2-(HET)ARYL-SUBSTITUTED FUSED BICYCLIC HETEROCYCLENE DERIVATIVES AS PESTICIDES

Description

[0001] The present invention relates to novel 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives of formula (I), their use as acaricides and / or insecticides for controlling animal pests, especially arthropods and in particular insects and arachnids, and processes and intermediates for their preparation.

[0002] 2-(Het)Aryl-substituted condensed bicyclic heterocycle derivatives with insecticidal properties have already been described in the literature, e.g. in WO 2010 / 125985, WO 2012 / 074135, WO 2012 / 086848, WO 2013 / 018928, WO 2014 / 142292 and WO 2014 / 148451, as well as WO 2015 / 000715, WO 2015 / 121136 and WO 2015 / 002211.

[0003] However, the active substances already known from the above-mentioned documents have some disadvantages in their application, either because they have only a limited range of applications or because they do not have a satisfactory insecticidal or acaricidal effect.

[0004] New 2-(het)aryl-substituted fused bicyclic heterocycle derivatives have now been discovered that offer advantages over previously known compounds, including better biological or ecological properties, broader application methods, improved insecticidal and acaricidal activity, and good tolerance by crops. The 2-(het)aryl-substituted fused bicyclic heterocycle derivatives can be used in combination with other agents to improve efficacy, particularly against difficult-to-control insects.

[0005] The present invention therefore relates to novel compounds of formula (I) where the substituents R 1< , R 2a< , R 2b< , R 3< , A 1< , A 2< , A 4< and n have the meanings given in the following table:

[0006] Furthermore, the invention relates to compounds of the following formulas (IX), (XI) and (XII), in which R 1< , R 2a< , R 3< , A 1< , A 2< and A 4< have the meanings given above and X1 and X2 respectively represent halogen.

[0007] In the preferred definitions, unless otherwise stated, halogen is selected from the series fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,

[0008] Depending on the nature of the substituents, the compounds of formula (I) can exist as geometric and / or optically active isomers or corresponding isomer mixtures in varying compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers, or geometric isomers. The invention thus encompasses pure stereoisomers as well as any mixtures of these isomers.

[0009] Compounds 1-74 of formula (I) can be obtained by the processes shown in the following schemes (Examples 1-30 are according to the invention and Examples 31-74 are comparative examples): Procedure A

[0010]

[0011] The radicals R 1< , R 2a< , R 3< , R 11< , R 12< , A 1< , A 2< , A 4< and n have the meanings described above and X 1< stands for halogen and V for (C 1 -C 4 )alkyl. Step a)

[0012] The compounds of formula (IV) can be prepared analogously to the process described in US5576335 by reacting compounds of formula (II) with carboxylic acids of formula (III) in the presence of a condensing agent.

[0013] Compounds of formula (II) are either commercially available or can be prepared by known methods, for example analogously to the processes described in US2003 / 69257 or WO2006 / 65703.

[0014] Carboxylic acids of formula (III) are either commercially available or can be prepared by known methods, for example analogously to the processes described in US2010 / 234604, WO2012 / 61926 or Bioorganic and Medicinal Chemistry Letters, 18 (2008), 5023-5026.

[0015] The reaction of the compounds of formula (II) with carboxylic acids of formula (III) can be carried out in bulk or in a solvent; preferably, the reaction is carried out in a solvent selected from customary solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles such as, for example, acetonitrile or propionitrile; aromatic hydrocarbons such as, for example, toluene or xylene; aprotic polar solvents such as, for example, N,N-dimethylformamide or N-methylpyrrolidone; or nitrogen-containing compounds such as, for example, pyridine.

[0016] Suitable condensing agents are, for example, carbodiimides such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.

[0017] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 180 °C, preferably the reaction is carried out at atmospheric pressure and temperatures from 20 to 140 °C. Step b)

[0018] The compounds of formula (V) can be prepared by condensation of the compounds of formula (IV), e.g. analogously to the processes described in WO2012 / 86848.

[0019] The reaction to give compounds of formula (V) can be carried out in bulk or in a solvent; preferably, the reaction is carried out in a solvent selected from customary solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene; nitriles such as, for example, acetonitrile or propionitrile; aromatic hydrocarbons such as, for example, toluene or xylene; aprotic polar solvents such as, for example, N,N-dimethylformamide or N-methylpyrrolidone; or nitrogen-containing compounds such as, for example, pyridine.

[0020] The reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.

[0021] Examples of suitable condensing agents are carbodiimides such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azodiester such as diethylazodicarboxylic acid.

[0022] Examples of suitable acids that can be used in the described reaction are sulfonic acids such as para-toluenesulfonic acid; carboxylic acids such as acetic acid or polyphosphoric acids.

[0023] Examples of suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as triethylamine and N,N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.

[0024] An example of a suitable chlorinating agent is phosphorus oxychloride.

[0025] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 200 °C. Step c)

[0026] The compounds of formula (VI) can be prepared by halogenation of the compounds of formula (V), for example, analogously to the processes described in US Pat. No. 4,801,593. An example of a suitable halogenating agent is phosphorus oxychloride. All inert organic solvents, for example, aliphatic or aromatic hydrocarbons, can be used as solvents or diluents. Toluene is preferred.

[0027] In a further embodiment, the nitrogen (A 1< = N) adjacent to the halogenation position is first oxidized, e.g., analogously to the processes described in WO2008 / 112646. Examples of suitable oxidizing agents are meta-chloroperbenzoic acid or hydrogen peroxide. The reaction is preferably carried out in a solvent selected from customary solvents that are inert under the prevailing reaction conditions. Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, or esters such as ethyl acetate. The subsequent halogenation is carried out analogously to that described above using a suitable halogenating agent such as, for example, phosphorus oxychloride. Step d)

[0028] The compounds of formula (XIV) can be prepared by carbonylation of the compounds of formula (VI) analogously to SA Vinogradov, DF Wilson, Tetrahedron Letters 39 (1998), 8935-8938. The radical V is preferably methyl, ethyl, n-propyl, or n-butyl. Palladium phosphane complexes can be used as catalysts for reaction d), for example, a catalyst composed of palladium chloride, triphenylphosphane, and DPPP (1,3-bis(diphenylphosphino)propane) (1:1:1). Preferred bases are, for example, Hünig's base (diisopropylethylamine) or DBU (1,8-diazabicyclo(5.4.0)undec-7-ene). Steps e, f, g)

[0029] The ester of formula (XIV) can first be converted into the acid of formula (XV) using standard methods, cf. DE 2221647, for example with an alkali hydroxide as base such as sodium hydroxide or lithium hydroxide in an alcohol as solvent such as ethanol or a mixture of tetrahydrofuran and water.

[0030] The acid of formula (XV) is then converted into the acid chloride of formula (XVI) using standard methods, for example with a chlorinating reagent such as thionyl chloride or oxalyl chloride.

[0031] Further reaction with the amine of formula (XVII), in a diluent such as dichloromethane or tetrahydrofuran and in the presence of a base such as triethylamine or diisopropylethylamine, leads to compounds of formula (Ia) according to the invention (corresponds to formula I(Q3)).

[0032] Compounds of formula (XVII) are either commercially available or can be prepared by known methods. Step h)

[0033] Thioamides of formula (Ib) (corresponds to formula I(Q4)) can be prepared from the carbonamides of formula (Ia) by reaction with a sulfurizing reagent, for example Lawesson's reagent or P 4 S 10 . Procedure B

[0034]

[0035] The radicals R 1< , R 2a< , R 3< , A 1< , A 2< , A 4< and n have the meanings described above.

[0036] In a further embodiment of the invention, compounds of formula (V) can be prepared in a one-step process from the compounds of formula (II) with compounds of formula (III) in the presence of a condensing agent.

[0037] The reaction to give compounds of formula (V) can be carried out in bulk or in a solvent; preferably, the reaction is carried out in a solvent selected from customary solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such as methanol, ethanol or isopropanol; nitriles such as, for example, acetonitrile or propionitrile; aromatic hydrocarbons such as, for example, toluene or xylene; aprotic polar solvents such as, for example, N,N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as, for example, pyridine.

[0038] Examples of suitable condensing agents are carbodiimides such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azodiester such as diethylazodicarboxylic acid.

[0039] The reaction can be carried out in the presence of an acid or a base.

[0040] Examples of acids that can be used in the described reaction are sulfonic acids such as methanesulfonic acid or para-toluenesulfonic acid; carboxylic acids such as acetic acid or polyphosphoric acids.

[0041] Examples of suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as triethylamine and N,N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.

[0042] The reaction can be carried out in the presence of a suitable catalyst such as 1-hydroxybenzotriazole.

[0043] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 200 °C.

[0044] The further conversion of the compounds of formula (V) to compounds of formula (I) is carried out analogously to process A. Procedure C

[0045]

[0046] The radicals R 1< , R 2a< , R 2b< , R 3< , A 1< , A 2< and A 4< have the meanings described above and X 1< and X 2< respectively represent halogen. Step a)

[0047] The compounds of formula (VIII) can be prepared analogously to the process described in US5576335 by reacting compounds of formula (II) with a carboxylic acid of formula (VII) in the presence of a condensing agent or a base.

[0048] Compounds of formula (II) are either commercially available or can be prepared by known methods, for example analogously to the processes described in US2003 / 69257 or WO2006 / 65703.

[0049] Carboxylic acids of formula (VII) are either commercially available or can be prepared by known methods, for example analogously to the processes described in US2010 / 234604, WO2012 / 61926 or Bioorganic and Medicinal Chemistry Letters, 18 (2008), 5023-5026.

[0050] The reaction of the compounds of formula (II) with carboxylic acids of formula (VII) can be carried out in bulk or in a solvent; preferably, the reaction is carried out in a solvent selected from customary solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles such as, for example, acetonitrile or propionitrile; aromatic hydrocarbons such as, for example, toluene or xylene; aprotic polar solvents such as, for example, N,N-dimethylformamide or N-methylpyrrolidone; or nitrogen-containing compounds such as, for example, pyridine.

[0051] Suitable condensing agents are, for example, carbodiimides such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.

[0052] Suitable bases are inorganic bases commonly used in such reactions. Bases selected, for example, from the group consisting of acetates, phosphates, carbonates, and bicarbonates of alkali or alkaline earth metals are preferred. Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate.

[0053] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 180 °C, preferably the reaction is carried out at atmospheric pressure and temperatures from 20 to 140 °C. Step b)

[0054] The compounds of formula (IX) can be prepared by condensation of the intermediate compounds of formula (VIII), e.g. analogously to the processes described in WO2012 / 86848.

[0055] The reaction to give compounds of formula (IX) can be carried out in bulk or in a solvent; preferably, the reaction is carried out in a solvent selected from customary solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene; nitriles such as, for example, acetonitrile or propionitrile; aromatic hydrocarbons such as, for example, toluene or xylene; aprotic polar solvents such as, for example, N,N-dimethylformamide or N-methylpyrrolidone; or nitrogen-containing compounds such as, for example, pyridine.

[0056] The reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.

[0057] Examples of suitable condensing agents are carbodiimides such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azodiester such as diethylazodicarboxylic acid.

[0058] Examples of suitable acids that can be used in the described reaction are sulfonic acids such as para-toluenesulfonic acid; carboxylic acids such as acetic acid or polyphosphoric acids.

[0059] Examples of suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as triethylamine and N,N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.

[0060] An example of a suitable chlorinating agent is phosphorus oxychloride.

[0061] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 200 °C. Step c)

[0062] The compounds of formula (XI) can be prepared by reacting the compounds of formula (IX) with the compounds of formula (X) in the presence of a base.

[0063] Mercaptan derivatives of formula (X) such as methyl mercaptan, ethyl mercaptan or isopropyl mercaptan are either commercially available or can be prepared by known methods, for example analogously to the processes described in US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329.

[0064] The reaction to give compounds of formula (XI) can be carried out in bulk or in a solvent; preferably, the reaction is carried out in a solvent selected from conventional solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, and tert-butyl methyl ether; nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; and aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, or dimethyl sulfoxide.

[0065] Examples of suitable bases are inorganic bases from the group consisting of acetates, phosphates, and carbonates of alkali or alkaline earth metals. Preferred bases are cesium carbonate, sodium carbonate, and potassium carbonate. Other suitable bases are alkali metal hydrides such as sodium hydride.

[0066] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 200 °C. Step d)

[0067] The compounds of formula (XII) can be prepared by oxidation of the compounds of formula (XI). The oxidation is generally carried out in a solvent selected from among conventional solvents that are inert under the prevailing reaction conditions. Preferred solvents are halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid, propionic acid, or water.

[0068] Examples of suitable oxidizing agents are hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.

[0069] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from -20°C to 120°C. Step e)

[0070] The compounds of formula (XIII) can be prepared by oxidation of the compounds of formula (XII). The oxidation is generally carried out in a solvent. Preferred solvents are halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid, propionic acid, or water.

[0071] Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.

[0072] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from -20°C to 120°C. Step f)

[0073] The compounds of formula (XIII) can also be prepared in a one-step process by oxidation of the compounds of formula (XI). The oxidation is generally carried out in a solvent. Preferred solvents are halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid, propionic acid, or water.

[0074] Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.

[0075] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from -20°C to 120°C. Step g)

[0076] The further conversion of the compounds of formula (XIII) to compounds of formula (I) is carried out analogously to process A.

[0077] The compounds of formulas (XI) and (XII) can be converted into compounds of formula (I) analogously to process A. Procedure D

[0078]

[0079] The radicals R 1< , R 2a< , R 3< , R 8< , R 14< , R 15< , A 1< , A 2< , A 4< and n have the meanings described above and X 1< stands for halogen. Step a)

[0080] The compounds of formula (XVIII) can be prepared analogously to WO2015 / 002211 by reacting the compounds of formula (VI) with sodium azide.

[0081] The reaction to give compounds of formula (XVIII) is generally carried out in a solvent; preferably, the reaction is carried out in a solvent selected from among conventional solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, dioxane, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, or alcohols such as methanol or ethanol. Step b)

[0082] The compounds of formula (XIX) can be prepared by reduction of the intermediates of formula (XVIII), e.g. analogously to the processes described in WO2015 / 002211.

[0083] Examples of suitable reducing agents are triphenylphosphine, tributylphosphine, tin(III) chloride or zinc.

[0084] The reaction to form compounds of formula (XIX) is generally carried out in a solvent. Preferred solvents are ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, dioxane, aliphatic hydrocarbons such as hexane, heptane, aromatic hydrocarbons such as toluene, xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, or alcohols such as methanol or ethanol.

[0085] If necessary, an acid can be added to the reaction, such as hydrochloric acid or acetic acid. Step c)

[0086] The compounds of formula (XXI) can be prepared by reacting the compounds of formula (XIX) with a compound of formula (XX) in the presence of an oxidizing agent.

[0087] Compounds of formula (XX) are either commercially available or can be prepared by known methods.

[0088] The conversion to compounds of formula (XXI) (corresponds to formula I(Q16) with p = 0) is generally carried out in a solvent. Preference is given to ethers such as tetrahydrofuran, methyl tert-butyl ether, dioxane, aliphatic hydrocarbons such as hexane, heptane, aromatic hydrocarbons such as toluene, xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, or alcohols such as methanol or ethanol.

[0089] Examples of oxidizing agents are halogenating agents such as N-chlorosuccinimide or hypervalent iodine compounds such as bis(acetato-O)phenyl iodide. Step d)

[0090] The compounds of formula (XXII) (corresponds to formula I(Q16) with p =1) can be prepared analogously to the process described in WO2015 / 002211 by reacting compounds of formula (XXI) with an oxidizing agent.

[0091] Examples of suitable oxidizing agents are sodium periodate or meta-chloroperbenzoic acid.

[0092] Suitable solvents for oxidation include halogenated aliphatic hydrocarbons such as dichloromethane or chloroform, alcohols such as methanol or ethanol, or acetic acid. Procedure E

[0093]

[0094] The radicals R 1< , R 2a< , R 3< , R 11< , R 12< , A 1< , A 2< , A 4< and n have the meanings described above and X 1< stands for halogen. Step a)

[0095] The compounds of formula (XXIII) can be prepared analogously to WO2015 / 002211 by reacting the compounds of formula (VI) with compounds of formula (XVII).

[0096] Compounds of formula (XVII) are either commercially available or can be prepared by known methods.

[0097] The conversion to compounds of formula (XXIII) (corresponds to formula I(Q10)) is generally carried out in a solvent. Preference is given to ethers such as tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycol dimethyl ether, aliphatic hydrocarbons such as hexane, heptane, aromatic hydrocarbons such as toluene, xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, esters such as ethyl acetate, or nitriles such as acetonitrile.

[0098] The reaction can be carried out in the presence of a base. Examples of suitable bases include nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as triethylamine and N,N-diisopropylethylamine; or inorganic bases such as potassium phosphate, potassium carbonate, and sodium hydride. Procedure F

[0099]

[0100] The radicals R 1< , R 2a< , R 3< , R 11< , R 12< , A 1< , A 2< , A 4< and n have the meanings described above and X 1< stands for halogen. Step a)

[0101] The compounds of formula (XXV) (corresponds to formula I(Q11)) can be prepared by reacting the compounds of formula (VI) with compounds of formula (XXIV).

[0102] Compounds of formula (XXIV) are either commercially available or can be prepared by known methods.

[0103] The reaction proceeds under analogous reaction conditions as described in process E. Procedure G

[0104]

[0105] The radicals R 1< , R 2a< , R 3< , R 11< , R 13< , A 1< , A 2< , A 4< and n have the meanings described above and X 1< stands for halogen.

[0106] The compounds of formula (XXVII) (corresponds to formula I(Q15)) can be prepared by reacting the compounds of formula (VI) with compounds of formula (XXVI).

[0107] Compounds of formula (XXVI) are either commercially available or can be prepared by known methods.

[0108] The reaction proceeds under analogous reaction conditions as described in process E. Procedure H

[0109]

[0110] The radicals R 1< , R 2a< , R 3< , R 11< , A 1< , A 2< , A 4< and n have the meanings described above and X 1< stands for halogen and Q stands for O or S. Step a)

[0111] The compounds of formula (XXIX) can be prepared by reacting the compounds of formula (VI) with compounds of formula (XXVIII).

[0112] Compounds of formula (XXVIII) are either commercially available or can be prepared by known methods.

[0113] The reaction proceeds under analogous reaction conditions as described in process E. Step b)

[0114] The compounds of formula (XXXII) (corresponds to formula I(Q12) with Q=O and I(Q13) with Q=S) can be prepared by reacting the compounds of formula (XXIX) with compounds of formula (XXX).

[0115] Compounds of formula (XXX) are either commercially available or can be prepared by known methods.

[0116] The conversion to compounds of formula (XXXII) is generally carried out in a solvent. Preference is given to ethers such as tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycol dimethyl ether, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene, aromatic hydrocarbons such as toluene, xylene, esters such as ethyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, or nitrogen-containing heterocycles such as pyridine or quinoline.

