Stabilization of suspension concentrates with ethoxylated ricinolein.
Ethoxylated ricinolein stabilizes aqueous pesticide compositions with high water solubility active ingredients, addressing stability issues by preventing particle growth and aggregation, ensuring stable and safe application.
Patent Information
- Application Number
- JP2021564960
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2019-05-03
- Filing Date
- 2020-04-20
- Publication Date
- 2025-09-30
- Estimated Expiration
- 2040-04-20
AI Technical Summary
Aqueous suspension concentrates face stability issues with active ingredients having high water solubility, leading to particle growth, aggregation, and gelling, which affect rheological properties and nozzle clogging.
An aqueous pesticide composition using ethoxylated ricinolein in polymerized form with 35 to 50 ethylene oxide molecules per ricinolein molecule stabilizes suspended particles of active ingredients with high water solubility, preventing particle growth and aggregation.
The composition maintains stability and prevents settling, ensuring effective application without viscosity increase or nozzle clogging, while maintaining low organic solvent content and safe handling.
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Figure 0007746163000001 
Figure 0007746163000002 
Figure 0007746163000003
Abstract
Description
[Technical Field]
[0001] The present invention relates to an aqueous pesticide composition comprising suspended particles of an active ingredient having a water solubility of at least 1 g / L at 25° C. and an ethoxylated ricinolein in polymerized form containing 35 to 50 ethylene oxide molecules per ricinolein molecule. The present invention also relates to a method for preparing the pesticide composition; a method for controlling attack by phytopathogenic fungi and / or unwanted plant growth and / or unwanted insects or mites and / or a method for controlling plant growth, wherein the pesticide composition is capable of acting on the respective pests, their environment, or crops, soil, and / or unwanted plants and / or crops and / or their environment to be protected from the respective pests. The present invention also relates to non-therapeutic methods which comprise administering or applying to an animal, orally, topically or parenterally, a parasiticidally effective amount of a pesticide composition to treat an animal infested or infected with a parasite, or to prevent the animal from becoming infected or infested by a parasite, or to protect the animal from infestation or infection by a parasite; methods of treating, controlling, preventing or protecting an animal against infestation or infection by a parasite by administering or applying to the animal orally, topically or parenterally the pesticide composition; the use of a pesticide composition to protect growing plants or plant propagation material from attack or infestation by invertebrate pests; the use of a pesticide composition to combat parasites or insects in and on animals; and pesticide compositions for use in methods of controlling or preventing infestation by parasites of insects or animals. Other objects are the use of ethoxylated ricinolein for stabilizing an aqueous pesticide composition containing suspended particles of an active ingredient, and a method for stabilizing an aqueous pesticide composition containing suspended particles of an active ingredient, comprising the step of contacting ethoxylated ricinolein with particles of the active ingredient and water. Combinations of embodiments and other embodiments are within the scope of the present invention, regardless of their respective priority levels. [Background technology]
[0002] Aqueous suspension concentrates are one of the most commonly used formulation types in the agrochemical industry.They are usually limited to active ingredients with very low water solubility.Active ingredients with high water solubility are difficult to incorporate into aqueous suspension concentrates, because the particles either dissolve or undergo Ostwald ripening during storage, which leads to an increase in particle size and ultimately sedimentation.Another stability problem of such formulations is gelation, that is, the formation of unstructured aggregates of the active ingredient, which adversely affects the desired rheological profile, for example, by increasing viscosity or clogging spray nozzles.
[0003] Aqueous suspension concentrates, on the other hand, have the advantage of low organic solvent content and relatively safe handling and application for applicants. Summary of the Invention [Problem to be solved by the invention]
[0004] It was therefore desirable to provide an aqueous pesticide composition containing an active ingredient with high water solubility in the form of suspended particles that is stable on storage, does not undergo particle growth, particle aggregation or agglomeration and therefore does not tend to cause particle gelling or settling. [Means for solving the problem]
[0005] The purpose is to a) suspended particles of the active ingredient; and b) ethoxylated ricinolein; wherein the active ingredient has a water solubility of at least 1 g / L at 25°C; and the ethoxylated ricinolein contains, in polymerized form, 35 to 50 ethylene oxide molecules per molecule of ricinolein. DETAILED DESCRIPTION OF THE INVENTION
[0006] Surprisingly, it has been found that the degree of ethoxylation of the ricinolein is crucial to producing the advantageous compositions of the present invention.
[0007] The pesticide composition is an aqueous pesticide composition. The water content of the pesticide composition is typically at least 1 wt%, preferably at least 5 wt%, more preferably at least 10 wt%, more preferably at least 15 wt%, most preferably at least 20 wt%, most preferably at least 25 wt%, particularly preferably at least 30 wt%, and particularly preferably at least 35 wt%, based on the total weight of the pesticide composition each time.
[0008] The water content of the pesticide composition is typically up to 95 wt%, preferably up to 90 wt%, more preferably up to 80 wt%, most preferably up to 70 wt%, particularly preferably up to 60 wt%, and especially up to 50 wt%, based on the total weight of the pesticide composition. The water content of the pesticide composition is typically 10 to 85 wt%, preferably 10 to 65 wt%, and more preferably 15 to 60 wt%, based on the total weight of the pesticide composition.
[0009] The pesticide composition comprises ethoxylated ricinolein, which is the major component of castor oil and is synonymously referred to as glyceryl triricinoleate (CAS number 2540-54-7).
[0010] Ethoxylated ricinolein can be prepared by reacting ethylene oxide with ricinolein, optionally in the presence of a catalyst such as NaOH, at elevated temperatures, such as 100-200° C. Ethoxylated ricinolein is commercially available under the trade names Agnique CSO-40, Agnique CSO-25, Agnique CSO-35, or Agnique CSO-54.
[0011] Ethoxylated ricinolein contains 35 to 50 ethylene oxide molecules per ricinolein molecule in polymerized form. In other words, ethoxylated ricinolein is obtained by the reaction of 35 to 50 moles of ethylene oxide per mole of ricinolein. Preferably, ethoxylated ricinolein contains 37 to 50 ethylene oxide molecules per ricinolein molecule in polymerized form, preferably 37 to 45 ethylene oxide molecules per ricinolein molecule. Ethoxylated ricinolein may contain at least 38 ethylene oxide molecules per ricinolein molecule in polymerized form, preferably at least 39 ethylene oxide molecules. Ethoxylated ricinolein may contain up to 48 ethylene oxide molecules per ricinolein molecule in polymerized form, preferably up to 46, more preferably up to 44, and most preferably up to 42 ethylene oxide molecules per ricinolein molecule in polymerized form. The ethoxylated ricinolein may contain 38 to 50 ethylene oxide molecules per molecule of ricinolein in polymerized form, preferably 38 to 45, and more preferably 38 to 42 ethylene oxide molecules per molecule of ricinolein in polymerized form.
[0012] The concentration of the ethoxylated ricinolein may be at least 0.5 wt%, preferably at least 1 wt%, more preferably at least 2 wt%, most preferably at least 3 wt%, and particularly at least 4 wt%, based on the total weight of the pesticide composition. The concentration of the ethoxylated ricinolein may be up to 30 wt%, preferably up to 25 wt%, more preferably up to 20 wt%, and most preferably up to 15 wt%, based on the total weight of the pesticide composition. The concentration of the ethoxylated ricinolein is typically 1 to 25 wt%, preferably 2 to 20 wt%, and more preferably 3 to 15 wt%, based on the total weight of the pesticide composition.
[0013] The weight ratio of active ingredient to ethoxylated ricinolein is typically 1:1 to 100:1, preferably 2:1 to 20:1. The weight ratio of active ingredient to ethoxylated ricinolein is typically up to 30:1, preferably up to 25:1.
[0014] The pesticide composition contains an active ingredient. The active ingredient may be selected from the group consisting of fungicides, insecticides, nematicides, herbicides, safeners, micronutrients, biopesticides, nitrification inhibitors, urease inhibitors, and / or growth regulators. In one embodiment, the pesticide is an insecticide. In another embodiment, the pesticide is a fungicide. In yet another embodiment, the pesticide is a herbicide. The skilled person is familiar with pesticides, such as those that can be found in, for example, Pesticide Manual, 16th Edition (2013), The British Crop Protection Council, London. Suitable insecticides are insecticides from the classes of carbamates, organophosphates, organochlorines, phenylpyrazoles, pyrethroids, neonicotinoids, spinosyns, avermectins, milbemycins, juvenile hormone analogues, alkyl halides, organotin compounds, nereistoxin analogues, benzoylureas, diacylhydrazines, METI acarizides, and insecticides such as chloropicrin, pymetrozine, flonicamid, clofentezine, hexythiazox, etoxazole, diafenthiuron, propargite, tetradifon, chlorfenapyr, DNOC, buprofezin, cyromazine, amitraz, hydramethylnon, acequinocyl, fluacrypyrim, rotenone, or derivatives thereof.Suitable disinfectants include dinitroaniline, allylamine, anilinopyrimidine, antibiotics, aromatic hydrocarbons, benzenesulfonamides, benzimidazole, benzisothiazole, benzophenone, benzothiadiazole, benzotriazine, benzyl carbamate, carbamate, carboxamide, carboxylic acid diamide, chloronitrile cyanoacetamide oxime, cyanoimidazole, cyclopropanecarboxamide, dicarboximide, dihydrodioxazine, dinitrophenyl crotonate, dithiocarbamate, dithiolane, ethyl phosphonate, ethylaminothiazolecarboxamide, guanidine, hydroxy-(2-amino)pyrimidine, hydroxyanilide, imidazole, imidazolinone, inorganic substances, isobenzofuranone, methoxyacrylate, methoxy Fungicides from the classes of carbamates, morpholines, N-phenylcarbamates, oxazolidinediones, oximinoacetates, oximinoacetamides, peptidylpyrimidine nucleosides, phenylacetamides, phenylamides, phenylpyrroles, phenylureas, phosphonates, phosphorothiolates, phthalamic acids, phthalimides, piperazines, piperidines, propionamides, pyridazinones, pyridines, pyridinylmethylbenzamides, pyrimidinamines, pyrimidines, pyrimidinone hydrazones, pyrroloquinolinones, quinazolinones, quinolines, quinones, sulfamides, sulfamoyltriazoles, thiazolecarboxamides, thiocarbamates, thiophanates, thiophenecarboxamides, toluamides, triphenyltin compounds, triazines, triazoles.Suitable herbicides include acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofurans, benzoic acid, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanedione, dinitroaniline, dinitrophenol, diphenyl ether, glycine, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinedione, oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines. Herbicides from the classes of phosphorus, phenylpyridazines, phosphinic acids, phosphoramidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidinyl (thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracil, and urea.
[0015] Suitable plant growth regulators are antiauxins, auxins, cytokinins, defoliants, ethylene regulators, ethylene releasing agents, gibberellins, growth inhibitors, morphactins, growth retardants, growth stimulants, and further unclassified plant growth regulators.
[0016] Suitable micronutrients are compounds containing boron, zinc, iron, copper, manganese, chlorine, and molybdenum.
[0017] The pesticide composition contains a pesticidal amount of the active ingredient. The term "effective amount" refers to an amount of the active ingredient that is sufficient to control harmful fungi on cultivated plants or protect materials, without causing substantial damage to the treated plants. Such an amount can vary widely and depends on various factors, such as the pest species to be controlled, the cultivated plants or materials to be treated, climatic conditions, and the specific active ingredient used.
[0018] The concentration of the active ingredient in the pesticide composition is typically at least 5 wt%, more preferably at least 10 wt%, most preferably at least 15 wt%, particularly preferably at least 20 wt%, most preferably at least 25 wt%, and particularly preferably at least 30 wt%, based on the total weight of the pesticide composition. The concentration of the active ingredient in the pesticide composition is typically up to 95 wt%, preferably up to 85 wt%, more preferably up to 75 wt%, particularly preferably up to 75 wt%, and particularly preferably up to 65 wt%, based on the total weight of the pesticide composition. The pesticide composition typically contains the active ingredient in a concentration of 10 to 90 wt%, preferably 15 to 60 wt%, and more preferably 20 to 50 wt%, based on the total weight of the pesticide composition.
[0019] The active ingredient is present in the pesticide composition in the form of suspended particles. The particles can be characterized by a particle size distribution that can be determined by dynamic light scattering technology. A suitable dynamic light scattering measurement unit is produced, inter alia, under the trade name Malvern Mastersizer 3000. The particles can be characterized by their median diameter, commonly abbreviated as the x50 value. The x50 value refers to the specific particle diameter below which half of the particle population by volume is smaller. The x50 value is typically determined in accordance with ISO 13320:2009.
[0020] The particles may have an x50 value of 0.05 μm to 30 μm, preferably 0.1 μm to 20 μm, more preferably 0.5 to 20 μm, most preferably 0.5 μm to 15 μm, and especially preferably 0.5 μm to 10 μm. The particles typically have an x50 value of at least 0.75 μm, preferably at least 1 μm.
[0021] The active ingredient has a water solubility of at least 1 g / L at 20°C. Preferably, the active ingredient has a water solubility of at least 5 g / L, preferably at least 10 g / L, more preferably at least 20 g / L, most preferably at least 30 g / L, especially at least 40 g / L. The active ingredient may have a water solubility of up to 200 g / L, preferably up to 100 g / L, more preferably up to 80 g / L, most preferably up to 60 g / L, and preferably up to 50 g / L at 25°C. The active ingredient may have a water solubility of 15 g / L to 70 g / L, preferably 25 g / L to 40 g / L at 25°C.
[0022] The pesticide composition may contain additional active ingredients which may be selected from fungicides, insecticides, nematicides, herbicides, safeners, micronutrients, biopesticides, nitrification inhibitors, urease inhibitors, and / or growth regulators. The additional active ingredients may be present in the pesticide composition in dissolved form or as suspended particles. In one embodiment, the additional active ingredient is present as an emulsion.
[0023] The concentration of the further active ingredient is typically 1 to 50 wt %, preferably 10 to 25 wt %, based on the total weight of the pesticide composition.
[0024] The active ingredient is of formula I
[0025] [ka] [In the formula, R P1 , R P2 , and R P3are, independently of one another, H, CN, halogen, C1-C4-alkyl, C1-C3-haloalkyl, C1-C4-alkoxy, C1-C3-haloalkoxy, C1-C4-alkylthio, C1-C3-haloalkylthio, C1-C4-alkylsulfinyl, C1-C3-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C3-haloalkylsulfonyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl or C1-C4-alkoxy-C1-C4-alkyl; Z 1 is N or CH; Z 2 is N or CR 4 and; Z 3 is N or CR 5 and; T is S, O, or NR 1b and R 1b H, C1~C 10 -Alkyl, C1-C4-haloalkyl, C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkylmethyl, C3-C 10 -Halocycloalkyl, C2-C 10 -Alkenyl, C2-C 10 -Haloalkenyl, C2-C 10 -Alkynyl, C1-C 10 -alkoxy-C1-C4-alkyl, OR a , 3- to 10-membered heterocyclyl, 3- to 10-membered heterocyclyl-C1-C4-alkyl, aryl, hetaryl, aryl-C1-C4-alkyl, or hetaryl-C1-C4-alkyl, and the cyclic moiety is unsubstituted or has one or more of the same or different substituents R aa is replaced by; R 1 H, CN, C1~C 10 -Alkyl, C1-C 10 -Haloalkyl, C3-C 10 -Cycloalkyl, C3-C 10-halocycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C 10 -Alkenyl, C2-C 10 -Haloalkenyl, C2-C 10 -Alkynyl, C3-C 10 -haloalkynyl, C1-C5-alkylene-CN, OR a , C1-C5-alkylene-OR a , C(Y)R b , C1-C5-alkylene-C(Y)R b , C(Y)OR c , C1-C5-alkylene-C(Y)OR c , S(O)2R d , N.R. e R f , C1-C5-alkylene-NR e R f , C(Y)NR g R h , C1-C5-alkylene-C(Y)NR g R h , S(O) m NR e R f , C(Y)NR i NR e R f , C1-C5-alkylene-S(O)2R d , C1-C5-alkylene-S(O) m NR e R f , C1-C5-alkylene-C(Y)NR i NR e R f , aryl, 3-10 membered heterocyclyl, hetaryl, aryl-C1-C5-alkyl, C3-C 10 -cycloalkyl-C1-C5-alkyl, 3- to 10-membered heterocyclyl-C1-C5-alkyl, or hetaryl-C1-C5-alkyl, wherein the cyclic moiety is unsubstituted or has one or more identical or different substituents R y and / or R x is replaced by; R 2 H, CN, NO2, C1~C 10 -Alkyl, C2-C 10-Alkenyl, C2-C 10 -alkynyl, L 1 -C3~C 10 -cycloalkyl, L 1 -(3- to 6-membered heterocyclyl), L 1 -aryl, or L 1 -heteroaryl, the heterocyclyl group of which may be substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 3A and the cyclic group may contain one or more CO groups, which may be unsubstituted or may contain one or more of the same or different substituents R x is replaced by; L 1 is a direct bond, C1-C8-alkylene, C2-C8-alkenylene, C2-C8-alkynylene, or C3-C6-cycloalkylene, and the C atoms are unsubstituted or substituted with one or more identical or different substituents R x is replaced by; R 3 H, halogen, CN, C1-C 10 -Alkyl, C1-C 10 -Haloalkyl, C1-C 10 -alkoxy or C1-C 10 -haloalkoxy, R 4 , R 5 independently (i) H, CN, NO2, halogens, C1-C 10 -Alkyl, C2-C 10 -alkenyl, or C2-C 10 -alkynyl, and the C atoms are unsubstituted or have one or more identical or different substituents R x is substituted with; or OR a , S.R. d , C(Y)R b , C(Y)OR c , S(O)R d , S(O)2R d , N.R. e R f , C(Y)NR g R h , S(O) m NRe R f , C(Y)NR i NR e R f , C1-C5-alkylene-OR a , C1-C5-alkylene-CN, C1-C5-alkylene-C(Y)R b , C1-C5-alkylene-C(Y)OR c , C1-C5-alkylene-NR e R f , C1-C5-alkylene-C(Y)NR g R h , C1-C5-alkylene-S(O) m R d , C1-C5-alkylene-S(O) m NR e R f , C1-C5-alkylene-NR i NR e R f or 3-10 membered heterocyclyl, hetaryl, C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkenyl, aryl, 3-10 membered heterocyclyl-C1-C5-alkyl, hetaryl-C1-C5-alkyl, C3-C 10 -Cycloalkyl-C1-C5-alkyl, C3-C 10 -cycloalkenyl-C1-C5-alkyl or aryl-C1-C5-alkyl, the cyclic moiety being unsubstituted or substituted by one or more of the same or different substituents R y is replaced by; or R 4 teeth, (ii)L 2 -C3~C 10 -cycloalkenyl, L 2 -C3~C 10 -cycloalkenyloxy, or L 2 -C3~C 10 -cycloalkenylthio, wherein the cycloalkenyl ring is unsubstituted or has one or more of the same or different substituents R y is replaced by; L 2is C1-C8-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or C3-C6-cycloalkylene, the C atoms being unsubstituted or substituted with one or more identical or different substituents R x is replaced by; or R 4 teeth, (iii) any one of the following groups:
[0026] [ka] R 4a , R 4b and R 4c are, independently of each other, H, halogen, CN, NO2, C1-C 10 -Alkyl, C2-C 10 -alkenyl, or C2-C 10 -alkynyl, and the C atoms are unsubstituted or have one or more identical or different substituents R x is replaced by; C1~C 10 -Haloalkyl, C1-C 10 -alkoxy, or C1-C4-alkoxy-C1-C 10 -alkyl, and the C atoms are unsubstituted or have one or more identical or different substituents R y is replaced by; OR a , S.R. a , C(Y)R b , C(Y)OR c , C(Y)NR g R h , C(Y)NR i NR e R f , S(O) m R d , S(O) m NR e R f , C1-C5-alkylene-OR a , C1-C5-alkylene-CN, C1-C5-alkylene-C(Y)R b , C1-C5-alkylene-C(Y)OR c , C1-C5-alkylene-NRe R f , C1-C5-alkylene-C(Y)NR g R h , C1-C5-alkylene-S(O) m R d , C1-C5-alkylene-S(O) m NR e R f or C1-C5-alkylene-NR i NR e R f ; 3-10 membered heterocyclyl, C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkenyl, hetaryl, aryl, 3-10 membered heterocyclyl-C1-C5-alkyl, C3-C 10 -Cycloalkyl-C1-C5-alkyl, C3-C 10 -cycloalkenyl-C1-C5-alkyl, hetaryl-C1-C5-alkyl, or aryl-C1-C5-alkyl, the cyclic moiety being unsubstituted or substituted by one or more of the same or different substituents R y is replaced by; A is a 3- to 12-membered non-aromatic carbocyclic or heterocyclic ring, the heterocyclic ring containing one or more of the same or different heteroatoms N, O, or S, which may be oxidized, and the carbocyclic or heterocyclic ring is unsubstituted or contains one or more of the same or different substituents R j and / or R l is replaced by; D is a direct bond, C1-C6-alkylene, C2-C6-alkenylene, or C2-C6-alkynylene, and the carbon chain is unsubstituted or has one or more of the same or different substituents R n is replaced by; E is a non-aromatic 3- to 12-membered carbocyclic or heterocyclic ring, the heterocyclic ring containing one or more of the same or different heteroatoms N, O, or S, which may be oxidized, and the carbocyclic or heterocyclic ring is unsubstituted or contains one or more of the same or different substituents R n and / or R l is replaced by; R 4dis C1-C4-haloalkyl or C3-C6-cycloalkyl, each of which may be halogenated; G is C1-C6-alkylene, C2-C6-alkenylene, C2-C6-alkynylene, C3-C6-cycloalkylene or C3-C6-cycloalkenylene, the C atoms being unsubstituted or substituted with one or more identical or different substituents R p is replaced by; or R 4 teeth, (iv) any one of the following groups:
[0027] [ka] R 4e is H, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, or a 3- to 6-membered heterocycle, which heterocycle contains one or more identical or different heteroatoms N, O, or S, which S may be oxidized, and which group is unsubstituted or contains one or more identical or different substituents R r and / or R l is replaced by; Q is a direct bond, C1-C8-alkylene, C2-C8-alkenylene, or C2-C8-alkynylene, and the carbon chain is unsubstituted or has one or more of the same or different substituents R r is substituted with; or Q and R 4e together with the imidazole form a 3- to 6-membered carbocyclic ring or a 4- to 6-membered heterocyclic ring having a direct bond, the heterocyclic ring containing one or more of the same or different heteroatoms N, O, or S, which may be oxidized, and the ring is unsubstituted or contains one or more of the same or different substituents R r and / or R l is replaced by; M is O, S, NR M , NOR M , or NSR M and; R M is R4e or R M and Q together form a 4-6 membered unsaturated, non-aromatic N-containing heterocycle, which may contain additional heteroatoms O or S, which may be oxidized, and which may be unsubstituted or may contain one or more of the same or different substituents R r is replaced by; R 4g is H, C1-C6-alkyl, C1-C6-alkyl-X, C3-C6-cycloalkyl, or C3-C6-cycloalkyl-X; and R 4f is C1-C6-alkyl, C1-C6-alkyl-X, C3-C6-cycloalkyl or C3-C6-cycloalkyl-X; the C1-C6-alkyl or C3-C6-cycloalkyl group is unsubstituted or has one or more identical or different substituents R t is replaced by; X is O, S, NH or NR l is; or R 4g and R 4f together with the carbon atoms to which they are attached form a 3- to 8-membered, saturated or unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which carbocyclic or heterocyclic ring is unsubstituted or contains one or more of the same or different substituents R t and / or R l is replaced by; W is C1-C8-alkylene, C3-C8-cycloalkylene, C3-C8-heterocycloalkylene, C2-C8-alkenylene, C3-C8-cycloalkenylene, C3-C8-heterocycloalkenylene, or C2-C8-alkynylene, and W is unsubstituted or substituted with one or more of the same or different substituents R t and / or R l is replaced by; V is O, S or NR 1a and R 1a H, C1~C 10-Alkyl, C1-C4-haloalkyl, C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkylmethyl, C3-C 10 -Halocycloalkyl, C2-C 10 -Alkenyl, C2-C 10 -Haloalkenyl, C2-C 10 -Alkynyl, C1-C 10 -alkoxy-C1-C4-alkyl, OR a , 3- to 10-membered heterocyclyl, 3- to 10-membered heterocyclyl-C1-C4-alkyl, aryl, hetaryl, aryl-C1-C4-alkyl, or hetaryl-C1-C4-alkyl, and the cyclic moiety is unsubstituted or has one or more of the same or different substituents R aa is substituted with; or R 1a and R 4g is R 4g and the carbon atom to which R is bonded 1a is bonded to the nitrogen atom and the nitrogen atom between the carbon atom and the nitrogen atom to form a 4- to 8-membered heterocycle, the heterocycle containing two nitrogen atoms as heteroatoms and optionally containing one or more of the same or different heteroatoms N, O, or S, wherein S is optionally oxidized, and the heterocycle is unsubstituted or contains one or more of the same or different substituents R t and / or R l is replaced by; or R 4 teeth, (v)(va)S(O) m -R 4h , (vb) OR 4i , or (vc)NR 4j R 4k is one of the groups R 4h , R 4i are, independently of each other, CN; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic group being unsubstituted or having one or more identical or different substituents R A1 is replaced by; C3-C8-cycloalkyl, C5-C8-cycloalkenyl, or 3- to 8-membered heterocyclyl, wherein the heterocyclyl group contains one or more of the same or different heteroatoms O, N, S(O) m or NR 3A The cyclic group contains one or more of the same or different C(G A )R 2A The cyclic group may be unsubstituted or may contain one or more of the same or different substituents R A4 is replaced by; C3-C8-cycloalkyl-C1-C4-alkyl, C5-C8-cycloalkenyl-C1-C4-alkyl or 3-8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 3A The cyclic group contains one or more of the same or different C(G A )R 2A groups, the C atoms of which may be unsubstituted or may be substituted with one or more of the same or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A5 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A6 is replaced by; G A is O, N-CN, or N-OR 2A and; R 2A is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C5-C8-cycloalkenyl, or 3- to 8-membered heterocyclyl, wherein the heterocyclyl group contains one or more of the same or different heteroatoms O or S(O)m The cyclic group may be unsubstituted or may contain one or more of the same or different substituents R A4 is replaced by; C3-C8-cycloalkyl-C1-C4-alkyl, C5-C8-cycloalkenyl-C1-C4-alkyl or 3-8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is selected from the group consisting of one or more of the same or different heteroatoms O or S(O) m and the C atoms of these groups are unsubstituted or are substituted with one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A6 is replaced by; R 3A is H; C1-C6-alkyl, C3-C6-alkenyl, or C3-C6-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more of the same or different substituents R A3 is substituted with; or CONR 2A R 4A or COR 2A and; R 4A is H; C1-C6-alkyl, C3-C6-alkenyl, or C3-C6-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; and R 4j is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is substituted with; or C(O)R 2B , C(O)NR 3B R 4B , C(O)OR 5B , SO2R 6B and; R 4k is H;NR 3aB R 4aB ; C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, or C1-C4-alkoxy, the aliphatic group being unsubstituted or having one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 4aB and the cyclic group may contain one or more CO groups, the C atoms of which are unsubstituted or substituted by one or more of the same or different substituents R A4 is substituted with; or Aryl, aryl-C1-C4-alkyl, hetaryl or hetaryl-C1-C4-alkyl, the C atoms of these groups are unsubstituted or substituted with one or more identical or different substituents R A6 is substituted with; or R 4j and R 4k together with the nitrogen atom to which they are attached form a 3- to 7-membered heterocycle, which contains a nitrogen atom as a heteroatom and one or more of the same or different heteroatoms O, N, S(O) m or N, and the ring may be unsubstituted or may contain one or more of the same or different substituents R A8 is replaced by; R 2B , R 3B , R4B are, independently of one another, H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or contain one or more identical or different substituents R A6 is replaced by; R 3aB is H; C1-C8-alkyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or contain one or more identical or different substituents R A6 is replaced by; R 4aB is H; C1-C4-alkyl, the aliphatic groups of which are unsubstituted or substituted with one or more identical or different substituents selected from halogen or C1-C4-alkoxy; C3-C6-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is substituted with; or C(O)R2B , C(O)OR 5B , or SO2R 6B and R 5B is C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic groups of which are unsubstituted or substituted with one or more, identical or different, substituents selected from halogen or C1-C4-alkoxy; or C3-C6-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is replaced by; R 6B is C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic group being unsubstituted or having one or more identical or different substituents R A3 is replaced by; C3-C6-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is substituted with; or aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is replaced by; or R 4 teeth, (vi)(via)C(T 1 )R 4l , (vib)C(O)OR 4m , (vic)C(Y)NR 4n R 4o , or (vid)C(Y)NR 4p NR 4q R 4r is one of the groups R 4l is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl or 3- to 8-membered heterocyclyl, the heterocyclyl group containing one or more of the same or different heteroatoms O or S(O) m The cyclic group may be unsubstituted or may contain one or more of the same or different substituents R A4 is replaced by; C3-C8-cycloalkyl-C1-C4-alkyl or 3-8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group contains one or more of the same or different heteroatoms O or S(O) m and the C atoms of these groups are unsubstituted or are substituted with one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A6 is replaced by; and T 1 O, N-OR 1C , N-NR 2C R 3C , or
