MXPA02005023A

MXPA02005023A - Pesticidal aminoheterocyclamide compounds.

Info

Publication number: MXPA02005023A
Application number: MXPA02005023A
Authority: MX
Inventors: Ducray Pierre
Original assignee: Novartis Ag
Priority date: 1999-11-18
Filing date: 2000-11-16
Publication date: 2002-09-18
Also published as: ZA200203861B; AU764228B2; BR0015671A; EP1230239A1; RU2259370C2; WO2001036415A1; KR20020058023A; CA2386318A1; AU2000501A; NZ518376A; JP2003514816A; CN1384832A

Abstract

The invention relates to compounds of general formula (I) wherein R1, R2, R3, R4, R5, X1, X2, X3, m and n have the significances given in claim 1, and optionally the enantiomers thereof. The active ingredients have advantageous pesticidal properties. They are especially suitable for the control of pests on domestic and farm animals.

Description

PESTICIDE COMPOUNDS OF AMINOHETEROCICLAMIDE The present invention relates to new substituted aminohete-rocyclylamides of the formula: wherein: R x is hydrogen, halogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, or unsubstituted or mono- to penta-substituted phenyl, wherein substituents are selected from the group comprising alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, aryloxy, halogen, cyano, and nitro, wherein, if the number of substituents is greater than one, the substituents may be identical or different; R2 is hydrogen, alkyl of 1 to 6 carbon atoms, (alkylene of 1 to 6 carbon atoms) phenyl, pyridyl, COORß, r CONR7R8, COR6, to the ilo, or CH2 -0-R6; Xi is N; ? 2 is C (CN), C (C00R6), C (CORs), C (SOR6), C (C0NR7R8) or C (N02); X3 is O or S; Q is CH or N; R3 and R4, independently of one another, are hydrogen, alkyl of 1 to 6 carbon atoms, or together with the carbon atom to which they are attached, a cycloalkyl ring of 3 to 7 carbon atoms; R5 is a substituent from the group comprising alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, aryloxy, halogen, cyano, hydroxyl, amino, nitro, and mono- to penta-substituted phenyl, wherein the substituents are selected from the group comprising alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, aryloxy, halogen, cyano, hydroxyl, amino, and nitro, and if the number of phenyl substituents is greater than one, can be identical or different, wherein, if m is greater than 1, the substituents R5 can be identical or different; Re is alkyl of 1 to 6 carbon atoms, phenyl, or benzyl; R and Ra, independently of one another, are hydrogen or alkyl of 1 to 6 carbon atoms; m is 1, 2, or 3; and n is 0 or 1. to its preparation, and to its use in the control of pests, and also to pesticides that contain at least one of these compounds. Substituted aminoheterocyclylamides having pesticidal activity are described, for example, in German Patent Number DE 197 27 162. However, the active ingredients specifically disclosed therein, do not always satisfy the requirements with respect to power and spectrum of activity . Accordingly, there is a need for active ingredients with better pesticidal properties. It has now been found that the aminoheterocyclylamides of the formula I have excellent pesticidal properties, especially against the endoparasites. The alkyl groups present in the definitions of the substituents can be straight or branched chain, and are, for example, methyl, ethyl, normal propyl, isopropyl, normal butyl, secondary butyl, isobutyl, tertiary butyl, pentyl, and hexyl, as well as its branched isomers. As a rule, halogen means fluorine, chlorine, bromine, or iodine. The same applies to halogen in combination with other meanings, such as haloalkyl or halophenyl. The haloalkyl groups preferably have a chain length of 1 to 6 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2, 2, 3, 3-tetrafluoroethyl, and 2,2,2-trichloroethyl; preferably trichloromethyl, difluoro-chloromethyl, difluoromethyl, trifluoromethyl, and dichlorofluoromethyl. Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, normal butoxy, isobutoxy, secondary butoxy and tertiary butoxy, as well as the pentyloxy and hexyloxy isomers; preferably methoxy and ethoxy. Preference is given to the compounds of the formula I, wherein: Ri is halogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, or unsubstituted or mono phenyl - penta-substituted, wherein the substituents are selected from the group comprising alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, aryloxy, halogen, cyano , and nitro, wherein, if the number of substituents is greater than one, the substituents may be the same or different; R 2 is hydrogen, alkyl of 1 to 6 carbon atoms, (alkylene of 1 to 6 carbon atoms) phenyl, or pyridyl; Xi is N; X2 is C (CN); X3 is 0 or S; Q is CH or N; R3 and R / independently of one another are hydrogen, alkyl of 1 to 6 carbon atoms, or, together with the carbon atom to which they are attached, a cycloalkyl ring of 3 to 7 carbon atoms; Rs is a substituent from the group comprising alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, aryloxy, halogen, cyano, hydroxyl, amino, and nitro, wherein, if m is greater than 1, the substituents can be identical or different; m is 1, 2, or 3; and n is 0 or 1. Especially preferred compounds in the context of formula I include substances of the formula la; wherein, the substituents are defined as in the formula I Preferred embodiments in the context of the compounds of the formulas I and the are: (1) A compound of the formula I, wherein X3 is O; (2) A compound of the formula I, wherein Ri is halogen or haloalkyl of 1 to 6 carbon atoms; preferably fluorine, chlorine, or haloalkyl of 1 to 4 carbon atoms; More preferably chloro or haloalkyl of 1 to 2 carbon atoms; and most preferably chloro or trifluoromethyl; (3) A compound of the formula I, wherein R 2 is hydrogen or alkyl of 1 to 6 carbon atoms; preferably hydrogen or alkyl of 1 to 2 carbon atoms; more preferably hydrogen; (4) A compound of formula I, wherein R3 and R, independently of one another, are hydrogen, alkyl of 1 to 2 carbon atoms, or together with the carbon atom to which they are attached, a cycloalkyl ring from 3 to 6 carbon atoms; preferably hydrogen, or together with the carbon atom to which they are bonded, a cycloalkyl ring of 3 to 5 carbon atoms; more preferably hydrogen, or together with the carbon atom to which they are linked, a cyclopropyl ring; (5) A compound of the formula I, wherein m is 1 or 2, preferably 2; (6) A compound of the formula I, wherein n is 0; (7) A compound of the formula I, wherein Ri is halogen or haloalkyl of 1 to 6 carbon atoms; R2 is hydrogen or alkyl of 1 to 6 carbon atoms; R3 and R, independently of one another, are hydrogen, alkyl of 1 to 2 carbon atoms, or together with the carbon atom to which they are attached, is a cycloalkyl ring of 3 to 6 carbon atoms; m is 1 or 2; and n is 0; (8) A compound of the formula I, wherein Ri is fluorine, chlorine, or haloalkyl of 1 to 4 carbon atoms; R2 is hydrogen or alkyl of 1 to 2 carbon atoms; R3 and R4 