Di- fluorphenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluor- methyl)- lH-pyrazol-l-yl]ethanon, (10.010) 2-{(5R)-3-[2-(l-{[3,5-Bis(difluor-methyl)-lH-pyrazol-l- yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorphenylmethansulfo- nate, (10.011) 2-{(5S)-3-[2-(l-{[3,5-bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3- thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorphenyl-methan-sulfonate, (10.012) 3-[2-(l -{ [5- methy 1-3 -(trifluormethyl)- 1 H-pyrazol- 1 -yl] acety l}piperidin-4-yl)- 1 ,3-thiazol-4-yl] - 1 ,5 -dihy dro-2,4- benzodioxepin-6-ylmethansulfonat, (10.013) 9-Fluor-3-[2-(l-{[5-methyl-3-(trifluormethyl)-lH-pyra- zol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-l,5-dihydro-2,4-benzodioxepin-6-ylmethan-sulfonat, (10.014) 3-[2-(l-{[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]- 1,5 -dihy dro-2,4-benzodioxepin-6-ylmethansulfonat, (10.015) 3-[2-(l-{[3,5-Bis(difhiormethyl)-lH-py- razol- 1 -yl] acety l}piperidin-4-y 1)- 1 ,3-thiazol-4-yl] -9-fluor- 1 ,5 -dihy dro-2,4-benzodioxepin-6-ylmethan- sulfonat. 11) Inhibitoren der Melanin-Biosynthese, beispielsweise (11.001) Tolprocarb, (11.002) Tricyclazol.

[0369] 12) Inhibitoren der Nukleinsäure-Synthese, beispielsweise (12.001) Benalaxyl, (12.002) Benalaxyl-M (Kiralaxyl), (12.003) Metalaxyl, (12.004) Metalaxyl-M (Mefenoxam).

[0370] 13) Inhibitors of signal transduction, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozoline.

[0371] 14) Compounds that can act as uncouplers, for example (14.001) Fluazinam, (14.002) Meptyldinocap.

[0372] 15) Other compounds, for example (15.001) abscisic acid, (15.002) aminopyrifene, (15.003)

[0373] Benthiazol, (15.004) Bethoxazin, (15.005) Capsimycin, (15.006) Carvon, (15.007) Chinomethionat, (15.008) Chlorinconazid, (15.009) Cufraneb, (15.010) Cyflufenamid, (15.011) Cymoxanil, (15.012) Cy- prosulfamid, (15.013) Dipymetitron, (15.014) D-Tagatose, (15.015) Feneptamidoquin, (15.016) Flufe- noxadiazam, (15.017) Flumetylsulforim, (15.018) Flutianil, (15.019) Ipflufenoquin, (15.020) Methyli- sothiocyanat, (15.021) Mildiomycin, (15.022) Nickeldimethyldithiocarbamat, (15.023) Nitrothal-iso- propyl, (15.024) Oxyfenthiin, (15.025) Pentachlorphenol und Salze, (15.026) Picarbutrazox, (15.027) Quinofumelin, (15.028) Tebufloquin, (15.029) Tecloftalam, (15.030) Tolnifanid, (15.031) 2-(6-Benzyl- pyridin-2-yl)chinazolin, (15.032) 2-[6-(3-Fluor-4-methoxyphenyl)-5-methylpyridin-2-yl]chinazolin, (15.033) 2-Phenylphenol und Salze, (15.034) 4-Amino-5-fluorpyrimidin-2-ol (tautomere Form: 4- Amino-5-fluorpyrimidin-2(lH)-on), (15.035) 4-Oxo-4-[(2-phenylethyl)amino]butansäure, (15.036) 5- Amino-l,3,4-thiadiazol-2-thiol, (15.037) 5-Chlor-N'-phenyl-N'-(prop-2-in-l-yl)thiophen-2-sulfonohy- drazid, (15.038) 5-Fluor-2-[(4-fluorbenzyl)-oxy]pyrimidin-4-amin, (15.039) 5-Fluor-2-[(4-methylben- zyl)oxy]-pyrimidin-4-amin, (15.040) {6-[({ [(Z)-(l -Methyl- lH-tetrazol-5-y l)(phenyl)methy- len]-amino}-oxy)methyl]pyridin-2-yl}carbamid-säure-but-3-in-l-ylester, (15.041) (2Z)-3-Amino-2- cyano-3-phenylacrylsäureethylester, (15.042) 2-[Acetyl-[2-ethylsulfonyl-4-(trifluormethyl)ben- zoyl] amino] -5 -(trifluormethoxy)benzoesäuremethylester, (15.043) N-Acety l-N-[2-bromo-4-(trifluor- methoxy)phenyl]-2-ethylsulfonyl-4-(trifluormethyl)-benzamid, (15.044) Phenazin- 1 -carbonsäure, (15.045) 3,4,5-Trihydroxybenzoesäurepropylester, (15.046) Chinolin-8-ol, (15.047) Chinolin-8-ol-sul- fat (2:1), (15.048) (2R)-2-Benzyl-N-(8-fluor-2-methyl-3-chinolyl)-2,4-dimethylpentanamid, (15.049) (2S)-2-Benzyl-N-(8-fluor-2-methyl-3-chinolyl)-2,4-dimethylpentanamid, (15.050) l-(4,5-Dimethyl- lH-benzimidazol-l-yl)-4,4-difluor-3,3-dimethyl-3,4-dihydroisochinolin, (15.051) l-(4,5-Di- methyl-benzimidazol-l-yl)-4,4,5-trifluor-3,3-dimethyl-isochinolin, (15.052) l-(5-(Fluormethyl)-6- methyl-pyridin-3-yl)-4,4-difluor-3,3-dimethyl-3,4-dihydro-isochinolin, (15.053) l-(5,6-Dimethylpyri- din-3-yl)-4,4-difluor-3,3-dimethyl-3,4-dihydroisochinolin, (15.054) l-(6-(Difluormethyl)-5- methoxypyridin-3-yl)-4,4-difluor-3,3-dimethyl-3,4-dihydro-isochinolin, (15.055) l-(6-(Difluor- methyl)-5-methyl-pyridin-3-yl)-4,4-difluor-3,3-dimethyl-3,4-dihydro-isochinolin, (15.056) 4,4-Di- fluor-3,3-dimethyl-l-(7-methylpyrazolo[l,5-a]pyridin-3-yl)-isochinolin, (15.057) l-(6,7-Dimethylpy- razolo[l,5-a]pyridin-3-yl)-4,4,5-trifluor-3,3-dimethyl-isochinolin, (15.058) l-(6,7-Dimethylpyra- zolo[l,5-a]pyridin-3-yl)-4,4-difluor-3,3-dimethyl-3,4-dihydroisochinolin, (15.059) 2-{2-Fluor-6-[(8- fluor-2-methylchinolin-3-yl)oxy]phenyl}propan-2-ol, (15.060) 3-(4,4,5-Trifluor-3,3-dimethyl-3,4-di- hydroisochinolin- 1 -yl)chinolin, (15.061) 3 -(4,4-Difluor-3,3 -dimethy 1-3 ,4-dihy droisochinolin- 1 -yl)-8- fluorchinolin, (15.062) 3-(4,4-Difluor-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)chinolin, (15.063) 3-(5-Fluor-3,3,4,4-tetramethyl-3,4-dihydro-isochinolin-l-yl)chinolin, (15.064) 4,4-Difluor-.

[0374] 3.3-dimethyl-l-(4-methylbenzimidazol-l-yl)-isochinolin, (15.065) 4,4-Difluor-3,3-dimethyl-l-(6- methylpyrazolo[l,5-a]pyridin-3-yl)isochinolin, (15.066) 5-Brom-l-(5,6-dimethylpyridin-3-yl)-3,3-di- methy 1-3, 4-dihy droisochinolin, (15.067) 7, 8-Difluor-N-[rac-l -benzyl- 1, 3 -dimethylbutyl] chinolin-3- carboxamid, (15.068) 8-Fluor-3-(5-fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-l-yl)chinolin, (15.069) 8-Fluor-3-(5-fluor-3,3-dimethyl-3,4-dihydroisochinolin-l-yl)chinolin, (15.070) 8-Fluor-N- (4,4,4-trifluor-2-methyl-l-phenylbutan-2-yl)chinolin-3-carboxamid, (15.071) 8-Fhior-N-[(lR)-l-[(3- fluor-phenyl)-methyl]-l,3-dimethylbutyl]-chinolin-3-carboxamid, (15.072) 8-Fluor-N-[(lS)-l-[(3- fluorphenyl)-methyl]-l,3-dimethylbutyl]-chinolin-3-carboxamid, (15.073) 8-Fluor-N-[(2S)-4,4,4-tri- fluor-2-methyl-l-phenylbutan-2-yl]chinolin-3-carboxamid, (15.074) 8-Fluor-N-[rac-l-[(3- fluorpheny l)methyl] -1,3 -dimethy Ibuty l]chinolin-3-carboxamid, (15.075) 9-Fluor-2,2-dimethyl-5 -(chi- nolin-3-yl)-2,3-dihydro-l,4-benzoxazepin, (15.076) N-(2,4-Dimethyl-l-phenylpentan-2-yl)-8-fluorchi- nolin-3 -carboxamid, (15.077) N-[(1R)-1 -Benzyl- 1 ,3 -dimethy Ibuty 1] -7, 8-difluorchinolin-3 -carboxamid, (15.078) N-[(lS)-l-Benzyl-l,3-dimethylbutyl]-7,8-difluorchuinolin-3-carboxamid, (15.079) N-[(2S)-.

[0375] 2.4-Dimethyl-l-phenylpentan-2-yl]-8-fluorquinolin-3 -carboxamid, (15.080) rac-2-Benzyl-N-(8-fluor- 2-methyl-3-chinolyl)-2,4-dimethylpentanamid, (15.081) (5RS)-3-[3-(3-Cyclopropyl-2-fluorphenoxy)- 6-methyl-pyridazin-4-yl]-5-(2,4-dimethyl-benzyl)-5,6-dihydro-4H-l,2,4-oxadiazin, (15.082) (5S)-3-[3- (3-Cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-

[0376] 1.2.4-oxadiazin, (15.083) (5RS)-5-(4-Brom-2-methylbenzyl)-3-[3-(3-chlor-2-fluorphenoxy)-6- methyl-pyridazin-4-yl]-5,6-dihydro-4H-l,2,4-oxadiazin, (15.084) (5RS)-3-[3-(3-Chlor-2-fluorphe- noxy)-6-methylpyridazin-4-yl]-5-(2-chlor-4-methylbenzyl)-5,6-dihydro-4H-l,2,4-oxadiazin, (15.085) (5 S)-5-(4-Brom-2-methylbenzyl)-3-[3-(3-chlor-2-fluorphenoxy)-6-methyl-pyridazin-4-yl]-5,6-dihy- dro-4H- 1 ,2,4-oxadiazin, (15.086) (5R)-3- [3 -(3 -Chlor-2-fluorphenoxy)-6-methy lpyridazin-4-yl] -5 -(2- chlor-4-methylbenzyl)-5,6-dihydro-4H-l,2,4-oxadiazin, (15.087) (5S)-3-[3-(3-Chlor-2-fluorphenoxy)- 6-methylpyridazin-4-yl]-5-(2-chlor-4-methylbenzyl)-5,6-dihydro-4H-l,2,4-oxadiazin, (15.088) 6-

[0377] Chlor-3-(3-cyclopropyl-2-fluorphenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluorethyl]-5-methylpyrida- zin-4-carboxamid, (15.089) 3-(3-Brom-2-fluor-phenoxy)-6-chlor-N-[2-(2-chlor-4-methylphenyl)-2,2- difluorethy 1] -5-methylpyridazin-4-carboxamid, ( 15.090) 6-Chlor-N- [2-(2-chlor-4-methylpheny l)-2,2- difluorethyl]-3-(3-cyclopropyl-2-fluorphenoxy)-5-methylpyridazin-4-carboxamid, (15.091) 6-Chlor-3- (3-cyclopropyl-2-fluorphenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluorethyl]-5-methylpyridazin-4- carboxamid, (15.092) 6-Chlor-3 -(3 -chlor-2-fluorphenoxy)-N- [2-(2,4-dimethy lphenyl)-2,2-di- fluor-ethyl]-5-methylpyridazin-4-carboxamid, (15.093) N-[2-(2-Brom-4-methylphenyl)-2,2-difluo- rethyl]-6-chlor-3-(3-cyclopropyl-2-fluorphenoxy)-5-methylpyridazin-4-carboxamid, (15.094) 1,1-

[0378] Diethyl-3-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-hamstoff, (15.095) 1,3-Di- methoxy- 1 -[ [4- [5-(trifluormethy 1)- 1 ,2,4-oxadiazol-3-y l]pheny 1] -methyl] -hamstoff, ( 15.096) 1 - [[3 -

[0379] Fluor-4-(5-(trifluormethyl)-l,2,4-oxadiazol-3-yl)phenyl]-methyl]azepan-2-on, (15.097) l-[[4-[5-(Tri- fluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-on, (15.098) l-Methoxy-l-methyl-3-[[4- [5 -(trifluormethyl) - 1 ,2,4-oxadiazol-3 -y 1] phenyl] -methyl] -harnstoff, (15.099) 1 -Methoxy -3 -methyl- 1 - [[4- [5 -(trifluormethyl)- 1 ,2,4-oxadiazol-3-yl]pheny 1] -methyl] -hamstoff, (15.100) 2-(Difluormethy l)-5 - [2-[l-(2,6-difluorphenyl)cyclopropoxy]pyrimidin-5-yl]-l,3,4-oxadiazol, (15.101) 2,2-Difluor-N- methyl-2-[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]-acetamid, (15.102) 3,3-Dimethyl-l-[[4- [5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]-methyl]piperidin-2-on, (15.103) 3-Ethyl-l-methoxy- l-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]hamstoff, (15.104) 4,4-Dimethyl-l-[[4- [5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-on, (15.105) 4,4-Dimethyl-2-[[4- [5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-on, (15.106) Dimethylcarba- mid-säure-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenylester, (15.107) 5,5-Dimethyl-2-[[4-[5-(tri- fluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-on, (15.108) 5-[5-(Difluormethyl)- 1 ,3 ,4-oxadiazol-2-y 1] -N- [(1 R)- 1 -(2,6-difluorpheny l)ethy l]pyrimidin-2-amin, (15.109) 5 -[5 -(Difluor- methyl)-!, 3, 4-oxadiazol-2-yl]-N-[(lR)-l-(2,6-difluorphenyl)propyl]pyrimidin-2-amin, (15.110) 5-[5- (Difluormethyl)-l,3,4-oxadiazol-2-yl]-N-[(lR)-l-(2-fluorphenyl)ethyl]-pyrimidin-2-amin, (15.111) 5- [5-(Difluormethyl)-l,3,4-oxadiazol-2-yl]-N-[(lR)-l-(2-fluorphenyl)-ethyl]pyrimidin-2-amin, (15.112) 5 -[5 -(Difluormethy 1)- 1 ,3 ,4-oxadiazol-2-y 1] -N-[( 1R)- 1 -(3 ,5 -difluor-pheny l)-ethy 1] -pyrimidin-2-amin,.

[0380] (15.113) 5-[5-(Difluormethyl)-l,3,4-oxadiazol-2-yl]-N-[(lR)-l-phenylethyl]-pyrimidin-2-amin,

[0381] (15.114) 5-[5-(Difluormethyl)-l,3,4-oxadiazol-2-yl]-N-[l-(2-fluorphenyl)cyclo-propyl]pyrimidin-2- amin, (15.115) 5-Methyl-l-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2- on, (15.116) l-{4-[5-(Trifluor-methyl)-l,2,4-oxadiazol-3-yl]benzyl}-lH-pyrazol-4-carbonsäu- reethylester, (15.117) {4-[5-Trifluor-methyl)-l,2,4-oxadiazol-3-yl]phenyl}-carbamid-säuremethylester, (15.118) N-(l-Methylcyclopropyl)-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.119) N- (2,4-Difluorphenyl)-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.120) N-(2-Dimethoxy)- N-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]-methyl]-propanamid, (15.121) N,N-Dimethyl- l-{4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzyl}-lH-l,2,4-triazol-3-amin, (15.122) N-[(E)-

[0382] Methoxyiminomethyl]-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.123) N-[(E)-N-

[0383] Methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.124) N- [(Z)-Methoxyiminomethyl]-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.125) N-[(Z)-N- Methoxy-C-methylcarbonimidoyl]-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.126) N- [[2,3-Difluor-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluorpropanamid, (15.127) N-[[4-[5-(Trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamid, (15.128) N-[4-[5- (Trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]cyclo-propan-carboxamid, (15.129) N-{2,3-Difluor-4- [5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzyl}-butan-amid, (15.130) N-{4-[5-(Trifluormethyl)-l,2,4- oxadiazol-3-yl]benzyl}cyclopropancarboxamid, (15.131) N-{4-[5-(Trifluormethyl)-l,2,4-oxadiazol-3- yl]phenyl}propanamid, (15.132) N-Allyl-N-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3- yl]phenyl]-methyl]acetamid, (15.133) N-Allyl-N-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]-propanamid, (15.134) N-Ethyl-2-methyl-N-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol- 3 -yl]phenyl] -methyl] -propanamid, (15.135) N-Methoxy-N-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3- y l]pheny 1] -methyl] -cy clopropancarboxamid, (15.136) N-Methy 1-4 - [5 -(trifluormethyl)- 1 ,2,4-oxadiazol- 3-yl]benzamid, (15.137) N-Methyl-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzolcarbothioamid, (15.138) N-Methyl-N-phenyl-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.139) 2,2-Di- fluor-2-[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]-essigsäure, (15.140) l-[[4-[(Z)-2 -Ethoxy - 3,3,3-trifluor-prop-l-enoxy]phenyl]methyl]pyrazol-4-carbonsäure-ethyl-ester, (15.141) l-[[4-[[2-(Tri- fluormethyl)-l,3-dioxolan-2-yl]methoxy]phenyl]-methyl]pyrazol-4- carbonsäure-ethyl-ester, (15.142) N-(2,2,2-Trifluorethyl)-2-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]oxazol-4-car- boxamid, (15.143) N-[(2S)-l-{3-[(2RS)-2-(5-Fhior-2-methoxyphenyl)-2 -hydroxyethyl]-5-[(lE)-N -isopropoxy ethanimidoyl]-2, 6-dioxo-3,6-dihydro-pyrimidin-l(2H)-yl}propan-2-yl] -2 -methyl-propanamid,.

[0384] (15.144) N-[(2S)-l-{3-[2-(5-Fhior-2-methoxy-phenyl)-2-hydroxyethyl]-5-[(lE)-N-isopropoxyethani- midoyl]-2,6-dioxo-3,6-dihydropyrimidin-l(2H)-yl}-3-methylbutan-2-yl]-2-methylpropanamid,

[0385] (15.145) N-[(2S)-l-{3-[2-(5-Fluor-2-methoxyphenyl)-2-hydroxyethyl]-5-[(lE)-N-isopropoxyethani- midoyl]-2,6-dioxo-3,6-dihydropyrimidin-l(2H)-yl}-3-methyl-butan-2-yl]-2,2-dimethylpropanamid,

[0386] (15.146) N-[(2S)-l-{3-[2-Hydroxy-2-(2-methoxyphenyl)-ethyl]-5-[(lE)-N-isopropoxyethanimidoyl]-

[0387] 2.6-dioxo-3,6-dihydropyrimidin-l(2H)-yl}propan-2-yl]-2-methyl-propanamid, (15.147) N-[(2S)-l-{3- [2-(2-Cyanethoxy)-2-(5-fluor-2-methoxyphenyl)ethyl]-5-[(lE)-N-isopropoxyethanimidoyl]-2,6-dioxo-

[0388] 3.6-dihydropyrimidin-l(2H)-yl}propan-2-yl]-2 -methyl-propanamide, (15,148) N-[(2S)-l-{3-[(2R)-2-(5- Fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(1E)-N-isopropoxyethanimidoyl]-2,6-dioxo-3,6-dihydro-pyrimidin-l(2H)-yl}propan-2-yl]-2 -methylpropanamide, (15.149) N-[(2S)-l-{3-[(2R)-2-(5-fluoro-2- methoxyphenyl)-2-hydroxyethyl]-5-[(1E)-N-isopropoxy-ethanimidoyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl} -3 -methy lbutan-2-y 1] -2-methyl-propanamide.

