Substituted sulfonamides for controlling animal pests

Abstract

The present invention relates to compounds of formula (I), in which R1 and R2 have the meanings given in the description, to their use for controlling animal pests, in particular nematodes, to a method for controlling animal pests, and to an agrochemical formulation comprising the compound of formula (I).

Description

[0001] BYC240191 Foreign AF / CP 2026-03-25

[0002] -1- SUBSTITUTED SULFONYLAMIDES FOR THE CONTROL OF ANIMAL PESTS

[0003] The present application relates to substituted sulfonylamides and their use for controlling animal pests, in particular nematodes, a method for controlling animal pests and an agrochemical formulation containing the substituted sulfonylamides.

[0004] Sulfonylamides and their suitability as active ingredients are described in the literature, for example in patent applications WO 2005 / 099705, WO 2003 / 040107, WO 2014 / 077285 and WO 2014 / 023367.

[0005] Furthermore, it is known, for example, from documents WO 2010 / 129500, WO 2012 / 054233, WO 2013 / 055584, WO 2014 / 109933, WO 2015 / 007668, WO 2015 / 011082, WO 2015 / 169776, WO 2018 / 083288 and WO2021 / 089673, that certain sulfonylamides can be used as nematicides. EP 2092824 also discloses sulfonylamides that can be used as insecticides.

[0006] Modern nematicides and insecticides must meet numerous requirements, such as the intensity, duration, and breadth of their effects and their potential applications. Factors such as toxicity, the protection of beneficial insects and pollinators, environmental properties, application rates, compatibility with other active ingredients or formulation aids, and the effort required for synthesis all play a role. Furthermore, resistance can develop, to name just a few parameters. For all these reasons, the search for new plant protection products cannot be considered complete, and there is a constant need for new compounds with properties equivalent to, or at least improved upon in certain aspects, those of known compounds.

[0007] The object of the present invention was to provide compounds for use in the control of animal pests, thereby supplementing the range of pest control agents in various aspects.

[0008] The problem, as well as other unexplained problems that can be derived or deduced from the contexts discussed herein, will be solved by providing connections of formula (I)

[0009]

[0010] (I),BYC240191 Abroad

[0011] - 2 -in the

[0012] R 1 stands for chlorine or methyl, and

[0013] R 2 for (Ci-C6)-alkyl, (Ci-C4)-alkoxy-(Ci-C2)-alkyl, (Ci-C4)-alkoxy-(C2-C4)-alkoxy-(Ci-C2)-alkyl, (C3-C5)-cycloalkyl-(Ci-C2)-alkyl, (C3-C5)-cycloalkyl or (Ci-C4)-haloalkoxy-(Ci-C2)-alkyl stands.

[0014] Preferably, formula (I)

[0015] R 1for chlorine and

[0016] R 2 for Methyl, Ethyl, Isopropyl, Methoxymethyl or Difluoromethoxymethyl.

[0017] In one embodiment of the invention, formula (I)

[0018] R 1 for chlorine and

[0019] R 2 for methyl or methoxymethyl.

[0020] In a preferred embodiment of the invention, the compounds of formula (I) according to the above described configurations and preferred embodiments are used to control animal pests, in particular nematodes.

[0021] According to a further preferred embodiment of the invention, the use of a compound according to formula (I) in accordance with the above described configurations and preferred embodiments is provided for the protection of the propagation material of plants.

[0022] Another object of the invention is a method for controlling animal pests, preferably nematodes, in which at least one compound according to formula (I) according to the above described embodiments and preferred configurations, or an agent according to the invention, is applied to the animal pests, preferably nematodes, and / or their habitat.

[0023] According to a preferred embodiment of the method, surgical, therapeutic and diagnostic treatment of the human or animal body is excluded.

[0024] A further object of the invention is an agrochemical formulation containing at least one compound according to formula (I) according to the embodiments and preferred configurations described above, in a biologically active amount of 0.00000001 to 98 wt.%, based on the weight of the agrochemical formulation, as well as extenders and / or surfactants. BYC240191 Abroad

[0025] - 3 - A preferred embodiment of the formulation according to the invention additionally contains a further agrochemical active ingredient.

[0026] Definitions

[0027] By definition, unless otherwise specified, halogen is selected from the series fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine.

[0028] Unless otherwise defined elsewhere, the term "(Ci-C6)-alkyl" within the scope of the present invention refers to a residue of a saturated, aliphatic hydrocarbon group having 1 to 6 carbon atoms, which may be branched or unbranched. Preferably, it is a hydrocarbon chain having 1, 2, 3, or 4 carbon atoms ("Ci-C4-alkyl"). Examples of (Ci-C4)-alkyl residues are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl. The term "(Ci-C4)-alkoxy", either alone or in combination with other terms, such as "(Ci-C4)-alkoxy-(Ci-C2)-alkyl" or "(Ci-C4)-haloalkoxy-(Ci-C2)-alkyl", refers in this context to a residue -O-(Ci-C4)-alkyl, whereby the term "(Ci-C4)-alkyl" has the meaning given above.Examples of (Ci-C4) alkoxy radicals are methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), n-butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (iso-butoxy) and 1,1-dimethylethoxy (tert-butoxy).

[0029] Halogen-substituted residues, e.g., (Ci-C4)-haloalkoxy, are singly or multiply halogenated up to the maximum possible number of substituents. In the case of multiple halogenation, the halogen atoms can be the same or different. Examples of (Ci-C4)-haloalkoxy residues are chlormethoxy, bromomethoxy, dichlormethoxy, trichlormethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorfluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, and 2,2,2-trifluoroethoxy.

[0030] The term "(C3-C5)-cycloalkyl" refers to a saturated, monocyclic hydrocarbon ring with 3, 4, or 5 carbon atoms. Examples of (C3-C5)-cycloalkyl groups include cyclopropyl, cyclobutyl, and cyclopentyl.

[0031] The residues "(Ci-C4)-alkoxy-(Ci-C2)-alkyl", "(Ci-C4)-halogenalkoxy-(Ci-C2)-alkyl", "(Ci-C4)-alkoxy-(C2-C4)-alkoxy-(Ci-C2)-alkyl" and "(C3-C5)-cycloalkyl-(Ci-C2)-alkyl" represent a (C1-C4)-alkoxy-, (Ci-C4)-halogenalkoxy-, (Ci-C4)-alkoxy-(C2-C4)-alkoxy- or (C3-C5)-cycloalkyl residue, respectively, which is linked via a -CH2-, -(CTE^- or -CH(CH3)- group (linker) to the rest of the molecule according to formula (I). BYC240191 Abroad

[0032] - 4 - Explanation of the processes and intermediates

[0033] The preparation of compounds of formula (I) is explained in the following formula diagrams by way of example and supplementary information. Reference is also made here to the preparation examples.

[0034] Formula scheme 1

[0035]

[0036] The preparation of compounds of formula (I) according to the invention is carried out in general in accordance with the information in WO 2018 / 083288.

[0037] Formula scheme 1 describes the preparation of compounds of formula (I) according to the invention starting from carboxylic acids of formula (II) by generally known methods by reaction with a coupling reagent and sulfonamides of formula (III), see for example WO2012 / 80447, W02006 / 114313, WO2015 / 11082, W02010 / 129500, US2008 / 227769 and W02009 / 67108.

[0038] The required sulfonamides are known or can be prepared using generally known methods. The sulfonamides can be obtained from the corresponding sulfochlorides by reaction with ammonia; see WO2014 / 146490, R. Gao et al., Eur. J. Med. Chem. 2013, 62, 597-604; Q.-H. Chen et al., Bioorg. Med. Chem. 2005, 13 (7), 2459-2468.

[0039] Examples include:

[0040] 2-Chloro-5-methylbenzenesulfonamide: CFH Allen et al., J. Org. Chem 1942, 7, 15-18.

[0041] 2-Chloro-5-isopropylbenzenesulfonamide: E. Ellingboe et al., Journal of the American Chemical Society 1933, 55 (7), 2960-2966.

[0042] 2-Chloro-5-(methoxymethyl)benzenesulfonamide is obtained from 2-chloro-5-(hydroxymethyl)benzenesulfonamide, the preparation of which is described in W02005 / 82890, by first converting the alcohol fusion with thionyl chloride in ethyl acetate to the corresponding chloride and then with sodium methylate in THF to the methyl ether. BYC240191 Abroad

[0043] - 5 - 2-Chloro-5-[(difluoromethoxy)methyl]benzenesulfbenamide is obtained from 4-chloro-3-sulfamoylbenzoic acid methyl ester (see for example W02005 / 082890) by generally known methods. First, this is reduced to 2-chloro-5-(hydroxymethyl)benzenesulfonamide (see, for example, W02005 / 082890). Then, according to, for example, W02015 / 007668, the silyl ether 5-({[tert-butyl(dimethyl) silyl] oxy(methyl)-2-chlorobenzenesulfonamide} is obtained, and from this, with dimethylformamide dimethyl acetal, the amidine N'-{[5-({[tert-butyl(dimethyl) silyl] oxy}methyl)-2-chlorophenyl]sulfonyl}-N,N-dimethylimidoformamide is obtained. The silyl ether is cleaved with KF-HF in methanol upon heating to give the alcohol N'-{[2-chloro-5-(hydroxymethyl)phenyl]sulfonyl}-N,N-dimethylimidoformamide.This is reacted in dichloromethane / water in the presence of potassium acetate with (bromodifluoromethyl)trimethylsilane to give the difluoromethyl ether N'-({2-chloro-5-[(difluoromethoxy)methyl]phenyl(sulfonyl)-N,N-dimethylimidoformamide}. Subsequently, the amidine is cleaved by reaction with hydrazine hydrate in ethanol to give the sulfonamide 2-chloro-5-[(difluoromethoxy)methyl]benzenesulfonamide.

[0044] The carboxylic acid of formula (II) is obtained according to formula scheme 2.

[0045] Formula scheme 2

[0046]

[0047] The imidazole ester (IV) is obtained by reaction with 1,1,1,3-tetrachloropropane and potassium carbonate in, for example, acetonitrile, dimethyl sulfoxide, or dimethylformamide, analogous to the procedure described by N.M. Davtayan et al., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, pp. 546–549, to give the ester (V). The separation of the resulting isomer, methyl-1-(3,3-dichloroprop-2-en-1-yl)-1H-imidazole-5-carboxylate, is possible by normal-phase chromatography or, if necessary, by repeated precipitation from, for example, mixtures of dichloromethane and / or acetone and cyclohexane. By reaction with N-chlorosuccinimide in acetonitrile or DMF, the ester BYC240191 is obtained analogously to the procedure according to C.L. Meena et al., Eur. J. Med. Chem. 2016, 111 (23), 72-83.

[0048] - 6 - (VI) is obtained, from which acid (II) is prepared by ester hydrolysis with sodium hydroxide in, for example, water / methanol. Further purification of acid (II) is possible by dissolving it in an aqueous solution of potassium carbonate, heating it to approximately 60°C for about 20 minutes, precipitating it after cooling by acidification with formic acid, and filtering it off.

[0049] See also the manufacturing examples.

[0050] Salts

[0051] The compounds of formula (I) can also exist as salts, in particular acid addition salts or metal salt complexes. The compounds of formula (I) and their acid addition salts and metal salt complexes are highly effective, especially for controlling animal pests.

[0052] Suitable salts of the compounds of general formula (I) can be ordinary non-toxic salts, i.e. salts with appropriate bases and salts with added acids.Preferably, salts with inorganic bases, such as alkali metal salts, for example sodium, potassium or cesium salts, alkaline earth metal salts, for example calcium or magnesium salts, ammonium salts, salts with organic bases as well as with inorganic amines, for example triethylammonium, dicyclohexylammonium, N,N'-dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids, for example hydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates, or phosphates, salts with organic carboxylic acids or organic sulfonic acids, for example formates, acetates, trifluoroacetates, maleates, tartrates, methanesulfonates, benzenesulfonates or para-toluenesulfonates, salts with basic amino acids, for example arginates, aspartates or glutamates and the like, should be mentioned.

[0053] Isotopic variants

[0054] The present invention further includes all suitable isotopic variants of the compounds of formula (I). An isotopic variant of such a compound is to be understood as a compound of formula (I) in which at least one atom is replaced by another atom with the same atomic number but an atomic mass that differs from that which is commonly or predominantly found in nature. Examples of isotopes that can be incorporated into a compound of formula (I) are those of hydrogen, carbon, nitrogen, oxygen, phosphorus, sulfur, fluorine, chlorine, bromine, and iodine, such as 2 H (Deuterium), 3 H (Tritium), 13 C, 14 C, 15 N, 17 0, 18 0, 32 P, 33 P, 33 S, 34 S, 35 S, 36 S, 18 F, 36 C1, 82 Br, 123 1, 124 I, 129 I and 131I. Certain isotopic variants of a compound of formula (I), such as in particular those in which one or more radioactive isotopes are incorporated, can be useful, for example, for investigations of the mechanism of action or the distribution of the active substance, for example in the body of a pathogen; for this purpose, compounds with 3 H- or 14 C-isotope-labeled compounds are used because their production and detection are relatively simple. Furthermore, the incorporation of BYC240191 abroad

[0055] - 7 - Isotopes such as deuterium offer advantages, for example, due to greater metabolic stability of the compound, such as an extension of the half-life or a reduction of the required effective dose. Isotopic modifications of the compounds of formula (I) can therefore also represent a preferred embodiment of the invention. Isotopic variants of the compounds of formula (I) can be prepared according to methods known to those skilled in the art, for example, by the methods described below and the instructions given in the exemplary embodiments, using appropriate isotopic modifications of the respective reagents and / or starting compounds (reactants).

[0056] Methods and uses

[0057] The invention also relates to methods for controlling animal pests, in particular nematodes, in which compounds of formula (I) are applied to animal pests, in particular nematodes, and / or their habitat. The control of animal pests is preferably carried out in agriculture and forestry and in material protection. Methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods performed on the human or animal body are preferably excluded.

[0058] The invention further relates to the use of the compounds of formula (I) as pesticides, in particular plant protection products.

[0059] Within the scope of this application, the term pesticide always includes the term plant protection product.

[0060] The use of compounds of formula (I) according to the invention as pesticides also includes the case in which a compound of formula (I) is formed from a precursor substance (“prodrug”) only after application to the plant, in the plant or in the soil.

[0061] The compounds of formula (I) are suitable, with good plant compatibility, favorable warm-blooded toxicity and good environmental compatibility, for the protection of plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the harvested crop and for controlling animal pests, especially insects, arachnids, helminths, especially nematodes, and molluscs, which occur in agriculture, horticulture, animal breeding, aquaculture, forestry, gardens and recreational facilities, stored product and material protection and in the hygiene sector.

[0062] Within the scope of this patent application, the term "hygiene" is to be understood as encompassing any and all measures, regulations and procedures whose aim is to BYC240191 Abroad

[0063] - 8 - To prevent diseases, especially infectious diseases, and which serve to protect the health of humans and animals and / or the environment, and / or to maintain cleanliness. According to the invention, this includes in particular measures for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces, especially surfaces made of glass, wood, cement, porcelain, ceramic, plastic or also metal(s), to ensure that these are free from hygiene pests and / or their excretions. Preferably excluded from the scope of protection of the invention in this respect are surgical or therapeutic treatment procedures and diagnostic procedures applicable to the human body or the bodies of animals.

[0064] The term "hygiene sector" thus covers all areas, technical fields and industrial applications where these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, hospitals, stables, animal husbandry, etc.

[0065] The term "hygiene pest" should therefore be understood to mean one or more animal pests whose presence in the hygiene sector is problematic, particularly for health reasons. A primary objective is thus to prevent or minimize the presence of hygiene pests and / or exposure to them in the hygiene sector. This can be achieved, in particular, through the application of a pesticide that can be used both to prevent infestation and to control an existing infestation. Preparations that prevent or reduce exposure to pests can also be used. Hygiene pests include, for example, the organisms mentioned below.

[0066] The term "hygiene protection" therefore covers all actions by which these hygiene measures, regulations and procedures are maintained and / or improved.

[0067] The compounds of formula (I) can preferably be used as pesticides. They are effective against normally susceptible and resistant species, as well as against all or individual developmental stages. The pests mentioned above include:

[0068] Pests from the phylum Arthropoda, especially from the class Arachnida, e.g. Acarus spp., e.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., e.g. Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., e.g. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., e.g. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., e.g. Eutetranychus banksi, Eriophyes spp., e.g. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., e.g. Hemitarsonemus latus (=Polyphagotarsonemus latus), HyalommaBYC240191 Ausland

[0069] - 9 -spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., z. B. Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Omithodorus spp., Omithonyssus spp., Panonychus spp., z. B. Panonychus citri (=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., z. B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., e.g. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici;

[0070] aus der Klasse der Chilopoda z. B. Geophilus spp., Scutigera spp.;

[0071] from the order or class of Collembola, for example Onychiurus armatus; Sminthurus viridis;

[0072] aus der Klasse der Diplopoda z. B. Blaniulus dripped;

[0073] from the class of Insecta, e.g. from the order of Blattodea, e.g. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., e.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa;

[0074] from the order of Coleoptera e.g. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp., e.g. Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius, Agriotes spp., e.g. Agriotes linneatus, Agriotes mancus, Agriotes obscurus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anomala dubia, Anoplophora spp., e.g. Anoplophora glabripennis, Anthonomus spp., e.g. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Athous haemorrhoidales, Atomaria spp., e.g. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., e.g. B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., e.g. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., e.g. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., e.g.Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., e.g. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferruginous, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus fumissi, Dendroctonus spp., e.g. Dendroctonus ponderosae, 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., e.g. B. Epilachna borealis, Epilachna varivestis, Epitrix spp., e.g. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis,BYC240191 Ausland.

[0075] - 10 - Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus comutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hoplia argentea, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., e.g. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnostema consanguinea, Lasioderma serricome, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa ​​decemlineata, Leucoptera spp., e.g. Leucoptera coffeella, Limonius ectypus, Lissorhoptrus oryzophilus, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., e.g. B. Megacyllene robiniae, Megascelis spp., Melanotus spp., e.g. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., e.g. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., e.g. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., e.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., e.g. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., e.g. B. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferruginous, Rhynchophorus palmarum, Scolytus spp., z. B. Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp., z. B. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Stemechus spp., z. B.Stemechus paludatus, Symphyletes spp., Tanymecus spp., e.g. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., e.g. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., e.g. Zabrus tenebrioides;.

[0076] aus der Ordnung der Dermaptera z. B. Anisolabis maritime, Ficula auricularia, Labidura riparia;

[0077] 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 parvicomis, 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. B. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., z. B. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., z. B. Dasineura brassicae, Delia spp., z. B.Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., 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, LiriomyzaBYC240191 Ausland.

[0078] - 11 -huidobrensis, Liriomyza sativae, Lucilia spp., e.g. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musea spp., e.g. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterbomiella subcincta, Pegomya or Pegomyia spp., e.g. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., e.g. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., e.g. B. Southern Simulium, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., z. B. Onion paludosa, Onion simplex, Toxotrypana curvicauda;

[0079] aus der Ordnung der Hemiptera z. B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., z. B. Acyrthosiphon pea, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., z. B. Amrasca bigutulla, Amrasca devastating, Anuraphis cardui, Aonidiella spp., z. B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inomata, Aphanostigma piri, Aphis spp., z. B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis vibumiphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., z. B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., e.g. Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Cameocephala fiilgida, Ceratovacuna lanigera, Cercopidae, Ceropiastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halb, Coccus spp., e.g. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., e.g. B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., z. B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., z. B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolima spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., z. B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., z. B. Lecanium comi (=Parthenolecanium comi), Lepidosaphes spp., z. B. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., z. B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., z. B. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus omatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., z. B.Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra,BYC240191 Ausland.

[0080] - 12 - 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, Pianococcus spp., e.g. Pianococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., e.g. B. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus vibumi, Psyllopsis spp., Psylla spp., z. B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., z. B.Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastroccus spp., Rhopalosiphum spp., z. B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., z. B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., z. B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., z. B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;

[0081] 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 varicomis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., e.g. Lygocoris pabulinus, Lygus spp., e.g. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., z. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., z. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.;.

[0082] from the order of Hymenoptera e.g. Acromyrmex spp., Athalia spp., e.g. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., e.g. Diprion similis, Hoplocampa spp., e.g. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., e.g. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., e.g. Vespa crabro, Wasmannia auropunctata, Xeris spp.;

[0083] from the order of Isopoda, e.g. Armadillidium vulgare, Oniscus asellus, Porcellio scaber;BYC240191 Abroad

[0084] - 13 -from the order of Isoptera, e.g. Coptotermes spp., e.g. Coptotermes formosanus, Comitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermes spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., e.g. Reticulitermes flavipes, Reticulitermes hesperus;

[0085] 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. B. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., z. B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., z. B.Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., 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., e.g. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., e.g. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., e.g. Heliothis virescens, Hepialus spp., e.g. B. Hepialus humuli, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., z. B. Leucoptera coffeella, Lithocolletis spp., z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., z. B.Lobesia botrana, Loxagrotis albicosta, Lymantria spp., z. B. Lymantria dispar, Lyonetia spp., z. B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., z. B. Ostrinia nubilalis, Panolis flammea, Pamara spp., Pectinophora spp., z. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., z. B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., z. B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., z. B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutella maculipennis), Podesia spp., z. B. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., z. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., z.B. Schoenobius bipunctifer, Scirpophaga spp., e.g. Scirpophaga innotata, Scotia segetum, Sesamia spp., e.g. Sesamia inferens, Sparganothis spp., Spodopteraspp., 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, TineaBYC240191 Ausland.

[0086] - 14 -pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., z. B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.;

[0087] aus der Ordnung der Orthoptera oder Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., z. B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., z. B. Locust migratory, Melanoplus spp., z. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria;

[0088] aus der Ordnung der Phthiraptera z. B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.;

[0089] aus der Ordnung der Psocoptera z. B. Lepinotus spp., Liposcelis spp.;

[0090] from the order of Siphonaptera, e.g. Ceratophyllus spp., Ctenocephalides spp., e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

[0091] from the order of Thysanoptera, e.g. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., e.g. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., e.g. Thrips palmi, Thrips tabaci;

[0092] from the order of Zygentoma (= Thysanura), e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

[0093] aus der Klasse der Symphyla z. B. Scutigerella spp., z. B. Scutigerella Immaculata;

[0094] Schädlinge aus dem Stamm der Mollusca, z. B. aus der Klasse der Bivalvia, z. B. Dreissena spp.;

[0095] as well as from the class of 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.;

[0096] 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 omata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., e.g. B. Criconemoides femiae, Criconemoides onoense, Criconemoides omatum, Ditylenchus spp., e.g. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., e.g. Globodera pallida, Globodera rostochiensis,BYC240191 Foreign

[0097] - 15 - Helicotylenchus spp., e.g. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., e.g. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., e.g. Longidorus africanus, Meloidogyne spp., e.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., e.g. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., e.g. B. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., z. B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., z. B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., z. B. Tylenchorhynchus annulatus, Tylenchulus spp., z. B.Tylenchulus semipenetrans, Xiphinema spp., e.g. B. Xiphinema index.

[0098] Nematodes

[0099] In this context, the term "nematodes" encompasses all species of the phylum Nematoda, and in particular species that parasitize plants or fungi (for example, species of the orders Aphelenchida, Meloidogyne, Tylenchida and others) or also humans and animals (for example, species of the orders Trichinellida, Tylenchida, Rhabditina and Spirurida) and cause damage in or on these living beings, as well as other parasitic helminths.

[0100] A nematicide used in plant protection, as described here, has the ability to combat nematodes.