[0028] [ka] and # is C(T 1 )R 4l Group C(T 1 ) moiety with a carbon atom; L A and L B are independently O or S(O) m and; A 1 is C2-C4-alkylene, the C atoms are unsubstituted or substituted with one or more identical or different substituents R 4C is replaced by; and R1C is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is replaced by; C-C-cycloalkyl-C-C-alkyl, the C atoms of these groups are unsubstituted or substituted by one or more identical or different substituents R A4 is replaced by; aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A6 is replaced by; R 2C is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which groups are unsubstituted or have one or more identical or different substituents R A4 is replaced by; R 3C is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 3Aand the cyclic group may contain one or more CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 4C is halogen; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; aryl, which groups are unsubstituted or have one or more of the same or different substituents R A6 is substituted with; or Two Rs attached to the same carbon atom 4C form a C2-C4-alkylene chain, which is unsubstituted or has one or more identical or different substituents R A4 is substituted with; or Two Rs attached to the same carbon atom 4C forms a C1-C4-alkenylene chain, the double bond of which is attached to said carbon atom, and which chain is unsubstituted or has one or more of the same or different substituents R A4 is replaced by; R 4m is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is replaced by; C-C-cycloalkyl-C-C-alkyl, the C atoms of these groups are unsubstituted or substituted by one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A6 is replaced by; R 4n is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C1-C4-alkylsulfonyl, C3-C6-cycloalkylsulfonyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl, which groups are unsubstituted or have one or more identical or different substituents R A4 is substituted with; or phenyl-C1-C2-alkoxycarbonyl, the C atoms of these groups are unsubstituted or substituted with one or more identical or different substituents R A6 is replaced by; R 4o is H; C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C4-alkoxy, the aliphatic radicals being unsubstituted or having one or more identical or different substituents R A2 is replaced by; C3-C8-cycloalkyl or 3- to 8-membered heterocyclyl, the heterocyclyl group containing one or more of the same or different heteroatoms O, N, S(O) m or NR 3A and the cyclic group may contain one or more CO groups, and the cyclic group may be unsubstituted or may contain one or more of the same or different substituents R A4 is replaced by; C3-C8-cycloalkyl-C1-C4-alkyl or 3-8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 4A and the cyclic group may contain one or more CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A7 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A7 is substituted with; or R 4n and R 4o together with the nitrogen atom to which they are attached form a 3- to 8-membered heterocycle, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which is unsubstituted or contains one or more of the same or different substituents R A4 is replaced by; R 4p is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which groups are unsubstituted or have one or more identical or different substituents R A4 is replaced by; R 4q is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which groups are unsubstituted or have one or more identical or different substituents R A4 is replaced by; R 4r is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 3A and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; or R 4 teeth, (vii)R 4s and R 4s is aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more of the same or different substituents R 1D is replaced by; R 1D CN, NO2, halogen, NR 2D R 3D ;C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-S(O) m-, C1-C4-haloalkyl-S(O) m -, carboxy; or aryl, or hetaryl, which groups are unsubstituted or contain one or more of the same or different substituents R A6 is substituted with; or Two adjacent R 1D Groups, taken together with the adjacent atoms to which they are attached, form a fused 3- to 8-membered heterocyclic ring, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which are unsubstituted or contain one or more of the same or different substituents R A6 is replaced by; R 2D is H; C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, which groups are unsubstituted or contain one or more identical or different substituents R A3 or R A4 is replaced by; R 3D is H; C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, which groups are unsubstituted or contain one or more identical or different substituents R A3 or R A4 is substituted with; or R 2D and R 3D together with the nitrogen atom to which they are attached form a 3- to 8-membered heterocycle, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which is unsubstituted or contains one or more of the same or different substituents R A6 is replaced by; or R 4 teeth, (viii)CR 4t R 4u R 4v and R 4tis H; CN; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl or 3- to 8-membered heterocyclyl, wherein the heterocyclyl group contains one or more of the same or different heteroatoms O, N, S(O) m or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 4u is H; C1-C4-alkyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is substituted with; or R 4t and R 4u together with the carbon atoms to which they are attached form a 3- to 8-membered carbocyclic or heterocyclic ring, which heterocyclic ring may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1Fwherein the cyclic group may contain one or more of the same or different CO groups, and the carbocyclic or heterocyclic ring may be unsubstituted or may contain one or more of the same or different substituents R A3 is substituted with; or R 4t and R 4u are both C2-C6-alkenyl, the aliphatic groups of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; R 4v is H;S(O) m R 1E , OR 2E , or N(R 3E )(R 4E ) and R 4t and / or R 4u is H or C1-C8-alkyl, the aliphatic group may be unsubstituted or may contain one or more of the same or different substituents R A3 is substituted with R 4v is S(O) m R 1E , OR 2E , or N(R 3E )(R 4E ) and; R 1E is C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic group being unsubstituted or containing one or more identical or different substituents R A9 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 2E is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A9 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 3E is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 4E is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents RA3 is substituted with; or C(O)N(R 5E )(R 6E ), C(O)R 7E , C(O)OR 8E , or SO2R 9E is; or R 3E and R 4E together with the nitrogen atom to which they are attached form a 3- to 9-membered heterocycle, the heterocyclyl group of which may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A8 is substituted with; or R 5E and R 6E are, independently of one another, H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl or 3- to 8-membered heterocyclyl, wherein the heterocyclyl group contains one or more of the same or different heteroatoms O, N, S(O) m or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is substituted with; or R 5E and R 6E together with the nitrogen atom to which they are attached form a 3- to 8-membered heterocyclic ring, which heterocyclic ring may contain one or more of the same or different heteroatoms O, or S(O) m and the heterocycle is unsubstituted or contains one or more of the same or different substituents R A10 is replaced by; R 7E is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 8E is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 9E is C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic group being unsubstituted or containing one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 1F is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, the C atoms of these groups are unsubstituted or are substituted by one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents RA6 is replaced by; and R a , R b , R c are, independently from one another, H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6-cycloalkenylmethyl, C3-C6-halocycloalkenyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, 3- to 6-membered heterocyclyl, 3- to 6-membered heterocyclyl-C1-C4-alkyl, aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, and the cyclic moiety is unsubstituted or is substituted by one or more identical or different substituents R aa is replaced by R d is H, C1-C4-alkoxy, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6-cycloalkenylmethyl, C3-C6-halocycloalkenyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, 3- to 6-membered heterocyclyl, 3- to 6-membered heterocyclyl-C1-C4-alkyl, aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the cyclic moiety of which is unsubstituted or is substituted by one or more of the same or different substituents R aa is replaced by; R e , R fare, independently of one another, H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6-cycloalkenylmethyl, C3-C6-halocycloalkenyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, 3- to 6-membered heterocyclo aryl, 3- to 6-membered heterocyclyl-C1-C4-alkyl, 3- to 6-membered heterocyclylcarbonyl, 3- to 6-membered heterocyclyl-C1-C4-alkyl-carbonyl, 3- to 6-membered heterocyclyl-C1-C4-alkyl-sulfonyl, aryl, arylcarbonyl, aryl-C1-C4-alkyl-carbonyl, arylsulfonyl, hetaryl, hetaryl-C1-C4-alkyl-carbonyl, hetarylcarbonyl, hetarylsulfonyl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the cyclic moiety of which is unsubstituted or is substituted by one or more of the same or different substituents R aa is substituted with; or R e and R f together with the nitrogen atom to which they are attached form a 5- or 6-membered, saturated or unsaturated heterocycle, which may further contain heteroatoms O, S, or N, where S may be oxidized, and which may be unsubstituted or may contain one or more of the same or different substituents R aa is replaced by; R g , R hare, independently from one another, H, C1-C4-alkyl, C1-C4-haloalkyl, L-C3-C6-cycloalkyl, L-C3-C6-halocycloalkyl, L-C3-C6-cycloalkenyl, L-C3-C6-halocycloalkenyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, 3- to 6-membered heterocyclyl, 3- to 6-membered heterocyclyl-C1-C4-alkyl, aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, and the cyclic moiety is unsubstituted or is substituted by one or more identical or different substituents R aa is replaced by; R i is H, CN, C1-C4-alkyl, C1-C4-haloalkyl, L-C3-C6-cycloalkyl, L-C3-C6-halocycloalkyl, L-C3-C6-cycloalkenyl, L-C3-C6-halocycloalkenyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, aryl or aryl-C1-C4-alkyl, the aryl ring being unsubstituted or containing one or more identical or different substituents R aa is replaced by; R bonded to C j are halogens, OH, CN, NO2, C1-C 10 -Alkyl, C1-C 10 -Haloalkyl, C1-C 10 -Alkoxy, C1-C 10 -haloalkoxy, S(O) m R k , C3-C6-cycloalkyl, or a 3- to 6-membered heterocycle, which heterocycle contains one or more of the same or different heteroatoms N, O, or S, where S may be oxidized; R j The group may be unsubstituted or may contain one or more of the same or different substituents R m and / or R l and two R attached to the same or adjacent ring atoms jThe groups together can form a 3- to 6-membered carbocyclic or heterocyclic ring, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which ring is unsubstituted or contains one or more of the same or different substituents R m and / or R l is replaced by; R k is H, C1-C4-alkyl, C1-C4-haloalkyl, or C3-C6-cycloalkyl, the ring being unsubstituted or containing one or more identical or different substituents R l is replaced by; R bonded to N l is C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, or C1-C4-alkoxycarbonyl; R bonded to C m is halogen, OH, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, or S(O) m R k and; R bonded to C n is halogen, CN, NO2, C1-C2-alkyl, C1-C4-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylidene, =O, =S, =NR 1o , =NOR 1o , =NSR 1o , or S(O) m R 1o or two adjacent R n The groups, together with the atoms to which they are attached, form a 3- to 8-membered carbocyclic or heterocyclic ring, which heterocyclic ring contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and the R n The moiety may be unsubstituted or may contain one or more of the same or different substituents halogen, R o , and / or Rl is replaced by; R 1o is H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, or C1-C4-alkoxy; R bonded to C o is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, or C1-C4-alkoxycarbonyl; R p is halogen, CN, NO, C-C-alkyl, C-C-haloalkyl, C-C-cycloalkyl, C-C-alkoxy or C-C-haloalkoxy, or two R p The groups together can form a 3- to 6-membered carbocyclic or heterocyclic ring, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which carbocyclic or heterocyclic ring is unsubstituted or contains one or more of the same or different substituents R q is replaced by; R q is halogen, CN, NO, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy, R bonded to C r is halogen, CN, NO2, C1-C2-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C2-haloalkoxy, or S(O) m R k or two R r The groups together form a 3- to 6-membered carbocyclic or heterocyclic ring, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which carbocyclic or heterocyclic ring is unsubstituted or s is replaced by; R sis halogen, CN, NO2, C1-C2-alkyl, C1-C2-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy or C1-C2-haloalkoxy, R bonded to C t is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-halocycloalkyl, C3-C6-halocycloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, S(O) m R w , =O, =S, =NR v , =NOR v , or =NSR v or two R attached to the same carbon atom or adjacent carbon atoms t together with the carbon atoms to which they are attached form a 3- to 6-membered, saturated or unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and N may be unsubstituted or may be substituted with one or more of the same or different substituents R l is replaced by; R v is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, or C3-C6-halocycloalkyl; R w is H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy, R x is halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, S(O) m R d , S(O) m NR e R f , N.R. e R f , C(O)NR g R h , C1~C10 -alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C3-C6-cycloalkyl, 5- to 7-membered heterocyclyl, 5- or 6-membered hetaryl, aryl, C3-C6-cycloalkoxy, 3- to 6-membered heterocyclyloxy, or phenoxy, and the cyclic moiety is unsubstituted or substituted by one or more of the same or different substituents R y is replaced by; R y is halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, S(O) m R d , S(O) m NR e R f , C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, or C1-C4-alkoxy-C1-C4-alkyl; R aa is halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; R A1 is CN, halogen, C1-C4-alkoxy, C1-C4-alkyl-S(O) m -, C(O)R 2A , C(O)NR 2A R 3A , or C(G A )R 2A and; R A2 is CN, halogen, OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl, or C1-C4-alkyl-S(O) m - and; R A3 is CN, halogen, C1-C4-alkoxy, or C1-C4-alkyl-S(O) m- and; R A4 is CN, halogen, C1-C4-alkyl, C1-C4-haloalkyl, or C1-C4-alkoxy; R A5 is CN, NO2, halogen, oxime ether, acyl amide, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-S(O) m -, C1-C4-haloalkyl-S(O) m -or aryl, aryloxy, hetaryl, or hetaryloxy, and the aromatic group is unsubstituted or has one or more of the same or different substituents R Z1 is replaced by; R Z1 is CN, NO2, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-S(O) m -, C1-C4-haloalkyl-S(O) m -, hetaryloxy, or aryloxy; R A6 is CN, NO2, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-S(O) m - or C1-C4-haloalkyl-S(O) m - and; R A7 is CN, NO2, halogen, C1-C4-alkyl, C1-C4-haloalkyl, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-S(O) m - or C1-C4-haloalkyl-S(O) m - and; R A8is H, CN, NO2, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C5-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-halocycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, cyano-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C1-C4-alkyl-S(O) m -, C1-C4-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, di-(C1-C6)-alkylaminocarbonyl, C1-C6-alkylcarbonylamino, aryl or hetaryl, the aryl or hetaryl group being unsubstituted or having one or more identical or different substituents R Z2 is replaced by; R Z2 is CN, NO2, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C6-haloalkoxy, or C1-C4-alkylthio; R A9 is CN, halogen, C1-C4-alkoxy, C1-C4-alkyl-S(O) m -, C(O)OR 2A , C(O)NR 2A R 3A , or C(G A )R 2A and; R A10 is C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy; Y is O or S; m is 0, 1 or 2. and salts, stereoisomers, tautomers, and N-oxides thereof.
[0029] Compounds of formula I and methods for their preparation are known and are described, inter alia, in WO 2018 / 029102, WO 2016 / 128298, WO 2018 / 210625, WO 2011 / 009804, WO 2010 / 034737, WO 2016 / 180833, PCT / EP2019 / 050537, and EP 16197196.5. If some compounds falling within the definition of formula I are not obtainable by standard methods or by the methods provided in the prior art documents cited in this paragraph, they may be obtained from other compounds of formula I by methods and techniques known to those skilled in the art, as is common knowledge.
[0030] The term "active ingredient," or "compound of Formula I," includes compounds as defined herein as well as stereoisomers, salts, tautomers, or N-oxides thereof.
[0031] The groups attached to the backbone of formula I may contain one or more chiral centers. In this case, the compounds of formula I exist in different enantiomeric or diastereomeric forms depending on the substituents. The present invention relates to all possible stereoisomers of formula I, i.e., single enantiomers or diastereomers, as well as mixtures thereof.
[0032] As already mentioned above, compounds of formula I may also be used, for example, in the presence of R 4 Depending on the selection of groups, different tautomeric forms may exist. The present invention relates to all possible tautomers of formula I.
[0033] As already mentioned above, compounds of formula I can be prepared by, for example, R 4 Where geometric isomerism is possible, the present invention relates to both the E- and Z-isomers of the compounds of formula I.
[0034] The compounds of formula I may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties, e.g., stability, or exhibit different biological properties, e.g., activity. The present invention relates to amorphous and crystalline forms of compounds of formula I, mixtures of the different crystalline states of each compound I, as well as amorphous or crystalline salts thereof.
[0035] Salts of compounds of formula I are preferably veterinarily and / or agriculturally acceptable salts, preferably agriculturally acceptable salts, which may be formed in a conventional manner, for example, if the compound of formula I contains a basic functional group, by reacting the compound with an acid of the desired anion.
[0036] Veterinarily and / or agriculturally useful salts of the compounds of formula I include in particular the acid addition salts of those acids whose cations and anions, respectively, do not adversely affect the pesticidal action of the compounds of formula I.
[0037] The anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4 alkanoic acids, preferably formate, acetate, propionate, and butyrate. They can be formed by reacting compounds of formula I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, or nitric acid.
[0038] The term "N-oxide" includes any compound of Formula I having at least one tertiary nitrogen atom oxidized to an N-oxide moiety.
[0039] The organic moieties shown in the above definitions of the variables are collective terms for the individual enumerations of the individual group members, like the term halogen. n ~C m indicates in each case the possible number of carbon atoms in the group.
[0040] The term "halogen" denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine and bromine.
[0041] The term "alkyl," as used herein, as well as in the alkyl portion of alkylamino, alkylcarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, and alkoxyalkyl, denotes in each case a straight-chain or branched alkyl group typically having 1 to 10 carbon atoms, frequently 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and more preferably 1 to 3 carbon atoms. Examples of alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl.
[0042] The term "haloalkyl," as used herein and in the haloalkyl moieties of haloalkylcarbonyl, haloalkoxycarbonyl, haloalkylthio, haloalkylsulfonyl, haloalkylsulfinyl, haloalkoxy, and haloalkoxyalkyl, in each case denotes a straight-chain or branched alkyl group, typically having 1 to 10 carbon atoms, frequently 1 to 6 carbon atoms, and preferably 1 to 4 carbon atoms, in which the hydrogen atoms of the group have been partially or completely replaced by halogen atoms. Preferred haloalkyl moieties are selected from C1-C4-haloalkyl, more preferably C1-C3-haloalkyl or C1-C2-haloalkyl, and in particular C1-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like.
[0043] The term "alkoxy" as used herein denotes in each case a straight-chain or branched alkyl group attached via an oxygen atom and typically having 1 to 10 carbon atoms, frequently 1 to 6 carbon atoms, and preferably 1 to 4 carbon atoms. Examples of alkoxy groups are methoxy, ethoxy, n-propoxy, iso-propoxy, n-butyloxy, 2-butyloxy, iso-butyloxy, tert.-butyloxy, etc.
[0044] The term "alkoxyalkyl" as used herein refers to an alkyl, typically containing 1 to 10, frequently 1 to 4, and preferably 1 to 2 carbon atoms, with one carbon atom bearing an alkoxy group, as defined above, typically containing 1 to 4, and preferably 1 or 2 carbon atoms. Examples are CHOCH, CH-OCH, 2-(methoxy)ethyl, and 2-(ethoxy)ethyl.
[0045] The term "haloalkoxy" as used herein denotes, in each case, a straight-chain or branched alkoxy group having 1 to 10 carbon atoms, frequently 1 to 6 carbon atoms, and preferably 1 to 4 carbon atoms, in which the hydrogen atoms of the group have been partially or entirely replaced by halogen atoms, in particular fluorine atoms. Preferred haloalkoxy moieties include C1-C4-haloalkoxy, in particular C1-C2-fluoroalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, and the like.
[0046] The term "alkylthio" (alkylsulfanyl: alkyl-S-) as used herein refers to a linear or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (=C1-C4-alkylthio), more preferably 1 to 3 carbon atoms, bonded via a sulfur atom.
[0047] The term "haloalkylthio," as used herein, refers to an alkylthio group as defined above, wherein the hydrogen atoms are partially or fully replaced by fluorine, chlorine, bromine and / or iodine.
[0048] The term "alkylsulfinyl" (alkylsulfoxyl: C1-C6-alkyl-S(=O)-), as used herein, refers to a linear or branched saturated alkyl group (as described above) having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (=C1-C4-alkylsulfinyl), more preferably 1 to 3 carbon atoms, bonded at any position of the alkyl group through the sulfur atom of the sulfinyl group.
[0049] The term "haloalkylsulfinyl," as used herein, refers to an alkylsulfinyl group as defined above, wherein the hydrogen atoms are partially or fully replaced by fluorine, chlorine, bromine and / or iodine.
[0050] The term "alkylsulfonyl" (alkyl-S(=O)2-), as used herein, refers to a linear or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (=C1-C4-alkylsulfonyl), preferably 1 to 3 carbon atoms, bonded at any position of the alkyl group via the sulfur atom of the sulfonyl group.
[0051] The term "haloalkylsulfonyl," as used herein, refers to an alkylsulfonyl group as defined above, wherein the hydrogen atoms are partially or fully replaced by fluorine, chlorine, bromine and / or iodine.
[0052] The term "alkylcarbonyl" refers to an alkyl group, as defined above, attached to the remainder of the molecule through the carbon atom of a carbonyl group (C=O).
[0053] The term "haloalkylcarbonyl" refers to an alkylcarbonyl group as defined above in which the hydrogen atoms are partially or fully replaced by fluorine, chlorine, bromine and / or iodine.
[0054] The term "alkoxycarbonyl" refers to an alkylcarbonyl group, as defined above, attached to the remainder of the molecule through an oxygen atom.
[0055] The term "haloalkoxycarbonyl" refers to an alkoxycarbonyl group as defined above in which the hydrogen atoms are partially or fully replaced by fluorine, chlorine, bromine and / or iodine.
[0056] The term "alkenyl", as used herein, denotes in each case a singly unsaturated hydrocarbon group, typically having 2 to 10, frequently 2 to 6, and preferably 2 to 4 carbon atoms, such as vinyl, allyl (2-propen-1-yl), 1-propen-1-yl, 2-propen-2-yl, methallyl (2-methylprop-2-en-1-yl), 2-buten-1-yl, 3-buten-1-yl, 2-penten-1-yl, 3-penten-1-yl, 4-penten-1-yl, 1-methylbut-2-en-1-yl, 2-ethylprop-2-en-1-yl, and the like.
[0057] The term "haloalkenyl," as used herein, refers to an alkenyl group as defined above in which the hydrogen atoms have been partially or fully replaced with halogen atoms.
[0058] The term "alkynyl", as used herein, denotes in each case a monounsaturated hydrocarbon group, typically having 2 to 10, frequently 2 to 6, and preferably 2 to 4 carbon atoms, such as, for example, ethynyl, propargyl (2-propyn-1-yl), 1-propyn-1-yl, 1-methylprop-2-yn-1-yl), 2-butyn-1-yl, 3-butyn-1-yl, 1-pentyn-1-yl, 3-pentyn-1-yl, 4-pentyn-1-yl, 1-methylbut-2-yn-1-yl, 1-ethylprop-2-yn-1-yl, and the like.
[0059] The term "haloalkynyl," as used herein, refers to an alkynyl group as defined above in which the hydrogen atoms have been partially or fully replaced with halogen atoms.
[0060] The term "cycloalkyl", as used herein and in the cycloalkyl portions of cycloalkylalkyl, cycloalkoxy and cycloalkylthio, denotes in each case a monocyclic alicyclic group typically having 3 to 10 or 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl or cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
[0061] The term "halocycloalkyl", as used herein and in the halocycloalkyl moieties of halocycloalkoxy and halocycloalkylthio, denotes a monocyclic alicyclic group, typically having in each case 3 to 10 C atoms or 3 to 6 C atoms, in which at least one, for example 1, 2, 3, 4 or 5 hydrogen atoms have been replaced by halogen, more particularly fluorine or chlorine. Examples are 1- and 2-fluorocyclopropyl, 1,2-, 2,2- and 2,3-difluorocyclopropyl, 1,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 1-, 2- and 3-fluorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1-, 2- and 3-chlorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlorocyclopentyl, and the like.
[0062] The term "cycloalkoxy" refers to a cycloalkyl group, as defined above, attached to the remainder of the molecule through an oxygen atom.
[0063] The term "halocycloalkoxy" refers to a halocycloalkyl group, as defined above, attached to the remainder of the molecule through an oxygen atom.
[0064] The term "cycloalkylthio" refers to a cycloalkyl group, as defined above, attached to the remainder of the molecule through a sulfur atom.
[0065] The term "halocycloalkylthio" refers to a halocycloalkyl group, as defined above, attached to the remainder of the molecule through a sulfur atom.
[0066] The term "cycloalkylalkyl" refers to a cycloalkyl group as defined above, which is bonded to the rest of the molecule via an alkyl group, for example a C1-C5-alkyl group or a C1-C4-alkyl group, in particular a methyl group (=cycloalkylmethyl).
[0067] The term "cycloalkylsulfonyl" refers to a cycloalkyl group attached to the rest of the molecule through the sulfur atom of a sulfonyl group.
[0068] The term "cycloalkenyl," as used herein and in the cycloalkenyl portions of cycloalkenylalkyl, cycloalkenyloxy, and cycloalkenylthio, refers to a monocyclic, monounsaturated, non-aromatic group, typically having 3 to 10, e.g., 3, 4, or 5 to 10, carbon atoms, preferably 3 to 8, and more preferably 3 to 6 carbon atoms, in each case. A cycloalkenyl group can be attached to the remainder of the molecule through a carbon atom that forms a double bond or through a carbon atom that forms a single bond, preferably through a carbon atom that forms a double bond. Exemplary cycloalkenyl groups include cyclopropen-1-yl, cyclohexen-1-yl, cyclohepten-1-yl, or cycloocten-1-yl.
[0069] The term "halocycloalkenyl," as used herein and in the halocycloalkenyl moieties of halocycloalkenyloxy and halocycloalkenylthio, refers to a monocyclic, monounsaturated, non-aromatic group, typically having 3 to 10, e.g., 3, 4, or 5 to 10, carbon atoms, preferably 3 to 8, and more preferably 3 to 6, carbon atoms, in each case in which at least one, e.g., 1, 2, 3, 4, or 5, hydrogen atom has been replaced by a halogen, more particularly fluorine or chlorine. The halocycloalkenyl group can be attached to the remainder of the molecule through a carbon atom that forms a double bond or through a carbon atom that forms a single bond, preferably through a carbon atom that forms a double bond. Examples are 3,3-difluorocyclopropen-1-yl and 3,3-dichlorocyclopropen-1-yl.
[0070] The term "cycloalkenyloxy" refers to a cycloalkenyl group, as defined above, attached to the remainder of the molecule through an oxygen atom.
[0071] The term "halocycloalkenyloxy" refers to a halocycloalkenyl group, as defined above, attached to the remainder of the molecule through an oxygen atom.
[0072] The term "cycloalkenylthio" refers to a cycloalkenyl group, as defined above, attached to the remainder of the molecule through a sulfur atom.