[0389] Biological pesticides as mixture components

[0390] The compounds of formula (I) can be combined with biological pesticides. Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and products formed by microorganisms, including proteins and secondary metabolites.

[0391] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria, and bacteria that act as biological insecticides, fungicides, or nematicides.

[0392] Examples of such bacteria that are used or can be used as biological pesticides are:

[0393] Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, in particular strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, in particular strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or thuringiensis subsp. aizawai, especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Methylorubrum extorquens TS201, Pasteuri a penetrans, Pasteuria spp.(Rotylenchulus reniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (Acession Number NRRL 30232).

[0394] Examples of fungi and yeasts that are used or can be used as biological pesticides include:

[0395] Beauveria bassiana, in particular strain ATCC 74040, Coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., in particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metchnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89 / 030550), Talaromyces flavus, especially strain VI 17b, Trichoderma atroviride, especially strain SCI (Accession Number CBS 122089), Trichoderma harzianum, especially T. harzianum rifai T39. (Accession Number CNCM 1-952).

[0396] Examples of viruses that are used or can be used as biological pesticides include:

[0397] Adoxophyes orana (apple peel moth) Granulose virus (GV), Cydia pomonella (cobble moth) Granulose virus (GV), Helicoverpa armigera (cotton bollworm) Nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet moth) mNPV, Spodoptera frugiperda (army worm) mNPV, Spodoptera littoralis (African cotton bollworm) NPV.

[0398] This also includes bacteria and fungi that are added to plants, plant parts, or plant organs as 'inoculators' and promote plant growth and health through their special properties. Examples include:

[0399] Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especially Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.

[0400] Examples of plant extracts and products formed by microorganisms, including proteins and secondary metabolites, that are or can be used as biological pesticides are:

[0401] Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, “Requiem ™ Insecticide”, Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dio-ica, Veratrin, Viscum album, Brassicacaeen extract, especially rapeseed or mustard powder, as well as those obtained from olive oil bioinsecticidal / acaricidal active ingredients, in particular unsaturated fatty / carboxylic acids with carbon chain lengths of C16-C20 as active ingredients, such as those contained in the product with the trade name FLiPPER®.

[0402] Safeners as Mixture Components The compounds of formula (I) can be combined with safeners such as benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormide, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalene 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).

[0403] Plants and plant parts

[0404] According to the invention, all plants and plant parts can be treated. Here, "plants" refers to all plants and plant populations, such as desirable and undesirable wild plants or cultivated plants (including naturally occurring cultivated plants), for example, cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans, Brassica oleracea (e.g., cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes).Cultivated plants can be plants that can be obtained through conventional breeding and optimization methods, or through biotechnological and genetic engineering methods, or combinations thereof, including transgenic plants and plant varieties that are or are not protected by plant variety rights. The term "plant" encompasses all stages of development, from seeds and cuttings to young (immature) plants and mature plants. "Plant parts" refers to all above-ground and below-ground parts and organs of plants, such as shoots, leaves, flowers, and roots, with examples including leaves, needles, stems, trunks, flowers, fruiting bodies, fruits, and seeds, as well as roots, tubers, and rhizomes.Plant parts also include harvested plants or harvested plant parts, as well as vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.

[0405] The treatment of plants and plant parts according to the invention with the compounds of formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage space according to the usual treatment methods, e.g. by immersion, spraying, evaporation, fogging, scattering, spreading, injection and, in the case of propagation material, especially seeds, furthermore by single- or multi-layer coating.

[0406] As mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild-occurring plant species and varieties, as well as those obtained through conventional biological breeding methods such as crossbreeding or protoplast fusion, are treated. In another preferred embodiment, transgenic plants and varieties obtained through genetic engineering, optionally in combination with conventional methods (genetically modified organisms), and their parts are treated. The terms "parts" or "parts of plants" or "plant parts" have been explained above. Plants of commercially available or currently used varieties are particularly preferred according to the invention. Plant varieties are understood to be plants with new traits obtained through conventional breeding, mutagenesis, or recombinant DNA techniques.These can be varieties, breeds, biotypes and genotypes.

[0407] Transgenic plant, seed treatment and integration events

[0408] According to the invention, the compounds of formula (I) can be advantageously used to treat transgenic plants, plant cultivars, or plant parts that have received genetic material that confers advantageous and / or useful traits upon these plants, plant cultivars, or plant parts. It is therefore considered to combine the present invention with one or more recombinant traits or transgenic events, or a combination thereof. For the purposes of the present application, a transgenic event occurs through the insertion of a specific recombinant DNA molecule into a specific position (locus) in the chromosome of the plant genome.The insertion creates a new DNA sequence, referred to as an "event," characterized by the inserted recombinant DNA molecule and a certain amount of genomic DNA immediately adjacent to / flanking the inserted DNA at both ends. Such traits or transgenic events include, but are not limited to, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutrient quality, hybrid seed production, and herbicide tolerance, with the trait being measured in relation to a plant lacking such a trait or transgenic event.Specific examples of such advantageous and / or useful traits include improved plant growth, vigor, stress tolerance, stability, resistance to lodging, nutrient uptake, plant nutrition and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salinity, increased flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and / or higher nutritional value of the harvested products, better shelf life and / or workability of the harvested products and increased resistance or tolerance to animal and microbial pests such as insects, arachnids, nematodes, mites and slugs.Of the DNA sequences encoding proteins that confer resistance or tolerance properties to such animal and microbial pests, especially insects, the genetic material of Bacillus thuringiensis, which encodes the Bt proteins, should be mentioned in detail. These proteins are extensively described in the literature and well known to those skilled in the art. Also worth mentioning are proteins extracted from bacteria such as Photorhabdus (WO97 / 17432 and WO98 / 08932). In particular, mention should be made of Bt-Cry or VIP proteins, including CrylA, CrylAb, CrylAc, CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF proteins or toxic fragments thereof, and also hybrids or combinations thereof, especially the CrylF protein or hybrids derived from a CrylF protein (e.g.Hybrid CrylA-CryIF proteins or toxic fragments thereof), the CrylA-type proteins or toxic fragments thereof, preferably the CrylAc protein or hybrids derived from the CrylAc protein (e.g., hybrid CrylAb-CrylAc proteins), or the CrylAb or Bt2 protein or toxic fragments thereof, the Cry2Ae, Cry2Af, or Cry2Ag proteins or toxic fragments thereof, the CrylA.105 protein or a toxic fragment thereof, the VIP3Aal9 protein, the VIP3Aa20 protein, the VIP3A proteins produced at the COT202 or COT203 cotton events, the VIP3Aa protein or a toxic fragment thereof, as described in Estruch et al. (1996), Proc Natl Acad Sei US A. 28;93(11):5389-94, described the Cry proteins as described in WO2001 / 47952, the insecticidal proteins from Xenorhabdus (as described in WO98 / 50427), Serratia (especially from S. entomophila) or strands of the Photorhabdus species, such as Tc proteins from Photorhabdus, as described in WO98 / 08932.This also includes all variants or mutants of any of these proteins which differ in some amino acids (1-10, preferably 1-5) from any of the sequences listed above, in particular the sequence of their toxic fragment, or which are fused to a transit peptide such as a plastid transit peptide or another protein or peptide.

[0409] Another, and particularly noteworthy, example of such properties is conferred tolerance to one or more herbicides, for example, imidazolinones, sulfonylhams, glyphosate, or phospinothricin. Of the DNA sequences encoding proteins that confer tolerance properties to specific herbicides in transformed plant cells and plants, particular mention should be made of the bar or PAT gene, or the Streptomyces coelicolor gene described in W02009 / 152359, which confers tolerance to glufonsin herbicides; a gene encoding a suitable EPSPS (5-enolpyruvylshikimate-3-phosphate enzyme aminotransferase), which confers tolerance to herbicides targeting EPSPS, especially herbicides such as glyphosate and its salts; a gene encoding glyphosate N-acetyltransferase; or a gene encoding glyphosate oxoreductase.Other suitable herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g., W02007 / 024782), a mutated Arabidopsis ALS / AHAS gene (e.g., US Patent 6,855,533), genes encoding 2,4-D-monooxygenases that confer tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid), and genes encoding dicamba-monooxygenases that confer tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid).

[0410] Other and particularly highlighted examples of such properties are increased resistance to phytopathogenic fungi, bacteria and / or viruses, which is due, for example, to systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and the correspondingly expressed proteins and toxins.

[0411] Particularly useful transgenic events in transgenic plants or plant cultivars that can preferably be treated according to the invention include Event 531 / PV-GHBK04 (cotton, insect control, described in W02002 / 040677); Event 1143-14A (cotton, insect control, not filed, described in WO2006 / 128569); Event 1143-51B (cotton, insect control, not filed, described in W02006 / 128570); Event 1445 (cotton, herbicide tolerance, not filed, described in US-A 2002-120964 or W02002 / 034946); Event 17053 (rice, herbicide tolerance, filed as PTA-9843, described in WO2010 / 117737). Event 17314 (Rice, herbicide tolerance, filed as PTA-9844, described in WO2010 / 117735); Event 281-24-236 (Cotton, insect control - herbicide tolerance, filed as PTA-6233, described in W02005 / 103266 or US-A 2005-216969);Event 3006-210-23 (Cotton, Insect Control - Herbicide Tolerance, filed as PTA-6233, described in US-A 2007-143876 or W02005 / 103266); Event 3272 (Corn, Quality Trait, filed as PTA-9972, described in W02006 / 098952 or US-A 2006-230473); Event 33391 (Wheat, Herbicide Tolerance, filed as PTA-2347, described in W02002 / 027004); Event 40416 (Corn, Insect Control - Herbicide Tolerance, filed as ATCC PTA-11508, described in WO 11 / 075593). Event 43A47 (Corn, Insect Control - Herbicide Tolerance, filed as ATCC PTA-11509, described in WO2011 / 075595); Event 5307 (Corn, Insect Control, filed as ATCC PTA-9561, described in W02010 / 077816); Event ASR-368 (Bentgrass, Herbicide Tolerance, filed as ATCC PTA-4816, described in US-A 2006-162007 or W02004 / 053062); Event B16 (Corn, Herbicide Tolerance, not filed, described in US-A 2003-126634);Event BPS-CV127-9 (Soybean, herbicide tolerance, filed as NCIMB No. 41603, described in W02010 / 080829); Event BLR1 (Canola, restoration of pollen sterility, filed as NCIMB 41193, described in W02005 / 074671); Event CE43-67B (Cotton, insect control, filed as DSM ACC2724, described in US-A 2009-217423 or WO2006 / 128573); Event CE44-69D (Cotton, insect control, not filed, described in US-A 2010-0024077); Event CE44-69D (Cotton, insect control, not filed, described in WO2006 / 128571); Event CE46-02A (Cotton, insect control, not registered, described in WO2006 / 128572); Event COT102 (Cotton, insect control, not registered, described in US-A 2006-130175 or W02004 / 039986); Event COT202 (Cotton, insect control, not registered, described in US-A 2007-067868 or W02005 / 054479); Event COT203 (Cotton, insect control, not registered, described in W02005 / 054480); );Event DAS21606-3 / 1606 (soybean, herbicide tolerance, filed as PTA-11028, described in WO2012 / 033794), Event DAS40278 (maize, herbicide tolerance, filed as ATCC PTA-10244, described in WO2011 / 022469); Event DAS-44406-6 / pDAB8264.44.06.1 (Soybean, herbicide tolerance, filed as PTA-11336, described in WO2012 / 075426), Event DAS-14536-7 / pDAB8291.45.36.2 (Soybean, herbicide tolerance, filed as PTA-11335, described in WO2012 / 075429), Event DAS-59122-7 (Corn, insect control - herbicide tolerance, filed as ATCC PTA 11384, described in US-A 2006-070139); Event DAS-59132 (Corn, insect control - herbicide tolerance, not filed, described in W02009 / 100188); Event DAS68416 (soybean, herbicide tolerance, filed as ATCC PTA-10442, described in WO2011 / 066384 or WO2011 / 066360); Event DP-098140-6 (corn, herbicide tolerance, filed as ATCC PTA-8296, described in US-A 2009-137395 or WO 08 / 112019);Event DP-305423-1 (Soybean, quality trait, not filed, described in US-A 2008-312082 or W02008 / 054747); Event DP-32138-1 (Corn, hybridization system, filed as ATCC PTA-9158, described in US-A 2009-0210970 or W02009 / 103049); Event DP-356043-5 (Soybean, herbicide tolerance, filed as ATCC PTA-8287, described in US-A 2010-0184079 or W02008 / 002872); Event EE-I (Eggplant, insect control, not filed, described in WO 07 / 091277); Event Fil 17 (Corn, herbicide tolerance, filed as ATCC 209031, described in US-A 2006-059581 or WO 98 / 044140); Event FG72 (Soybean, herbicide tolerance, filed as PTA-11041, described in WO2011 / 063413); Event GA21 (Corn, herbicide tolerance, filed as ATCC 209033, described in US-A 2005-086719 or WO 98 / 044140); Event GG25 (Corn, herbicide tolerance, filed as ATCC 209032, described in US-A 2005-188434 or W098 / 044140);Event GHB119 (Cotton, Insect Control - Herbicide Tolerance, filed as ATCC PTA-8398, described in W02008 / 151780); Event GHB614 (Cotton, Herbicide Tolerance, filed as ATCC PTA-6878, described in US-A 2010-050282 or W02007 / 017186); Event GH 1 (Corn, Herbicide Tolerance, filed as ATCC 209030, described in US-A 2005-188434 or WO98 / 044140); Event GM RZ13 (Sugar Beet, Virus Resistance, filed as NCIMB-41601, described in WO2010 / 076212); Event H7-1 (sugar beet, herbicide tolerance, filed as NCIMB 41158 or NCIMB 41159, described in US-A 2004-172669 or WO 2004 / 074492); Event JOPLIN1 (wheat, disease tolerance, not filed, described in US-A 2008-064032); Event LL27 (soybean, herbicide tolerance, filed as NCIMB41658, described in W02006 / 108674 or US-A 2008-320616); Event LL55 (soybean, herbicide tolerance, filed as NCIMB 41660, described in WO 2006 / 108675 or US-A 2008-196127);Event LLcotton25 (cotton, herbicide tolerance, filed as ATCC PTA-3343, described in W02003 / 013224 or US-A 2003-097687); Event LLRICE06 (rice, herbicide tolerance, filed as ATCC 203353, described in US 6,468,747 or W02000 / 026345); Event LLRice62 (rice, herbicide tolerance, filed as ATCC 203352, described in W02000 / 026345); Event LLRICE601 (rice, herbicide tolerance, filed as ATCC PTA-2600, described in US-A 2008-2289060 or W02000 / 026356); Event LY038 (Corn, quality characteristic, filed as ATCC PTA-5623, described in US-A 2007-028322 or W02005 / 061720); Event MIR162 (Corn, insect control, filed as PTA-8166, described in US-A 2009-300784 or W02007 / 142840); Event MIR604 (Corn, insect control, not filed, described in US-A 2008-167456 or W02005 / 103301); Event MON15985 (Cotton, insect control, filed as ATCC PTA-2516, described in US-A 2004-250317 or W02002 / 100163);Event MON810 (Corn, Insect Control, not filed, described in US-A 2002-102582); Event MON863 (Corn, Insect Control, filed as ATCC PTA-2605, described in W02004 / 011601 or US-A 2006-095986); Event MON87427 (Corn, Pollination Control, filed as ATCC PTA-7899, described in WO2011 / 062904); Event MON87460 (Corn, Stress Tolerance, filed as ATCC PTA-8910, described in W02009 / 111263 or US-A 2011-0138504); Event MON87701 (Soybean, insect control, filed as ATCC PTA-8194, described in US-A 2009-130071 or W02009 / 064652); Event MON87705 (Soybean, quality trait - herbicide tolerance, filed as ATCC PTA-9241, described in US-A 2010-0080887 or W02010 / 037016); Event MON87708 (Soybean, herbicide tolerance, filed as ATCC PTA-9670, described in WO2011 / 034704);Event MON87712 (Soybean, yield, filed as PTA-10296, described in W02012 / 051199); Event MON87754 (Soybean, quality trait, filed as ATCC PTA-9385, described in WO2010 / 024976); Event MON87769 (Soybean, quality trait, filed as ATCC PTA-8911, described in US-A 2011-0067141 or W02009 / 102873); Event MON88017 (Corn, insect control - herbicide tolerance, filed as ATCC PTA-5582, described in US-A 2008-028482 or W02005 / 059103); Event MON88913 (Cotton, herbicide tolerance, filed as ATCC PTA-4854, described in W02004 / 072235 or US-A 2006-059590); Event MON88302 (Canola, herbicide tolerance, filed as PTA-10955, described in WO2011 / 153186), Event MON88701 (Cotton, herbicide tolerance, filed as PTA-11754, described in WO2012 / 134808), Event MON89034 (Corn, insect control, filed as ATCC PTA-7455, described in WO 07 / 140256 or US-A 2008-260932);Event MON89788 (Soybean, herbicide tolerance, filed as ATCC PTA-6708, described in US-A 2006-282915 or W02006 / 130436); Event MSI 1 (Canola, pollination control - herbicide tolerance, filed as ATCC PTA-850 or PTA-2485, described in W02001 / 031042); Event MS8 (Canola, pollination control - herbicide tolerance, filed as ATCC PTA-730, described in W02001 / 041558 or US-A 2003-188347); Event NK603 (Corn, herbicide tolerance, filed as ATCC PTA-2478, described in US-A 2007-292854); Event PE-7 (Rice, insect control, not filed, described in W02008 / 114282); Event RF3 (Canola, pollination control - herbicide tolerance, filed as ATCC PTA-730, described in W02001 / 041558 or US-A 2003-188347); Event RT73 (Canola, herbicide tolerance, not filed, described in W02002 / 036831 or US-A 2008-070260);Event SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerance, filed as PTA-11226, described in WO2012 / 082548); Event T227-1 (sugar beet, herbicide tolerance, not filed, described in W02002 / 44407 or US-A 2009-265817); Event T25 (corn, herbicide tolerance, not filed, described in US-A 2001-029014 or WO2001 / 051654); Event T304-40 (cotton, insect control - herbicide tolerance, filed as ATCC PTA-8171, described in US-A 2010-077501 or W02008 / 122406); Event T342-142 (cotton, insect control, not filed, described in;

[0412] WO2006 / 128568); Event TC1507 (Corn, Insect Control - Herbicide Tolerance, not filed, described in US-A 2005-039226 or W02004 / 099447); Event VIP1034 (Corn, Insect Control -

[0413] Herbicide tolerance (stored as ATCC PTA-3925, described in W02003 / 052073), Event 32316 (Maize, insect control herbicide tolerance, stored as PTA-11507, described in WO2011 / 084632), Event 4114 (Maize, insect control herbicide tolerance, stored as PTA-

[0414] 11506, described in W02011 / 084621), Event EE-GM3 / FG72 (soybean, herbicide tolerance, ATCC access no. PTA-11041) optionally stacked with Event EE-GM1 / LL27 or Event EE-GM2 / LL55

[0415] (WO2011 / 063413A2), Event DAS-68416-4 (Soybean, Herbicide Tolerance, ATCC Access No. PTA-10442, W02011 / 066360A1), Event DAS-68416-4 (Soybean, Herbicide Tolerance, ATCC Access No. PTA-10442, WO2011 / 066384 Al), Event DP-040416-8 (Maize, Insect Control, ATCC Access No.