[0117] The reaction can be carried out in the presence of a condensing agent. Examples of suitable condensing agents are carbodiimides such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.

[0118] The reaction can be carried out in the presence of a suitable catalyst. An example of a suitable catalyst is 1-hydroxybenzotriazole.

[0119] The compounds of formula (XXXII) can also be prepared by reacting the compounds of formula (XXIX) with compounds of formula (XXXI).

[0120] Compounds of formula (XXXI) are either commercially available or can be prepared by known methods.

[0121] The reaction to give compounds of formula (XXXII) is generally carried out in a solvent. Preference is given to ethers such as tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycol dimethyl ether, aliphatic hydrocarbons such as hexane, heptane, aromatic hydrocarbons such as toluene, xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, esters such as ethyl acetate, or nitriles such as acetonitrile.

[0122] The reaction can be carried out in the presence of a base. Examples of suitable bases include nitrogen-containing heterocycles such as pyridine, dimethylaminopyridine, picoline, 2,6-lutidine, and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as triethylamine and N,N-diisopropylethylamine; or inorganic bases such as potassium carbonate and sodium hydride. Procedure I

[0123]

[0124] The radicals R 1< , R 2a< , R 3< , R 11< , R 13< , A 1< , A 2< , A 4< , and n have the meanings described above. Step a)

[0125] The compounds of formula (XXXIV) (corresponds to formula I(Q14)) can be prepared by reacting the compounds of formula (XXIX) with compounds of formula (XXXIII).

[0126] Compounds of formula (XXXIII) are either commercially available or can be prepared by known methods.

[0127] The conversion to compounds of formula (XXXIV) is generally carried out in a solvent. Preference is given to ethers such as tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycol dimethyl ether, aliphatic hydrocarbons such as hexane, heptane, aromatic hydrocarbons such as toluene, xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene, esters such as ethyl acetate, nitriles such as acetonitrile, or aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, and dimethyl sulfoxide.

[0128] The reaction can be carried out in the presence of a base. Examples of suitable bases include nitrogen-containing heterocycles such as pyridine, dimethylaminopyridine, picoline, 2,6-lutidine, and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as triethylamine and N,N-diisopropylethylamine; or inorganic bases such as potassium carbonate and sodium hydride. Procedure J

[0129]

[0130] The radicals R 1< , R 2a< , R 3< , A 1< , A 2< and A 4< have the meanings described above and X 2< stands for halogen. Step a)

[0131] The compounds of formula (XXXVI) can be prepared analogously to the process described in US5576335 by reacting compounds of formula (II) with a carboxylic acid of formula (XXXV) in the presence of a condensing agent or a base.

[0132] Compounds of formula (II) are either commercially available or can be prepared by known methods, for example analogously to the processes described in US2003 / 69257 or WO2006 / 65703.

[0133] Carboxylic acids of formula (XXXV) are either commercially available or can be prepared by known methods, for example analogous to the processes described in US2010 / 234604, WO2012 / 61926 or Bioorganic and Medicinal Chemistry Letters, 18 (2008), 5023-5026.

[0134] The reaction of the compounds of formula (II) with carboxylic acids of formula (XXXV) can be carried out in bulk or in a solvent; preferably, the reaction is carried out in a solvent selected from customary solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles such as, for example, acetonitrile or propionitrile; aromatic hydrocarbons such as, for example, toluene or xylene; aprotic polar solvents such as, for example, N,N-dimethylformamide or N-methylpyrrolidone; or nitrogen-containing compounds such as, for example, pyridine.

[0135] Suitable condensing agents are, for example, carbodiimides such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.

[0136] Suitable bases are inorganic bases commonly used in such reactions. Bases selected, for example, from the group consisting of acetates, phosphates, carbonates, and bicarbonates of alkali or alkaline earth metals are preferred. Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate.

[0137] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 180 °C, preferably the reaction is carried out at atmospheric pressure and temperatures from 20 to 140 °C. Step b)

[0138] The compounds of formula (XXXVII) can be prepared by condensation of the compounds of formula (XXXVI), e.g. analogously to the processes described in WO2012 / 86848.

[0139] The reaction to give compounds of formula (XXXVII) can be carried out in bulk or in a solvent; preferably, the reaction is carried out in a solvent selected from customary solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene; nitriles such as, for example, acetonitrile or propionitrile; aromatic hydrocarbons such as, for example, toluene or xylene; aprotic polar solvents such as, for example, N,N-dimethylformamide or N-methylpyrrolidone; or nitrogen-containing compounds such as, for example, pyridine.

[0140] The reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.

[0141] Examples of suitable condensing agents are carbodiimides such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azodiester such as diethylazodicarboxylic acid.

[0142] Examples of suitable acids that can be used in the described reaction are sulfonic acids such as para-toluenesulfonic acid; carboxylic acids such as acetic acid or polyphosphoric acids.

[0143] Examples of suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as triethylamine and N,N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.

[0144] An example of a suitable chlorinating agent is phosphorus oxychloride.

[0145] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 200 °C. Step c)

[0146] The compounds of formula (XXXVIII) can be prepared by reacting the compounds of formula (XXXVII) with compounds of formula (X) in the presence of a base.

[0147] Mercaptan derivatives of formula (X) such as methyl mercaptan, ethyl mercaptan or isopropyl mercaptan are either commercially available or can be prepared by known methods, for example analogously to the processes described in US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329.

[0148] The reaction to give compounds of formula (XXXVIII) can be carried out in bulk or in a solvent; preferably, the reaction is carried out in a solvent selected from conventional solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, and tert-butyl methyl ether; nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; and aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, or dimethyl sulfoxide.

[0149] Examples of suitable bases are inorganic bases from the group consisting of acetates, phosphates, and carbonates of alkali or alkaline earth metals. Preferred bases are cesium carbonate, sodium carbonate, and potassium carbonate. Other suitable bases are alkali metal hydrides such as sodium hydride.

[0150] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 200 °C. Step d)

[0151] The compounds of formula (XXXIX) can be prepared by oxidation of the compounds of formula (XXXVIII). The oxidation is generally carried out in a solvent selected from among conventional solvents that are inert under the prevailing reaction conditions. Preferred solvents are halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid, propionic acid, or water.

[0152] Examples of suitable oxidizing agents are hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.

[0153] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from -20°C to 120°C. Step e)

[0154] The compounds of formula (XIXa) can be prepared by oxidation of the compounds of formula (XXXIX). The oxidation is generally carried out in a solvent. Preferred solvents are halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid, propionic acid, or water.

[0155] Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.

[0156] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from -20°C to 120°C.

[0157] The further conversion of the compound of formulas (XIXa), (XXXVIII) or (XXXIX) is carried out analogously to processes D, H and I. Procedure K

[0158]

[0159] The radicals R 1< , R 2a< , R 3< , R 13< , A 1< , A 2< , A 4< and n have the meanings described above and X 1< stands for halogen. Step a)

[0160] The compounds of formula (XXXXI) (corresponds to formula I(Q17)) can be prepared by reacting the compounds of formula (VI) with compounds of formula (XXXX), e.g. analogously to the processes described in US4558134 or US2014 / 275026.

[0161] Compounds of formula (XXXX) are either commercially available or can be prepared by known methods.

[0162] The reaction to give compounds of formula (XXXXI) can be carried out in bulk or in a solvent; preferably, the reaction is carried out in a solvent selected from conventional solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; and aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, or dimethyl sulfoxide.

[0163] Examples of suitable bases are inorganic bases from the group consisting of acetates, phosphates, and carbonates of alkali or alkaline earth metals. Preferred bases are cesium carbonate, sodium carbonate, potassium carbonate, and potassium tert-butoxide. Other suitable bases are alkali metal hydrides such as sodium hydride.

[0164] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 200 °C. Procedure L

[0165]

[0166] The radicals R 1< , R 2a< , R 3< , R 13< , A 1< , A 2< and A 4< have the meanings described above and X 1< stands for halogen. Step a)

[0167] The compounds of formula (XXXXIII) (corresponds to formula I(Q5) with m=0) can be prepared by reacting the compounds of formula (XIII) with compounds of formula (XXXXII).

[0168] Compounds of formula (XXXXII) are either commercially available or can be prepared by known methods.

[0169] The reaction to give compounds of formula (XXXXIII) can be carried out in bulk or in a solvent; preferably, the reaction is carried out in a solvent selected from conventional solvents that are inert under the prevailing reaction conditions. Preference is given to ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; and aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, or dimethyl sulfoxide.

[0170] Examples of suitable bases are inorganic bases from the group consisting of acetates, phosphates and carbonates of alkali or alkaline earth metals. Preferred are cesium carbonate, sodium carbonate, potassium carbonate and potassium tert-Butoxide. Other suitable bases are alkali metal hydrides such as sodium hydride.

[0171] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 200 °C. Step b)

[0172] The compounds of formula (XXXXIV) (corresponds to formula (I (Q5) with m=1) can be prepared by oxidation of the compounds of formula (XXXXIII). The oxidation is generally carried out in a solvent selected from conventional solvents that are inert under the prevailing reaction conditions. Preference is given to halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid, propionic acid or water.

[0173] Examples of suitable oxidizing agents are hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.

[0174] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from -20°C to 120°C. Step c)

[0175] The compounds of formula (XXXXV) (corresponds to formula (I (Q5) with m=2) can be prepared by oxidation of the compounds of formula (XXXXIV). The oxidation is generally carried out in a solvent. Preferred are halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid, propionic acid or water.

[0176] Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.

[0177] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from -20°C to 120°C. Step d)

[0178] The compounds of formula (XXXXV) can also be prepared in a one-step process by oxidation of the compounds of formula (XXXXIII). The oxidation is generally carried out in a solvent. Preferred solvents are halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid, propionic acid, or water.

[0179] Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.

[0180] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from -20°C to 120°C. Procedure M

[0181]

[0182] The radicals R 1< , R 2a< , R 3< , R 13< , A 1< , A 2< and A 4< have the meanings described above. Ns = nosyl / 4-nitrobenzylsulfonyl Step a)

[0183] The compounds of formula (XXXXVI) can be prepared by imination of the compounds of formula (XXXXIV) with 4-nitrobenzylsulfonylamide (NsNH 2 ) and a hypervalent iodine compound under metal catalysis, e.g. analogously to the processes described in Organic Letters 2006, 8, 2349 and Chemistry - A European Journal 2007, 13, 6674.

[0184] The reaction to give compounds of formula (XXXXVI) is preferably carried out in a solvent selected from among conventional solvents that are inert under the prevailing reaction conditions. Nitriles, such as acetonitrile, or halogenated alkanes, such as dichloromethane, are preferred.

[0185] Examples of metal catalysts include iron, copper, silver, or rhodium compounds, such as iron(II) acetylacetonate, iron(III) acetylacetonate, and rhodium(II) acetate. Diacetoxyiodobenzene or iodosylbenzene are frequently used as hypervalent iodine compounds.

[0186] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at room temperature. Step b)

[0187] The compounds of formula (XXXXVII) (corresponds to formula I(Q6)) can be prepared from compounds of formula (XXXXVI) by reaction with a thiol under basic conditions, e.g. analogously to the processes described in Organic Letters 2006, 8, 2349; Chemistry - A European Journal 2007, 13, 6674 and WO2006 / 101860.

[0188] The conversion to compounds of formula (XXXXVII) is usually carried out in a solvent. Ethers such as tetrahydrofuran or nitriles such as acetonitrile are preferred.

[0189] For example, thiophenol is used as a thiol in combination with an inorganic base from the group consisting of carbonates of alkali or alkaline earth metals, such as cesium carbonate. The use of a solution of sodium thiomethoxide in methanol has also been described.

[0190] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from -78 °C to 30 °C. Procedure N

[0191]

[0192] The radicals R 1< , R 2a< , R 3< , R 13< , A 1< , A 2< , and A 4< have the meanings described above. Ns = nosyl / 4-nitrobenzylsulfonyl. Step a)

[0193] The compounds of formula (XXXXVI) can be prepared by reacting compounds of formula (XXXXIII) analogously to the processes described in process M, step a).

[0194] The further conversion of compounds of formula (XXXXVI) to compounds of formula (XXXXVII) proceeds under analogous reaction conditions as described in process M. Procedure O

[0195]

[0196] The radicals R 1< , R 2a< , R 3< , R 13< , A 1< , A 2< and A 4< have the meanings described above. Step a)

[0197] The compounds of formula (XXXXVIII) (corresponds to formula I(Q8)) can be prepared from compounds of formula (XXXXIII) by imination with cyanamide in the presence of a hypervalent iodine compound, e.g., analogous to the processes described in Organic Letters 2007, 9, 2951. The conversion to compounds of formula (XXXXVIII) is generally carried out in acetonitrile as the solvent. Diacetoxyiodobenzene or iodosylbenzene are frequently used as the hypervalent iodine compound. The reaction can be carried out under vacuum, at atmospheric pressure, or under superatmospheric pressure, and at temperatures from 0 °C to 30 °C.

[0198] The compounds of formula (XXXXVIII) can also be prepared from compounds of formula (XXXXIII) by imination with cyanamide in the presence of N-Bromosuccinimide (NBS) or iodine under basic conditions, e.g., analogous to the processes described in Organic Letters 2007, 9, 3809 or WO2014 / 29830. The conversion to compounds of formula (XXXXVIII) is carried out in this case in a solvent. Alcohols such as methanol, ethers such as tetrahydrofuran, or nitriles such as acetonitrile are preferably used. Examples of suitable bases are alkoxides such as potassium tert -Butoxide. Other suitable bases are alkali metal hydrides such as sodium hydride. The reaction can be carried out under vacuum, at atmospheric pressure, or under superatmospheric pressure, and at room temperature. Step b)

[0199] The compounds of formula (XXXXIX) (corresponds to formula I(Q7)) can be prepared from compounds of formula (XXXXVIII) by oxidation in a basic medium, e.g., analogously to the processes described in Organic Letters 2007, 9, 2951; Organic Letters 2007, 9, 3809 or WO2014 / 140075. The oxidation is generally carried out in a solvent. Alcohols such as ethanol are preferred. Meta-chloroperbenzoic acid, for example, is used as an oxidizing agent. Examples of suitable bases are carbonates such as potassium carbonate. The reaction can be carried out under vacuum, at atmospheric pressure, or under superatmospheric pressure, and at temperatures from 0°C to 30°C. Procedure P

[0200]

[0201] The radicals R 1< , R 2a< , R 3< , R 11< , R 12< , A 1< , A 2< and A 4< have the meanings described above. Bn = benzyl / CH 2 Ph. Step a)

[0202] The compounds of formula (L) can be prepared from intermediates of formula (XXXXIIIa) by oxidation in the presence of a chlorine source, e.g. analogously to the processes described in WO2008 / 2244 and WO2010 / 24451.

[0203] The conversion to compounds of formula (L) is usually carried out in a solvent. Halogenated alkanes such as dichloromethane or carbon tetrachloride are preferred. Mixtures with water are frequently used.

[0204] Chlorine gas, N-chlorosuccinimide or 1,3-dichloro-5,5-dimethylhydantoin are used as chlorine sources and oxidizing agents.

[0205] The reactions are often carried out in acidic conditions. Carboxylic acids such as formic acid or acetic acid are used as acids.

[0206] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from 0 °C to 30 °C. Step b)

[0207] The compounds of formula (LII) (corresponds to formula I(Q9)) can be prepared from compounds of formula (L) with compounds of formula (XVII) under standard conditions.

[0208] The conversion to compounds of formula (LII) is generally carried out in a solvent. Preference is given to ethers such as tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycol dimethyl ether, aliphatic hydrocarbons such as hexane, heptane, aromatic hydrocarbons such as toluene, xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, or chlorobenzene, esters such as ethyl acetate, nitriles such as acetonitrile, or aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, and dimethyl sulfoxide.

[0209] The reaction can be carried out in the presence of a base. Examples of suitable bases include nitrogen-containing heterocycles such as pyridine, dimethylaminopyridine, picoline, 2,6-lutidine, and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as triethylamine and N,N-diisopropylethylamine; or inorganic bases such as potassium carbonate and sodium hydride. Procedure Q

[0210]

[0211] The radicals R 1< , R 2a< , R 3< , R 8< , A 1< , A 2< , A 4< and n have the meanings described above, R 11< stands for methyl, R 12< stands for methoxy and X stands for halogen. Step a)

[0212] The compounds of formula (LIV) (corresponds to formula I(Q1)) can be prepared by converting compounds of formula (LIII) into an organometallic compound and subsequent reaction with compounds of formula (Ia), e.g. analogously to the processes described in US5821246 and European Journal of Medicinal Chemistry 2012 , 58, p. 396.

[0213] Compounds of formula (LIII) are either commercially available or can be prepared by known methods.

[0214] The organometallic compounds can be produced, for example, from compounds of formula (LIII) by reaction with magnesium or lithium alkyls.

[0215] The conversion to compounds of formula (LV) is usually carried out in a solvent. Ethers such as tetrahydrofuran or diethyl ether are preferred.

[0216] The reaction can be carried out under vacuum, at atmospheric pressure or under excess pressure and at temperatures from -78 °C to 45 °C. Step b)

[0217] Thioketones of formula (LV) (corresponds to formula I(Q2)) can be prepared from compounds of formula (LIV) by reaction with a sulfurizing reagent, for example Lawesson's reagent or P4S10. Procedure R

[0218]

[0219] The radicals R 1< , R 2a< , R 3< , R 8< , R 11< , R 12< , A 1< , A 2< , A 4< and n have the meanings described above and X 1< stands for halogen.

[0220] Compounds of formula (LVI) can be prepared, for example, from compounds of formula (VI), for which X 1< preferably represents halogen from the series consisting of chlorine or bromine, by generally known methods (cf. Chem. Rev. 1995, 95, 2457-2483; Tetrahedron 2002, 58, 9633-9695; Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004). For example, compounds of formula (VI) can be reacted with suitable olefinic boronic acids or their esters by known methods (cf. WO2006 / 21805) in the presence of suitable catalysts from the series consisting of transition metal salts to give compounds of formula (LVI). Preferred coupling catalysts are, for example, palladium catalysts such as [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) or tetrakis(triphenylphosphine)palladium.Sodium or potassium carbonates are preferably used as suitable basic reaction auxiliaries for carrying out the processes.

[0221] Some of the required olefinic boronic acids or olefinic boronic acid esters are known and / or commercially available or can be prepared by generally known methods (cf. Boronic Acids (Eds.: DG Hall), 2nd ed., Wiley-VCH, Weinheim, 2011).

[0222] The invention also relates to compounds of formula (IX) in which R 2a< , R 3< , A 1< , A 2< and A 4< have the meanings described above and X 1< or X 2< represents halogen (preferably fluorine, chlorine, bromine, iodine, particularly preferably chlorine or fluorine), with the exception of the following compound

[0223] The invention also relates to compounds of formula (XI) in which R 1< , R 2a< , R 3< , A 1< , A 2< and A 4< have the meanings described above and X 1< stands for halogen (preferably fluorine, chlorine, bromine iodine, particularly preferably chlorine or fluorine).