[0073] The term "halocycloalkenylthio" refers to a halocycloalkenyl group, as defined above, attached to the remainder of the molecule through a sulfur atom.
[0074] The term "cycloalkenylalkyl" refers to a cycloalkenyl group as defined above, which is bonded to the rest of the molecule via an alkyl group, for example a C1-C5-alkyl group or a C1-C4-alkyl group, in particular a methyl group (=cycloalkenylmethyl).
[0075] The term "carbocycle" or "carbocyclyl" generally includes a 3- to 12-membered, preferably 3- to 8-membered or 5- to 8-membered, more preferably 5- or 6-membered, monocyclic non-aromatic ring containing 3 to 12, preferably 3 to 8 or 5 to 8, more preferably 5 or 6 carbon atoms. Preferably, the term "carbocycle" encompasses cycloalkyl and cycloalkenyl groups as defined above.
[0076] The term "heterocycloalkyl" generally includes 3- to 8-membered, particularly 6-membered, monocyclic saturated heterocyclic non-aromatic groups that typically contain 1, 2, or 3 heteroatoms selected from N, O, and S as ring members, and the S atom as a ring member may be present as S, SO, or SO.
[0077] The term "heterocycloalkenyl" generally includes 3- to 8-membered, particularly 6-membered, monocyclic, monounsaturated, heterocyclic non-aromatic groups that typically contain 1, 2, or 3 heteroatoms selected from N, O, and S as ring members, and the S atom as a ring member may be present as S, SO, or SO.
[0078] The term "heterocycle" or "heterocyclyl" generally includes 3- to 12-membered, preferably 3- to 8-membered or 5- to 8-membered, more preferably 5- or 6-membered, and particularly 6-membered monocyclic heterocyclic non-aromatic groups. Heterocyclic non-aromatic groups typically contain 1, 2, 3, 4, or 5, preferably 1, 2, or 3, heteroatoms selected from N, O, and S as ring members, and the S atom as a ring member may be present as S, SO, or SO. Examples of 5- or 6-membered heterocyclic groups are saturated or unsaturated non-aromatic heterocycles, such as oxiranyl, oxetanyl, thietanyl, thietanyl-S-oxide (S-oxothietanyl), thietanyl-S-dioxide (S-dioxothietanyl), pyrrolidinyl, pyrrolinyl, pyrazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, thiolanyl, S-oxothiolanyl, S-dioxothiolanyl, dihydrothienyl, S-oxodihydrothienyl, S-dioxodihydro-thienyl, oxazolidinyl, oxazolinyl, thiazolinyl, nyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, 1,3- and 1,4-dioxanyl, thiopyranyl, S-oxothiopyranyl, S-dioxothiopyranyl, dihydrothiopyranyl, S-oxodihydrothiopyranyl, S-dioxodihydrothiopyranyl, tetrahydrothiopyranyl, S-oxotetrahydrothiopyranyl, S-dioxotetrahydrothiopyranyl, morpholinyl, thiomorpholinyl, S-oxothiomorpholinyl, S-dioxothiomorpholinyl, thiazinyl, etc. Examples of heterocycles which also contain one or two carbonyl groups as ring members also include pyrrolidin-2-onyl, pyrrolidin-2,5-dionyl, imidazolidin-2-onyl, oxazolidin-2-onyl, thiazolidin-2-onyl, etc.
[0079] The term "aryl" includes monocyclic, bicyclic, or tricyclic aromatic groups typically having 6 to 14, preferably 6, 10, or 14, carbon atoms. Exemplary aryl groups include phenyl, naphthyl, and anthracenyl. Phenyl is a preferred aryl group.
[0080] The term "hetaryl" includes monocyclic 5- or 6-membered heteroaromatic groups containing 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring members. Examples of 5- or 6-membered heteroaromatic groups include pyridyl, i.e., 2-, 3-, or 4-pyridyl, pyrimidinyl, i.e., 2-, 4-, or 5-pyrimidinyl, pyrazinyl, pyridazinyl, i.e., 3- or 4-pyridazinyl, thienyl, i.e., 2- or 3-thienyl, furyl, i.e., 2- or 3-furyl, pyrrolyl, i.e., 2- or 3-pyrrolyl, oxazolyl, i.e., 2-, 3-, or 5-oxazolyl, isoxazolyl, i.e., 3-, 4-, or 5-isoxazolyl, thiazolyl, i.e., 2-, 3-, or 5-thiazolyl, isothiazolyl, i.e., 3-, 4-, or 5-isothiazolyl, pyrazolyl, i.e., 1-, 3-, 4-, or 5-pyrazolyl, i.e., 1-, 2-, , 4- or 5-imidazolyl, oxadiazolyl, for example 2- or 5-[1,3,4]oxadiazolyl, 4- or 5-(1,2,3-oxadiazol)yl, 3- or 5-(1,2,4-oxadiazol)yl, 2- or 5-(1,3,4-thiadiazol)yl, thiadiazolyl, for example 2- or 5-(1,3,4-thiadiazol)yl, 4- or 5-(1,2,3-thiadiazol)yl, 3- or 5-(1,2,4-thiadiazol)yl, triazolyl, for example 1H-, 2H- or 3H-1,2,3-triazol-4-yl, 2H-triazol-3-yl, 1H-, 2H- or 4H-1,2,4-triazolyl, and tetrazolyl, i.e. 1H- or 2H-tetrazolyl. The term "hetaryl" also includes bicyclic 8- to 10-membered heteroaromatic groups containing one, two, or three heteroatoms selected from N, O, and S as ring members, wherein the 5- or 6-membered heteroaromatic ring is fused to a phenyl ring or a 5- or 6-membered heteroaromatic group. Examples of 5- or 6-membered heteroaromatic rings fused to a phenyl ring or a 5- or 6-membered heteroaromatic group include benzofuranyl, benzo-thienyl, indolyl, indazolyl, benzimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, quinolinyl, isoquinolinyl, purinyl, 1,8-naphthyridyl, pteridyl, pyrido[3,2-d] These fused hetaryl groups include pyrimidyl or pyridoimidazolyl, etc. These fused hetaryl groups may be attached to the rest of the molecule through any ring atom of the 5- or 6-membered heteroaromatic ring or through a carbon atom of the fused phenyl moiety.
[0081] The terms "heterocyclyloxy", "hetaryloxy", "aryloxy" and "phenoxy" refer to heterocyclyl, hetaryl and aryl, as defined above, and phenyl, attached to the remainder of the molecule via an oxygen atom.
[0082] The terms "heterocyclylsulfonyl," "hetarylsulfonyl," "arylsulfonyl," and "phenylsulfonyl" refer to heterocyclyl, hetaryl, and aryl, respectively, as defined above, and phenyl, which are attached to the remainder of the molecule through the sulfur atom of a sulfonyl group.
[0083] The terms "heterocyclylcarbonyl," "hetarylcarbonyl," "arylcarbonyl," and "phenylcarbonyl" refer to heterocyclyl, hetaryl, and aryl, as defined above, and phenyl, respectively, which are attached to the remainder of the molecule through the carbon atom of a carbonyl group (C=O).
[0084] The terms "heterocyclylalkyl" and "hetarylalkyl" refer to a heterocyclyl or hetaryl as defined above, respectively, which is bound to the rest of the molecule via a C1-C5-alkyl or C1-C4-alkyl group, in particular a methyl group (= heterocyclylmethyl or hetarylmethyl, respectively).
[0085] The terms "arylalkyl" and "phenylalkyl" refer respectively to aryl and phenyl as defined above, which are bonded to the rest of the molecule via a C1-C5-alkyl group or a C1-C4-alkyl group, in particular a methyl group (=arylmethyl or phenylmethyl), examples include benzyl, 1-phenylethyl, 2-phenylethyl, 2-phenoxyethyl, etc.
[0086] The terms "arylalkoxy" and "phenylalkoxy" refer to arylalkyl and phenylalkyl, respectively, as defined above, attached to the remainder of the molecule via an oxygen atom.
[0087] The term "phenylalkoxycarbonyl" refers to a phenylalkoxy as defined above attached to the remainder of the molecule through a carbonyl group (C=O).
[0088] The terms "alkylene," "cycloalkylene," "heterocycloalkylene," "alkenylene," "cycloalkenylene," "heterocycloalkenylene," and "alkynylene" refer to alkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl, and alkynyl, respectively, as defined above, attached to the rest of the molecule through two atoms, preferably two carbon atoms, of the respective group, such that they serve as a linker between two portions of the molecule.
[0089] The term "cyclic moiety" can refer to any cyclic group present in a compound of Formula I and as defined above, such as cycloalkyl, cycloalkenyl, carbocycle, heterocycloalkyl, heterocycloalkenyl, heterocycle, aryl, hetaryl, etc.
[0090] The term "aliphatic" can refer to any non-aromatic hydrocarbon group whose constituent carbon atoms can be straight, branched, or cyclic and / or heteroatoms can be attached to the carbon chain. Furthermore, these aliphatic groups can be substituted with one or more of the same or different substituents.
[0091] The term "carboxy" refers to any carboxyl group attached to the rest of the molecule through the carbon atom of the carboxyl group (-COOH).
[0092] term With regard to the variables, particularly preferred embodiments of the intermediates correspond to those of the compounds of formula I.
[0093] The variables of the compounds of formula I have the following meanings, which meanings, both by themselves and in combination with each other, are preferred embodiments of the compounds of formula I.
[0094] In one embodiment, the active ingredient is a compound of formula I, wherein T is O, S, or NR 1b These compounds correspond to formula I.1, I.2 and I.3, respectively. In one embodiment, the active ingredient is a compound of formula I.1.
[0095] [ka]
[0096] In one embodiment, the present invention relates to a compound of formula I, wherein the five-membered ring is a five-membered ring NR 2 The five-membered ring is attached to the six-membered ring via an amide group at the position next to the Z group. Such compounds correspond to compounds of formula IA. In another embodiment, the invention relates to compounds of formula I, wherein the five-membered ring is attached to the six-membered ring via an amide group at the position next to the Z group of the five-membered ring. 3 The compound is attached to the six-membered ring via an amide group at the position next to the group. Such compounds correspond to compounds of formula IB.
[0097] [ka]
[0098] According to the invention, pesticidal compositions in which the active ingredient is a compound of formula IB are particularly preferred.
[0099] Compounds of formula I are represented by R 1 When is H, it can exist in three tautomeric forms TA, TB, or TC.
[0100] [ka]
[0101] For clarity, only the tautomer TA is depicted throughout this specification, but the description encompasses disclosure of other tautomers as well.
[0102] In a preferred embodiment of the compound of formula I, T is O and the five-membered ring is NR 2 is attached to the rest of the molecule at a position next to the group corresponding to formula I.1.A, or Z 3 The group is attached to the rest of the molecule at the position next to the group and corresponds to formula I.1.B, with compounds of formula I.1.B being preferred.
[0103] [ka]
[0104] In a further embodiment of the compound of formula I, R P1 , R P2 and R P3 is H. These compounds have the formula I * Corresponds to.
[0105] [ka]
[0106] In a preferred embodiment, the active ingredient is a compound of formula IA, and R P1 , R P2 and R P3 is H and formula I * A, or a compound of formula IB and formula I * .B corresponds to formula I * Compounds of formula B are preferred.
[0107] [ka]
[0108] In another preferred embodiment of the compound of formula I, R P1 , R P2 and R P3 is H and T is O. Such compounds have the formula I *Corresponding to the compound .1.
[0109] [ka]
[0110] In a more preferred embodiment, the active ingredient is a compound of formula IA or IB, where R P1 , R P2 and R P3 is H and T is O. These compounds have the formula I * .1.A or I * .1.B, and corresponds to formula I * Compounds of formula .1.B are preferred.
[0111] [ka]
[0112] In one embodiment, the active ingredient is a compound of formula I, preferably formula IA or IB, more preferably formula I * .1.A or I * .1.B, more preferably formula I * .1.B, wherein Z 1 is N and Z 2 is N and Z 3 is CR 5 is.
[0113] In another embodiment, the active ingredient is a compound of formula I, preferably formula IA or IB, more preferably formula I * .1.A or I * .1.B, more preferably formula I * .1.B, wherein Z 1 is CH and Z 2 is CR 4 and Z 3 is N.
[0114] In one embodiment, the active ingredient has formula I * .1.A[where Z 1 is N and R 1is H, C1-C2-alkyl, or C1-C2-alkoxy-C1-C2-alkyl.
[0115] In another embodiment, the active ingredient has formula I * .1.A[where Z 1 and Z 2 is N and Z 3 is CR 5 and R 1 is H, C1-C2-alkyl, or C1-C2-alkoxy-C1-C2-alkyl, and R 5 is H, or C1-C2-alkyl.
[0116] In another embodiment, the active ingredient has formula I * .1.A[where Z 1 and Z 2 is N and Z 3 is CR 5 and R 1 is H, C1-C2-alkyl, or C1-C2-alkoxy-C1-C2-alkyl; R 3 is unsubstituted or halogenated C1-C4-alkyl; R 5 is H, or C1-C2-alkyl.
[0117] In another embodiment, the active ingredient has formula I * .1.A[where Z 1 and Z 3 is N and R 1 is H, C1-C2-alkyl, or C1-C2-alkoxy-C1-C2-alkyl; R 3 is unsubstituted or halogenated C1-C4-alkyl; R 5 is H or C1-C2-alkyl; R 2 is CHR 21 R 22 and; a)R 21 is CH3 and R 22 is CH3; b)R 21 is CF3 and R 22 is CH3; c)R 21 is CH(CH3)2 and R 22 is CH3; d)R 21 is CHFCH3 and R 22 is CH3; e)R 21 is 1-CN-cC3H4, and R 22 is CH3; f)R 21 is 1-C(O)NH2-cC3H4, and R 22 is CH3; or g)R 21 and R 22 are both CH2CH2CF2CH2CH2.
[0118] In one embodiment, the active ingredient has formula I * .1.A[where Z 1 and Z 2 is N and R 1 is CH2CH3; R 3 is CH3; R 5 is H;R 2 is CHR 21 R 22 and; a)R 21 is CH3 and R 22 is CH3; b)R 21 is CF3 and R 22 is CH3; c)R 21 is CH(CH3)2 and R 22 is CH3; d)R 21 is CHFCH3 and R 22 is CH3; e)R 21 is 1-CN-cC3H4, and R 22 is CH3; f)R 21 is 1-C(O)NH2-cC3H4, and R 22 is CH3; or g)R 21 and R 22are both CH2CH2CF2CH2CH2.
[0119] In one embodiment, the active ingredient has formula I * .1.B[where Z 1 is N and R 1 is H, C1-C2-alkyl, or C1-C2-alkoxy-C1-C2-alkyl.
[0120] In another embodiment, the active ingredient has formula I * .1.B[where Z 1 and Z 2 is N and Z 3 is CR 5 and R 1 is H, C1-C2-alkyl, or C1-C2-alkoxy-C1-C2-alkyl, and R 5 is H, or C1-C2-alkyl.
[0121] In another embodiment, the active ingredient has formula I * .1.B[where Z 1 and Z 2 is N and Z 3 is CR 5 and R 1 is H, C1-C2-alkyl, or C1-C2-alkoxy-C1-C2-alkyl; R 3 is unsubstituted or halogenated C1-C4-alkyl; R 5 is H, or C1-C2-alkyl.
[0122] In another embodiment, the active ingredient has formula I * .1.B[where Z 1 and Z 3 is N and R 1 is H, C1-C2-alkyl, or C1-C2-alkoxy-C1-C2-alkyl; R 3 is unsubstituted or halogenated C1-C4-alkyl; R 5 is H or C1-C2-alkyl; R 2 is CHR 21R 22 and; a)R 21 is CH3 and R 22 is CH3; b)R 21 is CF3 and R 22 is CH3; c)R 21 is CH(CH3)2 and R 22 is CH3; d)R 21 is CHFCH3 and R 22 is CH3; e)R 21 is 1-CN-cC3H4, and R 22 is CH3; f)R 21 is 1-C(O)NH2-cC3H4, and R 22 is CH3; or g)R 21 and R 22 are both CH2CH2CF2CH2CH2.
[0123] In one embodiment, the active ingredient has formula I * .1.B[where Z 1 and Z 2 is N and R 1 is CH2CH3; R 3 is CH3; R 5 is H;R 2 is CHR 21 R 22 and; a)R 21 is CH3 and R 22 is CH3; b)R 21 is CF3 and R 22 is CH3; c)R 21 is CH(CH3)2 and R 22 is CH3; d)R 21 is CHFCH3 and R 22 is CH3; e)R 21 is 1-CN-cC3H4, and R22 is CH3; f)R 21 is 1-C(O)NH2-cC3H4, and R 22 is CH3; or g)R 21 and R 22 are both CH2CH2CF2CH2CH2.
[0124] In one embodiment, the active ingredient has formula I * .1.B[where Z 1 and Z 2 is N and Z 3 is CH and R 1 is CH2CH3 and R 3 is CH3 and R 2 is CH(CH3)CH(CH3)2. Thus, such a particularly preferred compound I is 1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, also known as dinpropylidaz.
[0125] In a further embodiment, the active ingredient is a compound of formula I, Z 2 is N and Z 3 is CR 4 and R 4 is any one of groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii). These compounds correspond to compounds of formula I(i), I(ii), I(iiia), I(iiib), I(iiic), I(iiid), I(iva), I(ivb), I(va), I(vb), I(vc), I(via), I(vib), I(vic), I(vid), I(vii) or I(viii).
[0126] In a further embodiment, the active ingredient has formula I, wherein Z 2 is N and R P1 , R P2 and R P3is H and Z 3 is CR 4 and R 4 is any one of groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii). These compounds are compounds of formula I * (i), I * (ii), I * (iiia), I * (iiib), I * (iiic), I * (iiid), I * (iva), I * (ivb), I * (va), I * (vb), I * (vc), I * (via), I * (vib), I * (vic), I * (vid), I * (vii) or I * (viii)
[0127] In a further embodiment, the active ingredient has formula IA, P1 , R P2 and R P3 is H and Z 2 is N and Z 3 is CR 4 and R 4 is any one of groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii). These compounds are compounds of formula I * .A(i), I * .A(ii), I * .A(iiia), I * .A(iiib), I * .A(iiic), I * .A(iiid), I *.A(iva), I * .A(ivb), I * .A(va), I * .A(vb), I * .A(vc), I * .A(via), I * .A(vib), I * .A(vic), I * .A(vid), I * .A(vii) or I * .Corresponding to compound A(viii).
[0128] In a further embodiment, the active ingredient has formula IB, where R P1 , R P2 and R P3 is H and Z 2 is N and Z 3 is CR 4 and R 4 is any one of groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii), which are compounds of I * .B(i), I * .B(ii), I * .B(iiia), I * .B(iiib), I * .B(iiic), I * .B(iiid), I * .B(iva), I * .B(ivb), I * .B(va), I * .B(vb), I * .B(vc), I * .B(via), I * .B(vib), I * .B(vic), I * .B(vid), I * .B(vii) or I * Corresponds to .B(viii).
[0129] I * .A(i), I *.A(ii), I * .A(iiia), I * .A(iiib), I * .A(iiic), I * .A(iiid), I * .A(iva), I * .A(ivb), I * .A(va), I * .A(vb), I * .A(vc), I * .A(via), I * .A(vib), I * .A(vic), I * .A(vid), I * .A(vii) or I * Compounds of formula A(viii) are preferred.
[0130] In a further embodiment, the active ingredient has formula I, wherein R P1 , R P2 and R P3 is H and Z 2 is N and Z 3 is CR 4 and R 4 is any one of groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii), and T is O; * .1(i), I * .1(ii), I * .1(iiia), I * .1(iiib), I * .1(iiic), I * .1(iiid), I * .1(iva), I * .1(ivb), I * .1(va), I * .1(vb), I * .1(vc), I * .1(via), I * .1(vib), I * .1(vic), I * .1(vid), I* .1(vii) or I * .1(viii) corresponds to the compound.
[0131] In a further embodiment, the active ingredient has formula IA, P1 , R P2 and R P3 is H and Z 2 is N and Z 3 is CR 4 and R 4 is any one of groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii), and T is O.
[0132] In a further embodiment, the active ingredient has formula IA, P1 , R P2 and R P3 is H and Z 2 is N and Z 3 is CR 4 , T is O, and R 4 is any one of groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii), which are compounds of formula I * .A.1(i), I * .A.1(ii), I * .A.1(iiia), I * .A.1(iiib), I * .A.1(iiic), I * .A.1(iiid), I * .A.1(iva), I * .A.1(ivb), I * .A.1(va), I * .A.1(vb), I * .A.1(vc), I * .A.1(via), I * .A.1(vib), I *.A.1(vic), I * .A.1(vid), I * .A.1(vii) or I * .A.1(viii) corresponds to the compound.
[0133] In a further embodiment, the active ingredient has formula IB, where R P1 , R P2 and R P3 is H and Z 2 is N and Z 3 is CR 4 and R 4 is any one of groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii), which are compounds of formula I * .B(i), I * .B(ii), I * .B(iiia), I * .B(iiib), I * .B(iiic), I * .B(iiid), I * .B(iva), I * .B(ivb), I * .B(va), I * .B(vb), I * .B(vc), I * .B(via), I * .B(vib), I * .B(vic), I * .B(vid), I * .B(vii) or I * .Corresponding to compound B(viii).
[0134] In a further embodiment, the active ingredient has formula IB, where R P1 , R P2 and R P3 is H and Z 2 is N and Z 3 is CR 4 and Z 2 is CR 4 , T is O, and R4 is any one of groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii), which are compounds of formula I * .B.1(i), I * .B.1(ii), I * .B.1(iiia), I * .B.1(iiib), I * .B.1(iiic), I * .B.1(iiid), I * .B.1(iva), I * .B.1(ivb), I * .B.1(va), I * .B.1(vb), I * .B.1(vc), I * .B.1(via), I * .B.1(vib), I * .B.1(vic), I * .B.1(vid), I * .B.1(vii) or I * .B.1(viii) corresponds to the compound.
[0135] In one preferred embodiment, the active ingredient is a compound of formula I.1.A(iiia).
[0136] [ka]
[0137] In a further preferred embodiment, the active ingredient is a compound of formula I.1.A(iiib), I.1.A(iiic) or I.1.A(iiid).
[0138] [ka]
[0139] In a further preferred embodiment, the active ingredient is a compound of formula I.1.A(iva) or I.1.A(ivb).
[0140] [ka]
[0141] In a further preferred embodiment, the active ingredient is a compound of formula I.1.A(va), I.1.A(vb) or I.1.A(vc).
[0142] [ka]
[0143] In a further preferred embodiment, the active ingredient is a compound of formula I.1.A(via), I.1.A(vib), I.1.A(vic) or I.1.A(vid).
[0144] [ka]
[0145] In a further preferred embodiment, the active ingredient is a compound of formula I.1.A(vii) or I.1.A(viii).
[0146] [ka]
[0147] A preferred group of I.1.A compounds is of formula I.1.A(iiia), where R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(iiia) is a compound.
[0148] [ka]
[0149] Another preferred group of I.1.A compounds has formula I.1.A(iiib), wherein R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(iiib) is a compound.
[0150] [ka]
[0151] Another preferred group of I.1.A compounds has formula I.1.A(iiic), wherein R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(iiic) is a compound.
[0152] [ka]
[0153] Another preferred group of I.1.A compounds has formula I.1.A(iiid), wherein R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(iiid) is a compound.
[0154] [ka]
[0155] Another preferred group of I.1.A compounds has formula I.1.A(iva), wherein R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(iva) is a compound.
[0156] [ka]
[0157] Another preferred group of I.1.A compounds has formula I.1.A(ivb), wherein R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(ivb) is a compound.
[0158] [ka]
[0159] Another preferred group of I.1.A compounds has formula I.1.A(va), where R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(va) is a compound.
[0160] [ka]
[0161] Another preferred group of I.1.A compounds has formula I.1.A(vb), wherein R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(vb) is a compound.
[0162] [ka]
[0163] Another preferred group of I.1.A compounds has formula I.1.A(vc), where R P1 , R P2 and R P3 is H. Such compounds are of formula I *.1.A(vc) is a compound.
[0164] [ka]
[0165] Another preferred group of I.1.A compounds is of formula I.1.A(via), wherein R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(via) compound.
[0166] [ka]
[0167] Another preferred group of I.1.A compounds has formula I.1.A(vib), wherein R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(vib) compound.
[0168] [ka]
[0169] Another preferred group of I.1.A compounds has formula I.1.A(vic), where R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(vic) compound.
[0170] [ka]
[0171] Another preferred group of I.1.A compounds has formula I.1.A(vid), wherein R P1 , R P2and R P3 is H. Such compounds are of formula I * .1.A(vid) compound.
[0172] [ka]
[0173] Another preferred group of I.1.A compounds has formula I.1.A(vii), wherein R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(vii) compound.
[0174] [ka]
[0175] Another preferred group of I.1.A compounds has formula I.1.A(viii), wherein R P1 , R P2 and R P3 is H. Such compounds are of formula I * .1.A(viii) is a compound.
[0176] [ka]
[0177] Typically, in the structures of this application, Z 1 is CH. In another embodiment, Z 1 is N.
[0178] In a further embodiment, the active ingredient has formula I, wherein R 1 is H, C1-C2-alkyl, C3-C5-cycloalkyl or C1-C2-alkoxy-C1-C2-alkyl. 1 is H or C1-C2-alkyl.
[0179] In a further embodiment, the active ingredient has formula I, wherein R 2 and R 3 are each independently H, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C3-C4-cycloalkyl or benzyl. 2 is C1-C2-alkyl, C1-C2-haloalkyl, C3-cycloalkyl or benzyl, more preferably R 2 is C1-C2-alkyl or C1-C2-haloalkyl. Preferably, R 3 is H, halogen, C1-C2-alkyl or C1-C2-haloalkyl, more preferably R 3 is H.
[0180] In one preferred embodiment, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3, CH2CH3, benzyl or halomethyl; R 3 is H, Br or Cl.
[0181] In another preferred embodiment, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H.
[0182] In one particularly preferred embodiment, the active ingredient has formula I, 1 is H, CH3 or CH2CH3.
[0183] In one particularly preferred embodiment, the active ingredient has formula I, 2 is CH3 or halomethyl, more preferably CH3 or fluoromethyl.
[0184] In another particularly preferred embodiment, the active ingredient has formula I, 3 is H].
[0185] R 1 , R 2 and R 3 It is preferred for the above-mentioned preferred compounds, especially I * Compound, I.1 Compound, I * .1 compound, IA compound, I * .A compound, I.1.A compound, I * Also preferred for the .1.A compounds are those in which R 4 is to be understood as preferably any one of options (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii).
[0186] In a further embodiment, the active ingredient is a compound of formula I as defined above, in particular I * Compound, I.1 Compound, I * .1 compound, IA compound, I * .A compound, I.1.A compound, I * .1.A compound, wherein R 4 is one of the options (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii) as illustrated below;
[0187] [ka] In the formula, R 4a , R 4b , R 4c , R 4d , R 4e , R 4f , R 4g , R 4h , R 4i , R 4j , R 4k , R4l , R 4m , R 4n , R 4o , R 4p , R 4q , R 4r , R 4s , R 4t , R 4u , R 4v , A, D, E, G, M, Q, T 1 , V, W, Y and m are as defined above.
