ES2857806T3 - 2-Alkylimidazolyl-substituted carboxamides as pesticides - Google Patents

Abstract

Compounds according to the formula (I-1) ** (See formula) ** in which V represents hydrogen, W represents hydrogen, Y represents methyl, A represents methyl, ethyl or cyclopropyl, T represents an electron pair or oxygen , L1 represents a residue of the series hydrogen, methyl, trifluoromethyl, trichloromethyl, isopropyl, isobutyl, 3-methylbutyl (isopentyl), phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl , 3-pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl and benzyl, L2 represents hydrogen or methyl, or L1 and L2 together represent vinyl, prop-1-en-2-yl, (1E) -prop-1-en-1-yl, (1Z) -prop-1-en-1-yl or cyclopropyl, L3 represents a residue of the hydrogen series, S (O) nR1a, OR1b and N (R2) (R3 ), in which for the case that L1 and / or L2 represents hydrogen or optionally substituted alkyl, L3 represents a residue of the series S (O) nR1a, OR1b and N (R2) (R3), R1a represents a residue of the methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclop series ropilmethyl, 2,2-dimethylpropyl, 2-methoxy-2-oxoethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl and 2-pyrimidyl, R1b represents a residue of the hydrogen, methyl, ethyl, 2,2 series , 2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3-chlorophenyl and 4-chlorophenyl, R2 and R3 together with N represent a heterocycle of the series U-2, U-4, -U-5 and U-13, ** (See formula) ** Xb represents trifluoromethyl, methyl or cyclopropyl, m represents a number 0 or 1, n represents a number 0 or 2, and their salts.

Description

DESCRIPTION

2-Alkylimidazolyl-substituted carboxamides as pesticides

The present application refers to new heterocyclic compounds, processes and intermediates for their preparation and their use to combat animal pests.

Heterocyclic compounds, inter alia also imidazolylcarboxamides, which can be used as insecticides, are described in WO 2011/009804 A2.

Modern insecticides must satisfy many demands, for example, regarding the degree, persistence and spectrum of their action and possible use. Questions of toxicity, preservation of beneficial species and pollinators, environmental properties, application rates, ability to combine with other active ingredients or formulation adjuvants play a role, as does the question of the effort required for the synthesis of an active principle, additionally, resistances may appear, to mention just a few parameters. For all these reasons alone, the search for new plant protection agents cannot be considered complete, and there is a constant need for new compounds with improved properties compared to known compounds, at least in relation to individual aspects.

It was an object of the present invention to provide compounds by which the spectrum of pesticides is completed in various aspects.

This objective, as well as other objectives not explicitly mentioned, which can be discerned or derived from the relationships explained herein, are achieved by the provision of compounds of formula (I)

in which

V represents hydrogen,

W represents hydrogen,

Y represents methyl,

A represents methyl, ethyl or cyclopropyl,

T represents a pair of electrons or oxygen,

L1 represents a residue of the series hydrogen, methyl, trifluoromethyl, trichloromethyl, isopropyl, isobutyl, isopentyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl, 3-pyridinyl, 4 -pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl and benzyl,

L2 represents hydrogen or methyl, or

L1 and L2 together represent vinyl, prop-1-en-2-yl, (1 £) -prop-1-en-1-yl, (1Z) -prop-1-en-1-yl or cyclopropyl, L3 represents a remainder of the hydrogen series, S (O) nR1a, OR1b and N (R2) (R3), in which for the case that L1 and / or L2 represents hydrogen or optionally substituted alkyl, L3 represents a residue of the series S (O) nR1a, OR1b and N (R2) (R3),

R1a represents a residue of the series methyl, ethyl, isopropyl, isobutyl, tert-butyl, cidopropylmethyl, 2,2-dimethylpropyl, 2-methoxy-2-oxoethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl and 2 -pyrimidyl,

R1b represents a residue of the series hydrogen, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3-chlorophenyl and 4-chlorophenyl,

R2 and R3 together with N represent a heterocycle of the series U-2, U-4, -U-5 and U-13,

Xb represents trifluoromethyl, methyl or cyclopropyl,

m represents a number 0 or 1,

n represents a number 0 or 2,

and its salts.

Especially preferred substituents or ranges of the disclosed moieties in the compounds according to the invention are explained below. Taking into account the position of the carboxamide group in the imidazole residue, the very particularly preferred structure (I-1) results.

V represents hydrogen,

W represents hydrogen,

Y represents methyl,

A represents hydrogen or methyl,

T represents a pair of electrons,

L1 represents a residue of the series hydrogen, methyl, isopropyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 4-chloropyridine-3 -yl, 2-pyrimidyl and benzyl,

L2 represents hydrogen or methyl, or

L1 and L2 together represent vinyl,

L3 represents a residue of the hydrogen series, S (O) nR1a, OR1b and N (R2) (R3),

R1a represents a residue of the series methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopropylmethyl, 2,2-dimethylpropyl, 2-methoxy-2-oxoethyl, phenyl, benzyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl and 2-pyrimidyl, R1b represents a residue of the series hydrogen, methyl, cyclopropylmethyl, benzyl and 3-chlorophenyl,

R2 and R3 together with N represent a heterocycle of the series U-2, U-4 and U-5,

Xb represents trifluoromethyl,

m represents a number 0 or 1,

n represents a number 0 or 2,

and its salts.

In a preferred embodiment the invention relates to the compounds of formula (I-1a).

In another preferred embodiment the invention relates to the compounds of formula (I-1c).

In another preferred embodiment the invention relates to the compounds of formula (I-1d).

Compounds of formula (I-1c) or (I-1d) and very especially of formula (I-1c) are especially preferred. Another object of the invention are the intermediate products of formulas (II) and (III)

in which the mentioned moieties have the meanings according to claim 1.

The compounds of formula (I) can be found, depending on the type of substituents, as geometric isomers and / or as optically active isomers or corresponding isomeric mixtures in different composition. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The invention thus encompasses both pure stereoisomers and any mixture of these isomers.

Compounds of formula (I-1) can be synthesized for example according to procedures A to F as described in the following schemes.

Procedure A

Procedures B-1 and B-2

Procedure B-2, when L3 represents SR1a

Procedure C

BuLi = n-butyllithium

Procedure D

tr-It (1 -0

BuLi = n-butyllithium

Procedure E

Procedure F

BuLi = n-butyllithium

The imidazolylcarboxylic acids of the formula (IV-1) required for process A are commercially available or can be prepared, for example, according to procedures known from the literature, for example, HOFFMANN-LAROCHE INC. patent: US2006 / 0019949 A 1,2006.

The imidazolylcarboxylic acids of the formula (VII-1) required for process B are commercially available or can be prepared, for example, according to procedures known from the literature, for example O'Connell, John F .; Parquette, Jonathan; Yelle, William E .; Wang, Wilhelm; Rapoport, Henry, Synthesis 1988, 767-771, BASF Aktiengesellschaft patent: US4864030 A1, 1989, Takeda Pharmaceutical Company Limited Patent: EP2530078 A1, 2012, TAISHO PHARMACEUTICAL CO., LTD. patent: US2012 / 10414 A1, 2012, Underline, Ramachandran P .; Thurber, Ernest L .; Rasmussen, Paul G., Tetrahedron, 1994, 50, 2641-2656.

The 3-aminopyridines of formula (VI) required for processes A and B are commercially available or can be prepared, for example, according to procedures known from the literature, for example Liu, Zhen-Jiang; Vors, Jean-Pierre; Gesing, Ernst R. F .; Bolm, Carsten, Advanced Synthesis and Catalysis, 2010, 352, 3158-3162, BAYER CROPSCIENCE AG Patent: US2010 / 305124 A1, 2010, Shafir, Alexandr; Buchwald, Stephen L., Journal of the American Chemical Society, 2006, 128, 8742-8743.

The L3Hs (eg thiols, alcohols, pyrazoles, triazoles, etc.) of formula (IX) required for process B are commercially available or can be prepared by general procedures known in organic chemistry.

Most of the metalorganyls (eg vinyl boronic acid / ester, etc.) required for process D, as well as the necessary catalysts, are commercial products or can be prepared according to generally known procedures in organic chemistry.

Most of the alkynes (eg, phenylacetylene etc.) required for process E, and the necessary catalysts, are commercial products or can be prepared by generally known procedures in organic chemistry.

Most of the trifluoromethanesulfonates required for process F are commercial products or can be prepared according to generally known procedures in organic chemistry.

Numerous reaction conditions have been described for the lithiation coupling procedure (Procedures C, D and F), for example, Hoechst Aktiengesellschaft Patent: US4764624 A1, 1988. Ohta, Shunsaku; Yamamoto, Tetsuya; Kawasaki, Ikuo; Yamashita, Masayuki; Katsuma, Hideo; Nasako, Rieko; Kobayashi, Kazuhiro; Ogawa, Kazuo, Chemical and Pharmaceutical Bulletin, 1992, 40, 2681-2685. Hara, Kenji; Iwahashi, Keiji; Kanamori, Yoshikazu; Naito, Satoshi; Takakusagi, Satoru; Uosaki, Kohei; Sawamura, Masaya, Chemistry Letters, 2006, 35, 870-871.

Examples of solvents are: diethyl ether, tetrahydrofuran.

Examples of lithiating agents are: n-butyllithium, lithium diisopropylamine, lithium tert-butylate.

The reaction temperature for the initial lithiation step is optionally between -100 and -75 ° C.

Amidation procedure

The compounds of the formula (I-1) and the intermediates of the formula (IX-1) in the process according to the invention can be synthesized by means of amidation reactions known from the literature, or analogously to those examples explicitly mentioned.

Numerous reaction conditions have been described for the amidation step, for example G. Benz in Comprehensive Organic Synthesis, 1st Ed., Pergamon Press, Oxford, 1991, Vol. 6, p. 381-417; P.S. Bailey et al. in Comprehensive Organic Functional Group Transformation, 1st Ed., Elsevier Science Ltd., Oxford, 1995, Vol. 5, p.

257-308 and RC Larock in Comprehensive Organic Transformations, 2nd Ed., Wiley-VCH, New York, Weinheim, 1999, p. 1929-1994. Some of these reactions proceed through intermediate carboxylic acid chlorides, which can be used in isolation or in situ generated form.

The amidation reactions are carried out, optionally, in the presence of a condensing agent, optionally in the presence of an acid acceptor, and optionally in the presence of a solvent.

Suitable condensing agents are all condensing agents that can be used customarily for amidation reactions of this type. By way of example, activation reagents such as phosgene, phosphorous trichloride, phosphorous oxychloride, oxalyl chloride, oxalyl bromide or thionyl chloride are mentioned; carbodiimides such as N, N'-dicyclohexylcarbodiimide (DCC) and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide (EDCI), or other common condensing agents such as phosphorous pentoxide, polyphosphoric acid, N, N'- carbonyldiimidazole, 2-Chloropyridine 1-methoiodide (Mukaiyama's reagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, bromotripyrrolidinophosphonium hexafluorophosphate (BROP- hexaphorophos- benzotriazol-1-yloxy) tris (dimethylamino) phosphonium (BOP), N, N, N ', N'-bis (tetramethylene) chlorouronium tetrafluoroborate, O- (1H-benzotriazol-1-yl) -N, N hexafluorophosphate , N ', N'-tetramethyluronium (HBTU), O- (1H-benzotriazol-1-yl) -N, N, N'-hexafluorophosphate, N'-bis (tetramethylene) uronium, O- (1H-benzotriazole tetrafluoroborate -1-yl) -N, N, N ', N'-tetramethyluronium (TBTU), tetrafluoroborate O- (1H-benzotriazol-1-yl) -N, N, N ', N' bis (tetramethylene) uronium, O- ( 7-azabenzotriazol-1-¡l) -W, W, W 'hexafluorophosphate , W'-tetramethyluron (HATU), 1-hydroxybenzotriazole (HOBt) and 4- (4,6-dimethoxy-1,3,5-tr¡az¡n-2-¡l salt ) -4-methylmorpholine (DMT.MM), generally available as a chloride. These reagents can be used separately or in combination.

As acid acceptor all customary inorganic or organic bases are taken into account, for example organic amines such as triethylamine, diisopropylethylamine, W-methylmorpholine, pyridine or WW-dimethylaminopyridine, alkali metal or alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, or cesium carbonate; alkali metal bicarbonates such as sodium bicarbonate or potassium bicarbonate. The amidation reaction in the processes according to the invention is optionally carried out in the presence of a suitable reaction adjuvant such as, for example, W, W-dimethylformamide or WW-dimethylaminopyridine. As suitable solvent or diluent all inert organic solvents are taken into account, for example aliphatic or aromatic hydrocarbons (such as petroleum ether, toluene, cyclohexane), halogenated hydrocarbons (such as chlorotoluene, dichlorobenzene, dichloromethane, chloroform, 1,2- dichloroethane), ethers (such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane), esters (such as ethyl or methyl acetate), nitrohydrocarbons (such as nitromethane, nitroethane, nitrobenzene), nitriles (such as acetonitrile, propionitrile , butyronitrile, benzonitrile), amides (such as W, W-dimethylformamide, W, W-dimethylacetamide, W-methylformanilide, W-methylpyrrolidone, hexamethylphosphoramide), and also dimethylsulfoxide, sulfolane or water or mixtures of the solvents mentioned.

It is also possible to use mixed anhydrides to prepare the compounds of formula (I-1) (see Anderson, George W .; Zimmerman, Joan E .; Callahan, Francis M., J. Am. Chem. Soc. 1967, 89, 5012-5017). In this process, it is possible to use chloroformic esters, for example methyl chloroformate, ethyl chloroformate, isobutyl chloroformate and isopropyl chloroformate. It is equally possible for this purpose to use diethylacetyl chloride, trimethylacetyl chloride and the like.

In the following, the statements referring to the compounds of the formula (I) are, of course, also applicable to the compounds of the formulas (I-1) and (I-1a) to (I-1d), which are covered by formula (I).

Procedures and uses

The invention also relates to a method for combating animal pests, in which compounds of formula (I) are allowed to act on animal pests and / or their habitat. Preferably the control of animal pests is carried out in agriculture and forestry, and in the protection of materials. This preferably excludes procedures for the surgical or therapeutic treatment of the human or animal body and diagnostic procedures that are performed on the human or animal body.

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

In the context of the present application, the term pesticide in each case also always encompasses the term phytoprotective agent

The compounds of formula (I) are suitable in the case of good plant compatibility, favorable warm-blooded animal toxicity and good environmental compatibility for the protection of plants and plant organs against biotic and abiotic stress factors, for increase crop yields, improve the quality of the harvested product and to combat animal pests, in particular insects, arachnids, helminths, in particular nematodes and mollusks, which occur in agriculture, in horticulture, in animal husbandry, in aquaculture, in forests, in gardens and leisure facilities, in the protection of stored products and materials as well as in the hygiene sector.

In the context of the present patent application, the term "hygiene" should be understood as any and all measures, dispositions and procedures that have as their objective the prevention of diseases, especially infectious diseases, and that serve to protect the health of the humans and animals and / or protect the environment and / or maintain cleanliness. According to the invention, this especially includes measures for cleaning, disinfection and sterilization, for example of textiles or hard surfaces, especially surfaces made of glass, wood, cement, porcelain, ceramic, plastic or metal (s), in order to ensure that said surfaces are free of hygiene pests and / or their secretions. The scope of protection of the invention at this point, preferably, excludes surgical or therapeutic treatment procedures to be applied to the human body or animal bodies, and diagnostic procedures that are carried out on the human body or bodies. of animals.

The term "hygiene sector" covers all areas, technical fields and industrial applications where these hygiene measures, provisions and procedures are important, for example with respect to hygiene in kitchens, bakeries, airports, bathrooms, sinks, hypermarkets hotels, hospitals, stables, animal keeping areas, etc.

The term "hygiene pest" should therefore be understood as one or more animal pests whose presence in the hygiene sector is problematic, especially for health reasons. Therefore, a primary purpose is to avoid or limit to a minimum degree the presence of hygiene pests and / or their exposure to the hygiene sector. This can be achieved especially through the use of a pesticide that can be used both for the prevention of infestation and for the prevention of an existing infestation. It is also possible to use formulations that prevent or reduce exposure to pests. Hygiene pests include, for example, the organisms mentioned below.