[0101] The term "nematode control" means killing the nematodes or preventing or hindering their development or growth, or preventing or hindering their penetration into or feeding on plant tissue.

[0102] The efficacy of the compounds is determined by comparing mortality, gall formation, cyst formation, nematode density per soil volume, nematode density per root, number of nematode eggs per soil volume, and nematode motility between a plant, plant part, or soil treated with the compound of formula (I) and an untreated plant, plant part, or soil (100%). Preferably, a reduction of 25–50% is achieved compared to an untreated plant, plant part, or soil; particularly preferably, a reduction of 51–79%; and most preferably, complete killing or complete prevention of nematode development and growth is achieved by a reduction of 80–100%. Nematode control, as described herein, also includes the control of nematode reproduction (development of cysts and / or eggs).Compounds of formula (I) can also be used to maintain the health of plants or animals and can be used curatively, preventively, or systemically for nematode control. BYC240191 Abroad.

[0103] - 16 - Methods are known to the person skilled in the art for determining mortality, gall formation, cyst formation, nematode density per soil volume, nematode density per root, number of nematode eggs per soil volume, and nematode mobility.

[0104] The use of a compound of formula (I) can keep the plant healthy and also includes a reduction in damage caused by nematodes as well as an increase in the amount of emte.

[0105] In this context, the term "nematodes" refers to plant nematodes, a group encompassing all nematodes that damage plants. Plant nematodes include plant-parasitic nematodes and soil-dwelling nematodes. Plant-parasitic nematodes include ectoparasites such as Xiphinema spp., Longidorus spp., and Trichodorus spp.; hemiparasites such as Tylenchulus spp.; migratory endoparasites such as Pratylenchus spp., Radopholus spp., and Scutellonema spp.; sessile parasites such as Heterodera spp., Globodera spp., and Meloidogyne spp.; and stem and leaf endoparasites such as Ditylenchus spp. and Aphelenchoides spp. and Hirschmaniella spp. Particularly harmful root-parasitic soil nematodes include, for example, cyst-forming nematodes of the genera Heterodera or Globodera, and / or root-knot nematodes of the genus Meloidogyne.Harmful species of these genera include, for example, Meloidogyne incognita, Heterodera glycines (soybean cyst nematode), Globodera pallida, and Globodera rostochiensis (yellow potato cyst nematode), and these species can be effectively controlled with the compounds described in this text. However, the use of the compounds described in this text is by no means limited to these genera or species, but extends equally to other nematodes.

[0106] Plant nematodes include, for example, B. Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Aphelenchoides fragaria and the stem and leaf endoparasites Aphelenchoides spp., Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus and Bursaphelenchus spp., Cacopaurus pestis, Criconemella curvata, Criconemella onoensis, Criconemella omata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax) and Criconemella spp., Criconemoides femiae, Criconemoides onoense, Criconemoides omatum and Criconemoides spp., Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus and the stem and leaf endoparasites Ditylenchus spp., Dolichodorus heterocephalus, Globodera pallida (=Heterodera pallida), Globodera rostochiensis (yellow potato cyst nematode), Globodera solanacearum, Globodera tabacum, Globodera virginia and the local cyst-forming parasites Globodera spp., Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus erythrine, Helicotylenchus multicinctus, Helicotylenchus nannus, Helicotylenchus pseudorobustus and Helicotylenchus spp., Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata, Hemicycliophora parvana, Heterodera avenae, Heterodera cruciferae, Heterodera glycines (Soybean cyst nematode), Heterodera oryzae, Heterodera schachtii, Heterodera zeae and the sessile cyst-forming parasites Heterodera spp., Hirschmaniella gracilis, BYC240191 Abroad.

[0107] - 17 - Hirschmaniella oryzae, Hirschmaniella spinicaudata and the stem and leaf endoparasites Hirschmaniella spp., Hoplolaimus aegyptii, Hoplolaimus califomicus, Hoplolaimus columbus, Hoplolaimus galeatus, Hoplolaimus indicus, Hoplolaimus magnistylus, Hoplolaimus pararobustus, Longidorus africanus, Longidorus breviannulatus, Longidorus elongatus, Longidorus laevicapitatus, Longidorus vineacola and the ectoparasites Longidorus spp., Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne artiella, Meloidogyne chitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, Meloidogyne exigua, Meloidogyne fallax, Meloidogyne graminicola, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis, Meloidogyne minor, Meloidogyne naasi, Meloidogyne paranaensis, Meloidogyne thamesi und die ortsgebundenen Parasiten Meloidogyne spp., Meloinema spp., Nacobbus aberrans, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Paratrichodorus allius, Paratrichodorus lobatus, Paratrichodorus minor, Paratrichodorus nanus, Paratrichodorus porosus, Paratrichodorus teres and Paratrichodorus spp., Paratylenchus hamatus, Paratylenchus minutus, Paratylenchus projectus and Paratylenchus spp., Pratylenchus agilis, Pratylenchus allem, Pratylenchus andinus, Pratylenchus brachyurus, Pratylenchus cerealis, Pratylenchus coffeae, Pratylenchus crenatus, Pratylenchus delattrei, Pratylenchus giibbicaudatus, Pratylenchus goodeyi, Pratylenchus hamatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus teres, Pratylenchus thomei, Pratylenchus vulnus, Pratylenchus zeae und die migratorischen Endoparasiten Pratylenchus spp., Pseudohalenchus minutus, Psilenchus magnidens, Psilenchus tumidus, Punctodera chalcoensis, Quinisulcius acutus, Radopholus citrophilus, Radopholus similis, the migratory endoparasites Radopholus spp., Rotylenchulus borealis, Rotylenchulus parvus, Rotylenchulus reniformis and Rotylenchulus spp., Rotylenchus laurentinus, Rotylenchus macrodoratus, Rotylenchus robustus, Rotylenchus uniformis and Rotylenchus spp., Scutellonema brachyurum, Scutellonema bradys, Scutellonema clathricaudatum and the migratory endoparasites Scutellonema spp., Subanguina radiciola, Tetylenchus nicotianae, Trichodorus cylindricus, Trichodorus minor, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus and the ectoparasites Trichodorus spp., Tylenchorhynchus agri, Tylenchorhynchus brassicae, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris and Tylenchorhynchus spp., Tylenchulus semipenetrans and the semiparasites Tylenchulus spp., Xiphinema americanum, Xiphinema brevicolle, Xiphinema dimorphicaudatum, Xiphinema index and the ectoparasites Xiphinema spp.

[0108] Among the nematodes that can be controlled with a compound of formula (I) are nematodes of the genus Meloidogyne such as the Southern Root-Knot Nematode (Meloidogyne incognita), the Javanese Root-Knot Nematode (Meloidogyne javanica), the Northern Root-Knot Nematode (Meloidogyne hapla), and the Peanut Root-Knot Nematode (Meloidogyne arenaria); nematodes of the genus Ditylenchus such as the Potato Scab Nematode (Ditylenchus destructor) and the Stem Nematode (Ditylenchus dipsaci); nematodes of the genus Pratylenchus such as the Cob Root Lesion BYC240191 Abroad

[0109] - 18 - Nematode (Pratylenchus penetrans), the Chrysanthemum Root Lesion Nematode (Pratylenchus fallax), the Coffee Root Nematode (Pratylenchus coffeae), the Tea Root Nematode (Pratylenchus loosi) and the Walnut Root Lesion Nematode (Pratylenchus vulnus); nematodes of the genus Globodera such as the Yellow Potato Cyst Nematode (Globodera rostochiensis) and the White Potato Cyst Nematode (Globodera pallida); nematodes of the genus Heterodera such as the Soybean Cyst Nematode (Heterodera glycines) and the Beet Cyst Nematode (Heterodera schachtii); Nematodes of the genus Aphelenchoides such as the Rice White-tip Nematode (Aphelenchoides besseyi), the Chrysanthemum Nematode (Aphelenchoides ritzemabosi) and the Strawberry Nematode (Aphelenchoides fragariae); nematodes of the genus Aphelenchus such as the fungivorous nematode (Aphelenchus avenae); nematodes of the genus Radopholus, such as the Burrowing Nematode (Radopholus similis);Nematodes of the genus Tylenchulus, such as the orange root nematode (Tylenchulus semipenetrans); nematodes of the genus Rotylenchulus, such as the reniform nematode (Rotylenchulus reniformis); tree-dwelling nematodes, such as the pine wood nematode (Bursaphelenchus xylophilus) and the red ring nematode (Bursaphelenchus cocophilus), and the like.

[0110] Plants for whose protection a compound of formula (I) can be used include plants such as cereals (for example, rice, barley, wheat, rye, oats, maize, and the like), beans (soybean, adzuki bean, bean, broad bean, peas, peanuts, and the like), fruit trees / fruits (apples, citrus fruits, pears, grapes, peaches, Japanese apricots, cherries, walnuts, almonds, bananas, strawberries, and the like), vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, leek, peppers, and the like), root crops (carrot, potato, sweet potato, radish, lotus root, swede, and the like), plants for industrial raw materials (cotton, hemp, paper mulberry, mitsumata, rapeseed, beet, hops, sugar cane, sugar beet, olive, rubber, palms, coffee, tobacco, tea, and the like), cucurbits (pumpkin, Cucumber, watermelon, melon and the like), pasture plants (orchard grass, sorghum, timothy grass, clover, alfalfa and the like), lawn grasses (Mascarene grass,Creeping bentgrass and the like), herbs, etc. (lavender, rosemary, thyme, parsley, pepper, ginger and the like) and flowers (chrysanthemum, rose, orchid and the like).

[0111] The compounds of formula (I) are particularly suitable for controlling coffee nematodes, especially Pratylenchus brachyurus, Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne incognita, Meloidogyne coffeicola, Helicotylenchus spp., as well as Meloidogyne paranaensis, Rotylenchus spp., Xiphinema spp., Tylenchorhynchus spp., and Scutellonema spp.

[0112] The compounds of formula (I) are particularly suitable for controlling potato nematodes, especially Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus penetrans, Pratylenchus coffeae, Ditylenchus dipsaci, as well as Pratylenchus allem, Pratylenchus andinus, Pratylenchus cerealis, Pratylenchus crenatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus teres, Pratylenchus thomei, Pratylenchus vulnus, BYC240191 Abroad

[0113] - 19 - Belonolaimus longicaudatus, Trichodorus cylindricus, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus, Paratrichodorus minor, Paratrichodorus allius, Paratrichodorus nanus, Paratrichodorus teres, Meloidogyne arenaria, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne thamesi, Meloidogyne incognita, Meloidogyne chitwoodi, Meloidogyne javanica, Nacobbus aberrans, Globodera rostochiensis, Globodera pallida, Ditylenchus destructor, Radopholus similis, Rotylenchulus reniformis, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Aphelenchoides fragariae and Meloinema spp.

[0114] The compounds of formula (I) are particularly suitable for controlling nematodes of the tomato, especially Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Pratylenchus penetrans and also Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus vulnus, Paratrichodorus minor, Meloidogyne exigua, Nacobbus aberrans, Globodera solanacearum, Dolichodorus heterocephalus and Rotylenchulus reniformis.

[0115] The compounds of formula (I) are particularly suitable for the control of nematodes of cucurbit plants, especially Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Rotylenchulus reniformis and Pratylenchus thomei.

[0116] The compounds of formula (I) are particularly suitable for controlling cotton nematodes, especially Belonolaimus longicaudatus, Meloidogyne incognita, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus reniformis.

[0117] The compounds of formula (I) are particularly suitable for controlling nematodes of maize, in particular Belonolaimus longicaudatus, Paratrichodorus minor and also Pratylenchus brachyurus, Pratylenchus delattrei, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus zeae, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorus breviannulatus, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne graminis, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne naasi, Heterodera avenae, Heterodera oryzae, Heterodera zeae, Punctodera chalcoensis, Ditylenchus dipsaci, Hoplolaimus aegyptii, Hoplolaimus magnistylus, Hoplolaimus galeatus, Hoplolaimus indicus, Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus pseudorobustus, Xiphinema americanum, Dolichodorus heterocephalus, Criconemella omata, Criconemella onoensis, Radopholus similis, Rotylenchulus borealis, Rotylenchulus parvus, Tylenchorhynchus agri,Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris, Quinisulcius acutus, Paratylenchus minutus, Hemicycliophora parvana, Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Scutellonema brachyurum and Subanguina radiciola.,

[0118] Die Verbindung der Formel (I) eigenen sich besonders für die Bekämpfung von Nematoden der Sojabohne, in particular von Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus penetrans, Pratylenchus scribneri, Belonolaimus longicaudatus, Heterodera glycines, Hoplolaimus columbus undBYC240191 Ausland

[0119] - 20 -also Pratylenchus coffeae, Pratylenchus hexincisus, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus allem, Pratylenchus agilis, Pratylenchus zeae, Pratylenchus vulnus, (Belonolaimus gracilis), Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus reniformis.

[0120] The compounds of formula (I) are particularly suitable for controlling tobacco nematodes, especially Meloidogyne incognita, Meloidogyne javanica, and also Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus thomei, Pratylenchus vulnus, Pratylenchus zeae, Longidorus elongatu, Paratrichodorus lobatus, Trichodorus spp., Meloidogyne arenaria, Meloidogyne hapla, Globodera tabacum, Globodera solanacearum, Globodera virginiae, Ditylenchus dipsaci, Rotylenchus spp., Helicotylenchus spp., Xiphinema americanum, Criconemella spp., Rotylenchulus reniformis, Tylenchorhynchus claytoni, Paratylenchus spp. And Tetylenchus nicotianae.

[0121] The compounds of formula (I) are particularly suitable for controlling nematodes of citrus plants, especially of Pratylenchus coffeae and also Pratylenchus brachyurus, Pratylenchus vulnus, Belonolaimus longicaudatus, Paratrichodorus minor, Paratrichodorus porosus, Trichodorus, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Rotylenchus macrodoratus, Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Criconemella spp., Hemicriconemoides, Radopholus similis and Radopholus citrophilus, Hemicycliophora arenaria, Hemicycliophora nudata and Tylenchulus semipenetrans.

[0122] The compounds of formula (I) are particularly suitable for controlling banana nematodes, especially Pratylenchus coffeae, Radopholus similis and also Pratylenchus giibbicaudatus, Pratylenchus loosi, Meloidogyne spp., Helicotylenchus multicinctus, Helicotylenchus dihystera and Rotylenchulus spp.

[0123] The compounds of formula (I) are particularly suitable for controlling pineapple nematodes, in particular Pratylenchus zeae, Pratylenchus pratensis, Pratylenchus brachyurus, Pratylenchus goodeyi., Meloidogyne spp., Rotylenchulus reniformis and also Longidorus elongatus, Longidorus laevicapitatus, Trichodorus primitivus, Trichodorus minor, Heterodera spp., Ditylenchus myceliophagus, Hoplolaimus califomicus, Hoplolaimus pararobustus, Hoplolaimus indicus, Helicotylenchus dihystera, Helicotylenchus nannus, Helicotylenchus multicinctus, Helicotylenchus erythrine, Xiphinema dimorphicaudatum, Radopholus similis, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Paratylenchus minutus, Scutellonema clathricaudatum, Scutellonema bradys, Psilenchus tumidus, Psilenchus magnidens, Pseudohalenchus minutus, Criconemoides femiae, Criconemoides onoense and Criconemoides omatum.

[0124] The compounds of formula (I) are particularly suitable for controlling nematodes of grapes, especially of Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne incognita, MeloidogyneBYC240191 Abroad

[0125] - 21 -javanica, Xiphinema americanum, Xiphinema index and also Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus, Pratylenchus brachyurus, Pratylenchus thomei and Tylenchulus semipenetrans.

[0126] The compounds of formula (I) are particularly suitable for the control of nematodes of tree crops - pome fruit, especially Pratylenchus penetrans and also Pratylenchus vulnus, Longidorus elongatus, Meloidogyne incognita and Meloidogyne hapla.

[0127] The compounds of formula (I) are particularly suitable for the control of nematodes of tree crops - stone fruits, especially Pratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Criconemella xenoplax and Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus zeae, Belonolaimus longicaudatus, Helicotylenchus dihystera, Xiphinema americanum, Criconemella curvata, Tylenchorhynchus claytoni, Paratylenchus hamatus, Paratylenchus projectus, Scute llonema brachyurum and Hoplolaimus galeatus.

[0128] The compounds of formula (I) are particularly suitable for controlling nematodes in tree crops, sugar cane and rice, especially Trichodorus spp., Criconemella spp., Pratylenchus spp., Paratrichodorus spp., Meloidogyne spp., Helicotylenchus spp., Tylenchorhynchus spp., Aphelenchoides spp., Heterodera spp., Xiphinema spp. and Cacopaurus pestis.

[0129] The compounds of formula (I) can, if necessary, also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents to improve plant characteristics, as microbicides or gametocides, for example as fungicides, antifungals, bactericides, viricides (including agents against viroids) or as agents against MUO (Mycoplasma-like organisms) and RLO (Rickettsia-like organisms). They can also be used, if necessary, as intermediates or precursors for the synthesis of further active ingredients.

[0130] Formulations / Application methods

[0131] The present invention further relates to formulations, in particular formulations for controlling unwanted animal pests, especially nematodes. The formulation can be applied to the animal pest and / or in its habitat.

[0132] The formulation according to the invention can be provided to the end user as a ready-to-use “application form”, i.e., the formulations can be applied directly to the plants or seeds using a suitable device such as a sprayer or duster. Alternatively, the formulations can be provided to the end user in the form of concentrates that are preferably to be diluted with water before application. Unless otherwise specified, the term “formulation” thus refers to such a concentrate, while the term “application form” refers to a BYC240191 foreign

[0133] - 22 - refers to a ready-to-use solution for the end user, i.e., usually such a diluted formulation.

[0134] The formulation according to the invention can be produced in a conventional manner, for example by mixing the compound according to the invention with one or more suitable excipients such as, for example, those disclosed herein.

[0135] The formulation comprises at least one compound according to the invention and at least one agriculturally useful auxiliary material, e.g. carrier and / or surfactant(s).

[0136] A carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert. The carrier generally improves the release of compounds, for example, onto plants, plant parts, or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, especially ammonium sulfates, ammonium phosphates, and ammonium nitrates; ground natural rocks such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth; silica gel; and ground synthetic rocks such as finely divided silicon dioxide, aluminum oxide, and silicates. Examples of typical suitable solid carriers for the production of granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, and dolomite; synthetic granules of inorganic and organic flours; and granules of organic materials such as paper.Examples include sawdust, coconut shells, corncobs, and tobacco stalks. Suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include polar and nonpolar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may also be substituted, etherified and / or esterified, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines,Amides (such as dimethylformamide or fatty acid amides) and esters thereof, lactams (such as N-alkylpyrrolidones, especially N-methylpyrrolidone) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide), nitriles (alkyl nitriles such as acetonitrile, propionitrile, butyronitrile, or aromatic nitriles such as benzonitrile), carbonic acid esters (cyclic carbonic acid esters such as ethylene carbonate, propylene carbonate, butylene carbonate, or dialkyl carboxylic acid esters such as dimethyl carbonate, diethyl carbonate, dipropyl carbonate, dibutyl carbonate, dioctyl carbonate). The carrier may also be a naturally occurring mixture of representatives of the aforementioned solvents, such as mineral oils, vegetable oils, or animal oils. The carrier may also be a liquefied gaseous extender, i.e., a liquid that, under normal conditions,

[0137] - 23 - temperature and is gaseous under normal pressure, for example aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.

[0138] Preferred solid supports are selected from clays, talc and silicon dioxide.

[0139] Preferred liquid carriers are selected from water, fatty acid amides and esters thereof, aromatic and non-aromatic hydrocarbons, lactams, lactones, carbonic acid esters, ketones, (poly)etheme.

[0140] The amount of carrier typically ranges from 1 to 99.99 wt.%, preferably 5 to 99.9 wt.%, particularly preferably 10 to 99.5 wt.% and most preferably 20 to 99 wt.% of the formulation.

[0141] Liquid carriers are typically present in a range of 20 to 90 wt.%, for example 30 to 80 wt.% of the formulation.

[0142] Solid carriers are typically present in a range of 0 to 50 wt.%, preferably 5 to 45 wt.%, for example 10 to 30 wt.% of the formulation.

[0143] If the formulation includes two or more carriers, the outlined areas refer to the total number of carriers.

[0144] The surfactant can be an ionic (cationic or anionic), amphoteric or non-ionic surfactant such as ionic or non-ionic emulsifiers, foaming agents, dispersants, wetting agents, penetration enhancers and any mixtures thereof. Examples of suitable surfactants include, but are not limited to, salts of polyacrylic acid, ethoxylated poly(alpha-substituted)acrylate derivatives, salts of lignosulfonic acid (such as sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and / or propylene oxide with or without alcohols, fatty acids or fatty amines (for example, polyoxyethylene fatty acid esters such as castor oil ethoxylate, polyoxyethylene fatty alcohol ethers, for example, alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfobem succinic acid esters, taurine derivatives (preferably alkyltaurates), and phosphoric acid esters of polyethoxylated alcohols or phenols.Fatty acid esters of polyols (such as fatty acid esters of glycerol, sorbitol, or sucrose), sulfates (such as alkyl sulfates and alkyl ether sulfates), sulfonates (for example, alkyl sulfonates, aryl sulfonates, and alkylbenzene sulfonates), sulfonated polymers of naphthalene / formaldehyde, phosphate esters, protein hydrolysates, lignosulfite liquors, and methylcellulose are included. Where reference is made to salts in this paragraph, this preferably refers to the relevant alkali, alkaline earth, and ammonium salts.

[0145] Preferred surfactants are ethoxylated poly(alpha-substituted)acrylate derivatives, polycondensates of ethylene oxide and / or propylene oxide with alcohols, polyoxyethylene fatty acid esters, alkylbenzenesulfonates, sulfonated polymers of naphthalene / formaldehyde, BYC240191 Abroad

[0146] - 24 - Polyoxyethylene fatty acid systems such as castor oil ethoxylate, sodium lignosulfonate and arylphenol ethoxylate were selected.

[0147] The amount of surfactant is typically in the range of 5 to 40 wt%, for example 10 to 20 wt%, of the formulation.

[0148] Other examples of suitable additives include water-repellent substances, desiccants, binders (adhesives, bonding agents, fixatives such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latizes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone and Tylose), thickeners and secondary thickeners (such as cellulose ethers, acrylic acid derivatives, xanthan gum, modified clays, e.g. the products available under the name Bentone, and finely divided silicon dioxide), stabilizers (e.g. cold stabilizers, preservatives (e.g.Dichlorophon, benzyl alcohol hemiformal, 1,2-benzisothiazolin-3-one, 2-methyl-4-isothiazolin-3-one), antioxidants, light stabilizers, especially UV stabilizers, and other agents that improve chemical and / or physical stability), dyes or pigments (such as inorganic pigments, e.g., iron oxide, titanium dioxide, and Prussian blue; organic dyes, e.g., alizarin, azo, and metal phthalocyanine dyes), antifoaming agents (e.g., silicone antifoaming agents and magnesium stearate), antifreeze, adhesives, gibberellins, and processing aids, mineral and vegetable oils, perfumes, waxes, nutrients (including trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc), protective colloids, thixotropic substances, penetrating agents, sequestrants, and complexing agents.

[0149] The selection of excipients depends on the intended application of the compound according to the invention and / or on the physical properties of the compound(s). Furthermore, excipients can be selected to impart specific properties (technical, physical, and / or biological properties) to the formulations or the resulting application forms. The selection of excipients may make it possible to tailor the formulations to specific needs.