[0416] PTA-11508, WO2011 / 075593A1), Event DP-043A47-3 (Maize, Insect Control, ATCC Access No. PTA-11509, WO2011 / 075595 Al), Event DP-004114-3 (Maize, Insect Control, ATCC Access No. PTA-11506, WO2011 / 084621 Al), Event DP-032316-8 (Maize, Insect Control,

[0417] ATCC access number PTA-11507, WO2011 / 084632A1), Event MON-88302-9 (Rapeseed rape, herbicide tolerance, ATCC access no. PTA-10955, WO2011 / 153186A1), Event DAS-21606-3 (Soybean, herbicide tolerance, ATCC access no. PTA-11028, WO2012 / 033794A2), Event MON-87712-4 (Soybean, quality trait, ATCC access no. PTA-10296, WO2012 / 051199A2), Event DAS-44406-6 (Soybean, stacked herbicide tolerance, ATCC access no. PTA-11336, WO2012 / 075426A1), Event DAS-14536-

[0418] 7 (Soybean, stacked herbicide tolerance, ATCC access no. PTA-11335, WO2012 / 075429A1), Event SYN-000H2-5 (Soybean, herbicide tolerance, ATCC access no. PTA-11226, WO2012 / 082548 A2),

[0419] Event DP-061061-7 (Canola, herbicide tolerance, no deposit number available, W02012071039A1), Event DP-073496-4 (Canola, herbicide tolerance, no deposit number available, US2012131692), Event 8264.44.06.1 (Soybean, stacked herbicide tolerance, accession number PTA-11336, WO2012075426A2), Event 8291.45.36.2 (Soybean, stacked herbicide tolerance, accession number PTA-11335,

[0420] WO2012075429A2), Event SYHT0H2 (soybean, ATCC access no. PTA-11226,

[0421] WO2012 / 082548A2), Event MON88701 (Cotton, ATCC Access No. PTA-11754,

[0422] WO2012 / 134808A1), Event KK179-2 (Alfalfa, ATCC Accession No. PTA-11833, W02013 / 003558A1), Event pDAB8264.42.32.1 (Soybean, stacked herbicide tolerance, ATCC Accession No. PTA-11993, WO2013 / 010094 Al), Event MZDT09Y (Corn, ATCC Accession No. PTA-13025, WO2013 / 012775 Al). Furthermore, such a list of transgenic events is provided by the United States Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website at https: / / www.aphis.usda.gov / . For the present application, the status of this list as it was on the filing date of the present application is relevant.

[0423] The genes / events that confer the desired traits can also occur in combination with one another in transgenic plants. Examples of transgenic plants that can be mentioned include important crops such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peas and other types of vegetables, cotton, tobacco, rapeseed, and also fruit plants (including apples, pears, citrus fruits, and grapes), with maize, soybeans, wheat, rice, potatoes, cotton, sugarcane, tobacco, and rapeseed being particularly noteworthy. Traits that are particularly emphasized are the plants' increased resistance to insects, arachnids, nematodes, and slugs, as well as the plants' increased resistance to one or more herbicides.

[0424] Commercially available examples of such plants, plant parts, or plant seeds that can be preferably treated according to the invention include commercially available products such as plant seeds that fall under the GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY®, VT DOUBLE PRO®, VT TRIPLE PRO®, BOLLGARD II®, ROUNDUP READY 2 YIELD®, YIELDGARD®, and ROUNDUP READY® 2 XTEN categories. DTM -, INTACTA RR2 PRO®, VISTIVE GOLD® and / or XTENDFLEX™ trade names are sold or distributed

[0425] Plant protection - Treatment methods

[0426] The treatment of plants and plant parts with the compounds of formula (I) is carried out directly or by acting upon their environment, habitat, or storage area according to usual treatment methods, e.g., by dipping, spraying, misting, sprinkling, evaporating, atomizing, fogging, scattering, foaming, brushing, spreading, injecting, drenching, drip irrigation, and, in the case of propagation material, especially seeds, furthermore by dry dressing, wet dressing, slurry dressing, incrustation, single- or multi-layer coating, etc. It is also possible to apply the compounds of formula (I) using the ultra-low-volume method or to inject the application form or the compound of formula (I) itself into the soil.

[0427] A preferred direct treatment of the plants is foliar application, i.e., the compounds of formula (I) are applied to the foliage, whereby the treatment frequency and application rate should be adjusted to the infestation pressure of the respective pest. With systemically acting active ingredients, the compounds of formula (I) also reach the plants via the root system. The treatment of the plants then takes place through the action of the compounds of formula (I) on the plant's habitat. This can be done, for example, by drenching, mixing into the soil or nutrient solution, i.e., the plant's location (e.g., soil or hydroponic systems) is saturated with a liquid form of the compounds of formula (I), or by soil application, i.e., the compounds of formula (I) according to the invention are applied in solid form (e.g.,in the form of granules) into the plant location, or by drip application (often also referred to as "chemigation"), i.e., the compounds of formula (I) according to the invention are introduced by means of surface or subsurface drip lines over specific periods of time together with varying amounts of water at defined locations near the plants. In the case of aquatic rice cultivation, this can also be done by adding the compound of formula (I) in a solid application form (e.g. as granules) to a flooded rice field.

[0428] Digital technologies

[0429] The compounds according to the invention can be used in combination with, for example, models embedded in computer programs for site-specific crop management, satellite agriculture, precision agriculture, or precision farming. Such models support the site-specific management of agricultural assets with data from various sources such as soils, weather, crops (e.g., type, growth stage, plant health), weeds (e.g., type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield, etc., with the aim of optimizing profitability, sustainability, and environmental protection. In particular, such models can help to optimize agronomic decisions, control the precision of pesticide applications, and record the work performed.

[0430] For example, the compounds according to the invention can be applied to a crop plant according to a corresponding application protocol if the model modulates the occurrence of a pest and calculates that a threshold has been reached at which it is recommended to apply the compound according to the invention to the crop plant.

[0431] Commercially available systems that include agronomic models include, for example, FieldScriptsTM from The Climate Corporation, XarvioTM from BASF, AGLogicTM from John Deere, etc.

[0432] The compounds according to the invention can also be used in combination with smart sprayers, such as spot sprayers or precision sprayers, which are mounted on or housed in a farm vehicle such as a tractor, robot, helicopter, airplane, or unmanned aerial vehicle (UAV) like a drone. Such a device usually includes input sensors (such as a camera) and a processing unit configured to analyze the input data and provide a decision, based on this analysis, for applying the compound according to the invention to the crops (or weeds) in a specific and precise manner. The use of such smart sprayers usually requires positioning systems (e.g., GPS receivers) with which the recorded data can be located and the farm vehicle controlled.Controlled geographic information systems (GIS) that display the information on understandable maps, and appropriate farm vehicles to carry out the necessary agricultural measures such as spraying.

[0433] In one example, pests can be detected from images captured by a camera. In another example, the pests can be identified and / or classified based on these images. Such identification and / or classification can utilize image processing algorithms. These algorithms can employ machine learning algorithms such as artificial neural networks, decision trees, and artificial intelligence algorithms. This allows the connections described here to be applied only where needed.

[0434] Seed treatment

[0435] Controlling animal pests by treating plant seeds has long been known and is subject to continuous improvement. Nevertheless, seed treatment presents a number of problems that cannot always be satisfactorily resolved. It is therefore desirable to develop methods for protecting seeds and germinating plants that eliminate or at least significantly reduce the need for additional application of pesticides during storage, after sowing, or after emergence. Furthermore, it is desirable to optimize the amount of active ingredient used so that the seeds and germinating plants are protected as effectively as possible from infestation by animal pests, without harming the plant itself with the active ingredient. In particular, seed treatment methods should also utilize the intrinsic insecticidal properties of the seeds.to incorporate the nematicidal properties of pest-resistant or pest-tolerant transgenic plants in order to achieve optimal protection of the seed and also the germinating plant with a minimal use of pesticides.

[0436] The present invention therefore relates in particular to a method for protecting seeds and germinating plants from pest infestation 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 pest infestation further comprises a method in which the seeds are treated simultaneously in one operation or sequentially with a compound of formula (I) and a mixture component. It also further comprises a method in which the seeds are treated at different times with a compound of formula (I) and a mixture component.

[0437] The invention also relates to the use of the compounds of formula (I) for the treatment of seeds to protect the seeds and the resulting plant from animal pests.

[0438] The invention further relates to seed treated with a compound of formula (I) according to the invention for protection against animal pests. The invention also relates to seed treated simultaneously with a compound of formula (I) and a mixture component. The invention further relates to seed treated at different times with a compound of formula (I) and a mixture component. In the case of seed treated at different times with a compound of formula (I) and a mixture component, the individual substances may be present in different layers on the seed. The layers containing a compound of formula (I) and mixture components may optionally be separated by an intermediate layer.The invention also relates to seed in which a compound of formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating.

[0439] Furthermore, the invention relates to seed which, after treatment with a compound of formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.

[0440] One of the advantages of a compound of formula (I) acting systemically is that the treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter can be omitted.

[0441] Another advantage is that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.

[0442] It is also advantageous that compounds of formula (I) can be used particularly in transgenic seeds. Furthermore, compounds of formula (I) can be used in combination with signaling technology compositions or compounds, resulting in improved colonization by symbionts such as rhizobia, mycorrhizae and / or endophytic bacteria or fungi, and / or optimized nitrogen fixation.

[0443] The compounds of formula (I) are suitable for protecting seeds of any plant variety used in agriculture, greenhouses, forestry, or horticulture. This includes, in particular, seeds of cereals (e.g., wheat, barley, rye, millet, and oats), maize, cotton, soybeans, rice, potatoes, sunflowers, coffee, tobacco, canola, rapeseed, beets (e.g., sugar beets and fodder beets), peanuts, vegetables (e.g., tomatoes, cucumbers, beans, brassicas, onions, and lettuce), fruit plants, lawns, and ornamental plants. The treatment of seeds of cereals (such as wheat, barley, rye, and oats), maize, soybeans, cotton, canola, rapeseed, vegetables, and rice is of particular importance.

[0444] As mentioned above, the treatment of transgenic seeds with a compound of formula (I) is also of particular importance. These are seeds of plants that generally contain at least one heterologous gene that controls the expression of a polypeptide with, in particular, insecticidal or nematicidal properties. The heterologous genes in transgenic seeds can originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus, or Gliocladium. The present invention is particularly suitable for the treatment of transgenic seeds that contain at least one heterologous gene originating from Bacillus sp. Preferably, this is a heterologous gene originating from Bacillus thuringiensis.

[0445] 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 it is stable enough that no damage occurs during treatment. In general, the seed treatment can be carried out at any time between harvest and sowing. Typically, seed is used that has been separated from the plant and freed from cobs, husks, stems, hulls, wool, or pulp. For example, seed can be used that has been harvested, cleaned, and dried to a suitable moisture content for storage. Alternatively, seed can be used that, after drying, has been treated with water and then dried again, for example, by priming.In the case of rice seed, it is also possible to use seed that has been soaked, for example in water, up to a certain stage of the rice embryo (“Pigeon Breast Stage”), which stimulates germination and a more uniform emergence.

[0446] In general, when treating seeds, care must be taken to ensure that the amount of compound (I) and / or other additives applied to the seeds is chosen so that seed germination is not impaired or the resulting plant is not damaged. This is particularly important to consider with active ingredients that can exhibit phytotoxic effects at certain application rates.

[0447] The compounds of formula (I) are generally 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.

[0448] The compounds of formula (I) can be incorporated into the usual seed treatment formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coatings for seeds, as well as ULV formulations.

[0449] These formulations are prepared in a known manner by mixing the compounds of formula (I) with usual additives, such as usual extenders, solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.

[0450] All dyes commonly used for such purposes are suitable as colorants that may be included in the mordant formulations usable according to the invention. Both pigments that are sparingly soluble in water and dyes that are soluble in water can be used. Examples include the dyes known as Rhodamin B, CI Pigment Red 112, and CI Solvent Red 1.

[0451] All substances commonly used in the formulation of agrochemical active ingredients that promote wetting are suitable as wetting agents that may be included in the seed treatment formulations usable according to the invention. Alkylnaphthalenesulfonates, such as diisopropyl or diisobutylnaphthalenesulfonates, are particularly suitable.

[0452] All nonionic, anionic, and cationic dispersants commonly used in the formulation of agrochemical active ingredients are suitable as dispersants and / or emulsifiers that may be included in the seed treatment formulations usable according to the invention. Nonionic or anionic dispersants, or mixtures thereof, are particularly suitable. Suitable nonionic dispersants include, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers, tristyrylphenol polyglycol ethers, and their phosphated or sulfated derivatives. Suitable anionic dispersants include, in particular, lignosulfonates, polyacrylic acid salts, and arylsulfonate-formaldehyde condensates. The defoaming agents used in the seed treatment formulations according to the invention can contain all foam-inhibiting substances commonly used in the formulation of agrochemical active ingredients.Silicone defoamers and magnesium stearate are preferably suitable.

[0453] The seed treatment formulations usable according to the invention can contain as preservatives any substances that can be used for such purposes in agrochemicals. Examples include dichlorophene and benzyl alcohol hemiformal.

[0454] Suitable secondary thickening agents that may be included in the seed treatment formulations usable according to the invention are all substances that can be used for such purposes in agrochemicals. Cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays, and highly dispersed silica are particularly preferred.

[0455] Suitable adhesives that can be included in the mordant formulations usable according to the invention are all conventional binders that can be used in mordants. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and Tylose are particularly preferred.

[0456] The gibberellins that may be included in the seed treatment formulations usable according to the invention are preferably the gibberellins Al, A3 (= gibberellic acid), A4 and A7; gibberellic acid is particularly preferred. The gibberellins are known (see R. Wegler, "Chemistry of Plant Protection and Pest Control Products", Vol. 2, Springer Verlag, 1970, pp. 401-412).

[0457] The seed treatment formulations usable according to the invention can be used either directly or after prior dilution with water to treat seeds of various types. The concentrates or the preparations obtainable from them by dilution with water can be used to treat the seeds of cereals such as wheat, barley, rye, oats, and triticale, as well as the seeds of maize, rice, rapeseed, peas, beans, cotton, sunflowers, soybeans, and beets, or also vegetable seeds of various kinds. The seed treatment formulations usable according to the invention, or their diluted forms, can also be used to treat the seeds of transgenic plants.

[0458] For treating seeds with the seed treatment formulations usable according to the invention, or with application forms produced therefrom by adding water, all mixing equipment commonly used for seed treatment is suitable. Specifically, the seed treatment process involves placing the seeds in a mixer operating intermittently or continuously, adding the desired quantity of seed treatment formulations, either as such or after prior dilution with water, and mixing until the formulation is uniformly distributed on the seeds. A drying process may follow. The application rate of the seed treatment formulations usable according to the invention can be varied within a wide range. It depends on the respective content of the compounds of formula (I) in the formulations and on the type of seed.The application rates for the combination of formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.

[0459] Animal health

[0460] In the field of animal health, i.e., veterinary medicine, the compounds of formula (I) are effective against animal parasites, especially ectoparasites or endoparasites. The term endoparasite includes, in particular, helminths and protozoa such as coccidia. Ectoparasites are typically and preferentially arthropods, especially insects or acarids.

[0461] In the field of veterinary medicine, the compounds of formula (I), which exhibit favorable toxicity towards warm-blooded animals, are suitable for controlling parasites that occur in animal breeding and husbandry in farm animals, breeding animals, zoo animals, laboratory animals, experimental animals and pets. They are effective against all or individual developmental stages of the parasites.

[0462] Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer and especially cattle and pigs; or poultry such as turkeys, ducks, geese and especially chickens; or fish or crustaceans, e.g. in aquaculture, or possibly insects such as bees.

[0463] Pets include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and especially dogs, cats, pet birds; reptiles, amphibians or aquarium fish.

[0464] According to one particular embodiment, the compounds of formula (I) are administered to mammals.

[0465] According to another specific embodiment, the compounds of formula (I) are administered to birds, namely pet birds or, in particular, poultry.

[0466] The use of the compounds of formula (I) for the control of animal parasites is intended to reduce or prevent disease, deaths and reduced performance (in meat, milk, wool, hides, eggs, honey and the like), thus enabling more economical and simpler animal husbandry and achieving better animal welfare.

[0467] In the context of animal health, the term "control" or "to combat" means that the compounds of formula (I) effectively reduce the occurrence of the respective parasite in an animal infected with such parasites to a harmless degree. More precisely, "to combat" in this context means that the compounds of formula (I) kill the respective parasite, prevent its growth, or prevent its reproduction.

[0468] Arthropods include, but are not limited to, the following from the order Anoplurida: Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; from the order Mallophagida and the suborders Amblycerina and Ischnocerina: Bovicola spp., Damalina spp., Felicola spp.; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp. 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., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp., Melophagus spp., Morellia spp., Musea 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.; from the order Siphonapterida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp.; as well as pests and hygiene pests from the order Blattarida.

[0469] Furthermore, the following arthropods are examples, but not limited to:

[0470] From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Omithodorus spp., Otobius spp., from the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genus of multi-host ticks); from the order Mesostigmata, such as Dermanyssus spp., Omithonyssus spp., Pneumonyssus spp., Raillietia spp., Stemostoma spp., Tropilaelaps spp., Varroa spp.; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Omithocheyletia spp., Psorergates spp., Trombicula spp.; and from the order Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp.

[0471] Examples of parasitic protozoa include, but are not limited to:

[0472] Mastigophora (Flage llata), such as:

[0473] Metamonada: from the order Diplomonadida, for example Giardia spp., Spironucleus spp.

[0474] Parabasala: from the order Trichomonadida, for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.

[0475] Euglenozoa: from the order Trypanosomatida, for example Leishmania spp., Trypanosoma spp.

[0476] Sarcomastigophora (Rhizopoda), such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp.

[0477] Alveolata such as Apicomplexa (Sporozoa): e.g., Cryptosporidium spp.; from the order Eimeriida, for example, Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; from the order Adeleida, e.g., Hepatozoon spp., Klossiella spp.; from the order Haemosporida, e.g., Leucocytozoon spp., Plasmodium spp.; from the order Piroplasmida, e.g., Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; from the order Vesibuliferida, e.g., Balantidium spp., Buxtonella spp.

[0478] Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., and also, for example, Myxozoa spp.

[0479] Examples of helminths that are pathogenic to humans or animals include Acanthocephala, nematodes, Pentastoma and platyhelminths (e.g. Monogenea, Cestodes and Trematodes).

[0480] Examples of helminths include, but are not limited to:

[0481] Monogenea: e.g. E.g.: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp.;

[0482] Cestodes: from the order Pseudophyllidea, for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp., Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.

[0483] From the order Cyclophyllida, for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.

[0484] Trematodes: from the class Digenea, for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Omithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.

[0485] Nematodes: from the order Trichinellida, for example: Capillaria spp., Eucoleus spp., Paracapillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.

[0486] From the order Tylenchida, for example: Micronema spp., Parastrangyloides spp., Strongyloides spp.

[0487] Aus der Ordnung Rhabditina zum Beispiel: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Ha- emonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoi- des spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.; Omithostrongylus spp., Os- lerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafdaroides spp., Pare- laphostrongylus spp., Pneumocaulus spp., Pneumo strongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylus spp., Syngamus spp., Teladorsagia spp., Tricho- nema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp.

[0488] From the order Spirurida, for example: Acanthocheilonema spp., Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifdaria spp., Crassicauda spp., Dipetalonema spp., Dirofdaria spp., Dracunculus spp.; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafdaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofdaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp., Stephanofdaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp. Acanthocephala: from the order Oligacanthorhynchida e.g.: Macracanthorhynchus spp., Prosthenorchis spp.; from the order Moniliformida, for example: Moniliformis spp.,

[0489] From the order Polymorphida, for example: Filicollis spp.; from the order Echinorhynchida, for example: Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.

[0490] Pentastoma: from the order Porocephalida, for example Linguatula spp.

[0491] Parasites of fish include, for example, crustaceans, which in turn comprise the following families: Caligidae with the exemplary species Dissonus, Caligus (e.g., BC curtus, C. elongates, C. clemensi, C. rogercresseyii) and Lepeophtheirus (e.g., BL salmonis); the families Cecropidae, Dichelesthiidae, Lernaeopodidae with the exemplary species Salmincola; the families Pandaridae, Pennellidae with the exemplary species Lernaeocera and Pennella; the family Sphyriidae; the family Lernaeidae with the exemplary species Lernaea; the families Bomolochidae, Chondracanthidae, Ergasilidae and Philichthyidae; the family Argulidae with the exemplary species Argulus (e.g., BA foliaceus).

[0492] In the field of veterinary medicine and animal husbandry, the compounds of formula (I) are administered according to generally known procedures, such as enteral, parenteral, dermal, or nasal administration in the form of suitable preparations. Administration can be prophylactic, metaphylactic, or therapeutic.

[0493] One embodiment of the present invention relates to the compounds of formula (I) for use as pharmaceuticals.

[0494] Another aspect relates to the compounds of formula (I) for use as an anti-endoparasitic agent.

[0495] Another special aspect concerns the compounds of formula (I) for use as an antihelminthic, in particular for use as a nematicide, platymelminthicide, acanthocephalicide or pentastomicide.

[0496] Another special aspect concerns the compounds of formula (I) for use as antiprotozoal agents.