[0224] The invention also relates to compounds of formula (XII) in which R 1< , R 2a< , R 3< , A 1< , A 2< and A 4< have the meanings described above and X 1< stands for halogen (preferably fluorine, chlorine, bromine iodine, particularly preferably chlorine or fluorine).

[0225] The invention also relates to compounds of formula (XIII) in which R 1< , R 2a< , R 3< , A 1< , A 2< and A 4< have the meanings described above and X 1< represents halogen (preferably fluorine, chlorine, bromine, iodine, particularly preferably chlorine or fluorine), with the exception of the compound of the following formula Processes and uses

[0226] The invention also relates to methods for controlling animal pests, in which compounds of formula (I) are allowed to act on animal pests and / or their habitat. The control of animal pests is preferably carried out in agriculture and forestry, and in material protection. This preferably excludes methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods performed on the human or animal body.

[0227] The invention further relates to the use of the compounds of formula (I) as pesticides, in particular plant protection agents.

[0228] In the context of this application, the term pesticide always includes the term plant protection product.

[0229] The compounds of formula (I) are suitable for protecting plants and plant organs from biotic and abiotic stress factors, increasing crop yields, improving harvest quality, and controlling animal pests, particularly insects, arachnids, helminths, nematodes, and mollusks, which occur in agriculture, horticulture, animal husbandry, aquaculture, forestry, gardens and recreational facilities, in stored product and material protection, and in the hygiene sector, while exhibiting good plant tolerance, favorable warm-blooded toxicity, and good environmental compatibility. They are preferably used as pesticides. They are effective against normally sensitive and resistant species, as well as against all or individual developmental stages. The pests mentioned above include: Pests from the phylum Arthropoda, especially from the class Arachnida, e.g. Acarus spp., e.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., e.g. Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., e.g. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., e.g. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., e.g. Eutetranychus banksi, Eriophyes spp., e.g. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., e.g. Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., zBOligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., e.g. Panonychus citri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., e.g. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., e.g. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; aus der Klasse der Chilopoda zB Geophilus spp., Scutigera spp.; aus der Ordnung oder der Klasse der Collembola zB Onychiurus armed; Green Sminthurus; aus der Klasse der Diplopoda zBBlaniulus guttulatus; from the class of Insecta, eg from the order of Blattodea eg Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., eg Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera, e.g. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agriotes spp., e.g. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., e.g. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., e.g. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., e.g. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., e.g.Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., e.g. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., e.g. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., e.g. Curculio caryae, Curculio caryatrypes,Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., e.g. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., zB Epilachna borealis, Epilachna varivestis, Epitrix spp., zBEpitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., e.g. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa ​​decemlineata, Leucoptera spp., e.g. Leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus (= Hyperodes) spp., Lixus spp., Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., e.g. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., zB., e.g. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., e.g. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., e.g. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Sinoxylon perforans, Sitophilus spp., e.g. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., eg Sternechus paludatus, Symphyletes spp., Tanymecus spp., eg Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., eg Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., eg Zabrus tenebrioides; from the order of Dermaptera eg Anisolabis maritime, Forficula auricularia, Labidura riparia; from the order of Diptera e.g. Aedes spp., e.g. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., e.g. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., e.g. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., e.g. Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., e.g. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., e.g.Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., e.g. Dasineura brassicae, Delia spp., e.g. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., e.g. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., e.g. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., e.g. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., e.g. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya spp., eg Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., eg Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., eg Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., eg Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; aus der Ordnung der Hemiptera zB Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., zB Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., zB Amrasca bigutulla, Amrasca devastating, Anuraphis cardui, Aonidiella spp., zB Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., zBAphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., z.b. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., z.b. Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., eg Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Drosicha spp., Dysaphis spp., e.g. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., e.g. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., e.g. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolima spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., e.g. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., eg Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., eg Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., egMacrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., eg Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae,. Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., e.g. Nephotettix cincticeps,, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., e.g. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., e.g. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., e.g. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., e.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., e.g.Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., e.g. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., e.g. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., e.g. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastroccus spp., Rhopalosiphum spp., e.g. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., e.g. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephala spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., eg Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., eg Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; from the suborder Heteroptera e.g. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., e.g. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., e.g. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., e.g. Lygocoris pabulinus, Lygus spp., e.g.Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., e.g. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., e.g. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; from the order of Hymenoptera, e.g. Acromyrmex spp., Athalia spp., e.g. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., e.g. Diprion similis, Hoplocampa spp., e.g. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., e.g. Vespa crabro, Wasmannia auropunctata, Xeris spp.; from the order of Isopoda, e.g.Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of Isoptera, for example Coptotermes spp., for example Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermes spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., for example Reticulitermes flavipes, Reticulitermes hesperus; from the order of Lepidoptera e.g. Achroia grisella, Acronicta major, Adoxophyes spp., e.g. Adoxophyes orana, Aedia leucomelas, Agrotis spp., e.g. Agrotis segetum, Agrotis ipsilon, Alabama spp., e.g. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., e.g. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., e.g.Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., e.g. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., e.g. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., e.g. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., eg Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., eg Helicoverpa armigera, Helicoverpa zea, Heliothis spp., eg Heliothis virescens, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., e.g. Leucoptera coffeella, Lithocolletis spp., e.g. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., e.g. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., e.g. Lymantria dispar, Lyonetia spp., e.g. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., e.g. Ostrinia nubilalis, Oulema melanopus, Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., e.g. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., zB Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., zB Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., zBPieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., e.g. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., e.g. Schoenobius bipunctifer, Scirpophaga spp., e.g. Scirpophaga innotata, Scotia segetum, Sesamia spp., e.g. Sesamia inferens, Sparganothis spp., Spodoptera spp., e.g. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., ZB Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.; aus der Ordnung der Orthoptera oder Saltatoria zB Acheta domesticus, Dichroplus spp., Gryllotalpa spp., zBGryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., e.g. Locusta migratoria, Melanoplus spp., e.g. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of Phthiraptera e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; from the order of Psocoptera e.g. Lepinotus spp., Liposcelis spp.; from the order of Siphonaptera e.g. Ceratophyllus spp., Ctenocephalides spp., e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera eg Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., eg Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., e.g. Thrips palmi, Thrips tabaci; from the order Zygentoma (= Thysanura), e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class Symphyla, e.g. Scutigerella spp., e.g. Scutigerella immaculata; pests from the phylum Mollusca, in particular from the class Bivalvia, e.g. Dreissena spp.; as well as from the class Gastropoda, e.g. Arion spp., e.g. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., e.g. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; animal and human parasites from the phyla Platyhelminthes and Nematoda, e.g. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp., Opisthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp.. Plant pests from the phylum Nematoda, i.e. plant parasitic nematodes, in particular Aglenchus spp., e.g. Aglenchus agricola, Anguina spp., e.g. Anguina tritici, Aphelenchoides spp., e.g. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., e.g. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., e.g. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., e.g. Cacopaurus pestis, Criconemella spp., e.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., e.g.Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., e.g. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., e.g. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., e.g. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., e.g. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hoplolaimus spp., Longidorus spp., e.g. Longidorus africanus, Meloidogyne spp., e.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., e.g. Paratrichodorus minor, Pratylenchus spp., e.g. Pratylenchus penetrans, Pseudohalenchus spp., Psilnchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., e.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., e.g.Trichodorus obtusus, Trichodorus primitivus, Tylenchulus spp., Tylenchorhynchus spp., e.g. Tylenchorhynchus annulatus, Tylenchulus spp., e.g. Tylenchulus semipenetrans, Xiphinema spp., e.g. Xiphinema index. .

[0230] Furthermore, the order of Coccidia, e.g. Eimeria spp., can be combated from the subkingdom of Protozoa.

[0231] The compounds of formula (I) can, if appropriate, also be used in certain concentrations or application rates as herbicides, safeners, growth regulators, or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antifungals, bactericides, viricides (including agents against viroids), or as agents against MLO (Mycoplasma-like organisms) and RLO (Rickettsia-like organisms). They can also be used, if appropriate, as intermediates or precursors for the synthesis of other active ingredients. Formulations

[0232] The present invention further relates to formulations and use forms prepared therefrom as pesticides, such as drench, drip and spray mixtures, comprising at least one compound of the formula (I). Optionally, the use forms contain further pesticides and / or action-enhancing adjuvants such as penetration enhancers, e.g. vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetative fatty acids such as rapeseed oil or soybean oil methyl esters or alkanol alkoxylates and / or spreading agents such as alkylsiloxanes and / or salts, e.g. organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such as dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such asGlycerin and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizers.

[0233] Typical formulations include water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR), and capsule concentrates (CS); these and other possible formulation types are described, for example, by Crop Life International and in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. Optionally, the formulations contain, in addition to one or more compounds of formula (I), other agrochemical active ingredients.

[0234] Preferably, these are formulations or application forms that contain excipients such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners, and / or other excipients such as adjuvants. An adjuvant in this context is a component that enhances the biological activity of the formulation without the component itself having a biological effect. Examples of adjuvants include agents that promote retention, spreading behavior, adhesion to the leaf surface, or penetration.

[0235] These formulations are prepared in a known manner, e.g., by mixing the compounds of formula (I) with excipients such as extenders, solvents, and / or solid carriers and / or other excipients such as surfactants. The formulations are prepared either in suitable facilities or before or during use.

[0236] Substances which can be used as auxiliaries are those which are suitable for imparting particular properties, such as certain physical, technical and / or biological properties, to the formulation of the compounds of formula (I) or to the application forms prepared from these formulations (such as, for example, ready-to-use pesticides such as spray mixtures or seed dressings).

[0237] Suitable extenders include water, polar and non-polar organic chemical liquids, e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).

[0238] If water is used as an extender, organic solvents can also be used as auxiliary solvents. The following are essentially suitable liquid solvents: aromatics such as xylene, toluene, or alkylnaphthalenes; chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes, or methylene chloride; aliphatic hydrocarbons such as cyclohexane or paraffins, e.g., petroleum fractions, mineral and vegetable oils; alcohols such as butanol or glycol and their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; strongly polar solvents such as dimethylformamide and dimethyl sulfoxide; and water.

[0239] In principle, all suitable solvents can be used. Suitable solvents include, for example, aromatic hydrocarbons such as xylene, toluene, or alkylnaphthalenes; chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethylene, or methylene chloride; aliphatic hydrocarbons such as cyclohexane; paraffins; petroleum fractions; mineral and vegetable oils; alcohols such as methanol, ethanol, isopropanol, butanol, or glycol, as well as their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; strongly polar solvents such as dimethyl sulfoxide; and water.

[0240] In principle, any suitable carrier material can be used. Particularly suitable carrier materials include: ammonium salts and natural mineral flours such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth, and synthetic mineral flours such as highly dispersed silica, aluminum oxide, and natural or synthetic silicates, resins, waxes, and / or solid fertilizers. Mixtures of such carrier materials can also be used. Suitable carrier materials for granules include: crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, and dolomite, as well as synthetic granules made from inorganic and organic flours and granules made from organic materials such as sawdust, paper, coconut shells, corn cobs, and tobacco stalks.

[0241] Liquefied gaseous extenders or solvents can also be used. Extenders or carriers that are gaseous at normal temperature and pressure are particularly suitable, e.g., aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen, and carbon dioxide.

[0242] Examples of emulsifying and / or foam-forming agents, dispersing agents or wetting agents with ionic or non-ionic properties or mixtures of these surface-active substances are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of compounds containing sulphates, sulphonates and phosphates, e.g. alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, lignin sulphite waste liquors and methylcellulose.The presence of a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when the application takes place in water.

[0243] Further excipients that may be present in the formulations and the application forms derived therefrom include dyes such as inorganic pigments, e.g. iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrients and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

[0244] Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers, or other agents that improve chemical and / or physical stability may also be present. Foaming agents or defoamers may also be present.

[0245] Furthermore, the formulations and derived application forms may also contain adhesives such as carboxymethylcellulose, natural and synthetic powdered, granular, or latex-like polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids as additional excipients. Other excipients may include mineral and vegetable oils.

[0246] If necessary, further excipients may be included in the formulations and the application forms derived therefrom. Such additives include, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration enhancers, retention enhancers, stabilizers, sequestering agents, complexing agents, humectants, and spreading agents. In general, the compounds of formula (I) can be combined with any solid or liquid additive commonly used for formulation purposes.

[0247] All substances that reduce the dynamic surface tension, such as dioctyl sulfosuccinate, or that increase the viscoelasticity, such as hydroxypropyl guar polymers, can be considered as retention promoters.

[0248] In this context, penetration enhancers are considered to be all substances commonly used to improve the penetration of agrochemical active ingredients into plants. Penetration enhancers are defined in this context by their ability to penetrate the plant cuticle from the (usually aqueous) application solution and / or spray coating, thereby increasing the mobility of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property.Examples include alcohol alkoxylates such as coconut fat ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil methyl ester, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.

[0249] The formulations preferably contain between 0.00000001 and 98% by weight of the compound of formula (I), more preferably between 0.01 and 95% by weight of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation.

[0250] The content of the compound of formula (I) in the use forms prepared from the formulations (particularly pesticides) can vary widely. The concentration of the compound of formula (I) in the use forms can typically be between 0.00000001 and 95% by weight of the compound of formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the use form. Application is carried out in a conventional manner adapted to the use forms. Mixtures

[0251] The compounds of formula (I) can also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologics, beneficial organisms, herbicides, fertilizers, bird repellents, phytotonics, sterilants, safeners, semiochemicals, and / or plant growth regulators, for example, to broaden the spectrum of activity, prolong the duration of action, increase the speed of action, prevent repellency, or prevent the development of resistance. Furthermore, such active ingredient combinations can improve plant growth and / or tolerance to abiotic factors such as high or low temperatures, drought, or elevated water or soil salinity.It is also possible to improve flowering and fruiting behaviour, optimise germination and rooting, facilitate harvesting and increase crop yields, influence ripening, increase the quality and / or nutritional value of the harvested products, extend storage life and / or improve the processability of the harvested products.

[0252] Furthermore, the compounds of formula (I) can be present in mixtures with other active ingredients or semiochemicals, such as attractants and / or bird repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of formula (I) can be used in mixtures with agents for improving plant properties, such as growth, yield, and harvest quality.

[0253] In a particular embodiment of the invention, the compounds of formula (I) are present in formulations or in the use forms prepared from these formulations in a mixture with other compounds, preferably those as described below.

[0254] If one of the compounds listed below can occur in different tautomeric forms, these forms are also included, even if they are not explicitly mentioned in every case. Insecticides / Acaricides / Nematicides

[0255] The active ingredients mentioned here by their common name are known and are described, for example, in the Pesticide Manual ("The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) or can be researched on the Internet (e.g. http: / / www.alanwood.net / pesticides). (1) Acetylcholinesterase (AChE) Inhibitoren, wie beispielsweise Carbamate, z.B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb oder organophosphate, z.B.Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. (2) GABA-gesteuerte Chlorid-Kanal-Antagonisten, wie beispielsweise Cyclodien-organochlorine, z.B.Chlordane and endosulfan or phenylpyrazoles (fiproles), e.g. ethiprole and fipronil. (3) Sodium channel modulators / voltage-dependent sodium channel blockers, such as pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomers], deltamethrin, empenthrin [(EZ)-(1R) isomers), esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans-isomer), prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)- isomers)], tralomethrin and transfluthrin or DDT or methoxychlor.(4) Nicotinergic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, e.g., acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam, or nicotine, or sulfoxaflor, or flupyradifurone. (5) Nicotinergic acetylcholine receptor (nAChR) allosteric activators, such as spinosins, e.g., spinetoram and spinosad. (6) Chloride channel activators, such as avermectins / milbemycins, e.g., abamectin, emamectin benzoate, lepimectin, and milbemectin. (7) Juvenile hormone mimics, such as juvenile hormone analogues, e.g., hydroprene, kinoprene, and methoprene, or fenoxycarb or pyriproxyfen. (8) Active ingredients with unknown or non-specific mechanisms of action, such as alkyl halides, e.g., methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic. (9) Selective feeding inhibitors, e.g., pymetrozine or flonicamid. (10) Mite growth inhibitors, e.g.,Clofentezine, hexythiazox, and diflovidazine or etoxazole. (11) Microbial disruptors of the insect intestinal membrane, e.g., Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1. (12) Inhibitors of oxidative phosphorylation, ATP disruptors, such as diafenthiuron, or organotin compounds, e.g., azocyclotin, cyhexatin, and fenbutatin oxide, or propargite or tetradifon. (13) Uncouplers of oxidative phosphorylation by interrupting the H-proton gradient, such as chlorfenapyr, DNOC, and sulfluramide. (14) Nicotinergic acetylcholine receptor antagonists, such as bensultap, cartap hydrochloride, thiocyclam, and thiosultap sodium.(15) Type 0 chitin biosynthesis inhibitors, such as bistriflurone, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron. (16) Type 1 chitin biosynthesis inhibitors, such as buprofezin. (17) Moulting inhibitors (particularly in dipterans), such as cyromazine. (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide. (19) Octopaminergic agonists, such as amitraz. (20) Complex III electron transport inhibitors, such as hydramethylnon, acequinocyl, or fluacrypyrim. (21) Complex I electron transport inhibitors, for example, METI acaricides, e.g., fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, and tolfenpyrad, or rotenone (Derris). (22) Voltage-dependent sodium channel blockers, e.g., indoxacarb or metaflumizone.(23) Acetyl-CoA carboxylase inhibitors, such as tetronic and tetramic acid derivatives, e.g., spirodiclofen, spiromesifen, and spirotetramat. (24) Complex IV electron transport inhibitors, such as phosphines, e.g., aluminum phosphide, calcium phosphide, phosphine, and zinc phosphide or cyanide. (25) Complex II electron transport inhibitors, such as, e.g., cyenopyrafen and cyflumetofen. (28) Ryanodine receptor effectors, such as diamides, e.g., chlorantraniliprole, cyantraniliprole, and flubendiamide.