are hydrogen, or together with the carbon atom to which they are bonded, a cycloalkyl ring of 3 to 5 carbon atoms; m is 2; and n is 0; (9) A compound of the formula I, wherein Ri is chloro, or haloalkyl of 1 to 2 carbon atoms; R2 is hydrogen; R3 and R4 are hydrogen, or together with the carbon atom to which they are linked, a cyclopropyl ring; m is 2; and n is 0. A further object of the invention is the process for the preparation of the compounds of the formula I, and optionally their enantiomers, for example characterized in that a compound of the formula: which is known or can be produced in a manner analogous to the corresponding known compounds, and in which Ri, 2, Xi and y 2 are defined as given for formula I, reacted with a compound of the formula : which is known or can be produced in a manner analogous to the corresponding known compounds, wherein X3, R3, R, R5, m, n, and Q are defined as for formula I, and Z is a leaving group, optionally in the presence of a basic catalyst, and if desired, a compound of formula I that can be obtained by this process or otherwise, or an enantiomer thereof, can be converted to another compound of formula I or an enantiomer of the same; a mixture of enantiomers that can be obtained by this process is separated, and the desired enantiomer is isolated. Suitable leaving groups are halogen, alkoxy of 1 to 6 carbon atoms, or hydroxyl, preferably chlorine. Suitable bases for facilitating the reaction are, for example, trialkylamine, basic heterocycles, or phosphines. Mention may be made, by way of example, of triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, quinuclidine, 1,5-diazabicyclo [5.4.0] undec-5-ene (DBU), and triphenylphosphine. Di-isopropylethylamine is preferred. The reactants can be reacted together as such, say, without adding a solvent or diluent, for example in the melt. However, for the most part, it is convenient to add an inert solvent or diluent, or a mixture thereof. Examples of these solvents or diluents that may be mentioned are: aromatic, aliphatic and alicyclic hydrocarbons, and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane , dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene, or tetrachloroethene; ethers, such as diethyl ether, dipropyl ether, di-isopropyl ether, dibutyl ether, terbuyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxy di ethyl ether, tetrahydrofuran, or dioxane; ketones, such as acetone, methyl ethyl ketone, or methyl isobutyl ketone; amides, such as N, N-dimethylformamide, N, N-diethylphormamide, N, N-dimethylacetamide, N-methylpyrrolidone, or hexamethylphosphoric triamide; nitriles, such as acetonitrile or propionitrile; and sulfoxides, such as dimethyl sulfoxide. If the reaction is carried out in the presence of a base, the bases used in excess, such as triethylamine, pyridine, N-methylmorpholine, or N, N-diethylamine, can serve as solvents or diluents. Halogenated hydrocarbons, especially dichloromethane, are preferred. The reaction is conveniently carried out in a temperature range from about -20 ° C to about + 150 ° C, preferably from about -10 ° C to about +80 ° C, and most preferably from about 0 ° C to about approximately + 40 ° C. In a preferred embodiment, a compound of formula II is reacted at 0 ° C to 120 ° C, preferably at 20 ° C, in a halogenated hydrocarbon, preferably dichloromethane, with a compound of formula III. The compounds I can be present in the form of one of the possible isomers or as a mixture thereof, for example depending on the number, of the absolute and relative configurations of the asymmetric carbon atoms as pure isomers, such as antipodes and / or diastereoisomers, or as isomeric mixtures, such as enantiomeric mixtures, for example racemates, diastereoisomeric mixtures or racemic mixtures; the invention relates both to the pure isomers and to all possible isomeric mixtures, and is to be understood as such hereinbefore and hereinafter, even when the stereochemical details in each case are not specifically mentioned. Depending on the choice of starting materials and processes, the diastereoisomeric mixtures and the racemic mixtures of the compounds I which are obtained according to the invention or otherwise can be separated in a known manner in the diastereoisomers or racemates pure, based on the physicochemical differences of the constituents, for example by means of fractional crystallization, distillation, and / or chromatography. According to the above, mixtures of enantiomers that can be obtained, such as racemates, can be decomposed in the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high-pressure liquid chromatography (HPLC) on acetylcellulose, with the assistance of appropriate microorganisms, by dissociation with specific in-solubilized enzymes, through the formation of inclusion compounds, for example using chiral crown ethers, wherein only complex with an enantiomer. According to the invention, apart from the isolation of the corresponding isomer mixtures, the generally known methods of diastere-reoselective or enantioselective synthesis can also be applied to obtain pure diastereomers or enantiomers, for example by carrying out the method of the invention using educts with a correspondingly appropriate stereochemistry. It is convenient to isolate or synthesize the biologically more active isomer in each case, for example the mixture of enantiomers or isomers, for example the mixture of enantiomers, if the individual components show differences in their biological efficacy. In the method of the present invention, the starting materials and intermediates used are preferably those which lead to the compounds I described at the beginning as being especially useful. The invention relates especially to the preparation method described in the example. Starting materials and intermediaries, which are new and are used according to the invention for the preparation of the compounds I, as well as their use and the process for the preparation thereof, similarly form an object of the invention. The compounds I according to the invention are notorious for their broad spectrum of activity, and are valuable active ingredients for use in the control of pests, including in particular the control of endo- and ecto-parasites in animals, while they are well tolerated by warm-blooded animals, fish, and plants. In the context of the present invention, it is understood that the ectoparasites are in particular insects, mites, and ticks. These include insects of the order: Lepidoptera, Coleoptera, Homoptera, Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera, Malophagos, Tisanura, Isophore, Psocoptera, and Hymenoptera. However, the ectoparasites that can be mentioned in particular are those that give problems to humans or animals, and that carry pathogens, for example flies, such as Musca domestica, Musca vetustísima, Musca autumnalis, Fannia canicularis, Sarcophaga carnaria , Lucilia