[0497] Another aspect concerns the compounds of formula (I) for use as an antiectoparasitic, in particular an arthropodicide, especially an insecticide or an acaricide.

[0498] Further aspects of the invention are veterinary formulations comprising an effective amount of at least one compound of formula (I) and at least one of the following: a pharmaceutically safe excipient (e.g., solid or liquid diluents), a pharmaceutically safe excipient (e.g., surfactants), in particular a pharmaceutically safe excipient and / or an excipient conventionally used in veterinary formulations.

[0499] A related aspect of the invention is a method for producing a veterinary medicinal formulation as described herein, comprising the step of mixing at least one compound of formula (I) with pharmaceutically safe excipients and / or excipients, in particular with pharmaceutically safe excipients and / or excipients conventionally used in veterinary medicinal formulations.

[0500] Another special aspect of the invention is veterinary medicinal formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoal and arthropodicidal formulations, and especially selected from the group of nematicide, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal formulations, according to the aforementioned aspects, as well as methods for their preparation.

[0501] Another aspect relates to a method for treating a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites mentioned herein, by applying an effective amount of a compound of formula (I) to an animal, in particular a non-human animal, which requires it.

[0502] Another aspect relates to a procedure for treating a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites mentioned herein, by applying a veterinary formulation as defined herein to an animal, in particular a non-human animal, that requires it.

[0503] Another aspect relates to the use of the compounds of formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal.

[0504] In the present animal health or veterinary context, the term "treatment" includes prophylactic, metaphylactic, and therapeutic treatment. In a particular embodiment, mixtures of at least one compound of formula (I) with other active substances, in particular with endo- and ectoparasiticides, are hereby made available for the veterinary field.

[0505] In the field of animal health, "mixture" does not only mean that two (or more) different active ingredients are formulated in a single formulation and used together, but also refers to products that contain separate formulations for each active ingredient. Accordingly, if more than two active ingredients are to be used, all active ingredients can be formulated in a single formulation, or all active ingredients can be formulated separately; mixed forms are also conceivable, in which some of the active ingredients are formulated together and some are formulated separately. Separate formulations allow for the separate or sequential use of the active ingredients in question.

[0506] The active ingredients specified here by their “Common Name” are known and are described, for example, in the “Pesticide Manual” (see above) or can be researched on the Internet (e.g. http: / / www.alan-wood.net / pesticides).

[0507] Examples of active ingredients from the group of ectoparasiticides suitable as mixing partners include, but are not limited to, the insecticides and acaricides listed in detail above. Further usable active ingredients are listed below according to the classification mentioned above, which is based on the current IRAC Mode of Action Classification Scheme: (1) Acetylcholinesterase (AChE) inhibitors; (2) GABA-gated chloride channel blockers; (3) Sodium channel modulators; (4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR); (5) Allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) Allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) Juvenile hormone mimetics; (8) Various non-specific (multi-site) inhibitors; (9) Chordotonal organ modulators; (10) Mite growth inhibitors; (12) Mitochondrial ATP synthase inhibitors, such as ATP disruptors;(13) Uncouplers of oxidative phosphorylation by disruption of the proton gradient; (14) Blockers of the nicotinic acetylcholine receptor channel; (15) Inhibitors of chitin biosynthesis, type 0; (16) Inhibitors of chitin biosynthesis, type 1; (17) Molting disruptor (especially in Diptera, i.e., true flies); (18) Ecdysone receptor agonists; (19) Octopamine receptor agonists; (21) Mitochondrial complex I electron transport inhibitors; (25) Mitochondrial complex II electron transport inhibitors; (20) Mitochondrial complex III electron transport inhibitors; (22) Voltage-gated sodium channel blockers; (23) Inhibitors of acetyl-CoA carboxylase; (28) Ryanodine receptor modulators; (30) allosteric modulators of the GABA-dependent chloride channel; (33) calcium-activated potassium channel KCa2 modulators; (34) mitochondrial complex III electron transport inhibitors (non-Qo binding site);

[0508] Active substances with unknown or non-specific mechanisms of action, e.g., fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, flutenzin, bromopropylate, cryolite;

[0509] Connections from other classes:

[0510] Butacarb, Dimetilan, Cloethocarb, Phosphocarb, Pirimiphos(-ethyl), Parathion(-ethyl), Methacrifos, Isopropyl-o-salicylate, Trichlorfon, Sulprofos, Propaphos, Sebufos, Pyridathion, Prothoate, Dichlofenthion, Demeton-S-methylsulfone, Isazofos, Cyanofenphos, Dialifos, Carbophenothione, Autathiofos, Aromfenvinfos(-methyl), Azinphos(-ethyl), Chlorpyrifos(-ethyl), Fosmethilan, Iodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensulfothion, Etrimfos, Atelocantel;

[0511] Organochlorine compounds, e.g. camphechlorine, lindane, heptachlor;

[0512] Phenylpyrazole, z. B. Acetoprole, Pyrafluprole, Pyriprole, Vaniliprole, Sisapronile;

[0513] Isoxazoline, z. B. Afoxolaner, Esafoxolaner, Fluralaner, Lotilaner, FluralanerMivorilaner, Modoflaner, Sarolaner, Umifoxolaner;

[0514] Pyrazolyl-Arylamide, z. B. Nicofluprole, Tigolaner;Pyrethroide, z. B. (cis-, trans-)Metofluthrin, Pro- fluthrin, Flufenprox, Flubrocythrinat, Fubfenprox, Fenfluthrin, Protrifenbut, Pyresmethrin, RUI 5525, Terallethrin, cis-Resmethrin, Heptafluthrin, Bioethanomethrin, Biopermethrin, Fenpyrithrin, cis-Cyper- methrin, cis-Permethrin, Clocythrin, Cyhalothrin (lambda-), Chlovaporthrin, oder halogenierte Kohlenwasserstoffverbindungen (HCHs),

[0515] Neonicotinoide, z. B. Nithiazin

[0516] Dicloromezotiaz, Triflumezopyrim makrocyclische Lactone, z. B. Nemadectin, Ivermectin, Latidectin, Moxidectin, Selamectin, Eprino- mectin, Doramectin, Emamectinbenzoat; Milbemycinoxim

[0517] triprene, epofenonan, diofenolan;

[0518] Biologicals, hormones or pheromones, for example natural products, e.g. Thuringiensin, Codlemon or Neem components; dinitrophenols, e.g. Dinocap, Dinobuton, Binapacryl;

[0519] Benzoyl ureas, e.g. B. fluazuron, penfluron,

[0520] amidine derivatives, e.g. B. chlormebuform, cymiazole, demiditraz;

[0521] Tetronic or tetramic acid derivatives, e.g. spidoxamate, spirobudiclofen;

[0522] Beehive Varroa acaricides, for example organic acids, e.g. formic acid, oxalic acid.

[0523] Examples of active ingredients from the group of endoparasiticides, as mixing partners, include, but are not limited to, anthelmintic and antiprotozoal agents.

[0524] Anthelmintic active ingredients include, but are not limited to, the following nematicidal, tremicidal and / or cestocidal active ingredients: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin, milbemycin; from the class of benzimidazoles and probenecids, for example: oxibendazole, mebendazole, triclabentazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flubendazole; from the class of depsipeptides, preferably cyclic depsipeptides, in particular 24-membered cyclic depsipeptides, for example: emodepside, PF1022A; from the class of tetrahydropyrimidines, for example: morantel, pyrantel, oxantel; from the class of imidazothiazoles, for example: butamisole, levamisole, tetramisole;from the class of aminophenylamidines, for example: amidantel, deacylated amidantel (dAMD), tribendimidine; from the class of aminoacetonitriles, for example: monepantel; from the class of paraherquamides, for example: paraherquamide, derquantel; from the class of salicylanides, for example: tribromsalan, bromoxanide, brotianide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxanide; from the class of substituted phenols, for example: nitroxynil, bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan; from the class of organophosphates, for example: trichlorfon, naphthalofos, dichlorvos / DDVP, crufomate, coumaphos, haloxone; Examples of piperazino / quinoline drugs include: praziquantel, aparziquantel, epsiprantel; piperazine drugs include: piperazine, hydroxyzine; and tetracycline drugs include: tetracycline, chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline.from various other classes, for example: Bunamidine, Niridazole, Resorantel, Omphalotin, Oltipraz, Nitroscanate, Nitroxynil, Oxamniquin, Mirasan, Miracil, Lucanthon, Hycanthon, Hetolin, Emetin, Diethylcarbamazine, Dichlorophen, Diamfenetide, Clonazepam, Bephenium, Amoscanate, Clorsulone.;

[0525] Antiprotozoal agents, including, but not limited to, the following: from the triazine class, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the polyletherionophore class, for example: monensin, salinomycin, maduramicin, narasin; from the macrocyclic lactone class, for example: milbemycin, erythromycin; from the quinolone class, for example: enrofloxacin, pradofloxacin; from the quinine class, for example: chloroquine; from the pyrimidine class, for example: pyrimethamine; from the sulfonamide class, for example: sulfaquinoxaline, trimethoprim, sulfaclocin; from the thiamine class, for example: amprolium; from the lincosamide class, for example: clindamycin; from the carbanilide class, for example: imidocarb; From the nitrofuran class, for example: nifurtimox; from the quinazoline alkaloid class, for example: halofuginone; from various other classes, for example: oxamniquin, paromomycin;from the class of vaccines or antigens from microorganisms for example: Babesia canis rossi, Meileria tenella, Meileia praecox, Meileia necatrix, Meileia mitis, Meileia maxima, Meileia brunetti, Meileia acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus vi- viparus.;

[0526] All the aforementioned mixing partners can also form salts with suitable bases or acids if they are capable of doing so due to their functional groups.

[0527] Vector control

[0528] The compounds of formula (I) can also be used in vector control. A vector within the meaning of the present invention is an arthropod, in particular an insect or arachnid, that is capable of transmitting pathogens such as viruses, worms, protozoa, and bacteria from a reservoir (plant, animal, human, etc.) to a host. The pathogens can be transmitted either mechanically (e.g., trachoma by non-biting flies) or by injection (e.g., malaria parasites by mosquitoes) into a host.

[0529] Examples of vectors and the diseases or pathogens they transmit are:

[0530] 1) Mosquitoes

[0531] - Anopheles: malaria, filariasis;

[0532] - Culex: Japanese encephalitis, other viral diseases, filariasis, transmission of other worms;

[0533] - Aedes: Yellow fever, dengue fever, other viral diseases, filariasis;

[0534] - Simia: Transmission of worms, especially Onchocerca volvulus;

[0535] - Psychodidae: Transmission of leishmaniasis

[0536] 2) Lice: skin infections, epidemic typhus;

[0537] 3) Fleas: Plague, endemic typhus, tapeworms;

[0538] 4) Flies: Sleeping sickness (trypanosomiasis); cholera, other bacterial diseases;

[0539] 5) Mites: Acariosis, epidemic typhus, rickettsipox, tularemia, Saint Louis encephalitis, tick-borne encephalitis (TBE), Crimean-Congo hemorrhagic fever, Lyme disease;

[0540] 6) Ticks: Lyme diseases such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), babesiosis (Babesia canis canis), ehrlichiosis. Examples of vectors within the meaning of the present invention are insects, for example, aphids, flies, cicadas, or thrips, which can transmit plant viruses to plants. Other vectors that can transmit plant viruses are spider mites, aphids, beetles, and nematodes.

[0541] Further examples of vectors within the meaning of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. BA gambiae, A. arabiensis, A. funestus, A. dims (Malaria) and Culex, psychodids such as Phlebotomus, Lutzomyia, lice, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.

[0542] Vector control is also possible if the compounds of formula (I) are resistance-breaking.

[0543] Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors. Thus, a further aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, gardens and recreational facilities, as well as in the protection of stored products and materials.

[0544] Protection of technical materials

[0545] The compounds of formula (I) are suitable for protecting technical materials against infestation or destruction by insects, e.g. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.

[0546] In this context, "technical materials" refers to non-living materials, such as preferably plastics, adhesives, glues, papers and cardboards, leather, wood, wood-based products, and coatings. The application of the invention for the protection of wood is particularly preferred.

[0547] In another embodiment, the compounds of formula (I) are used together with at least one other insecticide and / or at least one fungicide.

[0548] In another embodiment, the compounds of formula (I) are available as a ready-to-use pesticide, i.e., they can be applied to the relevant material without further modification. The insecticides or fungicides mentioned above are particularly suitable as additional insecticides or fungicides.

[0549] Surprisingly, it was also found that the compounds of formula (I) can be used to protect objects, especially ship hulls, sieves, nets, structures, quays and signaling equipment, from fouling when exposed to seawater or brackish water. Likewise, the compounds of formula (I) can be used alone or in combination with other active ingredients as antifouling agents.

[0550] Control of animal pests in the hygiene sector

[0551] The compounds of formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene, and stored product protection, especially for controlling insects, arachnids, ticks, and mites found in enclosed spaces such as apartments, factory halls, offices, vehicle cabins, and animal breeding facilities. For controlling these animal pests, the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients. They are preferably used in household insecticide products. The compounds of formula (I) are effective against susceptible and resistant species as well as against all developmental stages.

[0552] 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 the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.

[0553] Applications include, for example, aerosols, non-pressurized sprays (e.g., pump and atomizer sprays), fog machines, fogging systems, foams, gels, evaporator products with evaporator plates made of cellulose or plastic, liquid evaporation, gel and membrane evaporation, propeller-driven evaporators, energy-free or passive evaporation systems, moth papers, moth sachets and moth gels, as granules or dusts, in scatter baits or bait stations.

[0554] Analytical methods

[0555] The analytical procedures described below apply to all information in the entire document, unless the specific analytical procedure is described separately at the relevant point in the text.

[0556] Mass spectrometry / LCMS

[0557] LC-MS acidic

[0558] The determination of [M+H] + or M" by LC-MS under acidic chromatographic conditions was performed using 1 ml of formic acid per liter of acetonitrile and 0.9 ml of formic acid per liter of Millipore water as eluents. A Zorbax Eclipse Plus C18 50 mm × 2.1 mm column was used at an oven temperature of 55 °C.

[0559] Instruments:

[0560] LC-MS3, LC-MS6 and LC-MS7: Waters Acquity IClass with SQD2 mass spectrometer and FTN sample changer. Linear gradient from 10% acetonitrile to 95% acetonitrile from 0.0 to 1.70 minutes, constant 95% acetonitrile from 1.70 to 2.40 minutes, flow rate 0.85 ml / min.

[0561] LC-MS neutral

[0562] The determination of [M+H] + LC-MS under neutral chromatographic conditions was performed using acetonitrile and Millipore water with 79 mg / l ammonium carbonate as the eluent. A Waters Acquity 1.7 pm 50 mm × 2.1 mm column was used at an oven temperature of 45°C.

[0563] Instruments:

[0564] LC-MS4 and LC-MS8: Waters Acquity IClass with QDA mass spectrometer and FTN sample changer. Linear gradient from 0.0 to 2.10 minutes from 10% acetonitrile to 95% acetonitrile, from 2.10 to 3.00 minutes constant 95% acetonitrile, flow rate 0.7 ml / min.

[0565] Retention time indices

[0566] The retention time indices were determined in all cases according to a homologous series of straight-chain alkan-2-ones with 3 to 16 carbon atoms, with the index of the first alkanone set to 300, that of the last to 1600, and linear interpolation performed between the values ​​of successive alkanones. logP values: The logP values ​​were determined in accordance with EC No 440 / 2008, adapted by (EU) 2016 / 266, Annex, method A.24, using HPLC (High Performance Liquid Chromatography) on a phase-reversing column (CI 8). The calibration of the above methods was carried out using straight-chain alkan-2-ones (with 3 to 16 carbon atoms) with known logP values. The values ​​between successive alkanones were determined by linear regression. The calibration is regularly checked with 7 test substances with known logP values ​​in the range between 0.7 and 4.3.

[0567] NMR spectroscopy

[0568] The ¹H NMR spectra were measured using a Bruker Avance Neo 600 MHz spectrometer (AV600NE02) equipped with a 5 mm TCI probe, with tetramethylsilane as the standard (0.00 ppm). Measurements were typically recorded using solutions in the solvents CD3CN, CDCL, or de-DMSO. Alternatively, a Bruker Avance Neo 600 MHz spectrometer (AV601) equipped with a 5 mm CPNMP probe or a Bruker Avance NEO 600 MHz spectrometer (AV600NEO) equipped with a 5 mm TCI probe was used. Measurements were generally performed at a probe temperature of 298 K. Any other measurement temperatures used are noted separately.

[0569] NMR peak list method

[0570] The 1¹H NMR data from selected examples are presented in the form of '¹H NMR peaks'. For each signal peak, the ¹H value in ppm is listed first, followed by the signal intensity in parentheses. The ¹H value-signal intensity pairs are separated by semicolons.

[0571] The peak list of an example therefore has the form:

[0572] 81 (Intensity:); 82 (Intensity2); ; 81 (Intensity); ; 8 n (Intensity,)

[0573] The intensity of sharp signals correlates with the height of the signals in a printed representation of a 1H NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.

[0574] Tetramethylsilane is used to calibrate the chemical shift of ¹H NMR peaks, or the chemical shift of the solvent if the sample does not contain tetramethylsilane. Therefore, the ¹H NMR peak lists may, under certain circumstances, include the tetramethylsilane peak. The lists of 1 H-NMR peaks are equivalent to the classical ones. 1 H-NMR images and therefore usually contain all peaks that are seen in classical NMR images. 1 HN MR interpretations are also listed.

[0575] Furthermore, they can be used like classic 1 H-NMR representations show solvent signals, signals of stereoisomers of the compounds that may be the subject of the invention, and / or peaks of impurities.

[0576] 1H-NMR solvent signal c. The tetramethylsilane signal and the water signal in the respective solvent are excluded from the relative intensity calibration because the intensity values ​​given for them can be very high.

[0577] The peaks of stereoisomers of the invented compounds and / or peaks of impurities usually have a lower intensity than the peaks of the invented compounds (for example, at a purity of >90%).

[0578] Such stereoisomers and / or impurities can be typical for the respective manufacturing process. Their peaks can therefore help to identify the reproducibility of a manufacturing process based on “byproduct fingerprints”.

[0579] An expert who calculates the peaks of the target connections using known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can identify the peaks of the target connections as needed, possibly applying additional intensity filters. This identification is equivalent to the corresponding peak listing in the classical method. 1 HN MR interpretation.

[0580] The solvent used can be read from the JCAMP file using the parameter “solvent”, the measurement frequency of the spectrometer using “observe frequency”, and the spectrometer model using “spectrometer / data system”.

[0581] 13 C-NMR data are processed analogously to the 1 H-NMR data as peak lists from broadband-decoupled 13 C-NMR spectra are given. 13C-NMR solvent signals and tetramethylsilane are excluded from the relative intensity calibration because these signals can have very high intensity values.

[0582] Further details on NMR data description with peak lists can be found in: “Citation of NMR Peaklist Data within Patent Applications” in the Research Disclosure Database Number 564025.