The term "hygiene protection" therefore covers all acts by which these hygiene measures, provisions and procedures are maintained and / or improved.

The compounds of the formula (I) can preferably be used as pesticides. They are active against normally sensitive and resistant species as well as against all stages of development or specific stages of development. The pests mentioned above include:

phylum arthropod pests, in particular of the arachnid class for example Acarus spp., for example Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., for example Aculus fockeui, Aculus schlechtendali, Amblyomma spp ., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., For example Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagooteides farinayss, Dermatophagooteides pteronyssus pteronysstracentinae, Dermatophagooteides farinacentinae. spp., for example Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., for example Eutetranychus banksi, Eriophyes spp., for example Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., for example Hemitarsonemus latus) spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., for example Oligonychus coffeae, Oligonych us coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., eg Panonychus citri (= Metatetranychus citri) , Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki. ., for example Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici;

from the class of Chilopods for example Geophilus spp., Scutigera spp .;

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

from the class of the Diplopoda, for example Blaniulus guttulatus;

from the class of insects, for example from the order of the Blatodeans, for example Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., for example Periplaneta americana , Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa;

from the order of the Coleoptera, for example Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agriotes spp., for example Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anthrapphora spp. ., for example Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., for example Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., for example Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., For example Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., For example Chaetocnema confinis, Chaetocnema denticulata. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., For example Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculi o sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp. virgifera virgifera, Diabrotica virgifera zeae, Saidcrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., for example Epilachna borealis, Epilachna varivestis, Epitrix spp., for example Epitrix cucumeris, Epitrix cucumeris, Epitrix cucumeris, Epitrix cucumeris, for example Epitrix cucumeris subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., Hypothenemus spp. pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., e.g. Leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus (= Hyperodes) spp., Lixus spp., Luperodesomorphactus. , Megascelis spp., Melanotus spp., For example Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., For example Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogaleucellacus spp. rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., for example Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., for example Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., for example Phyllotreta armoraciae, Phyllotylloty pustapesilla, Phyllotretallotypistrio spp. ., Prostephanus truncatus, Psylliodes spp., For example Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferchouginophilusmar spp., Rhynchophorus ferchouginophilusmar perforated spp. granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., for example Sternechus paludatus, Symphyletes spp., Tanymecus spp., for example Tanymecus dilaticollis, Tanymeitorium molluscum, Tanllymeides molluscum, Tehnymecus paludatus, Tanymeitor mauretanicus, Tribolium spp., for example Tribolium audax, Tribolium castaneum, Trib olium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., for example Zabrus tenebrioides;

from the order of the dermaptera, for example Anisolabis maritime, Forficula auricularia, Labidura riparia;

from the order of Diptera, for example Aedes spp., for example Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., for example Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., for example Anopheles quadrculatus, for example Anopheles quadrculatus. Anopheles gambiae, Asphondylia spp., Bactrocera spp., For example Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chryso Cochialis spp., Chrysochialis spp., Chrysomya sppv. spp., Contarinia spp., for example Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., for example Culex Quinicofascia spp., Culex quinicofascia spp. spp., Cuterebra spp., Dacus oleae, Dasineura spp., for example Dasineura brassicae, Delia spp., for example Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., For example Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossrellina spp., Haematopota spp., Hydraulic spp. , Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., For example Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., For example Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., Musca spp. ., for example Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyia spp., for example Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotombia spp., Phlebotombia spp., Plebotombia spp. Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., For example Rhagoletis cingulata, Rhagoletis complet, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rellahagoletis pomondax, Rellahagoletis Sarcophaga spp., Simulium spp., For example Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., For example Tipula paludosa, Tipula simplex, Toxotrypana curvicauda;

from the order of the Hemiptera, for example, Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., for example Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthroley spp., Aleurocanthrodenus spp. Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., For example Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., For example Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata. , Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola. ., for example Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycau dus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., for example Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Château fragaepuondisiphonis, Château fragaeplu-siphloris, Châtiii-foli-loris ransomatum, Chaetl-siploris spp. Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., For example Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribaryis, Cryptoneosten spp. Spp., Cryptomyzus ribaryis, Cryptoneosten spp. , Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., Eg Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca abr. , Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., For example Eriosoma americanum, Eriosoma lanigerum, Er iosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsyllapteris prisalodis heteropsyltauni, Heteropsyllaptera cubana, Heteropsyltauni protopia, Heteropsyllapteriniscapterulauni , Icerya spp., Eg Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Eg Lecanium corni (= Parthenolecanium corni), Lepidosaphes spp., Eg Lepidosaphes ulmi, Lipaphis eryscasimi, Lopidosaphes ulmi, Lipaphis eryscasimi, Lopidosaphes ulmi, Lipaphis eryscasimi, Lopidosaphes ulmi. Lycorma delicatula, Macrosiphum spp., For example Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophum lilii. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix s pp., eg Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., Paratrioza sppiopp. , for example Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., For example Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., For example Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., For example Phorodon humuli, Phylloxera sp. ., for example Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., for example Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulyrus spp., Pteromalus spp., Pteromalus spp. Quadraspidiotus spp., For example Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., For example Rhopalosiphum maidis, Rhopalosiphum, Rhopalosiphum, Rhopalosipissetia padisdomisetia, oxipalosedomissetia rhophissetia, oxypalosephissetia settia, Rhopalosiphumissetia fossiasettiacantissetia miranda, Saissetia neglecta, Saissetia oleae, Sca phoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetrapp. for example Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., for example Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .;

from the suborder Heteroptera for example Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., for example Cimex adjunctus, Cimex hemipterus lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., for example Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus spp. , Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., For example Lygocoris pabulinus, Lygus spp., For example Lygus elisus, Lygus linevatus, Macrogus elisus, Lygus linevatus , Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., For example Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., For example Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .;

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

from the order of the Isopoda, for example Armadillidium vulgare, Oniscus asellus, Porcellio scaber;

from the order of Isoptera, for example Coptotermes spp., for example Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp. for example Reticulitermes flavipes, Reticulitermes hesperus;

from the order of Lepidoptera for example Achroia grisella, Acronicta major, Adoxophyes spp., for example Adoxophyes orana, Aedia leucomelas, Agrotis spp., for example Agrotis segetum, Agrotis ipsilon, Alabama spp., for example Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., for example Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia reivopulara theppulara, Caloptuara Carpocara theppulara. pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., e.g. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocropp. spp. spp. spp. ., Copitarsia spp., Cydia spp., For example Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Ear ias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., eg Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana. , Eupoecilia ambiguella, Euproctis spp., For example Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., For example Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Helicoverpa spp. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., For example Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp. example Leucoptera coffeella, Lithocolletis spp., for example Lithocolletis blancardella, Lithophane antennata, Lobesia spp., for example Lobesia botrana, Loxagrotis albicosta, Lymantria spp., p For example Lymantria dispar, Lyonetia spp., for example Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Oiketicus spp., Oiketicus spp. , Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., For example Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp., For example Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Or Phthorimaea spp., Or Phthorimaea spp., For example Phthorimaea spp., For example Phthorimaea spp. , Phyllocnistis citrella, Phyllonorycter spp., For example Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., For example Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylospenistella (= Plupp. , Protoparce spp., Pseudaletia spp., For example Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Eg Schoenobius bipunctifer, Scirpophaga spp., Eg Scirpophaga innotata, Scotia segetum, Sesamia spp., Eg Sesamia inferens, Sparganothistera spp., Spodoptera spp., Spodoptera spp., Spodoptera spp. eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea clopoda spp., Tinea picholaella spp. tapetzella, Trichoplusia spp., for example Trichoplusia ni, Tryporyza incertulas, Tuta absolu, Virachola spp .;

from the order of the Orthoptera or Saltatoria, for example Acheta domesticus, Dichroplus spp., Gryllotalpa spp., for example Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., for example Locusta migratoria, Melanoplus spp., for example Melanoplus devastator, Paratlaiensus, usssurratlaiensus Schistocerca gregaria;

from the order of the Phyraptera, for example Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .;

from the order of the Psocoptera, for example Lepinotus spp., Liposcelis spp .;

from the order of the siphonaptera, for example Ceratophyllus spp., Ctenocephalides spp., for example Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

from the order of Thysanoptera, for example Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici. Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., Eg Thrips palmi, Thrips tabaci;

from the order of the Zigenthomes (= Thysanuros), for example Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

from the class of Symphyla, for example Scutigerella spp., for example Scutigerella immaculata;

phylum pests of molluscs, for example of the class of bivalves, for example Dreissena spp .;

as well as from the class of gastropods for example Arion spp., for example Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., for example Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;

plant pests of the phylum of nematodes, that is to say parasitic nematodes of plants, in particular Aglenchus spp., for example Aglenchus agricola, Anguina spp., for example Anguina tritici, Aphelenchoides spp., for example Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp. , for example Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., for example Cacopaurus pestis, Criconemellamellacurve, eg Criconemeltamellacurve, Criconemellaenspp. , Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., For example Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., For example Ditylenchus dipsaci, Globodera spp., Globodera spp., Globoderapp. rostochiensis, Helicotylenchus spp., for example Helicotylen chus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., for example Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., for example Longidorus africanus, Meloidogyne for example Meloidogyne, Meloidogyne for example Meloidogyne spp. chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., eg Paratrichodorus minorlen, Paratylenchus spp. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., For example Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutelloneguodina spp., Scutelloneguodina spp. , for example Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., for example Tylenchorhynchus annulatus, Tylenchulus spp., for example Tylenchulus semipenetrans, X iphinema spp., for example Xiphinema index.

The compounds of formula (I) can optionally be used in certain concentrations or application amounts also as herbicides, protectants, growth regulators or agents for improving the properties of plants, such as microbicides or gametocides, for example as fungicides, antifungals, bactericidal, virucidal (including antiviral agents) or as agents against MLO (mycoplasma-like organism) and RLO (Rickettsia-like organism). If appropriate, they can also be used as intermediates or pre-agents for the synthesis of other active ingredients.

Formulations

The present invention further relates to formulations and application forms prepared therefrom. as pesticides such as for example soaking, dipping and spraying broths, comprising at least one compound of formula (I). If necessary, the application forms contain other pesticides and / or adjuvants that improve the effect such as penetration promoters, for example vegetable oils such as for example rapeseed oil, sunflower oil, mineral oils such as for example paraffin oils , alkyl esters of vegetable fatty acids such as for example methyl ester of rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as for example alkylsiloxanes and / or salts for example organic or inorganic ammonium or phosphonium salts such as for example ammonium sulfate or diammonium hydrogen phosphate and / or agents that promote retention such as for example dioctyl sulfosuccinate or polymers of hydroxypropylguar and / or humectants such as for example glycerol and / or fertilizers such as for example fertilizers containing ammonium, potassium or phosphorus.

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

These are preferably formulations or application forms containing auxiliary agents such as, for example, extenders, solvents, spontaneity promoters, vehicles, emulsifiers, dispersants, antifreezes, biocides, thickeners and / or other auxiliary agents such as, for example, adjuvants. An adjuvant in this context is a component that enhances the biological action of the formulation, without the component itself having a biological action. Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the surface of the sheets, or penetration.

These formulations are prepared in a known manner, for example by mixing the compounds of formula (I) with auxiliary agents such as, for example, extenders, solvents and / or solid carriers and / or other auxiliary agents such as, for example, surface-active substances. The preparation of the formulations takes place either in suitable facilities or also before or during the application.

As auxiliary agents it is possible to use those substances which are suitable for conferring on the formulation of the compounds of formula (I) or on the application forms prepared from these formulations (such as, for example, useful pesticides such as spray broths or coating products of seeds) special properties, such as certain physical, technical and / or biological properties.

Suitable extenders are, for example, water, polar and non-polar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which optionally also They can be substituted, etherified and / or esterified), of ketones (such as acetone, cyclohexanone), esters (also fats and oils) and (poly-) ethers, of simple and substituted amines, amides, lactams (such as N -alkylpyrrolidones) and lactones, from sulfones and sulfoxides (such as dimethylsulfoxide).

When using water as an extender, for example organic solvents can also be used as auxiliary solvents. As liquid solvents, essentially: aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example, fractions of petroleum, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide as well as water.

In principle all suitable solvents can be used. Suitable solvents are for example aromatic hydrocarbons such as for example xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as for example chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons such as for example cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as for example methanol, ethanol, isopropanol, butanol or glycol as well as their ethers and esters, ketones such as for example acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide as well as water . In principle, all suitable vehicles can be used. Particularly suitable vehicles are: for example ammonium salts and natural rock flours such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as highly dispersed silicic acid , aluminum oxide and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Vehicle mixtures of this type can also be used. As vehicles for granules the following are considered: for example, broken and fractionated natural rocks such as calcite, marble, pumice stone, sepiolite, dolomite as well as synthetic granules of inorganic and organic flour, as well as granules of organic material such as sawdust, paper. , coconut shells, corncobs and tobacco stalks.

Liquefied gaseous extenders or solvents can be used. In particular those extenders or carriers, which are gaseous at normal temperature and normal pressure, for example aerosol propellant gases such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.

Examples of emulsifying and / or foaming agents, dispersants or wetting agents with ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl restaurants), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of sulfate, sulfonate and phosphate containing compounds, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, waste lignin sulfite bleaches, and methyl cellulose. The presence of a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when the application takes place in water.

As additional auxiliary agents, colorants such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic colorants such as alizarin, azo and metal phthalocyanine and nutrients and trace elements such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts.

In addition, stabilizers such as cold stabilizers, preservatives, antioxidants, photoprotective agents or other agents that improve chemical and / or physical stability may be contained. Furthermore, foaming or antifoaming agents may be contained.

Likewise, the formulations and forms of application derived therefrom may contain as additional auxiliary substances also adhering agents such as carboxymethylcellulose, pulverulent, granular or latex polymers, natural and synthetic such as gum arabic, polyvinyl alcohol, poly (vinyl acetate) as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other auxiliary substances can be mineral and vegetable oils.

If necessary, further auxiliary substances may be contained in the formulations and the application forms derived therefrom. Such additives are for example aromatic substances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, wetting agents, spreading agents. In general, the compounds of formula (I) can be combined with any solid or liquid additive, which is commonly used for formulation purposes.

As retention promoters, all those substances which reduce the dynamic surface tension, such as, for example, dioctyl sulfosuccinate or increase the viscoelasticity, such as, for example, hydroxypropyl guar polymers are taken into account.

As penetration promoters, all those substances that are commonly used to improve the introduction of agrochemical active ingredients into plants are taken into account in the present context. Penetration promoters are defined in this context because they can be introduced into the cuticle of plants from the application broth (generally aqueous) and / or from the spray coating product and thus can increase the mobility of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Examples are alcohol alkoxylates such as, for example, coconut fat ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as, for example, rapeseed oil or soybean oil methyl ester, alkoxylates fatty amine such as for example tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as for example ammonium sulfate or diammonium hydrogen phosphate.

The formulations preferably contain between 0.00000001 and 98% by weight of the compound of formula (I), particularly preferably between 0.01 and 95% by weight of the compound of formula (I), very especially preferably between 0.5 and 90% by weight of the compound of formula (I), relative to the weight of the formulation.

The content of the compound of formula (I) in the application forms prepared from the formulations (in particular pesticides) can vary within wide ranges. The concentration of the compound of formula (I) in the application forms can usually be between 0.00000001 and 95% by weight of the compound of formula (I), preferably between 0.00001 and 1% by weight, with with respect to the weight of the application form. The application is carried out in the usual way adapted to one of the application forms.

Mixtures

The compounds of formula (I) can also be used in mixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiological agents, useful insects, herbicides, fertilizers, bird repellants, phytotonics, sterilizers, protectants, semiochemicals and / or plant growth regulators, for example to broaden the spectrum of action, extend the effective duration, increase the active speed, prevent repellency or prevent development of resistance. Furthermore, such combinations of active ingredients can improve plant growth and / or tolerance to abiotic factors such as, for example, high or low temperatures, to dryness or to a high salt content in water or soil. . It can also improve the flowering and growth behavior of the fruit, optimize the germination and rooting capacity, facilitate the harvest and increase the yields of the harvest, influence the ripening, increase the quality and / or the nutritional value of the products of the harvest, prolong shelf life and / or improve the processability of harvest products.