[0188] In group (iiia), R 4a is CN, C2-C6-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy-C1-C2-alkyl or C3-C6-cycloalkyl (C atoms may be optionally substituted as described above), R 4b is C1-C4-alkyl, C1-C4-haloalkyl or C3-C6-cycloalkyl (C atoms may be optionally substituted as described above), R 4c is H or CH3 It is particularly preferred that
[0189] Furthermore, in group (iiib), R 4a is H, F, CN, C1-C2-alkyl or halomethyl, A is a cycloalkyl ring, preferably a cyclohexyl, cyclopentyl or cyclobutyl ring, or a tetrahydropyran or tetrahydrofuran ring (which may be substituted as described above). It is preferable.
[0190] Furthermore, in group (iiic), R 4a is CN, C1-C2-alkyl, C1-C2-haloalkyl or cyclopropyl (C atoms may be optionally substituted as described above), R 4bis H, CN, C1-C2-alkyl or C1-C2-haloalkyl (C atoms may be optionally substituted as described above), D is a direct bond or C1-C4-alkylene; E is a non-aromatic heterocyclic group (the heterocyclic ring may be optionally substituted as described above, and the phenyl group may optionally be annealed to the heterocyclic ring); It is preferable.
[0191] Furthermore, in group (iiid), G is □-branched C2-C3-alkylene, preferably CH(CH3) or CH(CH3)CH2; m is 0 or 1; R 4d is C1-C2-haloalkyl or c-C3H5 (C atoms may be halogenated), It is preferable.
[0192] Furthermore, in the group (iva), Q is a direct bond or □-branched or straight chain C1-C8-alkylene, C2-C8-alkenylene or C2-C8-alkynylene (as previously mentioned, the carbon chain may be substituted or unsubstituted), R 4e is H or CH3, or Q and R 4e together form a 4- to 6-membered carbocyclic ring or a 4- to 6-membered heterocyclic ring containing O or S as a heteroatom (as described above, these groups may be substituted), M is O, S, NOCH3 or NSCH3; R M is R 4e or R M and Q together form a 4-6 membered unsaturated non-aromatic N-containing heterocycle (the heterocycle may contain additional heteroatoms O or S, and S may be oxidized), which ring may be unsubstituted or substituted as described above. It is preferable.
[0193] Furthermore, in group (ivb), W is □-branched or linear C1-C8-alkylene, C3-C8-cycloalkylene or C3-C8-heterocycloalkylene, W being substituted as described above; V is O or S; R 4g is H, C1-C4-alkyl or C3-C6-cycloalkyl, R 4f is H, C1-C4-alkyl or C3-C6-cycloalkyl, or R 4g and R 4f together with the carbon atoms to which they are attached form a 3- to 8-membered, saturated or unsaturated, carbocyclic or heterocyclic ring, which heterocyclic ring contains one or more of the same or different heteroatoms N, O or S (S may be oxidized), and which carbocyclic or heterocyclic ring is unsubstituted or substituted as described above. It is preferable.
[0194] Furthermore, in the group (va), R 4his methyl, ethyl, n-butyl, n-pentyl, n-propyl, isopropyl, allyl, 3,3-dimethylallyl, propargyl, cyclohexyl, tetrahydropyranyl, tetrahydrothiopyranyl, 3-oxetanyl, 5-oxa-[3.3.0]-bicycloheptanyl, methoxyethyl, methoxypropyl, ethoxyethyl, ethylthioethyl, methylthioethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 3-chloro-2,2,3,3-tetrafluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl Pyr, 2,2,2-trifluoroethylthio-ethyl, methylcarbonyl-methyl, c-propylcarbonyl-methyl, tert.-butylcarbonyl-methyl, methoxycarbonyl-methyl, ethoxycarbonyl-methyl, hydroxycarbonyl-methyl, carbamoyl-methyl, N-methylcarbamoyl-methyl, Nc-propylcarbamoyl-methyl, N,N-dimethylcarbamoyl-methyl, 2-methoxymino-propyl, cyclopropylmethyl, phenyl, 4-methylphenyl, 2-nitrophenyl, 3-methylthiophenyl, 4-chloro-phenyl, 4-fluoro-phenyl, 4-tert.-butyl-phenyl, 4-methoxy-phenyl, 4-nitrophenyl, 4-dimethylamino-phenyl, 2-fluoro-phenyl, 2-methoxy-phenyl, 2-dimethylaminosulfonyl-phenyl, 2-dimethylaminocarbamoyl-phenyl, 3-nitrophenyl, 3-trifluoromethyl-phenyl, 3-chloro-phenyl, 2,5-dichloro-phenyl, 3,5-dichloro-phenyl, 4-chloro-3-trifluoromethyl-phenyl, 2,4,5-trichloro-phenyl, 2 -pyridyl, 5-(2-chloro)pyridyl, 2-(5-methyl)-pyridyl, 2-(6-methyl)-pyridyl, 2-(3-trifluoromethyl)-pyridyl, 2-pyrimidyl, 2-(4-methyl)-pyrimidyl, 2-(5-methyl)-pyrimidyl, 2-(4-methoxy)-pyrimidyl, 2-(5-fluoro)-pyrimidyl, 2-(4-trifluoromethyl)-pyrimidyl, 2-(5-trifluoromethyl)-pyrimidyl, 2-(4,6-dimethyl)-pyrimidyl, 2-(4,5-dimethyl) -pyrimidyl, 2-(4,6-dimethoxy)-pyrimidyl, -CH2-2-pyrimidyl, -CH2-2-pyrazinyl, -CH2-5-(1-methyl)-imidazolyl, -CH2-3-(1-methyl)-pyrazolyl, -CH2-4-pyridyl, -CH2-2-pyridyl, -CH2-2-(1-methyl)-imidazolyl, -CH2-3-pyridyl, CH2-2-furanyl, -CH2-5-(2-chloro)-pyridyl, benzyl, 3,4-dichloro-benzyl, 2,6-difluoro-benzyl, 2 -fluoro-6-methoxy-benzyl, 2,6-dichloro-benzyl, 2-chloro-6-trifluoromethyl-benzyl, 2-chloro-6-fluoro-benzyl, -CH2-2-(4,6-dimethoxy)-pyrimidyl, 2,6-dimethyl-benzyl, -CH2-1-(3-nitro-5-methyl)-pyrazolyl, 2-(1-methyl)-benzimidazolyl, 2-(5-methyl)-oxdiazolyl, 2-[3-methyl-6-(trifluoromethyl)-imidazo[4.5]-pyridinyl, 3-[4-ethyl-5-(trifluoromethyl)-]-1,2,4-triazolyl, 3-[4-methyl-5-(trifluoromethyl)]-1,2,4-triazolyl-3-[4-methyl-5-(difluoromethyl)]-1,2,4-triazolyl, 2-(5-phenyl)-1,3,4-thiadiazolyl, 2-(1-methyl-5-phenyl)-imidazolyl, 2-(4,5-dimethyl)-oxazolyl, 2-(1-methyl-5-methoxycarbonyl)-imidazolyl, 2-(1-methyl)-imidazolyl, or 1,2-ethanediyl. m is 0, 1 or 2, preferably 0 or 2, particularly preferably 0 It is preferable.
[0195] Furthermore, in the group (vb), R 4iis methyl, ethyl, propyl, isopropyl, cyclopentyl, sec-butyl, allyl, 3-methoxypropyl, 3-cyanopropyl, cyclohexyl, 3,3,3-trifluoropropyl, 3-fluoropropyl, 2-methylsulfanylethyl, 2-[(2,2,2-trifluoroethyl)sulfanyl]ethyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl, tetrahydrofuran-3-yl, tetrahydro-2H-pyran-4-yl, tetrahydro-2H-thiopyran-4-yl, phenyl, 3-methylsulfanylphenyl, 4-chlorophenyl, 4-fluorophenyl, 2,5-difluorophenyl, 2,4-difluorophenyl, 3,5-difluorophenyl, 2-chlorophenyl, 3,4-dichlorophenyl, 3-chlorophenyl, 3-trifluoromethylphenyl, 3-trifluoromethoxyphenyl, 4-fluorobenzyl, pyridin-2-yl, pyrimidin-2-yl-methyl , 5-chloropyridin-3-yl, 6-chloropyridin-3-yl, 5-fluoropyridin-3-yl, 6-methoxypyridin-3-yl, 5-trifluoromethyl-pyridin-3-yl, pyridin-3-yl-methyl, 6-fluoropyridin-3-yl, 6-methylpyridin-3-yl, 6-[6-chloropyridin-3-yloxy]pyridin-3-yl, 6-[6-fluoropyridin-3-yloxy]pyridin-3-yl, 6-{6-[6-fluoropyridin-3-yloxy]pyridin-3-yl phenyl-3-yloxy]pyridin-3-yl}oxypyridin-3-yl, 4-methylpyridin-3-yl, 5-methylpyridin-3-yl, pyridin-3-yl, 6-trifluoromethylpyridin-3-yl, 6-chloro-5-methylpyridin-3-yl, 6-cyanopyridin-3-yl, 6-chloro-4-methylpyridin-3-yl, 5-methoxypyridin-3-yl, 6-bromopyridin-3-yl, 5-cyanopyridin-3-yl, quinolin-3-yl, 5,6-dimethoxypyridin-3-yl, 4-chloropyridin-3-yl, 2-chloropyridin-3-yl, 5-bromopyridin-3-yl, 5-chloro-2-methoxypyridin-3-yl, 2-fluoro-6-methylpyridin-3-yl, 3-cyanophenyl, 3-ethoxyphenyl, 3-acetamidophenyl, 3-ethylphenyl, 3-methoxyphenyl, 3-propylphenyl, 2-fluoro-3-trifluoromethylphenyl, 3-methylphenyl, 3-methylsulfonylphenyl, 3-phenoxyphenyl, 3-butylsulfanylphenyl, 4-fluoro-3-trifluoromethylphenyl, 3-methoxycarbonimidoylphenyl, 3-chloro-4-methylphenyl, 3-fluoro-5-trifluoromethylphenyl, 3-chloro-5-trifluoromethylphenyl, 3-chloro-5-methoxyphenyl, or 3-chloro-4-fluorophenyl, 3-trifluoromethylphenyl, It is preferable.
[0196] Furthermore, in the group (vc), R 4j and R 4k together with the nitrogen atom to which they are attached form a 5- or 6-membered heterocyclic ring, which contains a nitrogen atom as a heteroatom (and may further contain one or two of the same or different heteroatoms N or O), and which ring is substituted as described above. It is preferable.
[0197] Furthermore, in the via group, R 4l is H, methyl, ethyl, isopropyl, 1-cyano-1-methylethyl or cyclopropyl, T 1 O, N-OR 1C , N-NR 2C R 3C , or the aforementioned formula T 11 and the substituents are defined as above. It is preferable.
[0198] Furthermore, in group (vib), R4m is methyl or ethyl It is preferable.
[0199] Furthermore, in the group (vic), R 4n is H, methyl, ethyl, methylsulfonyl or cyclopropylsulfonyl, R 4o is H, methyl, ethyl, isopropyl, isobutyl, tert.butyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-methoxyethyl, cyanomethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, cyclopropyl, 1-cyanocyclopropyl, cyclopentyl, cyclopropylmethyl, methoxy, ethoxy, phenyl, pyridin-3-yl, phenylmethyl or 1-phenyl-2-hydroxyethyl, or R 4n and R 4o are both (CH2)5, (CH2)4, (CH2)3 or (CH2)2O(CH2)2, Y is O or S It is preferable.
[0200] Furthermore, in the group (vid), R 4p is H, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which are unsubstituted or substituted as described above, or C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which are unsubstituted or substituted as described above, R 4qis H, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which are unsubstituted or substituted as described above, or C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which are unsubstituted or substituted as described above, R 4r is H, C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which are unsubstituted or substituted as described above, or C3-C8-cycloalkyl or C3-C8-cycloalkyl-C1-C4-alkyl, which are unsubstituted or substituted as described above, or aryl, hetaryl, arylalkyl or hetarylalkyl, which are unsubstituted or substituted as described above. It is preferable.
[0201] Furthermore, in group (vii), R 4sare 3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 3-(methylsulfanyl)phenyl, pyrimidin-2-yl, 3-[(2,2,2-trifluoroethyl)sulfinyl]phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1-methyl-1H-pyrrol-2-yl, 3-furyl, 2,5-dimethyl-3-thienyl, 3-[(trifluoromethyl)sulfanyl]phenyl, 3-[(cyclopropylmethyl)sulfanyl]phenyl, 3-(methoxymethyl)phenyl, 3-[(tetrahydro-2H-pyran-4-yloxy)methyl]phenyl, 3-(dimethylsulfamoyl)phenyl, 3-(methylsulfonyl)phenyl , 4-methyl-3-(methylsulfanyl)phenyl, 1-(2-cyanophenyl)-1H-pyrazol-4-yl, 1-(4-fluorophenyl)-1H-pyrazol-4-yl, 1-phenyl-1H-pyrazol-4-yl, 1-naphthyl, 5-(methoxycarbonyl)-1-naphthyl, 4-fluoro-2-(methoxycarbonyl)phenyl, 4-fluoro-1-naphthyl, 4-chloro-3-(ethoxycarbonyl)phenyl, 2-(methoxycarbonyl)phenyl carbonyl)phenyl, pyridin-4-yl, 6-(ethoxycarbonyl)pyridin-2-yl, 3-(ethoxycarbonyl)phenyl, 2-naphthyl, 4-methoxy-3-(methoxycarbonyl)phenyl, 4-chloro-2-(methoxycarbonyl)phenyl, 3-thienyl, 3-(2-ethoxy-2-oxoethoxy)-4-methylphenyl, 3-(2-ethoxy-2-oxoethoxy)phenyl, 3-(2-ethoxy-2-oxoethoxy)-4,5-difluorophenyl, 3-(2-ethoxy-2-oxoethoxy)-4-fluorophenyl, 3-(ethoxycarbonyl)-4-fluorophenyl, (3-{[(cyclopropylcarbonyl)oxy]methyl}phenyl, 3-{[(cyclopropylcarbonyl)oxy]methyl}-4-fluorophenyl, pyridin-2-yl, 3-(difluoromethyl)phenyl, 3-[(trifluoromethyl)sulfinyl]phenyl, 4-fluoro-3-(trifluoromethyl)phenyl, 3-chloro-5-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, 3-fluoro-5-(trifluoromethyl)phenyl, 4-cyano-3-(trifluoromethyl)phenyl, 3-(2,2,2-trifluoroethyl)phenyl, 3-(pentafluoroethyl)phenyl, 3-cyanophenyl, 4-chloro-3-cyanophenyl, 3-cyano-5-fluorophenyl, 3-cyano-5-(trifluoromethyl) Phenyl, 5-cyano-2-methoxyphenyl, 3-cyano-4-fluorophenyl, 5-cyanopyridin-3-yl, 5-cyano-6-(dimethylamine)pyridin-3-yl, 5-cyano-6-(morpholin-4-yl)pyridin-3-yl, 5-cyano-6-ethoxypyridin-3-yl, 5-cyano-6-methoxypyridin-3-yl, 3-chloro-5-cyanophenyl, 1-benzofuran-2-yl, 3-phenyl-1,2-oxazol-5-yl, 3-(ethoxycarbonyl)pyridin-3-yl (bornyl)-1,2-oxazol-5-yl, 1-isopropyl-1H-1,2,3-triazol-4-yl, 1-methyl-1H-1,2,3-triazol-4-yl, 5-cyano-6-methoxypyridin-3-yl, 6-methoxypyridin-2-yl, 2,3-dihydro-1-benzofuran-7-yl, 1-benzofuran-7-yl, 2,6-dimethoxypyridin-3-yl, 2-methoxyphenyl, 1,3-benzodioxol-4-yl, 2,4-dimethoxyphenyl, 2,5-Dimethoxyphenyl, 6-(trifluoromethyl)pyridin-2-yl, 5-chloro-2-methoxypyridin-3-yl, 2-methoxypyridin-3-yl, 6-ethoxypyridin-3-yl, 5-chloro-6-methoxypyridin-3-yl, 2-(methylsulfanyl)pyridin-3-yl, 2-ethoxypyridin-3-yl, 5,6-dimethoxypyridin-3-yl, 2-methoxypyridin-4-yl, 6-methoxy-5-(trifluoromethyl)pyridin-3-yl, 6-methoxy- 5-nitropyridin-3-yl, 2,6-dimethoxypyridin-4-yl, 2-(methylsulfanyl)phenyl, 2-methoxy-6-(trifluoromethyl)-pyridin-4-yl, 3-cyano-5-methoxyphenyl, 5-fluoro-2-methoxypyridin-3-yl, 6-isopropoxypyridin-3-yl, 6-methoxypyridin-3-yl, 2-(2-amino-2-oxoethoxy)phenyl, 3-cyano-4-isopropoxyphenyl, or 3-chloropyridin-2-yl, It is preferable.
[0202] Furthermore, in group (viii), R 4t is H, methyl, trifluoromethyl, trichloromethyl, isopropyl, isobutyl, isopentyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl or benzyl; R 4u is H or methyl, or R 4t and R 4u are both vinyl, prop-1-en-2-yl, (1E)-prop-1-en-1-yl, (1Z)-prop-1-en-1-yl or cyclopropyl; R 4v is H, S(O) m R 1E , OR 2E or N(R 3E )(R 4E ) and R 4t and / or R 4uis H or C1-C8-alkyl, R 4v is S(O) m R 1E , OR 2E or N(R 3E )(R 4E ) and R 1E is methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopropylmethyl, 2,2-dimethylpropyl, 2-methoxy-2-oxoethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl or 2-pyrimidyl, R 2E is H, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3-chlorophenyl or 4-chlorophenyl, R 3E and R 4E together with the nitrogen atom to which they are attached form a 5-membered heterocyclic ring, the heterocyclyl group of which contains 1 or 2 N atoms (the ring group may contain one CO group), and the C atoms are substituted with trifluoromethyl, methyl or cyclopropyl. It is preferable.
[0203] Compounds of formula I as defined above, in particular I * Compound, I.1 Compound, I * .1 compound, IA compound, I * .A compound, I.1.A compound, I * .1.A related to the compound, R 4 With respect to the above preferences for groups (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vic), (vid), (vii) or (viii), R 1 , R 2 and R 3 It is further preferred that R corresponds to the preferred options provided above. For example, R 4 With regard to the preferences given above for groups, R 1is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3, CH2CH3, benzyl or halomethyl; R 3 is H, Br or Cl; or R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H is preferred.
[0204] In view of the above, the following compounds are particularly preferred as active ingredients according to the present invention.
[0205] A preferred embodiment is a compound of formula I as an active ingredient. * .A(iiia) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4a , R 4b and R 4c At least one of is C3-C4-cycloalkenyl, C3-C4-halocycloalkenyl, OR a or SR a and R a is C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl, T is O, S or NR 1b is] The present invention relates to the compound
[0206] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(iiib) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R2 is CH3 or halomethyl, R 3 is H, R 4a is as defined above, A is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group; T is O, S or NR 1b is] The present invention relates to the compound
[0207] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(iiic) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4a and R 4b is as defined above, E is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group; T is O, S or NR 1b is] The present invention relates to the compound
[0208] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(iiid)[wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4d is C1-C2-haloalkyl or c-C3H5 (C atoms may be halogenated), G is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group; T is O, S or NR 1b is] The present invention relates to the compound
[0209] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(iva)[wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4e is H or CH3, Q is a direct bond or □-branched or straight-chain C1-C8-alkylene, C2-C8-alkenylene or C2-C8-alkynylene, the carbon chain of which may be substituted or unsubstituted as previously described; M is O, S, NOCH3 or NSCH3; T is O, S or NR 1b is] The present invention relates to the compound
[0210] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(ivb)[where, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4f is H, C1-C4-alkyl or C3-C6-cycloalkyl, R 4g is H, C1-C4-alkyl or C3-C6-cycloalkyl, V is O or S; W is □-branched or linear C1-C8-alkylene, C3-C8-cycloalkylene or C3-C8-heterocycloalkylene, W being substituted as described above; T is O, S or NR 1b is] The present invention relates to the compound
[0211] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(va)[wherein, R 1 is H or CH3, preferably CH3, R 2 is CH3, R 3 is H, chlorine or bromine, preferably H, R 4his methyl, ethyl, n-butyl, n-pentyl, n-propyl, isopropyl, allyl, 3,3-dimethylallyl, propargyl, cyclohexyl, tetrahydropyranyl, tetrahydrothiopyranyl, 3-oxetanyl, 5-oxa-[3.3.0]-bicycloheptanyl, methoxyethyl, methoxypropyl, ethoxyethyl, ethylthioethyl, methylthioethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 3-chloro-2,2,3,3-tetrafluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl Pyr, 2,2,2-trifluoroethylthio-ethyl, methylcarbonyl-methyl, c-propylcarbonyl-methyl, tert.-butylcarbonyl-methyl, methoxycarbonyl-methyl, ethoxycarbonyl-methyl, hydroxycarbonyl-methyl, carbamoyl-methyl, N-methylcarbamoyl-methyl, Nc-propylcarbamoyl-methyl, N,N-dimethylcarbamoyl-methyl, 2-methoxymino-propyl, cyclopropylmethyl, phenyl, 4-methylphenyl, 2-nitrophenyl, 3-methylthiophenyl, 4-chloro-phenyl, 4-fluoro-phenyl, 4-tert.-butyl-phenyl, 4-methoxy-phenyl, 4-nitrophenyl, 4-dimethylamino-phenyl, 2-fluoro-phenyl, 2-methoxy-phenyl, 2-dimethylaminosulfonyl-phenyl, 2-dimethylaminocarbamoyl-phenyl, 3-nitrophenyl, 3-trifluoromethyl-phenyl, 3-chloro-phenyl, 2,5-dichloro-phenyl, 3,5-dichloro-phenyl, 4-chloro-3-trifluoromethyl-phenyl, 2,4,5-trichloro-phenyl 2-pyridyl, 5-(2-chloro)pyridyl, 2-(5-methyl)-pyridyl, 2-(6-methyl)-pyridyl, 2-(3-trifluoromethyl)-pyridyl, 2-pyrimidyl, 2-(4-methyl)-pyrimidyl, 2-(5-methyl)-pyrimidyl, 2-(4-methoxy)-pyrimidyl, 2-(5-fluoro)-pyrimidyl, 2-(4-trifluoromethyl)-pyrimidyl, 2-(5-trifluoromethyl)-pyrimidyl, 2-(4,6-dimethyl)-pyrimidyl, 2-(4,5 -dimethyl)-pyrimidyl, 2-(4,6-dimethoxy)-pyrimidyl, -CH2-2-pyrimidyl, -CH2-2-pyrazinyl, -CH2-5-(1-methyl)-imidazolyl, -CH2-3-(1-methyl)-pyrazolyl, -CH2-4-pyridyl, -CH2-2-pyridyl, -CH2-2-(1-methyl)-imidazolyl, -CH2-3-pyridyl, CH2-2-furanyl, -CH2-5-(2-chloro)-pyridyl, benzyl, 3,4-dichloro-benzyl, 2,6-difuranyl 2-Fluoro-6-methoxy-benzyl, 2,6-dichloro-benzyl, 2-chloro-6-tolylfluoromethyl-benzyl, 2-chloro-6-fluoro-benzyl, -CH2-2-(4,6-dimethoxy)-pyrimidyl, 2,6-dimethyl-benzyl, -CH2-1-(3-nitro-5-methyl)-pyrazolyl, 2-(1-methyl)-benzimidazolyl, 2-(5-methyl)-oxdiazolyl, 2-[3-methyl-6-(trifluoromethyl)-imidazo[4.5]-pyridinyl, 3-[4-ethyl-5-(trifluoromethyl)-]-1,2,4-triazolyl, 3-[4-methyl-5-(trifluoromethyl)]-1,2,4-triazolyl, 3-[4-methyl-5-(difluoromethyl)]-1,2,4-triazolyl, 2-(5-phenyl)-1,3,4-thiadiazolyl, 2-(1-methyl-5-phenyl)-imidazolyl, 2-(4,5-dimethyl)-oxazolyl, 2-(1-methyl-5-methoxycarbonyl)-imidazolyl, 2-(1-methyl)-imidazolyl, or 1,2-ethanediyl. m is 0 or 2, preferably 0; T is O, S or NR 1b is] The present invention relates to the compound
[0212] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(vb)[wherein, R 1 is H, methyl, ethyl or cyclopropyl, R 2 is CH3, R 3 is H, chlorine or bromine, preferably H, R 4iis methyl, ethyl, propyl, isopropyl, cyclopentyl, sec-butyl, allyl, 3-methoxypropyl, 3-cyanopropyl, cyclohexyl, 3,3,3-trifluoropropyl, 3-fluoropropyl, 2-methylsulfanylethyl, 2-[(2,2,2-trifluoroethyl)sulfanyl]ethyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl, tetrahydrofuran-3-yl, tetrahydro-2H-pyran-4-yl, tetrahydro-2H-thiopyran-4-yl, phenyl, 3-methylsulfanylphenyl, 4-chlorophenyl, 4-fluorophenyl, 2,5-difluorophenyl, 2,4-difluorophenyl, 3,5-difluorophenyl, 2-chlorophenyl, 3,4-dichlorophenyl, 3-chlorophenyl, 3-trifluoromethylphenyl, 3-trifluoromethoxyphenyl, 4-fluorobenzyl, pyridin-2-yl, pyrimidin-2-ylmethyl , 5-chloropyridin-3-yl, 6-chloropyridin-3-yl, 5-fluoropyridin-3-yl, 6-methoxypyridin-3-yl, 5-trifluoromethyl-pyridin-3-yl, pyridin-3-ylmethyl, 6-fluoropyridin-3-yl, 6-methylpyridin-3-yl, 6-[6-chloropyridin-3-yloxy]pyridin-3-yl, 6-[6-fluoropyridin-3-yloxy]pyridin-3-yl, 6-{6-[6-fluoropyridin -3-yloxy]pyridin-3-yl}oxypyridin-3-yl, 4-methylpyridin-3-yl, 5-methylpyridin-3-yl, pyridin-3-yl, 6-trifluoromethylpyridin-3-yl, 6-chloro-5-methylpyridin-3-yl, 6-cyanopyridin-3-yl, 6-chloro-4-methylpyridin-3-yl, 5-methoxypyridin-3-yl, 6-bromopyridin-3-yl, 5-cyanopyridin-3-yl, quinolin-3-yl, 5,6-dimethoxypyridin-3-yl, 4-chloropyridin-3-yl, 2-chloropyridin-3-yl, 5-bromopyridin-3-yl, 5-chloro-2-methoxypyridin-3-yl, 2-fluoro-6-methylpyridin-3-yl, 3-cyanophenyl, 3-ethoxyphenyl, 3-acetamidophenyl, 3-ethylphenyl, 3-methoxyphenyl, 3-propylphenyl, 2-fluoro-3-trifluoromethylphenyl, 3-methylphenyl, 3-methylsulfonylphenyl, 3-phenoxyphenyl, 3-butylsulfanylphenyl, 4-fluoro-3-trifluoromethylphenyl, 3-methoxycarbonimidoylphenyl, 3-chloro-4-methylphenyl, 3-fluoro-5-trifluoromethylphenyl, 3-chloro-5-trifluoromethylphenyl, 3-chloro-5-methoxyphenyl, or 3-chloro-4-fluorophenyl or 3-trifluoromethylphenyl, T is O, S or NR 1b is] The present invention relates to the compound
[0213] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(vc)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4j and R 4k together with the nitrogen atom to which they are attached form a 5- or 6-membered heterocycle, which heterocycle contains a nitrogen atom as the heteroatom; T is O, S or NR 1b is] The present invention relates to the compound
[0214] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(via)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2is CH3, R 3 is H, R 4l is H, methyl, ethyl, isopropyl, 1-cyano-1-methylethyl or cyclopropyl, T 1 is as defined above, T is O, S or NR 1b is] The present invention relates to the compound
[0215] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(vib)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4m is methyl or ethyl, T is O, S or NR 1b is] The present invention relates to the compound
[0216] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(vic)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4n is H, methyl, ethyl, methylsulfonyl or cyclopropylsulfonyl, R 4ois H, methyl, ethyl, isopropyl, isobutyl, tert.butyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-methoxyethyl, cyanomethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, cyclopropyl, 1-cyanocyclopropyl, cyclopentyl, cyclopropylmethyl, methoxy, ethoxy, phenyl, pyridin-3-yl, phenylmethyl or 1-phenyl-2-hydroxyethyl, or R 4n and R 4o are both (CH2)5, (CH2)4, (CH2)3 or (CH2)2O(CH2)2, Y is O or S; T is O, S or NR 1b is] The present invention relates to the compound
[0217] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(vid)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4p is H, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which are unsubstituted or substituted as described above, or C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which are unsubstituted or substituted as described above, R 4qis H, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which are unsubstituted or substituted as described above, or C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which are unsubstituted or substituted as described above, R 4r is H, C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which may be unsubstituted or substituted as described above, or C3-C8-cycloalkyl or C3-C8-cycloalkyl-C1-C4-alkyl, which may be unsubstituted or substituted as described above, or aryl, hetaryl, arylalkyl or hetarylalkyl, which may be unsubstituted or substituted as described above, Y is O or S; T is O, S or NR 1b is] The present invention relates to the compound
[0218] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(vii) [wherein, R 1 is H, methyl, ethyl, preferably methyl and ethyl, R 2 is CH3, R 3 is H, chlorine, bromine, preferably H, R 4sare 3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 3-(methylsulfanyl)phenyl, pyrimidin-2-yl, 3-[(2,2,2-trifluoroethyl)sulfinyl]phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1-methyl-1H-pyrrol-2-yl, 3-furyl, 2,5-dimethyl-3-thienyl, 3-[(trifluoromethyl)sulfanyl]phenyl, 3-[(cyclopropylmethyl)sulfanyl]phenyl, 3-(methoxymethyl)phenyl, 3-[(tetrahydro-2H-pyran-4-yloxy)methyl]phenyl, 3-(dimethylsulfamoyl)phenyl, 3-(methylsulfonyl)phenyl , 4-methyl-3-(methylsulfanyl)phenyl, 1-(2-cyanophenyl)-1H-pyrazol-4-yl, 1-(4-fluorophenyl)-1H-pyrazol-4-yl, 1-phenyl-1H-pyrazol-4-yl, 1-naphthyl, 5-(methoxycarbonyl)-1-naphthyl, 4-fluoro-2-(methoxycarbonyl)phenyl, 4-fluoro-1-naphthyl, 4-chloro-3-(ethoxycarbonyl)phenyl, 2-(methoxycarbonyl)phenyl carbonyl)phenyl, pyridin-4-yl, 6-(ethoxycarbonyl)pyridin-2-yl, 3-(ethoxycarbonyl)phenyl, 2-naphthyl, 4-methoxy-3-(methoxycarbonyl)phenyl, 4-chloro-2-(methoxycarbonyl)phenyl, 3-thienyl, 3-(2-ethoxy-2-oxoethoxy)-4-methylphenyl, 3-(2-ethoxy-2-oxoethoxy)phenyl, 3-(2-ethoxy-2-oxoethoxy)4,5-difluorophenyl, 3-(2-ethoxy-2-oxoethoxy)-4-fluorophenyl, 3-(ethoxycarbonyl)-4-fluorophenyl, (3-{[(cyclopropylcarbonyl)oxy]methyl}phenyl, 3-{[(cyclopropylcarbonyl)oxy]methyl}-4-fluorophenyl, pyridin-2-yl, 3-(difluoromethyl)phenyl, 3-[(trifluoromethyl)sulfinyl]phenyl, 4-fluoro-3-(trifluoromethyl)phenyl, 3-chloro-5-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, 3-fluoro-5-(trifluoromethyl)phenyl, 4-cyano-3-(trifluoromethyl)phenyl, 3-(2,2,2-trifluoroethyl)phenyl, 3-(pentafluoroethyl)phenyl, 3-cyanophenyl, 4-chloro-3-cyanophenyl, 3-cyano-5-fluorophenyl, 3-cyano-5-(trifluoromethyl) Phenyl, 5-cyano-2-methoxyphenyl, 3-cyano-4-fluorophenyl, 5-cyanopyridin-3-yl, 5-cyano-6-(dimethylamine)pyridin-3-yl, 5-cyano-6-(morpholin-4-yl)pyridin-3-yl, 5-cyano-6-ethoxypyridin-3-yl, 5-cyano-6-methoxypyridin-3-yl, 3-chloro-5-cyanophenyl, 1-benzofuran-2-yl, 3-phenyl-1,2-oxazol-5-yl, 3-(ethoxycarbonyl)pyridin-3-yl (bornyl)-1,2-oxazol-5-yl, 1-isopropyl-1H-1,2,3-triazol-4-yl, 1-methyl-1H-1,2,3-triazol-4-yl, 5-cyano-6-methoxypyridin-3-yl, 6-methoxypyridin-2-yl, 2,3-dihydro-1-benzofuran-7-yl, 1-benzofuran-7-yl, 2,6-dimethoxypyridin-3-yl, 2-methoxyphenyl, 1,3-benzodioxol-4-yl, 2,4-dimethoxyphenyl, 2,5-Dimethoxyphenyl, 6-(trifluoromethyl)pyridin-2-yl, 5-chloro-2-methoxypyridin-3-yl, 2-methoxypyridin-3-yl, 6-ethoxypyridin-3-yl, 5-chloro-6-methoxypyridin-3-yl, 2-(methylsulfanyl)pyridin-3-yl, 2-ethoxypyridin-3-yl, 5,6-dimethoxypyridin-3-yl, 2-methoxypyridin-4-yl, 6-methoxy-5-(trifluoromethyl)pyridin-3-yl, 6-methoxy- 5-nitropyridin-3-yl, 2,6-dimethoxypyridin-4-yl, 2-(methylsulfanyl)phenyl, 2-methoxy-6-(trifluoromethyl)-pyridin-4-yl, 3-cyano-5-methoxyphenyl, 5-fluoro-2-methoxypyridin-3-yl, 6-isopropoxypyridin-3-yl, 6-methoxypyridin-3-yl, 2-(2-amino-2-oxoethoxy)phenyl, 3-cyano-4-isopropoxyphenyl, or 3-chloropyridin-2-yl, T is O, S or NR 1b is] The present invention relates to the compound
[0219] Another preferred embodiment is a compound of formula I as an active ingredient. * .A(viii) [wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4t is H, methyl, trifluoromethyl, trichloromethyl, isopropyl, isobutyl, isopentyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl or benzyl; R 4u is H or methyl, or R 4t and R 4uare both vinyl, prop-1-en-2-yl, (1E)-prop-1-en-1-yl, (1Z)-prop-1-en-1-yl or cyclopropyl; R 4v is H, S(O) m R 1E , OR 2E or N(R 3E )(R 4E ) and R 4t and / or R 4u is H or C1-C8-alkyl, R 4v is S(O) m R 1E , OR 2E or N(R 3E )(R 4E ) and R 1E is methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopropylmethyl, 2,2-dimethylpropyl, 2-methoxy-2-oxoethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl or 2-pyrimidyl, R 2E is H, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3-chlorophenyl or 4-chlorophenyl, R 3E and R 4E together with the nitrogen atom to which they are attached form a 5-membered heterocyclic ring, the heterocyclyl group of which contains 1 or 2 N atoms (the ring group may contain one CO group) and the C atoms of which are substituted by trifluoromethyl, methyl or cyclopropyl, T is O, S or NR 1b is] The present invention relates to the compound
[0220] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(iiia) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4a , R 4b and R 4c At least one of is C3-C4-cycloalkenyl, C3-C4-halocycloalkenyl, OR a or SR a and R a is C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl, T is O, S or NR 1b is] This refers to the compound.