[0150] The formulation comprises an insecticidal / acaricidal / nematicidal effective amount of the compound(s) according to the invention. The term "effective amount" refers to an amount sufficient to control pest insects / mites / nematodes on cultivated plants or for material protection, and which does not substantially damage the treated plants. Such an amount can vary over a wide range and depends on various factors such as the insect / mite / nematode species to be controlled, the cultivated plant or material being treated, the climatic conditions, and the specific compound according to the invention used. The formulation according to the invention typically contains 0.01 to 99 wt.%, preferably 0.05 to 98 wt.%, particularly preferably 0.1 to 95 wt.%, even more preferably 0.5 to 90 wt.%, and most preferably 1 to 95 wt.%.

[0151] - 25–80 wt.% of the compound according to the invention. It is possible that a formulation comprises two or more compounds according to the invention. In such a case, the outlined ranges refer to the total quantity of the compounds of the present invention.

[0152] The formulation according to the invention can be in any conventional formulation type, such as solutions (e.g., aqueous solutions), emulsions, water- and oil-based suspensions, powders (e.g., spray powders, soluble powders), dusts, pastes, granules (e.g., soluble granules, granules for spreading), suspoemulsion concentrates, natural or synthetic products impregnated with the compound according to the invention, fertilizers, and also microencapsulations in polymeric substances. The compound according to the invention can be in suspended, emulsified, or dissolved form. Examples of certain suitable formulation types include solutions, water-soluble concentrates (e.g., SL, LS), dispersion concentrates (DC), suspensions and suspension concentrates (e.g., SC, OD, OF, FS), emulsion concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME, SE), capsules (e.g., CS, ZC), pastes, lozenges, spray powders or dusts (e.g., WP, SP, WS, DP, DS), and pressed parts (e.g.,BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticidal articles (e.g., LN), and gel formulations for treating plant reproductive material such as seeds (e.g., GW, GF). These and other formulation types are defined by the Food and Agriculture Organization of the United Nations (FAO). An overview can be found in the "Catalogue of pesticide formulation types and international coding system," Technical Monograph No. 2, 6th ed., May 2008, Croplife International.

[0153] Preferably, the formulation according to the invention is in the form of one of the following types: EC, SC, FS, SE, OD, WG, WP, CS, particularly preferably EC, SC, OD, WG, CS.

[0154] Further details on examples of formulation types and their preparation can be found below. If two or more compounds according to the invention are present, the specified quantity of compound according to the invention refers to the total quantity of compounds of the present invention. Conversely, this also applies to all other components of the formulation if two or more representatives of such a component, e.g., a wetting agent or binder, are present.

[0155] i) Water-soluble concentrates (SL, LS)

[0156] 10-60 wt% of at least one compound according to the invention and 5-15 wt% surfactant (e.g., polycondensates of ethylene oxide and / or propylene oxide with alcohols) are dissolved in such a quantity of water and / or water-soluble solvent (e.g., alcohols such as propylene glycol and carbonates such as propylene carbonate) that a total quantity of 100 wt% is obtained. The concentrate is diluted with water before use.

[0157] ii) Dispersion concentrates (DC)

[0158] 5-25 wt.% of at least one compound according to the invention and 1-10 wt.% surfactant and / or binder (e.g. polyvinylpyrrolidone) are dissolved in such an amount of organic solvent (e.g. BYC240191 Abroad)

[0159] - 26 - cyclohexane) dissolved, resulting in a total amount of 100 wt%. Dilution with water yields a dispersion.

[0160] iii) Emulsion concentrates (EC)

[0161] 15-70 wt% of at least one compound according to the invention and 5-10 wt% surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in such an amount of water-insoluble organic solvent (e.g., aromatic hydrocarbon or fatty acid amide) and, if necessary, additional water-soluble solvent, as to achieve a total amount of 100 wt%. Dilution with water yields an emulsion. iv) Emulsions (EW, EO, ES)

[0162] 5-40 wt% of at least one compound according to the invention and 1-10 wt% surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, or polycondensates of ethylene oxide and / or propylene oxide with or without alcohols) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g., aromatic hydrocarbon). The mixture is added to water using an emulsifying machine in such a way as to obtain a total of 100 wt%. The resulting formulation is a homogeneous emulsion. Before use, the emulsion can be further diluted with water. v) Suspensions and Suspension Concentrates

[0163] v-1) Water-based (SC, FS)

[0164] In a suitable milling device, e.g., a ball mill, 20–60 wt% of at least one compound according to the invention are ground to a fine active ingredient suspension with the addition of 2–10 wt% surfactant (e.g., sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1–2 wt% thickener (e.g., xanthan gum), and water. Water is added in such a quantity as to obtain a total of 100 wt%. Dilution with water yields a stable suspension of the active ingredient. For FS-type formulations, up to 40 wt% binder (e.g., polyvinyl alcohol) is added.

[0165] v-2) Oil-based (OD, OF)

[0166] In a suitable grinding device, e.g., a ball mill, 20–60 wt.% of at least one compound according to the invention are ground to a fine active ingredient-oil suspension with the addition of 2–10 wt.% surfactant (e.g., sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1–2 wt.% thickening agent (e.g., modified clay, in particular bentone, or silicon dioxide), and an organic carrier. The organic carrier is added in such a quantity as to obtain a total quantity of 100 wt.%. Dilution with water yields a stable dispersion of the active ingredient. vi) Water-dispersible granules and water-soluble granules (WG, SG) BYC240191 Abroad

[0167] - 27 - 1-90 wt.%, preferably 20-80 wt.%, most preferably 50-80 wt.% of at least one compound according to the invention are finely ground with the addition of a surfactant (e.g., sodium lignosulfonate and sodium alkylnaphthylsulfonates) and optionally a carrier material and converted into water-dispersible or water-soluble granules by means of typical technical applications such as extrusion, spray drying, fluid bed granulation. The surfactant and carrier material are used in such quantities as to obtain a total quantity of 100 wt.%. Dilution with water yields a stable dispersion or solution of the active ingredient.

[0168] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0169] 50-80 wt% of at least one compound according to the invention are milled in a rotor-stator mill with the addition of 1-20 wt% surfactant (e.g., sodium lignosulfonate, sodium alkylnaphthylsulfonates) and an amount of solid support, e.g., silica gel, such that a total amount of 100 wt% is achieved. Dilution with water yields a stable dispersion or solution of the active ingredient.

[0170] viii) Gel (GW, GP)

[0171] In a suitable grinding device, e.g., a ball mill, 5-25 wt.% of at least one compound according to the invention are ground with the addition of 3-10 wt.% surfactant (e.g., sodium lignosulfonate), 1-5 wt.% binder (e.g., carboxymethylcellulose), and enough water to reach a total of 100 wt.%. This yields a fine suspension of the active ingredient. Dilution with water produces a stable suspension of the active ingredient.

[0172] ix) Microemulsion (ME)

[0173] 5-20 wt% of at least one compound according to the invention are added to 5-30 wt% of an organic solvent mixture (e.g., fatty acid dimethylamide and cyclohexanone), 10-25 wt% of a surfactant mixture (e.g., polyoxyethylene fatty alcohol ether and arylphenol ethoxylate), and an amount of water sufficient to achieve a total of 100 wt%. This mixture is stirred for 1 h, during which a thermodynamically stable microemulsion spontaneously forms.

[0174] x) Microcapsules (CS)

[0175] An oil phase containing 5-50 wt% at least one compound according to the invention, 0-40 wt% water-insoluble organic solvent (e.g., aromatic hydrocarbon), and 2-15 wt% acrylic monomers (e.g., methyl methacrylate, methacrylic acid, and a di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Radical polymerization initiated with a radical initiator leads to the formation of poly(methyl)acrylate microcapsules. Alternatively, a 5-50 wt% at least one compound according to the invention, 0-40 wt% water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethene 4,4'-diisocyanate) are dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). BYC240191 Abroad

[0176] - 28 -The oil phase, comprising 28 parts, is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol), leading to the formation of polyhammer microcapsules. Optionally, the addition of a polyamine (e.g., hexamethylenediamine) can also be used to induce the formation of polyhammer microcapsules. The monomers constitute 1-10 wt% of the total CS formulation.

[0177] xi) Dust powders (DP, DS)

[0178] 1-10 wt.% of at least one compound according to the invention are finely ground and intimately mixed with such an amount of solid carrier, e.g. finely divided kaolin, that a total amount of 100 wt.% is achieved.

[0179] xii) Granules (GR, FG)

[0180] 0.5-30 wt.% of at least one compound according to the invention are finely ground and associated with such an amount of solid support (e.g. silicate) that a total amount of 100 wt.% is achieved.

[0181] xiii) Ultra-low volume liquids (UL)

[0182] 1-50 wt.% of at least one compound according to the invention are dissolved in such an amount of organic solvent, e.g. aromatic hydrocarbon, that a total amount of 100 wt.% is achieved.

[0183] Formulation types i) to xiii) may include further excipients such as 0.1-1 wt.% preservatives, 0.1-1 wt.% antifoaming agents, 0.1-1 wt.% colorants and / or pigments and 5-10 wt.% antifreeze.

[0184] Mixtures

[0185] The compounds of formula (I) can also be used in mixtures with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiological agents, beneficial organisms, herbicides, fertilizers, bird repellents, phytotonics, sterilizing agents, safeners, resistance inducers, semiochemicals, and / or plant growth regulators to, for example, broaden the spectrum of activity, prolong the duration of action, increase the speed of action, prevent repellency, or prevent the development of resistance. Furthermore, such combinations of active ingredients can improve plant growth and / or tolerance to abiotic factors such as high or low temperatures, drought, or increased water or soil salinity.It is also possible to improve flowering and fruiting behavior, optimize germination and root development, facilitate harvesting and increase yield, influence ripening, increase the quality and / or nutritional value of the harvested products, extend storage life and / or improve the processing of the harvested products. BYC240191 Abroad.

[0186] - 29 - Furthermore, the compounds of formula (I) may be present in mixtures with other active ingredients or semiochemicals, such as attractants and / or bird repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of formula (I) may be used to improve plant characteristics such as growth, yield, and the quality of the harvested crop.

[0187] In a particular embodiment according to the invention, the compounds of formula (I) are present in formulations or in application forms prepared from these formulations in mixture with other compounds, preferably such as those described below.

[0188] If any of the compounds mentioned below can exist in different tautomeric forms, these forms are also included, even if they are not explicitly named in every case. Furthermore, all the mixture components mentioned can, if their functional groups allow, form salts with suitable bases or acids.

[0189] Insecticides / Acaricides / Nematicides

[0190] The active ingredients listed here by their "common name" are well-known and described, for example, in the Pesticide Manual ("The Pesticide Manual," 16th ed., British Crop Protection Council 2012) or can be found online (e.g., http: / / www.alanwood.net / pesticides). The classification is based on the IRAC Mode of Action Classification Scheme valid at the time of filing this patent application.

[0191] (1) Acetylcholinesterase (AChE) inhibitors, preferably carbamates selected from alanycarb, aldicarb, bendiocarb, benfiiracarb, butocarboxime, butoxycarboxime, carbaryl, carbofiiran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb, or organophosphates selected from acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, 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) salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion-methyl,Phenthoate, Phorate, Phosalon, Phosmet, Phosphamidone, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon and Vamidothion.

[0192] (2) GAB A-ge controlled chloride channel blockers, preferably cyclodiene organochlorines selected from chlordane and endosulfan, or phenylpyrazoles (fiproles) selected from ethiprol and fipronil. BYC240191 Abroad

[0193] - 30 - (3) Natrium-Kanal-Modulatoren, vorzugsweise Pyrethroide ausgewählt aus 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 [(lR)-trans-Isomer], Deltamethrin, Empenthrin [(EZ)-(lR)-Isomer], Esfenvalerat, Etofenprox, Fenpropathrin, Fenvalerat, Flucythrinat, Flumethrin, tau-Fluvalinat, Halfenprox, Imiprothrin, Kadethrin, Momfluorothrin, Permethrin, Phenothrin [(lR)-trans-Isomer], Prallethrin, Pyrethrine (Pyrethrum), Renofluthrin, Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R) -Isomer], Tralomethrin und Transfluthrin, oder DDT oder Methoxychlor.

[0194] (4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), preferably neonicotinoids selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoximines selected from sulfoxaflor, or butenolides selected from flupyradifurone, or mesoionics selected from dicloromezotiaz and triflumezopyrim, or pyridylidenes selected from flupyrimine.

[0195] (5) Allosteric modulators of the nicotinic acetylcholine receptor (nAChR, binding site I), preferably spinosynes selected from spinetoram and spinosad.

[0196] (6) Allosteric modulators of the glutamate-dependent chloride channel (GluCl), preferably avermectins / milbemycins selected from abamectin, emamectin benzoate, lepimectin and milbemectin.

[0197] (7) Juvenile hormone mimetics, preferably juvenile hormone analogues selected from hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.

[0198] (8) Various non-specific (multi-site) inhibitors, preferably alkyl halides selected from methyl bromide and other alkyl halides, or chloropicrin or sulfiriyl fluoride or borax or tartar emetic or methyl isocyanate generators selected from diazomet and metam.

[0199] (9) TRPV channel modulators of chordotonal organs, preferably pyridinazomethanes selected from pymetrozine and pyrifluquinazone or pyropenes selected from afidopyropene.

[0200] (10) CHS1 mite growth inhibitors selected from clofentezine, hexythiazox, diflovidazine and etoxazole.

[0201] (11) Microbial disruptors of the insect intestinal membrane selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kursiaki, Bacillus thuringiensis subspecies tenehrionis and B i -BYC240191 Abroad

[0202] - 31 - Plant proteins selected from CrylAb, CrylAc, CrylFa, Cry 1A.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Abl / 35Abl.

[0203] (12) Inhibitors of mitochondrial ATP synthase, preferably ATP disruptors selected from diafenthiuron, or organotin compounds selected from azocyclotin, cyhexatin and fenbutatin oxide, or propargite or tetradifone.

[0204] (13) Uncouplers of oxidative phosphorylation by disturbance of the proton gradient selected from chlorfenapyr, DNOC and sulfuramide.

[0205] (14) Blockers of the nicotinic acetylcholine receptor channel selected from Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.

[0206] (15) CHS1 inhibitors of chitin biosynthesis, preferably benzoyl inhibitors selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexafluuron, lufenuron, novaluron, novifluuron, teflubenzuron and triflumurone.

[0207] (16) Inhibitors of chitin biosynthesis, type 1 selected from buprofezin.

[0208] (17) Molting disruptors (especially in Diptera, i.e., true flies) selected from cyromazine.

[0209] (18) Ecdysone receptor agonists, preferably diacylhydrazines selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0210] (19) Octopamine receptor agonists selected from amitraz.

[0211] (20) Mitochondrial complex III electron transport inhibitors selected from hydramethylnone, acequinocyl, fluacrypyrim and bifenazate.

[0212] (21) Mitochondrial complex I electron transport inhibitors, preferably METI acaricides and insecticides selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).

[0213] (22) Voltage-gated sodium channel blockers, preferably oxadiazines selected from indoxacarb or semicarbazones selected from metaflumizone.

[0214] (23) Inhibitors of acetyl-CoA carboxylase, preferably tetronic and tetramic acid derivatives selected from spirodiclofen, spiromesifen, spiropide ion and spirotetramate.

[0215] (24) Inhibitors of mitochondrial complex IV electron transport, preferably phosphides selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides selected from calcium cyanide, potassium cyanide and sodium cyanide. BYC240191 Abroad

[0216] - 32 - (25) Inhibitors of mitochondrial complex II electron transport, preferably beta-ketonitrile derivatives selected from cyenopyrafen and cyflumetofen, or carboxanilides selected from pyflubumide.

[0217] (28) Ryanodine receptor modulators, preferably diamides selected from chloroantraniliproles, cyantraniliproles, cyclaniliproles, flubendiamides and tetraniliproles.

[0218] (29) Chordotonal organs: Nicotinamidase inhibitors selected from flonicamide.

[0219] (30) Allosteric modulators of the GABA-dependent chloride channel, preferably meto-diamides selected from broflanilide or isoxazoles selected from fluxametamide and isocycloseram.

[0220] (31) Baculoviruses, preferably granuloviruses (GVs) selected from Cydia pomonella GV and Thaumatotibia leucotreta (GV) or nucleopolyhedroviruses (NPVs) selected from Anticarsia gemmatalis MNPV, Flucypyriprol and Helicoverpa armigera NPV.

[0221] (32) Allosteric modulators (binding site II) of the nicotinic acetylcholine receptor selected from GS-omega / kappa-HXTX-Hv1a peptide.

[0222] (33) Calcium-activated potassium channel KCa2 modulators selected from Acynonapyr.

[0223] (34) Mitochondrial complex III electron transport inhibitors (non-Qo binding site) selected from flometoquine.

[0224] (36) Modulators of chordotonal organs (Undefined binding site), selected from dimpropyridaz. (UN) Compounds with unknown or unclear mechanism of action (the target protein responsible for biological activity is unknown or uncharacterized), selected from azadirachtin, benzoximates, benzopyrimoxane, bromopropylates, quinomethionate, dicofol, mancozeb, oxazosulfyl, pyridalyl, sulfur and lime sulfur.

[0225] (UNB) Bacterial agents (non- / ) with unknown or unclear mechanism of action (the target protein responsible for biological activity is unknown or not characterized), selected from Burkholderia spp. and Wolbachia pipientis (ZAP).

[0226] (UNE) Botanical essences, including synthetic, extracted and unrefined oils of unknown or unclear mechanism of action (the target protein responsible for biological activity is unknown or not characterized), selected from Chenopodium ambrosioides near ambrosioides extracts and glycerol and propanediol fatty acid monoesters of neem oil.

[0227] (UNF) Fungal agents of unknown or unclear mechanism of action (the target protein responsible for biological activity is unknown or uncharacterized), selected from BeauveriaBYC240191 Abroad

[0228] - 33 -bassiana -strains, Metarhizium anisopliae strain F52, and Paecilomyces fumosoroseus Apopka strain 97.

[0229] (UNM) Non-specific mechanical and physical disruptors (the target protein responsible for biological activity is unknown or uncharacterized), selected from silica and mineral oil.

[0230] (UNP) Peptides with unknown mechanism of action, selected from Ul-AGTX-Talb-QA.

[0231] Inhibitory nucleic acid molecules, preferably inhibitory ribonucleic acid molecules (RNAi), preferably inhibitory ribonucleic acid molecules (RNAi) selected from Vadescana (Varroa destructor calmodulin gene-specific double-stranded interfering EP15).

[0232] Other active ingredients selected from Afoxolaner, Bentioflumen, Bisulflufen, Chloroprallethrin, Cryolite, Cybenzoxasulfyl, Cycloxapride, Cyetpyrafen, Cyhalodiamides, Cyproflanilide (CAS 2375110-88-4), Esafoxolaner, epsilon-Metofluthrin, epsilon-Momfluthrin, Fenmezoditiaz, Fluchlordiniliprole, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluralaner, Fufenozide, Flupentiofenox, Flupyroxystrobin, Guadipyr, Heptafluthrin, Imidaclothiz, Indazapyroxamet, Iprodione, Isoflualaner, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Mivorilaner Modoflaner, Nicofluprole (CAS 1771741-86-6), Paichongding, Pioxaniliprole, Piperflanilide, Pyriminostrobin, Sarolaner, Spidoxamate, Spirobudifen, Sulfiflumen, Tetramethylfluthrin, Tetrachloroantraniliprole, Tigolaner, Tiapyrachlor, Tiorantraniliprole, Thiofluoximate, Tyclopyrazolor, Umifoxolaner; iodomethane; furthermore, preparations based on Bacillus firmus (1-1582, Votivo), Azadirachtin (BioNeem) and Ledprona (Calantha®),Pelargonic acid (known from WO 2023148028 Al) and the following compounds: l-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-lH-l,2,4-triazol-5-amine (known from WO 2006043635) (CAS 885026-50-6), 2-Chloro-N-[2-{l-[(2E)-3-(4-chlorophenyl)prop-2-en-l-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl] isonicotinamide (known from WO 2006003494) (CAS 872999-66-1), 3-(4-Chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3-(4-Chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonate (known from EP 2647626) (CAS1440516-42-6), PF1364 (known from JP 2010018586) (CAS 1204776-60-2), (3E)-3-[l-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-l,l,l-trifluoropropan-2-one (known from WO 2013144213) (CAS 1461743-15-6), N-[3-(Benzylcarbamoyl)-4-chlorophenyl]-l-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-lH-pyrazole-5-carboxamide (known from WO 2010051926) (CAS 1226889-14-0),5-Brom-4-chlor-N-[4-chlor-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chlor-2-pyridyl)pyrazol-3-carboxamid (bekannt aus CN 103232431) (CAS 1449220-44-3), 4-[5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]-2 -methyl-N-(cis-l-oxido-3-thietanyl)benzamid, 4-[5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N-(trans-l-oxido-3-thietanyl)benzamid und 4-[(5S)-5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N-(cis-l-oxido-3-thietanyl)benzamid (bekannt aus WO 2013050317 Al) (CAS 1332628-83-7), N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-BYC240191 Ausland,

[0233] - 34 - [(3,3,3-trifluorpropyl)sulfinyl]propanamid, (+)-N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluorpropyl)sulfinyl]propanamid und (-)-N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluorpropyl)sulfinyl]propanamid (bekannt aus WO 2013162715 A2, WO 2013162716 A2, US 20140213448 Al) (CAS 1477923-37-7), 5-[[(2E)-3-Chlor-2-propen-l-yl]amino]-l-[2,6-dichlor-4-(trifluormethyl)phenyl]-4-[(trifluormethyl)sulfinyl]-lH-pyrazol-3-carbonitrile (bekannt aus CN 101337937 A) (CAS 1105672-77-2), 3-Brom-N-[4-chlor-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-l-(3-chlor-2-pyridinyl)-lH-pyrazol-5-carboxamid, (Liudaibenjiaxuanan, bekannt aus CN 103109816 A) (CAS 1232543-85-9), N-[4-Chlor-2-[[(l,l-dimethylethyl)amino] carbonyl] -6-methylphenyl] - 1 -(3 -chlor-2-pyridinyl)-3 -(fluormethoxy)- IH-pyrazol-5-carboxamid (bekannt aus WO 2012034403 Al) (CAS 1268277-22-0), N-[2-(5-Amino-l,3,4-thiadiazol-2-yl)-4-chlor-6-methylphenyl]-3-brom-l-(3-chlor-2-pyridinyl)-lH-pyrazol-5-carboxamid (bekannt aus WO 2011085575 Al) (CAS 1233882-22-8), 4-[3-[2,6-Dichlor-4-[(3,3-dichlor-2-propen-l-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN 101337940 A) (CAS 1108184-52-6), (2E)- und 2(Z)-2-[2-(4-Cyanophenyl)-l-[3-(trifluormethyl)phenyl]ethyliden]-N-[4-(difluormethoxy)phenyl]hydrazincarboxamid (bekannt aus CN 101715774 A) (CAS 1232543-85-9), Cyclopropancarbonsäure-3-(2,2-dichlorethenyl)-2,2-dimethyl-4-(lH-benzimidazol-2-yl)phenylester (bekannt aus CN 103524422 A) (CAS 1542271-46-4), (4aS)-7-Chlor-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluormethyl)thio]phenyl]amino]carbonyl]indeno[l,2-e][l,3,4]oxadiazin-4a(3H)-carbonsäuremethylester (bekannt aus CN 102391261 A) (CAS 1370358-69-2), 6-Desoxy-3-O-ethyl-2,4-di-O-methyl-l-[N-[4-[l-[4-(l,l,2,2,2-pentafluorethoxy)phenyl]-lH-l,2,4-triazol-3-yl]phenyl]carbamat]-a-L-mannopyranose (bekannt aus US 2014 / 0275503 Al) (CAS 1181213-14-8), 8-(2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octan (CAS 1253850-56-4), (8-anti)-8-(2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3-azabicyclo[3.2. l]octan (CAS 933798-27-7), (8-syn)-8-(2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octan (bekannt aus WO 2007040280 Al, WO 2007040282 Al) (CAS 934001-66-8), N-[4-(Aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-brom-l-(3-chlor-2-pyridinyl)-lH-pyrazol-5 -carboxamid (bekannt aus CN 103265527 A) (CAS 1452877-50-7), 3-(4-Chlor-2,6-dimethylphenyl)-8-methoxy-l-methyl-l,8-diazaspiro[4.5]decan-2,4-dion (bekannt aus WO 2014187846 Al) (CAS 1638765-58-8), 3-(4-Chlor-2,6-dimethylphenyl)-8-methoxy-l-methyl-2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl carboxylic acid ethyl ester (known from WO 2010066780 Al, WO 2011151146 Al) (CAS 1229023-00-0), W[l-(2,6-Difluorophenyl)-lH-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from WO 2014053450 Al) (CAS 1594624-87-9), N-[2-(2,6-Difluorophenyl)-2H-l,2,3-triazol-4-yl]-2-(trifluoromethyl)benzamide (known from WO 2014053450 Al) (CAS 1594637-65-6), N-[l-(3,5-difluoro-2-pyridinyl)-lH-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from WO 2014053450 Al) (CAS 1594626-19-3), A-[3-Chloro-l-(3-pyridinyl)-lEI-pyrazol-4-yl]-2-(methylsulfonyl)-propanamide (known from WO 2019 / 236274 Al) (CAS 2396747-83-2), N-[2-Bromo-4-[l,2,2,2-tetrafluoro-l-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-2-fluoro-3-[(4-fluorobenzoyl)amino]-benzamide (known BYC240191 abroad,