[0256] Other active ingredients with an unknown or ambiguous mechanism of action, such as afidopyropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol, diflovidazine, flometoquin, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, lotilaner, meperfluthrin, paichongding, pyflubumide, pyridalyl, pyrifluquinazone, pyriminostrobin, sarolaner, tetramethylfluthrin, Tetraniliprole, tetrachlorantraniliprole, tioxazafen, triflumezopyrim and iodomethane; furthermore preparations based on Bacillus firmus (I-1582, BioNeem, Votivo), as well as the following known active compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006 / 043635),{1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorspiro[indol-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003 / 106457), 2-Chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006 / 003494), 3-(2,5-Dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2009 / 049851), 3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (known from WO2009 / 049851), 4-(But-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004 / 099160), 4-(But-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known from WO2003 / 076415), PF1364 (CAS Reg. No. 1204776-60-2), Methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazine carboxylate (known from WO2005 / 085216),Methyl-2-[2-({[3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyan-3-methylbenzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005 / 085216), Methyl-2-[2-({[3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyan-3-methylbenzoyl]-2-methylhydrazincarboxylat (bekannt aus WO2005 / 085216), Methyl-2-[3,5-dibrom-2-({[3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005 / 085216), N-[2-(5-Amino-1,3,4-thiadiazol-2-yl)-4-chlor-6-methylphenyl]-3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-carboxamid (bekannt aus CN102057925), 4-[5-(3,5-Dichlorphenyl)-5-(trifluormethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamid (bekannt aus WO2009 / 080250), N-[(2E)-1-[(6-Chlorpyridin-3-yl)methyl]pyridin-2(1H)-yliden]-2,2,2-trifluoracetamid (bekannt aus WO2012 / 029672), 1-[(2-Chlor-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olat (bekannt aus WO2009 / 099929),1-[(6-Chlorpyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olat (bekannt aus WO2009 / 099929), 4-(3-{2,6-Dichlor-4-[(3,3-dichlorprop-2-en-1-yl)oxy]phenoxy)propoxy)-2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN101337940), N-[2-(tert-Butylcarbamoyl)-4-chlor-6-methylphenyl]-1-(3-chlorpyridin-2-yl)-3-(fluormethoxy)-1H-pyrazol-5-carboxamid (bekannt aus WO2008 / 134969, Butyl-[2-(2,4-dichlorphenyl)-3-oxo-4-oxaspiro[4.5]dec-1-en-1-yl]-carbonat (bekannt aus CN 102060818), 3E)-3-[1-[(6-Chlor-3-pyridyl)methyl]-2-pyridyliden]-1,1,1-trifluor-propan-2-on (bekannt aus WO2013 / 144213, N-(Methylsulfonyl)-6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-carboxamid (bekannt aus WO2012 / 000896), N-[3-(Benzylcarbamoyl)-4-chlorphenyl]-1-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-1H-pyrazol-5-carboxamid bekannt aus WO2010 / 051926)., Fungicides

[0257] The active ingredients specified here with their "common name" are known, for example, described in the "Pesticide Manual" or on the Internet (for example: http: / / www.alanwood.net / pesticides ).

[0258] All listed fungicidal mixing partners of classes (1) to (15) can optionally form salts with corresponding bases or acids, provided suitable functional groups are present. Furthermore, tautomeric forms are also included for the listed fungicidal mixing partners of classes (1) to (15), provided tautomerism is possible. 1) Inhibitoren der Ergosterolbiosynthese, zum Beispiel (1.01) Aldimorph, (1.02) Azaconazol, (1.03) Bitertanol, (1.04) Bromuconazol, (1.05) Cyproconazol, (1.06) Diclobutrazol, (1.07) Difenoconazol, (1.08) Diniconazol, (1.09) Diniconazol-M, (1.10) Dodemorph, (1.11) Dodemorphacetat, (1.12) Epoxiconazol, (1.13) Etaconazol, (1.14) Fenarimol, (1.15) Fenbuconazol, (1.16) Fenhexamid, (1.17) Fenpropidin, (1.18) Fenpropimorph, (1.19) Fluquinconazol, (1.20) Flurprimidol, (1.21) Flusilazol, (1.22) Flutriafol, (1.23) Furconazol, (1.24) Furconazol-cis, (1.25) Hexaconazol, (1.26) Imazalil, (1.27) Imazalilsulfat, (1.28) Imibenconazol, (1.29) Ipconazol, (1.30) Metconazol, (1.31) Myclobutanil, (1.32) Naftifin, (1.33) Nuarimol, (1.34) Oxpoconazol, (1.35) Paclobutrazol, (1.36) Pefurazoat, (1.37) Penconazol, (1.38) Piperalin, (1.39) Prochloraz, (1.40) Propiconazol, (1.41) Prothioconazol, (1.42) Pyributicarb, (1.43) Pyrifenox, (1.44) Quinconazol, (1.45) Simeconazol, (1.46) Spiroxamin, (1.47) Tebuconazol, (1.48) Terbinafin, (1.49) Tetraconazol, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Tridemorph, (1.53) Triflumizol, (1.54) Triforin, (1.55) Triticonazol, (1.56) Uniconazol, (1.57) Uniconazol-p, (1.58) Viniconazol, (1.59) Voriconazol, (1.60) 1-(4-Chlorphenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61) 1-(2,2-Dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazol-5-carbonsäuremethylester, (1.62) N'-{5-(Difluormethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamid, (1.63) N-Ethyl-N-methyl-N'-{2-methyl-5-(trifluormethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamid, (1.64) O-[1-(4-Methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazol-1-carbothioat, (1.65) Pyrisoxazol, (1.66) 2-{[3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.67) 1-{[3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanat, (1.68) 5-(Allylsulfanyl)-1-{[3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol, (1.69) 2-[1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.70) 2-{[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.71) 2-{[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.72) 1-{[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanat, (1.73) 1-{[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanat, (1.74) 5-(Allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol, (1.75) 5-(Allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol, (1.76) 2-[(2S,4S,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.77) 2-[(2R,4S,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.78) 2-[(2R,4R,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.79) 2-[(2S,4R,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.80) 2-[(2S,4S,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.81) 2-[(2R,4S,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.82) 2-[(2R,4R,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.83) 2-[(2S,4R,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.84) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.85) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.86) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.87) 2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.88) 2-[2-Chlor-4-(2,4-dichlorphenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.89) (2R)-2-(1-Chlorcyclopropyl)-4-[(1R)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.90) (2R)-2-(1-Chlorcyclopropyl)-4-[(1S)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.91) (2S)-2-(1-Chlorcyclopropyl)-4-[(1S)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.92) (2S)-2-(1-Chlorcyclopropyl)-4-[(1R)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.93) (1S,2R,5R)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.94) (1R,2S,5S)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.95) 5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol. 2) Inhibitoren der Atmungskette am Komplex I oder II, zum Beispiel (2.01) Bixafen, (2.02) Boscalid, (2.03) Carboxin, (2.04) Diflumetorim, (2.05) Fenfuram, (2.06) Fluopyram, (2.07) Flutolanil, (2.08) Fluxapyroxad, (2.09) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam (Mischung von syn-epimerem Racemat 1RS,4SR,9RS und anti-epimerem Racemat 1RS,4SR,9SR), (2.12) Isopyrazam (anti-epimeres Racemat 1RS,4SR,9SR), (2.13) Isopyrazam (anti-epimeres Enantiomer 1R,4S,9S), (2.14) Isopyrazam (anti-epimeres Enantiomer 1S,4R,9R), (2.15) Isopyrazam (syn-epimeres Racemat 1RS,4SR,9RS), (2.16) Isopyrazam (syn-epimeres Enantiomer 1R,4S,9R), (2.17) Isopyrazam (syn-epimeres Enantiomer 1S,4R,9S), (2.18) Mepronil, (2.19) Oxycarboxin, (2.20) Penflufen, (2.21) Penthiopyrad, (2.22) Sedaxan, (2.23) Thifluzamide, (2.24) 1-Methyl-N-[2-(1,1,2,2-tetrafluorethoxy)phenyl]-3-(trifluormethyl)-1H-pyrazol-4-carboxamid, (2.25) 3-(Difluormethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluorethoxy)phenyl]-1H-pyrazol-4-carboxamid, (2.26) 3-(Difluormethyl)-N-[4-fluor-2-(1,1,2,3,3,3-hexafluorpropoxy)phenyl]-1-methyl-1H-pyrazol-4-carboxamid, (2.27) N-[1-(2,4-Dichlorphenyl)-1-methoxypropan-2-yl]-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.28) 5,8-Difluor-N-[2-(2-fluor-4-{[4-(trifluormethyl)pyridin-2-yl]oxy}phenyl)ethyl]chinazolin-4-amin, (2.29) Benzovindiflupyr, (2.30) N-[(1S,4R)-9-(Dichlormethylen)-1,2,3,4-tetrahydro-1,4-methanonaphthalin-5-yl]-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.31) N-[(1R,4S)-9-(Dichlormethylen)-1,2,3,4-tetrahydro-1,4-methanonaphthalin-5-yl]-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.32) 3-(Difluormethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.33) 1,3,5-Trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.34) 1-Methyl-3-(trifluormethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.35) 1-Methyl-3-(trifluormethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.36) 1-Methyl-3-(trifluormethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.37) 3-(Difluormethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.38) 3-(Difluormethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.39) 1,3,5-Trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.40) 1,3,5-Trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.41) Benodanil, (2.42) 2-Chlor-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridin-3-carboxamid, (2.43) Isofetamid, (2.44) 1-Methyl-3-(trifluormethyl)-N-[2'-(trifluormethyl)biphenyl-2-yl]-1H-pyrazol-4-carboxamid, (2.45) N-(4'-Chlorbiphenyl-2-yl)-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.46) N-(2',4'-Dichlorbiphenyl-2-yl)-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.47) 3-(Difluormethyl)-1-methyl-N-[4'-(trifluormethyl)biphenyl-2-yl]-1H-pyrazol-4-carboxamid, (2.48) N-(2',5'-Difluorbiphenyl-2-yl)-1-methyl-3-(trifluormethyl)-1H-pyrazol-4-carboxamid, (2.49) 3-(Difluormethyl)-1-methyl-N-[4'-(prop-1-in-1-yl)biphenyl-2-yl]-1H-pyrazol-4-carboxamid, (2.50) 5-Fluor-1,3-dimethyl-N-[4'-(prop-1-in-1-yl)biphenyl-2-yl]-1H-pyrazol-4-carboxamid, (2.51) 2-Chlor-N-[4'-(prop-1-in-1-yl)biphenyl-2-yl]nicotinamid, (2.52) 3-(Difluormethyl)-N-[4'-(3,3-dimethylbut-1-in-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazol-4-carboxamid, (2.53) N-[4'-(3,3-Dimethylbut-1-in-1-yl)biphenyl-2-yl]-5-fluor-1,3-dimethyl-1H-pyrazol-4-carboxamid, (2.54) 3-(Difluormethyl)-N-(4'-ethinylbiphenyl-2-yl)-1-methyl-1H-pyrazol-4-carboxamid, (2.55) N-(4'-Ethinylbiphenyl-2-yl)-5-fluor-1,3-dimethyl-1H-pyrazol-4-carboxamid, (2.56) 2-Chlor-N-(4'-ethinylbiphenyl-2-yl)nicotinamid, (2.57) 2-Chlor-N-[4'-(3,3-dimethylbut-1-in-1-yl)biphenyl-2-yl]nicotinamid, (2.58) 4-(Difluormethyl)-2-methyl-N-[4'-(trifluormethyl)biphenyl-2-yl]-1,3-thiazol-5-carboxamid, (2.59) 5-Fluor-N-[4'-(3-hydroxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazol-4-carboxamid, (2.60) 2-Chlor-N-[4'-(3-hydroxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]nicotinamid, (2.61) 3-(Difluormethyl)-N-[4'-(3-methoxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazol-4-carboxamid, (2.62) 5-Fluor-N-[4'-(3-methoxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazol-4-carboxamid, (2.63) 2-Chlor-N-[4'-(3-methoxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]nicotinamid, (2.64) 1,3-Dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.65) 1,3-Dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.66) 1,3-Dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.67) 3-(Difluormethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorphenyl)propan-2-yl]-1H-pyrazol-4-carboxamid, (2.68) 3-(Difluormethyl)-N-(7-fluor-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazol-4-carboxamid, (2.69) 3-(Difluormethyl)-N-[(3R)-7-fluor-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazol-4-carboxamid, (2.70) 3-(Difluormethyl)-N-[(3S)-7-fluor-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazol-4-carboxamid. 3) Inhibitoren der Atmungskette am Komplex III, zum Beispiel (3.01) Ametoctradin, (3.02) Amisulbrom, (3.03) Azoxystrobin, (3.04) Cyazofamid, (3.05) Coumethoxystrobin, (3.06) Coumoxystrobin, (3.07) Dimoxystrobin, (3.08) Enoxastrobin, (3.09) Famoxadon, (3.10) Fenamidon, (3.11) Flufenoxystrobin, (3.12) Fluoxastrobin, (3.13) Kresoxim-methyl, (3.14) Metominostrobin, (3.15) Orysastrobin, (3.16) Picoxystrobin, (3.17) Pyraclostrobin, (3.18) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E)-2-(2-{[6-(3-Chlor-2-methylphenoxy)-5-fluorpyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamid, (3.24) (2E)-2-(Methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluormethyl)phenyl]ethyliden}amino)oxy]methyl}phenyl)acetamid, (3.25) (2E)-2-(Methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluormethyl)phenyl]ethoxy}imino)methyl]phenyl} acetamid, (3.26) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-Fluor-2-phenylvinyl]oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamid, (3.27) Fenaminostrobin, (3.28) 5-Methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluormethyl)phenyl]ethyliden}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-on, (3.29) (2E)-2-{2-[({Cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3-methoxyacrylsäuremethylester, (3.30) N-(3-Ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.31) 2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.32) 2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.33) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide. 4) Inhibitors of mitosis and cell division, for example (4.01) benomyl, (4.02) carbendazim, (4.03) chlorfenazole, (4.04) diethofencarb, (4.05) ethaboxam, (4.06) fluopicolide, (4.07) fuberidazole, (4.08) pencycuron, (4.09) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine, (4.14) 3-Chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine. 5) Compounds capable of attacking at multiple sites ("multisite action"), for example (5.01) Bordeaux mixture, (5.02) captafol, (5.03) captan, (5.04) chlorothalonil, (5.05)05) Copper hydroxide, (5.06) Copper naphthenate, (5.07) Copper oxide, (5.08) Copper oxychloride, (5.09) Copper(2+) sulfate, (5.10) Dichlofluanid, (5.11) Dithianone, (5.12) Dodine, (5.13) Dodine free base, (5.14) Ferbam, (5.15) Fluorofolpet, (5.16) Folpet, (5.17) Guazatine, (5.18) Guazatine acetate, (5.19) Iminoctadine, (5.20) Iminoctadinal besylate, (5.21) Iminoctadine triacetate, (5.22) Mancopper, (5.23) Mancozeb, (5.24) Maneb, (5.25) Metiram, (5.26) Metiram zinc, (5.27) Oxine-copper, (5.28) Propamidine, (5.29) Propineb, (5.30) Sulfur and sulfur preparations including calcium polysulfide, (5.31) Thiram, (5.32) Tolylfluanid, (5.33) Zineb, (5.34) Ziram, (5.35) Anilazine. 6) Compounds capable of inducing a host defense response, for example (6.01) Acibenzolar-S-methyl, (6.02) Isotianil, (6.03) Probenazole, (6.04) Tiadinil, (6.05) Laminarin. 7) Inhibitors of amino acid and / or protein biosynthesis, for example (7.01) Andoprim, (7.02) Blasticidin-S, (7.03) Cyprodinil, (7.04) Kasugamycin, (7.05) Kasugamycin hydrochloride hydrate, (7.06) Mepanipyrim, (7.07) Pyrimethanil, (7.08) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (7.09) Oxytetracycline, (7.10) Streptomycin. 8) Inhibitors of ATP production, for example (8.01) Fentin acetate, (8.02) Fentin chloride, (8.03) Fentin hydroxide, (8.04) Silthiofam. 9) Cell wall synthesis inhibitors, for example (9.01) Benthiavalicarb, (9.02) Dimethomorph, (9.03) Flumorph, (9.04) Iprovalicarb, (9.05) Mandipropamid, (9.06) Polyoxins, (9.07) Polyoxorim, (9.08) Validamycin A, (9.09) Valifenalate, (9.10) Polyoxin B, (9.11) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.12) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one. 10) Inhibitors of lipid and membrane synthesis, for example (10.01) biphenyl, (10.02) chloroneb, (10.03) dicloran, (10.04) edifenphos, (10.05) etridiazole, (10.06) iodocarb, (10.07) iprobenfos, (10.08) Isoprothiolane, (10.09) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14) tecnazene, (10.15) tolclofos-methyl. 11) Inhibitors of melanin biosynthesis, for example (11.01) carpropamide, (11.02) diclocymet, (11.03) fenoxanil, (11.04) phthalide, (11.05) pyroquilon, (11.06) tricyclazole, (11.07) 2,2,2-trifluoroethyl {3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate. 12) Inhibitors of nucleic acid synthesis, for example (12.01) Benalaxyl, (12.02) Benalaxyl-M (Kiralaxyl), (12.03) Bupirimate, (12.04) Clozylacon, (12.05) Dimethirimol, (12.06) Ethirimol, (12.07) Furalaxyl, (12.08) Hymexazole, (12.09) Metalaxyl, (12.10) Metalaxyl-M (Mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinic acid, (12.14) Octhilinone. 13) Signal transduction inhibitors, for example (13.01) chlozolinate, (13.02) fenpiclonil, (13.03) fludioxonil, (13.04) iprodione, (13.05) procymidone, (13.06) quinoxyfen, (13.07) vinclozolin, (13.08) proquinazid.14) Compounds that can act as uncouplers, for example (14.01) Binapacryl, (14.02) Dinocap, (14.03) Ferimzon, (14.04) Fluazinam, (14.05) Meptyldinocap. 15) Other compounds, for example (15.001) Benthiazol, (15.002) Bethoxazine, (15.003) Capsimycin, (15.004) Carvone, (15.005) Quinomethionate, (15.006) Pyriofenone (Chlazafenone), (15.007) Cufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Dazomet, (15.012) Debacarb, (15.013) Dichlorophen, (15.014) Diclomezin, (15.015) Difenzoquat, (15.016) Difenzoquat metilsulfate, (15.017) Diphenylamine, (15,018) Ecomat, (15,019) Fenpyrazamine, (15,020) Flumetover, (15,021) Fluoroimide, (15,022) Flusulfamide, (15,023) Flutianil, (15,024) Fosetyl aluminum, (15,025) Fosetyl calcium, (15,026) Fosetyl sodium, (15,027) Hexachlorobenzene, (15,028) Irumamycin, (15,029) Methasulfocarb, (15,030) Methyl isothiocyanate, (15,031) Metrafenone, (15,032) Mildiomycin, (15,033) Natamycin, (15,034) nickel dimethyl dithiocarbamate, (15.035) Nitrothal-isopropyl, (15.036) Oxamocarb, (15.037) Oxyfenthiin, (15.038) Pentachlorphenol und Salze, (15.039) Phenothrin, (15.040) phosphorige Säure und deren Salze, (15.041) Propamocarb-fosetylat, (15.042) Propanosin-Natrium, (15.043) Pyrimorph, (15.044) Pyrrolnitrin, (15.045) Tebufloquin, (15.046) Tecloftalam, (15.047) Tolnifanid, (15.048) Triazoxid, (15.049) Trichlamid, (15.050) Zarilamid, (15.051) 2-Methylpropansäure-(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-ylester, (15.052) 1-(4-{4-[(SR)-5-(2,6-Difluorphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]ethanon, (15.053) 1-(4-{4-[(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]ethanon, (15.054) Oxathiapiprolin, (15.055) 1H-Imidazol-1-carbonsäure-1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-ylester, (15.056) 2,3,5,6-Tetrachlor-4-(methylsulfonyl)pyridin, (15.057) 2,3-Dibutyl-6-chlorthieno[2,3-d]pyrimidin-4(3H)-on, (15.058) 2,6-Dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol-1,3,5,7(2H,6H)-tetron, (15.059) 2-[5-Methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanon, (15.060) 2-[5-Methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanon, (15.061) 2-[5-Methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanon, (15.062) 2-Butoxy-6-iod-3-propyl-4H-chromen-4-on, (15.063) 2-Chlor-5-[2-chlor-1-(2,6-difluor-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridin, (15.064) 2-Phenylphenol und Salze, (15.065) 3-(4,4,5-Trifluor-3,3-dimethyl-3,4-dihydroisochinolin-1-yl)chinolin, (15.066) 3,4,5-Trichlorpyridin-2,6-dicarbonsäurenitril, (15.067) 3-Chlor-5-(4-chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin, (15.068) 4-(4-Chlorphenyl)-5-(2,6-difluorphenyl)-3,6-dimethylpyridazin, (15.069) 5-Amino-1,3,4-thiadiazol-2-thiol, (15.070) 5-Chlor-N'-phenyl-N'-(prop-2-in-1-yl)thiophen-2-sulfonohydrazid, (15.071) 5-Fluor-2-[(4-fluorbenzyl)oxy]pyrimidin-4-amin, (15.072) 5-Fluor-2-[(4-methylbenzyl)oxy]pyrimidin-4-amin, (15.073) 5-Methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amin, (15.074) (2Z)-3-Amino-2-cyano-3-phenylacrylsäureethylester, (15.075) N'-(4-{[3-(4-Chlorbenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (15.076) N-(4-Chlorbenzyl)-3-[3-methoxy-4-(prop-2-in-1-yloxy)phenyl]propanamid, (15.077) N-[(4-Chlorphenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-in-1-yloxy)phenyl]propanamid, (15.078) N-[(5-Brom-3-chlorpyridin-2-yl)methyl]-2,4-dichlornicotinamid, (15.079) N-[1-(5-Brom-3-chlorpyridin-2-yl)ethyl]-2,4-dichlornicotinamid, (15.080) N-[1-(5-Brom-3-chlorpyridin-2-yl)ethyl]-2-fluor-4-iodnicotinamid, (15.081) N-{(E)-[(Cyclopropylmethoxy)imino][6-(difluormethoxy)-2,3-difluorphenyl]methyl}-2-phenylacetamid, (15.082) N-{(Z)-[(Cyclopropylmethoxy)imino][6-(difluormethoxy)-2,3-difluorphenyl]methyl}-2-phenylacetamid, (15.083) N'-{4-[(3-tert.-Butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chlor-5-methylphenyl}-N-ethyl-N-methylimidoformamid, (15.084) N-Methyl-2-(1-{[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalin-1-yl)-1,3-thiazol-4-carboxamid, (15.085) N-Methyl-2-(1-{[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalin-1-yl]-1,3-thiazol-4-carboxamid, (15.086) N-Methyl-2-(1-{[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalin-1-yl]-1,3-thiazol-4-carboxamid, (15.087) {6-[({[(1-Methyl-1H-tetrazol-5-yl)(phenyl)methylen]amino}oxy)methyl]pyridin-2-yl}-carbamidsäurepentylester, (15.088) Phenazin-1-carbonsäure, (15.089) Chinolin-8-ol, (15.090) Chinolin-8-olsulfat (2:1), (15.091) {6-[({[(1-Methyl-1H-tetrazol-5-yl)(phenyl)methylen]amino}-oxy)methyl]pyridin-2-yl}carbamidsäure-tert.-butylester, (15.092) (5-Brom-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanon, (15.093) N-[2-(4-{[3-(4-Chlorphenyl)prop-2-in-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamid, (15.094) 4-Oxo-4-[(2-phenylethyl)amino]butansäure, (15.095) {6-[({[(Z)-(1-Methyl-1H-tetrazol-5-yl)(phenyl)methylen]-amino}oxy)methyl]pyridin-2-yl}carbamidsäurebut-3-in-1-ylester, (15.096) 4-Amino-5-fluorpyrimidin-2-ol (tautomere Form: 4-Amino-5-fluorpyrimidin-2(1H)-on), (15.097) 3,4,5-Trihydroxybenzoesäurepropylester, (15.098) [3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.099) (S)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.100) (R)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.101) 2-Fluor-6-(trifluormethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamid, (15.102) 2-(6-Benzylpyridin-2-yl)chinazolin, (15.103) 2-[6-(3-Fluor-4-methoxyphenyl)-5-methylpyridin-2-yl]chinazolin, (15.104) 3-(4,4-Difluor-3,3-dimethyl-3,4-dihydroisochinolin-1-yl)chinolin, (15.105) Abscisinsäure, (15.106) N'-[5-Brom-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamid, (15.107) N'-{5-Brom-6-[1-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.108) N'-{5-Brom-6-[(1R)-1-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.109) N'-{5-Brom-6-[(1S)-1-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.110) N'-{5-Brom-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.111) N'-{5-Brom-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.112) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (15.113) N-Cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.114) N-(2-tert.-Butylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.115) N-(5-Chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.116) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.117) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.118) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(5-fluor-2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (15.119) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.120) N-(2-Cyclopentyl-5-fluorbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.121) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-fluor-6-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (15.122) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.123) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (15.124) N-Cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.125) N-(2-tert.-Butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.126) N-[5-Chlor-2-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.127) N-Cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-N-[5-methyl-2-(trifluormethyl)benzyl]-1H-pyrazol-4-carboxamid, (15.128) N-[2-Chlor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.129) N-[3-Chlor-2-fluor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.130) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.131) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carbothioamid, (15.132) N'-(2,5-Dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamid, (15.133) N'-{4-[(4,5-Dichlor-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamid, (15.134) N-(4-Chlor-2,6-difluorphenyl)-4-(2-chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.135) 9-Fluor-2,2-dimethyl-5-(chinolin-3-yl)-2,3-dihydro-1,4-benzoxazepin, (15.136) 2-{2-Fluor-6-[(8-fluor-2-methylchinolin-3-yl)oxy]phenyl}propan-2-ol, (15.137) 2-{2-[(7,8-Difluor-2-methylchinolin-3-yl)oxy]-6-fluorphenyl}propan-2-ol, (15.138) 4-(2-Chlor-4-fluorphenyl)-N-(2-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.139) 4-(2-Chlor-4-fluorphenyl)-N-(2,6-difluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.140) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.141) 4-(2-Brom-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.142) N-(2-Brom-6-fluorphenyl)-4-(2-chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.143) 4-(2-Brom-4-fluorphenyl)-N-(2-bromphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.144) 4-(2-Brom-4-fluorphenyl)-N-(2-brom-6-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.145) 4-(2-Brom-4-fluorphenyl)-N-(2-chlorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.146) N-(2-Bromphenyl)-4-(2-chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.147) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.148) 4-(2-Brom-4-fluorphenyl)-N-(2,6-difluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.149) 4-(2-Brom-4-fluorphenyl)-N-(2-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.150) N'-(4-{3-[(Difluormethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (15.151) N'-(2,5-Dimethyl-4-{3-[(1,1,2,2-tetrafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.152) N'-(2,5-Dimethyl-4-{3-[(2,2,2-trifluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.153) N'-(2,5-Dimethyl-4-{3-[(2,2,3,3-tetrafluorpropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.154) N'-(2,5-Dimethyl-4-{3-[(pentafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.155) N'-(4-{[3-(Difluormethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (15.156) N'-(2,5-Dimethyl-4-{[3-(1,1,2,2-tetrafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.157) N'-(2,5-Dimethyl-4-{[3-(2,2,2-trifluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.158) N'-(2,5-Dimethyl-4-{[3-(2,2,3,3-tetrafluorpropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.159) N'-(2,5-Dimethyl-4-{[3-(pentafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.160) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.161) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.162) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chlor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.163) 2-{3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethansulfonat, (15.164) 2-{3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorphenylmethansulfonat, (15.165) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.166) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.167) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-fluor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.168) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-fluor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.169) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-chlor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.170) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-chlor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.171) 2-{(5S)-3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethansulfonat, (15.172) 2-{(5R)-3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethansulfonat, (15.173) 2-{(5S)-3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorphenylmethansulfonat, (15.174) 2-{(5R)-3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorphenylmethansulfonat. . Biological pesticides as mixing partners