[0221] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(iiib) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4a is as defined above, A is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group; T is O, S or NR 1b is] The present invention relates to the compound
[0222] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(iiic) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4a and R 4b is as defined above, E is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group; T is O, S or NR 1b is] The present invention relates to the compound
[0223] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(iiid)[wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4d is C1-C2-haloalkyl or c-C3H5 (C atoms may be halogenated), G is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group; T is O, S or NR 1b is] The present invention relates to the compound
[0224] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(iva)[wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4e is H or CH3, Q is a direct bond or □-branched or straight-chain C1-C8-alkylene, C2-C8-alkenylene or C2-C8-alkynylene, the carbon chain of which may be substituted or unsubstituted as previously described; M is O, S, NOCH3 or NSCH3; T is O, S or NR 1b is] The present invention relates to the compound
[0225] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(ivb)[wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4f is H, C1-C4-alkyl or C3-C6-cycloalkyl, R 4g is H, C1-C4-alkyl or C3-C6-cycloalkyl, V is O or S; W is □-branched or linear C1-C8-alkylene, C3-C8-cycloalkylene or C3-C8-heterocycloalkylene, W being substituted as described above; T is O, S or NR 1b is] The present invention relates to the compound
[0226] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(va)[in the formula, R 1 is H or CH3, preferably CH3, R 2 is CH3, R 3 is H, chlorine or bromine, preferably H, R 4his methyl, ethyl, n-butyl, n-pentyl, n-propyl, isopropyl, allyl, 3,3-dimethylallyl, propargyl, cyclohexyl, tetrahydropyranyl, tetrahydrothiopyranyl, 3-oxetanyl, 5-oxa-[3.3.0]-bicycloheptanyl, methoxyethyl, methoxypropyl, ethoxyethyl, ethylthioethyl, methylthioethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 3-chloro-2,2,3,3-tetrafluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl Pyr, 2,2,2-trifluoroethylthio-ethyl, methylcarbonyl-methyl, c-propylcarbonyl-methyl, tert.-butylcarbonyl-methyl, methoxycarbonyl-methyl, ethoxycarbonyl-methyl, hydroxycarbonyl-methyl, carbamoyl-methyl, N-methylcarbamoyl-methyl, Nc-propylcarbamoyl-methyl, N,N-dimethylcarbamoyl-methyl, 2-methoxymino-propyl, cyclopropylmethyl, phenyl, 4-methylphenyl, 2-nitrophenyl, 3-methylthiophenyl, 4-chloro-phenyl, 4-fluoro-phenyl, 4-tert.-butyl-phenyl, 4-methoxy-phenyl, 4-nitrophenyl, 4-dimethylamino-phenyl, 2-fluoro-phenyl, 2-methoxy-phenyl, 2-dimethylaminosulfonyl-phenyl, 2-dimethylaminocarbamoyl-phenyl, 3-nitrophenyl, 3-trifluoromethyl-phenyl, 3-chloro-phenyl, 2,5-dichloro-phenyl, 3,5-dichloro-phenyl, 4-chloro-3-trifluoromethyl-phenyl, 2,4,5-trichloro-phenyl 2-pyridyl, 5-(2-chloro)pyridyl, 2-(5-methyl)-pyridyl, 2-(6-methyl)-pyridyl, 2-(3-trifluoromethyl)-pyridyl, 2-pyrimidyl, 2-(4-methyl)-pyrimidyl, 2-(5-methyl)-pyrimidyl, 2-(4-methoxy)-pyrimidyl, 2-(5-fluoro)-pyrimidyl, 2-(4-trifluoromethyl)-pyrimidyl, 2-(5-trifluoromethyl)-pyrimidyl, 2-(4,6-dimethyl)-pyrimidyl, 2-(4,5 -dimethyl)-pyrimidyl, 2-(4,6-dimethoxy)-pyrimidyl, -CH2-2-pyrimidyl, -CH2-2-pyrazinyl, -CH2-5-(1-methyl)-imidazolyl, -CH2-3-(1-methyl)-pyrazolyl, -CH2-4-pyridyl, -CH2-2-pyridyl, -CH2-2-(1-methyl)-imidazolyl, -CH2-3-pyridyl, CH2-2-furanyl, -CH2-5-(2-chloro)-pyridyl, benzyl, 3,4-dichloro-benzyl, 2,6-difuranyl 2-Fluoro-6-methoxy-benzyl, 2,6-dichloro-benzyl, 2-chloro-6-tolylfluoromethyl-benzyl, 2-chloro-6-fluoro-benzyl, -CH2-2-(4,6-dimethoxy)-pyrimidyl, 2,6-dimethyl-benzyl, -CH2-1-(3-nitro-5-methyl)-pyrazolyl, 2-(1-methyl)-benzimidazolyl, 2-(5-methyl)-oxdiazolyl, 2-[3-methyl-6-(trifluoromethyl)-imidazo[4.5]-pyridinyl, 3-[4-ethyl-5-(trifluoromethyl)-]-1,2,4-triazolyl, 3-[4-methyl-5-(trifluoromethyl)]-1,2,4-triazolyl, 3-[4-methyl-5-(difluoromethyl)]-1,2,4-triazolyl, 2-(5-phenyl)-1,3,4-thiadiazolyl, 2-(1-methyl-5-phenyl)-imidazolyl, 2-(4,5-dimethyl)-oxazolyl, 2-(1-methyl-5-methoxycarbonyl)-imidazolyl, 2-(1-methyl)-imidazolyl, or 1,2-ethanediyl. m is 0 or 2, preferably 0; T is O, S or NR 1b is] The present invention relates to the compound
[0227] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(vb)[wherein, R 1 is H, methyl, ethyl or cyclopropyl, R 2 is CH3, R 3 is H, chlorine or bromine, preferably H, R 4iis methyl, ethyl, propyl, isopropyl, cyclopentyl, sec-butyl, allyl, 3-methoxypropyl, 3-cyanopropyl, cyclohexyl, 3,3,3-trifluoropropyl, 3-fluoropropyl, 2-methylsulfanylethyl, 2-[(2,2,2-trifluoroethyl)sulfanyl]ethyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl, tetrahydrofuran-3-yl, tetrahydro-2H-pyran-4-yl, tetrahydro-2H-thiopyran-4-yl, phenyl, 3-methylsulfanylphenyl, 4-chlorophenyl, 4-fluorophenyl, 2,5-difluorophenyl, 2,4-difluorophenyl, 3,5-difluorophenyl, 2-chlorophenyl, 3,4-dichlorophenyl, 3-chlorophenyl, 3-trifluoromethylphenyl, 3-trifluoromethoxyphenyl, 4-fluorobenzyl, pyridin-2-yl, pyrimidin-2-ylmethyl , 5-chloropyridin-3-yl, 6-chloropyridin-3-yl, 5-fluoropyridin-3-yl, 6-methoxypyridin-3-yl, 5-trifluoromethyl-pyridin-3-yl, pyridin-3-ylmethyl, 6-fluoropyridin-3-yl, 6-methylpyridin-3-yl, 6-[6-chloropyridin-3-yloxy]pyridin-3-yl, 6-[6-fluoropyridin-3-yloxy]pyridin-3-yl, 6-{6-[6-fluoropyridin -3-yloxy]pyridin-3-yl}oxypyridin-3-yl, 4-methylpyridin-3-yl, 5-methylpyridin-3-yl, pyridin-3-yl, 6-trifluoromethylpyridin-3-yl, 6-chloro-5-methylpyridin-3-yl, 6-cyanopyridin-3-yl, 6-chloro-4-methylpyridin-3-yl, 5-methoxypyridin-3-yl, 6-bromopyridin-3-yl, 5-cyanopyridin-3-yl, quinolin-3-yl, 5,6-dimethoxypyridin-3-yl, 4-chloropyridin-3-yl, 2-chloropyridin-3-yl, 5-bromopyridin-3-yl, 5-chloro-2-methoxypyridin-3-yl, 2-fluoro-6-methylpyridin-3-yl, 3-cyanophenyl, 3-ethoxyphenyl, 3-acetamidophenyl, 3-ethylphenyl, 3-methoxyphenyl, 3-propylphenyl, 2-fluoro-3-trifluoromethylphenyl, 3-methylphenyl, 3-methylsulfonylphenyl, 3-phenoxyphenyl, 3-butylsulfanylphenyl, 4-fluoro-3-trifluoromethylphenyl, 3-methoxycarbonimidoylphenyl, 3-chloro-4-methylphenyl, 3-fluoro-5-trifluoromethylphenyl, 3-chloro-5-trifluoromethylphenyl, 3-chloro-5-methoxyphenyl, or 3-chloro-4-fluorophenyl or 3-trifluoromethylphenyl, T is O, S or NR 1b is] The present invention relates to the compound
[0228] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(vc)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4j and R 4k together with the nitrogen atom to which they are attached form a 5- or 6-membered heterocycle, which heterocycle contains a nitrogen atom as the heteroatom; T is O, S or NR 1b is] The present invention relates to the compound
[0229] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(via)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2is CH3, R 3 is H, R 4l is H, methyl, ethyl, isopropyl, 1-cyano-1-methylethyl or cyclopropyl, T 1 is as defined above, T is O, S or NR 1b is] The present invention relates to the compound
[0230] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(vib)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4m is methyl or ethyl, T is O, S or NR 1b is] The present invention relates to the compound
[0231] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(vic)[in the formula, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4n is H, methyl, ethyl, methylsulfonyl or cyclopropylsulfonyl, R 4ois H, methyl, ethyl, isopropyl, isobutyl, tert.butyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-methoxyethyl, cyanomethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, cyclopropyl, 1-cyanocyclopropyl, cyclopentyl, cyclopropylmethyl, methoxy, ethoxy, phenyl, pyridin-3-yl, phenylmethyl or 1-phenyl-2-hydroxyethyl, or R 4n and R 4o are both (CH2)5, (CH2)4, (CH2)3 or (CH2)2O(CH2)2, Y is O or S; T is O, S or NR 1b is] The present invention relates to the compound
[0232] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(vid)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4p is H, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which are unsubstituted or substituted as described above, or C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which are unsubstituted or substituted as described above, R 4qis H, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which are unsubstituted or substituted as described above, or C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which are unsubstituted or substituted as described above, R 4r is H, C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which may be unsubstituted or substituted as described above, or C3-C8-cycloalkyl or C3-C8-cycloalkyl-C1-C4-alkyl, which may be unsubstituted or substituted as described above, or aryl, hetaryl, arylalkyl or hetarylalkyl, which may be unsubstituted or substituted as described above, Y is O or S; T is O, S or NR 1b is] The present invention relates to the compound
[0233] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(vii) [wherein, R 1 is H, methyl, ethyl, preferably methyl and ethyl, R 2 is CH3, R 3 is H, chlorine, bromine, preferably H, R 4sare 3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 3-(methylsulfanyl)phenyl, pyrimidin-2-yl, 3-[(2,2,2-trifluoroethyl)sulfinyl]phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1-methyl-1H-pyrrol-2-yl, 3-furyl, 2,5-dimethyl-3-thienyl, 3-[(trifluoromethyl)sulfanyl]phenyl, 3-[(cyclopropylmethyl)sulfanyl]phenyl, 3-(methoxymethyl)phenyl, 3-[(tetrahydro-2H-pyran-4-yloxy)methyl]phenyl, 3-(dimethylsulfamoyl)phenyl, 3-(methylsulfonyl)phenyl , 4-methyl-3-(methylsulfanyl)phenyl, 1-(2-cyanophenyl)-1H-pyrazol-4-yl, 1-(4-fluorophenyl)-1H-pyrazol-4-yl, 1-phenyl-1H-pyrazol-4-yl, 1-naphthyl, 5-(methoxycarbonyl)-1-naphthyl, 4-fluoro-2-(methoxycarbonyl)phenyl, 4-fluoro-1-naphthyl, 4-chloro-3-(ethoxycarbonyl)phenyl, 2-(methoxycarbonyl)phenyl carbonyl)phenyl, pyridin-4-yl, 6-(ethoxycarbonyl)pyridin-2-yl, 3-(ethoxycarbonyl)phenyl, 2-naphthyl, 4-methoxy-3-(methoxycarbonyl)phenyl, 4-chloro-2-(methoxycarbonyl)phenyl, 3-thienyl, 3-(2-ethoxy-2-oxoethoxy)-4-methylphenyl, 3-(2-ethoxy-2-oxoethoxy)phenyl, 3-(2-ethoxy-2-oxoethoxy)4,5-difluorophenyl, 3-(2-ethoxy-2-oxoethoxy)-4-fluorophenyl, 3-(ethoxycarbonyl)-4-fluorophenyl, (3-{[(cyclopropylcarbonyl)oxy]methyl}phenyl, 3-{[(cyclopropylcarbonyl)oxy]methyl}-4-fluorophenyl, pyridin-2-yl, 3-(difluoromethyl)phenyl, 3-[(trifluoromethyl)sulfinyl]phenyl, 4-fluoro-3-(trifluoromethyl)phenyl, 3-chloro-5-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, 3-fluoro-5-(trifluoromethyl)phenyl, 4-cyano-3-(trifluoromethyl)phenyl, 3-(2,2,2-trifluoroethyl)phenyl, 3-(pentafluoroethyl)phenyl, 3-cyanophenyl, 4-chloro-3-cyanophenyl, 3-cyano-5-fluorophenyl, 3-cyano-5-(trifluoromethyl) Phenyl, 5-cyano-2-methoxyphenyl, 3-cyano-4-fluorophenyl, 5-cyanopyridin-3-yl, 5-cyano-6-(dimethylamine)pyridin-3-yl, 5-cyano-6-(morpholin-4-yl)pyridin-3-yl, 5-cyano-6-ethoxypyridin-3-yl, 5-cyano-6-methoxypyridin-3-yl, 3-chloro-5-cyanophenyl, 1-benzofuran-2-yl, 3-phenyl-1,2-oxazol-5-yl, 3-(ethoxycarbonyl)pyridin-3-yl (bornyl)-1,2-oxazol-5-yl, 1-isopropyl-1H-1,2,3-triazol-4-yl, 1-methyl-1H-1,2,3-triazol-4-yl, 5-cyano-6-methoxypyridin-3-yl, 6-methoxypyridin-2-yl, 2,3-dihydro-1-benzofuran-7-yl, 1-benzofuran-7-yl, 2,6-dimethoxypyridin-3-yl, 2-methoxyphenyl, 1,3-benzodioxol-4-yl, 2,4-dimethoxyphenyl, 2,5-Dimethoxyphenyl, 6-(trifluoromethyl)pyridin-2-yl, 5-chloro-2-methoxypyridin-3-yl, 2-methoxypyridin-3-yl, 6-ethoxypyridin-3-yl, 5-chloro-6-methoxypyridin-3-yl, 2-(methylsulfanyl)pyridin-3-yl, 2-ethoxypyridin-3-yl, 5,6-dimethoxypyridin-3-yl, 2-methoxypyridin-4-yl, 6-methoxy-5-(trifluoromethyl)pyridin-3-yl, 6-methoxy- 5-nitropyridin-3-yl, 2,6-dimethoxypyridin-4-yl, 2-(methylsulfanyl)phenyl, 2-methoxy-6-(trifluoromethyl)-pyridin-4-yl, 3-cyano-5-methoxyphenyl, 5-fluoro-2-methoxypyridin-3-yl, 6-isopropoxypyridin-3-yl, 6-methoxypyridin-3-yl, 2-(2-amino-2-oxoethoxy)phenyl, 3-cyano-4-isopropoxyphenyl, or 3-chloropyridin-2-yl, T is O, S or NR 1b is] The present invention relates to the compound
[0234] Another preferred embodiment is a compound of formula I as an active ingredient. * .B(viii) [wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4t is H, methyl, trifluoromethyl, trichloromethyl, isopropyl, isobutyl, isopentyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl or benzyl; R 4u is H or methyl, or R 4t and R 4uare both vinyl, prop-1-en-2-yl, (1E)-prop-1-en-1-yl, (1Z)-prop-1-en-1-yl or cyclopropyl; R 4v is H, S(O) m R 1E , OR 2E or N(R 3E )(R 4E ) and R 4t and / or R 4u is H or C1-C8-alkyl, R 4v is S(O) m R 1E , OR 2E or N(R 3E )(R 4E ) and R 1E is methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopropylmethyl, 2,2-dimethylpropyl, 2-methoxy-2-oxoethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl or 2-pyrimidyl, R 2E is H, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3-chlorophenyl or 4-chlorophenyl, R 3E and R 4E together with the nitrogen atom to which they are attached form a 5-membered heterocyclic ring, the heterocyclyl group of which contains 1 or 2 N atoms (the ring group may contain one CO group) and the C atoms of which are substituted by trifluoromethyl, methyl or cyclopropyl, T is O, S or NR 1b is] The present invention relates to the compound
[0235] A more preferred embodiment is a compound of formula I as the active ingredient. * .1.A(iiia) [where, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4a , R 4b and R 4c At least one of is C3-C4-cycloalkenyl, C3-C4-halocycloalkenyl, OR a or SR a and R a is C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl] The present invention relates to the compound
[0236] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(iiib) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4a is as defined above, A is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group. The present invention relates to the compound
[0237] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(iiic) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4a and R 4b is as defined above, E is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group. The present invention relates to the compound
[0238] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(iiid) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4d is C1-C2-haloalkyl or c-C3H5 (C atoms may be halogenated), G is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group. The present invention relates to the compound
[0239] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(iva) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4e is H or CH3, Q is a direct bond or □-branched or straight-chain C1-C8-alkylene, C2-C8-alkenylene or C2-C8-alkynylene, the carbon chain of which may be substituted or unsubstituted as previously described; M is O, S, NOCH3, or NSCH3. The present invention relates to the compound
[0240] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(ivb) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4fis H, C1-C4-alkyl or C3-C6-cycloalkyl, R 4g is H, C1-C4-alkyl or C3-C6-cycloalkyl, V is O or S; W is □-branched or straight chain C1-C8-alkylene, C3-C8-cycloalkylene or C3-C8-heterocycloalkylene, and W is substituted as described above. The present invention relates to the compound
[0241] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(va) [wherein, R 1 is H or CH3, preferably CH3, R 2 is CH3, R 3 is H, chlorine or bromine, preferably H, R 4his methyl, ethyl, n-butyl, n-pentyl, n-propyl, isopropyl, allyl, 3,3-dimethylallyl, propargyl, cyclohexyl, tetrahydropyranyl, tetrahydrothiopyranyl, 3-oxetanyl, 5-oxa-[3.3.0]-bicycloheptanyl, methoxyethyl, methoxypropyl, ethoxyethyl, ethylthioethyl, methylthioethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 3-chloro-2,2,3,3-tetrafluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl Pyr, 2,2,2-trifluoroethylthio-ethyl, methylcarbonyl-methyl, c-propylcarbonyl-methyl, tert.-butylcarbonyl-methyl, methoxycarbonyl-methyl, ethoxycarbonyl-methyl, hydroxycarbonyl-methyl, carbamoyl-methyl, N-methylcarbamoyl-methyl, Nc-propylcarbamoyl-methyl, N,N-dimethylcarbamoyl-methyl, 2-methoxymino-propyl, cyclopropylmethyl, phenyl, 4-methylphenyl, 2-nitrophenyl, 3-methylthiophenyl, 4-chloro-phenyl, 4-fluoro-phenyl, 4-tert.-butyl-phenyl, 4-methoxy-phenyl, 4-nitrophenyl, 4-dimethylamino-phenyl, 2-fluoro-phenyl, 2-methoxy-phenyl, 2-dimethylaminosulfonyl-phenyl, 2-dimethylaminocarbamoyl-phenyl, 3-nitrophenyl, 3-trifluoromethyl-phenyl, 3-chloro-phenyl, 2,5-dichloro-phenyl, 3,5-dichloro-phenyl, 4-chloro-3-trifluoromethyl-phenyl, 2,4,5-trichloro-phenyl 2-pyridyl, 5-(2-chloro)pyridyl, 2-(5-methyl)-pyridyl, 2-(6-methyl)-pyridyl, 2-(3-trifluoromethyl)-pyridyl, 2-pyrimidyl, 2-(4-methyl)-pyrimidyl, 2-(5-methyl)-pyrimidyl, 2-(4-methoxy)-pyrimidyl, 2-(5-fluoro)-pyrimidyl, 2-(4-trifluoromethyl)-pyrimidyl, 2-(5-trifluoromethyl)-pyrimidyl, 2-(4,6-dimethyl)-pyrimidyl, 2-(4,5 -dimethyl)-pyrimidyl, 2-(4,6-dimethoxy)-pyrimidyl, -CH2-2-pyrimidyl, -CH2-2-pyrazinyl, -CH2-5-(1-methyl)-imidazolyl, -CH2-3-(1-methyl)-pyrazolyl, -CH2-4-pyridyl, -CH2-2-pyridyl, -CH2-2-(1-methyl)-imidazolyl, -CH2-3-pyridyl, CH2-2-furanyl, -CH2-5-(2-chloro)-pyridyl, benzyl, 3,4-dichloro-benzyl, 2,6-difuranyl 2-Fluoro-6-methoxy-benzyl, 2,6-dichloro-benzyl, 2-chloro-6-tolylfluoromethyl-benzyl, 2-chloro-6-fluoro-benzyl, -CH2-2-(4,6-dimethoxy)-pyrimidyl, 2,6-dimethyl-benzyl, -CH2-1-(3-nitro-5-methyl)-pyrazolyl, 2-(1-methyl)-benzimidazolyl, 2-(5-methyl)-oxdiazolyl, 2-[3-methyl-6-(trifluoromethyl)-imidazo[4.5]-pyridinyl, 3-[4-ethyl-5-(trifluoromethyl)-]-1,2,4-triazolyl, 3-[4-methyl-5-(trifluoromethyl)]-1,2,4-triazolyl, 3-[4-methyl-5-(difluoromethyl)]-1,2,4-triazolyl, 2-(5-phenyl)-1,3,4-thiadiazolyl, 2-(1-methyl-5-phenyl)-imidazolyl, 2-(4,5-dimethyl)-oxazolyl, 2-(1-methyl-5-methoxycarbonyl)-imidazolyl, 2-(1-methyl)-imidazolyl, or 1,2-ethanediyl. m is 0 or 2, preferably 0. The present invention relates to the compound
[0242] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(vb) [wherein, R 1 is H, methyl, ethyl or cyclopropyl, R 2 is CH3, R 3 is H, chlorine or bromine, preferably H, R 4iis methyl, ethyl, propyl, isopropyl, cyclopentyl, sec-butyl, allyl, 3-methoxypropyl, 3-cyanopropyl, cyclohexyl, 3,3,3-trifluoropropyl, 3-fluoropropyl, 2-methylsulfanylethyl, 2-[(2,2,2-trifluoroethyl)sulfanyl]ethyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl, tetrahydrofuran-3-yl, tetrahydro-2H-pyran-4-yl, tetrahydro-2H-thiopyran-4-yl, phenyl, 3-methylsulfanylphenyl, 4-chlorophenyl, 4-fluorophenyl, 2,5-difluorophenyl, 2,4-difluorophenyl, 3,5-difluorophenyl, 2-chlorophenyl, 3,4-dichlorophenyl, 3-chlorophenyl, 3-trifluoromethylphenyl, 3-trifluoromethoxyphenyl, 4-fluorobenzyl, pyridin-2-yl, pyrimidin-2-ylmethyl , 5-chloropyridin-3-yl, 6-chloropyridin-3-yl, 5-fluoropyridin-3-yl, 6-methoxypyridin-3-yl, 5-trifluoromethyl-pyridin-3-yl, pyridin-3-ylmethyl, 6-fluoropyridin-3-yl, 6-methylpyridin-3-yl, 6-[6-chloropyridin-3-yloxy]pyridin-3-yl, 6-[6-fluoropyridin-3-yloxy]pyridin-3-yl, 6-{6-[6-fluoropyridin -3-yloxy]pyridin-3-yl}oxypyridin-3-yl, 4-methylpyridin-3-yl, 5-methylpyridin-3-yl, pyridin-3-yl, 6-trifluoromethylpyridin-3-yl, 6-chloro-5-methylpyridin-3-yl, 6-cyanopyridin-3-yl, 6-chloro-4-methylpyridin-3-yl, 5-methoxypyridin-3-yl, 6-bromopyridin-3-yl, 5-cyanopyridin-3-yl, quinolin-3-yl, 5,6-dimethoxypyridin-3-yl, 4-chloropyridin-3-yl, 2-chloropyridin-3-yl, 5-bromopyridin-3-yl, 5-chloro-2-methoxypyridin-3-yl, 2-fluoro-6-methylpyridin-3-yl, 3-cyanophenyl, 3-ethoxyphenyl, 3-acetamidophenyl, 3-ethylphenyl, 3-methoxyphenyl, 3-propylphenyl, 2-fluoro-3-trifluoromethylphenyl, 3-methylphenyl, 3-methylsulfonylphenyl, 3-phenoxyphenyl, 3-butylsulfanylphenyl, 4-fluoro-3-trifluoromethylphenyl, 3-methoxycarbonimidoylphenyl, 3-chloro-4-methylphenyl, 3-fluoro-5-trifluoromethylphenyl, 3-chloro-5-trifluoromethylphenyl, 3-chloro-5-methoxyphenyl, or 3-chloro-4-fluorophenyl or 3-trifluoromethylphenyl], The present invention relates to the compound
[0243] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(vc) [wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4j and R 4k together with the nitrogen atom to which they are attached form a 5- or 6-membered heterocycle, which heterocycle contains a nitrogen atom as the heteroatom. The present invention relates to the compound