[0234] - 35 -aus WO 2019059412 Al) (CAS 1207977-87-4), 2-(5-Cyclopropyl-3-ethylsulfonyl-2-pyridyl)-5-(trifluormethylsulfmyl)-l,3-benzoxazol (bekannt aus WO 2017146226 Al) (CAS 2128706-04-5), 6-(5-Cyclopropyl-3-ethylsulfonyl-2-pyridyl)-2,2-difluor-7-methyl-[l,3]dioxolo[4,5-f|benzimidazol (bekannt aus WO 2020013147 Al) (CAS 2408220-91-5), l-[6-(2,2-Difluor-7-methyl-[l,3]dioxol[4,5-f|benzimidazol-6-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropan-carbonitril (bekannt aus WO 2020013147 Al) (CAS 2408220-94-8), 2-(3-Ethylsulfonyl-2-pyridyl)-5-(2,2,3,3,3-pentafluorpropoxy)pyrazin (bekannt aus WO 2017065228 Al) (CAS 2095470-94-1), 5-[[(lR,3R)-3-[3,5-Bis(trifluormethyl)phenyl]-2,2-dichlor-cyclopropancarbonyl]amino]-2-chlor-N-[3-[(2,2-difluoracetyl)amino]-2,4-difluor-phenyl]benzamid (bekannt aus WO 2022072650 Al) (CAS 2649032-72-2), 2-Chlor-N-[3-[(2,2-difluoracetyl)amino]-2,4-difluor-phenyl]-5-[[rel-(lR,3R)-3-[3,5-bis(trifluormethyl)phenyl]-2,2-dichloro-cyclopropanecarbonyl]amino]benzamide (known from WO 2018071327 Al) (CAS 2220132-55-6).,

[0235] Nematicides

[0236] The active ingredients identified here by their common names are well-known and described, for example, in the Pesticide Manual (“The Pesticide Manual,” 16th ed., British Crop Protection Council 2012) or can be found on the internet (e.g., http: / / www.alanwood.net / pesticides). The classification is based on the Nematicide IRAC Mode of Action Classification Groups current at the time of filing this patent application.

[0237] (Group Nl) Acetylcholinesterase (AChE) inhibitors, preferably (N-1A) carbamates selected from aldicarb, benfuracarb, carbofuran, carbosulfan and thiodicarb, or (N-1B) organophosphates selected from cadusafos, ethoprofos, fenamiphos, fosthiazate, imicyafos, phorate and terbufos.

[0238] (Group N-2) Allosteric modulators of the glutamate-gated chloride channel (GluCl), preferably avermectins selected from abamectin and emamectin benzoate.

[0239] (Group N-3) Inhibitors of mitochondrial complex II electron transport, in particular inhibitors of succinate coenzyme Q reductase, preferably pyridinyl ethylbenzamides selected from cyclobutrifluram and fluopyram.

[0240] (Group N-4) Modulators of lipid synthesis / growth control, in particular inhibitors of acetyl-CoA carboxylase, preferably tetronic and tetramic acid derivatives selected from spirotetramate. (Group N-UN) Compounds of unknown or unclear mode of action and various compounds selected from fluensulfones, fluazaindolizines, furfural, iprodione, and tioxazafen. (Group N-UNX) Compounds of unknown or unclear mode of action: Suspected multisite inhibitors, preferably volatile sulfur-generating compounds selected from carbon disulfide and dimethyl disulfide (DMDS), or carbon disulfide-releasing compounds selected from sodium tetrathiocarbonate, or alkyl halides selected from methyl bromide and methyl iodide (iodomethane), or halogenated hydrocarbons selected from 1,2-dibromo-3-BYC240191 Abroad

[0241] - 36-chloropropane (DBCP) and 1,3-dichloropropene, or chloropicrin, or methyl isothiocyanate-generating compounds selected from allyl isothiocyanate, diazomet, metam potassium, and metam sodium. (Group N-UNB) Bacterial agents (non- / ) of unknown or unclear mode of action, preferably a bacterium or derived from a bacterium selected from Burkholderia spp., e.g., rinojensis A396, Bacillus spp., e.g., firmus, licheniformis, amyloliquefaciens, or subtilis, Pasteuria spp., e.g., penetrans or nishizawae, Pseudomonas spp., e.g., chlororaphis or fluorescens, and Streptomyces spp., e.g., lydicus, dicklowii, or albogriseolus.

[0242] (Group N-UNF) Fungal products of unknown or unclear mode of action, preferably a fungus or derived from a fungus selected from Actinomyces spp., e.g. streptococcus, Arthrobotrys spp., e.g. oligospora, Aspergillus spp., e.g. niger, Muscodor spp., e.g. albus, Myrothecium spp., e.g. verrucaria, Paecilomyces spp., e.g. lilacinus (Purpureocillium lilacinum), carneus or fumosoroseus, Pochonia spp., e.g. chlamydosporia, and Trichoderma spp., e.g. harzianum, virens, atroviride or viride.

[0243] (Group N-UNE) Botanical or animal-derived products, including synthetic extracts and unrefined oils, of unknown or unclear mode of action, preferably botanical or animal-derived products selected from azadirachtin, essential oils, camellia seed cake, garlic extract, Pongamia oil, Quillaja saponaria-ExP X and terpenes, e.g. carvacrol, geraniol and thymol.

[0244] Other active ingredients selected from trifluenfuronate. Other bacterial agents selected from Bacillus spp., e.g., paralicheniformis and velezensis. Other fungal agents selected from Aspergillus spp., e.g., niger and their metabolites, selected from oxalic acid.

[0245] Fungicides

[0246] The active ingredients specified here by their “Common Name” are known and are described, for example, in the “Pesticide Manual” (16th edition, British Crop Protection Council) or can be researched on the Internet (e.g., www.alanwood.net / pesticides).

[0247] All the aforementioned mixture components of classes (1) to (15) can, if their functional groups allow, form salts with suitable bases or acids. If one of the mixture components can exist in tautomeric form, such a compound is to be understood as including corresponding tautomeric forms in the preceding and subsequent sections.

[0248] 1) Inhibitoren der Ergosterol-Biosynthese, beispielsweise (1.001) Cyproconazol, (1.002) Difenoconazol, (1.003) Epoxiconazol, (1.004) Fenbuconazol, (1.005) Fenhexamid, (1.006) Fenpropidin, (1.007) Fenpropimorph, (1.008) Fenpyrazamin, (1.009) Fluoxytioconazol, (1.010) Fluquinconazol, (1.011) Flutriafol, (1.012) Hexaconazol, (1.013) hnazalil, (1.014) Imazalilsulfat, (1.015) Ipconazol, (1.016) Ipfentrifluconazol, (1.017) Mefentrifluconazol, (1.018) Metconazol, (1.019) Myclobutanil, (1.020)BYC240191 Ausland

[0249] - 37 - Paclobutrazol, (1.021) Penconazol, (1.022) Prochloraz, (1.023) Propiconazol, (1.024) Prothioconazol, (1.025) Pyrisoxazol, (1.026) Spiroxamin, (1.027) Tebuconazol, (1.028) Tetraconazol, (1.029) Triadimenol, (1.030) Tridemorph, (1.031) Triticonazol, (1.032) 4-[[6-[(2R)-2-(2,4-Difluorphenyl)-l,l-difluor-2-hydroxy-3-(5-thioxo-4H-l,2,4-triazol-l-yl)propyl]-3-pyridyl]oxy]benzonitril, (1.033) 4-[[6-[(2S)-2-(2,4-Difluorphenyl)- 1 , 1 -difluor-2-hydroxy-3 -(5 -thioxo-4H- 1 ,2,4-triazol- 1 -yl)propyl] -3 -pyridyl] oxy] benzonitril, (1.034) (2R)-2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-l-(lH-l,2,4-triazol- 1 -yl)propan-2-ol, (1.035) (2S)-2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1H- 1 ,2,4-triazol-l-yl)propan-2-ol, (1.036) l-({(2R,4S)-2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-4-methyl-l,3-dioxolan-2-yl}methyl)-lH-l,2,4-triazol, (1.037) l-({(2S,4S)-2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-4-methyl-l,3-dioxolan-2-yl}methyl)-lH-l,2,4-triazol, (1.038) 2-[6-(4-Bromphenoxy)-2-(trifluormethyl)-3-pyridyl] - 1 -( 1 ,2,4-triazol- 1 -yl)propan-2-ol, (1.039) 2-[6-(4-Chlorphenoxy)-2-(trifluormethyl)-3 -pyridyl] - 1 -( 1 ,2,4-triazol- 1 -yl)propan-2-ol, ( 1.040) 3 -[2-( 1 -Chlorcyclopropyl) -3 -(3 -chlor-2-fluorphenyl)-2-hydroxypropyl]imidazol-4-carbonitril, (1.041) 2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-2-hydroxy-3-(lH-l,2,4-triazol-l-yl)propansäuremethylester, (1.042) (2R)-2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-2-hydroxy-3-( 1H- 1 ,2,4-triazol- 1 -yl)propansäuremethylester, ( 1.043) (S)-2-[2-Chlor-4-(4-chlorphenoxy)phenyl] -2-hydroxy-3 -( 1H- 1 ,2,4-triazol- 1 -yl)propansäuremethylester, (1.044) N'-(2,5-Dimethyl -4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamid, (1.045) N'-(2-Chlor-4-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamid, (1.046) N'-(2-Chlor-4-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamid, (1.047) N'-(2-Chlor-5 -methyl -4-phenoxyphenyl)-N-ethyl-N-methylimidoformamid, (1.048) N'-(4-Benzyl-2-chlor-5-methylphenyl)-N-ethyl-N-methylformimidamid, ( 1.049) N'-[2-Chlor-4-(2-fluorphenoxy)-5-methylphenyl] -N-ethyl-N-methylimidoformamid, (1.050) N'-[5-Brom-6-(2,3-dihydro-lH-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamid, (1.051) N'-{4-[(4,5-Dichlor-l,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamid, (1.052) N'-{5-Brom-2-methyl-6-[(l-propoxypropan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.053) N'-{5-Brom-6-[(lR)-l-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3 -yl} -N-ethyl-N-methylimidoformamid, (1.054) N'-{5 -Brom-6-[( lS)-l-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.055) N'-{5-Brom-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.056) N'-{5-Brom-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidofbrmamid, (1.057) N'-{5 -Brom-6-[ 1 -(3 ,5 -difluorphenyl)ethoxy] -2-methylpyridin-3 -yl} -N-ethyl-N-methylimidoformamid, (1.058) N-Isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluor-l-hydroxy-l-phenylethyl)phenyl]-N-methylimidoformamid, (1.059) 4-[(E)-[Ethyl(methyl)-amino]methylenamino]-2,5-dimethylbenzoesäure-p-tolylmethylester, (1.060) N'-(2,5-Dimethyl-4-phenoxy-phenyl) -N -ethyl -N -methyl -formamidin .

[0250] 2) Inhibitoren der Atmungskette am Komplex I oder II, beispielsweise (2.001) Benzovindiflupyr, (2.002) Bixafen, (2.003) Boscalid, (2.004) Carboxin, (2.005) Cyclobutrifluram, (2.006) Flubeneteram, (2.007) Fluindapyr, (2.008) Fluopyram, (2.009) Flutolanil, (2.010) Fluxapyroxad, (2.011) Furametpyr, (2.012) Inpyrfluxam, (2.013) Isofetamid, (2.014) Isoflucypram, (2.015) Isopyrazam, (2.016) Penflufen, (2.017)BYC240191 Ausland

[0251] - 38 - Penthiopyrad, (2.018) Pydiflumetofen, (2.019) Pyrapropoyn, (2.020) Pyraziflumid, (2.021) Sedaxan, (2.022) Thifluzamid (auch bekannt als Trifluzamid), (2.023) 5,8-Difluor-N-[2-(2-fluor-4-{[4- (trifluormethyl)pyridin-2-yl] oxy} phenyl)ethyl] chinazolin-4-amin, (2.024) 5 -Chlor-N - [2- [ 1 -(4-chlorphenyl)pyrazol-3-yl]oxyethyl]-6-ethylpyrimidin-4-amin, (2.025) N-[2-[l-(4-Chlorphenyl)pyrazol-3-yl]oxyethyl]chinazolin-4-amin, (2.026) l-Methyl-3-(trifluormethyl)-N-[2'-(trifluormethyl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (2.027) 2-Fluor-6-(trifluormethyl)-N-(l, l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)benzamid, (2.028) 3-(Difluormethyl)-l-methyl-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH-pyrazol-4-carboxamid, (2.029) 3-(Difluormethyl)-l-methyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.030) 3-(Difluormethyl)-N-[(3R)-7-fluor-l, 1,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazol-4-carboxamid, (2.031) 3-(Difluormethyl)-N-[(3S)-7-fluor- 1 , 1 ,3-trimethyl-2,3-dihydro- lH-inden-4-yl] - 1 -methyl- lH-pyrazol-4-carboxamid, (2.032) N-[( 1 R,4S)-9-(Dichlormethylen)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalin-5 -yl] -3 -(difluormethyl)- 1 -methyl- lH-pyrazol-4-carboxamid, (2.033) N-[(lS,4R)-9-(Dichlormethylen)-l,2,3,4-tetrahydro-l,4-methanonaphthalin-5-yl] -3-(difluormethyl)- 1 -methyl- lH-pyrazol-4-carboxamid, (2.034) N-[ 1 -(2,4- Dichlorphenyl)- 1 -methoxypropan-2-yl] -3 -(difluormethyl)- 1 -methyl- lH-pyrazol-4-carboxamid, (2.035) 5-Chlor-l,3-dimethyl-N-[(3S)-l,l,3-trimethyl-3H-isobenzofuran-4-yl]pyrazol-4-carboxamid, (2.036) 5-Chlor-l,3-dimethyl-N-[(3R)-l,l,3-trimethyl-3H-isobenzofuran-4-yl]pyrazol-4-carboxamid, (2.037) N-[2-[(lS)-l,3-Dimethylbutyl]phenyl]-5-fluor-l,3-dimethyl-pyrazol-4-carboxamid, (2.038) N-[2-[(lR)-l,3-Dimethylbutyl]phenyl]-5-fluor-l,3-dimethyl-pyrazol-4-carboxamid, (2.039) 3-(Difluormethyl)-N-methoxy- 1 -methyl -N-[( 1 S)- 1 -methyl -2-(2, 4, 6-trichlorphenyl)ethyl]pyrazol-4-carboxamid, (2.040) 3-(Difluormethyl)-N-methoxy- 1 -methyl -N-[( 1R)- 1 -methyl-2-(2,4,6-trichlorphenyl)ethyl]pyrazol-4-carboxamid, (2.041) N-[2-[(lS)-l,3-Dimethylbutyl]-3-thienyl]-l-methyl-3-(trifluormethyl)pyrazol-4-carboxamid, (2.042) N-[2-[( 1 R)- 1 ,3 -Dimethylbutyl] -3 -thienyl] - 1 -methyl-3 -(trifluormethyl)pyrazol-4-carboxamid, (2.043) N-[rac-(lS,2S)-2-(2,4-Dichlorphenyl)cyclobutyl]-2-(trifluormethyl)nicotinamid, (2.044) 2-(Difluormethyl)-N-(3-ethyl-l,l-dimethyl-indan-4-yl)pyridin-3-carboxamid.

[0252] 3) Inhibitoren der Atmungskette am Komplex III, beispielsweise (3.001) Ametoctradin, (3.002) Amisulbrom, (3.003) Azoxystrobin, (3.004) Coumethoxystrobin, (3.005) Coumoxystrobin, (3.006) Cyazofamid, (3.007) Dimoxystrobin, (3.008) Enoxastrobin, (3.009) Famoxadon, (3.010) Fenamidon, (3.011) Fenpicoxamid, (3.012) Florylpicoxamid, (3.013) Flufenoxystrobin, (3.014) Fluoxastrobin, (3.015) Kresoxim-methyl, (3.016) Mandestrobin, (3.017) Metarylpicoxamid, (3.018) Metominostrobin, (3.019) Metyltetraprol, (3.020) Orysastrobin, (3.021) Picoxystrobin, (3.022) Pyraclostrobin, (3.023) Pyrametostrobin, (3.024) Pyraoxystrobin, (3.025) Pyribencarb, (3.026) Trifloxystrobin, (3.027) (2E)-2- {2-[({[(lE)-l-(3-{[(E)-l-fluor-2-phenylvinyl]oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2- (methoxyimino)-N-methylacetamid, (3.028) (2E,3Z)-5-{[l-(4-Chlor-2-fluorphenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamid, (3.029) (2E,3Z)-5-{[l-(4-Chlorphenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamid, (3.030) (2R)-2-{2-[(2,5- Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.031) (2S)-2-{2-[(2,5- Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.032) (Z,2E)-5-[l-(2,4-BYC240191 Ausland.

[0253] - 39 - Dichlorphenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enamid, (3.033) (Z)-2-(5- Cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-ensäuremethylester, (3.034) (Z)-2-(5-Cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-ensäuremethylester, (3.035) (Z)-3-Methoxy-2-[2-methyl-5-(3-propylpyrazol-l-yl)phenoxy]prop-2-ensäuremethylester, (3.036) (Z)-3-Methoxy-2-[2-methyl-5-[3-(trifluormethyl)pyrazol-l-yl]phenoxy]prop-2-ensäuremethylester, (3.037) (Z)-2-[5-(3-Isopropylpyrazol- 1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-ensäureethylester, (3.038) {5-[3-(2,4-Dimethylphenyl)-lH-pyrazol- 1 -yl] -2 -methylbenzyl} carbamidsäuremethylester, (3.039) (2E)-2-Methoxyimino-N-methyl-2-[3 -methyl-2-[[(E)-l-[3-(trifluormethyl)phenyl]ethylideneamino]oxymethyl]phenyl]acetamid, (3.040) (2E)- 2-[2-[[(E)-l-(3,5-Difluorphenyl)ethylideneamino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamid, (3.041) (2S)-2-[(3-Hydroxy-4-methoxypyridin-2-carbonyl)amino]propansäure[rac-2-(4-brom-7-fluorindol-l-yl)-l-methylpropyl]ester, (3.042) (2S)-2-[(3-Acetoxy-4-methoxypyridin-2-carbonyl)amino]propansäure[rac-2-(7-brom-4-fluorindol-l-yl)-l-methylpropyl]ester, (3.043) (2S)-2-[(3-Hydroxy-4-methoxypyridin-2-carbonyl)amino]propansäure-[rac-2-(7-bromindol- 1 -yl)- 1 -methylpropyl]ester, (3.044) (2S)-2-[(3-Hydroxy-4-methoxypyridin-2-carbonyl)amino]propansäure[rac- 2-(3,5-dichlor-2-pyridyl)-l-methylpropyl]ester, (3.045) (2S)-2-[(3-Acetoxy-4-methoxypyridin-2-carbonyl)amino]propansäure[(lS)-l-[l-(l-naphthyl)cyclopropyl]ethyl]ester, (3.046) (2S)-2-[(3- Hydroxy-4-methoxypyridin-2-carbonyl)amino]propansäure [( 1 S)- 1 -[ 1 -( 1 -naphthyl)cyclopropyl] -ethyl]ester, (3.047) (2S)-2-[[3-(Acetoxymethoxy)-4-methoxypyridin-2-carbonyl]amino]propan-säure [( 1 S)- 1 -[ 1 -( 1 -naphthyl)cyclopropyl]ethyl]ester, (3.048) 2-Methylpropansäure-[2-[[( 1 S)-2- [(lRS,2SR)-2-(3,5-dichlor-2-pyridyl)-l-methylpropoxy]-l-methyl-2-oxoethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethylester, (3.049) 2-[Cyan-(2,6-difluor-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamid, (3.050) 2-[Cyan-(2,6-difluor-4-pyridyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazol-4-carboxamid, (3.051) 2-[Cyan-(2,6-difluor-4-pyridyl)amino]-N-hexyl-5-methyl-thiazol-4-carboxamid, (3.052) 2-[Acetyl-(2,6-difluor-4-pyridyl)amino]-N-(2,2-dimethyl-cyclobutyl)-5-methyl-thiazol-4-carboxamid, (3.053) 2-[(2,6-Difluor-4-pyridyl)-(2-methylpropanoyl)-amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamid, (3.054) 2-[(2,6-Difluor-4-pyridyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamid, (3.055) 2-[(2,6-Difluor-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-N-(tetrahydrofuran-3-carbonyl)thiazol-4-carboxamid, (3.056) 2-[(2,6-Difluor-4-pyridyl)-(tetrahydrofuran- 3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamid, (3.057) 2-[(2,6-Difluor- 4-pyridyl)-(oxetan-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamid, (3.058) 2-[(2,6-Difluor-4-pyridyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamid, (3.059) N-(3-Ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxy-benzamid.

[0254] 4) Inhibitoren der Mitose und Zellteilung, beispielsweise (4.001) Carbendazim, (4.002) Diethofencarb, (4.003) Ethaboxam, (4.004) Fluopicolid, (4.005) Fluopimomid, (4.006) Metrafenon, (4.007) Pencycuron, (4.008) Pyridachlometyl, (4.009) Pyriofenon (Chlazafenon), (4.010) Thiabendazol, (4.011) Thiophanat-methyl, (4.012) Zoxamid, (4.013) 3-Chlor-5-(4-chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin,BYC240191 Ausland

[0255] - 40 - (4.014) 3 -Chlor-5 -(6-chlorpyridin-3 -yl)-6-methyl-4-(2,4,6-trifluorphenyl)pyridazin, (4.015) 4-(2-Brom- 4-fluorphenyl)-N-(2,6-difluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.016) 4-(2-Brom-4-fluorphenyl)-N-(2-brom-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.017) 4-(2-Brom-4-fluorphenyl)-N-(2-bromphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.018) 4-(2-Brom-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.019) 4-(2-Brom-4-fluorphenyl)-N-(2-chlorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.020) 4-(2-Brom-4-fluorphenyl)-N-(2-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.021) 4-(2-Chlor-4-fluorphenyl)-N-(2,6-difluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.022) 4-(2-Chlor-4-fhiorphenyl)-N-(2-chlor-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.023) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.024) 4-(2-Chlor-4-fluorphenyl)-N-(2-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.025) 4-(4-Chlorphenyl)-5-(2,6-difluorphenyl)-3,6-dimethylpyridazin, (4.026) N-(2-Brom-6-fluorphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.027) N-(2-Bromphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.028) N-(4-Chlor-2,6-difluorphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin.