cuprina, Hypoderma bovis, Hypoderma ma tum, Chrysomyia chloropyga, Derma tobia homonis, Co-chliomyia ho inivorax, Gasterophilus in testinalis, Oestrus ovis, Stomoxys calcitraras, Haema tobia irritans, and moths (Nema tocera), such as Culicidae , Simuliidae, Psychodidae, but also blood sucking parasites, for example fleas, such as Ctenocephalides felis, and Ctenocephalides canis (fleas of cats and dogs), Xenopsylla cheopis, Pulex irritans, Dermatophilus penetrans, lice, such as Damalina ovis, Pediculus humanis , biting flies and horse flies (Tabanidae), Haema topota spp. such as Haema topota plu-vialis, Tabanidea spp. such as Tabanus nigrovitta tus, Chry-gas from cats and dogs), Xenopsylla cheopis, Pulex irri tans, Dermatophilus penetrans, lice, such as Damalina ovis, Pe-diculus humanis, biting flies and horse flies (TaJa-nidae), Haematopota spp. such as Haematopota pluvialis, Ta -banidea spp. such as Tabanus nigrovi ttatus, Chrysopsinae spp, such as, Chrysops caecutiens, tsetse flies, such as Glossinia species, biting insects, in particular cockroaches, such as Germanic Blattella, Blatta orientalis, American Periplaneta, mites, such as Dermanyssus gallinae, Sarcoptes scabiei, Psoroptes ovis and Psorergates spp, and finally, but not least, ticks. The last ones belong to the Acariña order. Known representatives of ticks are, for example, Boophilus, Amblyomma, Anocentor, Dermacentoir, Haemaphysalis, Hyalomma, Ixodes, Rhipicentor, Margaropus, Rhipicephalus, Argas Otobius and Orni thodoros, and the like, which preferably infest warm-blooded animals. , including farm animals, such as cattle, pigs, sheep, and goats, poultry, such as chickens, turkeys, and geese, fur animals, such as mink, foxes, chinchillas, rabbits, and the like, as well as pets, such as cats and dogs, but also human beings. The compounds I can also be used against hygiene pests, especially of the order Diptera of the families Sarcophagidae, Anophilidae and Culicidae; the orders Or-tq t? aros, Dictyoptera, (for example, the Blattidae family), and chus spp.). They have a high activity against sucking insects of the Homoptera order, especially against the pests of the families Aphididae, Delphacidae, Cicadellidae, Psyllidae, Loccidae, Diaspididae, and Eriophydidae. (for example, mite blight on citrus fruits); the orders Hemiptera, Heteroptera, and Thysanoptera, and on insects that eat plants of the orders Lepidoptera, Coleoptera Diptera, and Orthoptera. They are similarly suitable as a soil insecticide against pests on earth. The compounds of formula I, therefore, are effective against all stages of development of sucking insects and eating insects in crops such as cereals, cotton, rice, corn, soybeans, potatoes, vegetables, fruit, tobacco, hops. , citrus, avocados, and other crops. The compounds of formula I are also effective against nematodes of plants of the species Meloidogyne, Hete-rut, Pra tylenchus, Ditylenchus, Radopholus, Rizoglyphus, et cetera. In particular, the compounds are effective against helminths, where the endoparasitic nematodes can be the cause of serious diseases of mammals and poultry, for example sheep, pigs, goats, cattle, horses, donkeys, dogs, cats, guinea pigs. , and exotic birds. The typical nematodes of this indication are: Haemonchus, Trichostron-helminths, where the endoparasitic nematodes can be the cause of serious diseases of mammals and poultry, for example sheep, pigs, goats, cattle, horses, donkeys, dogs , cats, guinea pigs, and exotic birds. The typical nematodes of this indication are: Haemonchus, Trichostrongy-lus, Ostertagia, Nematodirus, Cooperia_, Ascaris, Bunostonum, Oesophagostonum, Charbertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyu-ris, Ancylostoma, Uncinaria, Toxascaris and Parascaris. The particular advantage of the compounds of the formula I is their effectiveness against these parasites which are resistant to the active ingredients based on benzimidazole. Certain pests of the species Nematodirus, Cooperia, and Oesophacfostzonum, infest the intestinal tract of the host animal, while other of the species Haemonchus and Ostertagia are parasitic in the stomach, and those of the species Dictyocaulus are parasitic in the lung tissue. Parasites of the families Filariidae and Setariidae can be found in the internal cell tissue and in the organs, for example in the heart, in the blood vessels, in the lymphatics, and in the subcutaneous tissue. A particularly notorious parasite is the dog heartworm, Dirof liarla immi tis. The compounds of the formula I are highly effective against these parasites. In addition, the compounds of formula I are also effective against parasites of the Wu-chereria, Brugia, Onchocerca, and Loa species of the family of Filarii-dae, which appear in the blood, in the tissue, and in different organs, and also against Dracunculus and parasites of the Strongyloides and Trichinella species, which infect the gastrointestinal tract in particular. The good pesticidal activity of the compounds of the formula I corresponds to a mortality rate of at least 50 to 60 percent of the pests mentioned. In particular, the compounds of the formula I are notorious for the exceptionally long duration of effectiveness. The activity of the compounds according to the invention, and of the compositions containing them, against the animal pests, can be extended and adapted substantially to the prevailing circumstances, by the addition of other insecticides and / or acaricides. The additives in question can be, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenols and derivatives, formamidines, ureas, carbamates, pyrethroids, chlorinated hydrocarbons, neonicotinoids, and preparations of Bacillus thuringiensis. The compounds of the formula I are preferably used in an unmodified form, or preferably together with the adjuvants conventionally used in the formulation art, and therefore, can be processed from a known mill to give, for example , emulsifiable concentrates, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dry powders, granules or microencapsulations in polymeric substances. As with the compositions, the methods of application, such as spraying, atomizing, dusting, scattering, or watering, are selected in accordance with the intended objectives and the prevailing circumstances. The formulation, i.e., the agents, preparations or compositions containing the active ingredient of the formula I, or combinations of these active ingredients with other agrochemical active ingredients, and optionally a solid or liquid adjuvant, are produced in a manner known per se. itself, for example by intimate mixing and / or milling of the active ingredients with extender compositions, for example with solvents, solid carriers, and optionally surface active compounds (surfactants). The solvents in question may be: aromatic hydrocarbons, preferably fractions of alkylbenzenes having from 8 to 12 carbon atoms, such as mixtures