[0244] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(via) [wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4lis H, methyl, ethyl, isopropyl, 1-cyano-1-methylethyl or cyclopropyl, T 1 is as defined above] The present invention relates to the compound
[0245] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(vib) [wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4m is methyl or ethyl] The present invention relates to the compound
[0246] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(vic)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4n is H, methyl, ethyl, methylsulfonyl or cyclopropylsulfonyl, R 4o is H, methyl, ethyl, isopropyl, isobutyl, tert.butyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-methoxyethyl, cyanomethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, cyclopropyl, 1-cyanocyclopropyl, cyclopentyl, cyclopropylmethyl, methoxy, ethoxy, phenyl, pyridin-3-yl, phenylmethyl or 1-phenyl-2-hydroxyethyl, or R 4n and R 4o are both (CH2)5, (CH2)4, (CH2)3 or (CH2)2O(CH2)2, Y is O or S. The present invention relates to the compound
[0247] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(vid)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4p is H, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which are unsubstituted or substituted as described above, or C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which are unsubstituted or substituted as described above, R 4q is H, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which are unsubstituted or substituted as described above, or C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which are unsubstituted or substituted as described above, R 4r is H, C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which may be unsubstituted or substituted as described above, or C3-C8-cycloalkyl or C3-C8-cycloalkyl-C1-C4-alkyl, which may be unsubstituted or substituted as described above, or aryl, hetaryl, arylalkyl or hetarylalkyl, which may be unsubstituted or substituted as described above, Y is O or S. The present invention relates to the compound
[0248] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(vii) [wherein, R 1 is H, methyl, ethyl, preferably methyl and ethyl, R 2 is CH3, R 3 is H, chlorine, bromine, preferably H, R 4sare 3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 3-(methylsulfanyl)phenyl, pyrimidin-2-yl, 3-[(2,2,2-trifluoroethyl)sulfinyl]phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1-methyl-1H-pyrrol-2-yl, 3-furyl, 2,5-dimethyl-3-thienyl, 3-[(trifluoromethyl)sulfanyl]phenyl, 3-[(cyclopropylmethyl)sulfanyl]phenyl, 3-(methoxymethyl)phenyl, 3-[(tetrahydro-2H-pyran-4-yloxy)methyl]phenyl, 3-(dimethylsulfamoyl)phenyl, 3-(methylsulfonyl)phenyl , 4-methyl-3-(methylsulfanyl)phenyl, 1-(2-cyanophenyl)-1H-pyrazol-4-yl, 1-(4-fluorophenyl)-1H-pyrazol-4-yl, 1-phenyl-1H-pyrazol-4-yl, 1-naphthyl, 5-(methoxycarbonyl)-1-naphthyl, 4-fluoro-2-(methoxycarbonyl)phenyl, 4-fluoro-1-naphthyl, 4-chloro-3-(ethoxycarbonyl)phenyl, 2-(methoxycarbonyl)phenyl carbonyl)phenyl, pyridin-4-yl, 6-(ethoxycarbonyl)pyridin-2-yl, 3-(ethoxycarbonyl)phenyl, 2-naphthyl, 4-methoxy-3-(methoxycarbonyl)phenyl, 4-chloro-2-(methoxycarbonyl)phenyl, 3-thienyl, 3-(2-ethoxy-2-oxoethoxy)-4-methylphenyl, 3-(2-ethoxy-2-oxoethoxy)phenyl, 3-(2-ethoxy-2-oxoethoxy)4,5-difluorophenyl, 3-(2-ethoxy-2-oxoethoxy)-4-fluorophenyl, 3-(ethoxycarbonyl)-4-fluorophenyl, (3-{[(cyclopropylcarbonyl)oxy]methyl}phenyl, 3-{[(cyclopropylcarbonyl)oxy]methyl}-4-fluorophenyl, pyridin-2-yl, 3-(difluoromethyl)phenyl, 3-[(trifluoromethyl)sulfinyl]phenyl, 4-fluoro-3-(trifluoromethyl)phenyl, 3-chloro-5-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, 3-fluoro-5-(trifluoromethyl)phenyl, 4-cyano-3-(trifluoromethyl)phenyl, 3-(2,2,2-trifluoroethyl)phenyl, 3-(pentafluoroethyl)phenyl, 3-cyanophenyl, 4-chloro-3-cyanophenyl, 3-cyano-5-fluorophenyl, 3-cyano-5-(trifluoromethyl) Phenyl, 5-cyano-2-methoxyphenyl, 3-cyano-4-fluorophenyl, 5-cyanopyridin-3-yl, 5-cyano-6-(dimethylamine)pyridin-3-yl, 5-cyano-6-(morpholin-4-yl)pyridin-3-yl, 5-cyano-6-ethoxypyridin-3-yl, 5-cyano-6-methoxypyridin-3-yl, 3-chloro-5-cyanophenyl, 1-benzofuran-2-yl, 3-phenyl-1,2-oxazol-5-yl, 3-(ethoxycarbonyl)pyridin-3-yl (bornyl)-1,2-oxazol-5-yl, 1-isopropyl-1H-1,2,3-triazol-4-yl, 1-methyl-1H-1,2,3-triazol-4-yl, 5-cyano-6-methoxypyridin-3-yl, 6-methoxypyridin-2-yl, 2,3-dihydro-1-benzofuran-7-yl, 1-benzofuran-7-yl, 2,6-dimethoxypyridin-3-yl, 2-methoxyphenyl, 1,3-benzodioxol-4-yl, 2,4-dimethoxyphenyl, 2,5-Dimethoxyphenyl, 6-(trifluoromethyl)pyridin-2-yl, 5-chloro-2-methoxypyridin-3-yl, 2-methoxypyridin-3-yl, 6-ethoxypyridin-3-yl, 5-chloro-6-methoxypyridin-3-yl, 2-(methylsulfanyl)pyridin-3-yl, 2-ethoxypyridin-3-yl, 5,6-dimethoxypyridin-3-yl, 2-methoxypyridin-4-yl, 6-methoxy-5-(trifluoromethyl)pyridin-3-yl, 6-methoxy- 5-nitropyridin-3-yl, 2,6-dimethoxypyridin-4-yl, 2-(methylsulfanyl)phenyl, 2-methoxy-6-(trifluoromethyl)-pyridin-4-yl, 3-cyano-5-methoxyphenyl, 5-fluoro-2-methoxypyridin-3-yl, 6-isopropoxypyridin-3-yl, 6-methoxypyridin-3-yl, 2-(2-amino-2-oxoethoxy)phenyl, 3-cyano-4-isopropoxyphenyl, or 3-chloropyridin-2-yl], The present invention relates to the compound
[0249] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(viii) [wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4t is H, methyl, trifluoromethyl, trichloromethyl, isopropyl, isobutyl, isopentyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl or benzyl; R 4u is H or methyl, or R 4t and R 4uare both vinyl, prop-1-en-2-yl, (1E)-prop-1-en-1-yl, (1Z)-prop-1-en-1-yl or cyclopropyl; R 4v is H, S(O) m R 1E , OR 2E or N(R 3E )(R 4E ) and R 4t and / or R 4u is H or C1-C8-alkyl, R 4v is S(O) m R 1E , OR 2E or N(R 3E )(R 4E ) and R 1E is methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopropylmethyl, 2,2-dimethylpropyl, 2-methoxy-2-oxoethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl or 2-pyrimidyl, R 2E is H, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3-chlorophenyl or 4-chlorophenyl, R 3E and R 4E together with the nitrogen atom to which they are attached form a 5-membered heterocyclic ring, the heterocyclyl group of which contains 1 or 2 N atoms (the ring group may contain one CO group) and the C atoms of which are substituted by trifluoromethyl, methyl or cyclopropyl. The present invention relates to the compound
[0250] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(iiia) R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4a , R 4b and R 4c At least one of is C3-C4-cycloalkenyl, C3-C4-halocycloalkenyl, OR a or SR a and R a is C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl.
[0251] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(iiib) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4a is as defined above, A is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group. The present invention relates to the compound
[0252] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(iiic) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4a and R 4b is as defined above, E is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group. The present invention relates to the compound
[0253] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(iiid) [wherein, R 1is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4d is C1-C2-haloalkyl or c-C3H5 (C atoms may be halogenated), G is a C3-C4-cycloalkenyl or C3-C4-halocycloalkenyl group. The present invention relates to the compound
[0254] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(iva) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4e is H or CH3, Q is a direct bond or □-branched or straight-chain C1-C8-alkylene, C2-C8-alkenylene or C2-C8-alkynylene, the carbon chain of which may be substituted or unsubstituted as previously described; M is O, S, NOCH3, or NSCH3. The present invention relates to the compound
[0255] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(ivb) [wherein, R 1 is H, CH3 or C2H5, preferably H or CH3, R 2 is CH3 or halomethyl, R 3 is H, R 4f is H, C1-C4-alkyl or C3-C6-cycloalkyl, R 4gis H, C1-C4-alkyl or C3-C6-cycloalkyl, V is O or S; W is □-branched or straight chain C1-C8-alkylene, C3-C8-cycloalkylene or C3-C8-heterocycloalkylene, and W is substituted as described above. The present invention relates to the compound
[0256] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(va) [wherein, R 1 is H or CH3, preferably CH3, R 2 is CH3, R 3 is H, chlorine or bromine, preferably H, R 4his methyl, ethyl, n-butyl, n-pentyl, n-propyl, isopropyl, allyl, 3,3-dimethylallyl, propargyl, cyclohexyl, tetrahydropyranyl, tetrahydrothiopyranyl, 3-oxetanyl, 5-oxa-[3.3.0]-bicycloheptanyl, methoxyethyl, methoxypropyl, ethoxyethyl, ethylthioethyl, methylthioethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 3-chloro-2,2,3,3-tetrafluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl Pyr, 2,2,2-trifluoroethylthio-ethyl, methylcarbonyl-methyl, c-propylcarbonyl-methyl, tert.-butylcarbonyl-methyl, methoxycarbonyl-methyl, ethoxycarbonyl-methyl, hydroxycarbonyl-methyl, carbamoyl-methyl, N-methylcarbamoyl-methyl, Nc-propylcarbamoyl-methyl, N,N-dimethylcarbamoyl-methyl, 2-methoxymino-propyl, cyclopropylmethyl, phenyl, 4-methylphenyl, 2-nitrophenyl, 3-methylthiophenyl, 4-chloro-phenyl, 4-fluoro-phenyl, 4-tert.-butyl-phenyl, 4-methoxy-phenyl, 4-nitrophenyl, 4-dimethylamino-phenyl, 2-fluoro-phenyl, 2-methoxy-phenyl, 2-dimethylaminosulfonyl-phenyl, 2-dimethylaminocarbamoyl-phenyl, 3-nitrophenyl, 3-trifluoromethyl-phenyl, 3-chloro-phenyl, 2,5-dichloro-phenyl, 3,5-dichloro-phenyl, 4-chloro-3-trifluoromethyl-phenyl, 2,4,5-trichloro-phenyl 2-pyridyl, 5-(2-chloro)pyridyl, 2-(5-methyl)-pyridyl, 2-(6-methyl)-pyridyl, 2-(3-trifluoromethyl)-pyridyl, 2-pyrimidyl, 2-(4-methyl)-pyrimidyl, 2-(5-methyl)-pyrimidyl, 2-(4-methoxy)-pyrimidyl, 2-(5-fluoro)-pyrimidyl, 2-(4-trifluoromethyl)-pyrimidyl, 2-(5-trifluoromethyl)-pyrimidyl, 2-(4,6-dimethyl)-pyrimidyl, 2-(4,5 -dimethyl)-pyrimidyl, 2-(4,6-dimethoxy)-pyrimidyl, -CH2-2-pyrimidyl, -CH2-2-pyrazinyl, -CH2-5-(1-methyl)-imidazolyl, -CH2-3-(1-methyl)-pyrazolyl, -CH2-4-pyridyl, -CH2-2-pyridyl, -CH2-2-(1-methyl)-imidazolyl, -CH2-3-pyridyl, CH2-2-furanyl, -CH2-5-(2-chloro)-pyridyl, benzyl, 3,4-dichloro-benzyl, 2,6-difuranyl 2-Fluoro-6-methoxy-benzyl, 2,6-dichloro-benzyl, 2-chloro-6-tolylfluoromethyl-benzyl, 2-chloro-6-fluoro-benzyl, -CH2-2-(4,6-dimethoxy)-pyrimidyl, 2,6-dimethyl-benzyl, -CH2-1-(3-nitro-5-methyl)-pyrazolyl, 2-(1-methyl)-benzimidazolyl, 2-(5-methyl)-oxdiazolyl, 2-[3-methyl-6-(trifluoromethyl)-imidazo[4.5]-pyridinyl, 3-[4-ethyl-5-(trifluoromethyl)-]-1,2,4-triazolyl, 3-[4-methyl-5-(trifluoromethyl)]-1,2,4-triazolyl, 3-[4-methyl-5-(difluoromethyl)]-1,2,4-triazolyl, 2-(5-phenyl)-1,3,4-thiadiazolyl, 2-(1-methyl-5-phenyl)-imidazolyl, 2-(4,5-dimethyl)-oxazolyl, 2-(1-methyl-5-methoxycarbonyl)-imidazolyl, 2-(1-methyl)-imidazolyl, or 1,2-ethanediyl. m is 0 or 2, preferably 0. The present invention relates to the compound
[0257] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(vb) [wherein, R 1 is H, methyl, ethyl or cyclopropyl, R 2 is CH3, R 3 is H, chlorine or bromine, preferably H, R 4iis methyl, ethyl, propyl, isopropyl, cyclopentyl, sec-butyl, allyl, 3-methoxypropyl, 3-cyanopropyl, cyclohexyl, 3,3,3-trifluoropropyl, 3-fluoropropyl, 2-methylsulfanylethyl, 2-[(2,2,2-trifluoroethyl)sulfanyl]ethyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl, tetrahydrofuran-3-yl, tetrahydro-2H-pyran-4-yl, tetrahydro-2H-thiopyran-4-yl, phenyl, 3-methylsulfanylphenyl, 4-chlorophenyl, 4-fluorophenyl, 2,5-difluorophenyl, 2,4-difluorophenyl, 3,5-difluorophenyl, 2-chlorophenyl, 3,4-dichlorophenyl, 3-chlorophenyl, 3-trifluoromethylphenyl, 3-trifluoromethoxyphenyl, 4-fluorobenzyl, pyridin-2-yl, pyrimidin-2-ylmethyl , 5-chloropyridin-3-yl, 6-chloropyridin-3-yl, 5-fluoropyridin-3-yl, 6-methoxypyridin-3-yl, 5-trifluoromethyl-pyridin-3-yl, pyridin-3-ylmethyl, 6-fluoropyridin-3-yl, 6-methylpyridin-3-yl, 6-[6-chloropyridin-3-yloxy]pyridin-3-yl, 6-[6-fluoropyridin-3-yloxy]pyridin-3-yl, 6-{6-[6-fluoropyridin -3-yloxy]pyridin-3-yl}oxypyridin-3-yl, 4-methylpyridin-3-yl, 5-methylpyridin-3-yl, pyridin-3-yl, 6-trifluoromethylpyridin-3-yl, 6-chloro-5-methylpyridin-3-yl, 6-cyanopyridin-3-yl, 6-chloro-4-methylpyridin-3-yl, 5-methoxypyridin-3-yl, 6-bromopyridin-3-yl, 5-cyanopyridin-3-yl, quinolin-3-yl, 5,6-dimethoxypyridin-3-yl, 4-chloropyridin-3-yl, 2-chloropyridin-3-yl, 5-bromopyridin-3-yl, 5-chloro-2-methoxypyridin-3-yl, 2-fluoro-6-methylpyridin-3-yl, 3-cyanophenyl, 3-ethoxyphenyl, 3-acetamidophenyl, 3-ethylphenyl, 3-methoxyphenyl, 3-propylphenyl, 2-fluoro-3-trifluoromethylphenyl, 3-methylphenyl, 3-methylsulfonylphenyl, 3-phenoxyphenyl, 3-butylsulfanylphenyl, 4-fluoro-3-trifluoromethylphenyl, 3-methoxycarbonimidoylphenyl, 3-chloro-4-methylphenyl, 3-fluoro-5-trifluoromethylphenyl, 3-chloro-5-trifluoromethylphenyl, 3-chloro-5-methoxyphenyl, or 3-chloro-4-fluorophenyl or 3-trifluoromethylphenyl], The present invention relates to the compound
[0258] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(vc) [wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4j and R 4k together with the nitrogen atom to which they are attached form a 5- or 6-membered heterocycle, which heterocycle contains a nitrogen atom as the heteroatom. The present invention relates to the compound
[0259] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(via) [wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4lis H, methyl, ethyl, isopropyl, 1-cyano-1-methylethyl or cyclopropyl, T 1 is as defined above] The present invention relates to the compound
[0260] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(vib) [wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4m is methyl or ethyl] The present invention relates to the compound
[0261] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(vic)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4n is H, methyl, ethyl, methylsulfonyl or cyclopropylsulfonyl, R 4o is H, methyl, ethyl, isopropyl, isobutyl, tert.butyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-methoxyethyl, cyanomethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, cyclopropyl, 1-cyanocyclopropyl, cyclopentyl, cyclopropylmethyl, methoxy, ethoxy, phenyl, pyridin-3-yl, phenylmethyl or 1-phenyl-2-hydroxyethyl, or R 4n and R 4o are both (CH2)5, (CH2)4, (CH2)3 or (CH2)2O(CH2)2, Y is O or S. The present invention relates to the compound
[0262] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(vid)[wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4p is H, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which are unsubstituted or substituted as described above, or C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which are unsubstituted or substituted as described above, R 4q is H, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which are unsubstituted or substituted as described above, or C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which are unsubstituted or substituted as described above, R 4r is H, C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which may be unsubstituted or substituted as described above, or C3-C8-cycloalkyl or C3-C8-cycloalkyl-C1-C4-alkyl, which may be unsubstituted or substituted as described above, or aryl, hetaryl, arylalkyl or hetarylalkyl, which may be unsubstituted or substituted as described above, Y is O or S. The present invention relates to the compound
[0263] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(vii) [wherein, R 1 is H, methyl, ethyl, preferably methyl and ethyl, R 2 is CH3, R 3 is H, chlorine, bromine, preferably H, R 4sare 3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 3-(methylsulfanyl)phenyl, pyrimidin-2-yl, 3-[(2,2,2-trifluoroethyl)sulfinyl]phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1-methyl-1H-pyrrol-2-yl, 3-furyl, 2,5-dimethyl-3-thienyl, 3-[(trifluoromethyl)sulfanyl]phenyl, 3-[(cyclopropylmethyl)sulfanyl]phenyl, 3-(methoxymethyl)phenyl, 3-[(tetrahydro-2H-pyran-4-yloxy)methyl]phenyl, 3-(dimethylsulfamoyl)phenyl, 3-(methylsulfonyl)phenyl , 4-methyl-3-(methylsulfanyl)phenyl, 1-(2-cyanophenyl)-1H-pyrazol-4-yl, 1-(4-fluorophenyl)-1H-pyrazol-4-yl, 1-phenyl-1H-pyrazol-4-yl, 1-naphthyl, 5-(methoxycarbonyl)-1-naphthyl, 4-fluoro-2-(methoxycarbonyl)phenyl, 4-fluoro-1-naphthyl, 4-chloro-3-(ethoxycarbonyl)phenyl, 2-(methoxycarbonyl)phenyl carbonyl)phenyl, pyridin-4-yl, 6-(ethoxycarbonyl)pyridin-2-yl, 3-(ethoxycarbonyl)phenyl, 2-napthyl, 4-methoxy-3-(methoxycarbonyl)phenyl, 4-chloro-2-(methoxycarbonyl)phenyl, 3-thienyl, 3-(2-ethoxy-2-oxoethoxy)-4-methylphenyl, 3-(2-ethoxy-2-oxoethoxy)phenyl, 3-(2-ethoxy-2-oxoethoxy)4,5-difluorophenyl, 3-(2-ethoxy-2-oxoethoxy)-4-fluorophenyl, 3-(ethoxycarbonyl)-4-fluorophenyl, (3-{[(cyclopropylcarbonyl)oxy]methyl}phenyl, 3-{[(cyclopropylcarbonyl)oxy]methyl}-4-fluorophenyl, pyridin-2-yl, 3-(difluoromethyl)phenyl, 3-[(trifluoromethyl)sulfinyl]phenyl, 4-fluoro-3-(trifluoromethyl)phenyl, 3-chloro-5-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, 3-fluoro-5-(trifluoromethyl)phenyl, 4-cyano-3-(trifluoromethyl)phenyl, 3-(2,2,2-trifluoroethyl)phenyl, 3-(pentafluoroethyl)phenyl, 3-cyanophenyl, 4-chloro-3-cyanophenyl, 3-cyano-5-fluorophenyl, 3-cyano-5-(trifluoromethyl) Phenyl, 5-cyano-2-methoxyphenyl, 3-cyano-4-fluorophenyl, 5-cyanopyridin-3-yl, 5-cyano-6-(dimethylamine)pyridin-3-yl, 5-cyano-6-(morpholin-4-yl)pyridin-3-yl, 5-cyano-6-ethoxypyridin-3-yl, 5-cyano-6-methoxypyridin-3-yl, 3-chloro-5-cyanophenyl, 1-benzofuran-2-yl, 3-phenyl-1,2-oxazol-5-yl, 3-(ethoxycarbonyl)pyridin-3-yl (bornyl)-1,2-oxazol-5-yl, 1-isopropyl-1H-1,2,3-triazol-4-yl, 1-methyl-1H-1,2,3-triazol-4-yl, 5-cyano-6-methoxypyridin-3-yl, 6-methoxypyridin-2-yl, 2,3-dihydro-1-benzofuran-7-yl, 1-benzofuran-7-yl, 2,6-dimethoxypyridin-3-yl, 2-methoxyphenyl, 1,3-benzodioxol-4-yl, 2,4-dimethoxyphenyl, 2,5-Dimethoxyphenyl, 6-(trifluoromethyl)pyridin-2-yl, 5-chloro-2-methoxypyridin-3-yl, 2-methoxypyridin-3-yl, 6-ethoxypyridin-3-yl, 5-chloro-6-methoxypyridin-3-yl, 2-(methylsulfanyl)pyridin-3-yl, 2-ethoxypyridin-3-yl, 5,6-dimethoxypyridin-3-yl, 2-methoxypyridin-4-yl, 6-methoxy-5-(trifluoromethyl)pyridin-3-yl, 6-methoxy- 5-nitropyridin-3-yl, 2,6-dimethoxypyridin-4-yl, 2-(methylsulfanyl)phenyl, 2-methoxy-6-(trifluoromethyl)-pyridin-4-yl, 3-cyano-5-methoxyphenyl, 5-fluoro-2-methoxypyridin-3-yl, 6-isopropoxypyridin-3-yl, 6-methoxypyridin-3-yl, 2-(2-amino-2-oxoethoxy)phenyl, 3-cyano-4-isopropoxyphenyl, or 3-chloropyridin-2-yl], The present invention relates to the compound
[0264] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.B(viii) [wherein, R 1 is methyl, ethyl or cyclopropyl; R 2 is CH3, R 3 is H, R 4t is H, methyl, trifluoromethyl, trichloromethyl, isopropyl, isobutyl, isopentyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl or benzyl; R 4u is H or methyl, or R 4t and R 4uare both vinyl, prop-1-en-2-yl, (1E)-prop-1-en-1-yl, (1Z)-prop-1-en-1-yl or cyclopropyl; R 4v is H, S(O) m R 1E , OR 2E or N(R 3E )(R 4E ) and R 4t and / or R 4u is H or C1-C8-alkyl, R 4v is S(O) m R 1E , OR 2E or N(R 3E )(R 4E ) and R 1E is methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopropylmethyl, 2,2-dimethylpropyl, 2-methoxy-2-oxoethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl or 2-pyrimidyl, R 2E is H, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3-chlorophenyl or 4-chlorophenyl, R 3E and R 4E together with the nitrogen atom to which they are attached form a 5-membered heterocyclic ring, the heterocyclyl group of which contains 1 or 2 N atoms (the ring group may contain one CO group) and the C atoms of which are substituted by trifluoromethyl, methyl or cyclopropyl. The present invention relates to the compound
[0265] An even more preferred embodiment is a compound of formula I as an active ingredient. * .1.A(vic), I * .1.A(vii) or I * .1.A(viii) [wherein, R 1 is H, methyl or ethyl, R 2 is CH3, R 3 is H, R 4n , R 4o is methyl, R 4s is phenyl, R 4t and R 4u are both cyclopropyl, R 4v is H, Y is O] The present invention relates to the compound
[0266] In particular, preferred are the compounds of formula I disclosed in PCT / EP2019 / 050537, pages 60-83, tables 1-46, collectively and as single embodiments of the active ingredient in the pesticide composition, which are hereby incorporated by reference.