[0256] 5) Compounds capable of multisite action, for example (5.001) Bordeaux mixture, (5.002) Captafol, (5.003) Captan, (5.004) Chlorothalonil, (5.005) Copper hydroxide, (5.006) Copper maphthenate, (5.007) Copper oxide, (5.008) Copper oxychloride, (5.009) Copper(II) sulfate, (5.010) Dithianon, (5.011) Dodine, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, (5.016) Metiram zinc, (5.017) Oxine copper, (5.018) Propineb, (5.019) Sulfur and sulfur preparations including Calcium polysulfide, (5,020) thiram, (5,021) zineb, (5,022) ziram, (5,023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][l,4]dithiino[2,3-c][l,2]thiazole-3-carbonitrile.

[0257] 6) Compounds capable of triggering host defense, for example (6.001) Acibenzolar-5-methyl, (6.002) Fosetyl aluminum, (6.003) Fosetyl calcium, (6.004) Fosetyl sodium, (6.005) Isotianil, (6.006) Phosphorous acid and its salts, (6.007) Probenazol, (6.008) Tiadinil.

[0258] 7) Inhibitors of amino acid and / or protein biosynthesis, for example (7.001) Cyprodinil, (7.002) Kasugamycin, (7.003) Kasugamycin hydrochloride hydrate, (7.004) Oxytetracycline, (7.005) Pyrimethanil.

[0259] 8) Inhibitors of ATP production, for example (8.001) Silthiofam.

[0260] 9) Inhibitors of cell wall synthesis, for example (9.001) Benthiavalicarb, (9.002) Dimethomorph, (9.003) Flumorph, (9.004) Iprovalicarb, (9.005) Mandipropamid, (9.006) Pyrimorph, (9.007) Valifenalate, (9.008) (2E)-3-(4-tert-Butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one, (9.009) (2Z)-3-(4-tert-Butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one.

[0261] 10) Inhibitors of lipid synthesis or lipid transport or membrane synthesis, for example (10.001) fluoxapiproline, (10.002) natamycin, (10.003) oxathiapiproline, (10.004) propamocarb, (10.005) propamocarb hydrochloride, (10.006) propamocarb fosetylate, (10.007) tolclofos methyl, (10.008) l-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-BYC240191 Abroad

[0262] - 41 -methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]ethanon, (10.009) l-(4-{4-[(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]ethanon, (10.010) 2-{(5R)-3-[2-(l-{[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-1 ,3 -thiazol-4-yl] -4,5 -dihydro- 1 ,2-oxazol-5 -yl} -3 -chlorphenylmethansulfonate, (10.011) 2- { (5 S)-3 -[2-( 1 -{[3,5-bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorphenylmethansulfonate, (10.012) 3-[2-(l-{[5-methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-l,5-dihydro-2,4-benzodioxepin-6-ylmethansulfonat, (10.013) 9-Fluor-3-[2-(l-{[5-methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl] - 1 ,5 -dihydro-2,4-benzodioxepin-6-ylmethansulfonat, (10.014) 3 -[2-( 1 - { [3,5 - Bis(difluoromethyl)- IH-pyrazol- 1 -yl]acetyl}piperidin-4-yl)- 1,3-thiazol-4-yl]- 1,5-dihydro-2,4-benzodioxepin-6-ylmethanesulfonate, (10,015) 3-[2-(l-{ [3 ,5-Bis(difluoromethyl)-IH-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxepin-6-ylmethanesulfonate.

[0263] 11) Inhibitors of melanin biosynthesis, for example (11.001) tolprocarb, (11.002) tricyclazole. 12) Inhibitors of nucleic acid synthesis, for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0264] 13) Inhibitors of signal transduction, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozoline.

[0265] 14) Compounds that can act as uncouplers, for example (14.001) Fluazinam, (14.002) Meptyldinocap.

[0266] 15) Other compounds, for example (15.001) abscisic acid, (15.002) aminopyrifene, (15.003) benthiazole, (15.004) bethoxazine, (15.005) capsimycin, (15.006) carvone, (15.007) quinomethionate, (15.008) chlorinconazide, (15.009) cufraneb, (15.010) cyflufenamide, (15.011) cymoxanil, (15.012) cyprosulfamide, (15.013) dipymetitron, (15.014) D-tagatose, (15.015) feneptamidoquine, (15.016) flufenoxadiazam, (15.017) flumethylsulfamide, (15,018) flutianil, (15,019) ipflufenoquine, (15,020) methyl isothiocyanate, (15,021) mildiomycin, (15,022) nickel dimethyl dithiocarbamate, (15,023) nitrothalisopropyl, (15,024) oxyfenthiine, (15,025) pentachlorophenol and Salts, (15,026) picarbutrazox, (15,027) quinofumelin, (15,028) tebufloquine, (15,029) tecloftalam, (15,030) tolnifanide, (15,031) 2-(6-benzylpyridin-2-yl)quinazoline, (15,032) 2-[6-(3-Fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15,033) 2-phenylphenol and salts, (15.034) 4-Amino-5-fluorpyrimidin-2-ol (tautomere Form: 4-Amino-5-fluorpyrimidin-2(lH)-on), (15.035) 4-Oxo-4-[(2-phenylethyl)amino]butansäure, (15.036) 5-Amino-l,3,4-thiadiazol-2-thiol, (15.037) 5-Chlor-N'-phenyl-N'-(prop-2-in-l-yl)thiophen-2-sulfonohydrazid, (15.038) 5-Fluor-2-[(4-fluorbenzyl)oxy]pyrimidin-4-amin, (15.039) 5-Fluor-2-[(4-methylbenzyl)oxy]pyrimidin-4-amin, ( 15.040) { 6-[( { [(Z)-( 1 -Methyl- lH-tetrazol-5 -yl)(phenyl)methylen] amino} oxy)methyl]pyridin-2-yl} carbamidsäurebut-3 -in- 1 -yle ster, (15.041) (2Z) -3 -Amino-2-cyano-3-phenylacrylsäureethylester, (15.042) 2-[Acetyl-[2-ethylsulfonyl-4- (trifluormethyl)benzoyl]amino]-5-(trifIuormethoxy)benzoesäuremethylester, (15.043) N-Acetyl-N-[2-BYC240191 Ausland.

[0267] -42 -bromo-4-(trifluormethoxy)phenyl] -2 -ethylsulfonyl -4-(trifluormethyl)benzamid, (15.044) Phenazin- 1 -carbonsäure, (15.045) 3,4,5-Trihydroxybenzoesäurepropylester, (15.046) Chinolin-8-ol, (15.047) Chinolin-8-ol-sulfat (2:1), (15.048) (2R)-2-Benzyl-N-(8-fluor-2-methyl-3-chinolyl)-2,4-dimethylpentanamid, (15.049) (2S)-2-Benzyl-N-(8-fluor-2-methyl-3-chinolyl)-2,4-dimethylpentanamid, (15.050) 1 -(4,5 -Dimethyl- IH-benzimidazol- 1 -yl)-4,4-difluor-3 ,3 -dimethyl-3 ,4-dihydroisochinolin, (15.051) l-(4,5-Dimethylbenzimidazol-l-yl)-4,4,5-trifluor-3,3-dimethylisochinolin, (15.052) l-(5- (Fluormethyl)-6-methylpyridin-3 -yl)-4,4-difluor-3 ,3 -dimethyl-3 ,4-dihydroisochinolin, (15.053) 1 -( 5 , 6 -Dimethylpyridin-3 -yl)-4,4-difluor-3 ,3 -dimethyl-3 ,4-dihydroisochinolin, (15.054) 1 -(6-(Difluormethyl)-5-methoxypyridin-3-yl)-4,4-difluor-3,3-dimethyl-3,4-dihydroisochinolin, (15.055) l-(6-(Difluormethyl)-5 -methyl -pyridin-3 -yl)-4,4-difluor-3 ,3 -dimethyl-3 ,4-dihydroisochinolin, ( 15.056) 4,4-Difluor-3 ,3 -dimethyl- 1 -(7-methylpyrazolo [ 1 ,5 -a]pyridin-3 -yl)isochinolin, (15.057) 1 -(6,7-Dimethylpyrazolo[ 1,5-a]pyridin-3-yl)-4,4,5-trifluor-3,3-dimethylisochinolin, (15.058) l-(6,7-Dimethylpyrazolo[l,5-a]pyridin-3 -yl)-4,4-difluor-3 ,3 -dimethyl-3 ,4-dihydroisochinolin, (15.059) 2- {2-Fluor-6-[(8-fluor-2-methylchinolin-3 -yl)oxy]phenyl}propan-2-ol, (15.060) 3 -(4,4,5 -Trifluor-3 ,3 -dimethyl-3 ,4-dihydroisochinolin- 1 -yl)chinolin, (15.061) 3 -(4, 4-Difluor-3 ,3 -dimethyl-3 ,4-dihydroisochinolin- 1 -y 1) - 8 -fluorchinolin, (15.062) 3-(4,4-Difluor-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)chinolin, (15.063) 3 -(5 -Fluor-3 ,3 ,4, 4-tetramethyl-3 ,4-dihydroisochinolin- 1 -yl)chinolin, (15.064) 4,4-Difluor-3 ,3 -dimethyl- 1 -(4-methylbenzimidazol- 1 -yl)isochinolin, (15.065) 4, 4-Difluor-3 ,3 -dimethyl- 1 -(6-methylpyrazolo [ 1 ,5 -a]pyridin-3 -yl)isochinolin, (15.066) 5 -Brom- 1 -(5 ,6-dimethylpyridin-3 -yl)-3 ,3 -dimethyl-3, 4-dihydroisochinolin, ( 15.067) 7,8-Difluor-N-[rac- 1 -benzyl- 1 ,3-dimethylbutyl]chinolin-3-carboxamid, ( 15.068) 8-Fluor-3 -(5 -fluor-3 ,3 ,4,4-tetramethyl-3 ,4-dihydroisochinolin- 1 -yl)chinolin, (15.069) 8-Fluor-3 -(5 -fluor-3 ,3 -dimethyl-3 ,4-dihydroisochinolin- 1 -yl)chinolin, (15.070) 8-Fluor-N-(4,4,4-trifluor-2-methyl-l-phenylbutan-2-yl)chinolin-3 -carboxamid, (15.071) 8-Fluor-N-[(lR)-l-[(3-fluorphenyl)methyl] - 1 ,3 -dimethylbutyl] chinolin-3 -carboxamid, (15.072) 8 -Fluor-N - [( 1 S) - 1 - [(3 -fluorphenyl)methyl] - 1 ,3-dimethylbutyl]chinolin-3-carboxamid, (15.073) 8-Fluor-N-[(2S)-4,4,4-trifluor-2-methyl-l-phenylbutan-2-yl] chinolin-3 -carboxamid, (15.074) 8-Fluor-N-[rac-l-[(3-fluorphenyl)methyl] - 1 ,3 -dimethylbutyl] chinolin-3 -carboxamid, (15.075) 9-Fluor-2,2-dimethyl-5 -(chinolin-3-yl)-2,3-dihydro- 1 ,4-benzoxazepin, (15.076) N-(2,4-Dimethyl- 1 -phenylpentan-2-yl)-8-fluorchinolin-3 -carboxamid, (15.077) N-[(1R)-1 -Benzyl- 1 , 3 -dimethylbutyl] -7,8 -difluorchinolin-3 -carboxamid, (15.078) N-[(lS)-l-Benzyl-l,3-dimethylbutyl]-7,8-difluorchuinolin-3-carboxamid, (15.079) N-[(2S)-2,4-Dimethyl-l-phenylpentan-2-yl]-8-fluorquinolin-3-carboxamid, (15.080) rac-2-Benzyl-N-(8-fluor-2-methyl-3-chinolyl)-2,4-dimethylpentanamid, (15.081) (5RS)-3-[3-(3-Cyclopropyl-2-fluorphenoxy)-6-methylpyridazin-4-yl]-5-(2,4-dimethylbenzyl)-5,6-dihydro-4H-l,2,4-oxadiazin, (15.082) (5 S)-3 -[3 -(3 -Cyclopropyl -2 -fluorophenoxy)-6-methylpyridazin-4-yl] -5 -(2,4-dimethylbenzyl)-5 ,6-dihydro-4H- 1 ,2,4-oxadiazin, (15.083) (5RS)-5 -(4-Brom-2-methylbenzyl)-3 -[3 -(3 -chlor-2-fluorphenoxy)-6-methylpyridazin-4-yl]-5,6-dihydro-4H-l,2,4-oxadiazin, (15.084) (5RS)-3-[3-(3-Chlor-2-fluorphenoxy)-6-methylpyridazin-4-yl]-5-(2-chlor-4-methylbenzyl)-5,6-dihydro-4H-l,2,4-oxadiazin, (15.085) (5S)-5-(4-Brom-2-methylbenzyl)-3-[3-(3-chlor-2-fluorphenoxy)-6-methylpyridazin-4-yl]-5,6-BYC240191 Ausland.

[0268] -43 -dihydro-4H-l,2,4-oxadiazin, (15.086) (5R)-3-[3-(3-Chlor-2-fluorphenoxy)-6-methylpyridazin-4-yl]-5-(2-chlor-4-methylbenzyl)-5,6-dihydro-4H-l,2,4-oxadiazin, (15.087) (5S)-3-[3-(3-Chlor-2-fluorphenoxy)-6-methylpyridazin-4-yl]-5-(2-chlor-4-methylbenzyl)-5,6-dihydro-4H-l,2,4-oxadiazin, (15.088) 6-Chlor-3-(3-cyclopropyl-2-fluorphenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluorethyl]-5-methylpyridazin-4-carboxamid, (15.089) 3-(3-Brom-2-fluor-phenoxy)-6-chlor-N-[2-(2-chlor-4-methylphenyl)-2,2-difluorethyl]-5-methylpyridazin-4-carboxamid, (15.090) 6-Chlor-N-[2-(2-chlor-4-methylphenyl)-2,2-difluorethyl]-3-(3-cyclopropyl-2-fluorphenoxy)-5-methylpyridazin-4-carboxamid, (15.091) 6-Chlor-3-(3-cyclopropyl-2-fluorphenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluorethyl]-5-methylpyridazin-4-carboxamid, (15.092) 6-Chlor-3-(3-chlor-2-fluorphenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluorethyl]-5-methylpyridazin-4-carboxamid, (15.093) N-[2-(2-Brom-4-methylphenyl)-2,2-difluorethyl]-6-chlor-3-(3-cyclopropyl-2-fluorphenoxy)-5-methylpyridazin-4-carboxamid, (15.094) l,l-Diethyl-3-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-hamstoff, (15.095) l,3-Dimethoxy-l-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-hamstoff, (15.096) l-[[3-Fluor-4-(5-(trifluormethyl)-l,2,4-oxadiazol-3-yl)phenyl]methyl]azepan-2-on, (15.097) l-[[4-[5-(Trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-on, (15.098) 1-Methoxy- 1 -methyl-3-[[4-[5-(trifluormethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]hamstoff, (15.099) 1 -Methoxy-3 -methyl- 1 -[[4-[5-(trifluormethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]hamstoff, (15.100) 2-(Difluormethyl)-5 - [2 - [ 1 -(2,6-difluorphenyl)cyclopropoxy]pyrimidin-5 -yl] - 1 ,3 ,4-oxadiazol, (15.101) 2,2-Difluor-N-methyl-2-[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]acetamid, (15.102) 3,3- Dimethyl-l-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-on, (15.103) 3- Ethyl- 1 -methoxy- 1 -[ [4 - [ 5 -(trifluormethyl)- 1 ,2,4-oxadiazol-3 -yl]phenyl]methyl]hamstoff, (15.104) 4,4-Dimethyl-l-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-on, (15.105) 4,4-Dimethyl-2-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-on, (15.106) Dimethylcarbamidsäure-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenylester, (15.107) 5,5-Dimethyl-2-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-on, (15.108) 5-[5- (Difluormethyl)-l,3,4-oxadiazol-2-yl]-N-[(lR)-l-(2,6-difluorphenyl)ethyl]pyrimidin-2-amin, (15.109) 5-[5-(Difluormethyl)-l,3,4-oxadiazol-2-yl]-N-[(lR)-l-(2,6-difluorphenyl)propyl]pyrimidin-2-amin, (15.110) 5 -[5 -(Difluormethyl)- 1 ,3 ,4-oxadiazol-2-yl] -N-[( 1 R)- 1 -(2-fluorphenyl)ethyl]pyrimidin-2-amin, (15.111) 5-[5-(Difluormethyl)-l,3,4-oxadiazol-2-yl]-N-[(lR)-l-(2-fluorphenyl)ethyl]pyrimidin-2-amin, (15.112) 5-[5-(Difluormethyl)-l,3,4-oxadiazol-2-yl]-N-[(lR)-l-(3,5-difluorphenyl)ethyl]pyrimidin-2-amin, (15.113) 5-[5-(Difluormethyl)-l,3,4-oxadiazol-2-yl]-N-[(lR)-l-phenylethyl]pyrimidin-2-amin, (15.114) 5-[5-(Difluormethyl)-l,3,4-oxadiazol-2-yl]-N-[l-(2-fluorphenyl)cyclopropyl]pyrimidin-2-amin, (15.115) 5-Methyl-l-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-on, (15.116) 1 -{4-[5-(Trifluormethyl)- 1 ,2,4-oxadiazol-3-yl]benzyl} - lH-pyrazol-4-carbonsäureethylester, (15.117) {4-[5-Trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl}carbamidsäuremethylester, (15.118) N-(l- Methylcyclopropyl)-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.119) N-(2,4- Difluorphenyl)-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.120) N-(2-Dimethoxy)-N-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamid, (15.121) N,N-Dimethyl-l-{4-[5-BYC240191 Ausland.

[0269] -44 - (trifluormethyl)-l,2,4-oxadiazol-3-yl]benzyl}-lH-l,2,4-triazol-3-amin, (15.122) N-[(E)- Methoxyiminomethyl]-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.123) N-[(E)-N- Methoxy-C-methylcarbonimidoyl]-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.124) N-[(Z)-Methoxyiminomethyl]-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.125) N-[(Z)-N-Methoxy-C-methylcarbonimidoyl]-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.126) N-[ [2,3 -Difluor-4-[5 -(trifluormethyl)- 1 ,2,4-oxadiazol-3 -yl]phenyl]methyl] -3 ,3 ,3 -trifluorpropanamid, (15.127) N-[[4-[5-(Trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamid, (15.128) N-[4-[5-(Trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]cyclopropancarboxamid, (15.129) N-{2,3-Difluor-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzyl}butanamid, (15.130) N-{4-[5-(Trifluormethyl)-l,2,4-oxadiazol-3-yl]benzyl}cyclopropancarboxamid, (15.131) N-{4-[5-(Trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl}propanamid, (15.132) N-Allyl-N-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]-methyl]acetamid, (15.133) N-Allyl-N-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-propanamid, (15.134) N-Ethyl-2-methyl-N-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-propanamid, (15.135) N-Methoxy-N-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-cyclopropancarboxamid, (15.136) N-Methyl-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.137) N-Methyl-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzolcarbothioamid, (15.138) N-Methyl-N-phenyl-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.139) 2,2-Difluor-2-[4-[5- (trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]essigsäure, (15.140) l-[[4-[(Z)-2-Ethoxy-3,3,3-trifluor-prop-l-enoxy]phenyl]methyl]pyrazol-4-carbonsäureethylester, (15.141) l-[[4-[[2-(Trifluormethyl)-l,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazol-4- carbonsäureethylester, (15.142) N-(2,2,2- Trifluorethyl)-2-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]oxazol-4-carboxamid, (15.143) N-[(2S)-l-{3-[(2RS)-2-(5-Fluor-2-methoxyphenyl)-2-hydroxyethyl]-5-[(lE)-N-isopropoxyethanimidoyl]-2,6-dioxo-3,6-dihydropyrimidin-l(2H)-yl}propan-2-yl]-2-methylpropanamid, (15.144) N-[(2S)-l-{3-[2-(5-Fluor-2-methoxyphenyl)-2-hydroxyethyl]-5-[(lE)-N-isopropoxyethanimidoyl] -2,6-dioxo-3 ,6-dihydropyrimidin- 1 (2H)-yl} -3 -methylbutan-2-yl] -2-methylpropanamid, (15.145) N-[(2S)-l-{3-[2-(5-Fluor-2-methoxyphenyl)-2-hydroxyethyl]-5-[(lE)-N-isopropoxyethanimidoyl] -2, 6-dioxo-3 ,6-dihydropyrimidin- 1 (2H)-yl} -3 -methylbutan-2-yl] -2,2-dimethylpropanamid, (15.146) N-[(2S)-l-{3-[2-Hydroxy-2-(2-methoxyphenyl)ethyl]-5-[(lE)-N-isopropoxyethanimidoyl]-2,6-dioxo-3,6-dihydropyrimidin-l(2H)-yl}propan-2-yl]-2-methylpropanamid, (15.(147) N-[(2S)-l-{3-[(2R)-2-(5 -Fluoro-2 -methoxyphenyl) -2 -hydroxy ethyl] -5 - [( 1 E)-N-isopropoxyethanimidoyl]-2,6-dioxo-3,6-dihydropyrimidin-l(2H)-yl}propan-2-yl]-2-methylpropanamide, (15.149) N-[(2S)-l-{3-[(2R)-2-(5-Fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(lE)-N-isopropoxyethanimidoyl] -2, 6-dioxo-3,6-dihydropyrimidin-1(2H)-yl} -3 -methylbutan-2-yl] -2 -methylpropanamide.BYC240191 Abroad.

[0270] - 45 - Biological pesticides as mixture components

[0271] The compounds of formula (I) can be combined with biological pesticides.

[0272] Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and products formed by microorganisms, including proteins and secondary metabolites.

[0273] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria, and bacteria that act as biological insecticides, fungicides, or nematicides.

[0274] Examples of such bacteria that are used or can be used as biological pesticides are:

[0275] Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (accession number CNCM 1-1582) or Bacillus pumilus. in particular strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, in particular strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or 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), Methylorubrum extorquens TS201, 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).

[0276] Examples of fungi and yeasts that are used or can be used as biological pesticides include:

[0277] Beauveria bassiana, in particular strain ATCC 74040, Coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., in particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metchnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (formerly Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89 / 030550), Talaromyces flavus, especially strain VI 17b, Trichoderma atroviride, especially strain SCI (Accession Number CBS 122089), Trichoderma harzianum, especially T. harzianum rifai T39 (Accession Number CNCM 1-952). BYC240191 Abroad

[0278] - 46 - Examples of viruses that are used or can be used as biological pesticides are:

[0279] Adoxophyes orana (apple peel moth) granulovirus (GV), Cydia pomonella (cobble moth) granulovirus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet moth) mNPV, Spodoptera frugiperda (army worm) mNPV, Spodoptera littoralis (African cotton bollworm) NPV.

[0280] This also includes bacteria and fungi that are added to plants, plant parts, or plant organs as 'inoculators' and promote plant growth and health through their special properties. Examples include:

[0281] Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especially Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.