of alkylated xylenes or naphthalenes, aliphatic or cycloaliphatic hydrocarbons, such as cyclohexane, paraffins or tetrahydro-naphthalene , alcohols, such as ethanol, propanol or butanol, glycols and their ethers and esters, such as propylene glycol, di-propylene glycol ether, ethylene glycol, or monomethyl or -ethyl ether of alkylated xylenes or naphthalenes, aliphatic or cycloaliphatic hydrocarbons, such as cyclohexane, paraffins or tetrahydronaphthalene, alcohols, such as ethanol, propanol or butanol, glycols and their ethers and esters, such as propylene glycol, di-propylene glycol ether, ethylene glycol, or ethylene glycol monomethyl or ethylether, ketones, such as cyclohexanone, isophorone or diacetanol alcohol, solvents strong polar, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, or dimethylformamide, or vegetable oils, such as rapeseed oil, castor oil, coconut, or soybean seed, and also, if appropriate, silicone oils. The solid carriers used, for example, for dry powders, and dispersible powders, are normally natural mineral fillers such as calcite, talc, kaolin, ontmori-lonite or attapulgite. In order to improve the physical properties, it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granular adsorbent carriers are porous types, for example pumice, broken septum, sepiolite, or bentonite, and suitable non-sorbent carriers are materials such as calcite or sand. In addition, a large number of previously granulated materials of an inorganic or organic nature can be used, for example especially dolomite or pulverized plant residues. Depending on the type of active ingredient of the form it is understood that the surfactants are mixtures of surfactants VOS. Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surfactants. Suitable soaps are the alkali metal salts, the alkaline earth metal salts, or the unsubstituted or substituted ammonium salts of higher fatty acids (10 to 22 carbon atoms), for example the sodium or potassium salts of oleic or stearic acid , or mixtures of natural fatty acids which can be obtained, for example, from coconut oil or tallow oil. Fatty acid methyl taurine salts can also be mentioned as surfactants. Nevertheless, more often so-called synthetic surfactants are used, especially fatty sulphonates, fatty sulfates, sulfonated benzimidazole derivatives, or alkylaryl sulphonates. The sulfonates or fatty sulfates are usually in the form of alkali metal salts, alkaline earth metal salts, or unsubstituted or substituted ammonium salts, and have an alkyl radical having 8 to 22"carbon atoms, which also includes the alkyl of the acyl radicals, for example the sodium or calcium salt of lignin sulphonic acid, of dodecyl sulfate, or of a mixture of fatty alcohol sulfates obtained from natural fatty acids, these compounds also comprise the salts of the esters of the Sulfuric acid and sulfonic acids of fatty alcohol / ethylene oxide adducts The benzimidazole sulfonata-2 derivatives preferably contain two sulfonic acid groups and a fatty acid radical containing from 8 to 22 carbon atoms. Alkylaryl sulphonates are the sodium, calcium, or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or a prod Condensation uct of naphthalenesulfonic acid / formaldehyde. Also suitable are the corresponding phosphates, for example the salts of the phosphoric acid ester of a p-nonylphenol adduct with 4 to 14 moles of ethylene oxide or phospholipids. The nonionic surfactants are preferably the polyglycol ether derivatives of the aliphatic or cycloaliphatic alcohols, or saturated or unsaturated fatty acids and alkylphenols, these derivatives containing from 3 to 30 glycol ether groups, and from 8 to 20 carbon atoms in the fraction thereof. hydrocarbon (aliphatic), and from 6 to 18 carbon atoms in the alkyl fraction of alkylphenols. Other suitable nonionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, polypropylene glycol of ethylene diamine, and alkyl polypropylene glycol containing from 1 to 10 carbon atoms in the alkyl chain, the adducts of which contain from 20 to 250 ethylene glycol ether groups, and from 10 to 100 propylene glycol ether groups. These compounds are usually polyethylene with polypropylene glycol, polypropylene glycol of ethylene diamine, and alkyl polypropylene glycol containing from 1 to 10 carbon atoms in the alkyl chain, which adducts contain from 20 to 250 ethylene glycol ether groups, and from 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit. Examples of nonionic surfactants are nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene oxide / polyethylene adducts, tributyl phenoxy polyethoxyethanol, polyethylene glycol, and octylphenoxypolyethoxyethanol. Also suitable are polyoxyethylene sorbitan fatty acid esters, such as polyoxyethylene sorbitan trioleate. Preferred cationic surfactants are quaternary ammonium salts having, as N-substituent, at least one alkyl radical of 8 to 22 carbon atoms, and as further substituents, lower alkyl radicals - where appropriate - halogenated, benzyl, or lower hydroxyalkyl. The salts preferably exist as halides, methyl sulfates or ethyl sulfates, preferably as stearyltrimethylammonium chloride or benzyl-di- (2-chloroethyl) -ethyl ammonium bromide. Surfactants that become accustomed to the technology of the formulation are described, for example, in the following publications: "Me Cutcheon's Detergents and Emulsifiers Annual," McPublishing Corp., Glen Rock, NJ, USA, 1988. "H. Stache," Tensid-Taschenbuch "(Handbook of Surfactants) 2nd edition, C. Hanser Publishing Munich, Vienna 1981. M. and J. Ash." Encyclopedia of Surfactants ", volumes I-III, Chemical Publishing Co., New York, 1980-1981 Preferred application forms for use in warm-blooded animals in helminth control include solutions, emulsions, suspensions (potions), food additives, powders, tablets including effervescent tablets, boluses, capsules, microcapsules, and poured formulations, where the physiological compatibility of the excipients of the formulation must be taken into consideration. The binders for tablets and boluses can be chemically modified natural polymeric substances which are soluble in water or alcohol, such as starch, cellulose, or protein derivatives (eg, methylcellulose, carboxymethylcellulose, ethylhydroxyethylcellulose, proteins such as zein, gelatin). , and the like), as well as synthetic polymers, such as polyvinyl alcohol, polvinylpyrrolidone, and the like. The tablets also contain fillers (eg, starch, microcrystalline cellulose, sugar, lactose, etc.), slip aids and disintegrants. if the anthelmintics are present in the form of concentrates for food, then the vehicles used are, for example, performance foods, food grain, or protein concentrates. These concentrates or food compositions may contain, apart from the active ingredients, also additives, vitamins, antibiotics, chemotherapeutics or other pesticides, primarily bacteriostatic, fungistatic, coccidiostatic, or