[0259] The compounds of formula (I) can be combined with biological pesticides.

[0260] Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and products formed by microorganisms, including proteins and secondary metabolites.

[0261] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria, and bacteria that act as biological insecticides, fungicides, or nematicides.

[0262] Examples of bacteria that are or can be used as biological pesticides are: Bacillus amyloliquefaciens, Strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM I-1562 or Bacillus firmus, Strain I-1582 (Accession number CNCM I-1582) or Bacillus pumilus,in particular strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, in particular strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis Strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No. NRRL B-50421) Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki Strain HD-1, or B. thuringiensis subsp. tenebrionis Strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (Accession Number ATCC SD- 5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus Strain AQ 6047 (Acession Number NRRL 30232).

[0263] Examples of fungi and yeasts that are or can be used as biological pesticides include: Beauveria bassiana, in particular strain ATCC 74040, Coniothyrium menitans,in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., in particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii ), especially strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea ), in particular strain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874), Paecilomyces lilacinus, in particular P. lilacinus Strain 251 (AGAL 89 / 030550), Talaromyces flavus, in particular strain V117b, Trichoderma atroviride, in particular strain SC1 (accession number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM I-952).

[0264] Examples of viruses that are or can be used as biological control agents are: Adoxophyes orana (Apple peel moth) Granulose virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (Cotton bollworm) Nuclear Polyhedrosis Virus (NPV), Spodoptera small(sugar beet moth) mNPV, Spodoptera frugiperda (Armyworm) mNPV, Spodoptera littoralis (African cottonworm) NPV.

[0265] It also includes bacteria and fungi that are added to plants, parts of plants, or organs as "inoculants" and that, through their special properties, promote plant growth and plant health. Examples include: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia ), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp..

[0266] Examples of plant extracts and products formed by microorganisms, including proteins and secondary metabolites, that are or can be used as biological control agents are: Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, Requiem™ Insecticide, Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, veratrine, Viscum album, Brassica extract, especially rapeseed or mustard powder. Safener as mixing partner

[0267] The compounds of formula (I) can be combined with safeners such as, for example, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Oxabetrinil, 2-Methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4). Plants and plant parts

[0268] According to the invention, all plants and plant parts can be treated. Plants are understood to mean all plants and plant populations, such as desirable and undesirable wild plants or cultivated plants (including naturally occurring cultivated plants), for example cereals (wheat, rice, triticale, barley, rye, oats), maize, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other vegetables, cotton, tobacco, rapeseed, and fruit plants (including apples, pears, citrus fruits, and grapes). Cultivated plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods, or combinations of these methods, including transgenic plants and including plant varieties that may or may not be protected by plant variety rights.Plant parts are understood to include all above-ground and below-ground parts and organs of the plant, such as shoots, leaves, flowers, and roots. Examples include leaves, needles, stems, trunks, flowers, fruiting bodies, fruits, and seeds, as well as roots, tubers, and rhizomes. Plant parts also include harvested material and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, slips, and seeds.

[0269] The treatment of plants and plant parts with the compounds of formula (I) according to the invention is carried out directly or by action on their environment, habitat or storage space according to the customary treatment methods, e.g. by dipping, spraying, evaporating, atomizing, scattering, painting, injecting and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.

[0270] As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, plant species and plant varieties, as well as parts thereof, that occur in the wild or that are obtained by conventional biological breeding methods such as crossing or protoplast fusion are treated. In a further preferred embodiment, transgenic plants and plant varieties obtained by genetic engineering methods, optionally in combination with conventional methods (genetically modified organisms), and their parts are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above. Particular preference is given to treating plants of the respective commercially available or commonly used plant varieties.Plant varieties are plants with new characteristics ("traits") that have been bred through conventional breeding, mutagenesis, or recombinant DNA techniques. These can be varieties, races, biotypes, and genotypes. Transgenic plant, seed treatment and integration events

[0271] The preferred transgenic (genetically engineered) plants or plant varieties to be treated according to the invention include all plants that have received genetic material through genetic modification that imparts particularly advantageous, valuable properties ("traits") to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity, increased flowering performance, easier harvesting, accelerated ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, and better storability and / or processability of the harvested products. Further and particularly highlighted examples of such properties are an increased ability of the plants to defend themselves against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, for example.by toxins produced in the plants, particularly those produced by the genetic material from Bacillus thuringiensis (e.g., by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb, and CryIF, as well as combinations thereof); furthermore, an increased defense capacity of the plants against plant-pathogenic fungi, bacteria, and / or viruses, brought about, for example, by systemically acquired resistance (SAR), systemin, phytoalexins, elicitors, as well as resistance genes and correspondingly expressed proteins and toxins; and an increased tolerance of the plants to certain herbicidal active ingredients, for example, imidazolinones, sulfonylureas, glyphosate, or phosphinothricin (e.g., the "PAT" gene). The genes conferring the desired traits can also occur in combination with one another in the transgenic plants.Examples of transgenic plants include important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other vegetables, cotton, tobacco, rapeseed, and fruit plants (including apples, pears, citrus fruits, and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco, and rapeseed. Traits highlighted include the plants' increased defense capacity against insects, arachnids, nematodes, and snails. Plant protection - types of treatment

[0272] The treatment of plants and plant parts with the compounds of formula (I) is carried out directly or by exposure to their environment, habitat or storage space using the customary treatment methods, e.g. by dipping, spraying, atomising, sprinkling, evaporating, atomising, misting, scattering, foaming, coating, spreading, injecting, watering (drenching), drip irrigation and, in the case of propagation material, in particular seeds, also by dry dressing, wet dressing, slurry dressing, encrusting, single- or multi-layer coating, etc. It is also possible to apply the compounds of formula (I) using the ultra-low-volume method or to inject the application form or the compound of formula (I) itself into the soil.

[0273] A preferred direct treatment of the plants is foliar application, ie compounds of formula (I) are applied to the foliage, whereby the treatment frequency and the application rate should be adjusted to the infestation pressure of the respective pest.

[0274] In the case of systemically active compounds, the compounds of formula (I) also reach the plants via the root system. The plants are then treated by the action of the compounds of formula (I) on the plant's habitat. This can be done, for example, by drenching, mixing into the soil or nutrient solution, i.e. the location of the plant (e.g. soil or hydroponic systems) is soaked with a liquid form of the compounds of formula (I), or by soil application, i.e. the compounds of formula (I) are introduced into the location of the plants in solid form (e.g. in the form of granules). In the case of water rice crops, this can also be done by dosing the compound of formula (I) in a solid application form (e.g. as granules) into a flooded rice field. Seed treatment

[0275] The control of animal pests by treating plant seeds has been known for a long time and is the subject of constant improvements. Nevertheless, a number of problems arise when treating seeds that cannot always be solved satisfactorily. It is therefore desirable to develop methods for protecting seeds and germinating plants that make the additional application of pesticides during storage, after sowing or after emergence of the plants unnecessary, or at least significantly reduce them. It is also desirable to optimise the amount of active ingredient used so that the seeds and germinating plants are protected as best as possible from infestation by animal pests, without, however, damaging the plant itself through the active ingredient used. In particular, methods for treating seeds should also take into account the intrinsic insecticidal ornematicidal properties of pest-resistant or pest-tolerant transgenic plants in order to achieve optimal protection of the seeds and the germinating plant with minimal use of pesticides.

[0276] The present invention therefore also relates in particular to a method for protecting seeds and germinating plants from pest attack by treating the seeds with one of the compounds of formula (I). The method according to the invention for protecting seeds and germinating plants from pest attack further comprises a method in which the seeds are treated simultaneously in one operation or sequentially with a compound of formula (I) and a mixing partner. It further also comprises a method in which the seeds are treated with a compound of formula (I) and a mixing partner at different times.

[0277] The invention also relates to the use of the compounds of formula (I) for treating seeds to protect the seeds and the resulting plant from animal pests.

[0278] The invention further relates to seed which has been treated with a compound of formula (I) to protect against animal pests. The invention also relates to seed which has been treated with a compound of formula (I) and a mixing partner at the same time. The invention further relates to seed which has been treated with a compound of formula (I) and a mixing partner at different times. In seed which has been treated with a compound of formula (I) and a mixing partner at different times, the individual substances can be contained in different layers on the seed. The layers containing a compound of formula (I) and a mixing partner can optionally be separated by an intermediate layer.The invention also relates to seed in which a compound of formula (I) and mixing partners are applied as a component of a coating or as a further layer or further layers in addition to a coating.

[0279] Furthermore, the invention relates to seed which, after treatment with a compound of formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.

[0280] One of the advantages that arise when one of the compounds of formula (I) acts systemically is that the seed treatment protects not only the seed itself but also the resulting plants from animal pests after emergence. This eliminates the need for immediate treatment of the crop at the time of sowing or shortly thereafter.

[0281] A further advantage is that treating the seed with a compound of formula (I) can promote germination and emergence of the treated seed.

[0282] It is also considered advantageous that compounds of formula (I) can also be used in particular in transgenic seeds.

[0283] Compounds of formula (I) can also be used in combination with signaling technology agents, resulting in better colonization with symbionts, such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi, and / or optimized nitrogen fixation.

[0284] The compounds of formula (I) are suitable for protecting seed of any plant variety used in agriculture, greenhouses, forestry, or horticulture. In particular, these are seeds of cereals (e.g., wheat, barley, rye, millet, and oats), maize, cotton, soybeans, rice, potatoes, sunflowers, coffee, tobacco, canola, rapeseed, beets (e.g., sugar beets and fodder beets), peanuts, vegetables (e.g., tomatoes, cucumbers, beans, brassicas, onions, and lettuce), fruit plants, lawns, and ornamental plants. Particular importance is attached to the treatment of seed of cereals (such as wheat, barley, rye, and oats), maize, soybeans, cotton, canola, rapeseed, and rice.

[0285] As already mentioned above, the treatment of transgenic seed with a compound of formula (I) is also of particular importance. This involves the seed of plants which generally contain at least one heterologous gene which controls the expression of a polypeptide with, in particular, insecticidal or nematicidal properties. The heterologous genes in transgenic seed can originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly suitable for the treatment of transgenic seed which contains at least one heterologous gene originating from Bacillus sp. Particularly preferably, this is a heterologous gene originating from Bacillus thuringiensis.

[0286] In the context of the present invention, the compound of formula (I) is applied to the seed. Preferably, the seed is treated in a state in which it is so stable that no damage occurs during treatment. In general, the seed can be treated at any time between harvest and sowing. Typically, seed is used which has been separated from the plant and freed from the cob, husks, stems, hull, wool or pulp. For example, seed can be used which has been harvested, cleaned and dried to a storable moisture content. Alternatively, seed can be used which has been treated with water after drying and then dried again, for example by priming.In the case of rice seed, it is also possible to use seed that has been pre-soaked in water to a certain stage (pigeon breast stage), for example, which leads to improved germination and more uniform emergence.