Furthermore, the compounds of formula (I) can be found in a mixture with other active or semiochemical principles, such as attractants and / or repellants for birds and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of formula (I) can be used in mixtures with agents to improve the properties of plants such as, for example, growth, yield and quality of the harvest material.

In an embodiment according to the particular invention, the compounds of formula (I) are found in formulations or in the application forms prepared from these formulations in admixture with other compounds, preferably those described above.

When one of the compounds mentioned below can be found in different tautomeric forms, these forms may also be covered, although these are not explicitly mentioned in each case. All the mixture components mentioned, if they have the capacity due to their functional groups, optionally form salts with suitable bases or acids.

Insecticides / acaricides / nematicides

Active ingredients named by their "common name" are 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 (eg http: // www.alanwood.net/pesticides). The classification is based on the IRAC Modes of Action Classification Scheme applicable at the time of filing of this patent application.

(1) Acetylcholinesterase (AChE) inhibitors, such as, for example, carbamates, for example alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiophencarb, phenobucarb, methocarbonate, isocarbonate, methylcarbonate , metolcarb, oxamyl, pyrimicarb, propoxur, thiodicarb, thiophanox, triazamate, trimetacarb, xmc and xylylcarb or organophosphates, for example acephate, azamethipos, azymphon-ethyl, azymphon-methyl, cadusaphos, chloromethovinosphos, chloroform-methyphos, chloroform-methyphoses , cyanophos, demeton-S-methyl, diazinone, dichlorvos / DDVP, dicrotphos, dimethoate, dimethylvinphos, disulfoton, EPN, ethiona, ethoprofos, Famphur, fenamiphos, fenitrothione, fenthione, phostiazate, feptenophos, imitiophos phosphoryl) isopropyl salicylate, isoxationa, malathion, mecarbam, methamidophos, metidation, mevinphos, monochotophos, naled, omethoate, oxydemetonmethyl, parathion-methyl, phentoate, phorate, fosalone, phosmet, phosphamidone, phoxim, pirimiphos-methyl, profenphos, propetaphos, protiophos, pyraclphos, pyridaphenthione, quinalphos, sulfotep, tebupyrinfos, temephos, terbuphos, tetrachlorvinphos, thiometon, triazophos, trichlorfon. and vamidothione.

(2) GABA-controlled chloride channel blockers, such as for example cyclodiene-organochlorine, for example chlordane and endosulfan or phenylpyrazole (fiprole), for example ethiprole and fipronil.

(3) Sodium channel modulators, such as for example pyrethroids, for example acrinathrin, allethrin, dcis-trans allethrin, d-trans allethrin, bifenthrin, bioalethrin, S-cyclopentenyl isomer bioalethrin, bioresmethrin, cycloprothrin, cyfluthrin, beta -cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alphacypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [isomer (1R) -trans], deltamethrin [) isomer (lEnthrin [) - isomeric )), Esfenvalerate, Etofenprox, Phenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, Tau-fluvalinate, Halfenprox, Imiprotrin, Cadethrin, Momfluorothrin, Permethrin, Phenothrin [(1R) -trans isomer], Pralemethrin, Pyrethrin, Silyrine tefluthrin, tetramethrin, tetramethrin [(1R) isomer], tralomethrin and transfluthrin or DDT or methoxychlor.

(4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), such as for example neonicotinoids, for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupiradifurone.

(5) Allosteric modulators of the nicotinic acetylcholine receptor (nAChR), such as for example spinosyns, for example spinetoram and spinosad.

(6) Allosteric modulators of the glutamate-dependent chloride channel (GluCl), such as for example avermectin / milbemycin, for example abamectin, emamectin-benzoate, lepimectin and milbemectin.

(7) Juvenile hormone mimics, such as, for example, juvenile hormone analogs, for example hydroprene, quinoprene and methoprene or phenoxycarb or pyriproxyphene.

(8) Various non-specific (multisite) inhibitors, such as for example alkyl halides, for example methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartaric emetic or methyl isocyanate generator, for example diazomet and metam.

(9) Modulators of chordotonal organs, for example pymetrozine or flonicamide.

(10) Mite growth inhibitors, for example clofentezine, hexythiazox and diflovidazine or ethoxazole.

(11) Microbial disruptors of the gut membrane of insects, such as for example Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis, Cry1Ac1, CryiAb Subspezies tenebrionis, Cry1Ac plant proteins CrylFa, Cry1A.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1.

(12) Mitochondrial ATP synthase inhibitors, such as ATP disruptors, such as for example diafenthiuron or organotin compounds, for example azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradiphon. (13) Decouplers of oxidative phosphorylation by alteration of the proton gradient, such as, for example, chlorofenapir, DNOC and sulfluramide.

(14) Nicotinic acetylcholine receptor channel blockers, such as, for example, bensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

(15) Chitin biosynthesis inhibitors, type 0, eg bistrifluron, chlorfluazuron, diflubenzuron, (15) Chitin synthesis inhibitors, type 0, such as eg bistrifluron, chlorfluazuron, diflubenzuron, flucicloxuron, flufumumuron, hexafluron, hexafluron lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

(16) Chitin synthesis inhibitors, type 1, such as, for example, buprofezin.

(17) Disruptors of ecdysis (in particular in Diptera, ie Diptera), such as for example cyromazine. (18) Ecdysone receptor agonists, such as for example chromafenozide, halofenozide, methoxyphenozide and tebufenozide.

(19) Octopamine receptor agonists, such as for example amitraz.

(20) Inhibitors of electron transport of microchondrial complex III, such as for example hydramethylnon or acequinocyl or fluacripirim.

(21) Mitochondrial complex I electron transport inhibitors, such as, for example, METI acaricides, for example phenazaquine, fenpyroximate, pyrimidiphene, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris). (22) Voltage-dependent sodium channel blockers, such as for example indoxacarb or metaflumizone. (23) Acetyl CoA carboxylase inhibitors, such as for example derivatives of tetronic and tetramic acid, for example spirodiclofen, spiromesifene and spirotetramate.

(24) Inhibitors of electron transport of mitochondrial complex IV, such as for example phosphines, for example aluminum phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides, calcium cyanide, potassium cyanide and sodium cyanide.

(25) Inhibitors of electron transport of mitochondrial complex II, such as for example derivatives of beta-keto nitrile, for example cienopyraphene and cyflumetofen and carboxanilides, such as for example piflubumide. (28) Modulators of the ryanodine receptor, such as for example diamides, for example chlorantraniliprole, cyantraniliprole and flubendiamide,

other active substances, for example afidopiropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, biphenazate, broflanilide, bromopropylate, quinomethionate, chloropralethrin, cryolite, cyclanyliprole, cycloxaprid, cyhalodiamide, dichloromezothiapsiline, dichloromezothiapsiline, dichloromezothiapsiline, dicofluonolyzine, dichloromezothiazine, dicofluonolyzine flufenerim, flufenoxistrobina, flufiprol, fluhexafon fluopyram, fluralaner, fluxametamida, fufenozida, guadipir, heptaflutrina, imidaclotiz, iprodione, bifenthrin kappa, tefluthrin kappa, lotilaner, meperflutrina, paichongding, pyridalyl, pirifluquinazon, piriminostrobina, espirobudiclofen, tetrametilflutrina, tetraniliprol, tetraclorantraniliprol, thioxazafen, thiofluoximate, triflumezopyrim, and iodomethane; additionally preparations based on Bacillus firmus (I-1582, BioNeem, Votivo), and the following compounds: 1- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} -3 - (trifluoromethyl) -1H-1,2,4-triazol-5-amine (known from WO2006 / 043635) (CAS 885026-50-6), {1 '- [(2E) -3- (4- chlorophenyl) prop-2-en-1-yl] -5-fluorospiro [indole-3,4'-piperidine] -1 (2H) -yl} (2-chloropyridin-4-yl) methanone (known from WO2003 / 106457) (CAS 637360-23-7), 2-chloro-N- [2- {1 - [(2E) -3- (4-chlorophenyl) prop-2-en-1-yl] piperidin-4- yl} -4- (trifluoromethyl) phenyl] isonicotinamide (known from W o 2006/003494) (Ca S 872999-66-1), 3- (4-chloro-2,6-dimethylphenyl) -4-hydroxy- 8-methoxy-1,8-diazaspiro [4.5] dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3- (4-chloro-2,6 ethylcarbonate -dimethylphenyl) -8-methoxy-2-oxo-1,8-diazaspiro [4.5] dec-3-en-4-yl (known from EP 2647626) (CAS-1440516-42-6), 4- ( but-2-yn-1-yloxy) -6- (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (co known from WO2004 / 099160) (Ca S 792914-58-0), PF1364 (known from JP2010 / 018586) (CAS Reg.No. 1204776-60-2), N - [(2E) -1 - [(6-chloropyridin-3-yl) methyl] pyridin-2 (1H) -ylidene] -2,2,2-trifluoroacetamide (known from document WO2012 / 029672) (CAS 1363400-41-2), (3E) -3- [1 - [(6-chloro-3-pyridyl) methyl] -2-pyridylidene] -1,1,1-trifluoropropan-2- one (known from WO2013 / 144213) (C ^to S 1461743 15-6), N- [3- (benzylcarbamoyl) -4-chlorophenyl] -1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) - 1H-pyrazole-5-carboxamide (known from WO2010 / 051926) (Ca S 1226889-14-0), 5-bromo-4-chloro-N- [4-chloro-2-methyl-6- (methylcarbamoyl) phenyl] -2- (3-chloro-2-pyridyl) pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4- [5- (3,5-dichlorophenyl) -4, 5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (cis-1-oxide-3-thietanyl) benzamide, 4- [5- (3,5-dichlorophenyl) -4.5 -dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (trans-1-oxide-3-thietanyl) benzamide and 4 - [(5S) -5- (3,5-dichlorophenyl) - 4,5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (cis-1-oxide-3-thietanyl) benzamide (known given by w O 2013/050317 A1) (CAS 1332628-83-7), N- [3-chloro-1 - (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3- [(3,3,3-trifluoropropyl) sulfinyl] propanamide, (+) - N- [3-chloro-1- (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [( 3,3,3-trifluoropropyl) sulfinyl] propanamide and (-) - N- [3-chloro-1- (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [(3, 3,3-trifluoropropyl) sulfinyl] propanamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1) (CAS 1477923-37-7), 5 - [[(2E) -3 -chloro-2-propen-1-yl] amino] -1- [2,6-dichloro-4- (trifluoromethyl) phenyl] -4 - [(trifluoromethyl) sulfinyl] -1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (c As 1105672-77-2), 3-bromo-N- [4-chloro-2-methyl-6 - [(methylamino) thioxomethyl] phenyl] -1- (3-chloro-2 -pyridinyl) -1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N- [4-chloro-2 - [[(1,1-dimethylethyl) amino] carbonyl] -6-methylphenyl] -1- (3-chloro-2-pyridinyl) -3- (fluoromethoxy) -1H-pyrazole- 5-carboxamide (known from WO 2012/034403 A1) (CAS 1268277-22-0), N- [2- (5-amino-1,3,4-thiadiazol-2-yl) -4-chloro- 6-methylphenyl] -3-bromo-1- (3-chloro-2-pyridinyl) -1H-pyrazole-5-carboxamide (known from WO 2011/085575 A1) (CAS 1233882-22-8), 4- [3- [2,6-didoro-4 - [(3,3-didoro-2-propen-1-yl) oxy] phenoxy] propoxy] -2-methoxy-6- (trifluoromethyl) pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6); (2E) - and 2 (Z) -2- [2- (4-cyanophenyl) -1- [3- (trifluoromethyl) phenyl] ethylidene] -N- [4- (difluoromethoxy) phenyl] hydrazinecarboxamide (known from document Cn 101715774 A) (CAS 1232543-85-9); 3- (2,2-dichloroethenyl) -2,2-dimethyl-4- (1H-benzimidazol-2-yl) phenyl ester of cyclopropanecarboxylic acid (known from CN 103524422 A) (CAS 1542271-46-4); (4aS) -7-Chloro-2,5-dihydro-2 - [[(methoxycarbonyl) [4 - [(trifluoromethyl) thio] phenyl] amino] carbonyl] indeno [1,2-e] [1 , 3,4] oxadiazine-4a (3H) -carboxylic (known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-1- [N- [4- [1- [4- (1,1,2,2,2-pentafluoroethoxy) phenyl] - 1H-1,2,4-triazol-3-yl] phenyl] carbamate] -aL-mannopyranose (known from US 2014/0275503 A1) (CAS 1181213-14-8); 8- (2-cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (CAS 1253850-56-4), (8-anti) -8- (2-cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (CAS 933798-27-7), (8-sin) -8- (2 -cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8) and N- [3-chloro-1- (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [(3,3,3-trifluoropropyl) thio] propanamide (known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9).

Fungicides

The active principles specified in the present invention by their common name are known and are described, for example, in "Pesticide Manual" (Ed. Number 16 British Crop Protection Council) or can be searched on the Internet (for example: http: //www.alanwood.net/pesticides).

All the mixture components mentioned in classes (1) to (15), as the case may be, can form salts with suitable bases or acids if they are able to do so on the basis of their functional groups. All the fungicidal mixture components mentioned in classes (1) to (15), as the case may be, can include the tautomeric forms.

1) Ergosterol biosynthesis inhibitors, for example (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidine, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquiniconazole , (1,009) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazol, (1,016) prochloraz, (1,017) propiconazole, (1,018 ) prothioconazole, (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) tebuconazole, (1,022) tetraconazole, (1,023) triadimenol, (1,024) tridemorph, (1,025) triticonazole, (1,026) (1R, 2S, 5S) -5 - (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1,027) (1S, 2R, 5R) -5- ( 4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1,028) (2R) -2- (1-chlorocyclopropyl) -4 - [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol (1,029) (2R) -2- (1-chlorocyclopropyl) - 4 - [(1S) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triaz ol-1-yl) butan-2-ol, (1,030) (2R) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazole -1-yl) propan-2-ol, (1,031) (2S) -2- (1-chlorocyclopropyl) -4 - [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4 -triazol-1-yl) butan-2-ol, (1,032) (2s) -2- (1-chlorocyclopropyl) -4 - [(1S) -2,2-dichlorocyclopropyl] -1- (1H-1,2 , 4-triazol-1-yl) butan-2-ol, (1,033) (2S) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2, 4-triazol-1-yl) propan-2-ol, (1,034) (R) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazole- 4-yl] (pyridin-3-yl) methanol, (1,035) (S) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazole-4 -yl] (pyridin-3- yl) methanol, (1,036) [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridine -3-yl) methanol, (1,037) 1 - ({(2R, 4S) -2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-1,3-dioxolan-2-yl } methyl) -1H-1,2,4-triazole, (1,038) 1 - ({(2S, 4S) -2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-1, 3-dioxolan-2-yl} methyl) -1H-1,2,4-triazole, (1,039) 1 - {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) thiocyanate) or xiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl, (1040) thiocyanate 1 - {[rel (2R, 3R) -3- (2-chlorophenyl) -2- ( 2,4-Difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl, (1,041) 1 - {[rel (2R, 3s) -3- (2- chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl, (1,042) 2 - [(2R, 4R, 5R) -1 - (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1,043) 2 - [(2R, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4 -triazole-3-thione, (1,044) 2 - [(2R, 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2, 4-dihydro-3H-1,2,4-triazole-3-thione, (1,045) 2 - [(2R, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6, 6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1,046) 2 - [(2S, 4R, 5R) -1- (2,4- dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1,047) 2 - [(2S, 4R , 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione , (1,048) 2 - [(2S , 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3 -thiona, (1,049) 2 - [(2S, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro- 3H-1,2,4-triazole-3-thione, (1,050) 2- [1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2.4 -dihydro-3H-1,2,4-triazole-3-thione, (1,051) 2- [2-chloro-4- (2,4-dichlorophenoxy) phenyl] -1- (1H-1,2,4- triazol-1 -yl) propan-2-ol, (1,052) 2- [2-chloro-4- (4-chlorophenoxy) phenyl] -1- (1H-1,2,4-triazol-1-yl) butan -2-ol, (1,053) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1,054) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) pentan-2-ol, (1,055) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) propan-2-ol, (1,056) 2 - {[3- ( 2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1,057) 2 - {[ rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3 -tiona, (1.05 8) 2 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2 , 4-triazol-3-thione, (1,059) 5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, ( 1,060) 5- (allylsulfanyl) -1 - {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole, (1,061 ) 5- (allylsulfanyl) -1 - {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2, 4-triazole, (1,062) 5- (allylsulfanyl) -1 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} - 1H-1,2,4-triazole, (1,063) N '- (2,5-dimethyl-4 - {[3- (1,1,2,2-tetrafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl -N-methylimidoformamide, (1,064) N '- (2,5-dimethyl-4 - {[3- (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1,065 ) N '- (2,5-dimethyl-4 - {[3- (2,2,3,3-tetrafluoropropoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1,066) N' - (2.5 -dimethyl-4 - {[3- (pentafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1,067) N '- (2,5-dimethyl-4- {3 - [(1,1 , 2,2-tetrafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1,068) N '- (2,5-dimethyl-4- {3 - [(2,2,2-trifluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1,069) N '- (2,5-dimethyl-4- {3 - [(2,2,3,3-tetrafluoropropyl) sulfanyl] phenoxy} phenyl ) -N-ethyl-N-methylimidoformamide, (1,070) N '- (2,5-dimethyl-4- {3 - [(pentafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1,071) N '- (2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylimidoformamide, (1,072) N' - (4 - {[3- (difluoromethoxy) phenyl] sulfanyl} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (1,073) N '- (4- {3 - [(difluoromethyl) sulfanyl] phenoxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (1,074) N' - [5-bromo-6- (2,3-dihydro-1H-inden-2-yloxy) -2-methylpyridin-3-yl] -N-ethyl-N-methylimidoformamide, (1,075) N '- {4 - [(4,5-dichloro-1,3-thiazol-2-yl) oxy] -2,5-dimethylphenyl} -N-ethyl-N-methylimidoformamide, (1,076) N- {5- bromo-6 - [(1R) -1- (3,5-difluorophenyl) ethoxy] -2- methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1,077) N- {5-bromo-6- [(1S) -1- (3,5-Difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1,078) N- {5-bromo-6 - [(cis- 4-isopropylcyclohexyl) oxy] -2-methylpyridin-3- yl} -N-ethyl-N-methylimidoformamide, (1,079) N- {5-bromo-6 - [(trans-4-isopropylcyclohexyl) oxy] -2-methylpyridine -3-yl} -N-ethyl-N-methylimidoformamide, (1,080) N '- {5-bromo-6- [1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N -ethyl-N-methylimidoformamide.