[0583] The following manufacturing and use examples illustrate the invention without limiting it. Manufacturing examples

[0584] Synthesis example no. 1

[0585] Preparation of rac-(2S)-4-Hydroxy-N-[5-(ethoxyiminomethyl)-2-pyridyl]-6-oxo-2-[6-(trifluoro-methyl)-3-pyridyl]-2,3-dihydro-lH-pyridine-5-carboxamide (1-003)

[0586] Step 1: Synthesis of 5-(Ethoxyiminomethyl)pyridine-2-amine (IM036)

[0587] 6-Aminonicotinaldehyde (1.00 g, 8.18 mmol) was placed in pyridine (10 mL) and treated with ethoxyamine hydrochloride (968 mg, 9.82 mmol). The mixture was then stirred for 16 h at room temperature. The reaction mixture was evaporated under vacuum, and the residue was chromatographed on silica gel (gradient: dichloromethane / dichloromethane:methanol = 10:l). 1.35 g of 5-(ethoxyaminomethyl)pyridine-2-amine was obtained. HPLC-MS: logP = 1.08; mass (m / w): 166.4 [M+H] +

[0588] 'H-NMR (600 MHz, de-DMSO), peak list 5= 8.3884 (0.4); 8.3846 (0.5); 8.0312 (3.7); 8.0275 (3.8); 8.0213 (8.2); 8.0142 (0.5); 8.0033 (0.3); 7.9993 (0.3); 7.6445 (2.3); 7.6406 (2.3); 7.6300 (2.4); 7.6261 (2.4); 7.1876 (1.0); 6.5132 (0.5); 6.4618 (3.7); 6.4472 (3.9); 6.4307 (0.6); 6.4083 (3.9); 4.1198 (0.9); 4.1080 (0.9); 4.0852 (2.4); 4.0735 (7.7); 4.0618 (7.8); 4.0501 (2.6); 3.3343 (1.9); 2.5095 (2.9); 2.5066 (6.6); 2.5036 (9.4); 2.5006 (7.0); 2.4976 (3.4); 1.2658 (0.9); 1.2541 (1.9); 1.2424 (0.9); 1.2249 (7.8); 1.2132 (16.0); 1.2014 (7.8); -0.0002 (0.9)

[0589] Stufe 2: Synthese von rac-(2S)-4-Hydroxy-N-[5-(ethoxyiminomethyl)-2-pyridyl]-6-oxo-2-[6-(trifluoro- methyl)-3-pyridyl]-2,3-dihydro-lH-pyridine-5-carboxamide (1-003)

[0590] Ethyl rac-(2S)-4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carboxylate (known from WO2021261562) (100 mg, 0.30 mmol) was suspended in toluene (20 mL) and mixed with 5-(ethoxyiminomethyl)pyridine-2-amine (60.02 mg, 0.36 mmol) from Stufet. The mixture was then stirred under reflux for 2 hours using a water separator. After cooling, the solid was filtered off and the filtrate was evaporated under reduced pressure. The residue was purified by preparative HPLC (reversed phase, water / acetonitrile) to yield 46 mg of rac-(2S)-4-hydroxy-N-[5-(ethoxyimomethyl)-2-pyridyl]-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carboxamide. HPLC-MS: logP = 3.46; mass (m / w): 450.6 [M+H] +

[0591] 'H-NMR (600 MHz, d6-DMSO), peak list: 5= 17.2375 (0.6); 16.1209 (0.5); 12.5494 (0.5); 12.2891 (0.7); 9.6123 (0.6); 8.8377 (2.9); 8.8049 (0.4); 8.5168 (1.3); 8.4825 (0.6); 8.4690 (0.4); 8.3860 (0.3); 8.2525 (3.6); 8.1743 (0.5); 8.1264 (1.8); 8.0680 (2.7); 7.9686 (1.8); 7.9566 (1.7); 7.9419 (0.6); 5.1249 (0.6); 5.0154 (0.5); 4.2215 (0.6); 4.2095 (0.6); 4.1878 (2.1); 4.1761 (6.2); 4.1644 (6.3); 4.1527 (2.2); 4.1358 (0.4); 4.1242 (0.4); 3.3239 (28.5); 3.2008 (0.3); 3.1809 (0.4); 3.0775 (0.4); 3.0665 (0.4); 2.9130 (1.2); 2.5066 (39.1); 2.5038 (52.2); 2.5011 (40.8); 2.3882 (0.3); 2.0765 (4.4); 1.3075 (0.7); 1.2958 (1.4); 1.2840 (0.8); 1.2680 (7.9); 1.2562 (16.0); 1.2445 (8.0); 1.2385 (1.5); 1.2266 (0.6); -0.0002 (4.9)

[0592] Synthesebeispiel Nr. 2

[0593] Herstellung von Methyl rac-(2S)-5-[[5-(ethoxyiminomethyl)-2-pyridyl]carbamoyl]-4-hydroxy-6- oxo-2-[6-(trifhioromethyl)-3-pyridyl]-2,3-dihydropyridine-l-carboxylate (1-097) rac-(2S)-4-Hydroxy-N-[5-(ethoxyimomethyl)-2-pyridyl]-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carboxamide (90.0 mg, 0.20 mmol) from Synthesis Example 1, Step 2, were placed in in-THF (10 mL) and, at 0°C, first triethylamine (40.5 mg, 0.40 mmol) and then methyl chloroformate (18.9 mg, 0.20 mmol) were added. After warming to room temperature, the mixture was stirred for 16 hours. The reaction mixture was treated with dichloromethane (20 mL) and 10% hydrochloric acid (20 mL), the organic phase was separated, and the mixture was dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by preparative HPLC (reversed phase, water / acetonitrile), yielding 18 mg of methyl rac-(2S)-5-[[5-(ethoxyiminomethyl)-2-pyridyl]carbamoyl]-4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydropyridine-l-carboxylate. HPLC-MS: logP = 3.72; mass (m / w): 508.5 [M+H] +’H-NMR (600 MHz, d6-DMSO), peak list: 5= 11.9082 (0.1); 8.7795 (1.6); 8.7768 (1.6); 8.5584 (1.3); 8.2664 (3.3); 8.1014 (0.5); 8.0982 (0.6); 8.0867 (1.0); 8.0836 (1.1); 8.0556 (1.6); 8.0411 (0.9); 8.0039 (0.7); 8.0011 (0.7); 7.9904 (1.0); 7.9872 (1.0); 7.9167 (2.1); 7.9029 (1.6); 7.5393 (0.1); 5.8038 (0.7); 5.7938 (0.7); 5.7566 (7.8); 4.3094 (0.1); 4.2977 (0.4); 4.2917 (0.4); 4.2859 (0.5); 4.2798 (1.3); 4.2678 (1.6); 4.2662 (1.8); 4.2543 (1.4); 4.2482 (0.5); 4.2425 (0.4); 4.2363 (0.5); 4.2224 (0.2); 4.2106 (0.2); 4.1988 (0.1); 4.1889 (1.2); 4.1772 (3.6); 4.1655 (3.6); 4.1537 (1.2); 3.7911 (0.2); 3.3327 (1.2); 3.1453 (0.4); 3.1146 (0.4); 2.6168 (0.2); 2.6138 (0.3); 2.6107 (0.2); 2.5227 (0.4); 2.5196 (0.6); 2.5165 (0.7); 2.5076 (18.2); 2.5047 (38.1); 2.5017 (52.6); 2.4987 (38.7); 2.4958 (18.5); 2.3886 (0.2); 2.3857 (0.3); 2.3826 (0.2); 1.9091 (0.2); 1.3033 (0.2); 1.2915 (0.5); 1.2875 (0.2); 1.2837 (0.2); 1.2798 (0.3); 1.2754 (0.3); 1.2660 (7.9); 1.2542 (16.0); 1.2424 (7.7); 1.2252 (0.2); 1.1695 (0.3); 0.8538 (0.1); 0.0053 (0.5); - 0.0001 (13.8); -0.0056 (0.5).

[0594] Synthesis example no. 3

[0595] Preparation of rac-(2S)-4-Hydroxy-N-[5-(isobutoxyiminomethyl)-2-pyridyl]-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-lH-pyridine-5-carboxamide (1-072)

[0596] Step 1: Synthesis of tert-Butyl N-[5-(hydroxyiminomethyl)-2-pyridyl]carbamates tert-Butyl(5-formylpyridin-2-yl)carbamate (2.70 g, 11.8 mmol) was reacted in ethanol (20 mL) and pyridine (10 mL) and hydroxylammonium chloride (1.00 g, 14.3 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours, then evaporated to dryness under reduced pressure and the residue was stirred with water. The precipitated solid was filtered and dried, yielding 2.74 g of tert-butyl N-[5-(hydroxyiminomethyl)-2-pyridyl]carbamate.

[0597] 'H-NMR (600 MHz, d6-DMSO): 5= 1.48 (s, 9H), 7.83 (d, 1H), 7.95 (d, 1H), 8.11 (s, 1H), 8.39 (d, 1H), 9.95 (s, 1H), 11.24 (s, 1H).

[0598] Step 2: Synthesis of tert-Butyl N-[5-(2-cyanoethoxyiminomethyl)-2-pyridyl]carbamates tert-Butyl N-[5-(hydroxyiminomethyl)-2-pyridyl]carbamate (620 mg, 2.61 mmol) and cesium carbonate (1.700 g, 5.22 mmol) were placed in acetonitrile (20 mL) and 3-bromopropionitrile (1.050 g, 7.84 mmol) were added. The reaction mixture was stirred for 48 hours at 60°C and, after cooling, poured onto water (200 mL). The precipitated solid was filtered off and stirred with dichloromethane / methanol (9:1). The insoluble components were filtered off, the filtrate was concentrated, and the residue was separated chromatographically on silica gel (gradient: dichloromethane / ethyl acetate). 127 mg of tert-butyl N-[5-(2-cyanoethoxyiminomethyl)-2-pyridyl]carbamate were obtained. HPLC-MS: logP = 2.57; mass (m / w): 291.2 [M+H] +

[0599] 'H-NMR (600 MHz, CD3CN): 5= 1.51 (s, 9H), 2.80 (m, 2H), 4.30 (m, 2H), 7.83 (d, 1H), 7.97 (m, 2H), 8.15 (s, 1H), 8.44 (s, 1H).

[0600] Step 3: Synthesis of 3-[(6-Amino-3-pyridyl)methyleneamino]oxypropanenitrile (IM044) tert-Butyl N-[5-(2-cyanoethoxyiminomethyl)-2-pyridyl]carbamates (117.7 mg, 0.40 mmol) were placed in dichloromethane (4.0 mL) and treated with 0.155 mL (2.00 mmol) of trifluoroacetic acid. The reaction mixture was stirred at room temperature for 16 hours and then made basic with sodium carbonate. After phase separation using a Chromabond PTS cartridge, the solvent was evaporated under reduced pressure. 63.0 mg of 3-[(6-Amino-3-pyridyl)methyleneamino]oxypropanenitrile were obtained. HPLC-MS: logP = 0.83; mass (m / w): 191.2 [M+H] +

[0601] Step 4: Synthesis of rac-(2S)-4-Hydroxy-N-[5-(isobutoxyiminomethyl)-2-pyridyl]-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carboxamide (1-072)

[0602] 3-[(6-Amino-3-pyridyl)methyleneamino]oxypropanenitrile (60.5 mg, 0.31 mmol) from step 3 and rac-(2S)-4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carboxylate (90.0 mg, 0.27 mmol) were reacted analogously to Example 1, step 2. 71.6 mg of rac-(2S)-4-hydroxy-N-[5-(isobutoxyiminomethyl)-2-pyridyl]-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carboxamide were obtained. HPLC-MS: logP = 2.57; Mass (m / z): 476.2 [M+H] +

[0603] 'H-NMR (600 MHz, d6-DMSO), peak list: 5= 17.2033 (0.4); 12.3141 (0.4); 9.6248 (0.4); 8.8826 (0.4); 8.8402 (5.5); 8.5718 (2.4); 8.5365 (0.3); 8.4927 (0.3); 8.3716 (8.0); 8.2405 (0.6); 8.1382 (3.3); 8.1264

[0604] (3.2); 8.0996 (4.8); 7.9701 (3.9); 7.9565 (3.4); 7.6398 (0.7); 7.4984 (0.5); 5.7583 (2.5); 5.1189 (0.5); 5.0710 (0.3); 5.0307 (0.4); 4.3749 (0.8); 4.3649 (1.6); 4.3550 (0.9); 4.3227 (6.8); 4.3128 (13.5); 4.3030

[0605] (7.3); 4.2931 (1.1); 4.2822 (0.5); 3.3281 (11.0); 3.0685 (0.4); 3.0580 (0.4); 3.0488 (0.4); 2.9922 (1.2); 2.9822 (2.2); 2.9724 (1.4); 2.9564 (8.3); 2.9465 (16.0); 2.9367 (8.5); 2.5268 (0.4); 2.5238 (0.5); 2.5206 (0.6); 2.5118 (13.4); 2.5088 (29.2); 2.5058 (40.8); 2.5028 (29.3); 2.4998 (13.5); 2.4651 (0.7); 2.4546 (1.2); 2.4437 (0.5); 2.3013 (0.4); 2.0785 (0.6); 1.2436 (13.5); 1.2349 (2.9)

[0606] Synthesis example no. 4

[0607] Preparation of ethyl [[6-[[rac-(2S)-4-hydroxy-6-oxo-2-[6-(trifhioromethyl)-3-pyridyl]-2,3-dihydro-lH-pyridine-5-carbonyl]amino]-3-pyridyl]methyleneamino] carbonate (1-075) and ethyl rac-(2S)-5-[[5-(ethoxycarbonyloxyiminomethyl)-2-pyridyl]carbamoyl]-4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl] -2, 3-dihydropyridine-l -carboxylates (1-076)

[0608] Step 1: Synthesis of 6-Aminopyridine-3-carbaldehyde oximes 6-Aminonicotinaldehyde (2.00 g, 16.3 mol) was placed in a mixture of pyridine (12 mL) and ethanol (12 mL), then treated with hydroxylammonium chloride (1.707 g, 24.5 mmol) and stirred at room temperature for 5 hours. The reaction mixture was evaporated under vacuum, the residue was stirred with water (50 mL), and the precipitate was filtered off. After drying, 2.04 g of 6-aminopyridine-3-carbaldehyde oximes were obtained. HPLC-MS: logP = 0.32; mass (m / z): 138.1 [M+H] +

[0609] Step 2: Synthesis of rac-(2S)-4-Hydroxy-N-[5-(hydroxyiminomethyl)-2-pyridyl]-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihy dro- 1 H-pyridine-5-carboxamide (1-032)

[0610] 6-Aminopyridine-3-carbaldehyde oximes (415.2 mg, 3.02 mmol) from step 1 and rac-(2S)-4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carboxylate (90.0 mg, 0.27 mmol) were reacted analogously to Step 2 of Example 1. 1.01 g of rac-(2S)-4-hydroxy-N-[5-(hydroxyiminomethyl)-2-pyridyl]-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carboxamide were obtained. HPLC-MS: logP = 2.06; mass (m / w): 422.2 [M+H] +

[0611] 'H-NMR (600 MHz, d6-DMSO), peak list: 5= 17.3047 (0.9); 16.1966 (0.8); 16.1853 (0.8); 16.1748 (0.8); 12.5133 (1.0); 12.4140 (0.3); 12.4109 (0.3); 12.3568 (0.4); 12.2768 (1.4); 11.4012 (10.1); 10.7918 (2.0); 10.7849 (1.9); 9.5937 (1.3); 8.8421 (13.0); 8.5216 (9.3); 8.1705 (13.8); 8.1652 (13.6); 8.1301

[0612] (7.8); 8.0578 (16.0); 8.0208 (2.4); 7.9645 (8.5); 7.9585 (9.4); 7.6578 (1.0); 7.6507 (0.9); 7.6471 (1.0); 7.6442 (1.0); 7.2447 (0.3); 7.1773 (0.4); 6.4922 (1.0); 6.4853 (1.1); 6.4782 (1.1); 6.4718 (1.0); 6.3936

[0613] (1.8); 5.1067 (1.8); 5.0439 (1.4); 3.3400 (3.6); 3.1779 (1.0); 3.0846 (1.0); 3.0572 (1.2); 3.0274 (1.1); 2.9979 (1.1); 2.9228 (2.8); 2.5075 (44.0); 2.3021 (1.1); 2.2964 (1.1); -0.0002 (8.0); -0.0039 (6.5); - 0.0071 (7.8)

[0614] Stufe 3: Synthese von Ethyl [[6-[[rac-(2S)-4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3- dihydro-lH-pyridine-5-carbonyl]amino]-3-pyridyl]methyleneamino] carbonate (1-075) und Ethyl rac- (2S)-5-[[5-(ethoxycarbonyloxyiminomethyl)-2-pyridyl]carbamoyl]-4-hydroxy-6-oxo-2-[6- (trifluoromethyl)-3-pyridyl]-2,3-dihydropyridine-l-carboxylate (1-076) rac-(2S)-4-Hydroxy-N-[5-(hydroxyiminomethyl)-2-pyridyl]-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carboxamide (151.0 mg, 0.35 mmol) were placed in dichloromethane (10 mL) and treated with triethylamine (90.02 mg, 0.89 mmol) at 0°C, followed by the slow addition of ethyl chloroformate (46.67 mg, 0.43 mmol). After 16 stirrings at room temperature, the mixture was diluted with dichloromethane, washed with 10% hydrochloric acid, and filtered through a Chromabond PTS cartridge. The solvent was evaporated under reduced pressure and the residue was purified by preparative HPLC (reversed phase, water / acetonitrile), yielding 37.5 mg ethyl [[6-[[rac-(2S)-4-hydroxy- 6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carbonyl]amino]-3-pyridyl]methyleneamino] carbonate and 24.3 mg ethyl rac-(2S)-5-[[5-

[0615] (ethoxy carbony loxyiminomethyl)-2-pyridyl]carbamoyl] -4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3- pyridyl]-2,3-dihydropyridine-l-carboxylate erhalten wurden.

[0616] 1-075: HPLC-MS: logP = 3,03; Masse (m / z): 494,5 [M+H] +

[0617] 'H-NMR (600 MHz, d6-DMSO), peak list: 5= 17.0615 (0.2); 12.6715 (0.1); 12.3876 (0.2); 9.6648 (0.1); 8.8363 (1.7); 8.7198 (2.6); 8.6329 (0.9); 8.1960 (1.0); 8.1755 (0.7); 8.1337 (0.9); 8.1240 (0.9); 7.9681 (1.2); 7.9546 (1.0); 5.7564 (0.1); 5.1215 (0.2); 5.0229 (0.2); 4.2904 (2.0); 4.2786 (6.3); 4.2667 (6.4); 4.2549 (2.1); 3.3180 (50.0); 3.2945 (0.6); 3.1730 (0.1); 3.1644 (0.1); 3.1029 (0.1); 3.0908 (0.2); 2.9228 (0.4); 2.6167 (0.3); 2.6136 (0.4); 2.6105 (0.3); 2.5226 (0.5); 2.5196 (0.6); 2.5164 (0.7); 2.5077 (21.5); 2.5046 (47.2); 2.5016 (66.5); 2.4985 (48.4); 2.4955 (22.4); 2.3886 (0.3); 2.3855 (0.4); 2.3824 (0.3); 1.9090 (0.2); 1.2969 (7.7); 1.2850 (16.0); 1.2732 (7.6); 1.2339 (0.3); 1.1857 (0.1); 1.1773 (0.1); 1.1736 (0.2); 0.0053 (0.7); -0.0001 (22.3); -0.0057 (0.7)

[0618] 1-076: HPLC-MS: logP = 3,55; Masse (m / z): 566,5 [M+H] +

[0619] 'H-NMR (600 MHz, d6-DMSO): 5= 12,01 (s, 1H), 8.73 (m, 3H), 8.24 (m, 1H), 8.14 (m, 1H), 8.01 (m, 1H), 7.91 (m, 1H), 5.80 (m, 1H), 4.26 (m, 4H), 3.35 (m, 1H), 3.14 (m, 1H), 1.26 (m, 6H).

[0620] Synthesebeispiel Nr. 5

[0621] Herstellung von [[6-[[rac-(2S)-4-Hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro- lH-pyridine-5-carbonyl]amino]-3-pyridyl]methyleneamino] methanesulfonate (1-065) rac-(2S)-4-Hydroxy-N-[5-(hydroxyiminomethyl)-2-pyridyl]-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carboxamide (100.0 mg, 0.35 mmol) from Synthesis Example 4, Step 2, were placed in dichloromethane (10 mL) and treated with triethylamine (90.02 mg, 0.89 mmol) at 0°C, followed by the slow addition of methanesulfonic acid chloride (32.6 mg, 0.28 mmol). After 16 stirrings at room temperature, the mixture was diluted with dichloromethane, washed with 10% hydrochloric acid, and filtered through a Chromabond PTS cartridge. The solvent was evaporated under reduced pressure and the residue purified on silica gel (gradient: dichloromethane / dichloromethane:methanol = l:l), yielding 35.0 mg [[6-[[rac-(2S)-4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-lH-pyridine-5-carbonyl]amino]-3-pyridyl]methyleneamino] methanesulfonate. HPLC-MS: logP = 2.53; mass (m / w): 500.3 [M+H] +

[0622] Synthesis example no. 6

[0623] Methyl N-iso-propoxy-4-[[rac-4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro- 1 H-pyridine-5-carbonyl] amino] benzenecarboximidate (1-071)

[0624] Step 1: Synthesis of N-isoPropoxy-l-(4-nitrophenyl)methanimine

[0625] O-isopropylhydroxylamine hydrochloride (1.12 g, 10.0 mmol) was slowly added to a solution of 4-nitrobenzaldehyde (1.00 g, 6.6 mmol) in pyridine (10 mL) and stirred overnight at room temperature. After distilling off the solvent under reduced pressure, the residue was dissolved in water and sonicated. The solid was filtered off, washed with water, and dried. 1.32 g of N-iso-propoxy-l-(4-nitrophenyl)methanimine was obtained.