[0287] In general, when treating seeds, care must be taken to ensure that the amount of the compound of formula (I) and / or other additives applied to the seeds is selected so that seed germination is not impaired or the resulting plant is not damaged. This is especially important for active ingredients that can exhibit phytotoxic effects at certain application rates.

[0288] The compounds of formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.

[0289] The compounds of formula (I) can be converted into the usual seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seeds, as well as ULV formulations.

[0290] These formulations are prepared in a known manner by mixing compounds of formula (I) with customary additives, such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.

[0291] All dyes commonly used for such purposes are suitable as dyes that can be included in the mordant formulations used according to the invention. Both sparingly water-soluble pigments and water-soluble dyes can be used. Examples include the dyes known as Rhodamine B, CI Pigment Red 112, and CI Solvent Red 1.

[0292] Suitable wetting agents for use in the seed dressing formulations according to the invention include all wetting-promoting substances commonly used in the formulation of agrochemical active ingredients. Alkyl naphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates, are preferred.

[0293] Suitable dispersants and / or emulsifiers that can be present in the seed dressing formulations used according to the invention include all nonionic, anionic, and cationic dispersants commonly used for formulating agrochemical active ingredients. Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants are preferably used. Suitable nonionic dispersants include, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers, and tristyrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants include, in particular, ligninsulfonates, polyacrylic acid salts, and arylsulfonate-formaldehyde condensates.

[0294] Defoamers used in the seed dressing formulations according to the invention can include any foam-inhibiting substances commonly used in the formulation of agrochemical active ingredients. Silicone defoamers and magnesium stearate are preferred.

[0295] All substances used for such purposes in agrochemicals can be present as preservatives in the seed dressing formulations used according to the invention. Examples include dichlorophene and benzyl alcohol hemiformal.

[0296] Suitable secondary thickeners that can be included in the seed dressing formulations used according to the invention include all substances that can be used for such purposes in agrochemicals. Cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays, and highly dispersed silica are preferred.

[0297] Suitable adhesives for use in the mordant formulations according to the invention include all conventional binders used in mordants. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and Tylose are preferred.

[0298] Gibberellins that can be included in the seed dressing formulations used according to the invention are preferably gibberellins A1, A3 (= gibberellic acid), A4, and A7, with gibberellic acid being particularly preferred. Gibberellins are well known (cf. R. Wegler "Chemistry of Plant Protection and Pest Control Agents," Vol. 2, Springer Verlag, 1970, pp. 401-412).

[0299] The seed dressing formulations usable according to the invention can be used either directly or after prior dilution with water to treat a wide variety of seeds. Thus, the concentrates or the preparations obtainable from them by dilution with water can be used to dress cereal seeds such as wheat, barley, rye, oats, and triticale, as well as seeds of maize, rice, rapeseed, peas, beans, cotton, sunflowers, soybeans, and beets, or even vegetable seeds of various kinds. The seed dressing formulations usable according to the invention or their diluted application forms can also be used to dress seeds of transgenic plants.

[0300] All mixing devices commonly used for seed dressing can be used to treat seed with the seed dressing formulations used according to the invention or application forms prepared therefrom. In detail, the seed dressing procedure involves placing the seed in a mixer operating in batch or continuous mode, adding the desired amount of seed dressing formulation, either as such or after prior dilution with water, and mixing until the formulation is evenly distributed over the seed. A drying process may be required.

[0301] The application rate of the seed dressing formulations usable according to the invention can be varied within a wide range. It depends on the respective content of the compounds of formula (I) in the formulations and on the seed. The application rates for the compound of formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed. Animal health

[0302] In the field of animal health, i.e., the field of veterinary medicine, the compounds of formula (I) are effective against animal parasites, especially ectoparasites or endoparasites. The term endoparasites includes, in particular, helminths and protozoa such as coccidia. Ectoparasites are typically and preferably arthropods, especially insects and acarids.

[0303] In the field of veterinary medicine, the compounds of formula (I), which exhibit favorable toxicity to warm-blooded animals, are suitable for combating parasites that occur in animal breeding and husbandry in farm animals, breeding animals, zoo animals, laboratory animals, experimental animals, and companion animals. They are effective against all or individual developmental stages of the parasites.

[0304] Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer and especially cattle and pigs; poultry such as turkeys, ducks, geese and especially chickens; fish and crustaceans, e.g. in aquaculture, and also insects such as bees.

[0305] Pets include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and especially dogs, cats, house birds, reptiles, amphibians and aquarium fish.

[0306] According to a non-inventive embodiment, the compounds of formula (I) are administered to mammals.

[0307] According to a further non-inventive embodiment, the compounds of formula (I) are administered to birds, namely pet birds and in particular poultry.

[0308] The use of the compounds of formula (I) for combating animal parasites is intended to reduce or prevent disease, deaths and reduced performance (in meat, milk, wool, hides, eggs, honey and the like), thus enabling more economical and simpler animal husbandry and achieving better animal welfare.

[0309] In relation to the field of animal health, the term "control" or "controlling" means that the compounds of formula (I) can effectively reduce the occurrence of the respective parasite in an animal infected with such parasites to a harmless extent. More specifically, "controlling" in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth, or prevent its multiplication.

[0310] Arthropods include: from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; from the order Siphonapterida, for example Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; from the order Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.; as well as nuisances and hygiene pests from the order Blattarida. Arthropods also include:

[0311] From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., from the family Ixodidae, such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the original genus of multi-host ticks); from the order Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp.; and from the order Acaridida (Astigmata), for example Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp. Parasitic protozoa include:

[0312] Mastigophora (Flagellata), such as Trypanosomatidae, such as Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, wie zum Trichomona Beispiel, Beispie lampie, Giardia zoom, G. canis; Sarcomastigophora (Rhizopoda), such as Entamoebidae, eg Entamoeba histolytica, Hartmanellidae, eg Acanthamoeba sp., Harmanella sp.; Apicomplexa (Sporozoa), such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis, E. chinchillae, E. clupe, E. columba, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. media, E. maxima, E. magna. meleagridis , E .meleagrimitis, E. mitis, E. necatrix, E. ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec., E. stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec., I. suis, Cystisospora spec., Cryptosporidium spec., especially C. parvum; such as Toxoplasmadidae, for example Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; wie Sarcocystidae, zum Beispiel Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, wie Leucozoidae, zum Beispiel Leucozytozoon simondi, wie Plasmodiidae, zum Beispiel Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P. vivax, P. spec., wie Piroplasma, zum Beispiel Babesia argentina, B. cattle, B. canis, B. spec., Theileria parva, Theileria spec., wie Adeleina, zum Beispiel Hepatozoon canis, H. spec..

[0313] Pathogenic endoparasites, which are helminths, include flatworms (e.g., Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include: Monogenea: e.g.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.; Cestodes: from the order Pseudophyllidea e.g.: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp.; from the order Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp.; Trematodes: from the class Digenea for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp.; roundworms: Trichinellida, for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp.; from the order Tylenchida, for example: Micronema spp., Strongyloides spp.; from the order Rhabditida for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp.. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.; aus der Ordnung Spirurida zum Beispiel: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.; Acanthocephala: from the order Oligacanthorhynchida e.g.: Macracanthorhynchus spp., Prosthenorchis spp.; from the order Polymorphida e.g.: Filicollis spp.; from the order Moniliformida e.g.: Moniliformis spp.; from the order Echinorhynchida, for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.; Pentastoma: from the order Porocephalida, for example Linguatula spp.. .

[0314] In the field of veterinary medicine and animal husbandry, the compounds of formula (I) are administered by methods generally known in the art (not according to the invention), such as enterally, parenterally, dermally, or nasally in the form of suitable preparations. Administration can be prophylactic or therapeutic. Thus, one embodiment not according to the invention relates to the use of a compound of formula (I) as a medicament.

[0315] A further aspect relates to the use of a compound of formula (I) as an anti-endoparasitic (not according to the invention), in particular as a helminthicide or an anti-protozoal agent. Compounds of formula (I) are suitable for use as an anti-endoparasitic, in particular as a helminthicide or an anti-protozoal agent, for example in animal breeding, animal husbandry, stables, and the hygiene sector.

[0316] A further aspect relates to the use of a compound of formula (I) as an anti-endoparasitic (not according to the invention), in particular an arthropodicide such as an insecticide or an acaricide.

[0317] A further aspect relates to the use of a compound of formula (I) as an anti-endoparasitic (not according to the invention), in particular an arthropodicide such as an insecticide or acaricide, for example in animal husbandry, in animal breeding, in stables or in the hygiene sector. Anthelmintic mixture partners

[0318] Examples of anthelmintic mixture partners include: Anthelmintic active ingredients, including trematicide and cestocide active ingredients: from the class of macrocyclic lactones, e.g. E.g.: Abamectin, Doramectin, Emamectin, Eprinomectin, Ivermectin, Milbemycin, Moxidectin, Nemadectin, Selamectin; from the class of Benzimidazoles and Probenzimidazole,e.g. B.: Albendazole, albendazole sulfoxide, cambendazole, cyclobendazole, febantel, fenbendazole, flubendazole, mebendazole, netobimin, oxfendazole, oxibendazole, parbendazole, thiabendazole, thiophanate, triclabendazole; from the class of Cyclooctadepsipeptide, e.g.: Emodepside, PF1022; from the class of Aminoacetonitrile derivatives, e.g.: Monepantel; from the class of Tetrahydropyrimidines, e.g.: Morantel, Pyrantel, Oxantel; from the class of Imidazothiazoles, e.g.: butamisole, levamisole, tetramisole; from the class of Salicylanilides, e.g. B.: Bromoxanide, Brotianide, Clioxanide, Closantel, Niclosamide, Oxyclozanide, Rafoxanide, Tribromsalan; from the class of Paraherquamide, e.g. E.g.: Derquantel, paraherquamide; from the class of Aminophenylamidines, e.g.: Amidantel, deacylated amidantel (dAMD), tribendimidine; from the class of Organophosphates, e.g.: Coumaphos, Crufomat, Dichlorvos, Haloxon, Naphthalofos, Trichlorfon; from the class of substituted phenols,z. B.: Bithionol, Disophenol, Hexachlorophen, Niclofolan, Meniclopholan, Nitroxynil; from the class of the Piperazinones, z. B.: Praziquantel, Epsiprantel; among others various classes, z. B.: Amoscanate, Bephenium, Bunamidine, Clonazepam, Chlorsulon, Diamphenetide, Dichlorophene, Diethylcarbamazine, Emetin, Hetolin, Hycanthon, Lucanthon, Miracil, Mirasan, Niclosamide, Niridazole, Nitroxynil, Nitroscana, Ox, Oxalotin, Oxalotin, Oxalotin Paromomycin, Piperazine, Resorantel. Vector control

[0319] The compounds of formula (I) can also be used in vector control. A vector within the meaning of the present invention is an arthropod, in particular an insect or arachnid, capable of transmitting pathogens such as viruses, worms, protozoa, and bacteria from a reservoir (plant, animal, human, etc.) to a host. The pathogens can be transmitted either mechanically (e.g., trachoma by non-biting flies) to a host or by injection (e.g., malaria parasites by mosquitoes).

[0320] Examples of vectors and the diseases or pathogens they transmit are: 1) Mosquitoes Anopheles: malaria, filariasis; Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of worms; Aedes: yellow fever, dengue fever, filariasis, other viral diseases; Similia: transmission of worms, especially Onchocerca volvulus; 2) Lice: skin infections, spotted fever (epidemic typhus); 3) Fleas: plague, endemic spotted fever; 4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterial diseases; 5) Mites: acariasis, spotted fever, rickettsipox, tularemia, Saint-Louis encephalitis, viral meningitis (TBE), Crimean-Congo fever, Lyme disease; 6) Ticks: Borrelia diseases such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis).

[0321] Examples of vectors within the meaning of the present invention are insects such as aphids, flies, leafhoppers, or thrips, which can transmit plant viruses to plants. Other vectors that can transmit plant viruses are spider mites, aphids, beetles, and nematodes.

[0322] Further examples of vectors within the meaning of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, lice, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.

[0323] Vector control is also possible if the compounds of formula (I) are resistance-breaking.

[0324] Compounds of formula (I) are suitable for use in the prevention of diseases or pathogens transmitted by vectors. Thus, a further aspect of the present invention is the use of compounds of formula (I) for vector control, e.g., in agriculture, horticulture, forestry, gardens and recreational facilities, as well as in stored product and material protection. Protection of technical materials

[0325] The compounds of formula (I) are suitable for protecting technical materials against infestation or destruction by insects, e.g. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.

[0326] In the present context, technical materials are understood to mean non-living materials, such as, preferably, plastics, adhesives, glues, paper and cardboard, leather, wood, wood processing products, and paints. The application of the invention to the protection of wood is particularly preferred.

[0327] In a further embodiment, the compounds of formula (I) are used together with at least one further insecticide and / or at least one fungicide.

[0328] In a further embodiment, the compounds of formula (I) are present as a ready-to-use pesticide, i.e., they can be applied to the corresponding material without further modification. Other insecticides or fungicides that are particularly suitable are those mentioned above.

[0329] Surprisingly, it has also been found that the compounds of formula (I) can be used to protect objects, in particular ship hulls, screens, nets, structures, quays, and signaling systems, that come into contact with sea or brackish water from fouling. Likewise, the compounds of formula (I) can be used alone or in combination with other active ingredients as antifouling agents. Control of animal pests in the hygiene sector

[0330] The compounds of formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene, and stored product protection, especially for controlling insects, arachnids, and mites that occur in enclosed spaces, such as homes, factories, offices, and vehicle cabins. To control animal pests, the compounds of formula (I) are used alone or in combination with other active ingredients and / or adjuvants. They are preferably used in household insecticide products. The compounds of formula (I) are effective against sensitive and resistant species and against all developmental stages.

[0331] These pests include, for example, pests from the class Arachnida, from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.

[0332] They are used, for example, in aerosols, pressureless sprays, e.g. pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with evaporator plates made of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free or passive evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in scatter baits or bait stations. Preparation examples (compounds 1-30 are compounds according to the invention and compounds 31-74 are comparative examples): N-[5-Ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-pyridyl]-thioacetamide (Ex. 63)

[0333]

[0334] 71 mg (0.16 mmol) of N-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-pyridyl]acetamide were dissolved in 6 ml of toluene, 65.8 mg (0.16 mmol) of Lawesson's reagent (4-methoxyphenyldithiophosphonic anhydride) were added, and the mixture was stirred at 90°C for 3 h. Subsequently, a further 197.5 mg (0.48 mmol) of Lawesson's reagent were added, and the mixture was stirred at 90°C for 1 h. The solvent was distilled off in vacuo, and the residue was purified by column chromatography using a cyclohexane / ethyl acetate gradient (30:70 to 0:100) as the eluent. (logP (neutral): 2.41; MH +< : 444; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.19 (t, 3H), 2.74 (s, 3H), 3.68 (q, 2H), 3.91 (s, 3H), 8.31 (s, 1H), 8.59 (d, 1H), 9.30 (s, 1H), 9.35 (br. s, 1H), 12.69 (s, 1H). N-[5-Ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-pyridyl]acetamide

[0335] 774 mg (1.80 mmol) of 5-(ethylsulfonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-amine were initially charged with 220.8 mg (1.80 mmol) of 4-dimethylaminopyridine in a mixture of 20 ml each of pyridine and toluene, and 425.7 mg (5.42 mmol) of acetyl chloride were added. The reaction mixture was stirred for 45 min at 100°C, the solvent was distilled off under vacuum, and the residue was purified by column chromatography using cyclohexane / ethyl acetate as the eluent. (logP (neutral): 2.01; MH +< : 428; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.15 (t, 3H), 2.17 (s, 3H), 3.62 (q, 2H), 3.88 (s, 3H), 8.29 (s, 1H), 8.46-8.53 (m, 2H), 9.29 (s, 1H), 11.31 (s, 1H). N-{5-(Ethylsulfonyl)-6-[3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-yl}-2-methylpropanamid (Bsp. 16), beispielhaft genannt

[0336]

[0337] 54 mg (0.11 mmol) of 5-(ethylsulfonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-amine were dissolved in 4 ml of acetonitrile, 360 mg of pyridine (4.54 mmol) and 13.87 mg of 4-dimethylaminopyridine (0.11 mmol) were added, and the mixture was heated to 60°C. Subsequently, 123.4 mg (1.13 mmol) of 2-methylpropionyl chloride were added, the heating bath was removed, and the mixture was stirred overnight at room temperature. The mixture was diluted with 10 ml of dichloromethane, washed with 1 M hydrochloric acid solution, dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography using cyclohexane / ethyl acetate (1:1) as the eluent. (logP (neutral): 2.61; MH +< : 456; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.11-1.19 (m, 9H), 2.75-2.81 (m, 1H), 3.61 (q, 2H), 3.87 (s, 3H), 8.30 (s, 1H), 8.47 (d, 1H), 8.55 (d, 1H), 9.29 (s, 1H), 11.27 (s, 1H). 5-(Ethylsulfonyl)-6-[3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-amin (Bsp. 14)

[0338]

[0339] 118 mg (0.29 mmol) of 2-(6-chloro-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine were stirred with 3 ml of ethanol and 3 ml of 26% aqueous ammonia solution in a microwave for 6 h at 120°C and 15 bar. The mixture was freed from solvent under vacuum, and the residue was used directly in the next step. (logP (neutral): 1.62; MH +<: 386; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.13 (t, 3H), 3.46 (q, 2H), 3.82 (s, 3H), 6.76 (d, 1H), 7.42 (br. s., 2H), 7.93 (d, 1H), 8.24 (s, 1H), 9.23 (s, 1H). 2-(6-Chlor-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin (Bsp XIII-1)

[0340]

[0341] 900 mg (2.41 mmol) of 2-(6-chloro-3-ethylsulfanyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine were dissolved in 50 ml of dichloromethane, 555.6 mg (12.0 mmol) of formic acid and 1.64 g (16.8 mmol) of 35% hydrogen peroxide were added at room temperature, and the mixture was then stirred for 5 h at room temperature. The mixture was diluted with water and treated with sodium bisulfite solution, stirred for 1 h, and then treated with saturated sodium bicarbonate solution. The organic phase was separated, the aqueous phase was extracted twice with dichloromethane, and the combined organic phases were then freed from the solvent under vacuum. The residue was purified by column chromatography using preparative HPLC with a water / acetonitrile gradient as the eluent. (logP (neutral): 2.54; MH +< : 405; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.20 (t, 3H), 3.77 (q, 2H), 3.91 (s, 3H), 8.13 (d, 1H), 8.32 (s, 1H), 8.56 (d, 1H), 9.30 (s, 1H). 2-(6-Chlor-3-ethylsulfanyl-2-pyridyl)-3-methyl-6-(trifluormethyl)imidazo[4,5-c]-pyridin (Bsp. XI-1)