[0282] Examples of plant extracts and products formed by microorganisms, including proteins and secondary metabolites, that are or can be used as biological pesticides are:

[0283] Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, “Requiem ™ Insecticide”, Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen extract, especially rapeseed or mustard powder, as well as bioinsecticides obtained from olive oil / acaricidal active ingredients, especially unsaturated ones Fatty / carboxylic acids with carbon chain lengths of C16-C20 as active ingredients, such as those contained in the product with the trade name FLiPPER®.

[0284] Safeners as mixing components

[0285] The compounds of formula (I) can be combined with safeners, such as benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormide, fenchlorazole (-ethyl), fenclorim, flurazol, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-l-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[0286] Plants and plant parts BYC240191 Abroad

[0287] - 47 - According to the invention, all plants and plant parts can be treated. The term "plants" here refers to all plants and plant parts, 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, peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans, Brassica oleracea (e.g., cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes).Cultivated plants can be plants that can be obtained through conventional breeding and optimization methods, or through biotechnological and genetic engineering methods, or combinations thereof, including transgenic plants and plant varieties that are or are not protected by plant variety rights. The term "plant" encompasses all stages of development, from seeds and cuttings to young (immature) plants and mature plants. "Plant parts" refers to all above-ground and below-ground parts and organs of plants, such as shoots, leaves, flowers, and roots, with examples including leaves, needles, stems, trunks, flowers, fruiting bodies, fruits, and seeds, as well as roots, tubers, and rhizomes.Plant parts also include harvested plants or harvested plant parts, as well as vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.

[0288] The treatment of plants and plant parts with the compounds of formula (I) according to the invention is carried out directly or by the action of the compounds on the environment, the habitat or the storage area according to the usual treatment methods, e.g. by immersion, spraying, evaporation, fogging, scattering, brushing, injection and, in the case of propagation material, especially seeds, furthermore by single or multi-layer coating.

[0289] As mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild-occurring plant species and varieties, as well as those obtained through conventional biological breeding methods such as hybridization or protoplast fusion, are treated. In another preferred embodiment, transgenic plants and varieties obtained through genetic engineering, optionally in combination with conventional methods (genetically modified organisms), and their parts are treated. The terms "parts" or "parts of plants" or "plant parts" have been explained above. Plants of commercially available or currently used varieties are particularly preferred according to the invention. Plant varieties are understood to be plants with new traits obtained through conventional breeding, mutagenesis, or recombinant DNA techniques.These can be varieties, breeds, biotypes and genotypes.

[0290] Transgenic plant, seed treatment and integration events

[0291] According to the invention, the compounds of formula (I) can be advantageously used to treat transgenic plants, plant cultivars or plant parts which contain genetic material. BYC240191 Abroad

[0292] - 48 -have, which confers advantageous and / or useful properties (traits) on these plants, plant cultivars, or plant parts. It is therefore considered to combine the present invention with one or more recombinant traits or transgenic events, or a combination thereof. For the purposes of the present application, a transgenic event occurs through the insertion of a specific recombinant DNA molecule into a specific position (locus) in the chromosome of the plant genome. The insertion creates a new DNA sequence, which is referred to as an "event" and is characterized by the inserted recombinant DNA molecule and a certain amount of genomic DNA immediately adjacent to the inserted DNA / flanking the inserted DNA at both ends. Such traits orTransgenic events include, but are not limited to, resistance to pests, water use efficiency, yield performance, drought tolerance, seed quality, improved nutrient quality, hybrid seed production and herbicide tolerance, with the trait being measured in relation to a plant lacking such a trait or transgenic event.Specific examples of such advantageous and / or useful traits include improved plant growth, vigor, stress tolerance, stability, resistance to lodging, nutrient uptake, plant nutrition and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salinity, increased flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and / or higher nutritional value of the harvested products, better shelf life and / or workability of the harvested products and increased resistance or tolerance to animal and microbial pests such as insects, arachnids, nematodes, mites and slugs.

[0293] Of the DNA sequences encoding proteins that confer resistance or tolerance properties to such animal and microbial pests, especially insects, the genetic material of Bacillus thuringiensis, which encodes the Bt proteins, should be mentioned in detail. These proteins are extensively described in the literature and well known to those skilled in the art. Also worth mentioning are proteins extracted from bacteria such as Photorhabdus (WO97 / 17432 and WO98 / 08932). In particular, mention should be made of Bt-Cry or VIP proteins, including CrylA, CrylAb, CrylAc, CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF proteins or toxic fragments thereof, and also hybrids or combinations thereof, especially the CrylF protein or hybrids derived from a CrylF protein (e.g.Hybrid CrylA-CrylF proteins or toxic fragments thereof), the CrylA-type proteins or toxic fragments thereof, preferably the CrylAc protein or hybrids derived from the CrylAc protein (e.g., hybrid CrylAb-CrylAc proteins), or the CrylAb or Bt2 protein or toxic fragments thereof, the Cry2Ae, Cry2Af, or Cry2Ag proteins or toxic fragments thereof, the Cry1A.105 protein or a toxic fragment thereof, the VIP3Aal9 protein, the VIP3Aa20 protein, the VIP3A proteins produced at the COT202 or COT203 cotton events, the VIP3Aa protein or a toxic fragment thereof, as described in Estruch et al. (1996), Proc Natl Acad Sei US A. 28;93(11):5389-94, which described the Cry proteins as described in WO2001 / 47952, the insecticidal proteins from Xenorhabdus (as in BYC240191 Abroad).

[0294] - 49 - WO98 / 50427 described), Serratia (especially from .S' entomophila) or strands of the Photorhabdus species, such as Tc proteins from Photorhabdus, as described in WO98 / 08932. This also includes any variants or mutants of any of these proteins that differ in some amino acids (1-10, preferably 1-5) from any of the sequences listed above, especially the sequence of their toxic fragment, or that are fused to a transit peptide such as a plastid transit peptide or any other protein or peptide.

[0295] Another, and particularly noteworthy, example of such properties is conferred tolerance to one or more herbicides, for example, imidazolinones, sulfonylhams, glyphosate, or phospinothricin. Of the DNA sequences encoding proteins that confer tolerance to specific herbicides in transformed plant cells and plants, particular mention should be made of the bar or PAT gene, or the Streptomyces coelicolor gene described in WO2009 / 152359, which confers tolerance to glufonsin herbicides; a gene encoding a suitable EPSPS (5-enolpyruvylshikimate-3-phosphate synthase), which confers tolerance to herbicides targeting EPSPS, especially herbicides such as glyphosate and its salts; a gene encoding glyphosate N-acetyltransferase; or a gene encoding glyphosate oxoreductase.Other suitable herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g., W02007 / 024782), a mutated Arabidopsis ALS / AHAS gene (e.g., US Patent 6,855,533), genes encoding 2,4-D monooxygenases that confer tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid), and genes encoding dicamba monooxygenases that confer tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid).

[0296] Other and particularly highlighted examples of such properties are increased resistance to phytopathogenic fungi, bacteria and / or viruses, which is due, for example, to systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and the correspondingly expressed proteins and toxins.

[0297] Particularly useful transgenic events in transgenic plants or plant cultivars that can preferably be treated according to the invention include Event 531 / PV-GHBK04 (cotton, insect control, described in W02002 / 040677); Event 1143-14A (cotton, insect control, not filed, described in WO2006 / 128569); Event 1143-51B (cotton, insect control, not filed, described in W02006 / 128570); Event 1445 (cotton, herbicide tolerance, not filed, described in US-A 2002-120964 or W02002 / 034946); Event 17053 (rice, herbicide tolerance, filed as PTA-9843, described in WO2010 / 117737). Event 17314 (Rice, herbicide tolerance, filed as PTA-9844, described in WO2010 / 117735); Event 281-24-236 (Cotton, insect control - herbicide tolerance, filed as PTA-6233, described in W02005 / 103266 or US-A 2005-216969);Event 3006-210-23 (Cotton, Insect Control - Herbicide Tolerance, filed as PTA-6233, described in US-A 2007-143876 or W02005 / 103266); Event 3272 (Corn, Quality Trait, filed as PTA-9972, described in W02006 / 098952 or US-BYC240191 Abroad;

[0298] - 50 - A 2006-230473); Event 33391 (Wheat, herbicide tolerance, filed as PTA-2347, described in W02002 / 027004), Event 40416 (Maize, insect control - herbicide tolerance, filed as ATCC PTA-11508, described in WO 11 / 075593); Event 43A47 (Maize, insect control - herbicide tolerance, filed as ATCC PTA-11509, described in WO2011 / 075595); Event 5307 (Maize, insect control, filed as ATCC PTA-9561, described in W02010 / 077816); Event ASR-368 (Bentgrass, herbicide tolerance, filed as ATCC PTA-4816, described in US-A 2006-162007 or W02004 / 053062); Event B16 (Corn, herbicide tolerance, not filed, described in US-A 2003-126634); Event BPS-CV127-9 (Soybean, herbicide tolerance, filed as NCIMB No. 41603, described in WO2010 / 080829);Event BLR1 (Canola, restoration of pollen sterility, filed as NCIMB 41193, described in W02005 / 074671); Event CE43-67B (Cotton, insect control, filed as DSM ACC2724, described in US-A 2009-217423 or WO2006 / 128573); Event CE44-69D (Cotton, insect control, not filed, described in US-A 2010-0024077); Event CE44-69D (Cotton, insect control, not filed, described in WO2006 / 128571); Event CE46-02A (Cotton, insect control, not filed, described in WO2006 / 128572); Event COT102 (Cotton, Insect Control, not filed, described in US-A 2006-130175 or W02004 / 039986); Event COT202 (Cotton, Insect Control, not filed, described in US-A 2007-067868 or W02005 / 054479); Event COT203 (Cotton, Insect Control, not filed, described in W02005 / 054480); );Event DAS21606-3 / 1606 (soybean, herbicide tolerance, filed as PTA-11028, described in WO2012 / 033794), Event DAS40278 (maize, herbicide tolerance, filed as ATCC PTA-10244, described in WO2011 / 022469); Event DAS-44406-6 / pDAB8264.44.06.1 (Soybean, herbicide tolerance, filed as PTA-11336, described in WO2012 / 075426), Event DAS-14536-7 / pDAB8291.45.36.2 (Soybean, herbicide tolerance, filed as PTA-11335, described in WO2012 / 075429), Event DAS-59122-7 (Corn, insect control - herbicide tolerance, filed as ATCC PTA 11384, described in US-A 2006-070139); Event DAS-59132 (Corn, insect control - herbicide tolerance, not filed, described in W02009 / 100188); Event DAS68416 (soybean, herbicide tolerance, filed as ATCC PTA-10442, described in WO2011 / 066384 or WO2011 / 066360); Event DP-098140-6 (corn, herbicide tolerance, filed as ATCC PTA-8296, described in US-A 2009-137395 or WO 08 / 112019);Event DP-305423-1 (Soybean, quality trait, not filed, described in US-A 2008-312082 or W02008 / 054747); Event DP-32138-1 (Corn, hybridization system, filed as ATCC PTA-9158, described in US-A 2009-0210970 or W02009 / 103049); Event DP-356043-5 (Soybean, herbicide tolerance, filed as ATCC PTA-8287, described in US-A 2010-0184079 or W02008 / 002872); Event EE-I (Eggplant, insect control, not filed, described in WO 07 / 091277); Event Fil 17 (Corn, herbicide tolerance, filed as ATCC 209031, described in US-A 2006-059581 or WO 98 / 044140); Event FG72 (Soybean, herbicide tolerance, filed as PTA-11041, described in WO2011 / 063413); Event GA21 (Corn, herbicide tolerance, filed as ATCC 209033, described in US-A 2005-086719 or WO 98 / 044140); Event GG25 (Corn, herbicide tolerance, filed as ATCC 209032, described in US-A 2005-188434 or WO98 / 044140); Event GHB119 (Cotton, BYC240191, foreign).

[0299] - 51 - Insect control - Herbicide tolerance, filed as ATCC PTA-8398, described in W02008 / 151780); Event GHB614 (Cotton, herbicide tolerance, filed as ATCC PTA-6878, described in US-A 2010-050282 or W02007 / 017186); Event GJ11 (Corn, herbicide tolerance, filed as ATCC 209030, described in US-A 2005-188434 or W098 / 044140); Event GM RZ13 (Sugar beet, virus resistance, filed as NCIMB-41601, described in W02010 / 076212); Event H7-1 (sugar beet, herbicide tolerance, filed as NCIMB 41158 or NCIMB 41159, described in US-A 2004-172669 or WO 2004 / 074492); Event JOPLIN1 (wheat, disease tolerance, not filed, described in US-A 2008-064032); Event LL27 (soybean, herbicide tolerance, filed as NCIMB41658, described in W02006 / 108674 or US-A 2008-320616); Event LL55 (soybean, herbicide tolerance, filed as NCIMB 41660, described in WO 2006 / 108675 or US-A 2008-196127);Event LLcotton25 (cotton, herbicide tolerance, filed as ATCC PTA-3343, described in W02003 / 013224 or US-A 2003-097687); Event LLRICE06 (rice, herbicide tolerance, filed as ATCC 203353, described in US 6,468,747 or W02000 / 026345); Event LLRice62 (rice, herbicide tolerance, filed as ATCC 203352, described in W02000 / 026345); Event LLRICE601 (rice, herbicide tolerance, filed as ATCC PTA-2600, described in US-A 2008-2289060 or W02000 / 026356); Event LY038 (Corn, quality characteristic, filed as ATCC PTA-5623, described in US-A 2007-028322 or W02005 / 061720); Event MIR162 (Corn, insect control, filed as PTA-8166, described in US-A 2009-300784 or W02007 / 142840); Event MIR604 (Corn, insect control, not filed, described in US-A 2008-167456 or W02005 / 103301); Event MON15985 (Cotton, insect control, filed as ATCC PTA-2516, described in US-A 2004-250317 or W02002 / 100163);Event MON810 (Corn, Insect Control, not filed, described in US-A 2002-102582); Event MON863 (Corn, Insect Control, filed as ATCC PTA-2605, described in W02004 / 011601 or US-A 2006-095986); Event MON87427 (Corn, Pollination Control, filed as ATCC PTA-7899, described in WO2011 / 062904); Event MON87460 (Corn, Stress Tolerance, filed as ATCC PTA-8910, described in W02009 / 111263 or US-A 2011-0138504); Event MON87701 (Soybean, insect control, filed as ATCC PTA-8194, described in US-A 2009-130071 or W02009 / 064652); Event MON87705 (Soybean, quality trait - herbicide tolerance, filed as ATCC PTA-9241, described in US-A 2010-0080887 or W02010 / 037016); Event MON87708 (Soybean, herbicide tolerance, filed as ATCC PTA-9670, described in WO2011 / 034704);Event MON87712 (Soybean, yield, filed as PTA-10296, described in WO2012 / 051199); Event MON87754 (Soybean, quality trait, filed as ATCC PTA-9385, described in WO2010 / 024976); Event MON87769 (Soybean, quality trait, filed as ATCC PTA-8911, described in US-A 2011-0067141 or W02009 / 102873); Event MON88017 (Corn, insect control - herbicide tolerance, filed as ATCC PTA-5582, described in US-A 2008-028482 or W02005 / 059103); Event MON88913 (Cotton, herbicide tolerance, filed as ATCC PTA-4854, described in W02004 / 072235 or US-A 2006-059590); Event MON88302 (Canola, herbicide tolerance, filed as PTA-10955, described in WO2011 / 153186); Event MON88701 (Cotton, herbicide tolerance, filed as PTA-11754, described in WO2012 / 134808); BYC240191 Foreign;

[0300] - 52 - Event MON89034 (Corn, insect control, filed as ATCC PTA-7455, described in WO 07 / 140256 or US-A 2008-260932); Event MON89788 (Soybean, herbicide tolerance, filed as ATCC PTA-6708, described in US-A 2006-282915 or W02006 / 130436); Event MSI 1 (Canola, pollination control - herbicide tolerance, filed as ATCC PTA-850 or PTA-2485, described in W02001 / 031042); Event MS8 (Canola, pollination control - herbicide tolerance, filed as ATCC PTA-730, described in W02001 / 041558 or US-A 2003-188347); Event NK603 (Corn, herbicide tolerance, filed as ATCC PTA-2478, described in US-A 2007-292854); Event PE-7 (Rice, insect control, not filed, described in W02008 / 114282); Event RF3 (Canola, pollination control - herbicide tolerance, filed as ATCC PTA-730, described in WO2001 / 041558 or US-A 2003-188347); Event RT73 (Canola, herbicide tolerance, not filed)described in W02002 / 036831 or US-A 2008-070260); Event SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerance, filed as PTA-11226, described in WO2012 / 082548), Event T227-1 (sugar beet, herbicide tolerance, not filed, described in W02002 / 44407 or US-A 2009-265817); Event T25 (corn, herbicide tolerance, not filed, described in US-A 2001-029014 or W02001 / 051654); Event T304-40 (Cotton, Insect Control - Herbicide Tolerance, filed as ATCC PTA-8171, described in US-A 2010-077501 or W02008 / 122406); Event T342-142 (Cotton, Insect Control, not filed, described in WO2006 / 128568); Event TC1507 (Corn, Insect Control - Herbicide Tolerance, not filed, described in US-A 2005-039226 or W02004 / 099447); Event VIP1034 (Corn, Insect Control - Herbicide Tolerance, filed as ATCC PTA-3925, described in W02003 / 052073); Event 32316 (Corn, Insect Control - Herbicide Tolerance, filed as PTA-11507, described in WO2011 / 084632).Event 4114 (Maize, insect control herbicide tolerance, filed as PTA-11506, described in W02011 / 084621), Event EE-GM3 / FG72 (Soybean, herbicide tolerance, ATCC access no. PTA-11041) possibly stacked with Event EE-GM1 / LL27 or Event EE-GM2 / LL55 (WO2011 / 063413 A2), Event DAS-68416-4 (Soybean, herbicide tolerance, ATCC access no. PTA-10442, WO2011 / 066360A1), Event DAS-68416-4 (Soybean, herbicide tolerance, ATCC access no. PTA-10442, WO2011 / 066384A1), Event DP-040416-8 (Maize, insect control, ATCC access no. PTA-11508, WO2011 / 075593A1), Event DP-043A47-3 (Maize, insect control, ATCC access no. PTA-11509, WO2011 / 075595A1), Event DP-004114-3 (Maize, insect control, ATCC access no. PTA-11506, WO2011 / 084621A1), Event DP-032316-8 (Maize, insect control, ATCC access no. PTA-11507, WO2011 / 084632A1), Event MON-88302-9 (Rapeseed oilseed, herbicide tolerance, ATCC access no. PTA-10955, WO2011 / 153186A1), Event DAS-21606-3 (Soybean, Herbicide Tolerance, ATCC Access No. PTA-11028,WO2012 / 033794A2), Event MON-87712-4 (Soybean, quality trait, ATCC access no. PTA-10296, WO2012 / 051199A2), Event DAS-44406-6 (Soybean, stacked herbicide tolerance, ATCC access no. PTA-11336, WO2012 / 075426A1), Event DAS-14536-7 (Soybean, stacked herbicide tolerance, ATCC access no. PTA-11335, WO2012 / 075429A1), Event SYN-000H2-5 (Soybean, herbicide tolerance, ATCC access no. PTA-11226, WO2012 / 082548A2), Event DP-061061-7 (Rapeseed rape, herbicide tolerance, no deposit number available, W02012071039A1), Event DP-073496-4 (Rapeseed rape, herbicide tolerance, no deposit number BYC240191, foreign)

[0301] - 53 - available, US2012131692), Event 8264.44.06.1 (Soybean, stacked herbicide tolerance, Access No. PTA-11336, WO2012075426A2), Event 8291.45.36.2 (Soybean, stacked herbicide tolerance, Access No. PTA-11335, WO2012075429A2), Event SYHT0H2 (Soybean, ATCC Access No. PTA-11226, WO2012 / 082548A2), Event MON88701 (Cotton, ATCC Access No. PTA-11754, WO2012 / 134808A1), Event KK179-2 (Alfalfa, ATCC accession number PTA-11833, W02013 / 003558A1), Event pDAB8264.42.32.1 (soybean, stacked herbicide tolerance, ATCC accession number PTA-11993, W02013 / 010094A1), Event MZDT09Y (corn, ATCC accession number PTA-13025, WO2013 / 012775A1). Furthermore, such a list of transgenic events is provided by the United States Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website at https: / / www.aphis.usda.gov / . For the present application, the status of this list as it existed on the filing date of the present application is relevant.

[0302] The genes / events that confer the desired traits can also occur in combination with one another in transgenic plants. Examples of transgenic plants that can be mentioned include important crops such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peas and other types of vegetables, cotton, tobacco, rapeseed, and also fruit plants (including apples, pears, citrus fruits, and grapes), with maize, soybeans, wheat, rice, potatoes, cotton, sugarcane, tobacco, and rapeseed being particularly noteworthy. Traits that are particularly emphasized are the plants' increased resistance to insects, arachnids, nematodes, and slugs, as well as the plants' increased resistance to one or more herbicides.

[0303] Commercially available examples of such plants, plant parts, or plant seeds that can preferably be treated according to the invention include commercially available products such as plant seeds that fall under the GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY®, VT DOUBLE PRO®, VT TRIPLE PRO®, BOLLGARD II®, ROUNDUP READY 2 YIELD®, YIELDGARD®, and ROUNDUP READY® 2 XTEN categories. DTM -, INTACTA RR2 PRO®, VISTIVE GOLD® and / or XTENDFLEX™ trade names are sold or distributed.

[0304] Plant protection - Treatment methods

[0305] The treatment of plants and plant parts with the compounds of formula (I) is carried out directly or by acting upon their environment, habitat, or storage area according to usual treatment methods, e.g., by dipping, spraying, misting, evaporation, atomization, fogging, scattering, foaming, brushing, spreading, injecting, drenching, drip irrigation, and, in the case of propagation material, especially seeds, furthermore by dry dressing, wet dressing, slurry dressing, incrustation, single- or multi-layer coating, etc. It is also possible to apply the compounds of formula (I) using the ultra-low-volume method or to inject the application form or the compound of formula (I) itself into the soil. BYC240191 Abroad

[0306] - 54 - A preferred direct treatment of the plants is foliar application, i.e. the compounds of formula (I) are applied to the foliage, whereby the treatment frequency and the application rate should be adjusted to the infestation pressure of the respective pest.

[0307] In the case of systemically acting active ingredients, 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 plant's location (e.g., soil or hydroponic systems) is saturated with a liquid form of the compounds of formula (I), or by soil application, i.e., the compounds of formula (I) according to the invention are introduced into the plant's location in solid form (e.g., in the form of granules), or by drip application (often also referred to as "chemigation"), i.e., the compounds of formula (I) according to the invention are introduced at defined locations near the plants over specific periods of time, together with varying amounts of water, using surface or subsurface drip lines.In the case of aquatic rice cultures, this can also be achieved by adding the compound of formula (I) in a solid application form (e.g. as granules) to a flooded rice field.

[0308] Digital technologies

[0309] The compounds according to the invention can be used in combination with, for example, models embedded in computer programs for site-specific crop management, satellite agriculture, precision agriculture, or precision farming. Such models support the site-specific management of agricultural assets with data from various sources such as soils, weather, crops (e.g., type, growth stage, plant health), weeds (e.g., type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield, etc., with the aim of optimizing profitability, sustainability, and environmental protection. In particular, such models can help to optimize agronomic decisions, control the precision of pesticide applications, and record the work performed.

[0310] For example, the compounds according to the invention can be applied to a crop plant according to a corresponding application protocol if the model modulates the occurrence of a pest and calculates that a threshold has been reached at which it is recommended to apply the compound according to the invention to the crop plant.