2) Inhibitors of the respiratory chain in complex I or II, for example (2,001) benzovindiflupir, (2,002) bixafen, (2,003) boscalid, (2,004) carboxin, (2,005) fluopyram, (2,006) flutolanil, (2,007) fluxapyroxad , (2,008) furametpyr, (2,009) isofetamid, (2,010) isopyrazam (1R, 4S, 9S antiepimeric enantiomer), (2,011) isopyrazam (1S, 4R, 9R antiepimeric enantiomer), (2,012) isopyrazam (antiepimeric racemate, 1RS, 4RS 9SR), (2,013) isopyrazam (mixture of 1RS, 4SR, 9RS sinepimeric racemate and 1RS, 4SR, 9SR antiepimeric racemate), (2,014) isopyrazam (1R, 4S, 9R sinepimeric enantiomer), (2,015) isopyrazam (1S sinepimeric enantiomer , 4R, 9S), (2,016) isopyrazam (sinepimeric racemate 1RS, 4SR, 9RS), (2,017) penflufen, (2,018) penthiopyrad, (2,019) pidiflumetofen, (2,020) pyraziflumid, (2,021) sedaxane, (2,022) 1, 3-dimethyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2,023) 1,3-dimethyl-N- [ (3R) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2,024) 1,3-dimethyl-N - [(3S) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2,025) 1-methyl -3- (trifluoromethyl) -N- [2 '- (trifluoromethyl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (2,026) 2-fluoro-6- (trifluoromethyl) -N- (1,1 , 3-trimethyl-2,3-dihydro-1H-inden-4-yl) benzamide, (2,027) 3- (difluoromethyl) -1-methyl-N- (1,1,3-trimethyl-2,3-dihydro -1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2,028) 3- (difluoromethyl) -1-methyl-N - [(3R) -1,1,3-trimethyl-2,3- dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2,029) 3- (difluoromethyl) -1-methyl-N - [(3S) -1,1,3-trimethyl-2,3 -dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2,030) 3- (difluoromethyl) -N- (7-fluoro-1,1,3-trimethyl-2,3-dihydro- 1H-inden-4-yl) -1-methiMH-pyrazole-4-carboxamide, (2,031) 3- (difluoromethyl) -N - [(3R) -7-fluoro-1,1,3-trimethyl-2,3 -dihydro-1H-inden-4-yl] -1-methyl-1H-pyrazole-4-carboxamide, (2,032) 3- (difluoromethyl) -N - [(3S) -7-fluoro-1,1,3- trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H-pyrazole-4-carboxamide, (2,033) 5,8-difluoro-N- [2- (2-fluoro-4- {[4- (tri fluoromethyl) pyridin-2-yl] oxy} phenyl) ethyl] quinazolin-4-amine, (2,034) N- (2-cyclopentyl-5-fluorobenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1 -methyl-1H-pyrazole-4-carboxamide, (2,035) N- (2-tert-butyl-5-methylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole- 4-carboxamide, (2,036) N- (2-tert-butylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,037) N- (5 -chloro-2-ethylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methiMH-pyrazole-4-carboxamide, (2,038) N- (5-chloro-2-isopropylbenzyl) -N-cyclopropyl -3- (difluoromethyl) -5-fluoro-1-methiMH-pyrazole-4-carboxamide, (2,039) N - [(1R, 4S) -9- (dichloromethylene) -1,2,3,4-tetrahydro-1 , 4-methanonaphthalen-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2,040) N - [(1S, 4R) -9- (dichloromethylene) -1.2, 3,4-tetrahydro-1,4-methanonaphthalen-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2,041) N- [1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2,042) N- [ 2-chloro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,043) N- [3-chloro-2- fluoro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,044) N- [5-chloro-2- (trifluoromethyl ) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,045) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl -N- [5-methyl-2- (trifluoromethyl) benzyl] -1H-pyrazole-4-carboxamide, (2,046) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-fluoro-6- isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2,047) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropyl-5-methylbenzyl) -1-methyl-1H- pyrazole-4-carboxamide, (2,048) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carbothioamide, (2,049) N-cyclopropyl- 3- (Difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2,050) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- ( 5-fluoro-2-isopropylbenzyl) -1- methyl-1H-pyrazole-4-carboxamide, (2,051) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-4,5-dimethylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4 -carboxamide, (2,052) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-fluorobenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,053) N-cyclopropyl -3- (Difluoromethyl) -N- (2-ethyl-5-methylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,054) N-cyclopropyl-N- (2-cyclopropyl-5 -fluorobenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,055) N-cyclopropyl-N- (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2,056) N-cyclopropyl-N- (2-cyclopropylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole- 4-carboxamide.

3) Respiratory chain inhibitors in complex III, for example (3,001) methoctradine, (3,002) amisulbrom, (3,003) azoxystrobin, (3,004) coumethoxystrobin, (3,005) coumoxystrobin, (3,006) ciazofamide, (3,007) dimoxystrobine, (3,007) dimoxystrobine ) enoxastrobin, (3,009) famoxadon, (3,010) fenamidon, (3,011) flufenoxystrobin, (3,012) fluoxastrobin, (3,013) kresoxim-methyl, (3,014) methinostrobin, (3,015) orisastrobin, (3,016) picoxystrobin, (3,017) picoxystrobin, (3,017) picoxystrobin (3,018) pyrametostrobin, (3,019) pyroxystrobin, (3,020) trifloxystrobin (3,021) (2E) -2- {2 - [({[(1E) -1- (3 - {[(E) -1-fluoro-2 -phenylvinyl] oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylacetamide, (3,022) (2E, 3Z) -5 - {[1- (4-chlorophenyl) -1H -pyrazol-3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide, (3,023) (2R) -2 {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3,024) (2S) -2- {2 - [(2,5-dimethylphenoxy) methyl ] phenyl} -2-methoxy-N-methylacetamide, (3,025) 2-methylpropanoate of (3S, 6S, 7R, 8R) -8-benzyl-3 - [({3 - [(isobutyryloxy) methoxy] -4-methoxypyridine -2-yl} carbonyl) amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7-yl, (3,026) 2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3,027) N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formamide-2-hydroxybenzamide, (3,028) (2E, 3Z) -5 - {[1 - (4-doro-2-fluorophenyl) -1H-pyrazol-3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide.

4) Mitosis and cell division inhibitors, for example (4.001) carbendazim, (4.002) dietofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4,008) zoxamide, (4,009) 3-chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine, (4,010) 3-chloro-5- (4-chlorophenyl) -4- (2, 6-Difluorophenyl) -6-methylpyridazine, (4,011) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) pyridazine, (4,012) 4- (2-bromo-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,013) 4- (2-bromo-4-fluorophenyl) -N - (2-bromo-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,014) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4,015) 4- (2-bromo-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5 -amine, (4,016) 4- (2-bromo-4-fluorophenyl) -N- (2-chlorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,017) 4- (2-bromo- 4-fluorophenyl) -N- (2-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,018) 4- (2-chloro-4-fl uorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,019) 4- (2-chloro-4-fluorophenyl) -N- (2-chloro-6 -fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,020) 4- (2-chloro-4-fluorophenyl) -N- (2-chlorophenyl) -1,3-dimethyl-1H-pyrazole -5-amine, (4,021) 4- (2-chloro-4-fluorophenyl) -N- (2-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,022) 4- (4- chlorophenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine, (4,023) N- (2-bromo-6-fluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3- dimethyl-1H-pyrazol-5-amine, (4,024) N- (2-bromophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,025) N- (4-chloro-2,6-difluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine.

5) Compounds that have capacity for multisite activity, for example (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007 ) copper oxide, (5,008) copper oxychloride, (5,009) copper (2+) sulfate, (5,010) dithianon, (5,011) dodine, (5,012) folpet, (5,013) mancozeb, (5,014) maneb, (5,015 ) metiram, (5,016) zinc metiram, (5,017) copper oxine, (5,018) propineb, (5,019) sulfur and sulfur preparations including calcium polysulfide, (5,020) thiram, (5,021) zineb, (5,022) ziram.

6) Compounds capable of activating host defense, for example (6.001) acibenzolar-S-methyl, (6.002) isothianyl, (6.003) probenazole, (6.004) thiadinyl.

7) Inhibitors of amino acid and / or protein biosynthesis, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3- (5 -fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline.

(8) Inhibitors of ATP production, for example (8,001) silthiofam.

9) Inhibitors of cell wall synthesis, for example (9.001) benthiavalicarb, (9.002) dimethomorf, (9.003) flumorf, (9.004) iprovalicarb, (9.005) mandipropamide, (9.006) pirimorph, (9.007) valifenalate, (9.008) ) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one, (9.009) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one.

10) Inhibitors of lipid and membrane synthesis, for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

11) Melanin biosynthesis inhibitors, for example (11,001) tricyclazole, (11,002) 2,2,2-trifluoroethyl {3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl} carbamate.

12) Inhibitors of nucleic acid synthesis, for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxil), (12.003) metalaxyl, (12.004) metalaxyl-M (mephenoxam).

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

14) Compounds that can act as uncouplers, for example (14,001) fluazinam, (14,002) meptildinocap.

15) Other compounds, for example (15.001) abscisic acid, (15.002) benthiazole, (15.003) betoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) cufraneb, (15.008) cyflufenamide, (15.009 ) cymoxanil, (15,010) cyprosulfamide, (15,011) fluthianyl, (15,012) fosetyl-aluminum, (15,013) fosetyl-calcium, (15,014) fosetyl-sodium, (15,015) methyl isothiocyanate, (15,016) methaphenon, (15,017) mildew , (15,018) natamycin, (15,019) nickel dimethyldithiocarbamate, (15,020) nitrotal-isopropyl, (15,021) oxamocarb, (15,022) oxathiapiproline, (15,023) oxyphenthiine, (15,024) pentachlorophenol and salts, (15,025) phosphonic acid and its salts, (15,025) , (15,026) propamocarbphosethylate, (15,027) pyrophenone (clazafenone) (15,028) tebufloquin, (15,029) tecloftalam, (15,030) tolniphanide, (15,031) 1- (4- {4 - [(5R) -5- (2.6 -difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (15,032) 1- (4- {4 - [(5S) -5- (2,6-difluorophenyl ) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1 -yl) -2- [5-methyl-3- (trifluoromethyl) -1H -pyrazol-1-yl] ethanone, (15,033) 2- (6-benzylpyridin-2-yl) quinazoline, (15,034) 2,6-dimethyl-1H, 5H- [1,4] dithiino [2,3-c: 5,6-c '] dipyrrole-1,3, 5.7 (2H, 6H) -tetrone, (15,035) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- (5- [2- ( prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15,036 ) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- (5- [2-chloro-6- (prop-2-yn-1-yloxy ) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15,037) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {5- [2-fluoro-6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro -1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15,038) 2- [6- (3-fluoro-4-methoxyphenyl) -5- methylpyridin-2-yl] quinazoline, (15,039) 2 - {(5R) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4 -yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-dorophenyl methanesulfonate, (15,040) 2 - {(5S) -3- [ 2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro- 1,2-oxazol-5-yl} -3-dorof enyl methanesulfonate, (15,041) 2- {2 - [(7,8-difluoro-2-methylquinolin-3-yl) oxy] -6-fluorophenyl} propan-2-ol, (15,042) 2- {2-fluoro- 6 - [(8-fluoro-2-methylquinolin-3-yl) oxy] phenyl} propan-2-ol, (15,043) 2- {3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-dorophenyl methanesulfonate , (15,044) 2- {3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4 -yl] -4,5-dihydro-1,2-oxazol-5-yl} phenyl methanesulfonate, (15,045) 2-phenylphenol and its salts, (15,046) 3- (4,4,5-trifluoro-3,3 -dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15,047) 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15,048) 4- amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2 (1H) -one), (15,049) 4-oxo-4 - [(2-phenylethyl) amino] butyric acid, ( 15,050) 5-amino-1,3,4-thiadiazole-2-thiol, (15,051) 5-chloro-N'-phenyl-N '- (prop-2-yn-1-yl) thiophene 2-sulfonohydrazide, (15,052) 5-fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidi n-4-amine, (15,053) 5-fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, (15,054) 9-fluoro-2,2-dimethyl-5- (quinolin-3-yl ) -2,3-dihydro-1,4-benzoxazepine, (15,055) {6 - [({[(Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) but-3-yn-1-yl methyl] pyridin-2-yl} carbamate, (15,056) (2Z) -3-amino-2-cyano-3-phenylacrylate, ethyl (15,057) phenazine-1-carboxylic acid , (15,058) propyl 3,4,5-trihydroxybenzoate, (15,059) quinolin-8-ol, (15,060) quinolin-8-ol sulfate (2: 1), (15,061) {6 - [({[( Tert-butyl 1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate.

Biological pesticides as mixing components

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

Biological pesticides include in particular bacteria, fungi, yeasts, plant extracts, and products of this type, which are formed by microorganisms including proteins and secondary metabolic products.

Biological pesticides encompass bacteria such as sporogenic bacteria, bacteria that colonize roots, and bacteria that act as biological isecticides, fungicides, or nematicides.

Examples of bacteria of this type, which are used or can be used as biological pesticides, are:

Bacillus amiloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM I-1562 or Bacillus firmus, strain I-1582 (CNCM registration number I-1582) or Bacillus pumilus, in particular strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, in particular strain GB03 (Accession No. At CC SD-1397), or Bacillus subtilis strain QST713 (registration no. NRRL B-21661) or Bacillus subtilis strain OST 30002 (registration no. NRRL B-50421) Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 ( ATCC Accession No. 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode) -PR3 (ATCC accession number SD-5834), Streptomyces microflavus strain AQ6121 (= Qr D 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (accession number NRRL 30232).