[0342]

[0343] 4.00 g (10.7 mmol) of 2-(3,6-dichloro-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine were dissolved in 60 ml of tetrahydrofuran, treated with 446 mg (11.1 mmol) of sodium hydride at -5°C, and stirred for 30 minutes at 0°C. Subsequently, 733 mg (11.8 mmol) of ethanethiol were added dropwise over 30 minutes at -5°C, the cooling bath was removed, and the mixture was stirred for 2 h at room temperature. The reaction mixture was hydrolyzed with water, the organic phase was separated, and the aqueous phase was extracted twice with ethyl acetate. The organic phases were combined, washed with sodium chloride solution, dried over sodium sulfate, and the solvent was then distilled off in vacuo. The residue was purified by stirring in methyl tert-butyl ketone / dichloromethane 25:1. (logP (neutral): 3.06; MH +< : 373 2-(3,6-Dichlor-2-pyridyl)-3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin (Bsp. IX-1)

[0344]

[0345] 20 g (104.6 mmol) of N-methyl-6-(trifluoromethyl)pyridine-3,4-diamine, 25.11 g (130.8 mmol) of 3,6-dichloropyridine-2-carboxylic acid, and 20.06 g (104.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) were stirred in 200 ml of pyridine for 8 h at 120 °C. The reaction mixture was freed from solvent under vacuum, water was added, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over sodium sulfate, and the solvent was then distilled off under vacuum. The residue was purified by column chromatography using a cyclohexane / ethyl acetate gradient as the eluent. (logP (neutral): 2.81; MH +<: 347; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 3.99 (s, 3H), 7.89 (d, 1H), 8.32 (s, 1H), 8.35 (d, 1H), 9.28 (s, 1H). N-{5-(Ethylsulfonyl)-6-[3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-yl}methansulfonamid (Bsp. 26)

[0346]

[0347] 66 mg (0.13 mmol) of 5-(ethylsulfonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-amine were dissolved in 5 ml of acetonitrile, 439 mg (5.54 mmol) of pyridine and 17.0 mg (0.13 mmol) of 4-dimethylaminopyridine were added, and 124.6 mg (0.69 mmol) of methanesulfonic anhydride was added dropwise under argon. The mixture was stirred for 2 h at room temperature, then another 124.6 mg (0.69 mmol) of methanesulfonic anhydride was added, and the mixture was stirred for 2 h at 60°C. The solvent was distilled off, the residue was dissolved in dichloromethane, and washed with 2 N hydrochloric acid solution. The aqueous phase was extracted twice with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was then distilled off in vacuo. The residue was purified by column chromatography using a water / acetonitrile gradient as the eluent.(logP (neutral): 0,85; MH +< : 464; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1,20 (t, 3H), 3,34 (s, 3H), 3,74 (q, 2H), 3,92 (s, 3H), 7,34 (d, 1H), 8,29 (s, 1H), 8,40 (d, 1H), 9,29 (s, 1H), 11,72 (s, 1H). 1-[5-Ethylsulfonyl-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]-2-pyridyl]-1,2-dimethyl-hydrazin (Bsp. 60)

[0348]

[0349] 102 mg (0.25 mmol) of 2-(6-chloro-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine were dissolved in 7 ml of acetonitrile under argon, 150.9 mg (1.09 mmol) of potassium carbonate and 103.8 mg (0.78 mmol) of 1,2-dimethylhydrazinium dichloride were added, and the mixture was stirred at room temperature for 4 h. The mixture was filtered, and the mother liquor was freed from the solvent. The residue was taken up in dichloromethane and washed once with water. The organic phase was dried over sodium sulfate, and the solvent was then distilled off in vacuo. (logP (neutral): 2.39; MH +< : 429; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.15 (t, 3H), 2.54 (d, 3H), 3.23 (s (3H), 3.54 (q, 2H), 3.87 (s, 3H), 5.24 (q, 1H), 7.37 (d, 1H), 8.02 (d, 1H), 8.25 (s, 1H), 9.25 (s, 1H). 2-(3,6-Difluorpyridin-2-yl)-3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin (Bsp. IX-2)

[0350]

[0351] 5.39 g (23.6 mmol) of N-methyl-6-(trifluoromethyl)pyridine-3,4-diamine, 4.90 g (30.8 mmol) of 3,6-difluoropyridine-2-carboxylic acid, and 4.54 g (23.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) were stirred in 50 ml of pyridine for 8 h at 120 °C. The reaction mixture was freed from solvent under vacuum, water was added, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over sodium sulfate, and the solvent was then distilled off under vacuum. The residue was purified by column chromatography using a cyclohexane / acetone gradient as the eluent.

[0352] logP (neutral): 2.11; MH +< : 315; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 4.14 (s, 3H), 7.60-7.64 (m, 1H), 8.27-8.33 (m, 2H), 9.28 (s, 1H). 2-[3-(Ethylsulfanyl)-6-fluorpyridin-2-yl]-3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin (Bsp. XI-2)

[0353]

[0354] 6.12 g (19.4 mmol) of 2-(3,6-difluoropyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine were dissolved in 200 ml of tetrahydrofuran, and 857 mg (21.4 mmol) of sodium hydride were added at 0 °C. Subsequently, 1.67 g (19.8 mmol) of sodium ethanethiolate were added, and the mixture was stirred overnight at room temperature. The reaction mixture was treated with water and extracted three times with ethyl acetate. The organic phases were combined, dried over sodium sulfate, and the solvent was distilled off in vacuo. The residue was purified by column chromatography using a cyclohexane / acetone gradient as the eluent.

[0355] logP (neutral): 2.73; MH +< : 357; 1H-NMR(400 MHz, D6-DMSO) δ ppm: 1.18 (t, 3H), 3.01 (q, 2H), 4.00 (s, 3H), 7.49-7.52 (m, 1H), 8.28-8.32 (m, 2H), 9.25 (s, 1H). 2-[3-(Ethylsulfonyl)-6-fluorpyridin-2-yl]-3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin (Bsp. XIII-2)

[0356]

[0357] 3.68 g (10.2 mmol) of 2-[3-(ethylsulfanyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine were dissolved in 100 ml of dichloromethane. At room temperature, 3.79 g (75%, 16.4 mmol) of meta-chloroperbenzoic acid were added, and the mixture was stirred overnight. Saturated sodium thiosulfate solution and then saturated sodium bicarbonate solution were added to the reaction mixture. The organic phase was separated, the aqueous phase was extracted twice with dichloromethane, and the combined organic phases were then freed from the solvent under vacuum. The residue was purified by column chromatography using preparative HPLC with a water / acetonitrile gradient as the eluent.

[0358] logP (neutral): 2.30; MH +< : 389; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.20 (t, 3H), 3.77 (q, 2H), 3.91 (s, 3H), 7.79-7.82 (m, 1H), 8.31 (s, 1H), 8.70-8.74 (m, 1H), 9.29 (s, 1H). 2-[6-Ethoxy-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin (Bsp. 10) beispielhaft genannt

[0359]

[0360] 23 µL (0.38 mmol) of ethanol were initially charged in 5 mL of tetrahydrofuran, and 15 mg (60%, 0.38 mmol) of sodium hydride were added. Then, 100 mg (0.25 mmol) of 2-[3-(ethylsulfonyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine were added, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture. The organic phase was separated, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were then freed from the solvent under vacuum. The residue was purified by column chromatography using preparative HPLC with a water / acetonitrile gradient as the eluent.

[0361] logP (neutral): 2.86; MH +< : 415; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.18 (t, 3H), 1.35 (t, 3H), 3.69 (q, 2H), 3.91 (s, 3H), 4.42 (q, 2H), 7.30 (d, 1H), 8.28 (s, 1H), 8.34 (d, 1H), 9.29 (s, 1H). 2-[6-(Ethylsulfanyl)-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin (Bsp. 5)

[0362]

[0363] 32 mg (0.38 mmol) of sodium ethanethiolate were initially charged in 5 ml of tetrahydrofuran, and 15 mg (60%, 0.38 mmol) of sodium hydride were added. Then, 100 mg (0.25 mmol) of 2-[3-(ethylsulfonyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine were added, and the mixture was stirred overnight at room temperature. Methanol was added to the reaction mixture, which was then evaporated to dryness. The residue was taken up with water and ethyl acetate. The organic phase was separated, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were then freed from the solvent under vacuum. The residue was purified by column chromatography using preparative HPLC with a water / acetonitrile gradient as the eluent.

[0364] logP (neutral): 3.14; MH +< : 431; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.19 (t, 3H), 1.30 (t, 3H), 3.20 (q, 2H), 3.71 (q, 2H), 3.90 (s, 3H), 7.82 (d, 1H), 8.25 (d, 1H), 8.29 (s, 1H), 9.29 (s, 1H). 2-[3,6-Bis(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin (Bsp. 15)

[0365]

[0366] 171 mg (0.39 mmol) of 2-[6-(ethylsulfanyl)-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine were dissolved in 7 ml of dichloromethane, then 101 mg (0.43 mmol) meta- Chloroperbenzoic acid was added, and the mixture was stirred at room temperature for 1 h. The mixture was washed once with saturated sodium thiosulfate solution and then with saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate, and the solvent was then distilled off in vacuo. The residue was purified by column chromatography using a water / acetonitrile gradient as the eluent.

[0367] logP (neutral): 2.27; MH +< : 463; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.18-1.26 (m, 6H), 3.59 (q, 2H), 3.90 (q, 2H), 3.95 (s, 3H), 8.33 (d, 1H), 8.56 (d, 1H), 8.89 (d, 1H), 9.31 (s, 1H). 2-[6-(Ethylsulfinyl)-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin (Bsp. 37)

[0368]

[0369] 171 mg (0.39 mmol) of 2-[6-(ethylsulfanyl)-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine were dissolved in 7 ml of dichloromethane, then 101 mg (0.43 mmol) meta- Chloroperbenzoic acid was added, and the mixture was stirred at room temperature for 1 h. The mixture was washed once with saturated sodium thiosulfate solution and then with saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate, and the solvent was then distilled off in vacuo. The residue was purified by column chromatography using a water / acetonitrile gradient as the eluent.

[0370] logP (neutral): 2.02; MH +< : 447; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.12 (t, 3H), 1.22 (t, 3H), 2.98-3.05 (m, 2H), 3.78-3.87 (m, 2H), 3.90 (s, 3H), 8.32 (s, 1H), 8.38 (d, 1H), 8.82 (d, 1H), 9.30 (s, 1H). 2-[6-(S-Ethylsulfonimidoyl)-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin (Bsp. 41)

[0371]

[0372] 76 mg (0.17 mmol) of 2-[6-(ethylsulfinyl)-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine were dissolved in 2 ml of acetonitrile, then 41 mg (0.20 mmol) of 4-nitrobenzenesulfonamide and 88 mg (0.27 mmol) of diacetoxyiodobenzene were added, and the mixture was stirred at 77 °C for 72 h. Then, another 88 mg (0.27 mmol) of diacetoxyiodobenzene was added, and the mixture was stirred at 77 °C for a further 72 h. The product was obtained and was purified by distilling off the solvent under vacuum and by column chromatography of the residue using a water / acetonitrile gradient as the eluent.

[0373] logP (neutral): 1,79; MH +< : 462; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1,19 (t, 3H), 1,25 (t, 3H), 3,39-3,51 (m, 2H), 3,90 (q, 2H), 3,94 (s, 3H), 8,34 (s, 1H), 8,54 (d, 1H), 8,85 (d, 1H), 9,32 (s, 1H). 2-[3-(Ethylsulfonyl)-6-(methylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin (Bsp. 28)

[0374]

[0375] 27 mg (0.38 mmol) of sodium methanethiolate were initially charged in 5 ml of tetrahydrofuran, and 15 mg (60%, 0.38 mmol) of sodium hydride were added. Then, 100 mg (0.25 mmol) of 2-[3-(ethylsulfonyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine were added, and the mixture was stirred overnight at room temperature. Methanol was added to the reaction mixture, which was then evaporated to dryness. The residue was taken up with water and ethyl acetate. The organic phase was separated, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were then freed from the solvent under vacuum. The residue was purified by column chromatography using a water / acetonitrile gradient as the eluent.

[0376] logP (neutral): 2.75; MH +< : 417; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.19 (t, 3H), 2.60 (s, 3H), 3.72 (q, 2H), 3.90 (s, 3H), 7.85 (d, 1H), 8.27 (d, 1H), 8.29 (s, 1H), 9.29 (s, 1H). [{5-(Ethylsulfonyl)-6-[3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-yl}(methyl)-lambda4-sulfanyliden]cyanamid (Bsp. 43)

[0377]

[0378] 410 mg (0.98 mmol) of 2-[3-(ethylsulfonyl)-6-(methylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine were initially charged in 40 ml of methanol, and 54 mg (1.28 mmol) of cyanamide and 133 mg (1.18 mmol) of potassium tert-butoxide were added. Then, 263 mg (1.47 mmol) of N-bromosuccinimide were added in portions, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, and then saturated sodium thiosulfate solution and dichloromethane were added. The organic phase was separated, the aqueous phase was extracted twice with dichloromethane, and the combined organic phases were then freed from the solvent under vacuum. The residue was purified by column chromatography using a water / acetonitrile gradient as the eluent.

[0379] logP (neutral): 1,75; MH +< : 457; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1,24 (t, 3H), 3,29 (s, 3H), 3,87-3,94 (m, 2H), 3,98 (s, 3H), 8,34 (s, 1H), 8,57 (d, 1H), 8,89 (d, 1H), 9,33 (s, 1H). 2-[6-(Benzylsulfanyl)-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin (Bsp. 30)

[0380]

[0381] 64 mg (0.51 mmol) of benzyl marcaptan were initially charged in 10 ml of tetrahydrofuran, and 31 mg (60%, 0.77 mmol) of sodium hydride were added. Then, 200 mg (0.51 mmol) of 2-[3-(ethylsulfonyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine were added, and the mixture was stirred overnight at room temperature. Methanol was added to the reaction mixture, which was then evaporated to dryness. The residue was taken up with water and ethyl acetate. The organic phase was separated, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were then freed from the solvent under vacuum. The residue was purified by column chromatography using a water / acetonitrile gradient as the eluent.

[0382] logP (neutral): 3,72; MH +< : 493; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1,18 (t, 3H), 3,69 (q, 2H), 3,80 (s, 3H), 4,49 (s, 2H), 7,23-7,39 (m, 5H), 7,87 (d, 1H), 8,27 (d, 1H), 8,30 (s, 1H), 9,29 (s, 1H). 5-(Ethylsulfonyl)-N-isopropyl-6-[3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-sulfonamid (Bsp. 49)

[0383]

[0384] 520 mg (1.05 mmol) of 2-[6-(benzylsulfanyl)-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine were placed in a mixture of 10 ml of dichloromethane, 2 ml of water, and 1 ml of acetic acid at 0 °C, and 624 mg (3.16 mmol) of 1,3-dichloro-5,5-dimethylhydantoin, dissolved in dichloromethane, was added dropwise. The mixture was stirred overnight at room temperature. The organic phase was separated, and the aqueous phase was extracted twice with dichloromethane. One-quarter of the combined organic dichloromethane solution was added dropwise to a solution of isopropylamine (0.028 ml, 0.33 mmol) in 2 ml of tetrahydrofuran at 0 °C. The mixture was stirred at room temperature for 3 h and then evaporated to dryness using a rotary evaporator. The residue was purified by column chromatography using a water / acetonitrile gradient as eluent.

[0385] logP (neutral): 2,49; MH +< : 492; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1,01 (d, 6H), 1,22 (t, 3H), 3,45-3,53 (m, 1H), 3,84 (q, 2H), 3,93 (s, 3H), 8,29 (bs, 1H), 8,35 (s, 1H), 8,45 (d, 1H), 8,82 (d, 1H), 9,35 (s, 1H). 2-{6-[(E)-2-Cyclopropylvinyl]-3-(ethylsulfonyl)pyridin-2-yl}-3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin (Bsp. 40)

[0386]

[0387] 100 mg (0,25 mmol) 2-(6-Chlor-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin, 48 mg (0,25 mmol) ( E)-2-Cyclopropylvinylboronic acid pinacol ester and 9 mg (0.007 mmol) of tetrakis(triphenylphosphine)palladium(0) were initially charged in a mixture of degassed dioxane (2 ml) and degassed sodium carbonate solution (1M, 1 ml) and stirred at 96°C for 16 h. The reaction mixture was then cooled to room temperature, concentrated in vacuo, and the residue was taken up in water and dichloromethane. The phases were separated, and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were then freed from the solvent, and the residue was purified by column chromatography using a water / acetonitrile gradient as the eluent.

[0388] logP (neutral): 3.24; MH +< : 437; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 0.67-0.69 (m, 2H), 0.91-0.96 (m, 2H), 1.18 (t, 3H), 1.72-1.76 (m, 1H), 3.69 (q, 2H), 3.86 (s, 3H), 6.60 (dd, 1H), 6.81 (d, 1H), 7.82 (d, 1H), 8.28 (s, 1H), 8.39 (d, 1H), 9.28 (s, 1H). Methyl-5-(ethylsulfonyl)-6-[3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-carboxylat (Bsp. 12)

[0389]

[0390] In an autoclave, 1.98 g (4.88 mmol) of 2-(6-chloro-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 749 mg (9.12 mmol) of sodium acetate, and 386 mg (0.48 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-acetone complex were placed in 100 ml of methanol and carbonylated for 15 h at 80 °C under a carbon monoxide atmosphere at a pressure of 10 bar. The reaction mixture was then cooled to room temperature, and the carbon monoxide atmosphere was removed. The reaction mixture was concentrated in vacuo, and the residue was taken up in water and dichloromethane. The phases were separated, and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were then freed from the solvent and the residue was purified by column chromatography using a water /

[0391] Purified using acetonitrile gradients as eluent.

[0392] logP (neutral): 2.17; MH +< : 429; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.20 (t, 3H), 3.81 (q, 2H), 3.89 (s, 3H), 3.96 (s, 3H), 8.32 (s, 1H), 8.54 (d, 1H), 8.75 (d, 1H), 9.30 (s, 1H). 5-(Ethylsulfonyl)-6-[3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-carbonsäure

[0393]

[0394] 944 mg (2.20 mmol) of methyl 5-(ethylsulfonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carboxylate were initially dissolved in 10 ml of ethanol, treated with 2.42 ml of sodium hydroxide solution (1M, 2.42 mmol), and stirred at room temperature for 30 min. The reaction mixture was concentrated in vacuo, and the residue was taken up in water. The mixture was then acidified with dilute hydrochloric acid, and the precipitated solid was filtered off with suction, washed with water, and dried.