[0267] The pesticide composition can be prepared by known methods, such as those described in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001, or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. The pesticide composition is typically prepared by contacting ethoxylated ricinolein with an active ingredient, preferably in the presence of water. In one embodiment, the resulting mixture is then subjected to milling or grinding to form a suspension of the active ingredient. In another embodiment, the active ingredient is contacted with water, milled or grinded to form an aqueous suspension of the active ingredient, and the aqueous suspension is contacted with ethoxylated ricinolein.
[0268] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, moisturizing agents, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, tackifiers and binders.
[0269] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling mineral oil fractions, e.g., kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g., toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g., ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e.g., cyclohexanone; esters, e.g., lactate esters, carbonate esters, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g., N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
[0270] Suitable solid carriers or fillers are mineral earths, such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin, such as cereal meal, bark flour, wood flour, nut shell flour and mixtures thereof.
[0271] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetters, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Edition or North American Edition).
[0272] Suitable anionic surfactants include alkali, alkaline earth, or ammonium salts of sulfonates, sulfates, phosphates, and carboxylates, and mixtures thereof. Examples of sulfonates include alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalene and alkylnaphthalenes, sulfosuccinates, and sulfosuccinamates. Examples of sulfates include sulfates of fatty acids and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid esters. Examples of phosphates include phosphoric acid esters. Examples of carboxylates include alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
[0273] Suitable nonionic surfactants include alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates include compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide, preferably ethylene oxide, can be used for alkoxylation. Examples of N-substituted fatty acid amides include fatty acid glucamides or fatty acid alkanolamides. Examples of esters include fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar-based surfactants include sorbitan, ethoxylated sorbitan, sucrose esters, and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants include homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.
[0274] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetaines and imidazolines. Suitable block polymers are AB or ABA type block polymers containing polyethylene oxide and polypropylene oxide blocks, or ABC type block polymers containing alkanol, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are polyacrylic acid or alkali salts of polyacid comb polymers. Examples of polybases are polyvinylamine or polyethyleneamine.
[0275] Suitable adjuvants are compounds that have negligible or even no pesticidal efficacy themselves, but improve the biological performance of Compound I against the target. Examples are surfactants, mineral or vegetable oils, and other adjuvants. Further examples are listed in Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
[0276] Suitable thickening agents are polysaccharides (eg xanthan gum, carboxymethylcellulose), organoclays (organically modified or unmodified), polycarboxylates and silicates.
[0277] Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones.
[0278] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.
[0279] Suitable antifoaming agents are silicones, long chain alcohols and salts of fatty acids.
[0280] Suitable colorants (e.g., red, blue, or green) are pigments with low water solubility and water soluble dyes. Examples are inorganic colorants (e.g., iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g., alizarin, azo, and phthalocyanine colorants).
[0281] Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes, and cellulose ethers.
[0282] The pesticide composition may contain further auxiliaries as needed, for example, 0.1 to 1 wt% of a bactericide, 5 to 15 wt% of an antifreeze agent, 0.1 to 1 wt% of an antifoaming agent, and 0.1 to 1 wt% of a colorant.
[0283] Solutions for seed treatment (LS), suspoemulsions (SE), and flowable concentrates (FS) are typically used for the treatment of plant propagation material, especially seeds. The compositions in question, after 2- to 10-fold dilution, provide active substance concentrations of 0.01 to 60% by weight, preferably 0.1 to 40% by weight, in ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying agrochemical compositions to plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, dipping, and in-furrow application of the propagation material. Preferably, the agrochemical compositions are applied to plant propagation material by methods that do not induce germination, such as dressing, pelleting, coating, and dusting the seeds.
[0284] When used for plant protection, the amount of active ingredient applied is, depending on the type of effect desired, 0.001 to 2 kg / ha, preferably 0.005 to 2 kg / ha, more preferably 0.05 to 0.9 kg / ha, in particular 0.1 to 0.75 kg / ha.
[0285] In the treatment of plant propagation material, such as seeds, for example by dusting, coating or drenching the seeds, an amount of active ingredient of 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g, most preferably 5 to 100 g per 100 kilograms of plant propagation material (preferably seeds) is generally required.
[0286] When used in the protection of materials or stored products, the amount of active ingredient applied depends on the type of application area and the desired effect. Amounts customarily applied in the protection of materials are from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active substance per cubic meter of treated material.
[0287] Various types of oils, wetters, adjuvants, fertilizers or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the agrochemical composition as a premix or, if appropriate, only immediately before use (tank mix). These agents can be incorporated into the composition according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.
[0288] The user typically applies the composition according to the invention from a pre-dosing device, a knapsack sprayer, a spray tank, a spray plane or an irrigation system. The agrochemical composition is typically adjusted to the desired application concentration with water, buffers and / or further auxiliaries, and a ready-to-use spray solution or agrochemical composition according to the invention is thus obtained. Typically, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray solution are applied per hectare of agriculturally useful area.
[0289] According to one embodiment, the individual components of the composition according to the invention, for example parts of a kit or parts of a binary or ternary mixture, may be mixed by the user himself in a spray tank, and, if appropriate, further auxiliaries may be added.
[0290] Application method The pesticide composition is suitable for use in protecting crops, plants, plant propagation material such as seeds, or the soil or water in which the plants are growing, from attack or infestation by animal pests. Thus, the present invention also relates to a method of protecting plants, which comprises contacting the crops, plants, plant propagation material such as seeds, or the soil or water in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of the pesticide composition.
[0291] A pesticide composition suitable for use in combating or controlling animal pests. Thus, the present invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pest, its habitat, breeding ground or food supply, or a crop, plant, plant propagation material, such as a seed or soil, or an area, material or environment in which the animal pest is growing or may grow, with a pesticidally effective amount of the pesticide composition of the present invention.
[0292] The pesticidal compositions are effective through both contact and ingestion. Furthermore, the pesticidal compositions can be applied to any and all developmental stages, including eggs, larvae, pupae, and adults.
[0293] Application can be carried out both before and after the infestation of the crop, plant, plant propagation material, such as seeds, soil or area, material or environment by pests.
[0294] Suitable application methods include, inter alia, soil treatment, seed treatment, in-furrow application, and foliar application. Soil treatment methods include soil dredging, drip irrigation (drip application to the soil), root, tuber, or bulb impregnation, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. In-furrow application typically involves the steps of creating furrows in cultivated land, sowing seeds in the furrows, applying the pesticide composition to the furrows, and closing the furrows. Foliar application refers to applying the pesticide composition to plant leaves, for example, through a spray device. For foliar application, it may be advantageous to use pheromones in combination with the pesticide composition to modify pest behavior. Suitable pheromones for specific crops and pests are known to those skilled in the art and are publicly available from pheromone and semiochemical databases, for example, http: / / www.pherobase.com.
[0295] As used herein, the term "contacting" includes both direct contact (applying the pesticide composition directly to the animal pest or plant, typically to the foliage, stem or roots of the plant) and indirect contact (applying the pesticide composition to the locus, i.e., the habitat, breeding ground, plant, seed, soil, area, material or environment of the animal pest or plant in which the pest is growing or may grow).
[0296] The term "animal pests" includes arthropods, gastropods and nematodes. Preferred animal pests according to the present invention are arthropods, preferably insects and arachnids, especially insects. Insects that are particularly associated with agricultural crops are typically called crop pests.
[0297] The term "crop" refers to both growing and harvested crops.
[0298] The term "plant" refers to cereals such as durum wheat and other wheats, rye, barley, triticale, oats, rice or corn (including fodder corn and sugar maize). maize / sweet corn and field corn); beets, for example, sugar beet or fodder beet; fruits, for example, pome fruits, stone fruits or soft fruits, for example, apple, pear, plum, peach, nectarine, almond, cherry, papaya, strawberry, raspberry, blackberry or gooseberry; legumes, for example, beans, lentils, peas, alfalfa or soybean; oil plants, for example, rapeseed (oilseed), turnip rape, mustard, olive, sunflower, coconut, cocoa bean, castor oil plant, oil palm, peanut or soybean; cucurbits, for example, squash, pumpkin, cucumber or melon; fiber plants, for example, cotton, flax, hemp or jute; citrus fruits, for example, orange, lemon, grapefruit or mandarin; vegetables, for example, eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbage, carrot, onion, garlic, leek, tomato, potato, cucurbit or sweet pepper; laurel plants, for example avocado, cinnamon or camphor; energy and raw material plants, for example corn, soybean, rapeseed, sugarcane or oil palm; tobacco; nuts, for example walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice vines); hops; sweet leaf (also called stevia); rubber plants or ornamental and forestry plants, for example flowers (e.g. carnation, petunia, geranium / pelargonium, pansy and impatiens), shrubs, broad-leaved trees (e.g. poplar) or evergreen trees, for example conifers; eucalyptus; turf; turf; pasture, for example for animal feed or ornamental use. Preferred plants include potato, sugar beet, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybean, rapeseed, legumes, sunflower, coffee or sugarcane; fruits; vines, ornamentals; or vegetables such as cucumber, tomato, bean or squash.
[0299] The term "cultivated plant" should be understood to include plants that have been modified by mutagenesis or genetic engineering to provide the plant with new traits or to modify traits that are already present.
[0300] For soil treatment, in-furrow application, or application to pest habitats or nests, the amount of active ingredient is 2 0.0001 to 500g per 100ml 2 The range is from 0.001 to 20g per serving.
[0301] For use in the treatment of crop plants, for example by foliar application, the rate of application of the active ingredient of this invention may be in the range of from 0.0001g to 4000g per hectare, for example, from 1g to 2kg per hectare or from 1g to 750g per hectare, desirably from 1g to 100g per hectare, more desirably from 10g to 50g per hectare, for example, from 10 to 20g per hectare, from 20 to 30g per hectare, from 30 to 40g per hectare or from 40 to 50g per hectare.
[0302] The following sections represent embodiments of the present invention.
[0303] Section 1: a) suspended particles of the active ingredient; and b) ethoxylated ricinolein; wherein the active ingredient has a water solubility of at least 1 g / L at 25°C; and the ethoxylated ricinolein, in polymerized form, contains 35 to 50 ethylene oxide molecules per ricinolein molecule.
[0304] Section 2: Item 1. The pesticide composition according to Item 1, wherein the ethoxylated ricinolein contains 38 to 42 ethylene oxide molecules per ricinolein molecule in polymerized form.
[0305] Section 3: Item 3. The pesticide composition according to Item 1 or 2, wherein the water solubility of the active ingredient is at least 10 g / L at 25°C.
[0306] Section 4: Item 4. The pesticide composition according to any one of Items 1 to 3, wherein the water solubility of the active ingredient is up to 100 g / L at 25°C.
[0307] Section 5: Item 5. The pesticide composition according to any one of Items 1 to 4, wherein the suspended particles have a median diameter of 0.5 μm to 20 μm.
[0308] Item 6: The active ingredient is of formula I
[0309] [ka] [In the formula, R P1 , R P2 , and R P3 are independently of one another H, CN, halogen, C1-C4-alkyl, C1-C3-haloalkyl, C1-C4-alkoxy, C1-C3-haloalkoxy, C1-C4-alkylthio, C1-C3-haloalkylthio, C1-C4-alkylsulfinyl, C1-C3-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C3-haloalkylsulfonyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl or C1-C4-alkoxy-C1-C4-alkyl; Z 1 is N or CH; Z 2 is N or CH; Z 3 is N or CR 4 and; T is S, O, or NR 1b and R 1b H, C1~C 10 -Alkyl, C1-C4-haloalkyl, C3-C 10 -Cycloalkyl, C3-C10 -Cycloalkylmethyl, C3-C 10 -Halocycloalkyl, C2-C 10 -Alkenyl, C2-C 10 -Haloalkenyl, C2-C 10 -Alkynyl, C1-C 10 -alkoxy-C1-C4-alkyl, OR a , 3- to 10-membered heterocyclyl, 3- to 10-membered heterocyclyl-C1-C4-alkyl, aryl, hetaryl, aryl-C1-C4-alkyl, or hetaryl-C1-C4-alkyl, and the cyclic moiety is unsubstituted or has one or more of the same or different substituents R aa is replaced by; R 1 H, CN, C1~C 10 -Alkyl, C1-C 10 -Haloalkyl, C3-C 10 -Cycloalkyl, C3-C 10 -halocycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C 10 -Alkenyl, C2-C 10 -Haloalkenyl, C2-C 10 -Alkynyl, C3-C 10 -haloalkynyl, C1-C5-alkylene-CN, OR a , C1-C5-alkylene-OR a , C(Y)R b , C1-C5-alkylene-C(Y)R b , C(Y)OR c , C1-C5-alkylene-C(Y)OR c , S(O)2R d , N.R. e R f , C1-C5-alkylene-NR e R f , C(Y)NR g R h , C1-C5-alkylene-C(Y)NR g R h , S(O) m NR e R f , C(Y)NR i NR e Rf , C1-C5-alkylene-S(O)2R d , C1-C5-alkylene-S(O) m NR e R f , C1-C5-alkylene-C(Y)NR i NR e R f , aryl, 3-10 membered heterocyclyl, hetaryl, aryl-C1-C5-alkyl, C3-C 10 -cycloalkyl-C1-C5-alkyl, 3- to 10-membered heterocyclyl-C1-C5-alkyl, or hetaryl-C1-C5-alkyl, wherein the cyclic moiety is unsubstituted or has one or more identical or different substituents R y and / or R x is replaced by; R 2 H, CN, C1~C 10 -Alkyl, C2-C 10 -Alkenyl, C2-C 10 -alkynyl, L 1 -C3~C 10 -cycloalkyl, L 1 -(3- to 6-membered heterocyclyl), L 1 -aryl, or L 1 -heteroaryl, the heterocyclyl group of which may be substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 3A and the cyclic group may contain one or more CO groups, which may be unsubstituted or may contain one or more of the same or different substituents R x is replaced by; L 1 is a direct bond, C1-C8-alkylene, C2-C8-alkenylene, C2-C8-alkynylene, or C3-C6-cycloalkylene, and the C atoms are unsubstituted or substituted with one or more identical or different substituents R x is replaced by; R 3 H, halogen, CN, C1-C 10 -Alkyl, C1-C 10 -Haloalkyl, C1-C 10 -alkoxy or C1-C10 -haloalkoxy, R 4 teeth, (i) H, CN, NO2, halogens, C1-C 10 -Alkyl, C2-C 10 -alkenyl, or C2-C 10 -alkynyl, and the C atoms are unsubstituted or have one or more identical or different substituents R x is substituted with; or OR a , S.R. d , C(Y)R b , C(Y)OR c , S(O)R d , S(O)2R d , N.R. e R f , C(Y)NR g R h , S(O) m NR e R f , C(Y)NR i NR e R f , C1-C5-alkylene-OR a , C1-C5-alkylene-CN, C1-C5-alkylene-C(Y)R b , C1-C5-alkylene-C(Y)OR c , C1-C5-alkylene-NR e R f , C1-C5-alkylene-C(Y)NR g R h , C1-C5-alkylene-S(O) m R d , C1-C5-alkylene-S(O) m NR e R f , C1-C5-alkylene-NR i NR e R f or 3-10 membered heterocyclyl, hetaryl, C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkenyl, aryl, 3-10 membered heterocyclyl-C1-C5-alkyl, hetaryl-C1-C5-alkyl, C3-C 10-Cycloalkyl-C1-C5-alkyl, C3-C 10 -cycloalkenyl-C1-C5-alkyl or aryl-C1-C5-alkyl, the cyclic moiety being unsubstituted or substituted by one or more of the same or different substituents R y is replaced by; or R 4 teeth, (ii)L 2 -C3~C 10 -cycloalkenyl, L 2 -C3~C 10 -cycloalkenyloxy, or L 2 -C3~C 10 -cycloalkenylthio, wherein the cycloalkenyl ring is unsubstituted or has one or more of the same or different substituents R y is replaced by; L 2 is C1-C8-alkylene, C2-C8-alkenylene, C2-C8-alkynylene or C3-C6-cycloalkylene, the C atoms being unsubstituted or substituted with one or more identical or different substituents R x is replaced by; or R 4 teeth, (iii) any one of the following groups:
[0310] [ka] R 4a , R 4b and R 4c are, independently of each other, H, halogen, CN, NO2, C1-C 10 -Alkyl, C2-C 10 -alkenyl, or C2-C 10 -alkynyl, and the C atoms are unsubstituted or have one or more identical or different substituents R x is replaced by; C1~C 10 -Haloalkyl, C1-C 10 -alkoxy, or C1-C4-alkoxy-C1-C 10-alkyl, and the C atoms are unsubstituted or have one or more identical or different substituents R y is replaced by; OR a , S.R. a , C(Y)R b , C(Y)OR c , C(Y)NR g R h , C(Y)NR i NR e R f , S(O) m R d , S(O) m NR e R f , C1-C5-alkylene-OR a , C1-C5-alkylene-CN, C1-C5-alkylene-C(Y)R b , C1-C5-alkylene-C(Y)OR c , C1-C5-alkylene-NR e R f , C1-C5-alkylene-C(Y)NR g R h , C1-C5-alkylene-S(O) m R d , C1-C5-alkylene-S(O) m NR e R f or C1-C5-alkylene-NR i NR e R f ; 3-10 membered heterocyclyl, C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkenyl, hetaryl, aryl, 3-10 membered heterocyclyl-C1-C5-alkyl, C3-C 10 -Cycloalkyl-C1-C5-alkyl, C3-C 10 -cycloalkenyl-C1-C5-alkyl, hetaryl-C1-C5-alkyl, or aryl-C1-C5-alkyl, the cyclic moiety being unsubstituted or substituted by one or more of the same or different substituents R y is replaced by; A is a 3- to 12-membered non-aromatic carbocyclic or heterocyclic ring, the heterocyclic ring containing one or more of the same or different heteroatoms N, O, or S, which may be oxidized, and the carbocyclic or heterocyclic ring is unsubstituted or contains one or more of the same or different substituents R j and / or R l is replaced by; D is a direct bond, C1-C6-alkylene, C2-C6-alkenylene, or C2-C6-alkynylene, and the carbon chain is unsubstituted or has one or more of the same or different substituents R n is replaced by; E is a non-aromatic 3- to 12-membered carbocyclic or heterocyclic ring, the heterocyclic ring containing one or more of the same or different heteroatoms N, O, or S, which may be oxidized, and the carbocyclic or heterocyclic ring is unsubstituted or contains one or more of the same or different substituents R n and / or R l is replaced by; R 4d is C1-C4-haloalkyl or C3-C6-cycloalkyl, each of which may be halogenated; G is C1-C6-alkylene, C2-C6-alkenylene, C2-C6-alkynylene, C3-C6-cycloalkylene or C3-C6-cycloalkenylene, the C atoms being unsubstituted or substituted with one or more identical or different substituents R p is replaced by; or R 4 teeth, (iv) any one of the following groups:
[0311] [ka] R 4e is H, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, or a 3- to 6-membered heterocycle, which heterocycle contains one or more identical or different heteroatoms N, O, or S, which S may be oxidized, and which group is unsubstituted or contains one or more identical or different substituents Rr and / or R l is replaced by; Q is a direct bond, C1-C8-alkylene, C2-C8-alkenylene, or C2-C8-alkynylene, and the carbon chain is unsubstituted or has one or more of the same or different substituents R r is substituted with; or Q and R 4e together with the imidazole form a 3- to 6-membered carbocyclic ring or a 4- to 6-membered heterocyclic ring having a direct bond, the heterocyclic ring containing one or more of the same or different heteroatoms N, O, or S, which may be oxidized, and the ring is unsubstituted or contains one or more of the same or different substituents R r and / or R l is replaced by; M is O, S, NR M , NOR M , or NSR M and; R M is R 4e or R M and Q together form a 4-6 membered unsaturated, non-aromatic N-containing heterocycle, which may contain additional heteroatoms O or S, which may be oxidized, and which may be unsubstituted or may contain one or more of the same or different substituents R r is replaced by; R 4g is H, C1-C6-alkyl, C1-C6-alkyl-X, C3-C6-cycloalkyl, or C3-C6-cycloalkyl-X; and R 4f is C1-C6-alkyl, C1-C6-alkyl-X, C3-C6-cycloalkyl or C3-C6-cycloalkyl-X; the C1-C6-alkyl or C3-C6-cycloalkyl group is unsubstituted or has one or more identical or different substituents R t is replaced by; X is O, S, NH or NR l is; or R 4g and R 4ftogether with the carbon atoms to which they are attached form a 3- to 8-membered, saturated or unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which carbocyclic or heterocyclic ring is unsubstituted or contains one or more of the same or different substituents R t and / or R l is replaced by; W is C1-C8-alkylene, C3-C8-cycloalkylene, C3-C8-heterocycloalkylene, C2-C8-alkenylene, C3-C8-cycloalkenylene, C3-C8-heterocycloalkenylene, or C2-C8-alkynylene, and W is unsubstituted or substituted with one or more of the same or different substituents R t and / or R l is replaced by; V is O, S or NR 1a and R 1a H, C1~C 10 -Alkyl, C1-C4-haloalkyl, C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkylmethyl, C3-C 10 -Halocycloalkyl, C2-C 10 -Alkenyl, C2-C 10 -Haloalkenyl, C2-C 10 -Alkynyl, C1-C 10 -alkoxy-C1-C4-alkyl, OR a , 3- to 10-membered heterocyclyl, 3- to 10-membered heterocyclyl-C1-C4-alkyl, aryl, hetaryl, aryl-C1-C4-alkyl, or hetaryl-C1-C4-alkyl, and the cyclic moiety is unsubstituted or has one or more of the same or different substituents R aa is substituted with; or R 1a and R 4g is R 4g and the carbon atom to which R is bonded 1ais bonded to the nitrogen atom and the nitrogen atom between the carbon atom and the nitrogen atom to form a 4- to 8-membered heterocycle, the heterocycle containing two nitrogen atoms as heteroatoms and optionally containing one or more of the same or different heteroatoms N, O, or S, wherein S is optionally oxidized, and the heterocycle is unsubstituted or contains one or more of the same or different substituents R t and / or R l is replaced by; or R 4 teeth, (v)(va)S(O) m -R 4h , (vb) OR 4i , or (vc)NR 4j R 4k is one of the groups R 4h , R 4i are, independently of each other, CN; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic group being unsubstituted or having one or more identical or different substituents R A1 is replaced by; C3-C8-cycloalkyl, C5-C8-cycloalkenyl, or 3- to 8-membered heterocyclyl, wherein the heterocyclyl group contains one or more of the same or different heteroatoms O, N, S(O) m or NR 3A The cyclic group contains one or more of the same or different C(G A )R 2A The cyclic group may be unsubstituted or may contain one or more of the same or different substituents R A4 is replaced by; C3-C8-cycloalkyl-C1-C4-alkyl, C5-C8-cycloalkenyl-C1-C4-alkyl or 3-8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 3A The cyclic group contains one or more of the same or different C(G A )R 2Agroups, the C atoms of which may be unsubstituted or may be substituted with one or more of the same or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A5 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A6 is replaced by; G A is O, N-CN, or N-OR 2A and; R 2A is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C5-C8-cycloalkenyl, or 3- to 8-membered heterocyclyl, wherein the heterocyclyl group contains one or more of the same or different heteroatoms O or S(O) m The cyclic group may be unsubstituted or may contain one or more of the same or different substituents R A4 is replaced by; C3-C8-cycloalkyl-C1-C4-alkyl, C5-C8-cycloalkenyl-C1-C4-alkyl or 3-8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is selected from the group consisting of one or more of the same or different heteroatoms O or S(O) m and the C atoms of these groups are unsubstituted or are substituted with one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A6 is replaced by; R 3A is H; C1-C6-alkyl, C3-C6-alkenyl, or C3-C6-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more of the same or different substituents R A3 is substituted with; or CONR 2A R 4A or COR 2A and; R 4A is H; C1-C6-alkyl, C3-C6-alkenyl, or C3-C6-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; and R 4j is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is substituted with; or C(O)R 2B , C(O)NR 3B R 4B , C(O)OR 5B , SO2R 6B and; R 4k is H;NR 3aB R 4aB ; C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, or C1-C4-alkoxy, the aliphatic group being unsubstituted or having one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 4aB and the cyclic group may contain one or more CO groups, the C atoms of which are unsubstituted or substituted by one or more of the same or different substituents R A4 is substituted with; or Aryl, aryl-C1-C4-alkyl, hetaryl or hetaryl-C1-C4-alkyl, the C atoms of these groups are unsubstituted or substituted with one or more identical or different substituents R A6 is substituted with; or R 4j and R 4k together with the nitrogen atom to which they are attached form a 3- to 7-membered heterocycle, which contains a nitrogen atom as a heteroatom and one or more of the same or different heteroatoms O, N, S(O) m or N, and the ring may be unsubstituted or may contain one or more of the same or different substituents R A8 is replaced by; R 2B , R 3B , R 4B are, independently of one another, H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or contain one or more identical or different substituents R A6is replaced by; R 3aB is H; C1-C8-alkyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or contain one or more identical or different substituents R A6 is replaced by; R 4aB is H; C1-C4-alkyl, the aliphatic groups of which are unsubstituted or substituted with one or more identical or different substituents selected from halogen or C1-C4-alkoxy; C3-C6-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is substituted with; or C(O)R 2B , C(O)OR 5B , or SO2R 6B and R 5B is C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic groups of which are unsubstituted or substituted with one or more, identical or different, substituents selected from halogen or C1-C4-alkoxy; or C3-C6-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is replaced by; R 6B is C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic group being unsubstituted or having one or more identical or different substituents RA3 is replaced by; C3-C6-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is substituted with; or aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is replaced by; or R 4 teeth, (vi)(via)C(T 1 )R 4l , (vib)C(O)OR 4m , (vic)C(Y)NR 4n R 4o , or (vid)C(Y)NR 4p NR 4q R 4r is one of the groups R 4l is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl or 3- to 8-membered heterocyclyl, the heterocyclyl group containing one or more of the same or different heteroatoms O or S(O) m The cyclic group may be unsubstituted or may contain one or more of the same or different substituents R A4 is replaced by; C3-C8-cycloalkyl-C1-C4-alkyl or 3-8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group contains one or more of the same or different heteroatoms O or S(O) m and the C atoms of these groups are unsubstituted or are substituted with one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A6 is replaced by; and T 1 O, N-OR 1C , N-NR 2C R 3C , or