Examples of fungi and yeasts, which are used or can be used as biological pesticides, are:

Beauveria bassiana, in particular strain ATCC 74040, Coniothyrium minitans, in particular strain CON / M / 91-8 (registration no. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known such as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (neu: Isaria fumosorosea, IFPC 2006), in particular 2006 or Apopka 97 strain (ATCC registration number 20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular V117b strain, Trichoderma atroviride, in particular SC1 strain (CBS registration number 122089 ), Trichoderma harzianum, in particular T. harzianum rifai T39. (CNCM registration number 1-952).

Examples of viruses that are used or can be used as biological pesticides are:

Adoxophyes orana (apple peel worm) granulovirus (GV), Cydia pomonella (apple worm) granulovirus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua ( armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV, Spodoptera littoralis (African black donut) NPV.

Also covered are bacteria and fungi, which are added as "inoculant" plants or plant parts or plant organs and through their special properties promote plant growth and plant health. Examples are:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosppum. Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., In particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products of this type, which were formed by microorganisms including proteins and secondary metabolic products, which are used or can be used as biological pesticides, are:

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 quinaa extract) Pyrethrum / Pyrethrin, 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 from Brassicaceae, in particular rape or mustard powder.

Protectors as mixing components

The compounds of formula (I) can be combined with protectants, such as for example benoxacor, cloquintocet (-mexyl), cyometrinyl, cyprosulfamide, diclormid, fenchlorazol (-ethyl), fenchlorim, flurazol, fluxofenim, furylazole, isoxadifene (-ethyl), mephenpyr (-diethyl), naphthalic anhydride, oxabetrinyl, 2-methoxy-N - ({4 - [(methylcarbamoyl) amino] phenyl} sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) -1-oxa -4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (CAS 52836-31-4).

Plants and plant parts

In accordance with the invention, all plants and plant parts can be treated. By plants are understood in this sense all plants and plant populations such as wild plants or desired and unwanted crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye , oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans Brassica olerácea (for example cabbage) and other species of vegetables , cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes). The crop plants can be plants that can be obtained by conventional phytogenetics and optimization procedures or by biotechnological and genetic engineering procedures or combinations of these procedures, including transgenic plants and including varieties of plants that can be protected or that cannot be protected. they can protect by plant variety rights. Plants are understood to be all stages of development, young (immature) plants to mature plants. By parts of plants should be understood all the aerial and subterranean parts and organs of the plants, such as bud, leaf, flower and root, exposing by way of example leaves, needles, stems, trunks, flowers, fruiting bodies, fruits and seeds as well as roots, bulbs and rhizomes. The plant parts also include harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, layers and seeds.

The treatment according to the invention of the plants and plant parts with the compounds of formula (I ') takes place directly or by action on the environment, habitat or storage space according to the usual treatment procedures, for example by immersion , sprayed, in particular in the case of seeds, also by simple or multilayer casings.

As already mentioned, according to the invention, all plants and their parts can be treated. In a preferred embodiment, types of plants and varieties of wild plants or obtained by conventional biological phytogenetic procedures, such as crossing or fusion of protoplasts, as well as their parts, are treated. In a further preferred embodiment, transgenic plants and plant varieties obtained by genetic engineering procedures are treated, optionally in combination with conventional procedures ( Genetically Modified Organisms ) and their parts. The term "parts" or "parts of plants" or "parts of plants" has been explained above. In a particularly preferred manner, according to the invention, plants of the plant varieties in each case commercially available or in use are treated. By plant varieties we mean plants with new properties ("traits"), which have been obtained either by conventional cultivation, by mutagenesis or by recombinant DNA techniques. These can be varieties, races, biotypes and genotypes.

Transgenic plants, seed treatment and integration events

Preferred plants or varieties of transgenic plants (obtained by genetic engineering) to be treated according to the invention include all the plants that have obtained genetic material by genetic engineering modification, which gives these plants properties ("traits ”) Valuable especially advantageous. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or salinity in water or soil, higher flowering yield, simplification of harvest, acceleration of maturation, higher harvest yields, higher quality and / or higher nutritional value of harvest products, better storage capacity and / or processability of harvest products. Other, and especially prominent, examples of such properties are an increased defense capacity of plants against animal and microbial parasites, such as insects, arachnids, nematodes, mites, snails, caused for example by toxins generated in plants, especially those that are generated by the genetic material of Bacillus thuringiensis (for example, by the genes CryIA (a), CryIA (b), CryIA (c), CrylIA, CrylIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations ) in plants, also a high defense capacity of plants against phytopathogenic fungi, bacteria and / or viruses, caused for example by systemic acquired resistance (SAR), sistemin, phytoalexin, elicitors as well as resistance genes and expressed proteins and toxins correspondingly, as well as an increased tolerance of plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosates or phosphinothricin (for example "PAT" gene). Genes which respectively confer the desired properties ("traits") can also be present in combinations with each other in transgenic plants. As examples of transgenic plants, important crop plants are mentioned, such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other species of vegetables. , cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes), especially corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed. Properties ("traits") include the high defense capacity of plants against insects, arachnids, nematodes and snails.

Plant protection - types of treatment

The treatment of plants and plant parts with the compounds of formula (I) takes place directly or by action on their environment, habitat or storage space according to the usual treatment procedures, for example, by immersion, spraying, spraying, irrigation , evaporation, atomization, fogging, spreading, foaming, propagation, spreading, injection, pouring (soaking), drip irrigation and, in the case of propagation material, in particular in the case of seeds, further by application as a coating on dry, wet disinfection, suspension disinfection, fouling, single or multi-layer wrapping, etc. It is also possible to spread the compounds of formula (I) according to the ultra-low volume method or inject the application form or the compound of formula (I) itself into the soil.

A preferred direct treatment of the plants is the application to the leaves, that is to say the compounds of formula (I) are applied to the foliage, the frequency of treatment and the amount of application having to be adapted to the infestation of the respective pest.

In the case of active principles that act systemically, the compounds of formula (I) also reach the plants via the roots. The treatment of the plants then takes place by the action of the compounds of formula (I) on the plant habitat. This can be for example by soaking, mixing in soil or nutrient solution, i.e. the plant location (e.g. soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I), or by the application on the ground, that is to say the compounds of formula (I) according to the invention are introduced in solid form, (for example in the form of a granulate) at the site of the plants. In the case of rice paddy crops, this can also be by dosing the compound of formula (I) in a solid application form (for example as granules) in a flooded rice field.

Seed treatment

Combating animal pests by treating plant seeds has been known for a long time and is under continuous improvement. However, in the case of seed treatment, there are a number of problems that cannot always be solved satisfactorily. Thus, it is desirable to develop procedures to protect the seeds and the germinating plant that make superfluous or at least considerably reduce the additional application of pesticides in storage, after sowing or after the emergence of the plants.

Furthermore, it is desirable to optimize the amount of the active ingredient used so that the seed and the germinating plant protect themselves as best as possible against attack by animal pests, but without damaging the plant itself by the active ingredient used. In particular, seed treatment procedures should also include the intrinsic insecticidal or nematicidal properties of transgenic pest tolerant or resistant plants to achieve optimal protection of seed and germinating plants with minimal use of pesticides.

Therefore, the present invention also relates in particular to a method for protecting seeds and germinating plants before attack by pests, the seed being treated with one of the compounds of formula (I). The method according to the invention for the protection of seeds and germinating plants against the attack of pests also comprises a method, in which the seed is treated simultaneously in a process or sequentially with a compound of formula (I) and component of mixture. This also comprises a process in which the seed is treated at different times with a compound of formula (I) and a mixture component.

Likewise, the invention relates to the use of the compounds of formula (I) for the treatment of seeds for the protection of the seed and the plant that is generated from it against animal pests.

Furthermore, the invention relates to the seed that was treated for protection against animal pests with a compound of formula (I). The invention also relates to seeds that were treated at the same time with a compound of formula (I) and a mixture component. The invention further relates to seeds that were treated at different times with a compound of formula (I) and mixing component. In the case of seeds that were treated at different times with a compound of formula (I) and mixture component, the individual substances may be present in different layers on the seed. In this connection, the layers containing a compound of formula (I) and a mixture component can optionally be separated by an intermediate layer. The invention also relates to seeds in which a compound of formula (I) and mixture component are applied as a constituent of a shell or as an additional layer or additional layers in addition to a shell.

Furthermore, the invention relates to seeds that after treatment with a compound of formula (I) are subjected to a filmcoating process, to prevent dust wear on the seeds.

One of the advantages that arise when a compound of formula (I) acts systemically is that the treatment of the seed not only protects the seed itself, but also the plants that result from it after emergence against to animal pests. In this way, immediate crop treatment can be discontinued at planting time or shortly thereafter.

Another advantage is based on the fact that by treating the seeds with a compound of formula (I) the germination and emergence of the treated seed can be promoted.

Similarly, it is advantageous to consider that the compounds of formula (I) can also be used in particular in transgenic seeds.

The compounds of formula (I) can also be used in combination with signaling technology agents, whereby a better colonization with symbionts takes place, such as for example rhizobia, mycorrhizae and / or endoparasitic bacteria or fungi, and / or can be produces optimized nitrogen fixation.

The compounds of formula (I) are suitable for the protection of seeds of any variety of plants, which are used in agriculture, in the greenhouse, in forests or in gardening. In this regard, it concerns in particular cereal seeds (for example wheat, barley, rye, millet and oats), corn, cotton, soybeans, rice, potatoes, sunflower, coffee, tobacco, canola, rapeseed, beet (for example , sugar beets and fodder beets), peanuts, vegetables (for example tomato, cucumber, beans, cabbages, onion and lettuce), fruit plants, lawns and ornamental plants. Special importance is given to the treatment of the seed of cereals (such as wheat, barley, rye and oats), corn, soybeans, cotton, canola, rapeseed, vegetables and rice.

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

In the context of the present invention, the compound of formula (I) is applied to the seeds. Preferably, the seed is treated in a state in which it is so stable that no damage occurs during the treatment. Generally, seed treatment can be done at any time between harvest and sowing. Usually, seeds that had been separated from the plant and freed from spadix, pod, stems, shells, wool or fruit flesh are used. Thus, for example, seeds that have been harvested, cleaned and dried to a storable moisture content can be used. Alternatively, it is also possible to use seeds which after drying have been treated, for example with water and then re-dried, for example primer. In the case of rice seed material it is also possible to use seeds that have been soaked, for example in water up to a certain stage of the rice embryo ("pigeon breast stage"), whereby germination and emergence are stimulated. more uniform.

Generally, during the treatment of the seed it has to be taken into account that the amount of the compound of formula (I) and / or other additives applied on the seed is selected in such a way that the germination of the seed is not impaired or the seed is not damaged. plant that arises from it. This has to be taken into account, above all, in the case of active principles that can show phytotoxic effects in certain application doses.

The compounds of formula (I) are generally applied in the form of a suitable formulation to the seeds. Suitable formulations and procedures for treating seeds are known to those skilled in the art.

The compounds of formula (I) can be transferred into common disinfectant formulations, such as solutions, emulsions, suspensions, powders, foams, pastes or seed wrap masses, as well as ULV formulations.

These formulations are prepared in a known manner, the compounds of formula (I) being mixed with customary additives, such as, for example, customary extenders as well as solvents or diluents, colorants, humectants, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, glues, gibberellins and also water.

As colorants that can be contained in the disinfectant formulations that can be used according to the invention, all customary colorants for such purposes are taken into account. Both poorly water-soluble polymers and water-soluble dyes can be used here. Examples are the dyes known under the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1.

As humectants that can be contained in the disinfectant formulations that can be used according to the invention, all the substances that promote wetting, common for the formulation of agrochemical active ingredients, are taken into account. Alkylnaphthalene sulfonates, such as diisopropyl- or diisobutylnaphthalene sulfonates, may preferably be used.

As dispersants and / or emulsifiers, which can be contained in the disinfectant formulations that can be used according to the invention, all customary nonionic, anionic and cationic dispersants for the formulation of agrochemical active ingredients are taken into account. Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants can preferably be used. As suitable nonionic dispersants there are in particular mentioned ethylene oxide-propylene oxide block polymers, alkylphenolpolyglycol ether as well as tristryrylphenolpolyglycol ether and their phosphated or sulphated derivatives. Suitable anionic dispersants are in particular lignin sulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.

The antifoam agents used in the disinfectant formulations which can be used according to the invention may contain all the antifoam substances customary for the formulation of agrochemical active ingredients. Preferably silicone defoamers and magnesium stearate can be used.

As preservatives, all substances that can be used for such purposes in agrochemicals can be present in the disinfectant formulations that can be used according to the invention. By way of example, dichlorophene and benzyl alcohol hemiformal are mentioned.

As secondary thickeners that can be contained in the disinfectant formulations that can be used according to the invention, all substances that can be used for such purposes in agrochemicals are taken into account. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly dispersed silicic acid are preferably taken into account.

As adhesives, which can be contained in the disinfectant formulations that can be used according to the invention, all common binders that can be used in disinfectants are taken into account. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose are preferably mentioned.

As gibberellins, which can be contained in the disinfectant formulations that can be used according to the invention, the gibberellins A1, A3 (= gibberellic acid), A4 and A7 are preferably used, particularly preferably gibberellic acid is used. . Gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz-und Schadlingsbekampfungsmittel", vol. 2, Springer Verlag, 1970, pages 401-412).

The disinfectant formulations that can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seeds of the most diverse species. In this way, the concentrates or the preparations that can be obtained from them by dilution with water can be used for the disinfection of the seed of cereals, such as wheat, barley, rye, oats and triticale, as well as the seed of corn, rice, rapeseed, peas, beans, cotton, sunflower, soybeans and turnip or also vegetable seeds of the most diverse nature. The disinfectant formulations that can be used according to the invention or their diluted application forms can also be used for the disinfection of seeds of transgenic plants.

For the treatment of seeds with the disinfectant formulations that can be used according to the invention or application forms prepared therefrom by adding water, all mixing devices that can be used customarily for disinfection are taken into account. In detail, the disinfection proceeds so that the seeds are added to a mixer in discontinuous or continuous operation, the desired amount is added in each case to the disinfectant formulations either as such or after prior dilution with water and mix until uniform distribution over the seed. If necessary, this is followed by a drying process.

The amount of application of disinfectant formulations that can be used in accordance with the invention can be varied within a wide range. It depends on the respective content of the compounds of formula (I) in the formulations and on the seed. The application amounts in the case of the compound of formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.

Animal health

In the field of animal health, ie the field of veterinary medicine, the compounds of formula (I) are effective against animal parasites, in particular ectoparasites or endoparasites. The term endoparasite encompasses in particularly helminths and protozoa such as coccidia. Ectoparasites are usually and preferably arthropods, in particular insects or mites.

In the field of veterinary medicine, the compounds of formula (I) that have a favorable toxicity against warm-blooded animals, to combat parasites that appear in animal husbandry and in livestock breeding in useful animals, studs, animals zoo, laboratory animals, test animals and domestic animals. These are effective against all or each one of the development stages of the parasites.

Useful agricultural animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer, and in particular cattle and pigs; poultry such as turkeys, ducks, geese and in particular chickens; fish or crustaceans, for example in aquaculture or, where appropriate, insects such as bees.

Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and in particular dogs, cats, caged birds, reptiles, amphibians or aquarium fish.

According to a certain embodiment, the compounds of formula (I) are administered to mammals.

According to a further determined embodiment, the compounds of formula (I) are administered to birds, in particular caged birds or in particular poultry.

Using the compounds of formula (I) to combat animal parasites will reduce or prevent disease, deaths and decreases in yield (in meat, milk, wool, hides, eggs, honey and the like), so that it is allowed cheaper and easier raising livestock and animal welfare can be achieved.

With regard to the field of animal health, the term "combat" or "combat", means in the present context that by means of the compounds of formula (I) the appearance of the respective parasite is effectively reduced in an animal that is infected with parasites of this guy to a harmless extent. More precisely, "combat" in the present context, means that the compounds of formula (I) destroy the respective parasites, prevent their growth or prevent their multiplication.