[0626] HPLC-MS: logP = 3.61; Mass (m / z): 209.0 [M+H] + ;

[0627] Step 2: Synthesis of N-Isopropoxy-4-nitro-benzimidoyl chloride

[0628] To a solution of N-isopropoxy-l-(4-nitrophenyl)methanimine (1.32 g, 5.70 mmol) in dimethylformamide (30 mL) at 0°C, N-chlorosuccinimide (2.3 g, 17.1 mmol) was added portionwise and stirred at room temperature for 48 hours. The reaction mixture was diluted with ethyl acetate, washed with water, the organic phase was removed, dried over magnesium sulfate, and rotated. 355 mg of N-isopropoxy-4-nitrobenzimidoyl chloride were obtained, which was reacted directly without purification.

[0629] Step 3: Synthesis of Methyl N-iso-Propoxy-4-nitro-benzenecarboximidate

[0630] Dry methanol (91 pL, 2.3 mmol) was added dropwise to a 60% sodium hydride solution (135 mg, 3.4 mmol) in dry tetrahydrofuran (10 mL) at 0°C under argon and stirred at room temperature for 3 hours. The reaction mixture was then treated at 0°C with N-isopropoxy-4-nitrobenzimidoyl chloride (175 mg, 0.75 mmol) and stirred overnight at room temperature. After dilution with ethyl acetate, the mixture was washed with saturated saline, the organic phase was removed, dried over magnesium sulfate, and rotated. The residue was chromatographed with cyclohexane / ethyl acetate as the mobile phase. 144 mg of methyl N-isopropoxy-4-nitrobenzenecarboximidate were obtained. HPLC-MS: logP = 3.82; mass (m / w): 239.0 [M+H] + Step 4: Synthesis of Methyl 4-Amino-N-isopropoxy-benzenecarboximidate (IM-053)

[0631] To a solution of methyl N-isopropoxy-4-nitrobenzenecarboximidate (144 mg, 0.75 mmol) in ethanol (2.5 mL), iron powder (148 mg, 2.6 mmol) and hydrochloric acid (1.7 mL, 1.7 mmol) were added at 70°C and stirred for 3 hours at 70°C. After cooling, the reaction mixture was quenched with sodium hydroxide (20 mL), diluted with ethyl acetate, the organic phase was separated, and dried over magnesium sulfate. 78 mg of methyl 4-amino-N-isopropoxybenzenecarboximidate were obtained. HPLC-MS: logP = 3.82; mass (m / z): 209.3 [M+H] +

[0632] Step 5: Synthesis of Methyl N-isoPropoxy-4-[[rac-4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridy 1] -2,3 -dihy dro- 1 H-pyridine-5 -carbonyl] amino]benzenecarboximidate (1-071)

[0633] Methyl 4-amino-N-isopropoxy-benzenecarboximidate (122 mg, 0.41 mmol) from step 4 and rac-(2S)-4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carboxylate (138 mg, 0.41 mmol) were reacted analogously to Example 1, step 2. 70 mg of methyl N-isopropoxy-4-[[rac-4-hydroxy-6-oxo-2-[6-(trifluoromethyl)-3-pyridyl]-2,3-dihydro-1H-pyridine-5-carbonyl]amino]benzenecarboximidate was obtained. HPLC-MS: logP = 4.61; mass (m / w): 491.4 [M+H] + 1H NMR (D6-DMSO), peak list: 5= 17.6738 (0.3); 16.4646 (0.5); 12.2495 (0.4); 12.2431 (0.4); 12.0403 (0.4); 8.8390 (0.8); 8.8276 (0.9); 8.1386 (0.4); 8.1234 (0.8); 8.1086 (0.5); 7.9760 (0.7); 7.9622 (1.3); 7.9485 (0.6); 7.8099 (0.9); 7.7948 (1.6); 7.7781 (1.0); 7.6441 (0.9); 7.6297 (0.8); 7.5942 (0.9); 7.5800 (0.8); 5.0013 (0.4); 4.1876 (0.7); 4.1773 (1.0); 4.1670 (0.7); 3.7539 (5.5); 3.7502 (5.1); 3.3171 (9.9); 3.2935 (3.8); 2.9085 (0.4); 2.9005 (0.7); 2.8863 (0.4); 2.6133 (0.4); 2.5224 (0.4); 2.5193 (0.5); 2.5161 (0.6); 2.5074 (20.2); 2.5044 (44.2); 2.5013 (60.9); 2.4982 (42.5); 2.4952 (18.8); 2.3853 (0.4); 1.2174 (16.0); 1.2070 (15.9); 0.0053 (1.7); -0.0001 (57.5); -0.0057 (1.7)

[0634] Synthesebeispiel Nr. 7 rac-(2S)-2-(4-Cyano-3-fluoro-phenyl)-4-hydroxy-N-[5-(isobutoxyiminomethyl)-2-pyridyl]-6-oxo- 2,3-dihydro-l H-pyridine-5-carboxamid (1-109)

[0635] Stufe 1: Synthese von rac-(3R)-3-Amino-3-(4-bromo-3-fluoro-phenyl)propyl Carbonsäure

[0636] Malonic acid (13.53 g, 130 mmol) and ammonium acetate (15.04 g, 195 mmol) were successively added to a solution of 4-bromo-3-fluorobenzaldehyde (13.2 g, 65 mmol) in ethanol (100 mL) and then stirred at reflux for 16 hours. The reaction mixture was cooled to room temperature, the precipitated solid was filtered off, washed with ethanol, and dried. 16.67 g of rac-(3R)-3-amino-3-(4-bromo-3-fluoro-phenyl)-propyl carboxylic acid were obtained, which was reacted directly. HPLC-MS: logP = 0.39; mass (m / w): 262.0 [M+H] +

[0637] Step 2: Synthesis of ethyl rac-(3R)-3-amino-3-(4-bromo-3-fluoro-phenyl)propanoate rac-(3R)-3-Amino-3-(4-Bromo-3-Fluoro-Phenyl)-Propyl carboxylic acid (16.7 g, 63.7 mmol) from step 1 was suspended in ethanol (130 mL) and thionyl chloride (9.49 mL, 127 mmol) was slowly added dropwise. The mixture was then stirred at reflux for 2 hours. After cooling to room temperature, the reaction mixture was completely evaporated under vacuum. 22.0 g of ethyl rac-(3R)-3-amino-3-(4-bromo-3-fluoro-phenyl)propanoate were obtained, which was reacted directly. HPLC-MS (neutral): logP = 2.30; mass (m / w): 291.9 [M+H] + HO

[0638] Step 3: Synthesis of ethyl rac-(3R)-3-(4-bromo-3-fluoro-phenyl)-3-[(3-ethoxy-3-oxo-propanoyl)amino]propanoate rac-(3R)-3-Amino-3-(4-bromo-3-fluorophenyl)propanoate from step 2 (22.0 g, 63.9 mmol) was placed in chloroform (150 mL) and successively treated with triethylamine (8.92 mL, 63.9 mmol), l-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (HCl salt) (18.4 g, 95.9 mmol), and 4-(Dimethylamino)pyridine (11.73 g, 95.9 mmol). The mixture was then stirred for 2 hours at room temperature. The solvent was distilled off under vacuum, the residue was diluted with dichloromethane, washed several times with 10% hydrochloric acid, and finally with saturated sodium chloride solution, and dried over sodium sulfate. The solvent was distilled off under vacuum and the residue was chromatographed on silica gel (gradient: hexane / ethyl acetate), yielding 25.0 g of ethyl rac-(3R)-3-(4-bromo-3-fluorophenyl)-3-[(3-ethoxy-3-oxo-propanoyl)amino]propanoate. HPLC-MS (neutral): logP = 2.62; mass (m / w): 405.9 [M+H] +

[0639] Stage 4: Synthesis of Ethyl rac-(2R)-2-(4-bromo-3-fluoro-phenyl)-4-hydroxy-6-oxo-2,3-dihydro-lH-pyridine-5-carboxy lat

[0640] Ethyl rac-(3R)-3-(4-bromo-3-fluorophenyl)-3-[(3-ethoxy-3-oxo-propanoyl)amino]propanoate from step 4 (25.0 g, 61.8 mmol) was placed in ethanol (120 mL) and a 21% sodium ethylate solution in ethanol (23 mL, 61.8 mmol) was added dropwise under an argon atmosphere. The mixture was then stirred for 2 hours at 70°C. After cooling, the solvent was distilled off under vacuum, the residue was dissolved in 150 mL of water, and extracted with toluene. The aqueous phase was acidified with 10% hydrochloric acid, the precipitated solid was filtered off, and stirred for 3 hours in 80 mL of methyl tert-butyl ether. The product was filtered and dried, yielding 7.10 g of ethyl rac-(2R)-2-(4-bromo-3-fluoro-phenyl)-4-hy droxy-6-oxo-2,3-dihy dro-1 H-pyridine-5-carboxy lat.

[0641] HPLC-MS (neutral): logP = 0.75; Mass (m / z): 359.1 [M+H] +

[0642] Step 5: Synthesis of rac-(2R)-2-(4-Bromo-3-fluoro-phenyl)-N-(5-formyl-2-pyridyl)-4-hydroxy-6-oxo-2, 3-dihydro-lH-pyridine-5-carboxamide

[0643] Ethyl rac-(2R)-2-(4-bromo-3-fluorophenyl)-4-hydroxy-6-oxo-2,3-dihydro-1H-pyridine-5-carboxylate from step 4 (400 mg, 1.11 mmol) was suspended in toluene (30 mL), treated with 6-aminonicotinaldehyde (136.4 mg, 1.11 mmol), and then stirred for 1 hour at 20°C. After cooling, the precipitated solid was filtered off and washed with hexane, yielding 255.0 mg of rac-(2R)-2-(4-bromo-3-fluorophenyl)-N-(5-formyl-2-pyridyl)-4-hydroxy-6-oxo-2,3-dihydro-1H-pyridine-5-carboxyamide. HPLC-MS (acidic): logP = 3.00; Mass (m / z): 436.0 [M+H] +

[0644] Step 6: Synthesis of rac-(2R)-2-(4-Bromo-3-fluoro-phenyl)-4-hydroxy-N-[5-(isobutoxyiminomethyl)-2-pyridyl]-6-oxo-2,3-dihydro-lH-pyridine-5-carboxamide (1-127) rac-(2R)-2-(4-Bromo-3-fluoro-phenyl)-N-(5-formyl-2-pyridyl)-4-hydroxy-6-oxo-2,3-dihydro-lH- pyridine-5-carboxamide from step 5 (200 mg, 0.46 mmol) was placed in pyridine (12 mL) and ethanol (5 mL), then mixed with O-isobutylhydroxylamine hydrochloride (87.65 mg, 69.0 mmol) and stirred for 18 hours at room temperature. The reaction mixture was evaporated under vacuum, the residue absorbed onto silica gel and chromatographed on silica gel (gradient: dichloromethane / 2-propanol), yielding 175 mg of rac-(2R)-2-(4-bromo-3-fluorophenyl)-4-hydroxy-N-[5-(isobutoxyiminomethyl)-2-pyridyl]-6-oxo-2,3-dihydro-1H-pyridine-5-carboxamide. HPLC-MS (acidic): logP = 5.08; mass (m / w): 507.2 [M+H] +

[0645] Stufe 7: Synthese von rac-(2R)-2-(4-Cyano-3-fluoro-phenyl)-4-hydroxy-N-[5- (isobutoxyiminomethyl)-2-pyridyl]-6-oxo-2,3-dihydro-lH-pyridine-5-carboxamid (1-109)

[0646] In a microwave vessel under an argon atmosphere, rac-(2R)-2-(4-Bromo-3-fluoro-phenyl)- 4-hydroxy-N- [5 -(isobutoxy im inomethyl l)-2 -pyridyl] -6-oxo-2,3-dihydro- 1 H-pyridine-5 -carboxamide (195 mg, 0.38 mmol) from step 6, zinc cyanide (45.3 mg, 0.38 mmol), 1,1 '- Bis(diphenylphosphino)ferrocene (21.39 mg, 0.03 mmol), Tris(dibenzylideneacetone)dipalladium (21.39 mg, 0.03 mmol) and N,N-diisopropylethylamine (99.75 mg, 0.77 mmol) were placed in dry N,N-dimethylformamide (10 mL). The reaction mixture was heated in a microwave at 120°C for 1 hour. After cooling, the DMF was distilled off under reduced pressure, the residue was mixed with water, acidified with 10% hydrochloric acid, and extracted several times with dichloromethane.The organic phases were dried, concentrated, the residue absorbed onto silica gel, and chromatographed on silica gel (gradient: dichloromethane / 2-propanol), yielding 42.0 mg of rac-(2R)-2-(4-cyano-3-fluoro-phenyl)-4-hydroxy-N-[5-(isobutoxyiminomethyl)-2-pyridyl]-6-oxo-2,3-dihydro-1H-pyridine-5-carboxamide. HPLC-MS (acidic): logP = 4.30; mass (m / w): 452.6 [M+H]. +

[0647] By analogy to the examples and according to the manufacturing processes described above, the compounds of formula (I) listed in Table 1 can be obtained:

[0648] Table 1

[0649]

[0650]

[0651]

[0652]

[0653] Table 2 (Intermediate)

[0654] 1) The specified mass corresponds to the signal from the isotopic pattern of [M+H] + Ions with the highest intensity. # means that the [MH]' ion was absorbed.

[0655] Application examples

[0656] Frankliniella occidentalis - Spray test

[0657] Solvent: 78.0 parts by weight acetone

[0658] 1.5 parts by weight of dimethylformamide

[0659] Emulsifier: Alkylaryl polyglycol ether

[0660] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations were prepared by dilution with water containing emulsifier.

[0661] Bean leaf discs (Phaseolus vulgaris) were sprayed with an active ingredient preparation of the desired concentration and subsequently infected with all stages of the California flower thrips (Frankliniella occidentalis).

[0662] After 7 days, the effectiveness was determined as a percentage of leaf protection. 100% effectiveness means that no leaf damage is visible (very good leaf protection) and 0% means that the leaf disc is damaged to the same extent as the untreated control (no leaf protection).

[0663] In this test, z. For example, the following compounds from the production examples provide 100% good leaf protection at an application rate of 500 g / ha: 1-002, 1-003, 1-004, 1-005, 1-006, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-022, 1-026, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-042, 1-043, 1-044, 1-046, 1-047, 1-049, 1-050, 1-051, 1-054, 1-056, 1-060, 1-061, 1-062, 1-063, 1-064, 1-065, 1-067, 1-072, 1-073, 1-075, 1-076, 1-077, 1-078, 1-080, 1-083, 1-084, 1-085, 1-087, 1-088, 1-091, 1-093, 1-094, 1-095, 1-096, 1-100, 1-101, 1-103, 1-105, 1-112, 1-113, 1-114, 1-115, 1-119 1-126, 1-127, 1-131, 1-133, 1-138, 1-142, 1-143, 1-144, 1-146, 1-147, 1-151, 1-154, 1-156, 1-157, 1-158, 1-160, 1-161.

[0664] In this test, for example, the following compounds from the production examples showed good leaf protection of 90% at an application rate of 500 g / ha: 1-001, 1-007, 1-021, 1-040, 1-052, 1-055, 1-079, 1-092, 1-102, 1-104, 1-106, 1-107, 1-109, 1-123, 1-124, 1-130, 1-150, 1-153.

[0665] In this test, for example, the following compounds from the production examples showed good leaf protection of 80% at an application rate of 500 g / ha: 1-037, 1-039, 1-048, 1-066, 1-069, 1-108, 1-120, 1-128. In this test, the following compounds showed... For example, the following compounds from the production examples provide 100% good leaf protection at an application rate of 100 g / ha: 1-002, 1-003, 1-004, 1-005, 1-006, 1-008, 1-009, 1-010, 1-011, 1-012, 1-014, 1-022, 1-026, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-042, 1-043, 1-044, 1-046, 1-047, 1-050, 1-054, 1-055, 1-056, 1-057, 1-060, 1-061, 1-062, 1-063, 1-064, 1-065, 1-067, 1-072, 1-075, 1-077, 1-078, 1-080, 1-083, 1-085, 1-087, 1-088, 1-091, 1-093, 1-094, 1-095, 1-096, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-107, 1-109, 1-112, 1-113, 1-114, 1-115, 1-119, 1-120, 1-121, 1-123, 1-126, 1-127, 1-130, 1-131, 1-136, 1-138, 1-142, 1-143, 1-146, 1-147, 1-151, 1-153, 1-154, 1-156, 1-157, 1-158, 1-160, 1-161.

[0666] In this test, for example, the following compounds from the production examples showed good leaf protection of 90% at an application rate of 100 g / ha: 1-001, 1-007, 1-013, 1-015, 1-040, 1-051, 1-052, 1-053, 1-066, 1-068, 1-076, 1-078, 1-079, 1-084, 1-097, 1-117, 1-118, 1-124, 1-128, 1-129, 1-133, 1-144.

[0667] In this test, for example, the following compounds from the production examples showed good leaf protection of 80% at an application rate of 100 g / ha: 1-048, 1-092, 1-116, 1-122, 1-137, 1-139.

[0668] Myzus persicae - Spray test

[0669] Solvent: 78.0 parts by weight acetone

[0670] 1.5 parts by weight of dimethylformamide

[0671] Emulsifier: Alkylaryl polyglycol ether

[0672] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations were prepared by dilution with water containing emulsifier.

[0673] Chinese cabbage leaf slices (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) were sprayed with an active ingredient preparation of the desired concentration.

[0674] After 5 days, the effectiveness was determined as a percentage. 100% means that all aphids were killed; 0% means that no aphids were killed.

[0675] In this test, for example, the following compounds from the production examples showed an effect of 90% at an application rate of 500 g ai / ha: 1-102.

[0676] In this test, for example, the following compounds from the production examples showed an efficacy of 80% at an application rate of 500 g ai / ha: 1-039. Myzus persicae - Oral test

[0677] Solvent: 100 parts by weight acetone

[0678] To prepare a suitable active ingredient formulation, 1 part by weight of active ingredient was dissolved with the specified parts by weight of solvent and made up with water until the desired concentration was reached.

[0679] 50 jl of the active ingredient preparation were transferred to microtiter plates and made up to a final volume of 200 pl with 150 pl of IPL41 insect medium (33% + 15% sugar). The plates were then sealed with Parafdm, through which a mixed population of the green peach aphid (Myzus persicae), located in a second microtiter plate, was able to penetrate and ingest the solution.

[0680] After 5 days, the effectiveness was determined as a percentage. 100% means that all aphids were killed; 0% means that no aphids were killed.

[0681] In this test, for example, the following compounds from the production examples showed an efficacy of 95% at an application rate of 20 ppm: 1-130, 1-143.

[0682] In this test, for example, the following compounds from the production examples showed an effect of 90% at an application rate of 20 ppm: 1-124.

[0683] Nezara viridula - Spray test

[0684] Solvent: 78.0 parts by weight acetone

[0685] 1.5 parts by weight of dimethylformamide

[0686] Emulsifier: Alkylaryl polyglycol ether

[0687] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations were prepared by dilution with water containing emulsifier.

[0688] Barley plants (Hordeum vulgare) were sprayed with an active ingredient preparation of the desired concentration and infected with larvae of the green rice bug (Nezara viridula).

[0689] After 4 days, the effectiveness was determined as a percentage. 100% means that all rice bugs were killed; 0% means that no rice bugs were killed. In this test, the following results were shown: For example, the following compounds from the production examples have an effect of 100% at an application rate of 500 g / ha: 1-001, 1-002, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-024, 1-028, 1-030, 1-031, 1-034, 1-035, 1-039, 1-042, 1-043, 1-044, 1-046, 1-047, 1-050, 1-052, 1-056, 1-060, 1-062, 1-063, 1-064.

[0690] In this test, for example, the following compounds from the production examples showed an effect of 90% at an application rate of 500 g / ha: 1-033, 1-040, 1-053.

[0691] In this test, for example, the following compounds from the production examples showed an effect of 100% at an application rate of 100 g / ha: 1-001, 1-002, 1-003, 1-004, 1-005, 1-006, 1-008, 1-009, 1-010, 1-011, 1-012, 1-032, 1-033, 1-036, 1-043, 1-044, 1-047, 1-050, 1-060, 1-062, 1-065, 1-072.