[0311] Commercially available systems that include agronomic models include, for example, FieldScripts™ from The Climate Corporation, Xarvio™ from BASF, AGLogic™ from John Deere, etc. BYC240191 Abroad

[0312] - 55 - The compounds according to the invention can also be used in combination with smart spraying equipment, such as spot spraying or precision spraying equipment, which is attached to or housed on a farm vehicle such as a tractor, robot, helicopter, airplane, or unmanned aerial vehicle (UAV) such as a drone. Such equipment usually includes input sensors (such as a camera) and a processing unit configured to analyze the input data and provide a decision, based on the analysis of the input data, for applying the compound according to the invention to the crops (or weeds) in a specific and precise manner. The use of such smart spraying equipment usually requires positioning systems (e.g., GPS receivers) with which the recorded data can be located and the farm vehicle controlled.Controlled geographic information systems (GIS) that display the information on understandable maps, and appropriate farm vehicles to carry out the necessary agricultural measures such as spraying.

[0313] In one example, pests can be detected from images captured by a camera. In another example, the pests can be identified and / or classified based on these images. Such identification and / or classification can utilize image processing algorithms. These image processing algorithms can employ machine learning algorithms such as artificial neural networks, decision trees, and artificial intelligence algorithms. In this way, it is possible to apply the connections described here only where they are needed.

[0314] Seed treatment

[0315] Controlling animal pests by treating plant seeds has long been known and is subject to continuous improvement. Nevertheless, seed treatment presents a number of problems that cannot always be satisfactorily resolved. It is therefore desirable to develop methods for protecting seeds and germinating plants that eliminate or at least significantly reduce the need for additional application of pesticides during storage, after sowing, or after emergence. Furthermore, it is desirable to optimize the amount of active ingredient used so that the seeds and germinating plants are protected as effectively as possible from infestation by animal pests, without harming the plant itself with the active ingredient. In particular, seed treatment methods should also utilize the intrinsic insecticidal properties of the seeds.to incorporate the nematicidal properties of pest-resistant or pest-tolerant transgenic plants in order to achieve optimal protection of the seed and also the germinating plant with a minimal use of pesticides.

[0316] The present invention therefore relates in particular to a method for protecting seeds and germinating plants from infestation by pests, by treating the seeds with one of the BYC240191 foreign

[0317] - 56 - compounds of formula (I). The inventive method for protecting seeds and germinating plants from infestation by pests further comprises a method in which the seeds are treated simultaneously in one process or sequentially with a compound of formula (I) and a mixture component. It also further comprises a method in which the seeds are treated at different times with a compound of formula (I) and a mixture component.

[0318] The invention also relates to the use of the compounds of formula (I) for the treatment of seeds to protect the seeds and the resulting plant from animal pests.

[0319] The invention further relates to seeds treated with a compound of formula (I) according to the invention for protection against animal pests. The invention also relates to seeds treated simultaneously with a compound of formula (I) and a mixture component. The invention further relates to seeds treated at different times with a compound of formula (I) and a mixture component. In the case of seeds treated at different times with a compound of formula (I) and a mixture component, the individual substances may be present in different layers on the seeds. The layers containing a compound of formula (I) and mixture components may optionally be separated by an intermediate layer.The invention also relates to seed in which a compound of formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating.

[0320] 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.

[0321] One of the advantages of a compound of formula (I) acting systemically is that the treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter can be omitted.

[0322] Another advantage is that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.

[0323] It is also considered advantageous that compounds of formula (I) can be used particularly in transgenic seeds.

[0324] Compounds of formula (I) can also be used in combination with compositions or compounds of signaling technology, thereby improving colonization with symbionts, such as BYC240191 abroad

[0325] - 57 - Example rhizobia, mycorrhiza and / or endophytic bacteria or fungi, takes place and / or optimized nitrogen fixation occurs.

[0326] The compounds of formula (I) are suitable for protecting seeds of any plant variety used in agriculture, greenhouses, forestry, or horticulture. This includes, in particular, seeds of cereals (e.g., wheat, barley, rye, millet, and oats), maize, cotton, soybeans, rice, potatoes, sunflowers, coffee, tobacco, canola, rapeseed, beets (e.g., sugar beets and fodder beets), peanuts, vegetables (e.g., tomatoes, cucumbers, beans, brassicas, onions, and lettuce), fruit plants, lawns, and ornamental plants. The treatment of seeds of cereals (such as wheat, barley, rye, and oats), maize, soybeans, cotton, canola, rapeseed, vegetables, and rice is of particular importance.

[0327] As mentioned above, the treatment of transgenic seeds with a compound of formula (I) is also of particular importance. These are seeds of plants that generally contain at least one heterologous gene that controls the expression of a polypeptide with, in particular, insecticidal or nematicidal properties. The heterologous genes in transgenic seeds can originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus, or Gliocladium. The present invention is particularly suitable for the treatment of transgenic seeds that contain at least one heterologous gene originating from Bacillus sp. Preferably, this is a heterologous gene originating from Bacillus thuringiensis.

[0328] In the context of the present invention, the compound of formula (I) is applied to the seed. Preferably, the seed is treated in a state where it is stable enough that no damage occurs during treatment. In general, the seed treatment can be carried out at any time between harvest and sowing. Typically, seed is used that has been separated from the plant and freed from cobs, husks, stems, hulls, wool, or pulp. For example, seed can be used that has been harvested, cleaned, and dried to a suitable moisture content for storage. Alternatively, seed can be used that, after drying, has been treated with water and then dried again, for example, by priming.In the case of rice seed, it is also possible to use seed that has been soaked, for example in water, up to a certain stage of the rice embryo (“Pigeon Breast Stage”), which stimulates germination and a more uniform emergence.

[0329] In general, when treating seeds, care must be taken to ensure that the amount of compound (I) and / or other additives applied to the seeds is chosen so that seed germination is not impaired or the resulting plant is not damaged. This is particularly important to consider with active ingredients that can exhibit phytotoxic effects at certain application rates. BYC240191 Abroad

[0330] - 58 - 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.

[0331] The compounds of formula (I) can be incorporated into the usual seed treatment formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coatings for seeds, as well as ULV formulations.

[0332] These formulations are prepared in a known manner by mixing the compounds of formula (I) with usual additives, such as usual extenders, solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.

[0333] All dyes commonly used for such purposes are suitable as colorants that may be included in the mordant formulations usable according to the invention. Both pigments that are sparingly soluble in water and dyes that are soluble in water can be used. Examples include the dyes known as Rhodamin B, CI Pigment Red 112, and CI Solvent Red 1.

[0334] All substances commonly used in the formulation of agrochemical active ingredients that promote wetting are suitable as wetting agents that may be included in the seed treatment formulations usable according to the invention. Alkylnaphthalenesulfonates, such as diisopropyl or diisobutylnaphthalenesulfonates, are particularly suitable.

[0335] All nonionic, anionic, and cationic dispersants commonly used in the formulation of agrochemical active ingredients are suitable as dispersants and / or emulsifiers that may be included in the seed treatment formulations usable according to the invention. Nonionic or anionic dispersants, or mixtures of nonionic or anionic dispersants, are preferred. 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, lignosulfonates, polyacrylic acid salts, and arylsulfonate-formaldehyde condensates.

[0336] The seed treatment formulations usable according to the invention can contain all foam-inhibiting substances commonly used in the formulation of agrochemical active ingredients as defoamers. Silicone defoamers and magnesium stearate are particularly suitable. BYC240191 Abroad

[0337] - 59 - As preservatives, all substances that can be used for such purposes in agrochemicals can be present in the pickling agent formulations usable according to the invention. Dichlorophene and benzyl alcohol hemiformal are examples.

[0338] Suitable secondary thickening agents that may be included in the seed treatment formulations usable according to the invention are all substances that can be used for such purposes in agrochemicals. Cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays, and highly dispersed silica are particularly preferred.

[0339] Suitable adhesives that may be included in the pickling agent formulations usable according to the invention are all conventional binders that can be used in pickling agents. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and Tylose are particularly preferred.

[0340] The gibberellins that may be included in the seed treatment formulations usable according to the invention are preferably the gibberellins A1, A3 (= gibberellic acid), A4 and A7; gibberellic acid is particularly preferred. The gibberellins are known (see R. Wegler, "Chemistry of Plant Protection and Pest Control Agents", Vol. 2, Springer Verlag, 1970, pp. 401-412).

[0341] The seed treatment formulations usable according to the invention can be used either directly or after prior dilution with water for the treatment of seeds of various kinds. The concentrates or the preparations obtainable from them by dilution with water can be used for the treatment of seeds of cereals such as wheat, barley, rye, oats, and triticale, as well as seeds of maize, rice, rapeseed, peas, beans, cotton, sunflowers, soybeans, and beets, or also of vegetable seeds of various types. The seed treatment formulations usable according to the invention, or their diluted forms, can also be used for the treatment of seeds of transgenic plants.

[0342] For treating seeds with the seed treatment formulations usable according to the invention, or with application forms produced therefrom by adding water, all mixing equipment commonly used for seed treatment is suitable. Specifically, the seed treatment process involves placing the seeds in a mixer operating intermittently or continuously, adding the desired quantity of seed treatment formulations, either as such or after prior dilution with water, and mixing until the formulation is uniformly distributed on the seeds. A drying process may follow.

[0343] The application rate of the seed treatment formulations usable according to the invention can be varied within a wider range. It depends on the respective content of the compounds of formula (I) in the formulations and on the seed. The application rates for compound BYC240191 (for foreign countries)

[0344] - 60 -of formula (I) generally range between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.

[0345] Animal health

[0346] In the field of animal health, i.e., veterinary medicine, the compounds of formula (I) are effective against animal parasites, especially ectoparasites or endoparasites. The term endoparasite includes, in particular, helminths and protozoa such as coccidia. Ectoparasites are typically and preferentially arthropods, especially insects or acarids.

[0347] In the field of veterinary medicine, the compounds of formula (I), which exhibit favorable toxicity towards warm-blooded animals, are suitable for controlling parasites that occur in animal breeding and husbandry in farm animals, breeding animals, zoo animals, laboratory animals, experimental animals and pets. They are effective against all or individual developmental stages of the parasites.

[0348] Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer and especially cattle and pigs; or poultry such as turkeys, ducks, geese and especially chickens; or fish or crustaceans, e.g. in aquaculture, or possibly insects such as bees.

[0349] Pets include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and especially dogs, cats, pet birds; reptiles, amphibians or aquarium fish.

[0350] According to one particular embodiment, the compounds of formula (I) are administered to mammals.

[0351] According to another specific embodiment, the compounds of formula (I) are administered to birds, namely pet birds or, in particular, poultry.

[0352] The use of the compounds of formula (I) for the control of animal parasites is intended to reduce or prevent disease, deaths and reductions in performance (in meat, milk, wool, hides, eggs, honey and the like), thus enabling more economical and simpler animal husbandry and achieving better animal welfare.

[0353] In the context of animal health, the term "control" or "to combat" means that the compounds of formula (I) effectively reduce the occurrence of the respective parasite in an animal infected with such parasites to a harmless degree. More precisely, "to combat" in this context means that the compounds of formula (I) kill the respective parasite, prevent its growth, or prevent its reproduction. BYC240191 Abroad

[0354] - 61 - Arthropods include, but are not limited to,

[0355] from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.;

[0356] from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp.; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Wemeckiella spp.;

[0357] from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Uipoptena spp., Uucilia spp., Uutzomyia spp., Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.;

[0358] from the order Siphonapterida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.;

[0359] from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp.; as well as offshoots and hygiene pests from the order Blattarida.

[0360] Furthermore, the following arthropods are examples, but not limited to:

[0361] From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Omithodorus spp., Otobius spp., from the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genus of multi-host ticks); from the order Mesostigmata, such as Dermanyssus spp., Omithonyssus spp., Pneumonyssus spp., Raillietia spp., Stemostoma spp., Tropilaelaps spp., Varroa spp.; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Demodex spp., Uistrophorus spp., Myobia spp., Neotrombicula spp., Omithocheyletia spp., Psorergates spp., Trombicula spp.; and from the order Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Uaminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp.

[0362] Examples of parasitic protozoa include, but are not limited to:

[0363] Mastigophora (Flage llata), such as: BYC240191 Abroad

[0364] - 62 - Metamonada: from the order Diplomonadida, for example Giardia spp., Spironucleus spp.

[0365] Parabasala: from the order Trichomonadida, for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.

[0366] Euglenozoa: from the order Trypanosomatida, for example Leishmania spp., Trypanosoma spp.

[0367] Sarcomastigophora (Rhizopoda), such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp.

[0368] Alveolata such as Apicomplexa (Sporozoa): e.g., Cryptosporidium spp.; from the order Eimeriida, for example, Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; from the order Adeleida, e.g., Hepatozoon spp., Klossiella spp.; from the order Haemosporida, e.g., Leucocytozoon spp., Plasmodium spp.; from the order Piroplasmida, e.g., Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; from the order Vesibuliferida, e.g., Balantidium spp., Buxtonella spp.

[0369] Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., and also, for example, Myxozoa spp.

[0370] Examples of helminths that are pathogenic to humans or animals include Acanthocephala, nematodes, Pentastoma and platyhelminths (e.g., Monogenea, Cestodes and Trematodes).

[0371] Examples of helminths include, but are not limited to:

[0372] Monogenea: e.g. E.g.: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Poly stoma spp., Troglecephalus spp.;

[0373] Cestodes: from the order Pseudophyllidea, for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp., Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.

[0374] From the order Cyclophyllida, for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.

[0375] Trematodes: from the class Digenea, for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp., Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp., BYC240191 Abroad

[0376] - 63 - Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Omithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.

[0377] Nematodes: from the order Trichinellida, for example: Capillaria spp., Eucoleus spp., Paracapillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.

[0378] From the order Tylenchida, for example: Micronema spp., Parastrangyloides spp., Strongyloides spp.

[0379] Aus der Ordnung Rhabditina zum Beispiel: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.; Omithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp.

[0380] From the order Spirurida, for example: Acanthocheilonema spp., Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp.

[0381] Acanthocephala: from the order Oligacanthorhynchida, e.g.: Macracanthorhynchus spp., Prosthenorchis spp.; from the order Moniliformida, for example: Moniliformis spp.,

[0382] From the order Polymorphida, for example: Filicollis spp.; from the order Echinorhynchida, for example: Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.

[0383] Pentastoma: from the order Porocephalida, for example Linguatula spp. BYC240191 Abroad

[0384] - 64 - Parasites of fish include, for example, crustaceans, which in turn comprise the following families: Caligidae with the exemplary species Dissonus, Caligus (e.g. BC curtus, C. elongatus, C. clemensi, C. rogercresseyii) and Lepeophtheirus (e.g. BL salmonis); the families Cecropidae, Dichelesthiidae, Lemaeopodidae with the exemplary species Salmincola; the families Pandaridae, Pennellidae with the exemplary species Lemaeocera and Pennella; the family Sphyriidae; the family Lemaeidae with the exemplary species Lemaea; the families Bomolochidae, Chondracanthidae, Ergasilidae and Philichthyidae; the family Argulidae with the exemplary species Argulus (e.g. BA foliaceus).

[0385] In the field of veterinary medicine and animal husbandry, the compounds of formula (I) are administered according to generally known procedures, such as enteral, parenteral, dermal, or nasal administration in the form of suitable preparations. Administration can be prophylactic, metaphylactic, or therapeutic.

[0386] One embodiment of the present invention relates to the compounds of formula (I) for use as pharmaceuticals.

[0387] Another aspect relates to the compounds of formula (I) for use as an antiendoparasitic.

[0388] Another special aspect concerns the compounds of formula (I) for use as an anthelmintic, in particular for use as a nematicide, platymelminthicide, acanthocephalicide or pentastomicide.

[0389] Another special aspect concerns the compounds of formula (I) for use as antiprotozoal agents.

[0390] Another aspect concerns the compounds of formula (I) for use as an antiectoparasitic, in particular an arthropodicide, especially an insecticide or an acaricide.

[0391] Further aspects of the invention are veterinary formulations comprising an effective amount of at least one compound of formula (I) and at least one of the following: a pharmaceutically safe excipient (e.g., solid or liquid diluents), a pharmaceutically safe excipient (e.g., surfactants), in particular a pharmaceutically safe excipient and / or an excipient conventionally used in veterinary formulations.

[0392] A related aspect of the invention is a method for producing a veterinary medicinal formulation as described herein, which includes the step of mixing at least one compound of formula (I) with pharmaceutically safe excipients and / or excipients, in particular with BYC240191 Abroad

[0393] - 65 -comprising pharmaceutically safe excipients and / or excipients traditionally used in veterinary formulations.

[0394] Another special aspect of the invention is veterinary medicinal formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoal and arthropodicidal formulations, and especially selected from the group of nematicide, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal formulations, according to the aforementioned aspects, as well as methods for their preparation.

[0395] Another aspect relates to a method for treating a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites mentioned herein, by applying an effective amount of a compound of formula (I) to an animal, in particular a non-human animal, which requires it.

[0396] Another aspect relates to a procedure for treating a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites mentioned herein, by applying a veterinary formulation as defined herein to an animal, in particular a non-human animal, that requires it.

[0397] Another aspect relates to the use of the compounds of formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal.

[0398] In the present context of animal health or veterinary medicine, the term "treatment" includes prophylactic, metaphylactic and therapeutic treatment.

[0399] In a particular embodiment, mixtures of at least one compound of formula (I) with other active substances, in particular with endo- and ectoparasiticides, are provided for the veterinary medical field.

[0400] In the field of animal health, "mixture" does not only mean that two (or more) different active ingredients are formulated in a common formulation and used together, but also refers to products that contain separate formulations for each active ingredient. Accordingly, if more than two active ingredients are to be used, all active ingredients can be formulated in a common formulation or all active ingredients can be formulated separately; mixed forms are also conceivable, in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow for the separate or sequential use of the active ingredients in question. BYC240191 Abroad

[0401] - 66 - The active ingredients specified here by their “Common Name” are known and are described, for example, in the “Pesticide Manual” (see above) or can be researched on the Internet (e.g. http: / / www.alanwood.net / pesticides).

[0402] Examples of ectoparasiticides suitable as mixing partners include, but are not limited to, the insecticides and acaricides listed in detail above. Further usable active ingredients are listed below according to the classification mentioned above, which is based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GAB A-gated chloride channel blockers; (3) sodium channel modulators; (4) competitive modulators of the nicotinic acetylcholine receptor (nAChR); (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) Modulators of chordotonal organs; (10) Mite growth inhibitors; (12) Mitochondrial ATP synthase inhibitors, such as ATP disruptors;(13) Uncouplers of oxidative phosphorylation by disruption of the proton gradient; (14) Blockers of the nicotinic acetylcholine receptor channel; (15) Inhibitors of chitin biosynthesis, type 0; (16) Inhibitors of chitin biosynthesis, type 1; (17) Molting disruptor (especially in Diptera, i.e., true flies); (18) Ecdysone receptor agonists; (19) Octopamine receptor agonists; (21) Mitochondrial complex I electron transport inhibitors; (25) Mitochondrial complex II electron transport inhibitors; (20) Mitochondrial complex III electron transport inhibitors; (22) Voltage-gated sodium channel blockers; (23) Acetyl-CoA carboxylase inhibitors; (28) Ryanodine receptor modulators; (30) allosteric modulators of the GABA-dependent chloride channel; (33) calcium-activated potassium channel KCa2 modulators; (34) mitochondrial complex III electron transport inhibitors (non-Qo binding site).;

[0403] Active substances with unknown or non-specific mechanisms of action, e.g., fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, flutenzin, bromopropylate, cryolite;

[0404] Connections from other classes:

[0405] Butacarb, Dimetilan, Cloethocarb, Phosphocarb, Pirimiphos(-ethyl), Parathion(-ethyl), Methacrifos, Isopropyl-o-salicylate, Trichlorfon, Sulprofos, Propaphos, Sebufos, Pyridathion, Prothoate, Dichlofenthion, Demeton-S-methylsulfone, Isazofos, Cyanofenphos, Dialifos, Carbophenothione, Autathiofos, Aromfenvinfos(-methyl), Azinphos(-ethyl), Chlorpyrifos(-ethyl), Fosmethilan, Iodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensulfothion, Etrimfos; atelocantel;

[0406] Organochlorine compounds, e.g. camphechlorine, lindane, heptachlor;

[0407] Phenylpyrazole, z. B. Acetoprole, Pyrafluprole, Pyriprole, Vaniliprole, Sisapronile;BYC240191 Ausland

[0408] - 67 - Isoxazoline, z. B. Afoxolaner, Esafoxolaner, Fluralaner, Lotilaner, Mivorilaner, Modoflaner, Sarolaner, Umifoxolaner;

[0409] Pyrazolyl -Arylamide, z. B. Nicofluprole, Tigolaner;

[0410] Pyrethroide, z. B. (cis-, trans-)Metofluthrin, Profluthrin, Flufenprox, Flubrocythrinat, Fubfenprox, Fenfluthrin, Protrifenbut, Pyresmethrin, RU15525, Terallethrin, cis-Resmethrin, Heptafluthrin, Bioethanomethrin, Biopermethrin, Fenpyrithrin, cis-Cypermethrin, cis-Permethrin, Clocythrin, Cyhalothrin (lambda-), Chlovaporthrin, oder halogenierte Kohlenwasserstoffverbindungen (HCHs); Neonicotinoide, z. B. Nithiazin;

[0411] Dicloromezotiaz, Triflumezopyrim;

[0412] macrocyclic lactones, e.g. B. Nemadectin, Ivermectin, Latidectin, Moxidectin, Selamectin, Eprinomectin, Doramectin, Emamectin benzoate, Milbemycin oxime;

[0413] triprene, epofenonan, diofenolan;

[0414] Biologicals, hormones or pheromones, for example natural products such as Thuringiensin, Codlemon or Neem components;

[0415] Dinitrophenols, e.g. B. Dinocap, Dinobuton, Binapacryl;

[0416] Benzoyl urea substances, e.g. B. fluazuron, penfluron;

[0417] amidine derivatives, e.g. B. chlormebuform, cymiazole, demiditraz;

[0418] Tetronic or tetramic acid derivatives, e.g. spidoxamate, spirobudiclofen;

[0419] Beehive Varroa acaricides, for example organic acids, e.g. formic acid, oxalic acid.

[0420] Examples of active ingredients from the group of endoparasiticides, as mixing partners, include, but are not limited to, anthelmintic and antiprotozoal agents.

[0421] Antimicrobial agents include, but are not limited to, the following nematicidal, trematicidal and / or cestocidal agents:

[0422] From the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin, milbemycin; BYC240191 Abroad

[0423] - 68 -from the class of benzimidazoles and probezimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flubendazole;

[0424] from the class of depsipeptides, preferably cyclic depsipeptides, in particular 24-membered cyclic depsipeptides, for example: emodepside, PF1022A;

[0425] Examples from the class of tetrahydropyrimidines: morantel, pyrantel, oxantel;

[0426] Examples from the class of imidazothiazoles: butamisole, levamisole, tetramisole;

[0427] from the class of aminophenylamidines, for example: amidantel, deacylated amidantel (dAMD), tribendimidine;

[0428] From the class of aminoacetonitriles, for example: Monepantel;

[0429] Examples from the class of paraherquamides: paraherquamide, derquantel;

[0430] Examples from the class of salicylanides: Tribromsalan, Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamide, Oxyclozanid, Rafoxanid;

[0431] Examples of substituted phenols include: nitroxynil, bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan;

[0432] Examples of organophosphate classes include: Trichlorfon, Naphthalofos, Dichlorvos / DDVP, Crufomat, Coumaphos, Haloxon;

[0433] from the class of piperazinones / quinolines, for example: praziquantel, aparziquantel, epsiprantel;

[0434] Examples from the piperazine class: piperazine, hydroxyzine;

[0435] Examples from the class of tetracyclines: Tetracycline, Chlorotetracycline, Doxycycline, Oxytetracycline, Rolitetracycline;

[0436] from various other classes, for example: Bunamidine, Niridazole, Resorantel, Omphalotin, Oltipraz, Nitroscanate, Nitroxynil, Oxamniquin, Mirasan, Miracil, Lucanthon, Hycanthon, Hetolin, Emetin, Diethylcarbamazine, Dichlorophen, Diamfenetide, Clonazepam, Bephenium, Amoscanate, Clorsulone.