Arthropods include, for example, but not limited to,

from the order Anoplurids, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .;

from the order malophagids and suborders amblyceros and ischnoceros, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematoceros and Braquíceros, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp. ., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp., Melophagus spp., Morellia spp., 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 .;

from the order Siphonaptera, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .;

from the order Heteroptera, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp .; as well as annoying insects and unsanitary pests of the order blataridae.

Furthermore, in the case of arthropods, the following mites may be mentioned by way of example, but not limited to it:

from the subclass mites (Acarina) and from the order Metastigmata, for example from the Argasidae family, such as Argas spp., Ornithodorus spp., Otobius spp., from the Ixodidae family, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. ., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genus of heteroxy ticks); from the order Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilaelaps spp., Varroa spp .; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Psoroptes spp. Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp.

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

Mastigophora (Flagellata), such as:

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

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

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

Sarcomastigophora (Rhizopoda), such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, for example Hartmanella sp.

Alveolata such as Apicomplexa (Sporozoa): for example 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, for example Hepatozoon spp., Klossiella spp .; from the order Haemosporida, for example Leucocytozoon spp., Plasmodium spp .; from the order Piroplasmida, for example Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp .; from the order Vesibuliferida, for example Balantidium spp., Buxtonella spp.

Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And further for example Myxozoa spp.

Helminths pathogenic to humans or animals include, for example, acantocephalus, nematodes, pentastoma, and flathelminths (for example, monogeneous, cestodes, and trematodes).

Examples of helminths include, but are not limited to:

monogeneous: for example: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .;

cestodes: from the order Pseudophyllidae, for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.

From the order of cyclophilids, for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinocotyle 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., Thysaniezia spp., Thysaniezia spp., Thysaniezia spp.

Trematodes: of the digene class 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., Fasciolides spp., Fasciolides spp., Fasciolides spp. ., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Oriochis spp. Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.

Nematodes: from the order Trichinellidae, for example: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.

From the order Tillenquids, for example: Micronema spp., Parastrangyloides spp., Strongyloides spp.

From the order rhabdoids, for example: 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., Phylaroid spp., Globocephalusium spp., Graphidchus spp. ., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagodontus spp., Oesophagodontus spp. Ollulanus spp .; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaídos spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protospptrongylus spp. ., Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Hookworm spp.

From the order Spiruridae, 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., Setariainema spp., Skjrabilaria spp., Setariainema spp. ., Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp.

Acanthocephalus: from the order Oligacanthorhynchida for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida, for example: Moniliformis spp.,

from the order polymorphids, for example: Filicollis spp .; from the order Echinorhynchida, for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: from the order porocephalic, for example Linguatula spp.

In the field of veterinary medicine and in livestock farming, the compounds of formula (I) are administered according to procedures generally known in the art, such as enteral, parenteral, dermal or nasal routes in the form of suitable preparations. . Administration can take place prophylactically, metaphylactically, or therapeutically.

Therefore, an embodiment of the present invention relates to the compounds of formula (I) for use as a drug.

A further aspect relates to the compounds of formula (I) for use as an anti-deworming agent.

A further special aspect of the invention relates to the compounds of formula (I) for use as an anthelmintic agent, in particular for use as a nematicide, pesticide against flatworms, pesticide against acantocephalus or pesticide against pentastomids.

A further special aspect of the invention relates to compounds of formula (I) for use as antiprotozoal agent.

A further aspect relates to the compounds of formula (I) for use as an anti-ectoparasitic agent, in particular an arthropodicide, very especially an insecticide or an acaricide.

Other aspects of the invention are veterinary drug formulations comprising an effective amount of at least one compound of formula (I) and at least one of the following: a pharmaceutically acceptable excipient (for example, solid or liquid diluents), a pharmaceutically acceptable auxiliary agent (eg surfactants), in particular a pharmaceutically acceptable excipient conventionally used in veterinary drug formulations and / or a pharmaceutically acceptable auxiliary agent conventionally used in veterinary drug formulations.

A related aspect of the invention is a process for the production of a veterinary medicinal formulation as described herein, comprising the step of mixing at least one compound of formula (I) with excipients and / or auxiliary agents pharmaceutically acceptable, in particular with pharmaceutically acceptable excipients conventionally used in veterinary drug formulations and / or auxiliary agents conventionally used in veterinary drug formulations.

Another special aspect of the invention are formulations of veterinary drugs selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoal and arthropodicidal formulations, very specially selected from the group of nematicidal formulations, antiplatelminths, formulations against acantocephalus, formulations against pentastomids, insecticides and acaricides, in accordance with the aforementioned aspects, and procedures for their production.

Another aspect relates to a method for the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites mentioned herein, by using an effective amount of a compound of the formula ( I) in an animal, in particular a non-human animal, that needs it.

Another aspect relates to a method for the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of ectoparasites and endoparasites mentioned herein, by using a veterinary drug formulation as defined in the present document in an animal, in particular in a non-human animal, that needs it.

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 herein, in an animal, in particular in a non-human animal.

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

In a certain embodiment, in this way, mixtures of at least one compound of formula (I) with other active principles, in particular with endo- and ectoparasiticides, are provided for the field of veterinary medicine.

In the field of animal health, "mixture" means not only that two (or more) different active ingredients are formulated in a common formulation and used correspondingly together, but also refers to products that comprise separate formulations for each active principle. Therefore, when more than two active principles are to be used, all the active principles can be formulated in a common formulation or all the active principles can be formulated in separate formulations; Equally conceivable are mixed forms in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow separate or successive application of the active ingredients in question.

The active substances specified in this document with their "common names" are known and described, for example, in the "Pesticide Manual" (see above) or can be searched on the Internet (for example: http: //www.alanwood .net / pesticides).

Exemplary active ingredients from the group of ectoparasiticides as mixing components, without this being intended to be a limitation, include the insecticides and acaricides expressly listed above. Other active ingredients that can be used are mentioned below according to the above-mentioned classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-gated chloride channel blockers; (3) sodium channel modulators; (4) competitive modulators of the nicotinic acetylcholine receptor (nAChR); (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-gated chloride channel (GluCl); (7) juvenile hormone mimetics; (8) other non-specific (multisite) inhibitors; (9) chordotonal organ modulators; (10) mite growth inhibitors; (12) mitochondrial ATP synthase inhibitors, such as ATP switches; (13) oxidative phosphorylation uncouplers by disruption of the proton gradient; (14) nicotinic acetylcholine receptor channel blockers; (15) chitin biosynthesis inhibitors, type 0; (16) chitin biosynthesis inhibitors, type 1; (17) mute switches (especially in Diptera); (18) ecdysone receptor agonists; (19) octopamine receptor agonists; (21) mitochondrial complex I electron transport inhibitors; (25) inhibitors of mitochondrial complex II electron transport; (20) inhibitors of mitochondrial complex III electron transport; (22) voltage-gated sodium channel blockers; (23) acetyl CoA carboxylase inhibitors; (28) ryanodine receptor modulators;

active substances that have unknown or non-specific mechanisms of action, for example fentriphanyl, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triaratene, clothiazoben, tetrasul, potassium oleate, petroleum, methoxadipliazone, brompropylate, cryolite; compounds of other classes, for example butacarb, dimethylan, cloethocarb, phosphocarb, pyrimiphos (-ethyl), parathion (-ethyl), methacryphos, isopropyl o-salicylate, trichlorfon, sulprofos, propafos, sebufos, pyridation, protoate, diclofention, demeton -S-methyl sulfone, isazophos, cyanophenophos, dialiphos, carbofenothion, autathiophos, aromfenvinphos (-methyl), azinphos (-ethyl), chlorpyrifos (-ethyl), phosmethylan, iodophenphos, dioxabenzophos, formothion, phonophos, flupirazophos; organochlorine compounds, for example camphechlor, lindane, heptachlor; or phenylpyrazoles, for example acetoprol, pyrafluprole, pyriprole, vaniliprole, sisapronil; or isoxazolines, for example sarolaner, afoxolaner, lotilaner, fluralaner; pyrethroids, for example (cis-, trans-) metofluthrin, profluthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin, RU15525, teralethrin, cis-resmethrin, heptafluthrin, bioethanethrine, cispermethrin, bio-permethrin, cispermethrin, biopermethrin, cispermethrin, bio-permethrin , clocitrin, cyhalothrin (lambda-), clovaportrin, or halogenated hydrocarbon compounds (HCHs),

neonicotinoids, for example nitiazine

dichloromezothiaz, triflumezopyrim

macrocyclic lactones, for example nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin oxime

triprene, epphenonane, diofenolan;

biological compounds, hormones or pheromones, for example natural products, for example thuringiensin, codlemone or components of Neem

dinitrophenols, for example dinocap, dinobuton, binapacryl;

benzoylureas, for example fluazuron, penfluron,

amidine derivatives, eg chlormebuform, cimiazol, demiditraz

Acaricides for the control of varroa in hives, for example organic acids, for example formic acid, oxalic acid.

Illustrative active ingredients from the group of endoparasiticides, as mixing components, include, but are not limited to, anthelmintic actives and antiprotozoal actives.

Anthelmintic active ingredients include, but are not limited to, the following nematicidal, trematocidal and / or cestocidal active ingredients:

from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin, milbemycin;

from the benzimidazole and probenzimidazole class, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netbimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole; flubendazole, albendazole; flubendazole

from the class of the depsipeptides, preferably cyclic depsipeptides, especially the 24-membered cyclic depsipeptides, for example: emodepside, PF1022A;

from the class of tetrahydropyrimidines, for example: morantel, pyrantel, oxantel;

from the class of the imidazothiazoles, for example: butamisol, levamisole, tetramisol;

from the aminophenylamidine class, for example: amidantel, deacylated amidantel (dAMD), tribenedimidine;

from the class of aminoacetonitriles, for example: monepantel;

from the class of the paraherquamides, for example: paraherquamida, derquantel;

from the class of salicylanilides, for example: tribromsalan, bromoxanide, brothianide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxanide;

from the class of substituted phenols, for example: nitroxynil, bithionol, disophenol, hexachlorophene, niclofolan, meniclofolan;

from the class of organophosphates, for example: trichlorfon, naphthalophos, dichlorvos / DDVP, crufomate, coumaphos, haloxon; from the class of piperazinones / quinolines, for example: praziquantel, epsiprantel;

from the class of piperazines, for example: piperazine, hydroxyzine;

from the class of tetracyclines, for example: tetracycline, chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline; of various other classes, for example: bunamidine, niridazole, resorantel, omphalothin, oltipraz, nitroscanate, nitroxynyl, oxamniquine, mirasan, miracil, lucanton, hicanton, hetolin, emetin, diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, beethepam.

Antiprotozoal active ingredients include, but are not limited to, the following active ingredients: from the triazine class, for example: diclazuril, ponazuril, letrazuril, toltrazuril;

from the class of the polyether ionophores, for example: monensin, salinomycin, Maduramycin, Narasin;

from the class of macrocyclic lactones, for example: milbemycin, erythromycin;

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

from the class of quinines, for example: chloroquine;

from the pyrimidine class, for example: pyrimethamine;

from the class of sulfonamides, for example: sulfaquinoxaline, trimethoprim, sulfaclozine;

from the class of thiamines, for example: amprolium;

from the class of lincosamides, for example: clindamycin;

from the class of carbanilides, for example: imidocarb;

from the class of nitrofurans, for example: nifurtimox;

from the class of quinazolinone alkaloids, for example: halofuginone;

of various other classes, for example: oxamniquine, paromomycin;

from the vaccine class or microorganism antigens, for example: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis canis Dictyocaulus viviparus.

All the mentioned mixing components, as the case may be, can also form salts with suitable bases or acids if they are able to do so on the basis of their functional groups.

Vector combat

The compounds of formula (I) can also be used in vector control. A vector in the sense of the present invention is an arthropod, in particular an insect or arachnid, which is capable of transmitting pathogens such as for example viruses, worms, unicellular organisms and bacteria from a reserve (plant, animal, human being, etc.) to a host. Pathogens can be transmitted either mechanically (eg Trachoma by flies that do not bite) to a host, or after injection (eg malaria parasites by mosquitoes) to a host.

Examples of vectors and the diseases or pathogens transmitted by them are:

1) mosquitoes

- Anopheles: malaria, Filariose;

- Culex: Japanese encephalitis, Filariasis, other viral diseases, transmission by other worms; - Aedes: yellow fever, Dengue fever, other viral diseases, Filariasis;

- Simulium: transmission by worms in particular Onchocerca volvulus;

- Psychodidae: transmission of leismaniasis

2) lice: skin infections, epidemic exanthematic typhus;

3) fleas: plague, endemic exanthematic typhus, tapeworms;

4) flies: sleeping sickness (trypanosomiasis); cholera, other bacterial diseases;

5) mites: acarosis, epidemic exanthematic typhus, rickettsiosis, tularemia, St. Louis encephalitis, Central European tick encephalitis (FSME), Crimean-Congo fever, borreliosis;

6) Ticks: Borreliosis such as Borrelia bungdorferi sensu lato, Borrelia duttoni, Central European encephalitis, Q fever (Coxiella burnetii), Babesias (Babesia canis canis), Ehrlichiosis.

Examples of vectors in the sense 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, lice, beetles, and nematodes.

Other examples of vectors in the sense of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (Malaria) and Culex , Psychodide such as Phlebotomus, Lutzomyia, lice, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.

A vector combat is also possible when the compounds of formula (I) break the resistance.

The compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens, which are transmitted by vectors. Therefore, another aspect of the present invention is the use of compounds of formula (I) for the control of vectors, for example in agriculture, in horticulture, in forests, in gardens and leisure facilities as well as in the protection of stored products and materials.

Protection of industrial materials

The compounds of formula (I) are suitable for the protection of industrial materials against attack or destruction by insects, for example of the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zigenthomes.

By industrial materials are understood in the present context non-living materials, such as preferably plastics, adhesives, glues, paper and cardboard, leather, wood, wood processing products and paints. The application of the invention for the protection of wood is especially preferred.

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

In another embodiment, the compounds of formula (I) are found as a ready-to-use pesticide, that is, they can be applied without further changes to the corresponding material. As additional insecticides or as fungicides, in particular those mentioned above are suitable.

Surprisingly, it was also discovered that the compounds of formula (I) can be used for the protection against the growth of vegetation of objects, in particular of boat hulls, screens, nets, buildings, docks and signaling installations, which come into contact with water. of sea or brackish water. Likewise, the compounds of formula (I) can be used alone or in combination with other active principles as anti-fouling agents.

Combat animal pests in the hygiene sector

The compounds of formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in the home protection, hygiene and stored products, mainly to combat insects, arachnids, ticks and mites, which exist in closed spaces, such as, for example, homes, industrial buildings, offices, cabins. of vehicles, animal husbandry facilities. To combat animal pests, the compounds of formula (I) are used alone or in combination with other active principles and / or auxiliary agents. They are preferably used in household insecticide products. The compounds of formula (I) are effective against sensitive and resistant species as well as against all stages of development.

These pests include, for example, pests of the class arachnids, of the orders scorpions, spiders and opilions, of the classes chilopods and diplopods, of the class insects the order Blatodeans, of the orders coleoptera, dermaptera, diptera, heteroptera, hymenoptera, isoptera , Lepidoptera, Ftiraptera, Psocoptera, Saltatorios or Orthoptera, Siphonaptera and Zigenthomes and of the class Malacostraca the order Isopoda.

The application takes place for example in aerosols, non-pressure sprays, for example pump and atomization sprays, nebulizers, mist formers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel evaporators and membrane, propellant-actuated evaporators, passive or non-powered evaporation systems, moth-proof papers, moth-proof sachets and moth-proof gels, such as granules or powders, in dispersal baits or bait stations.

Preparation examples

The following preparation and use examples illustrate the invention without limiting it. The products were characterized by 1H NMR spectroscopy and / or LC-MS (Liquid Chromatography - Mass Spectrometry).

The logP values were determined in accordance with OECD Guidelines 117 (EC Directive 92/69 / EEC) by HPLC (high-performance liquid chromatography) using phase columns. Reverse (RP) (C18), using the following procedures:

[a] LC-MS determination in the acidic range was carried out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (contains 0.1% formic acid) as mobile phases; linear gradient from 10% acetonitrile to 95% acetonitrile.