even hormone preparations, substances having an anabolic action, or substances that promote growth that affect the quality of the meat of the animals for slaughter, or that are beneficial for the organism in another way. If the compositions or active ingredients of the formula I contained therein are added directly to the food or to the troughs for drinking, then the formulated food or beverage contains the active ingredients preferably in a concentration of about 0.0005 to 0.02. percent by weight (from 5 to 200 ppm). The application of the compositions according to the invention to the animals to be treated may take place topically, perorally, parenterally, or subcutaneously, the composition being present in the form of solutions, emulsions, suspensions (potions), powders, tablets , boluses, capsules, and formulations poured. The compounds of the formula I according to the invention can be used alone or in combination with other biocides. They can be combined with pesticides that have the same activity spectrum, for example, to increase activity, or with substances that have another sphere of activity, for example, to extend the range of activity. It may be successful to also add so-called repellents. If the range of activity is to be extended to endoparasites, for example, the compounds of formula I are suitably combined with substances having endoparasitic properties. Of course, they can also be used in combination with antibacterial compositions. Since the compounds of the formula I are adulti-cides, that is to say, since they are effective in particular against the adult stage of the target parasites, the addition of pesticides that attack rather the juvenile stages of the parasites can be very advantageous. In this way, most of those parasites that cause great economic damage will be covered. In addition, this action will contribute substantially to avoiding the formation of resistance. Many combinations can also lead to synergistic effects, that is, the total amount of active ingredient can be reduced, which is desirable from an ecological point of view. Preferred groups of components for combinations and components for especially preferred combinations are mentioned below, wherein the 'combinations may contain one or more of these components in addition to a compound of the formula I. Suitable components in the mixture can be biocides, for example, insecticides and acaricides with a variable mechanism of activity, which are mentioned below and have been known to the person skilled in the art for a long time., for example, inhibitors of chitin synthesis, growth regulators; active ingredients that act as juvenile hormones; active ingredients that act as adulticides; Broad band insecticides, acaricides and broad band nematicides; and also the well-known anthelmintics and substances for killing insects and mites, said repellents or separators. Non-limiting examples of suitable insecticides and acaricides are: (I) Aldicarb; (XIV) zeta-Cyper (XXX) Parathion; (II) Azinphos-methrin; (XXXI) Parathionmethyl; methyl; (XV) Deltamethrin; (XXXII) Phosalone; (III) Benfuracarb; (XVI) Diflubenzuron; (XXXIII) Pirimicarb; (IV) Bifenthrin; (XVII) Endosulfan; (XXXIV) Propoxur; (V) Buprofezin; (XVIII) Ethiophencarb; (XXXV) Teflubenzuron; (VI) Carbofuran; (XIX) Fenitrothion; (XXXVI) Terbufos; (VII) Dibutylamino (XX) Fenobucarb; (XXXVII) Triazamate; thio; (XXI) Fenvalerate; (XXXVIII) .Abamectin; (VIII) Cartap; (XXII) Formothion; (XXXIX) Fenobucarb; (IX) Chlorfluazuron; (XXIII) Methiocarb; (XL) Tebufenozide; (X) Chlorpyrifos; (XXIV) Heptenophos; (XLI) Fipronil; (XI) Cyfluthrin; (XXV) Imidacloprid; (XLII) beta-Cyfluthrin; (XII) Lambda-Cy- (XXVI) Isoprocarb; (XLIII) Silafluofen; halothrin; (XXVII) Metha idophos; (XLIV) Fenpyroximate; (XIII) Alpha-cyper (XXVIII) Methomyl; (XLV) Pyridaben; methrin; (XXIX) Mevinphos; (XLVI) Fenazaquin; (XLVII) Pyriproxyfen; (XLIX) Nitenpyram; (L) NI -25, Acetami- (XLVIII) and rimidifen; prid; (LII) Avermectin; (LIII) an extract of an active plant against insects; (LIV) a preparation containing nematodes active against insects; (LV) a preparation obtained from Bacillus subtilis; (LVI) a preparation containing fungi active against insects, - (LVII) a preparation containing virus active against insects; (LIX) AC 303 630; (LXXXIV) Cis-Resmethrin; (CVII) Fenbutatinoxid, - (LX) Accepts; (LXXXV) Clocythrin; (CVIII) Fenothiocarb; (LXI) Acrinathrin; (LXXXVI) Clofentezin; (CIX) Fenpropa hrin; (LXII) Alanycarb; (LXXXVII) Cyanophos; (CX) Fenpyrad; (LXIII) Alfamethrin; (LXXXVIII) Cycloprothrin; (CXI) Fenthion; (LXIV) Amitraz; (LXXXIX) Cyhexatin; (CXII) Fluazinam; (LXV) AZ60541 (XC) Demeton M; (CXIII) Flucycloxuron; (LXVI) Azinphos A; (XCI) Demeton S; (CXIV) Flucythrinat; (LXVII) Azinphos M; (XCII) Demeton-S- (CXV) Flufenoxuron; (LXVIII) Azocyclotin; methyl; (CXVI) Flufenprox; (LXIX) Bendiocarb; (XCIII) Dichlofenthion; (CXVII) Fonophos; (LXX) Bensultap; (XCIV) Dicliphos; (CXVIII) Fosthiazat; (LXXI) Betacyfluthrin; (XCV) Diethion; (CXIX) Fubfenprox; (LXXII) BPMC; (XCVI) Dimethoat; (CXX) HCH; (LXXIII) Brofenprox; (XCVII) Dimethylvin- (CXXI) Hexaflumuron; (LXXIV) Bromophos A; phos; (CXXII) Hexythiazox; (LXXV) Bufencarb; (XCVIII) Dioxathion; (CXXIII) Iprobenfos; (LXXVI) Butocarboxin; (XCIX) Edifenphos; (CXXIV) Isofenphos; (LXXVII) Butylpyridaben; (C) E amectin; (CXXV) Isoxathion; (LXXVTII) Cadusafos; (Cl) Esfenvalerat; (CXXVI) Ivermectin; (LXXIX) Carbaryl; (CU) Ethion; (CXXVII) Lambda- (LXXX) Carbophenthion; (CIII) Ethofenprox; cyhalothrin; (LXXXI) Chloethocarb; (CIV) Ethoprophos; (CXXVIII) Malathion; (LXXXII) Chlorethoxyfos; (CV) Etrimphos; (CXXIX) Mecarbam; (LXXXIII) Chlormephos; (CVI) Fenamiphos; (CXXX) Mesulfenphos; (CXXXI) Metaldehyde; (CLXIII) Tefluthrin; (CXCIII) Spinosad (CXXXII) Metolcarb; (CLXIV) Temephos; (CXXXIII) Milbemectin; (CLXV) Terbam; (CXXXIV) Moxidectin; (CLXVI) Tetrachlor- (CXXXV) Naled; vinphos; (CXXXVI) NC 184; (CLXVII) Thiafenox; (CXXXVII) Ornethoat; (CLXVIII) Thiodicarb; (CXXXVIII) Oxamy1; (CLXIX) Thiofanox; (CXXXIX) Oxydemethon M; (CLXX) Thionazin; (CXL) Oxydeprofos; (CLXXI) Thuringiensin; (CXLI) Permethrin; (CLXXII) Tralomethrin; (CXLII) Phenthoat; (CLXXIII) Triarthen; (CXLIII) Phorat; (CLJXIV) Triazophos; (CXLIV) Phosmet; (CLXXV) Triazuron; (CXLV) Phoxim; (CLXXVI) Trichlorfon; (CXLVI) Pirimiphos M; (CLXXVII) Triflumuron; (CXLVII) Pirimiphos A; (CLXXVIII) Trimethacarb; (CXLVIII) Promecarb; (CLXXIX) Vamidothion; (CXLIX) Propaphos; (CLXXX) Xylylcarb; (CL) Prothiophos; (CLXXXI) Yl 5301/5302; (CLI) Prothoat; (CLXXXII) Zetamethrin; (CLII) Pyrachlophos; (CLXXXIII) DPX-MP062; (CLIII) Pyradaphent (CLXXXIV) RH-2485; hion; (CLXXXV) D 2341; (CLIV) Pyresmethrin; (CLXXXVI) XMC (3.5, - (CLV) Pyrethrum; Xi-lil-Methyl (CLVI) RH 5992; carbamat), (CLVII) Salithion; (CLXXXVII) Lufenuron (CLVIII) Rebufos; (CLXXXVIII) Fluazuron (CLIX) Sulfotep; (CLXXXIX) Methoprene (CLX) Sulprofos; (CXC) Hydroprene (CLXI) Tebufenpyrad; (CXCI) Fenoxycarb (CLXII) Tebupirimphos; (CXCII) Chlorfenapyr or Non-limiting examples of suitable anthelmintics are mentioned below, some representatives have insecticidal and acaricidal activity in addition to anthelmintic activity, and are already partially in the above list. (Al) Praziguantel = 2-cyclohexylcarbonyl-4-oxo-l, 2, 3, 6, 7, 11b-hexahydro-4H-pyrazino [2, 1-a] isoquinoline (A2) Closantel = 3, 5-diiodo-N - [5-Chloro-2-methyl-4- (a-cyano-4-chlorobenzyl) phenyl] -salicylamide (A3) Triclabendazole = 5-chloro-6- (2,3-dichlorophenoxy) -2-thiomethyl- IH- benzimidazole (A4) Levamisole L- (-) -2,3,5,6-tetrahydro-6-phenylimidazo [2, Ib] thiazole (A5) Mebendazole (5-benzoyl-lH-benzimidazol-2-yl) methyl ester ) carbamino (A6) Omphalotin = a macrolytic fermentation product of the fungus Omphalotus olearius described in WO 97/20857 (A7) Abamectin = avermectin Bl (A8) Ivermectin = 22, 23-dihydroavermectin Bl (A9) Moxidectin = 5-0- demethyl-28-deoxy-25- (1,3-dimethyl-1-butenyl) -6,28-epoxy-23- (methoxyimino) -milbemycin B (AlO) Doramectin = 25-cyclohexyl-5-0-demethyl-25 -de (1-methylpropyl) -avermectin Ala (All) Milbemectin = mixture of milbemycin A3 and milbemycin A4 (A12) Milbemycinoxim = 5-oxim of milbemectin Non-limiting examples of repellent Suitable separators are: (RI) DEET (N, N-diethyl-m-toluamide) (R2) KBR 3023 N-butyl-2-oxycarbonyl- (2-hydroxy) -piperidine (R3) Cymiazole = N, -2, 3-dihydro-3-methyl-l, 3-thiazol-2-ylidene-2,4-xylidene The said components in the mixture are the best known to those skilled in the art. Most are described in several editions of the Pesticide Manual, The British Crop Protection Council, London, and others in the various editions of The Merck Index, Merck & Co., Inc., Rahway, New Jersey, USA or in the patent literature. Therefore, the following list is restricted to a few places where they can be found by way of example. (I) 2-Methyl-2- (thiomethyl) propionaldehyde-O-Methylcarbamoyloxime (Aldicarb), from the Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 26; (II) S- (3,4-Dihydro-4-oxobenzo [d] - [1,2,3] -triazin-3-ylmethyl) O, O-dimethyl-phosphorodithioate (Azinphos-methyl), from The Pesticide Manual , 11th Ed. (1997), The British Crop Protection Council, London, p. 67; (III) Ethyl-N- [2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl- (methyl) thioamino] -N-isopropyl-β-alaninate (Benfura-carb), from The Pesticide Manual, 11th Ed. (1997) The British Crop Protection Council, London, p. 96; (IV) 2-Methylbiphenyl-3-ylmethyl- (Z) - (1RS) -cis-3- (2-chlor-3,3,3-trifluorprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate (Bifen-thrin ), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 118; (V) 2-tert-Butylimino-3-isopropyl-S-phenyl-1,3,5-thiadiazian-4-one (Buprofezin), from The Pesticide Manual, 11th Ed. (1997), The Bri-tish Crop Protection Council, London, p. 157; (VI) 2, 3-Dihydro-2, 2-dimethylbenzofuran-7-yl-methylcarbamate (Carbofuran) from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 186; (VII) 2, 3-Dihydro-2, 2-dimethylbenzofuran-7-yl- (dibutylthioamino) methylcarbamate (Carbosulfan), from The Pesticide Manual, 11a Ed. (1997), The British Crop Protection Council, London, p. 188; (VIII) S, S- (2-Dimethylaminotrimethylene) -bis (thiocarbamate) (Car-tap), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 193; (IX) 1- [3,5-Dichloro-4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenyl] -3- (2,6-difluorobenzoyl) -urea (Clorfluazuron), from The Pesticide Manual , 11th Ed. (1997) The British Crop Protection Council, London, page 213; (X) O, O-Diethyl-O-3, 5,6-trichloro-2-pyridyl-phosphorothioate (Chlor-pyrifos), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 235; (XI) (RS) -a-Cyano-4-fluoro-3-phenoxybenzyl- (1RS, 3RS; 1RS, 3RS) -3- (2, 2-dichlorovinyl) -2,2-di-methylcyclopropanecarboxylate (Cyfluth-rin ), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 293; (XII) Mixture of (S) -a-Cyano-3-phenoxybenzyl- (Z) - (IR, 3R) -3- (2-chloro-3,3,3-trifluoropropenyl) -2,2-dimethylcyclopropane-carboxylate and (R) -acyano-3-phenoxybenzyl- (72) - (IR, 3R) -3- (2-chloro-3,3,3-trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate (Lambda-Cyhalothrin ), from The Pesticide Manual, 11th Ed. (1997), The British Protection Council, London, p. 300; (XIII) Racemate consisting of (S) -acyano-3-phenoxybenzyl- (1R, 3R) -3- (2,2-dichlorovinyl-2,2-dimethylcyclopropanecarboxylate and (R) -a-cyano-3- Phenoxybenzyl- (1S, 3S) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (Alpha-cypermethrin), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 308; (XIV) Mixture of the stereoisomers of (S) -a-cyano-3-phenoxybenzyl (1RS, 3RS, 1RS, 3RS) -3- (2, 2-dichlorovinyl) -2, 2-dimethyl-cyclopropanecarboxylate (zeta-Cypermethrin), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 314; (XV) (S) - (-cyano-3-phenoxybenzyl- (IR, 3R) -3- (2,2-dibromovinyl) -2,2-dimethylcyclopropanecarboxylate (Deltamethrin), from The Pes-ticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 344; ) (4-Chlorophenyl) -3- (2,6-difluorobenzoyl) urea (Diflubenzu-ron), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Counc il, London, p. 395; (XVII) (1,4,5,6,7,7-Hexachloro-8, 9, 10-trinorborn-5-en-2, 3 -ylene-bismethylene) -sulfite (Endosulfan), from The Pesticide Manual, 11a Ed. (1997), The British Crop Protection Council, London, p. 459; (XVIII) a-Thioethyl-o-tolyl-methylcarbamate (Ethiophencarb), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 479; (XIX) O, O-Dimethyl-O-4-nitro-aTQ-tolyl-phosphorothioate (Fenitrot-hion), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 514; (.XX) 2-sec-Butylphenyl-methylcarbamate (Phenobucarb), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 516; (XXI) (RS) -a-Cyano-3-phenoxybenzyl- (RS) -2- (4-chlorophenyl) -3-methylbutyrate (Fenvalerate), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 539; (XXII) S- [Formyl (methyl) carbamoylmethyl-O, O-dimethyl-phosphorus-dithioate (Formothion), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 625; (XXIII) 4-Tiomethyl-3,5-xylyl-methylcarbamate (Methiocarb), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 813; (XXIV) 7-Clorbicyclo [3.2.0] hepta-2,6-dien-6-yl-dimethylphosphate (Heptenophos), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 670; (XXV) 1- (6-Chloro-3-pyridylmethyl) -N-nitroimidazolidin-2-lideneamine (Imidacloprid), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 706; (XXVI) 2-Isopropylphenyl-methylcarbamate (Isoprocarb), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 729; (XXVII) 0, S-Dimethyl-phosphoramidothioate (Methamidophos), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 808; (XXVIII) S-Methyl-N- (ethylcarbamoyloxy) thioacetimidate (Metho-myl), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 815; (XXIX) Methyl-3- (dimethoxyphosphinoyloxy) but-2-enoate (Mevinphos), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 844; (XXX) O, O-Diethyl-O-4-nitrophenyl-phosphorothioate (Parathion), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 926; (XXXI) O, O-Dimethyl-O-4-nitrophenyl-phosphorothioate (Parathion-methyl), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 928; (XXXII) S-6-Chloro-2,3-dihydro-2-oxo-1,3-benzoxazole-3-methylmethyl-O-diethyl phosphorodithioate (Phosalone), from The Pesticide Manual, 11th ed. (1997) ), The British Crop Protection Council, London, p. 963; (.XXXIII) 2-Dimethylamino-5,6-dimethylpyrimidin-4-yl-dimethyl-carbamate (Pirimicarb), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 985; (XXXIV) 2-Isopropoxyphenyl-methylcarbamate (Propoxur), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1036; (XXXV) 1- (3, 5-Dichloro-2,4-difluorophenyl) -3- (2,6-difluoro-benzoyl) urea (Teflubenzuron), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1158; (XXXVI) S-tert-butylthiomethyl-O, O-dimethyl-phosphorodithioate (Terbu-fos), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1165; (XXXVII) Ethyl- (3-tert-butyl-1-dimethylcarbamoyl-1, 2-, 4-triazol-5-ylthio), (Triazamate), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1224; (XXXVIII) Abamectin, from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 3; (.XXXIX) 2-sec-butylphenyl-methylcarbamate (Phenobucarb), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 516; (XL) N-er-butyl-N- (4-ethylbenzoyl) -3,5-dimethylbenzohydrazide (Tebufenozide), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1147; (XLI) (+) - 5-Amino-1- (2,6-dichloro-a, a, α-trifluoro-p-tolyl) -4-trifluoromethyl-sulfinylpyrazole-3-carbonitrile (Fipronil), from The Pesticide Manual , 11th Ed. (1997), The British Crop Protection Council, London, p. 545; (XLII) (RS) -cyano-4-fluoro-3-phenoxybenzyl (1RS, 3RS; 1RS, 3RS) -3- (2,2-dichlorovinyl) -2, 2-dimethylcyclopropanecarboxylate (beta-Cyfluthrin), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 295; (XLIII) (4-Ethoxyphenyl) - [3- (4-fluoro-3-phenoxyphenyl) propyl] (dimethyl) silane (Silafluofen) from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1105; (XLIV) tert-butyl (E) -oc- (1,3-dimethyl-5-phenoxypyrazol-4-yl-methyleneamino-oxy) -p-toluate (Fenpyroximate), from The Pesticide Manual, 11th Ed. (1997) , The British Crop Protection Council, London, p. 530; (XLV) 2- er-butyl -5- (4-er-butylbenzylthio) -4-chloropyridazin-3 (2M) -one (Pyridaben), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council , London, p. 1161; (XLVI) 4- [[4- (1, 1-dimethylphenyl) phenyl] ethoxy] -quinazoline (Fena-zaquin), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 507; (XLVII) 4-Phenoxyphenyl- (RS) -2- (pyridyloxy) propyl ether (Pyriproxyfen), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1073; (XLVIII) 5 -Cloro-N-. { 2 - [4- (2-ethoxyethyl) -2,3-dimethylphenoxy] ethyl} -6-ethylpyrimidin-4-amine (Pyrimidifen), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1070; (XLIX) (E) -N- (6-chloro-3-pyridylmethyl) -N-ethyl-N-methyl-2-nitro-vinylidene diamine (? Itenpyram), from The Pesticide Manual, 11a Ed. (1997), The British Crop Protection Council, London, p. 880; (L) (E) -N1- (6-chloro-3-pyridyl) methyl] -i-cyano-N-methyl-acetamidine (? I-25, Acetamiprid), from The Pesticide Manual, 11th Ed. ( 1997), The British Crop Protection Council, London, p.

(Ll) Avermectin Bx, from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 3; (LII) an extract of an active plant against insects, especially (21 ?, 6ajS, 12aS) -1, 2, 6, 6a, 12, 12a-hexhydro-2-iso-propenyl-8, 9-dimethoxy- chromene [3, 4-jb] furo [2, 3-h] chromen-6-one (Rotenone), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1097; and an extract from Azadirachta indica, especially azadirachtin, from The Pes-ticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 59; and (Lili) a preparation containing nematodes active against insects, preferably Heterorhabdi tis bacteriophora and Hote-rorhabdi tís megídís, from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 671; Stein- ernema fel tiae, from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1115 and Steíner-nema scapterisci, from The Pestícide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1116; (LIV) a preparation that can be obtained from Bacillus subti -lis, from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 72, or from a strain of Bacillus thuringiensis with the exception of isolated compounds of GC91 or NCTC11821; of The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 73; (LV) a preparation containing fungi active against insects, preferably Verticillium lecanii, from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1266; Beauveria brogniartii, from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 85 and Beauveria bassiana, from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 83; (LVI) a preparation containing active virus against insects, preferably Neodipridon Sertif r NPV, from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 1342; Mamestra brassicae NPV, from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 759 and Cydia pomonella granutosis virus, from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 291; (CLXXXI) 7-Chloro-2,3,4a, 5-tetrahydro-2- [methoxycarbonyl (4-tri-fluoromethoxyphenyl) carbamoyl] indole [1,2-e] oxazolin-4a-carboxylate (DPX-MP062, Indoxycarb), The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, p. 453; (CLXXXII) N-tert-butyl-N '- (3,5-dimethylbenzoyl) -3-methoxy-2-methyl-benzohydrazide (RH-2485, Methoxyfenozide), from The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, Lon-dres, p. 1094; and (CLXXXIII) (N '- [4-methoxy-biphenyl-3-yl] -hydrazinecarboxylic acid isopropyl ester (D 2341), from Brighton Crop Protection Conference, 1996, 487-493; (R2) Book of .Abstracts, 212th ACS National Meeting Orlando, FL, August 25-29 (1996), AGRO-020. Publisher: American Chemical Society, Washington, DC CONEN: 63BFAF As a consequence of the above details, an additional essential aspect of this invention relates to preparations in combination for the control of parasites in warm-blooded animals, characterized in that they contain, in addition to a compound of the formula I, at least one additional active ingredient having the same or different sphere of activity and therefore less a physiologically acceptable carrier The present invention is not restricted to double combinations As a rule, the anthelmintic compositions according to the invention contain from 0.1 to 99 weight percent, especially from 0.1 to 95 weight percent. or of the active ingredient of formula I, or, or mixtures thereof, from 99.9 to 1 weight percent, especially from 99.8 to 5 weight percent of a solid or liquid mixture, including 0 to 25 percent by weight, in particular from 0.1 to 25 weight percent of a surfactant. The poured or exact method consists in applying the compound of formula I to a specific location of the skin or hair, conveniently to the neck or back of the animal. This takes place, for example, by applying a swab