[0312] [ka] and # is C(T 1 )R 4l Group C(T 1 ) moiety with a carbon atom; L A and L B are independently O or S(O) m and; A 1 is C2-C4-alkylene, the C atoms are unsubstituted or substituted with one or more identical or different substituents R 4C is replaced by; and R 1C is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is replaced by; C-C-cycloalkyl-C-C-alkyl, the C atoms of these groups are unsubstituted or substituted by one or more identical or different substituents R A4 is replaced by; aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A6 is replaced by; R 2C is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which groups are unsubstituted or have one or more identical or different substituents R A4 is replaced by; R 3C is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 3A and the cyclic group may contain one or more CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 4C is halogen; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; aryl, which groups are unsubstituted or have one or more of the same or different substituents R A6 is substituted with; or Two Rs attached to the same carbon atom4C form a C2-C4-alkylene chain, which is unsubstituted or has one or more identical or different substituents R A4 is substituted with; or Two Rs attached to the same carbon atom 4C forms a C1-C4-alkenylene chain, the double bond of which is attached to said carbon atom, and which chain is unsubstituted or has one or more of the same or different substituents R A4 is replaced by; R 4m is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A4 is replaced by; C-C-cycloalkyl-C-C-alkyl, the C atoms of these groups are unsubstituted or substituted by one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A6 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A6 is replaced by; R 4n is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C1-C4-alkylsulfonyl, C3-C6-cycloalkylsulfonyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl, which groups are unsubstituted or have one or more identical or different substituents RA4 is substituted with; or phenyl-C1-C2-alkoxycarbonyl, the C atoms of these groups are unsubstituted or substituted with one or more identical or different substituents R A6 is replaced by; R 4o is H; C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C4-alkoxy, the aliphatic radicals being unsubstituted or having one or more identical or different substituents R A2 is replaced by; C3-C8-cycloalkyl or 3- to 8-membered heterocyclyl, the heterocyclyl group containing one or more of the same or different heteroatoms O, N, S(O) m or NR 3A and the cyclic group may contain one or more CO groups, and the cyclic group may be unsubstituted or may contain one or more of the same or different substituents R A4 is replaced by; C3-C8-cycloalkyl-C1-C4-alkyl or 3-8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 4A and the cyclic group may contain one or more CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more identical or different substituents R A7 is substituted with; or aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the C atoms of these groups being unsubstituted or substituted by one or more identical or different substituents R A7 is substituted with; or R 4n and R 4otogether with the nitrogen atom to which they are attached form a 3- to 8-membered heterocycle, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which is unsubstituted or contains one or more of the same or different substituents R A4 is replaced by; R 4p is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which groups are unsubstituted or have one or more identical or different substituents R A4 is replaced by; R 4q is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-C1-C4-alkyl or aryl-C1-C4-alkoxy, which groups are unsubstituted or have one or more identical or different substituents R A4 is replaced by; R 4r is H; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m or NR 3Aand the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; or R 4 teeth, (vii)R 4s and R 4s is aryl or hetaryl, the cyclic group of which is unsubstituted or has one or more of the same or different substituents R 1D is replaced by; R 1D CN, NO2, halogen, NR 2D R 3D ;C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-S(O) m -, C1-C4-haloalkyl-S(O) m -, carboxy; or aryl, or hetaryl, which groups are unsubstituted or contain one or more of the same or different substituents R A6 is substituted with; or Two adjacent R 1D Groups, taken together with the adjacent atoms to which they are attached, form a fused 3- to 8-membered heterocyclic ring, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which are unsubstituted or contain one or more of the same or different substituents R A6 is replaced by; R 2D is H; C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, which groups are unsubstituted or contain one or more identical or different substituents R A3 or RA4 is replaced by; R 3D is H; C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, which groups are unsubstituted or contain one or more identical or different substituents R A3 or R A4 is substituted with; or R 2D and R 3D together with the nitrogen atom to which they are attached form a 3- to 8-membered heterocycle, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which is unsubstituted or contains one or more of the same or different substituents R A6 is replaced by; or R 4 teeth, (viii)CR 4t R 4u R 4v and R 4t is H; CN; C1-C8-alkyl, C2-C8-alkenyl, or C2-C8-alkynyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl or 3- to 8-membered heterocyclyl, wherein the heterocyclyl group contains one or more of the same or different heteroatoms O, N, S(O) m or NR 1Fand the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 4u is H; C1-C4-alkyl, the aliphatic radicals being unsubstituted or substituted with one or more identical or different substituents R A3 is substituted with; or R 4t and R 4u together with the carbon atoms to which they are attached form a 3- to 8-membered carbocyclic or heterocyclic ring, which heterocyclic ring may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F wherein the cyclic group may contain one or more of the same or different CO groups, and the carbocyclic or heterocyclic ring may be unsubstituted or may contain one or more of the same or different substituents R A3 is substituted with; or R 4t and R 4u are both C2-C6-alkenyl, the aliphatic groups of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; R 4v is H;S(O) m R 1E , OR 2E , or N(R 3E )(R 4E ) and R 4t and / or R 4u is H or C1-C8-alkyl, the aliphatic group may be unsubstituted or may contain one or more of the same or different substituents R A3 is substituted with R 4v is S(O) m R 1E , OR 2E , or N(R3E )(R 4E ) and; R 1E is C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic group being unsubstituted or containing one or more identical or different substituents R A9 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 2E is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A9 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 3E is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 4E is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is substituted with; or C(O)N(R 5E )(R 6E ), C(O)R 7E , C(O)OR 8E , or SO2R 9E is; or R 3E and R 4E together with the nitrogen atom to which they are attached form a 3- to 9-membered heterocycle, the heterocyclyl group of which may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A8 is substituted with; or R 5E and R 6Eare, independently of one another, H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl or 3- to 8-membered heterocyclyl, wherein the heterocyclyl group contains one or more of the same or different heteroatoms O, N, S(O) m or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is substituted with; or R 5E and R 6E together with the nitrogen atom to which they are attached form a 3- to 8-membered heterocyclic ring, which heterocyclic ring may contain one or more of the same or different heteroatoms O, or S(O) m and the heterocycle is unsubstituted or contains one or more of the same or different substituents R A10 is replaced by; R 7E is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A3is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 8E is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1Fand the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 9E is C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic group being unsubstituted or containing one or more identical or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group is substituted with one or more of the same or different heteroatoms O, N, S(O) m , or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is replaced by; C5-C8-cycloalkenyl, C5-C8-cycloalkenyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl group may contain one or more of the same or different heteroatoms O, N, S(O) m, or NR 1F and the cyclic group may contain one or more identical or different CO groups, the C atoms of which are unsubstituted or substituted with one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; R 1F is H; C1-C8-alkyl, C3-C8-alkenyl, or C3-C8-alkynyl, the aliphatic radicals of which are unsubstituted or substituted with one or more of the same or different substituents R A3 is replaced by; C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-C1-C4-alkyl, the C atoms of these groups are unsubstituted or are substituted by one or more identical or different substituents R A4 is substituted with; or aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, which groups are unsubstituted or have one or more identical or different substituents R A6 is replaced by; and R a , R b , R care, independently from one another, H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6-cycloalkenylmethyl, C3-C6-halocycloalkenyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, 3- to 6-membered heterocyclyl, 3- to 6-membered heterocyclyl-C1-C4-alkyl, aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, and the cyclic moiety is unsubstituted or is substituted by one or more identical or different substituents R aa is replaced by R d is H, C1-C4-alkoxy, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6-cycloalkenylmethyl, C3-C6-halocycloalkenyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, 3- to 6-membered heterocyclyl, 3- to 6-membered heterocyclyl-C1-C4-alkyl, aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the cyclic moiety of which is unsubstituted or is substituted by one or more of the same or different substituents R aa is replaced by; R e , R fare, independently of one another, H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6-cycloalkenylmethyl, C3-C6-halocycloalkenyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, 3- to 6-membered heterocyclo aryl, 3- to 6-membered heterocyclyl-C1-C4-alkyl, 3- to 6-membered heterocyclylcarbonyl, 3- to 6-membered heterocyclyl-C1-C4-alkyl-carbonyl, 3- to 6-membered heterocyclyl-C1-C4-alkyl-sulfonyl, aryl, arylcarbonyl, aryl-C1-C4-alkyl-carbonyl, arylsulfonyl, hetaryl, hetaryl-C1-C4-alkyl-carbonyl, hetarylcarbonyl, hetarylsulfonyl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, the cyclic moiety of which is unsubstituted or is substituted by one or more of the same or different substituents R aa is substituted with; or R e and R f together with the nitrogen atom to which they are attached form a 5- or 6-membered, saturated or unsaturated heterocycle, which may further contain heteroatoms O, S, or N, where S may be oxidized, and which may be unsubstituted or may contain one or more of the same or different substituents R aa is replaced by; R g , R hare, independently from one another, H, C1-C4-alkyl, C1-C4-haloalkyl, L-C3-C6-cycloalkyl, L-C3-C6-halocycloalkyl, L-C3-C6-cycloalkenyl, L-C3-C6-halocycloalkenyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, 3- to 6-membered heterocyclyl, 3- to 6-membered heterocyclyl-C1-C4-alkyl, aryl, hetaryl, aryl-C1-C4-alkyl or hetaryl-C1-C4-alkyl, and the cyclic moiety is unsubstituted or is substituted by one or more identical or different substituents R aa is replaced by; R i is H, CN, C1-C4-alkyl, C1-C4-haloalkyl, L-C3-C6-cycloalkyl, L-C3-C6-halocycloalkyl, L-C3-C6-cycloalkenyl, L-C3-C6-halocycloalkenyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, aryl or aryl-C1-C4-alkyl, the aryl ring being unsubstituted or containing one or more identical or different substituents R aa is replaced by; R bonded to C j are halogens, OH, CN, NO2, C1-C 10 -Alkyl, C1-C 10 -Haloalkyl, C1-C 10 -Alkoxy, C1-C 10 -haloalkoxy, S(O) m R k , C3-C6-cycloalkyl, or a 3- to 6-membered heterocycle, which heterocycle contains one or more of the same or different heteroatoms N, O, or S, where S may be oxidized; R j The group may be unsubstituted or may contain one or more of the same or different substituents R m and / or R l and two R attached to the same or adjacent ring atoms jThe groups together can form a 3- to 6-membered carbocyclic or heterocyclic ring, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which ring is unsubstituted or contains one or more of the same or different substituents R m and / or R l is replaced by; R k is H, C1-C4-alkyl, C1-C4-haloalkyl, or C3-C6-cycloalkyl, the ring being unsubstituted or containing one or more identical or different substituents R l is replaced by; R bonded to N l is C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, or C1-C4-alkoxycarbonyl; R bonded to C m is halogen, OH, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, or S(O) m R k and; R bonded to C n is halogen, CN, NO2, C1-C2-alkyl, C1-C4-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylidene, =O, =S, =NR 1o , =NOR 1o , =NSR 1o , or S(O) m R 1o or two adjacent R n The groups, together with the atoms to which they are attached, form a 3- to 8-membered carbocyclic or heterocyclic ring, which heterocyclic ring contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and the R n The moiety may be unsubstituted or may contain one or more of the same or different substituents halogen, R o , and / or Rl is replaced by; R 1o is H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, or C1-C4-alkoxy; R bonded to C o is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, or C1-C4-alkoxycarbonyl; R p is halogen, CN, NO, C-C-alkyl, C-C-haloalkyl, C-C-cycloalkyl, C-C-alkoxy or C-C-haloalkoxy, or two R p The groups together can form a 3- to 6-membered carbocyclic or heterocyclic ring, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which carbocyclic or heterocyclic ring is unsubstituted or contains one or more of the same or different substituents R q is replaced by; R q is halogen, CN, NO, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy, R bonded to C r is halogen, CN, NO2, C1-C2-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C2-haloalkoxy, or S(O) m R k or two R r The groups together form a 3- to 6-membered carbocyclic or heterocyclic ring, which contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and which carbocyclic or heterocyclic ring is unsubstituted or s is replaced by; R sis halogen, CN, NO2, C1-C2-alkyl, C1-C2-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy or C1-C2-haloalkoxy, R bonded to C t is halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-halocycloalkyl, C3-C6-halocycloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, S(O) m R w , =O, =S, =NR v , =NOR v , or =NSR v or two R attached to the same carbon atom or adjacent carbon atoms t together with the carbon atoms to which they are attached form a 3- to 6-membered, saturated or unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring contains one or more of the same or different heteroatoms N, O, or S, which S may be oxidized, and N may be unsubstituted or may be substituted with one or more of the same or different substituents R l is replaced by; R v is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, or C3-C6-halocycloalkyl; R w is H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy, R x is halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, S(O) m R d , S(O) m NR e R f , N.R. e R f , C(O)NR g R h , C1~C10 -alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C3-C6-cycloalkyl, 5- to 7-membered heterocyclyl, 5- or 6-membered hetaryl, aryl, C3-C6-cycloalkoxy, 3- to 6-membered heterocyclyloxy, or phenoxy, and the cyclic moiety is unsubstituted or substituted by one or more of the same or different substituents R y is replaced by; R y is halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, S(O) m R d , S(O) m NR e R f , C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, or C1-C4-alkoxy-C1-C4-alkyl; R aa is halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; R A1 is CN, halogen, C1-C4-alkoxy, C1-C4-alkyl-S(O) m -, C(O)R 2A , C(O)NR 2A R 3A , or C(G A )R 2A and; R A2 is CN, halogen, OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl, or C1-C4-alkyl-S(O) m - and; R A3 is CN, halogen, C1-C4-alkoxy, or C1-C4-alkyl-S(O) m- and; R A4 is CN, halogen, C1-C4-alkyl, C1-C4-haloalkyl, or C1-C4-alkoxy; R A5 is CN, NO2, halogen, oxime ether, acyl amide, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-S(O) m -, C1-C4-haloalkyl-S(O) m -or aryl, aryloxy, hetaryl, or hetaryloxy, and the aromatic group is unsubstituted or has one or more of the same or different substituents R Z1 is replaced by; R Z1 is CN, NO2, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-S(O) m -, C1-C4-haloalkyl-S(O) m -, hetaryloxy, or aryloxy; R A6 is CN, NO2, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-S(O) m - or C1-C4-haloalkyl-S(O) m - and; R A7 is CN, NO2, halogen, C1-C4-alkyl, C1-C4-haloalkyl, OH, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-S(O) m - or C1-C4-haloalkyl-S(O) m - and; R A8is H, CN, NO2, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C5-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-halocycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, cyano-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C1-C4-alkyl-S(O) m -, C1-C4-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, di-(C1-C6)-alkylaminocarbonyl, C1-C6-alkylcarbonylamino, aryl or hetaryl, the aryl or hetaryl group being unsubstituted or having one or more identical or different substituents R Z2 is replaced by; R Z2 is CN, NO2, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C6-haloalkoxy, or C1-C4-alkylthio; R A9 is CN, halogen, C1-C4-alkoxy, C1-C4-alkyl-S(O) m -, C(O)OR 2A , C(O)NR 2A R 3A , or C(G A )R 2A and; R A10 is C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy; Y is O or S; m is 0, 1 or 2. Item 6. The pesticide composition according to any one of Items 1 to 5, wherein the compound is:
[0313] Section 7: R P1 , R P2 , R P3Item 7. The pesticide composition according to Item 6, wherein: is H and T is O.
[0314] Section 8: R 1 is H, C1-C2-alkyl, C3-C5-cycloalkyl, or C1-C2-alkoxy-C1-C2-alkyl; R 2 is C1-C6-alkyl or C1-C6-haloalkyl; R 3 is H, C1-C2-alkyl, or C1-C2-haloalkyl Item 6. The pesticide composition according to Item 6 or 7.
[0315] Section 9: Item 9. The pesticide composition according to any one of items 6 to 8, wherein the active ingredient is a compound of formula IA.
[0316] [ka]
[0317] Section 10: Item 9. The pesticide composition according to any one of items 6 to 8, wherein the active ingredient is a compound of formula (IB).
[0318] [ka]
[0319] Section 11: Z 1 and Z 2 is N and Z 3 Item 11. The pesticide composition according to any one of items 6 to 10, wherein is CH.
[0320] Section 12: Z 1 is CH and Z 3 is N and Z 2 is CR 4 Item 11. The pesticide composition according to any one of Items 6 to 10, wherein
[0321] Section 13: Item 13. The pesticide composition according to any one of items 1 to 12, wherein the active ingredient is present in a concentration of 1 to 65 wt% and the ethoxylated ricinolein is present in a concentration of 1 to 30 wt%, based on the total weight of the composition.
[0322] Section 14: Item 14. The pesticide composition according to any one of items 1 to 13, further comprising a second active ingredient.
[0323] Advantages: The pesticide composition is characterized by very high storage stability, low particle growth, reduced sedimentation, reduced gelation, favorable rheological profile, and high biological efficacy. The term "stability," as used herein, typically refers to the physical stability of the pesticide formulation. Thus, the term "stabilizing" typically refers to physical stabilization (e.g., increased storage stability).
[0324] The following examples illustrate the invention.
[0325] [Example] The following ingredients were used to prepare the pesticide compositions of the examples:
[0326] Insecticide A: 1-[(1RS)-1,2-dimethylpropyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-1H-pyrazole-4-carboxamide (CAS Registry Number 1403615-77-9). Dispersant: Lignin sulfonate, organic sulfur content approximately 9 wt% Antifoam: Emulsion of dimethylsiloxane on silica particles, defoamer content 20wt% Biocide A: Glycol-based solution of benzisothiazolinone Biocide B: Aqueous Composition of Benzisothiazolinone and 5-Chloro-2-methylisothiazolin-3-one Stabilizer: Hydrophobic fumed silica particles, surface modified with dimethylsilyl groups, water solubility less than 0.1 g / l, BET surface area 90-130 m 2 / g, carbon content 0.6~1.2wt% Wet A: C8~C 10 -Alkyl polyglycoside surfactant, HLB 13.6 Wet B: Sodium salt of naphthalene sulfonate condensate Wet C: Ethoxylated castor oil, with an average of 40 polymerized ethylene oxide units per molecule, saponification value 58-66 (according to ISO 3657) Wet D: Ethoxylated castor oil, with an average of 20 ethylene oxide units polymerized per molecule Wet E: Ethoxylated castor oil, with an average of 25 ethylene oxide units polymerized per molecule. Wet G: Ethoxylated castor oil, with an average of 35 ethylene oxide units polymerized per molecule. Wet H: Ethoxylated castor oil, with an average of 54 ethylene oxide units polymerized per molecule Wet J: Naphthalene sulfonate condensate, polymer with formaldehyde, ammonium salt. Wet K: 33 wt% methyl methacrylate, reaction product of methacrylic acid and methoxypolyethylene glycol methacrylate, 33 wt% propylene glycol, 33 wt% water. Wet L: Tristyrylphenol ethoxylate, polymerized with an average of 10 ethylene oxide units per molecule Wet M: Ethoxylated isotridecyl alcohol, average of 5 ethylene oxide units per molecule, HLB 10.5 Wet N: Lignin, reaction products of alkali with formaldehyde and sodium bisulfite Wet O: Aqueous mixture of 20 wt% ethoxylated tristyrylphenol, 20 wt% polyoxyethylene tristyrylphenol phosphate, potassium salt Wet P: Alkoxylated castor oil. pH adjuster: tetrahydroxypropylethylenediamine
[0327] [Example 1] Suspension concentrates SC-1 to SC-10 were prepared containing ingredients according to Table A. The suspension concentrates differed from one another by the type of wetting agent used, as presented in Table B.
[0328] The suspension concentrate was prepared by adding insecticide A, wetting agent, dispersant, antifoaming agent, biocide A, biocide B, acetic acid, and stabilizer to water. The mixture was homogenized until uniform and then milled in a bead mill until an average particle size of 2-3 μm was achieved.
[0329] The suspension concentrates were then placed in a 20°C / 40°C cycling chamber for two weeks (24 hours at 20°C, then 24 hours at 40°C) after which they were analyzed by visual inspection and testing of rheological properties. SC-3 was the only suspension concentrate that remained flowable; all other suspension concentrates, SC-1, SC-2, and SC-4 through SC-10, exhibited gelation.
[0330] [Table 1]
[0331] [Table 2]
[0332] [Example 2] Suspension concentrates SC-11 to SC-15 were prepared containing ingredients according to Table C. The suspension concentrates differed from one another by the type of wetting agent used, as presented in Table D.
[0333] The suspension concentrate was prepared in the first step by adding insecticide A, 20% of the allotted wetting agent, dispersing agent, antifoam agent, biocide A, biocide B, glycerol, pH adjuster, and stabilizer to water to create a grind base. In the second step, the grind base was homogenized until uniform and then milled in a bead mill until an average particle size of 2-3 microns was achieved. In the third step, the resulting composition was mixed with the remaining wetting agent until uniform.
[0334] Suspension concentrates SC-11 and SC-12 showed gelation already during milling. SC-11 through SC-15 were then incubated at 22°C for 24 hours, after which the suspension concentrates were analyzed by visual inspection and rheological property testing. SC-11, SC-12, and SC-15 showed gelation. SC-13 remained slightly flowable, and SC-14 remained completely flowable.
[0335] [Table 3]
[0336] [Table 4] The present invention includes, for example, the following embodiments. [Section 1] a) suspended particles of ginpropylidazol; and b) ethoxylated ricinolein; Including, An aqueous pesticide composition wherein the ethoxylated ricinolein contains, in polymerized form, 35 to 50 ethylene oxide molecules per ricinolein molecule. [Section 2] Item 1. The pesticide composition according to Item 1, wherein the ethoxylated ricinolein contains 38 to 42 ethylene oxide molecules per ricinolein molecule in polymerized form. [Section 3] Item 3. The pesticide composition according to Item 1 or 2, wherein the suspended particles have a median diameter of 0.5 μm to 20 μm. [Section 4] Item 4. The pesticide composition according to any one of Items 1 to 3, comprising dinpropylidaz at a concentration of 1 to 65 wt % based on the total weight of the pesticide composition. [Section 5] Item 5. The pesticide composition according to any one of items 1 to 4, comprising ethoxylated ricinolein at a concentration of 1 to 30 wt% based on the total weight of the pesticide composition. [Section 6] Item 6. The pesticide composition according to any one of items 1 to 5, further comprising a second active ingredient. [Section 7] Item 7. The pesticide composition according to any one of items 1 to 6, having a weight ratio of dinpropylidaz to ethoxylated ricinolein of 1:1 to 100:1. [Section 8] A method for stabilizing an aqueous pesticide composition containing suspended particles of dinpropylidaz, comprising contacting the ethoxylated ricinolein described in any one of Items 1 to 7 with particles of dinpropylidaz described in any one of Items 1 to 7 and water. [Section 9] A method for treating, controlling, preventing, or protecting an animal against infestation or infection by a parasite, by orally, topically, or parenterally administering or applying the pesticide composition according to any one of Items 1 to 7 to the animal. [Section 10] 10. A method for controlling invertebrate pests, infestations, or infestations by invertebrate pests, comprising contacting the pests, their food supply, habitat, breeding grounds, or their location with a pesticidally effective amount of the pesticide composition of any one of paragraphs 1 to 7. [Section 11] 8. Use of the pesticide composition of any one of paragraphs 1 to 7 to protect growing plants or plant propagation material from attack or infestation by invertebrate pests. [Section 12] A method for preparing the pesticide composition according to any one of Items 1 to 7, comprising contacting the ethoxylated ricinolein according to any one of Items 1 to 7 with the dinpropylidaz according to any one of Items 1 to 7 in the presence of water. [Section 13] Item 8. A plant propagation material comprising the pesticide composition according to any one of items 1 to 7.
Claims
1. a) suspended particles of ginpropylidazol; and b) ethoxylated ricinolein; Including, 1. An aqueous pesticide composition, wherein the ethoxylated ricinolein in polymerized form contains 38 to 42 ethylene oxide molecules per ricinolein molecule, Contains dinpropylidaz at a concentration of 1 to 65 wt% based on the total weight of the pesticide composition; An aqueous pesticide composition comprising ethoxylated ricinolein at a concentration of 1 to 30 wt %, based on the total weight of the pesticide composition.
2. 2. The pesticide composition of claim 1, wherein the suspended particles have a median diameter of 0.5 μm to 20 μm.
3. 3. The pesticide composition according to claim 1, further comprising a second active ingredient.
4. 4. The pesticide composition according to any one of claims 1 to 3, having a weight ratio of dinpropylidaz to ethoxylated ricinolein of from 1:1 to 100:
1.
5. 1. A method for stabilizing an aqueous pesticide composition containing suspended particles of dinpropylidaz, comprising contacting ethoxylated ricinolein with particles of dinpropylidaz and water, Ethoxylated ricinolein contains, in polymerized form, 38 to 42 ethylene oxide molecules per ricinolein molecule; The pesticide composition contains dinpropylidaz at a concentration of 1 to 65 wt % based on the total weight of the pesticide composition; The method, wherein the pesticide composition contains ethoxylated ricinolein at a concentration of 1 to 30 wt %, based on the total weight of the pesticide composition.
6. 10. A method for treating, controlling, preventing or protecting animals (excluding humans) against infestation or infection by parasites by administering or applying the pesticide composition according to any one of claims 1 to 4 orally, topically or parenterally to the animals.
7. 10. A method for controlling invertebrate pests, infestations, or infestations by invertebrate pests (excluding methods for treating humans) comprising contacting the pests, their food supply, habitat, breeding grounds, or their location with a pesticidally effective amount of the pesticide composition of any one of claims 1 to 4.
8. 5. Use of the pesticide composition according to any one of claims 1 to 4 for protecting growing plants or plant propagation material from attack or infestation by invertebrate pests.
9. A method for preparing the pesticide composition described in any one of claims 1 to 4, comprising a step of contacting ethoxylated ricinolein, which in polymerized form contains 38 to 42 ethylene oxide molecules per ricinolein molecule, with dinpropylidaz in the presence of water.
10. 5. Plant propagation material comprising the pesticide composition of any one of claims 1 to 4.
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