[0692] In this test, for example, the following compounds from the production examples showed an effect of 90% at an application rate of 100 g / ha: 1-024, 1-026, 1-031, 1-039, 1-042, 1-052.

[0693] Euschistus heros - Spray test

[0694] Solvent: 78.0 parts by weight acetone

[0695] 1.5 parts by weight of dimethylformamide

[0696] Emulsifier: Alkylaryl polyglycol ether

[0697] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations were prepared by dilution with water containing emulsifier.

[0698] Barley plants (Hordeum vulgare) were sprayed with an active ingredient preparation of the desired concentration and infected with larvae of the brown stink bug (Euschistus heros).

[0699] After 7 days, the effectiveness was determined as a percentage. 100% means that all stink bugs were killed; 0% means that no stink bugs were killed.

[0700] In this test, for example, the following compounds from the production examples showed an efficacy of 100% at an application rate of 500 g / ha: 1-036, 1-108, 1-109, 1-113, 1-115, 1-133, 1-136, 1-144, 1-157. In this test, for example, the following compounds from the production examples showed an efficacy of 90% at an application rate of 500 g / ha: 1-022, 1-122, 1-126, 1-130, 1-135, 1-138, 1-154, 1-160. In this test, the following compounds from the production examples showed an efficacy of 90% at an application rate of 500 g / ha: 1-022, 1-122, 1-126, 1-130, 1-135, 1-138, 1-154, 1-160. B. the following compounds of the production examples have an effect of 100% at an application rate of 100 g / ha: 1-032, 1-072, 1-113, 1-115, 1-139.

[0701] In this test, for example, the following compounds from the production examples showed an effect of 90% at an application rate of 100 g / ha: 1-036, 1-108, 1-124, 1-126, 1-135, 1-138.

[0702] Nilaparvata lugens - Spray test

[0703] Solvent: 78.0 parts by weight acetone

[0704] 1.5 parts by weight of dimethylformamide

[0705] Emulsifier: Alkylaryl polyglycol ether

[0706] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations were prepared by dilution with water containing emulsifier.

[0707] Rice plants (Oryza sativa) were sprayed with the active ingredient preparation of the desired concentration and then infected with the brown-backed rice leafhopper (Nilaparvata lugens).

[0708] After 4 days, the effect was determined as a percentage. 100% means that all rice leafhoppers were killed; 0% means that no rice leafhoppers were killed.

[0709] In this test, for example, the following compounds from the production examples showed an effect of 100% at an application rate of 500 g / ha: 1-001, 1-002, 1-003, 1-005, 1-006, 1-008, 1-009, 1-011, 1-012, 1-032, 1-043, 1-044, 1-062, 1-065, 1-068, 1-072, 1-075, 1-078, 1-120, 1-122, 1-124, 1-130, 1-133, 1-137, 1-143, 1-144, 1-151.

[0710] In this test, for example, the following compounds from the production examples showed an effect of 90% at an application rate of 500 g / ha: 1-026, 1-047, 1-054, 1-073, 1-099, 1-103, 1-157, 1-160.

[0711] In this test, for example, the following compounds from the production examples showed an effect of 100% at an application rate of 100 g / ha: 1-001, 1-002, 1-003, 1-005, 1-009, 1-032, 1-043, 1-044, 1-047, 1-062, 1-072, 1-120, 1-123, 1-124, 1-133, 1-137, 1-143, 1-151.

[0712] In this test, for example, the following compounds from the production examples showed an effect of 90% at an application rate of 100 g / ha: 1-006, 1-008, 1-011, 1-028, 1-122.

[0713] Diabrotica balteata - Spray test solvent: 78 parts by weight acetone

[0714] 1.5 parts by weight of dimethylformamide

[0715] Emulsifier: Alkylaryl polyglycol ether

[0716] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations were prepared by dilution with water containing emulsifier.

[0717] Pre-soaked wheat kernels (Triticum aestivum) were incubated for one day in a multiwell plate filled with agar and a small amount of water (5 kernels per cavity). The germinated wheat kernels were injected with an active ingredient preparation of the desired concentration. Subsequently, each cavity was infested with 10-20 beetle larvae of Diabrotica balteata.

[0718] After 7 days, the effect was determined as a percentage. 100% means that all wheat plants grew as in the untreated, uninfected control; 0% means that no wheat plants grew.

[0719] In this test, for example, the following compounds from the production examples showed an efficacy of 100% at an application rate of 500 g / ha (= 160 pg / cavity): 1-142. In this test, for example, the following compounds from the production examples showed an efficacy of 80% at an application rate of 500 g / ha (= 160 pg / cavity): 1-110, 1-111.

[0720] Spodoptera frugiperda - Spray test

[0721] Solvent: 78.0 parts by weight acetone

[0722] 1.5 parts by weight of dimethylformamide

[0723] Emulsifier: Alkylaryl polyglycol ether

[0724] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations were prepared by dilution with water containing emulsifier.

[0725] Corn leaf discs (Zea mays) were sprayed with an active ingredient preparation of the desired concentration and, after drying, inoculated with armyworm caterpillars (Spodoptera frugiperda). After 7 days, the efficacy was determined as a percentage. 100% means that all caterpillars were killed; 0% means that no caterpillars were killed.

[0726] In this test, for example, the following compounds from the production examples showed an effect of 100% at an application rate of 500 g / ha: 1-001, 1-002, 1-005, 1-009, 1-011, 1-022, 1-029, 1-030, 1-031, 1-049, 1-050, 1-061, 1-091, 1-132, 1-133, 1-139, 1-143, 1-144, 1-153, 1-161.

[0727] Nilaparvata lugens - Test

[0728] Solvent: 14 parts by weight dimethylformamide

[0729] Emulsifier: 2 parts by weight alkylaryl polyglycol ether

[0730] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and emulsifier and made up to the desired concentration with water. Further test concentrations were prepared by dilution with water. If the addition of ammonium salts and / or penetration enhancers (rapeseed oil methyl ester) was required, these were pipetted in at a concentration of 1000 ppm each after dilution of the finished preparation solution.

[0731] Rice plants (Oryza sativa, var. Balilla) were treated by spraying with the active ingredient preparation at the desired concentration and then inoculated with L3 larvae of the brown-backed rice leafhopper (Nilaparvata lugens).

[0732] After 14 days, the kill rate was determined as a percentage. 100% means that all cicadas were killed, and 0% means that no cicadas were killed.

[0733] In this test, for example, the following compounds from the production examples showed an effect of 100% at an application rate of 20 g / ha: 1-003, 1-005, 1-062.

[0734] In this test, for example, the following compounds from the production examples showed an efficacy of 98% at an application rate of 20 g / ha: 1-002, 1-032, 1-065.

[0735] In this test, for example, the following compounds from the production examples showed an efficacy of 95% at an application rate of 20 g / ha: 1-011, 1-044.

[0736] In this test, for example, the following compounds from the production examples showed an efficacy of 93% at an application rate of 20 g / ha: 1-001, 1-009.

[0737] In this test, for example, the following compounds from the production examples showed an efficacy of 90% at an application rate of 20 g / ha: 1-072, 1-075. In this test, for example, the following compounds from the production examples showed an efficacy of 85% at an application rate of 20 g / ha: 1-043.

[0738] In this test, for example, the following compounds from the production examples showed an effect of 80% at an application rate of 20 g / ha: 1-026.

[0739] Nilaparvata lugens - Test

[0740] Solvent: 14 parts by weight dimethylformamide

[0741] Emulsifier: 2 parts by weight alkylaryl polyglycol ether

[0742] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and emulsifier and made up to the desired concentration with water. Further test concentrations were prepared by dilution with water. If the addition of ammonium salts and / or penetration enhancers (rapeseed oil methyl ester) was required, these were pipetted in at a concentration of 1000 ppm each after dilution of the finished preparation solution.

[0743] Rice plants (Oryza sativa, var. Balilla) were sprayed with the active ingredient preparation at the desired concentration until dripping wet and then inoculated with L3 larvae of the brown-backed rice leafhopper (Nilaparvata lugens).

[0744] After 21 days, the kill rate was determined as a percentage. 100% means that all cicadas were killed, and 0% means that no cicadas were killed.

[0745] In this test, for example, the following compounds from the production examples showed an effect of 100% at an application rate of 20 ppm: 1-093, 1-108, 1-109.

[0746] Nilaparvata lugens - Test

[0747] Solvent: 14 parts by weight dimethyl sulfoxide

[0748] Emulsifier: 2 parts by weight alkylaryl polyglycol ether

[0749] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and emulsifier and made up to the desired concentration with water. Further test concentrations were prepared by dilution with water. If the addition of ammonium salts and / or penetration enhancers (rapeseed oil methyl ester) was required, these were pipetted in at a concentration of 1000 ppm each after dilution of the finished preparation solution. Rice plants (Oryza sativa, var. Bali Ha) were sprayed until dripping wet with the active ingredient formulation at the desired concentration and then inoculated with L3 larvae of the brown-backed rice leafhopper (Nilaparvata lugens).

[0750] After 21 days, the kill rate was determined as a percentage. 100% means that all cicadas were killed, and 0% means that no cicadas were killed.

[0751] In this test, for example, the following compounds from the production examples showed an effect of 100% at an application rate of 20 ppm: 1-112, 1-113, 1-115, 1-118, 1-120, 1-125, 1-126, 1-129, 1-131, 1-133, 1-136.

[0752] In this test, for example, the following compounds from the production examples showed an efficacy of 98% at an application rate of 20 ppm: 1-123, 1-124.

[0753] In this test, for example, the following compounds from the production examples showed an effect of 90% at an application rate of 20 ppm: 1-114.

[0754] In this test, for example, the following compounds from the production examples showed an efficacy of 85% at an application rate of 20 ppm: 1-105, 1-128, 1-130.

[0755] In this test, for example, the following compounds from the production examples showed an effect of 80% at an application rate of 20 ppm: 1-132.

[0756] Euschistus heros - Spray test

[0757] Solvent: 14 parts by weight dimethylformamide

[0758] Emulsifier: 2 parts by weight alkylaryl polyglycol ether

[0759] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and emulsifier and made up to the desired concentration with water. Further test concentrations were prepared by dilution with water. If the addition of ammonium salts and / or penetration enhancers (rapeseed oil methyl ester) was required, these were pipetted in at a concentration of 1000 ppm each after dilution of the finished preparation solution.

[0760] Cotton plants (Gossypium hirsutum), soybean plants (Glycine max), maize plants (Zea mays), or bush bean plants (Phaseolus vulgaris) were treated by spraying with the active ingredient preparation at the desired concentration and then inoculated with 10 larvae of the brown stink bug (Euschistus heros). After 6 days, the plant-protective effect was determined as a percentage. 100% means that no damage was observed; 0% means that the damage to the treated leaves was the same as that to the untreated control.

[0761] In this test, for example, the following compounds from the production examples showed an effect of 90% at an application rate of 100 ppm: 1-001.

[0762] In this test, for example, the following compounds from the production examples showed an efficacy of 98% at an application rate of 20 ppm: 1-065.

[0763] In this test, for example, the following compounds from the production examples showed an efficacy of 95% at an application rate of 20 ppm: 1-060.

[0764] In this test, for example, the following compounds from the production examples showed an efficacy of 93% at an application rate of 20 ppm: 1-043, 1-061.

[0765] In this test, for example, the following compounds from the production examples showed an effect of 90% at an application rate of 20 ppm: 1-047.

[0766] In this test, for example, the following compounds from the production examples showed an efficacy of 85% at an application rate of 20 ppm: 1-032, 1-036, 1-042, 1-044, 1-072, 1-093.

[0767] In this test, for example, the following compounds from the production examples showed an effect of 80% at an application rate of 20 ppm: 1-094.

[0768] Bemisia tabaci test, normal sensitive strain

[0769] Solvent: 14 parts by weight dimethylformamide

[0770] Emulsifier: 2 parts by weight alkylaryl polyglycol ether

[0771] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was dissolved with the specified parts by weight of solvent and emulsifier and made up to the desired concentration with water. Further test concentrations were prepared by dilution with water. If the addition of ammonium salts and / or penetration enhancers (rapeseed oil methyl ester) was required, these were pipetted in at a concentration of 1000 ppm each after dilution of the finished preparation solution.

[0772] Cotton plants (Gossypium hirsutum) infested with eggs, larvae, and puparia of the whitefly (Bemisia tabaci) were treated by spraying with the active ingredient preparation at the desired concentration. After 7 days, the kill rate was determined as a percentage. 100% means that all insects were killed; 0% means that no insects were killed.

[0773] In this test, for example, the following compounds from the production examples showed an effect of 100% at an application rate of 20 g / ha: 1-001, 1-042, 1-047, 1-054, 1-060, 1-062, 1-072, 1-075.

[0774] In this test, for example, the following compounds from the production examples showed an efficacy of 99% at an application rate of 20 g / ha: 1-028, 1-044.

[0775] In this test, for example, the following compounds from the production examples showed an efficacy of 98% at an application rate of 20 g / ha: 1-032, 1-034, 1-061, 1-063.

[0776] In this test, for example, the following compounds from the production examples showed an efficacy of 97% at an application rate of 20 g / ha: 1-050, 1-065, 1-076.

[0777] In this test, for example, the following compounds from the production examples showed an efficacy of 95% at an application rate of 20 g / ha: 1-077.

[0778] In this test, for example, the following compounds from the production examples showed an efficacy of 93% at an application rate of 20 g / ha: 1-043.

[0779] In this test, for example, the following compounds from the production examples showed an effect of 90% at an application rate of 20 g / ha: 1-046, 1-056, 1-080.

[0780] In this test, for example, the following compounds from the production examples showed an effect of 80% at an application rate of 20 g / ha: 1-031, 1-040, 1-088.

[0781] Comparative examples

[0782] Spodoptera frugiperda - Spray test (SPODFR)

[0783] Solvent: 78.0 parts by weight acetone

[0784] 1.5 parts by weight: Dimethylformamide

[0785] Emulsifier: Alkylaryl polyglycol ether

[0786] To prepare a suitable active ingredient formulation, one part by weight of the active ingredient was mixed with the specified amount of solvent and diluted to the desired concentration with water containing an emulsifier concentration of 1000 ppm. Further test concentrations were prepared by dilution with a water-based emulsifier. Leaf sections of maize (Zea mays) were sprayed with a preparation of the active ingredient at the desired concentration. After drying, the leaf sections were infested by fall armyworm larvae (Spodoptera frugiperda).

[0787] After the specified period, the mortality rate was determined as a percentage. 100% means that all caterpillars were killed, and 0% means that none of the caterpillars were killed.

[0788] In this test, for example, the following compound from the preparation examples showed superior activity compared to the previous state of the art: see list

[0789] Bemisia tabaci - spray test, normal susceptible strain (BEMITA)

[0790] Solvent: 14 parts by weight dimethylformamide

[0791] Emulsifier: 2 parts by weight alkylaryl polyglycol ether

[0792] To prepare a suitable active ingredient formulation, one part by weight of the active ingredient was mixed with the specified amount of solvent and diluted with water to the desired concentration. Further test concentrations were prepared by dilution with water. Ammonium salt and penetration enhancer (rapeseed oil methyl ester) at a dosage of 1000 ppm were added at the desired concentration.

[0793] Cotton plants (Gossypium hirsutum) infested with eggs, larvae and pupae of the whitefly (Bemisia tabaci) were treated by spraying them with the active ingredient at the desired concentration.

[0794] After the specified period, the mortality rate was determined as a percentage. 100% means that all whiteflies were killed, and 0% means that none of the whiteflies were killed.

[0795] In this test, for example, the following compounds from the preparation examples showed superior activity compared to the state of the art: see list

[0796] Nilaparvata lugens - test (NILALU)

[0797] Solvent: 14 parts by weight dimethylformamide

[0798] Emulsifier: 2 parts by weight alkylaryl polyglycol ether

[0799] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was mixed with the specified amount of solvent and diluted with water to the desired concentration. Further test concentrations were prepared by dilution with water. Ammonium salt and penetration enhancer (rapeseed oil methyl ester) at a dosage of 1000 ppm were added at the desired concentration. Rice plants (Oryza sativa, var. Bali Ha) treated by spraying with the active ingredient preparation at the desired concentration and were subsequently infested with L3 larvae of the brown leafhopper (Nilaparvata lugens).

[0800] After the specified period, the feeding control was determined as a percentage. 100% means that no feeding damage is visible, and 0% means that the plant damage is the same as that of the untreated control plants.

[0801] In this test, for example, the following compounds from the preparation examples showed superior activity compared to the state of the art: see list

[0802] Nezara viridula - spray test (NEZAVI)

[0803] Solvent: 14 parts by weight dimethylformamide

[0804] Emulsifier: 2 parts by weight alkylaryl polyglycol ether

[0805] To prepare a suitable active ingredient formulation, one part by weight of the active ingredient was mixed with the specified amount of solvent and diluted with water to the desired concentration. Further test concentrations were prepared by dilution with water. Ammonium salt and penetration enhancer (rapeseed oil methyl ester) at a dosage of 1000 ppm were added at the desired concentration.

[0806] Cotton plants (Gossypium hirsutum) or soy plants (Glycine max) were treated by spraying them with the active ingredient preparation at the desired concentration and infesting them with 10 larvae per plant of the green plant bug (Nezara viridula).

[0807] After the specified period, the feeding control was determined as a percentage. 100% means that no feeding damage is visible, and 0% means that the plant damage is the same as that of the untreated control plants.

[0808] In this test, for example, the following compounds from the preparation examples showed superior activity compared to the state of the art: see list

[0809] Frankliniella occidentalis - Spray test (FRANOC)

[0810] Solvent: 14 parts by weight dimethylformamide

[0811] Emulsifier: 2 parts by weight alkylaryl polyglycol ether

[0812] To prepare a suitable active ingredient formulation, 1 part by weight of the active ingredient was mixed with the specified amount of solvent and emulsifier and diluted with water to the desired concentration. Further test concentrations were prepared by dilution with water. Ammonium salt and penetration enhancer at a dosage of 1000 ppm were added at the desired concentration.

[0813] Cotton plants (Gossypium hirsutum) were treated by spraying them with the active ingredient preparation at the desired concentration. After drying, the plants were infested by western flower thrips (Frankliniella occidentalis).

[0814] After the specified period, the plant protection effect was determined as a percentage. 100% means that no feeding damage was present, and 0% means that the plant damage is the same as in the untreated control plot.