[b] LC-MS determination in the neutral range was carried out at pH 7.8 with 0.001 molar aqueous ammonium hydrogen carbonate solution and acetonitrile as mobile phases; linear gradient from 10% acetonitrile to 95% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) with known logP values (logP values were determined on the basis of retention times by linear interpolation between two alkanones successive).

NMR spectra were determined using a Bruker Avance 400 apparatus equipped with a flow probe head (60 µl volume). In individual cases, NMR spectra were measured with a Bruker Avance II 600.

NMR data for selected examples are shown in classical form (values 8, so-called "multiplet splitting" technique, number of hydrogen atoms). The separation of the signals was described as follows: s (singlet), d (doublet), t (triplet), q (quadruplet), quint (quintuplet), m (multiplet), br (for broad signals). The solvents used were CD3CN, CDCh or d6-DMSO, with tetramethylsilane (0.00 ppm) used as a reference.

Procedure A

Example: 2- (Methoxymethyl) -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-22)

0.20 g (1.2 mmol) of 2- (methoxymethyl) -1-methyl-1H-imidazole-5-carboxylic acid (V-1-22, Ex. 29, US2006 / 0019949 A1) was stirred at 5 ml of thionyl chloride at 80 ° C until the evolution of gas had stopped, they were concentrated, subjected to incipient dissolution twice with in each case 10 ml of toluene, concentrated, dissolved in a little tetrahydrofuran and added dropwise to a solution of 0.14 g (1.3 mmol) of 3-methylaminopyridine (VI-1) in 10 ml of pyridine at 0 ° C. The mixture was then stirred at room temperature for another 18 hours. The preparation was concentrated in vacuo and the residue was purified by reverse phase medium pressure (Rp) column chromatography with water / acetonitrile. After purification, 159 mg (51.9% of theory) were obtained.

logP [n]: 0.63;

1H NMR (CD3CN 400MHz); 8 = 3.26 (s, 3H), 3.39 (s, 3H), 3.78 (s, 3H), 4.40 (s, 2H), 6.20 (s, 1H), 7.34 -7.37 (m, 1H), 7.65-7.69 (m, 1H), 8.39-8.40 (d, 1H), 8.44-8.46 (m, 1H) ppm.

Procedure B-1

12.7 g (105 mmol) of thionyl chloride were added to a suspension of 12.0 g (95.2 mmol) of 1-methylimidazole-5-carboxylic acid (VII-1 -1) in 72 ml of toluene, and the mixture was stirred at 130 ° C overnight. The reaction mixture was concentrated in vacuo. A solution of 10.3 g (95.2 mmol) of 3-methylaminopyridine (VI-1) in 72 ml of pyridine was added to the residue, and the resulting reaction mixture was stirred at 115 ° C for 4 hours. This was followed by another concentration in vacuo. The residue was purified on silica gel by MPLC with the acetonitrile / methanol mobile phase. After purification, 8.1 g (39.3% of theory) were obtained.

logP [n] = 0.44;

1H NMR (CD 3 CN, 400MHz); 8 = 3.39 (s, 3H), 3.81 (s, 3H), 6.17 (s, 1H), 7.36-7.40 (m, 2H), 7.67-7.70 ( m, 1H), 8.41 (m, 1H), 8.47 (m, 1H) ppm.

Example: 2- (Hydroxymethyl) -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-7)

4.33 g (20 mmol) of N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (IX-1-1) and 1.8 g (60 mmol) were stirred of paraformaldehyde in 20 ml of acetonitrile together in a 50 ml autoclave at an argon pressure of 1000 kPa (10 bar) and 120 ° C for 48 hours. The solvent was evaporated. The residue was purified on silica gel by MPLC using the dichloromethane / methanol mobile phase. After purification, 2.7 g (54% of theory) were obtained. logP [n] = 0.28;

1 H NMR (CD 3 CN 400MHz); 8 = 3.39 (s 3H), 3.80 (s, 3H), 4.51 (s, 2H), 6.17 (s, 1H), 7.35-7.38 (m, 1H), 7.67-7.70 (m, 1H), 8.396-8.402 (d, 1H), 8.44-8.46 (m, 1H) ppm.

Example: 2- (Chloromethyl) -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (III-1-1)

2.3 g (9.34 mmol) of 2- (hydroxymethyl) -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-7) were placed in 2000 ml of methylene chloride, 1.48 g (18.7 mmol) of pyridine were added, 3.33 g (28 mmol) of thionyl chloride were added dropwise at 0 ° C and the mixture was stirred at temperature atmosphere at night. The mixture was concentrated in vacuo on a rotary evaporator and the residue was taken up in 10 ml of sodium bicarbonate solution and 20 ml of methanol and concentrated once more on a rotary evaporator. The residue was purified on silica gel by MPLC using the acetonitrile / methanol mobile phase. After purification 1.7 g (67% of theory) were obtained.

logP [n] = 0.89;

1 H NMR (CD 3 CN 400MHz); 8 = 3.50 (s, 3H), 3.94 (s, 3H), 5.10 (s, 2H), 7.18 (s, 1H), 7.91-7.95 (m, 1H) , 8.36-8.38 (m, 1H), 8.585-8.598 (d, 1H), 8.79-8.80 (d, 1H) ppm.

Example: 2 - [(Isopropylsulfanyl) methyl] -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-29)

114 mg (1.5 mmol) of 2-propanethiol (IX-29) and 0.185 mg (1.65 mmol) of potassium tert-butoxide were placed in 5 ml of acetonitrile and stirred briefly, and 265 mg ( 1.0 mmol) of 2- (chloromethyl) -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (III-1-1) at room temperature. The mixture was stirred for about 5 minutes and concentrated under reduced pressure and the residue was purified by reverse phase medium pressure (RP) column chromatography using water / acetonitrile. After purification, 26 mg (8.5% of theory) were obtained. logP [a] = 0.76; logP [n] = 1.50;

1 H NMR (CD 3 CN 400MHz); 8 = 1.17 (6H, d), 2.79 (m, 1H), 3.39 (s, 3H), 3.76 (s, 2H), 3.79 (s, 3H), 6.17 (s, 1H), 7.33-7.36 (m, 1H), 7.64-7.67 (m, 1H), 8.387-8.393 (d, 1H), 8.43-8.45 (m , 1H) ppm.

Procedure B-2

Example: 2 - [(Isopropylsulfonyl) methyl] -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-30)

0.127 g (0.42 mmol) of 2 - [(isopropylsulfanyl) methyl] -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-29) were introduced in 5 ml of methylene chloride, 0.16 ml of (2.1 mmol) of trifluoroacetic acid was added, the mixture was stirred briefly, and 0.257 g (1.04 mmol) of meta-chloroperbenzoic acid (approximately to 70%) at 0 ° C and stirring was continued under TLC control. Once no more starting material was detected, excess peroxide was destroyed, the preparation was concentrated in vacuo and the residue was purified by reverse phase medium pressure (RP) column chromatography with water / acetonitrile. After purification, 0.108 g (77% of theory) were obtained.

logP [a]: 0.56; logP [n]: 0.88;

1 H NMR (CD 3 CN, 400MHz): see Table 2.

Example: 2 - [(Isobutylsulfonyl) methyl] -N, 1-dimethyl-N- (1-oxidopyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-55)

2.90 g (9.11 mmol) of 2 - [(isobutylsulfanyl) methyl] -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1- 31) in 79.1 ml of methylene chloride, 3.51 ml of (45.5 mmol) trifluoroacetic acid was added, the mixture was stirred briefly, and 5.61 g (22.8 mmol) of meta -chloroperbenzoic (approximately 70%) at 0 ° C and stirring was continued under TLC control. Once no more starting material was detected, excess peroxide was destroyed, the preparation was concentrated in vacuo and the residue was purified by reverse phase medium pressure (RP) column chromatography with water / acetonitrile. After purification, 0.21 g (5.5% of theory) were obtained.

logP [a]: 0.68; logP [n]: 0.77;

1 H NMR (CD 3 CN, 400MHz): see Table 2.

Example: N, 1-Dimethyl-2- (1H-pyrazol-1-ylmethyl) -N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-43)

A solution of 84.9 mg (1.25 mmol) of IH-pyrazole (X-43) and 49.9 mg (1.25 mmol) of sodium hydride in 11.3 ml of N, N-dimethylformamide was stirred at 30 ° C for 10 minutes. 300 mg (1.13 mmol) of 2- (chloromethyl) -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (III-1-1) were added and stirred the solution at 60 ° C for 18 hours. The preparation was quenched with 2 ml of concentrated ammonium chloride solution and concentrated. The residue was purified on silica gel by MPLC using the acetonitrile / methanol mobile phase. After purification, 210 mg (62.5% of theory) were obtained.

logP [a]: 0.35; logP [n]: 0.81;

1H NMR (da-DMSO, 400MHz); 8 = 3.36 (s, 3H), 3.77 (s, 3H), 5.42 (s, 2H), 6.23-6.25 (m, 2H), 7.42-7.44 ( m, 2H), 7.70-7.71 (m, 1H), 7.825-7.845 (m, 1H), 8.46-8.47 (m, 1H), 8.480-8.484 (m, 1H) ppm.

Procedure C

Example: 2- (2-Hydroxypropan-2-yl) -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-10)

0.300 g (1.39 mmol) of N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (IX-1-1) was dissolved in 10 ml of THF and cooled until -90 ° C. During the reaction, the temperature was kept between -85 ° C and -90 ° C. At -90 ° C, 0.58 ml (1.45 mmol) of a 2.5 molar solution of n-BuLi in n-hexane was added dropwise over a period of 5 minutes, and the mixture was stirred for another 5 minutes. Then, 0.242 g of acetone (4.16 mmol), dissolved in 3 ml of THF, were added dropwise over 5 minutes. The mixture was stirred at -80 ° C for another 30 minutes and then warmed to room temperature over the course of 1 hr. The mixture was extracted with semi-concentrated sodium bicarbonate / dichloromethane solution. The aqueous phase was extracted three more times with dichloromethane. The organic phases were combined, washed with a little water, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel by MPLC using the ethyl acetate / methanol mobile phase. After purification, 33.0 mg (8.7% of theory) were obtained.

logP [n]: 0.57;

1H NMR (CD 3 CN, 400MHz); 8 = 1.51 (s, 6H), 3.39 (s, 3H), 3.96 (s, 3H), 6.20 (s, 1H), 7.33-7.37 (m, 1H) , 7.65-7.68 (m, 1H), 8.367-8.374 (m, 1H), 8.42-8.43 (m, 1H) ppm.

Example: 2- [Hydroxy (phenyl) methyl] -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-12)

0.300 g (1.39 mmol) of N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (IX-1-1) was dissolved in 5 ml of THF and cooled to -90 ° C. During the reaction, the temperature was kept between -85 ° C and -90 ° C. At -90 ° C, 0.58 ml (1.45 mmol) of a 2.5 molar solution of n-BuLi in n-hexane was added dropwise over a period of 5 minutes, and the mixture was stirred for another 5 minutes. Over the course of 5 minutes, 0.423 ml of benzaldehyde (4.16 mmol) was then heated to room temperature over 30 minutes. The mixture was extracted with semi-concentrated sodium bicarbonate / dichloromethane solution. The aqueous phase was extracted three more times with dichloromethane. The organic phases were combined, washed with a little water, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel by MPLC using the ethyl acetate / methanol mobile phase. After purification, 227 mg (50.8% of theory) were obtained.

logP [a]: 0.52; logP [n]: 1.23;

1H NMR (CD 3 CN, 400MHz); 8 = 3.38 (s, 3H), 3.64 (s, 3H), 4.28-4.30 (d, 1H), 5.84-5.85 (d, 1H), 6.25 ( s, 1H), 7.26 7.37 (m, 6H), 7.64-7.67 (m, 1H), 8.378-8.385 (m, 1H), 8.44-8.47 (m, 1H ) ppm.

Example: 2-Benzyl-N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-3)

A suspension of 50.0 mg (0.152 mmol) of 2- [hydroxy (phenyl) methyl] -N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I- 1-12) and 170 mg (0.298 mmol) of tetraiododiphosphane in 2 ml of dichloromethane at 40 ° C for 48 hours. The mixture was extracted with semi-concentrated sodium bicarbonate / dichloromethane solution. The aqueous phase was extracted three more times with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel by MPLC using the ethyl acetate / methanol mobile phase. After purification, 12.0 mg (24.5% of theory) were obtained.

logP [a]: 0.64; logP [n]: 1.48;

1H NMR (CD 3 CN, 400MHz); 8 = 3.38 (s, 3H), 3.63 (s, 3H), 4.02 (s, 2H), 6.23 (s, 1H), 7.10-7.12 (m, 2H) , 7.20-7.24 (m, 1H), 7.27-7.31 (m, 2H), 7.34-7.37 (m, 1H), 7.64-7.67 (m, 1H), 8.39-8.40 (m, 1H), 8.44-8.45 (m, 1H) ppm.

Procedure D

Example: 2-Iodo-N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (X-1-1)

5.00 g (23.1 mmol) of N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (IX-1-1) were dissolved in 150 ml of THF and cooled to -90 ° C. During the reaction, the temperature was kept between -85 ° C and -90 ° C. At -90 ° C, 9.68 ml (24.2 mmol) of a 2.5 molar solution of n-BuLi in n-hexane was added dropwise over a period of 30 minutes, and the mixture was stirred for another 5 minutes. Then 0.242 g of iodine (69.4 mmol), dissolved in 50 ml of THF, were added dropwise over a period of 20 minutes. The mixture was stirred at -80 ° C for another 30 minutes and then warmed to room temperature over the course of 1 hr. The mixture was extracted with semi-concentrated sodium bicarbonate / dichloromethane solution. The aqueous phase was extracted three more times with dichloromethane. The organic phases were combined, washed with a little water, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel by MPLC using the ethyl acetate / methanol mobile phase. After purification, 4.35 g (55.0% of theory) were obtained.

logP [a]: 0.66; logP [n]: 0.97;

1 H NMR (d 6 -DMSO, 400MHz); 8 = 3.37 (s, 3H), 3.74 (s, 3H), 6.27 (s, 1H), 7.42-7.45 (m, 1H), 7.82-7.85 ( m, 1H), 8.465-8.495 (m, 2H) ppm.

Example: N, 1-Dimethyl-N- (pyridin-3-yl) -2-vinyl-1H-imidazole-5-carboxamide (I-1-6)

A solution of 400 mg (1.17 mmol) of 2-iodo-N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (X-1-1) and 535 mg (1.64 mmol) of tributyl (vinyl) stanan in 12 ml of N, N-dimethylformamide with argon. 8.2 mg (0.012 mmol) of palladium-bis (triphenylphosphine) dichloride were added and the solution was stirred at 70 ° C for 18 hours. 535 mg (1.64 mmol) of tributyl (vinyl) stanan and 8.2 mg (0.012 mmol) of palladiobis (triphenylphosphine) dichloride were added and the solution was stirred at 70 ° C for another 18 hours. The mixture was concentrated. The residue was purified on silica gel by MPLC using the ethyl acetate / methanol mobile phase. After purification, 200 mg (70.6% of theory) were obtained.

logP [n]: 0.82;

1H NMR (CD 3 CN, 400MHz); 8 = 3.395 (s, 3H), 3.78 (s, 3H), 5.42-5.46 (dd, 1H), 6.06-6.11 (dd, 1H), 6.27 (s, 1H), 6.65-6.72 (dd, 1H), 7.34-7.37 (m, 1H), 7.66-7.68 (m, 1H), 8.397-8.403 (m, 1H) , 8.44-8.45 (m, 1H) ppm.