[0437] Antiprotozoal agents, including but not limited to the following:

[0438] Examples from the triazine class: Diclazuril, Ponazuril, Letrazuril, Toltrazuril;

[0439] from the class polyletherionophore, for example: monensin, salinomycin, maduramicin, narasin; BYC240191 Abroad

[0440] - 69 -from the class of macrocyclic lactones, for example: milbemycin, erythromycin;

[0441] from the class of quinolones, for example: enrofloxacin, pradofloxacin;

[0442] From the class of quinines, for example: chloroquine;

[0443] from the pyrimidine class, for example: pyrimethamine;

[0444] Examples from the sulfonamide class: sulfaquinoxaline, trimethoprim, sulfaclocin;

[0445] From the thiamine class, for example: Amprolium;

[0446] From the class of lincosamides, for example: clindamycin;

[0447] from the class of carbanilides, for example: hnidocarb;

[0448] from the class of nitrofurans, for example: Nifurtimox;

[0449] From the class of quinazoline alkaloids, for example: halofuginone;

[0450] from various other classes, for example: oxamniquin, paromomycin;

[0451] from the class of vaccines or antigens from microorganisms, for example: Babesia canis rossi, Meileria tenella, Meileria praecox, Meileia necatrix, Meileia mitis, Meileia maxima, Meileia brunetti, Meileia acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus.

[0452] All the aforementioned mixing partners can also form salts with suitable bases or acids if they are capable of doing so due to their functional groups.

[0453] Vector control

[0454] The compounds of formula (I) can also be used in vector control. A vector within the meaning of the present invention is an arthropod, in particular an insect or arachnid, that is capable of transmitting pathogens such as viruses, worms, protozoa, and bacteria from a reservoir (plant, animal, human, etc.) to a host. The pathogens can be transmitted either mechanically (e.g., trachoma by non-biting flies) or by injection (e.g., malaria parasites by mosquitoes) into a host.

[0455] Examples of vectors and the diseases or pathogens they transmit are:

[0456] 1) Mosquito BYC240191 Abroad

[0457] - 70 - - Anopheles: malaria, filariasis;

[0458] - Culex: Japanese encephalitis, other viral diseases, filariasis, transmission of other worms;

[0459] - Aedes: Yellow fever, dengue fever, other viral diseases, filariasis;

[0460] - Simia: Transmission of worms, especially Onchocerca volvulus;

[0461] - Psychodidae: Transmission of leishmaniasis

[0462] 2) Lice: skin infections, epidemic typhus;

[0463] 3) Fleas: Plague, endemic typhus, tapeworms;

[0464] 4) Flies: Sleeping sickness (trypanosomiasis); cholera, other bacterial diseases;

[0465] 5) Mites: Acariosis, epidemic typhus, rickettsipox, tularemia, Saint Louis encephalitis, tick-borne encephalitis (TBE), Crimean-Congo hemorrhagic fever, Lyme disease;

[0466] 6) Ticks: Lyme diseases such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), babesia (Babesia canis canis), ehrlichiosis.

[0467] Examples of vectors within the meaning of the present invention are insects, for example aphids, flies, cicadas or thrips, which can transmit plant viruses to plants. Other vectors that can transmit plant viruses are spider mites, aphids, beetles and nematodes.

[0468] Further examples of vectors within the meaning of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. BA gambiae, A. arabiensis, A. fimestus, A. dirus (Malaria) and Culex, psychodids such as Phlebotomus, Lutzomyia, lice, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.

[0469] Vector control is also possible if the compounds of formula (I) are resistance-breaking.

[0470] Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors. Thus, a further aspect of the present invention is the use of compounds of formula (I) for vector control, e.g., in agriculture, horticulture, gardens and recreational facilities, as well as in the protection of stored products and materials.

[0471] Protection of technical materials BYC240191 Abroad

[0472] - 71 - 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.

[0473] In this context, "technical materials" refers to non-living materials, such as preferably plastics, adhesives, glues, papers and cardboards, leather, wood, wood-based products, and coatings. The application of the invention for the protection of wood is particularly preferred.

[0474] In another embodiment, the compounds of formula (I) are used together with at least one other insecticide and / or at least one fungicide.

[0475] In another embodiment, the compounds of formula (I) are provided as a ready-to-use pesticide, i.e., they can be applied to the relevant material without further modification. The insecticides or fungicides mentioned above are particularly suitable as additional insecticides or fungicides.

[0476] Surprisingly, it was also found that the compounds of formula (I) can be used to protect objects, especially ship hulls, sieves, nets, structures, quays, and signaling equipment, from fouling when they come into contact with seawater or brackish water. Likewise, the compounds of formula (I) can be used alone or in combination with other active ingredients as antifouling agents.

[0477] Control of animal pests in the hygiene sector

[0478] The compounds of formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene, and stored product protection, especially for controlling insects, arachnids, ticks, and mites found in enclosed spaces such as apartments, factory halls, offices, vehicle cabins, and animal breeding facilities. For controlling these animal pests, the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients. They are preferably used in household insecticide products. The compounds of formula (I) are effective against susceptible and resistant species as well as against all developmental stages.

[0479] 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. BYC240191 Abroad

[0480] - 72 - Applications include, for example, aerosols, non-pressurized sprays (e.g., pump and atomizer sprays), fogging machines, fogging gels, foams, gels, vaporizer products with cellulose or plastic vaporizer plates, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, passive or energy-free vaporization systems, moth papers, moth sachets and moth gels, as granules or dusts, in scatter baits or bait stations. BYC240191 Abroad

[0481] - 73 - Examples

[0482] The following examples of manufacturing and use illustrate the invention without limiting it.

[0483] Analytical methods

[0484] The analytical procedures described below apply to all information in the entire document, unless the specific analytical procedure is described separately at the relevant point in the text.

[0485] Liquid chromatography-mass spectrometry (LC-MS)

[0486] LC-MS acidic

[0487] The determination of [M+H] + The analysis of M by LC-MS under acidic chromatographic conditions was performed using 1 ml of formic acid per liter of acetonitrile and 0.9 ml of formic acid per liter of Millipore water as eluents. A Zorbax Eclipse Plus CI 8 50 mm × 2.1 mm column was used at an oven temperature of 55 °C.

[0488] Instrument:

[0489] Waters Acquity IClass with SQD2 mass spectrometer and FTN sample changer. Linear gradient from 10% acetonitrile to 95% acetonitrile from 0.0 to 1.70 minutes, constant 95% acetonitrile from 1.70 to 2.40 minutes, flow rate 0.85 ml / min.

[0490] Retention time indices

[0491] The retention time indices were determined in all cases according to a homologous series of straight-chain alkane-2-ones with 3 to 16 carbons, with the index of the first alkanone set to 300, that of the last to 1600, and linear interpolation between the values ​​of successive alkanones.

[0492] The logP values ​​were determined in accordance with EC No 440 / 2008, adapted by (EU) 2016 / 266, Annex, method A.24, using HPLC (High Performance Liquid Chromatography) on a phase-reversing column (CI 8). The calibration of the above methods was carried out using straight-chain alkan-2-ones (with 3 to 16 carbon atoms) with known logP values. The values ​​between successive alkanones are determined by linear regression. The calibration is regularly checked using 7 test substances with known logP values ​​in the range between 0.7 and 4.3. BYC240191 Abroad

[0493] - 74 - Nuclear magnetic resonance spectroscopy (NMR spectroscopy)

[0494] The ¹H NMR spectra were measured using a Bruker Avance Neo 600 MHz spectrometer (AV600NE02) equipped with a 5 mm TCI probe, with tetramethylsilane as the standard (0.00 ppm). Measurements were typically recorded using solutions in the solvents CD3CN, CDCls, or de-DMSO. Alternatively, a Bruker Avance Neo 600 MHz spectrometer (AV601) equipped with a 5 mm CPNMP probe or a Bruker Avance NEO 600 MHz spectrometer (AV600NEO) equipped with a 5 mm TCI probe was used. Measurements were generally performed at a probe temperature of 298 K. Any other measurement temperatures used are noted separately.

[0495] NMR peak list method

[0496] The ¹H NMR data of selected examples are presented in a series of ¹H NMR peak lists. For each signal peak, the ¹H value in ppm is listed first, followed by the signal intensity in parentheses. The ¹H value-signal intensity pairs are separated by semicolons.

[0497] The peak list of an example therefore has the form:

[0498] öi (Intensity:); 82 (Intensity2); ; 8 (Intensity); ; 8 n (Intensities)

[0499] The intensity of sharp signals correlates with the signal height in a printed representation of an ¹H NMR spectrum in cm⁻¹ 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.

[0500] Tetramethylsilane is used to calibrate the chemical shift of ¹H NMR spectra, or the chemical shift of the solvent if the sample does not contain tetramethylsilane. Therefore, ¹H NMR peak lists may, under certain circumstances, include the tetramethylsilane peak.

[0501] The lists of ¹H NMR peaks are equivalent to classical ¹H NMR representations and thus usually contain all peaks that are also listed in classical ¹H NMR interpretations. In addition, like classical ¹H NMR representations, they can show solvent signals, signals of stereoisomers of the compounds that may be the subject of the invention, and / or peaks of impurities.

[0502] 'H-NMR solvent signals, the tetramethylsilane signal, and the water signal in the respective solvent are excluded from the relative intensity calibration because the reported intensity values ​​can be very high. BYC240191 Abroad

[0503] - 75 - The peaks of stereoisomers of the compounds according to the invention and / or peaks of impurities usually have a lower intensity than the peaks of the compounds according to the invention (for example, at a purity of >90%).

[0504] Such stereoisomers and / or impurities can be typical for the respective manufacturing process. Their peaks can therefore help to identify the reproducibility of a manufacturing process based on “byproduct fingerprints”.

[0505] An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can identify the peaks of the target compounds as needed, possibly employing additional intensity filters. This identification is equivalent to the corresponding peak listing in classical ¹H NMR interpretation.

[0506] Further details on NMR data description with peak lists can be found in: “Citation of NMR Peaklist Data within Patent Applications” in the Research Disclosure Database Number 564025.

[0507] Production examples

[0508] Preparation of 1-(3,3-Dichloroprop-2-en-1-yl)-lH-imidazol-4-carboxylic acid methyl ester

[0509]

[0510] In a 41-gauge flask equipped with a stirrer and suspended condenser, 235 g (1.86 mol) of 1H-imidazole-4-carboxylic acid methyl ester were suspended in 2 L of acetonitrile, 1500 g (10.8 mol) of potassium carbonate and 750 g (4.12 mol) of 1,1,1,4-tetrachloropropane were added, and the mixture was stirred at room temperature for 4 days. The mixture was filtered by filtration, washed with acetonitrile, and the filtrate was concentrated under vacuum.

[0511] The residue was dissolved in approximately 0.6 L acetone, mixed with approximately 0.6 L cyclohexane, the acetone was distilled off under vacuum, and after cooling, the precipitate was collected by filtration. This precipitation was repeated a total of six times. The product was then dried under vacuum.

[0512] Yield: 266 g (60%).

[0513] LC-MS: logP (acidic) : 1.34 MH+: 236.8BYC240191 Foreign countries

[0514] - 76 -

[0515] Preparation of 2,5-Dichloro-1-(3,3-dichloroprop-2-en-1-yl)-1H-imidazol-4-carboxylic acid methyl ester

[0516]

[0517] 92.6g (394 mmol) l-(3,3-Dichloroprop-2-en-l-yl)-lH-imidazol-4-carboxylic acid methyl ester was added portionwise to 700ml dimethylformamide in a 21-flask with stirrer and internal thermometer at approx. 50°C with 123g (92 immol) N-chlorosuccinimide.

[0518] The necessary temperature control was achieved by heating in a heating bath or cooling in an ice-water bath. Stirring continued for another hour at 55°C.

[0519] The mixture was treated with aqueous NaHSOs solution using a KI-starch-paper control, concentrated under vacuum, and then treated with approximately 0.7 L water and approximately 1 L methyl tert-butyl ether / ethyl acetate (1:1 v / v). The solution was then treated with aqueous fGCCf solution until pH 8-9 was reached. The aqueous phase was extracted again with 0.8 L methyl tert-butyl ether / ethyl acetate (1:1 v / v), and the combined organic phases were washed with aqueous IVCCh solution. The mixture was dried with aqueous NaCl solution, then with Na₂SC > 4, and concentrated under vacuum.

[0520] Yield: 126 g (105%).

[0521] LC-MS: logP (acidic): 2.63 MH+: 304.8

[0522] Preparation of 2,5-Dichloro-1-(3,3-dichloroprop-2-en-1-yl)-1H-imidazol-4-carboxylic acid

[0523]

[0524] 126 g (414 mmol) of 2,5-dichloro-1-(3,3-dichloroprop-2-en-1-yl)-1H-imidazole-4-carboxylic acid methyl ester were dissolved in 0.5 l tetrahydrofuran-methanol-water and added portionwise with 10% sodium hydroxide solution, using sufficient methanol in each addition to the mixture to achieve a homogeneous solution. The reaction progress was monitored by thin-layer chromatography. BYC240191 Abroad

[0525] - 77 - (Petroleum ether-acetone) was followed. After complete reaction, the solution was treated with 10% hydrochloric acid to approximately pH 4, the organic solvents were distilled off under vacuum, and after cooling, the resulting precipitate was filtered off and washed with water containing approximately 1% formic acid (v / v).

[0526] The precipitate was dissolved in an aqueous solution of potassium carbonate, stirred at 50°C, cooled with an ice-water bath, treated with formic acid to approx. pH=3, left to stand for a few minutes, filtered off, washed with water and dried under vacuum.

[0527] The residue was covered with ethanol, heated under reflux, filtered off after cooling and dried.

[0528] Yield: 61.5 g (50%).

[0529] LC-MS: logP (acidic) : 1.72 MH+: 290.9 MH: 289

[0530] Preparation of 2,5-Dichloro-N-[(2-chloro-5-methylphenyl)sulfonyl - 1 -(3,3-dichloroprop-2-en- 1 -yl)- 1H-imidazol-4-carboxylic acid amide (1-2)

[0531] ci

[0532]

[0533] In a 21-liter flask equipped with a stirrer, 40 g (138 mmol) of 2,5-dichloro-l-(3,3-dichloroprop-2-en-l-yl)-lH-imidazol-4-carboxylic acid were dissolved in 475 ml of dichloromethane with 50.56 g (414 mmol) of dimethylaminopyridine and 79.4 g (414 mmol) of l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. After stirring for 10 minutes, 28.4 g (138 mmol) of 2-chloro-5-methylbenzenesulfonamide were added, and the mixture was diluted with 200 ml of dichloromethane. The reaction progress was monitored by LC-MS. After stirring for one day, the reaction mixture was partially concentrated under vacuum, treated with water and 62.5 mL of formic acid, the aqueous phase was extracted twice more with dichloromethane, the combined organic phases were washed three times with water, dried with sodium sulfate, and concentrated under vacuum. The residue was stirred with 350 mL of methanol, partially concentrated under vacuum, filtered after cooling, and dried. Yield: 63 g (94%).

[0534] LC-MS: logP (acidic) : 1.53 MH+: 477.8BYC240191 Foreign countries

[0535] - 78 -

[0536] Table 1 below lists further compounds of formula (I) which were produced analogously to the inventive example (1-2) given above.

[0537]

[0538] Table 1

[0539] Example

[0540] Structure 'IIAMR Peak List'

[0541] No.

[0542] 'H-NMR (600.0 MHz, CDC13), 5 (ppm): 9.5351 (0.8); 8.2569 (2.0); 8.2538 (2.0); 7.5690 (0.9); 7.5656 (0.9); 7.5553 (1.2); 7.5520 (1.2); 7.4868 (2.7); 7.4732 (1.9); 7.2609 (14.7); 5.8913 (1.2);

[0543] 1-1 5.8800 (2.5); 5.8687 (1.2); 5.3000 (0.4); 4.7559 (4.6); 4.7446 (4.5);

[0544] 4.5146 (7.3); 3.4923 (0.4); 3.4220 (16.0); 1.5505 (1.5); 0.0968 - r (0.2); 0.0053 (1.3); 0.0045 (1.2); -0.0001 (38.1); -0.0056 (1.4); - 0.1003 (0.2)

[0545] ’H-NMR(600.2 MHz, de-DMSO), 5 (ppm): 12.5416 (0.2); 7.9354 (7.4); 7.9326 (7.4); 7.5351 (3.6); 7.5216 (11.9); 7.5116 (5.7); 7.5089 (5.5); 7.4978 (1.7); 7.4952 (1.8); 6.4170 (5.2); 6.4062 (12.0); 6.3955 (5.3); 5.7561 (1.8); 4.8139 (0.2); 4.8030 (0.4); 4.7935 (16.0); 4.7827 (15.8); 4.2645 (0.2); 4.2527 (0.2); 3.3399 (1.6); 3.2822 (0.5); 3.1688 (9.7); 2.6163 (0.3); 2.6133 (0.4); 2.6102 1-2

[0546] NO (0.3); 2.6074 (0.1); 2.5406 (0.1); 2.5223 (0.5); 2.5192 (0.6); 2.5161 Y (0.7); 2.5073 (22.5); 2.5043 (48.7); 2.5012 (68.3); 2.4982 (49.5);

[0547] 2.4952 (22.7); 2.4073 (42.1); 2.3913 (0.3); 2.3882 (0.4); 2.3852 (0.5); 2.3821 (0.4); 2.3613 (0.1); 2.2993 (0.2); 1.9088 (0.2); 1.2847 (0.2); 1.2729 (0.3); 1.2610 (0.2); 0.0054 (0.3); -0.0001 (10.8); - 0.0057 (0.3)

[0548]

[0549] BYC240191 Ausland

[0550] - 79 - ’H-NMR(600.4 MHz, de-DMSO), 5 (ppm): 8.1452 (5.5); 7.6925 (12.1); 7.6907 (13.4); 6.9858 (2.6); 6.8604 (5.7); 6.7351 (2.8); 6.4102 (3.0); 6.3994 (7.1); 6.3886 (3.0); 5.7493 (3.6); 5.0591 1-3

[0551] H (16.0); 4.7966 (8.1); 4.7858 (8.1); 3.3613 (16.3); 3.2929 (1.7);

[0552] F'- 2.5254 (0.4); 2.5223 (0.6); 2.5192 (0.5); 2.5105 (11.5); 2.5074 (25.9); 2.5044 (36.9); 2.5013 (26.8); 2.4983 (12.8); -0.0002 (0.5) ’H-NMR(400.2 MHz, CDCh), 5 (ppm): 9.5346 (0.6); 8.1674 (2.7); 7.4126 (0.4); 7.4052 (6.2); 7.4022 (6.2); 7.2605 (19.6); 5.8956 (1.3); 5.8786 (3.0); 5.8617 (1.4); 4.7584 (4.9); 4.7415 (4.8);

[0553] 1-4 _ ) )

[0554] Y Z 3.0452 (0.3); 3.0279 (0.9); 3.0106 (1.2); 2.9933 (0.9); 2.9763 (0.4);

[0555] 1.5525 (10.7); 1.2960 (16.0); 1.2787 (15.8); 1.2639 (0.4); 1.2553 (0.5); 0.0079 (0.4); -0.0002 (11.8); -0.0084 (0.4)

[0556]

[0557] BYC240191 Abroad

[0558] - 80 - Examples of use

[0559] Meloidosvne incognita (MELGIN) test

[0560] Solvent: 7 parts by weight dimethylformamide

[0561] Emulsifier: 2.5 parts by weight alkylaryl polyglycol ether

[0562] To prepare a suitable active ingredient formulation, mix 1 part by weight of the active ingredient with the specified amounts of solvent and emulsifier, and dilute the concentrate with water to the desired concentration, taking into account the volume of soil into which it will be pressed. Ensure that the emulsifier concentration in the soil does not exceed 20 ppm. Dilute with water to prepare further test concentrations.

[0563] Pots filled with soil (loamy sand) are watered with the active ingredient solution. An egg-larva suspension of the southern root-knot nematode (Meloidogyne incognita) is added, the soil surface is sprinkled with lettuce seeds, and covered with quartz sand. The lettuce seeds germinate, and the seedlings develop. Galls form on the roots.

[0564] After 21 days, the nematicidal effect is determined based on the percentage of gall formation. 100% means that no galls were found; 0% means that the number of galls on the treated plants is the same as on the untreated control.

[0565] In this test, for example, the following compounds from the manufacturing examples showed superior effectiveness compared to the state of the art:

[0566] Active ingredient, structure, nematode species, active ingredient (%), effect, concentration after 14 days. Example: 1-2 MELGIN 1.0 ppm 90

[0567] 0 n / z — \

[0568] as per instructions / 0.5 ppm 90

[0569] N 1 Y /

[0570] 0.25 ppm 60

[0571] 'Y*

[0572] Example 1-1 MELGIN 0.5 ppm 95 according to requirements 0.25 ppm 75

[0573] \=C~

[0574] \

[0575] 'Y'

[0576]

[0577] BYC240191 Abroad

[0578] - 81 - Comparative example F F > CI / MELGIN 1 ppm 95

[0579] F 7 0 0

[0580] (Example 1-449 from 1 0 / 0.5 ppm 75 WO2018 / 083288) Cl % ^3, j'

[0581] d 1 )= / 0.25 ppm 0 CI '

[0582] Comparison example MELGIN 1 ppm 60 (Example 1-458 from 0.5 ppm 55 WO2018 / 083288) 0.25 ppm 0 Reference example 1 - 1 MELGIN 0.5 ppm 95

[0583] 0.25 ppm

[0584] A 0 V

[0585]

[0586] known from the examination procedure JP2019534276A (based on WO2018 / 083288).

Claims

BYC240191 Abroad - 82 - Patent claims 1. Combination of formula (I) (I), in the R 1 stands for chlorine or methyl, and R 2 for (Ci-C6)-alkyl, (Ci-C4)-alkoxy-(Ci-C2)-alkyl, (Ci-C4)-alkoxy-(C2-C4)-alkoxy-(Ci-C2)-alkyl, (C3-C5)-cycloalkyl-(Ci-C2)-alkyl, (C3-C5)-cycloalkyl or (Ci-C4)-haloalkoxy-(Ci-C2)-alkyl stands.

2. Compound of formula (I) according to claim 1, characterized in that R 1 for chlorine and R 2 for methyl, ethyl, isopropyl, methoxymethyl or difluoromethoxymethyl stands.

3. Use of the compound of formula (I) according to claim 1 or 2 for controlling animal pests.

4. Use according to claim 3, wherein the animal pests are nematodes.

5. Use of the compound of formula (I) according to claim 1 or 2 for the protection of plant propagation material.

6. A method for controlling animal pests, wherein at least one compound of formula (I) according to claim 1 or 2 is applied to the animal pests and / or their habitat. BYC240191 Abroad - 83 - 7. Agrochemical formulation containing at least one compound of formula (I) according to claim 1 or 2 in a biologically active amount of 0.00000001 to 98 wt.%, based on the weight of the agrochemical formulation, as well as extenders and / or surfactants.

8. Agrochemical formulation according to claim 7, characterized in that it additionally contains a further agrochemical active ingredient.

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