[0395] logP (neutral): 0,76; MH +< : 415; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1,20 (t, 3H), 3,81 (q, 2H), 3,90 (s, 3H), 8,32 (s, 1H), 8,49 (d, 1H), 8,71 (d, 1H), 9,30 (s, 1H). 5-(Ethylsulfonyl)-N-methyl-6-[3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-carboxamid (Bsp. 31)

[0396]

[0397] 200 mg (0.48 mmol) of 5-(ethylsulfonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carboxylic acid were initially charged in 10 ml of dioxane, treated with 111 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 0.57 mmol), and stirred at room temperature for 1 h. Then, 0.24 ml of methanamine solution (2M in THF, 0.48 mmol) was added, and the reaction mixture was stirred at room temperature for 16 h. The mixture was concentrated in vacuo, and the residue was taken up in water and dichloromethane. The phases were separated, and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were then freed from the solvent and the residue was purified by column chromatography using a water / acetonitrile gradient as eluent.

[0398] logP (neutral): 1,96; MH +< : 428; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1,19 (t, 3H), 2,84 (d, 3H), 3,82 (q, 2H), 3,93 (s, 3H), 8,33 (s, 1H), 8,49 (d, 1H), 8,72 (d, 1H), 8,95-8,98 (m, 1H), 9,36 (s, 1H). 5-(Ethylsulfonyl)-N-methyl-6-[3-methyl-6-(trifluormethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-carbothioamid (Bsp. 34)

[0399]

[0400] 20 mg (0.05 mmol) of 5-(ethylsulfonyl)-N-methyl-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carboxamide were initially charged in 2 ml of toluene, treated with 8 mg (0.02 mmol) of Lawesson's reagent (4-methoxyphenyldithiophosphonic anhydride), and stirred under reflux for 10 h. Then, another 8 mg (0.02 mmol) of Lawesson's reagent was added, and the reaction mixture was stirred at 106 °C for 16 h. Subsequently, another 16 mg (0.04 mmol) of Lawesson's reagent was added, and the reaction mixture was stirred at 106 °C for another 16 h. The mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by column chromatography using a water / acetonitrile gradient as eluent.

[0401] logP (neutral): 2.76; MH +< : 444; 1< H-NMR(400 MHz, D 6 -DMSO) δ ppm: 1.20 (t, 3H), 3.22 (d, 3H), 3.80 (q, 2H), 3.92 (s, 3H), 8.33 (s, 1H), 8.70 (d, 1H), 8.88 (d, 1H), 9.36 (s, 1H).

[0402] In analogy to the examples and comparative examples and according to the preparation processes described above, the following compounds of formula (I) can be obtained (Examples 1-30 are according to the invention and Examples 31-74 are comparative examples): where the substituents R 1< , R 2a< , R 2b< , R 3< , A 1< , A 2< , A 4< and n have the meanings given in the following table: where the bond to the remaining molecule is marked with a wavy line.

[0403] The logP values ​​are measured in accordance with EEC Directive 79 / 831 Annex V.A8 using HPLC (High Performance Liquid Chromatography) on a reversed-phase column (C18). Temperature: 55°C.

[0404] The LC-MS determination in the acidic range is performed at pH 2.7 using 0.1% aqueous formic acid and acetonitrile (containing 0.1% formic acid) as eluents; a linear gradient from 10% acetonitrile to 95% acetonitrile is used. LogP (HCOOH) is listed in the table.

[0405] The LC-MS determination in the neutral range is performed at pH 7.8 using 0.001 molar aqueous ammonium bicarbonate solution and acetonitrile as eluents; a linear gradient from 10% acetonitrile to 95% acetonitrile is used. LogP (neutral) is indicated in the table.

[0406] Calibration is carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values ​​are known (determination of the logP values ​​from the retention times by linear interpolation between two consecutive alkanones).

[0407] The NMR data of selected examples are presented either in classical form (δ values, multiplet splitting, number of H atoms) or as NMR peak lists.

[0408] The solvent in which the NMR spectrum was recorded is indicated in each case. NMR peak list method

[0409] The 1< H NMR data of selected examples are recorded in the form of 1< H NMR peak lists. For each signal peak, the δ value in ppm is listed first, followed by the signal intensity in parentheses. The δ value - signal intensity pairs of different signal peaks are listed separated by semicolons.

[0410] The peak list of an example therefore has the form: δ 1 (intensity 1 )< ; δ 2 (intensity 2 );........; δ i (intensity i )< ; ...... ; δ n (intensity n )

[0411] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.

[0412] To calibrate the chemical shift of 1< H NMR spectra, we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may or may not be present in NMR peak lists.

[0413] The lists of 1< H NMR peaks are similar to the classical 1< H NMR printouts and thus usually contain all peaks listed in a classical NMR interpretation.

[0414] In addition, like classical 1< H-NMR printouts, they can show solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities.

[0415] When reporting compound signals in the delta region of solvents and / or water, our lists of 1< H NMR peaks show the common solvent peaks, for example, peaks of DMSO in DMSO-D 6 and the peak of water, which usually have high intensity on average.

[0416] The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have, on average, lower intensity than the peaks of the target compounds (e.g., with a purity of >90%).

[0417] Such stereoisomers and / or impurities may be typical for the respective manufacturing process. Their peaks can thus help identify the reproduction of our manufacturing process based on "byproduct fingerprints."

[0418] An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also empirically evaluated expected values) can isolate the peaks of the target compounds as needed, applying additional intensity filters if necessary. This isolation would be similar to the peak picking involved in classical 1< H NMR interpretation.

[0419] Further details on 1< H NMR peak lists can be found in the Research Disclosure Database Number 564025.

[0420] Anwendungsbeispiele (The compounds of Preparation Examples 1-30 are compounds according to the invention and the compounds of Preparation Examples 31-74 are comparison compounds) Phaedon cochleariae - Sprühtest

[0421]

[0422] To prepare a suitable active ingredient preparation, dissolve 1 part by weight of active ingredient with the specified parts by weight of solvent and make up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. To prepare further test concentrations, dilute with water containing emulsifier.

[0423] Chinese cabbage leaf slices (Brassica pekinensis) are sprayed with an active ingredient preparation of the desired concentration and after drying with larvae of the horseradish leaf beetle (Phaedon cochleariae) occupied.

[0424] After 7 days, the effectiveness is determined in %. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed. In this test, for example, the following compounds from the production examples show an effect of 100% at an application rate of 500g / ha: 1, 2, 3, 4, 6, 7, 8, 10, 13, 14, 15, 16, 21, 22, 24, 26, 27, 31, 32, 36, 37, 38, 40, 43, 46, 51, 52, 53, 54, 55, 56, 57, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 72, 74 In this test, for example, For example, the following compounds of the preparation examples show an effect of 83% at an application rate of 500g / ha: 9, 20 In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 100g / ha: 73 In this test, for example, the following compounds of the preparation examples show an effect of 83% at an application rate of 100g / ha: 33 Spodoptera frugiperda - Sprühtest

[0425]

[0426] To prepare a suitable active ingredient preparation, dissolve 1 part by weight of active ingredient with the specified parts by weight of solvent and make up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. To prepare further test concentrations, dilute with water containing emulsifier.

[0427] Corn leaf slices ( Zea mays ) are sprayed with an active ingredient preparation of the desired concentration and after drying with caterpillars of the armyworm ( Spodoptera frugiperda ) occupied.

[0428] After 7 days, the effectiveness is determined in %. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed. In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 500g / ha: 21, 40, 62, 64, 67 In this test, for example, the following compounds of the preparation examples show an effect of 83% at an application rate of 500g / ha: 10 Myzus persicae - Sprühtest

[0429]

[0430] To prepare a suitable active ingredient preparation, dissolve 1 part by weight of active ingredient with the specified parts by weight of solvent and make up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. To prepare further test concentrations, dilute with water containing emulsifier.

[0431] Chinese cabbage leaf slices ( Chinese cabbage ), which are affected by all stages of the green peach aphid ( Myzus persicae ) are sprayed with an active ingredient preparation of the desired concentration.

[0432] After 6 days, the effectiveness is determined in %. 100% means that all aphids have been killed; 0% means that no aphids have been killed. In this test, for example, the following compounds from the production examples show an effect of 100% at an application rate of 500g / ha: 3, 4, 16, 24, 31, 52, 55, 56, 61, 65, 70, 72 In this test, for example, the following compounds from the production examples show an effect of 90% at an application rate of 500g / ha: 2, 7, 8, 9, 10, 13, 14, 20, 21, 34, 36, 37, 38, 43, 44, 53, 57, 63, 64, 67, 69, 74 In this test, for example, For example, the following compounds of the preparation examples show an effect of 100% at an application rate of 100g / ha: 59 In this test, for example, the following compounds of the preparation examples show an effect of 90% at an application rate of 100g / ha: 60, 66 Tetranychus urticae - Sprühtest, OP-resistant

[0433]

[0434] To prepare a suitable active ingredient preparation, dissolve 1 part by weight of active ingredient with the specified parts by weight of solvent and make up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. To prepare further test concentrations, dilute with water containing emulsifier.

[0435] bean leaf slices (Phaseolus vulgaris), which are produced by all stages of the common spider mite (Nettle spider mite) are sprayed with an active ingredient preparation of the desired concentration.

[0436] After 6 days, the effectiveness is determined in %. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed. In this test, for example, the following compounds of the preparation examples show an activity of 100% at an application rate of 500g / ha: 31, 34, 67 In this test, for example, the following compounds of the preparation examples show an activity of 90% at an application rate of 500g / ha: 24, 33, 56, 58, 62, 74 In this test, for example, the following compounds of the preparation examples show an activity of 90% at an application rate of 100g / ha: 60 Meloidogyne incognita- Test

[0437]

[0438] To prepare a suitable preparation of active ingredient, mix 1 part by weight of active ingredient with the specified amount of solvent and dilute the concentrate with water to the desired concentration.

[0439] Vessels are filled with sand, active ingredient solution, an egg-larval suspension of the southern root-knot nematode ( Meloidogyne incognita)and lettuce seeds. The lettuce seeds germinate and the plants develop. Galls develop on the roots.

[0440] After 14 days, the nematicidal effect is determined based on the number of galls formed. 100% means no galls were found; 0% means the number of galls on the treated plants is the same as the untreated control. In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 20 ppm: 56, 65 In this test, for example, the following compounds of the preparation examples show an effect of 90% at an application rate of 20 ppm: 11, 14, 18, 29, 62 Boophilus microplus -Injektionstest

[0441] Solvent: Dimethyl sulfoxide

[0442] To prepare a suitable preparation of active ingredients, mix 10 mg of active ingredient with 0.5 ml of solvent and dilute the concentrate with solvent to the desired concentration.

[0443] 1µl of the active ingredient solution is injected into the abdomen of 5 fully engorged, adult, female cattle ticks (Boophilus microplus) injected. The animals are transferred to trays and kept in a climate-controlled room.

[0444] The efficacy test is carried out after 7 days for the laying of fertile eggs. Eggs whose fertility is not externally visible are stored in a climate-controlled cabinet until the larvae hatch after approximately 42 days. An efficacy of 100% means that none of the ticks have laid fertile eggs; 0% means that all eggs are fertile. In this test, for example, the following compounds from the preparation examples show an efficacy of 80% at an application rate of 20µg / animal: 14, 22 Ctenocephalides felis - Oraltest

[0445]

[0446] To prepare a suitable preparation of active ingredients, mix 10 mg of active ingredient with 0.5 ml of dimethyl sulfoxide. The desired concentration is obtained by diluting with citrated bovine blood.

[0447] Approx. 20 fasting adult cat fleas ( Ctenocephalides felis ) are placed in a chamber sealed at the top and bottom with gauze. A metal cylinder, the bottom of which is sealed with parafilm, is placed on top of the chamber. The cylinder contains the blood drug preparation, which the fleas can absorb through the parafilm membrane.

[0448] After 2 days, the kill rate is determined in %. 100% means that all fleas were killed; 0% means that none were killed. In this test, the following compounds from the preparation examples, for example, show a 100% kill rate at a rate of 100 ppm: 8, 14, 22 Lucilia cuprina - Test

[0449]

[0450] To prepare a suitable preparation of active ingredients, mix 10 mg of active ingredient with 0.5 ml of dimethyl sulfoxide and dilute the concentrate with water to the desired concentration.

[0451] Approximately 20 L1 larvae of the Australian golden sheep fly ( Lucilia cuprina ) are transferred into a test vessel containing minced horse meat and the active ingredient preparation of the desired concentration.

[0452] After 2 days, the kill rate is determined in %. 100% means that all larvae were killed; 0% means that no larvae were killed. In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 100 ppm: 8, 10, 14 In this test, for example, the following compounds of the preparation examples show an effect of 90% at an application rate of 100 ppm: 22 Musca domestica-Test

[0453]

[0454] To prepare a suitable preparation of active ingredients, mix 10 mg of active ingredient with 0.5 ml of dimethyl sulfoxide and dilute the concentrate with water to the desired concentration.

[0455] Vessels containing a sponge treated with sugar solution and the active ingredient preparation of the desired concentration are inoculated with 10 adult houseflies (Housefly) occupied.

[0456] After 2 days, the kill rate is determined in percent. 100% means all flies were killed; 0% means none were killed. In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 100 ppm: 8, 22 In this test, for example, the following compounds of the preparation examples show an effect of 90% at an application rate of 100 ppm: 10 Myzus persicae - Spray test

[0457]

[0458] To prepare a suitable active ingredient preparation, dissolve 1 part by weight of active ingredient with the specified parts by weight of solvent and dilute with water containing an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier. If ammonium salts and / or penetration enhancers are required, these are each added to the preparation solution at a concentration of 1000 ppm.

[0459] Pepper plants ( Red pepper ) , which is heavily affected by the green peach aphid ( Myzus persicae ) are treated by spraying with the active ingredient preparation in the desired concentration.

[0460] After 6 days, the kill rate is determined in %. 100% means that all lice were killed; 0% means that no lice were killed. In this test, for example, the following compounds from the preparation examples show 100% efficacy at an application rate of 100 ppm: 22, 40 Ctenocephalides felis - in-vitro Kontakttests mit adulten Katzenflöhen

[0461] To coat the test tubes, first dissolve 9 mg of active ingredient in 1 ml of acetone pa and then dilute it with acetone pa to the desired concentration. 250 µl of the solution is homogeneously distributed over the inner walls and bottom of a 25 ml glass tube by rotating and tilting on a rotary shaker (rocking rotation for 2 hours at 30 rpm). With 900 ppm of active ingredient solution and an internal surface area of ​​44.7 cm², a homogeneous distribution results in a surface dose of 5 µg / cm².

[0462] After evaporation of the solvent, the vials are filled with 5-10 adult cat fleas ( Ctenocephalides felis), sealed with a perforated plastic lid, and incubated horizontally at room temperature and ambient humidity. Efficacy is determined after 48 hours. To do this, the vials are placed upright and the fleas are tapped to the bottom of the vial. Fleas that remain motionless on the floor or move in an uncoordinated manner are considered dead or injured.

[0463] A substance shows good effect against Ctenocephalides felis, if at least 80% efficacy was achieved in this test at an application rate of 5 µg / cm 2 <. 100% efficacy means that all fleas were affected or dead. 0% efficacy means that no fleas were harmed. In this test, for example, the following compounds from the preparation examples show 100% efficacy at an application rate of 5 µg / cm 2 < (500 g / ha): 22 Anopheles Test (ANPHGB Oberflächenbehandlung) Solvent: Acetone + 2000 ppm rapeseed oil methyl ester (RME)

[0464] To prepare a suitable active ingredient preparation, the active ingredient is dissolved in a solvent (2 mg / ml). The active ingredient preparation is pipetted onto a glazed tile. After drying, adult mosquitoes of the species Anopheles gambiae strain RSPH (homozygous kdr) are placed on the treated tile. The exposure time is 30 minutes.

[0465] 24 hours after contact with the treated surface, mortality is determined in %. 100% means that all mosquitoes were killed; 0% means that no mosquitoes were killed. In this test, for example, the following compounds of the preparation examples show an effect of 80-100% at an application rate of 100mg / m 2< : 14 In this test, for example, the following compounds of the preparation examples show an effect of 80-100% at an application rate of 20mg / m 2< : 14 Anopheles Test (ANPHFU Oberflächenbehandlung) Solvent: Acetone + 2000 ppm rapeseed oil methyl ester (RME)

[0466] To prepare a suitable preparation, the active ingredient is dissolved in the solvent (2 mg / ml). The preparation is pipetted onto a glazed tile. After drying, adult mosquitoes of the species Anopheles funestus strain FUMOZ-R (Hunt et al., Med Vet Entomol. 2005 Sep; 19(3):271-5) are placed on the treated tile. The exposure time is 30 minutes.

[0467] 24 hours after contact with the treated surface, mortality is determined in %. 100% means that all mosquitoes were killed; 0% means that no mosquitoes were killed. In this test, for example, the following compounds of the preparation examples show an effect of 80-100% at an application rate of 100mg / m 2< : 14 In this test, for example, the following compounds of the preparation examples show an effect of 80-100% at an application rate of 20mg / m 2< : 14 Aedes Test (AEDSAE Oberflächenbehandlung) Solvent: Acetone + 2000 ppm rapeseed oil methyl ester (RME)

[0468] To prepare a suitable preparation, the active ingredient is dissolved in a solvent (2 mg / ml). The preparation is pipetted onto a glazed tile. After drying, adult mosquitoes of the species Aedes aegypti strain Monheim are placed on the treated tile. The exposure time is 30 minutes.

[0469] 24 hours after contact with the treated surface, mortality is determined in %. 100% means that all mosquitoes were killed; 0% means that no mosquitoes were killed. In this test, for example, the following compounds of the preparation examples show an effect of 80-100% at an application rate of 100mg / m 2< : 14 In this test, for example, the following compounds of the preparation examples show an effect of 80-100% at an application rate of 20mg / m 2< : 14

Claims

1. Compounds of the formula (I) where the substituents R1, R2a, R2b, R3, A1, A2, A4 and n have the meanings given in the table below:

2. Compounds of the formula (IX) in which R2a, R3, A1, A2 and A4 have the meanings given in Claim 1 and X1 or X2 represents halogen.

3. Compounds of the formula (XI) in which A1, A2, A4, R1, R2a, R3 have the meanings described above; X1 represents halogen.

4. Compounds of the formula (XII) in which A1, A2, A4, R1, R2a, R3 have the meanings described above; X1 represents halogen.

5. Agrochemical formulation comprising compounds of the formula (I) according to Claim 1, and extenders and / or surfactants.

6. Agrochemical formulation according to Claim 5, additionally comprising a further agrochemically active compound.

7. Method for controlling animal pests, characterized in that a compound of the formula (I) according to Claim 1 or an agrochemical formulation according to Claim 5 or 6 is allowed to act on the animal pests and / or their habitat, excluding methods of therapeutic or surgical treatment of the human or animal body.

8. Use of compounds of the formula (I) according to Claim 1 or of agrochemical formulations according to Claim 5 or 6 for controlling animal pests, excluding use in methods of therapeutic or surgical treatment of the human or animal body.