[0815] In this test, for example, the following compounds from the preparation examples showed superior activity compared to the state of the art: see list

[0816]

[0817]

[0818]

[0819]

[0820] *date = days after treatment

Claims

Patent claims 1. Combination of formula (I) wherein A for a 5- to 10-membered aromatic or heteroaromatic ring or a bicyclic ring system, each unsubstituted or substituted with 1 to 3 R A , stands; each one stands R A independently for halogen, cyano, nitro, SF5, C(O)R a , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a , OC(O)R a , OSO2R a , or SO2NR b R c ; or for Ci-C6-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C-cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f may be substituted; or for phenyl or a 5- or 6-membered heteroaromatic ring, each unsubstituted or substituted with 1 to 3 R f; or two adjacent R A together they form an unsubstituted or simple to 4-fold with halogen and / or possibly with R f substituted linear C3-C5 alkylene group, wherein independently 1 CH2 unit can be replaced by carbonyl and / or 1 to 2 CH2 units can be replaced by O or S; X and Y can independently represent O or S; R 1 H stands for; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C-cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f may be substituted; or for C(T)R a , C(O)OR a , C(T)NR b R c , OH, OR a , S(O) n R a or SO2NR b R c stands; R 2represents phenyl, naphthyl, or a 5- to 10-membered heteroaromatic ring, each either unsubstituted or substituted with 1 to 3 Rs 21 ; each one R 21 independently for halogen, cyano, nitro, SF5, C(T)R a , C(N=OR b )R c , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a OC(O)R a , OSO2R a , or SO2NR b R c ; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Ci-C-cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f can be substituted; or two adjacent R 21 together they form an unsubstituted or simple to 4-fold halogen and / or possibly with 1 to 2 r fsubstituted linear Ci-Cs-alkylcn groups, wherein independently one CH2 unit can be replaced by carbonyl and / or one to two CH2 units can be replaced by O or S; R 3 stands for H; or for halogen, cyano, OH, OR. a or so) n R a stands for; or stands for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Ci-C-cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f They may be substituted; R 4 and R 5 each independently stand for H; or for Ci-Ce-Alky 1, C2-Ce-Alkeny 1, C2-Ce-Alkynyl or Ci-C-Cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with 1 to 3 R f may be substituted; or R 4 and R 5together they form a C2-Ce alkyl chain and a 3- or 6-membered ring, which may optionally be combined with R f may be substituted and / or by O, S(O) n or NR d may be interrupted, or R 3 and R 5 together they form a C3-C4 alkyl chain and a 5- or 6-membered ring, which may optionally be combined with R f may be substituted and / or by O, S(O) n or NR d may be interrupted; R 6 stands for H; or for C(T)R a , C(O)OR a , C(T)NR b R c , OH, OR a or so) n R a stands for; or stands for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl or Ci-C-cycloalkyl, all of which may be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f They may be substituted; R 7H stands for; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl or Ci-C-cycloalkyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R f may be substituted; or for C(O)R a , C(O)OR a , C(O)NR b R c , NR d R e , OR a , S(O) n R a or SO2NR b R c stands; or stands for phenyl or for a 4- to 7-membered saturated, partially saturated or aromatic heterocycle with 1 to 3 heteroatoms, each unsubstituted or substituted with 3 R f ; or represents a C2-C3 alkyl chain that has a link to The point of contact is the neighboring carbon atom connected to A, and which may be connected to R. f may be substituted and / or by O, S(O) n or NR d may be interrupted; R 8H stands for; or for Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl or C5-C7- Cycloalkenyl stands for all of which can be unsubstituted, or simply up to 7-fold with halogen and / or possibly with R. g may be substituted; or for C(O)R a , C(O)OR a , C(O)NR b R c , S(O) n R a or SO2NR b R c stands; or stands for a 4- to 7-membered saturated or partially saturated heterocycle with 1 to 3 heteroatoms, each unsubstituted or simply to 5-fold with halogen and / or with R f may be substituted; or R 7 and R 8are linked together and form a 5- to 7-membered partially saturated heterocyclic ring with 2 to 3 heteroatoms, which may be unsubstituted or optionally substituted with C1-C4 alkyl, Cs-Ce cycloalkyl or Cs-Ce spirocycloalkyl, each of which may be unsubstituted or singly to triply substituted with halogen and / or optionally with R f can be substituted; each one is involved T independently of each other for O or S; R a independently of each other for Ci-Ce-alkyl, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with 1 to 3 R f They may be substituted; R b and R cindependently for H; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f ; or R b and R c together they form a ring with 3 to 7 segments; R d and R e independently for H; or for C(T)R a , C(O)OR a or so) n R a ; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f ; or R d and R e together they form a ring with 3 to 7 segments; R findependently for halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Cs-Ce-cycloalkyl. Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-Czi-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, Ci- C4-Alky Icarbony 1, Ci -Czi-Alkoxy carbony 1; R g independently for halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-Czi-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, Ci-C4-alkylcarbonyl, Ci-C4-alkoxy carbonyl, C1-C4-alkylcarbonylamino or C1-C4- Alkylaminocarbonyl; or for a 4- to 7-membered saturated, partially saturated or aromatic heterocycle with 1 to 3 heteroatoms, each unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f; n independently for 0, 1 or 2.

2. Compounds according to claim 1, wherein A for phenyl or for a heteroaromatic from the series furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, all unsubstituted or substituted with 1 to 3 R A , stands; each one stands R A independently for halogen, cyano, nitro, SF5, C(O)R a , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a , OC(O)R a , OSO2R a , or SO2NR b R c; or for Ci-C6 alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C cycloalkyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted; X and Y stand for O; R 1 H stands for; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C-cycloalkyl, all of which can be unsubstituted, or simply up to 7-fold with halogen and / or optionally with R f may be substituted; or for C(T)R a , C(O)OR a or S(O)2R a stands; R 2for phenyl or for a heteroaromatic from the series furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, all unsubstituted or substituted or substituted with 1 to 3 R 21 ; each one R 21 independently for halogen, cyano, nitro, SF5, C(T)R a , C(N=OR b )R c , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a OC(O)R a , OSO2R a , or SO2NR b R c ; or for Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl or Cs-C cycloalkyl, all of which are respective They may be unsubstituted, or simply up to 5 times the amount of halogen and / or possibly with R. f They may be substituted; R 3 H stands for; or for halogen, cyano or OH stands for; or for Ci-C4-alkyl or C2-C4-alkenyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted; R 4 and R 5 each independently represent H; or represent C1-C4 alkyl groups, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R. f may be substituted; or R 4 and R 5 together they form a C2-C6 alkyl chain and a 3- or 6-membered ring, which may optionally be combined with R f may be substituted and / or by O, S(O) n or NR d may be interrupted, 5-fold; or R 3 and R5 are jointly linked to form a C3-C4 alkyl chain and a 5- or 6-membered ring, which may optionally be combined with R f may be substituted and / or by O, S(O) n or NR d may be interrupted; R 6 stands for H; or for C(T)R a , C(O)OR a or so) n R a stands; or stands for C1-C4 alkyl or C2-C6 alkenyl, each of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted; R 7 H stands for; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkyny 1 or Cs-Cs-cycloalkyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R f may be substituted; or for C(O)R a , C(O)OR a , C(O)NR b R c , NR d R e , OR a or so) nR a stands; or stands for a C2-C3 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point and which may be linked to R f may be substituted; R 8 H stands for; or for Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl or C5-C7- Cycloalkenyl stands for all of which can be unsubstituted, or simply up to five times with halogen and / or possibly with R. g may be substituted; or for C(O)R a , C(O)OR a , or so) n R a stands; or stands for a heterocycle from the series oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiethanyl-l-oxide, thiethanyl-l,l-dioxide, thiolanyl, thiany 1, or thianyl-l-oxide, all unsubstituted or substituted with R f ; or R 7 and R 8are linked together and form a 5- to 7-membered partially saturated heterocyclic ring with 2 to 3 heteroatoms, which may be unsubstituted or optionally substituted with C1-C4 alkyl, each unsubstituted or singly to triplely with halogen and / or optionally with R f substituted; each one stands for T independently of each other for O or S; R a independently of each other for Ci-Ce-alkyl, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted; R b and R c independently of each other for H; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f ; or R b and R ctogether they form a ring with 3 to 6 segments; R d and R e independently for H; or for C(T)R a , C(O)OR a ; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with R f ; or R d and R e together they form a ring with 3 to 5 segments; R f independently for halogen, cyano, nitro, hydroxy; or for Ci-C4-alkyl, C;,-CT-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, Ci-Czi-haloalkylsulfmyl, Ci-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, Ci-C4 alkylcarbonyl or Ci-C4 alkoxy carbonyl; R gunabhängig voneinander für Halogen, Cyano, Nitro, Hydroxy, Ci-C4-Alkyl, Cs-Ce-Cycloalkyl, Ci-C4-Haloalkyl, Ci-C4-Alkoxy, Ci-C4-Haloalkoxy, Ci-C4-Alkylthio, Ci-C4-Haloalkylthio, Ci- C4- Alkylsulfinyl, Ci-Czi-Haloalkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Haloalkylsulfonyl, Ci- C4-Alkylcarbonyl, Ci-C4-Alkoxy carbonyl, C1-C4- Alkylcarbonylamino oder C1-C4- Alkylaminocarbonyl; or for phenyl or for a heterocycle from the series furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, oxetanyl, oxolanyl, Dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl or morpholinyl, each unsubstituted or substituted with 1 to 3 halogens and / or optionally with R f ; n independently for 0, 1 or 2.

3. Compounds according to one of claims 1 to 2, wherein A for phenyl or for a heteroaromatic from the series furanyl, thienyl, pyrazolyl, thiazolyl, pyridyl, pyrimidyl, pyridazinyl or pyrazinyl, all unsubstituted or substituted with 1 to 3 R A , stands; each one stands R A independently for halogen, cyano, C(O)R a , C(O)OR a , C(O)NR b R c , OR a , S(O) n R a , OSO2R a , or SO2NR b R c ; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or Cs-Ce-cycloalkyl, each of which may be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted; X and Y stand for O; R 1 H stands for; or for Ci-C4-alkyl, C2-C4-alkenyl or C2-C4-alkynyl, all of which can be unsubstituted, or simply to 3-fold with halogen and / or optionally with R. fmay be substituted; or for C(O)R a , C(O)OR a or S(O)2R a stands; R 2 for phenyl or for a heteroaromatic from the series thienyl, pyrazolyl, oxazolyl, thiazolyl, pyridyl, pyrimidyl, pyridazinyl or pyrazinyl, all unsubstituted or substituted or substituted with 1 to 3 R 21 ; each one R 21 independently for halogen, cyano, nitro, C(O)R a , C(N=OR b )R c , C(O)OR a , C(T)NR b R c , NR d R e , OR a , S(O) n R a OC(O)R a or SO2NR b R c ; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C4-cycloalkyl, each of which may be unsubstituted, or simply up to 5-fold with halogen and / or optionally with R f They may be substituted; R 3 stands for H or for Ci-C4-alkyl; R 4 and R 5 each independently stand for H or for Ci-C4 alkyl; or R 3 and R 5 together they form a C3-C1 alkyl chain and create a 5- or 6-membered ring; R 6 stands for H; or for C(O)R a , C(O)OR a or so) n R a stands for; or stands for C1-C4 alkyl; R 7 H stands for; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkyny 1 or Cs-Cs-cycloalkyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R f may be substituted; or for C(O)R a , C(O)OR a , C(O)NR b R c , NR d R e , OR a or so) n R a stands; or stands for a C2-C3 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point; R8 H stands for; or for Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C5-C7-cycloalkenyl, all of which can be unsubstituted, or simply to fivefold with halogen and / or optionally with R. g may be substituted; or for C(O)R a , C(O)OR a , or so) n R a stands for; or stands for a heterocycle from the series oxetanyl, oxolanyl, oxanyl, thietanyl, thietanyl-1-oxide, thietanyl-1,1-dioxide, thianyl, thianyl-1-oxide or thiany-1-1,1-dioxide; or R 7 and R 8 are connected to each other and form a 5- to 6-membered partially saturated heterocyclic ring; each T independently of each other for O or S; R a independently of each other for C1-C4 alkyl, Cs-Ce-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, all of which can be unsubstituted, or simply up to 5-fold with halogen and / or optionally with Rf They may be substituted; R b and R c independently for H; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with 1 to 2 Rs f ; or R b and R c together they form a ring with 3 to 6 segments; R d and R e independently for H; or for C(T)R a , C(O)OR a ; or for Ci-Ce-alkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C2-Ce-alkenyl, C2-C6-alkynyl, all unsubstituted or substituted with 1 to 5 halogens and / or optionally with 1 to 2 R f ; or R d and R e together they form a ring with 3 to 5 segments; R funabhängig voneinander für Halogen, Cyano, Nitro, Hydroxy, Ci-C4-Alkyl, Cs-Ce-Cycloalkyl. Ci-C4-Haloalkyl, Ci-C4-Alkoxy, Ci-C4-Haloalkoxy, Ci-C4-Alkylthio, Ci-C4-Haloalkylthio, Ci- C4- Alkylsulfinyl, Ci-C4-Haloalkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Haloalkylsulfonyl, Ci- C4-Alkylcarbonyl oder Ci-C4-Alkoxy carbonyl; R g unabhängig voneinander für Halogen, Cyano, Nitro, Hydroxy, Ci-C4-Alkyl, Cs-Ce-Cycloalkyl, Ci-C4-Haloalkyl, Ci-C4-Alkoxy, Ci-C4-Haloalkoxy, Ci-C4-Alkylthio, Ci-C4-Haloalkylthio, Ci- C4-Alkylsulfmyl, Ci-C4-Haloalkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Haloalkylsulfonyl, Ci- C4-Alkylcarbonyl, Ci-C4-Alkoxy carbonyl, C1-C4- Alkylcarbonylamino oder C1-C4- Alkylaminocarbonyl; oder für einen Heterocyclus aus der Reihe Oxetanyl, Oxolanyl, Dioxolanyl, Oxanyl, Dioxanyl, Thiethanyl, Thiolanyl, Thianyl oder Morpholinyl alle jeweils unsubstituiert oder substituiert mit 1 bis 3 Halogen und / oder gegebenenfalls mit R f; n independently for 0, 1 or 2.

4. Compounds according to any one of claims 1 to 3, wherein A for phenyl or for a heteroaromatic from the series thienyl, pyrazolyl, thiazolyl, pyridyl, pyrimidyl, pyridazinyl or pyrazinyl, all unsubstituted or substituted with 1 to 3 R A , stands; each one stands R A independently for halogen, cyano, OR a ; or for Ci-C4-alkyl, each unsubstituted or simply to 3-fold substituted with halogen; X and Y stand for O; R 1 stands for H; or for Ci-C4-alkyl; or for C(O)R a , C(O)OR a or S(O)2R a stands; R 2 for phenyl thienyl, pyrazolyl, thiazolyl or pyridyl, all unsubstituted or substituted or substituted with 1 to 3 R 21 ; each one R 21 independently for halogen, cyano, nitro, ORa , S(O) n R a or SO2NR b R c ; or for Ci-C4-alkyl, either unsubstituted or simply to 5-fold substituted with fluorine or chlorine; or for cyclopropyl, unsubstituted or simply to 3-fold substituted with fluorine or chlorine or substituted with cyano; R 3 H stands for; R 4 and R 5 each stand independently for H; R 6 stands for H; or for C(O)R a or C(O)OR a stands for; or stands for methyl or ethyl; R 7 H stands for; or for Ci-C4-alkyl or C,-Cs-cycloalkyl stands for; or for C(O)R a , C(O)OR a , C(O)NR b R c , NR d R e , OR a or so) n R a stands; or stands for a C2-C3 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point; R 8H stands for; or for Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C5-C7-cycloalkenyl, all of which can be unsubstituted, or simply to fivefold with fluorine or chlorine and / or optionally with R g may be substituted; or for C(O)R a , C(O)OR a , or so) n R a stands for; or stands for a heterocycle from the series oxolanyl, oxanyl, thietanyl, thietanyl-1-oxide, thietanyl-1,1-dioxide, thianyl, thianyl-1-oxide or thiany-1-1,1-dioxide; or or R 8 stands together with R 7 for one of the leftovers where * represents the connection point to O and # represents the connection point to C; where each R a independently of each other for Ci-C4-alkyl or C;,-C,-Cvcloalkvl, each unsubstituted or 1-fold to 5-fold substituted with fluorine or chlorine; R b and R cindependently for H; or for Ci-C4-alkyl, or Cs-Ce-cycloalkyl; R d and R e independently for H; or for Ci-C4-alkyl or Cs-Ce-cycloalkyl; R g independently for halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Cs-Ce-cycloalkyl. Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-Czi-haloalkylsulfmyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, Ci- C4-alkylcarbonyl, Ci-C4-alkoxy carbonyl, C1-C4-alkylcarbonylamino or C1-C4- Alkylaminocarbonyl; or for a heterocycle from the series oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl or morpholinyl; n independently for 0, 1 or 2.

5. Compounds according to any one of claims 1 to 4, wherein A for phenyl, pyridyl, pyrimidyl, pyrazinyl or thiazolyl, each unsubstituted or substituted with 1 to 3 R A, stands; each one stands R A independently for fluorine, chlorine, bromine, cyano, methyl or methoxy; X and Y stand for O; R 1 stands for H; or for methyl or ethyl; or for C(O)R a or C(O)OR a stands; R 2 For phenyl, thienyl or pyridyl, unsubstituted or substituted with 1 to 2 Rs is used. 21 ; each one R 21 independently for fluorine, chlorine, bromine, cyano, methyl, methoxy, CF3, CHF2, OCF3, OCHF2, SCF3, S(O)CF3, SO2CF3, cyclopropyl, 1-cyanocyclopropyl, 4-fluorophenyl, 6-fluoropyrid-3-yl; R 3 H stands for; R 4 and R 5 stand for H; R 6 H stands for; R 7H stands for; or stands for methyl, ethyl, n-propyl, i-propyl or c-propyl, C(O)NHCH3, OCH3, C(O)CH3, C(O)OCH3 or NH2; or stands for a C2 alkyl chain that is linked to A via a carbon atom adjacent to the attachment point; R 8 H stands for; or for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, propenyl or propynyl, all of which can be unsubstituted, or optionally with R. g may be substituted; or for C(O)R a , C(O)OR a , or S(O)2R a stands for; or stands for oxanyl, thietanyl-1,1-dioxide or thiany-1-1,1-dioxide; or R 8 stands together with R 7 for one of the leftovers where * represents the connection point to O and # represents the connection point to C; where each R sindependently of each other for methyl, ethyl, n-propyl, i-propyl, c-propyl or c-butyl, each unsubstituted or substituted with 1-5 fluorine; R g independently of each other for Methyl, Ethyl, Methoxy, Ethoxy, c-Propyl, c-Butyl, Cyano, C(O)NHCH3, C(O)CH3, C(O)-c-Butyl, C(O)-c-Propyl, C(O)CH2-c-Pr, C(O)-i-Pr, C(O)OCH3, C(O)OCH2CH3, SO2CH3; or for one of the heterocycles Oxolanyl or Oxanyl.

6. Compounds according to any one of claims 1 to 5, wherein A represents one of the following residues Q1 to Q7. each unsubstituted or substituted with 1 to 2 R A , where * represents the connection point to N and # represents the connection point to C, and where each R A independently stands for fluorine, chlorine, cyano or methoxy; X and Y stand for O; R 1H stands for; or for Methyl, C(O)CH3, C(O)CH2CH3, C(O)OCH3, C(O)OCH2CH3, C(O)On-Propyl, C(O)Oc-Pr, C(O)c-Propyl or C(O)Oi-Propyl; R 2 one of the remnants of Ul-U-3 stands U-1 U-2 U-3 each substituted with 1 to 3 R 21 ; where # represents the connection point to C; and where each R 21 independently of each other for fluorine, chlorine, bromine, cyano, CF3, CHF2, OCF3, OCHF2, SCF3, SO2CF3; R 3 H stands for; R 4 and R 5 stand for H; R 6 H stands for; R 7 for H; or for methyl, ethyl, n-propyl, i-propyl or c-propyl, C(O)NHCH3, OCH3, C(O)CH3, C(O)OCH3 or NH2; or for CH2CH2, which is bonded to Ql via a carbon atom adjacent to the point of attachment; R 8H stands for; or for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, CH2-c-propyl, propynyl, CH2C(O)NHCH3, C(O)CH3, C(O)CH2CH3, C(O)-c-butyl, C(O)-c-propyl, C(O)CH2-c-propyl, C(O)-i-propyl, C(O)OCH2CH3, CH2CN, CH2CH2CN, CH2CH2CH2CN, SO2CH3, CH2CH2SO2CH3, CH2CH=CH2, CH2CH2OCH3, CH2CCH, CH(CH3)-c-propyl or CH(CH3)C(O)OCH3; or R 8 represents one of the remains where * represents the point of connection to O or R 8 stands together with R 7 for one of the leftovers Here, * represents the connection point to O and # represents the connection point to C.

7. Formulation, in particular an agrochemical formulation, comprising at least one compound of formula (I) according to any one of claims 1 to 6.

8. Formulation according to claim 7, further comprising at least one extender and / or at least one surfactant.

9. Formulation according to claim 7 or 8, characterized in that the compound of formula (I) is present in a mixture with at least one further active ingredient.

10. Method for controlling pests, characterized in that a compound of formula (I) according to one of claims 1 to 7 or a formulation according to one of claims 7 to 9 is applied to the pests and / or their habitat.

11. Method according to claim 10, characterized in that the pest is an animal pest.

12. Method according to claim 10 or 11, characterized in that the pest is an insect or an arachnid or a nematode.

13. Use of a compound of formula (I) according to any one of claims 1 to 6 or a formulation according to any one of claims 7 to 9 for controlling animal pests.

14. Use according to claim 13, characterized in that the animal pest is an insect, an arachnid or a nematode.

15. Use according to claim 13 or 14 in plant protection.

16. Method for protecting a seed or a germinating plant from pests, in particular animal pests, comprising a method step in which the seed is brought into contact with a compound of formula (I) according to any one of claims 1 to 6 or with a formulation according to any one of claims 7 to 9.

17. Seed obtained by a process according to claim 16.

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