Procedure E

Example: N, 1-Dimethyl-2- (phenylethynyl) -N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (IV-1-1)

A solution of 400 mg (1.17 mmol) of 2-iodo-N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (X-1-1) was degassed with argon and 239 mg (2.34 mmol) of phenylacetylene in 6 ml of triethylamine. 41 mg (0.058 mmol) of palladium-bis (triphenylphosphine) dichloride and 22.3 mg of copper (I) iodide (0.117 mmol) were added and the solution was stirred at room temperature for 2 hours. The mixture was extracted with ethyl acetate and the extract was washed twice with water and once with concentrated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel by MPLC using the cyclohexane / ethyl acetate / methanol mobile phase. After purification, 200 mg (54.1% of theory) were obtained.

logP [a]: 1.86; logP [n]: 1.98;

1 H NMR (d 6 -DMSO, 400MHz); 8 = 3.40 (s, 3H), 3.92 (s, 3H), 6.32 (s, 1H), 7.45-7.50 (m, 4H), 7.63-7.66 ( m, 2H), 7.86-7.88 (m, 1H), 8.50-8.57 (m, 2H) ppm.

Example: N, 1-Dimethyl-2- (phenylethyl) -N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (I-1-5)

A suspension of 40.0 mg (0.619 mmol) of N, 1-dimethyl-2- (phenylethynyl) -N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (IV-1-1) was stirred and 20.0 mg of palladium on 10% activated carbon in 20 ml of methanol at room temperature and under 1000 kPa (10 bar) of hydrogen for 16 hours. 20.0 mg of palladium on 10% activated carbon was added and once more the suspension was stirred at room temperature and under 1000 kPa (10 bar) of hydrogen for 18 hours. The mixture was filtered through Celite and concentrated. The residue was purified on silica gel by MPLC using the cyclohexane / ethyl acetate mobile phase. After purification, 99.0 mg (48.9% of theory) were obtained.

logP [a]: 0.66; logP [n]: 1.58;

1H NMR (da-DMSO, 400MHz); 8 = 2.89 (m, 4H), 3.35 (s, 3H), 3.565 (s, 3H), 6.15 (s, 1H), 7.14-7.21 (m, 3H), 7 , 7.29 (m, 2H), 7.43-7.46 (m, 1H), 7.80-7.83 (m, 1H), 8.44-8.45 (m, 1H), 8.46-8.48 (m, 1H) ppm.

Procedure F

Example: N, 1-Dimethyl-N- (pyridin-3-yl) -2- [2,2,2-trifluoro-1- (2,2,2-trifluoroethoxy) ethyl] -1H-imidazole-5-carboxamide (I-1-67)

200 mg (0.925 mmol) of N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (IX-1-1) was dissolved in 7.5 ml of THF and cooled to -90 ° C. During the reaction, the temperature was kept between -85 ° C and -90 ° C. At -90 ° C, 0.41 ml (1.02 mmol) of a 2.5 molar solution of n-BuLi in n-hexane was added dropwise over a period of 5 minutes, and the mixture was stirred for another 5 minutes. Then 644 mg (2.77 mmol) of 2,2,2-trifluoroethyl trifluoromethanesulfonate, dissolved in 2.5 ml of THF, were added dropwise over 5 minutes. The mixture was stirred at -80 ° C for another 30 minutes and then warmed to room temperature for 1 hr. The mixture was extracted with semi-concentrated sodium bicarbonate / dichloromethane solution. The aqueous phase was extracted three more times with dichloromethane. The organic phases were combined, washed with a little water, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel by MPLC using the ethyl acetate / methanol mobile phase. The desired fraction was purified by reverse phase medium pressure (RP) column chromatography with water / acetonitrile. After purification, 27 mg (7.2% of theory) were obtained.

logP [a]: 1.72; logP [n]: 1.86;

1H NMR (CDCla, 400MHz); 8 = 3.485 (s, 3H), 3.92-4.01 (m, 2H), 3.955 (s, 3H), 5.11-5.14 (q, 1H), 6.36 (s, 1H) , 7.33 7.35 (m, 1H), 7.51-7.53 (m, 1H), 8.43-8.44 (m, 1H), 8.54-8.55 (m, 1H ) ppm.

In Table 1, other compounds of formula (I) or (I-1) are set forth, which were prepared analogously to the examples set forth above.

Table 2

Analytical data for the compounds indicated in Table 1

The 1 H NMR data for the selected examples are provided as lists of 1 H NMR peaks. For each signal peak, the value 8 in ppm is shown first and then the signal intensity in parentheses. The pairs of 8 -signal strength value numbers for different signal peaks are shown separated from each other by semicolons.

The list of peaks for an example therefore takes the following form:

81 (intensity- i ); 82 (intensity 2 ); ........; 8i (intensity i ); .......; 8n (intensity n )

The intensity of sharp signals is correlated with the height of the signals in a printed example of an NMR spectrum in cm and shows the actual relationships of the signal intensities. In the case of wide signals, various peaks or the middle of the signal and their relative intensity can be displayed compared to the strongest signal in the spectrum.

For the calibration of the chemical deviation of the 1 H NMR spectra, we use tetramethylsilane and / or the chemical deviation of the solvent, particularly in the case of the spectra that are measured in DMSO. Therefore, the tetramethylsilane peak may appear, but not necessarily, in the NMR peak lists.

The 1 H NMR peak lists are similar to the conventional 1 H NMR lists and therefore generally contain all the peaks exposed in a conventional NMR interpretation.

Furthermore, like conventional 1H NMR listings, they can show solvent signals, stereoisomeric signals of the target compounds, which are also the object of the invention, and / or impurity peaks.

In reporting the signals for compounds within the delta range of solvents and / or water, our 1 H NMR peak listings show the standard solvent peaks, for example DMSO peaks in d 6 -DMSO and the DMSO peak. water, which generally have a high intensity on average.

The stereoisomeric peaks of the target compounds and / or the impurity peaks generally have a lower intensity on average than the peaks of the target compounds (eg> 90% purity). Said stereoisomers and / or impurities may be typical of the respective preparation process. Their peaks can thus help in the identification of the reproduction of our preparation procedure with reference to "secondary product fingerprints".

An expert who calculates the peaks of the target compounds with known procedures (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, with the use of optionally additional intensity filters . This isolation would be similar to the peak selection in question in the conventional 1H NMR interpretation .

Additional details of the 1 H NMR peak listings can be found in Research Disclosure Database Number 564025.

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Biological Examples

Myzus persicae - spray test

Solvent: 78 parts by weight of acetone

1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient preparation, 1 part by weight of active ingredient is dissolved with the indicated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until the desired concentration is reached. To produce additional test concentrations, dilute with water containing emulsifier.

Chinese cabbage leaf discs ( Brassica pekinensis) infested by all stages of the green peach aphid (Myzus persicae) are sprayed with an active ingredient preparation of the desired concentration.

After 5-6 days, the efficiency in% is determined. In this respect 100% means that all aphids have been killed; 0% means that aphids have not been killed.

In this test, for example, the following compounds of the preparation examples show 100% efficacy with an application rate of 500 g / h at I-1-3, I-1-4, I-1-5, I -1-6, I-1-7, I-1-9, 1-1-13, 1-1-15, I-1-16, I-1-17, I-1-21, I-1 -22, I-1-23, I-1-24, I-1-26, I-1-28, I-1-31, I-1-33, I-1-34, I-1-35 , I-1-37, I-1-42, I-1-43, I-1-44, I-1-46, I-1-47, I-1-48, I-1-51, I -1-53, I-1-62, I-1-64

In this test, for example, the following compounds of the preparation examples show an efficacy of 90% with an application rate of 500 g / ha: I-1-10, I-1-11, I-1-12, I-1-14, I-1-18, I-1-19, I-1-20, I-1-25, I-1-27, I-1-29, I-1-30, I- 1-32, I-1-36, I-1-38, I-1-39, I-1-40, I-1-41, I-1-45, I-1-49, I-1- 50, I-1-52, I-1-54, I-1-56, I-1-57, I-1-58, I-1-59, I-1-60, I-1-61, I-1-63, I-1-65, I-1-71

In this test, for example, the following compounds of the preparation examples show an efficiency of 70% with an application rate of 500 g / ha: I-1-67, I-1-69

Myzus persicae - oral test

Solvent: 100 parts by weight of acetone

To produce a suitable active ingredient preparation, 1 part by weight of active ingredient is dissolved with the indicated parts by weight of solvent and water until the desired concentration is reached.

50 µl of the active principle preparation are transferred to microtiter plates and brought to a final volume of 200 µl with 150 µl of IPL41 insect medium (33% 15% sugar). Subsequently, the plates are sealed with parafilm, which can be pierced by a mixed population of green peach aphids ( Myzus persicae) inside a second microtiter plate and they can drink the solution through said film.

After 5 days, the efficiency in% is determined. In this respect 100% means that all aphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the Preparation Examples show 100% efficacy with an application rate of 20 ppm: I-1-4, I-1-5, I-1-6, I- 1-7, I-1-9, I-1-11, I-1-12, I-1-13, I-1-14, I-1-15, I-1-16, I-1- 17, I-1-18, I-1-19, I-1-20, I-1-21, I-1-22, I-1-23, I-1-25, I-1-26, I-1-27, I-1-28, I-1-29, I-1-30, I-1-31, I-1-32, I-1-33, I-1-34, I- 1-35, I-1-36, I-1-37, I-1-39, I-1-40, I-1-41, I-1-42, I-1-43, I-1- 44, I-1-45, I-1-46, I-1-47, I-1-48, I-1-49, I-1-50, I-1-51, I-1-52, I-1-53, I-1-54, I-1-60, I-1-61, I-1-62, I-1-63, I-1-64, I-1-65, I- 1-71

In this test, for example, the following compounds of the Preparation Examples show an efficacy of 90 % with an application rate of 20 ppm: I-1-3, I-1-8, I-1-24, I-1-38, I-1-56

In this test, for example, the following compounds from the Preparation Examples show an efficacy of 70% with an application rate of 20 ppm: I-1-10, I-1-66

Examples of deposition

Myzus persicae - spray test (MYZUPE)

Solvent: 78.0 parts by weight of acetone

1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient preparation, 1 part by weight of active ingredient is dissolved with the indicated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until the desired concentration is reached. To produce additional test concentrations, dilute with water containing emulsifier.

Chinese cabbage leaf discs ( Brassica pekinensis) infested by all stages of the green peach aphid (Myzus persicae) are sprayed with an active ingredient preparation of the desired concentration.

After the desired period of time, the efficiency in% is determined. In this respect 100% means that all aphids have been eliminated; 0% means that no aphids have been killed.

In this test, for example, the following compounds of the preparation examples show superior efficacy with respect to the state of the art: see Table 3.

Myzus persicae - oral test (MYZUPE O)

Solvent: 100 parts by weight of acetone

To produce a suitable active ingredient preparation, 1 part by weight of active ingredient is dissolved with the indicated parts by weight of solvent and filled with water to the desired concentration.

50 µl of the active ingredient preparation are transferred to microtiter plates and a final volume of 200 µl is reached with 150 µl of IPL41 insect medium (33% 15% sugar). Subsequently, the plates are sealed with parafilm, which can be pierced by a mixed population of green peach aphids ( Myzus persicae) within a second microtiter plate and they can drink the solution through it.

After the desired period of time, the efficiency in% is determined. In this respect 100% means that all aphids have been eliminated; 0% means that no aphids have been killed.

In this test, for example, the following compounds of the preparation examples show superior efficacy with respect to the state of the art: see Table 3.

Myzus persicae - spray test (MYZUPE S)

Solvent: 14 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient preparation, 1 part by weight of active ingredient is dissolved with the specified parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until the desired concentration is reached. To produce additional test concentrations, dilute with water containing emulsifier. If the addition of ammonium salts and / or penetration promoters is required, each is added in a concentration of 1000 ppm to the preparation solution.

Bell pepper plants ( Capsicum annuum) severely infested with the green peach aphid (Myzus persicae) are treated by spraying with the active principle preparation in the desired concentration.

After the desired time, the destruction in% is determined. In this respect 100% means that all the animals have been eliminated; 0% means that no animals have been killed.

In this test, for example, the following compounds of the preparation examples show superior efficacy with respect to the state of the art: see Table 3.

Myzus persicae - drench type soil application test (MYZUPE D)

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable active ingredient preparation, 1 part by weight of active ingredient is mixed with the specified amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, requiring inclusion in the calculation of the volume of soil. that floods. It must be ensured that a concentration of 40 ppm of emulsifier in the soil is not exceeded. To produce additional test concentrations, water is used for dilution.

The Milan cabbage ( Brassica olerácea) is watered in pots with soil with a preparation of active principle of the desired concentration and it is infested with all the stages of the green peach aphid (Myzus persicae). After the desired period of time, the efficiency in% is determined. In this respect 100% means that all aphids have been eliminated; 0% means that no aphids have been killed.

In this test, for example, the following compounds of the preparation examples show superior efficacy with respect to the state of the art: See Table 3.

Aphis gossypii - spray test (APHIGO S)

Solvent: 14 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient preparation, 1 part by weight of active ingredient is dissolved with the indicated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until the desired concentration is reached. To produce additional test concentrations, dilute with water containing emulsifier. If the addition of ammonium salts and / or penetration promoters is required, each is added in a concentration of 1000 ppm to the preparation solution.

Cotton plants ( Gossypium hirsutum) heavily infested by the cotton aphid ( Aphis gossypii) are sprayed with an active ingredient preparation of the desired concentration.

After the desired time, the destruction in% is determined. In this respect 100% means that all aphids have been eliminated; 0% means that no aphids have been killed.

In this test, for example, the following compounds of the preparation examples show superior efficacy with respect to the state of the art: See Table 3.

Table 3

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continuation

Claims (12)

1. Compounds according to formula (I-1)

in which V represents hydrogen, W represents hydrogen, Y represents methyl, A represents methyl, ethyl or cyclopropyl, T represents a pair of electrons or oxygen, L 1 represents a residue of the series hydrogen, methyl, trifluoromethyl, trichloromethyl, isopropyl, isobutyl, 3-methylbutyl (isopentyl), phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl , 3-pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl and benzyl, L 2 represents hydrogen or methyl, or L 1 and L 2 together represent vinyl, prop-1-en-2-yl, (1 £) -prop-1-en-1-yl, (1Z) -prop-1-en-1-yl or cyclopropyl , L 3 represents a residue of the hydrogen series, S (O) n R 1a , OR 1b and N (R 2 ) (R 3 ), in which for the case that L 1 and / or L 2 represents hydrogen or optionally substituted alkyl, L 3 represents a residue of the series S (O) n R 1a , OR 1b and N (R 2 ) (R 3 ), R 1a represents a residue of the series methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopropylmethyl, 2,2-dimethylpropyl, 2-methoxy-2-oxoethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl and 2-pyrimidyl, R 1b represents a residue of the series hydrogen, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3-chlorophenyl and 4-chlorophenyl, R 2 and R 3 together with N represent a heterocycle of the series U-2, U-4, -U-5 and U-13,

Xb represents trifluoromethyl, methyl or cyclopropyl, m represents a number 0 or 1, n represents a number 0 or 2, and its salts. 2. Compounds according to claim 1, characterized in that L3 represents a residue of the series S (O) nR1a, OR1b and N (R2) (R3). Compounds according to claim 1, characterized in that L3 represents a residue of the series S (O) nR1a and N (R2) (R3). 4. Compounds according to claim 1, characterized in that L3 represents an S (O) nR1a residue. 5. Compounds according to claim 1 according to one of the formulas (I-1a), (I-1c) or (I-1d), preferably according to (I-1c)

Agent, with a content of at least one compound according to one of Claims 1 to 5 and customary extenders and / or surfactants in particular for combating animal pests. Method for combating animal pests, in which at least one compound according to one of claims 1 to 5 or one agent according to claim 6 is allowed to act on animal pests and / or their habitat, the treatment being excluded surgical, therapeutic and diagnostic of the human or animal body. Use of at least one compound according to one of claims 1 to 5 or of an agent according to claim 6 to combat animal pests, the surgical, therapeutic and diagnostic treatment of the human or animal body being excluded. Use of at least one compound according to one of claims 1 to 5 for the protection of plant propagation material. 10. Agrochemical formulation containing at least one compound according to one of claims 1 to 5 in biologically effective contents of between 0.00000001 and 98% by weight, relative to the weight of the agrochemical formulation, as well as extenders and / or surfactants. Agrochemical formulation according to claim 10, additionally containing an additional agrochemical active ingredient. 12. Intermediate products of formulas (II) and (III)