or spray of the poured or exact formulation to a relatively small area of the hair, from which the active substance is dispersed almost automatically over wide areas of the hair due to the extensor nature of the components in the hair. formulation, and assisted by the movements of the animal. The poured or accurate formulations suitably contain vehicles that promote rapid dispersion on the surface of the skin or on the hair of the host animal, and are generally considered as extender oils. Suitable carriers are, for example, oily solutions; alcoholic and isopropanolic solutions, such as solutions of 2-octyldodecanol or oleyl alcohol; solutions in esters of monocarboxylic acids, such as isopropyl myristate, isopropyl palmitate, lauric acid oxalate, oleyl ester of oleic acid, decyl ester of oleic acid, hexyl laurate, oleyl oleate, decyl oleate, esters of capric acid of alcohols saturated fatty acids of a chain length of 12 to 18 carbon atoms; solutions of dicarboxylic acid esters, such as dibutyl phthalate, diisopropyl isophthalate, di-isopropylester of adipic acid, di-n-butyl adipate, or else solutions of esters of aliphatic acids, for example glycols. It may be desirable that additionally a dispersing agent be present, such as one known in the pharmaceutical or cosmetic industry. Examples are 2-pyrrolidone, 2- (N-alkyl) pyrrolidone, acetone, polyethylene glycol, and the ethers and esters thereof, propylene glycol, or synthetic triglycerides. Oily solutions include, for example, vegetable oils, such as olive oil, peanut oil, sesame oil, pine oil, linseed oil, or castor oil. The vegetable oils may also be present in an epoxidized form. Paraffins and silicone oils can also be used. The pour or exact formulation generally contains from 1 to 20 weight percent of a compound of the formula I, from 0.1 to 50 weight percent of a dispersing agent, and from 45 to 98.9 weight percent of a solvent. The poured or exact method is especially suitable for use in herd animals, such as cattle, horses, sheep, or pigs, where it is difficult or time consuming to treat all animals orally or by injection. Due to its simplicity, this method, of course, can also be used for all other animals, including pets or individual pets, and is greatly favored by animal caretakers, because it can often be carried out without the presence of the specialist veterinarian. Although it is preferred to formulate commercial products as concentrates, the end user will normally use diluted formulations. These compositions may also contain additional additives, such as stabilizers, antifoaming agents, viscosity regulators, binding or sticking agents, as well as other active ingredients, in order to achieve special effects. Anthelmintic compositions of this type, which are used by the end user, similarly form a constituent of the present invention. In each of the processes according to the invention for the control of pests, or in each of the compositions for the control of pests according to the invention, the active components of the formula I can be used in all its spherical configurations or in mixtures thereof. The invention also includes a method for prophylactically protecting warm-blooded animals, especially livestock producers, pets, and pets, against parasitic helminths, which is characterized in that the active ingredients of formula I are administered, or the formulations of active ingredients prepared therefrom, to animals as an additive to food, or to beverages, or else solid or liquid form, orally or by injection, or parenterally. The invention also includes the compounds of the formula I according to the invention for use in one of these processes. The following examples merely serve to illustrate the invention without restricting it, by representing the term "active ingredient", a substance listed in Table 1. In particular, the preferred formulations are made as follows: (% = percent by weight) Formulation examples 1. Emulsion concentrates a) b) a. C) active ingredient 25% 40% 50% Ca 5% Dodecylbenzenesulfonate 8% 6% Castor oil polyethylene glycol ether (36 moles ethylene oxide) 5% Tributylphenol polyethylene glycol ether (30 moles ethylene oxide) 12% 4 % cyclohexanone 15% 20% mixture of xylenes 65% 25% 20% From these concentrates, emulsions of any desired concentration can be prepared by dilution with water. 2. Concentrates in emulsion a) b) c) Active ingredient 10% 8% 60% Polyethylene glycol ether of octylphenol (4 to 5 moles of ethylene oxide) 3% 3% 3% Dodecylbenzenesulfonate of Ca 3% 4% 4% Polyethylene glycol ether oil of castor (35 moles of ethylene oxide) 4% 5% 4% cyclohexanone 30% 40% 15% mixture of xylenes 50% 40% 15% From these concentrates, emulsions of any desired concentration can be prepared by dilution with water. 3. Concentrate in suspension Active ingredient 40% Ethylene glycol 10% Nonylphene polyethylene glycol ether (15 moles of ethylene oxide) 6% Na 10% lignin sulfonate Carboxymethylcellulose 1% Aqueous formaldehyde solution 37% 0.2% Silicone oil in the form of an aqueous emulsion 75% 0.8% water 32% The finely ground active ingredient is intimately mixed with the mixtures. In this way, a suspension concentrate is obtained, from which suspensions of any desired concentration can be prepared by dilution with water. 4. Powdered mixtures that are dispersible in water a) b) O Active ingredient 25% 50% 75% Na 5% Ligninsulfonate 5% - Oleic acid 3% - 5% Di-isobutylnaphthalenesulfonate Na - 6% 10% Polyethylene glycol ether octyl- phenol (7 to 8 moles of ethylene oxide) 2% Highly dispersed silicic acid 5% 10% 10% Kaolin 62% 27% The active ingredient is thoroughly mixed with the mixtures, and milled well in an appropriate mill. Wettable powders are obtained, which can be diluted with water to form suspensions of any desired concentration. 5. Dry powders a) a. ) Active ingredient 2% 5% Silicic acid highly dispersed 1% 5% Talcum 97% - Kaolin _ 90% By intimately mixing the vehicles with the active ingredient, and by grinding the mixture, ready-to-use dry powders are obtained. 6. Granulate a) b) Active ingredient 5% 10% kaolin 94% Highly dispersed silicic acid 1% Atapulgite 90% The active ingredient is dissolved in methylene chloride, sprayed on the vehicle, and the solvent subsequently concentrated by vacuum evaporation. Granules of this kind can be mixed with the forage. 7. Granulate Active ingredient 10% Na 2% ligninsulfonate Carboxymethylcellulose 1% Kaolin 87% The active ingredient is mixed with the mixtures, milled, and moistened with water. This mixture is extruded and then dried in a stream of air. 8. Granulate Active ingredient 3% Polyethylene glycol (200 mw) 3% Kaolin - 94% (mp = molecular weight) The finely ground active ingredient is uniformly applied in a mixer to the kaolin, which has been wetted with polyethylene glycol. In this way, coated granules free of dust are obtained.

Tablets or boluses Active ingredient 33.00% Methylcellulose 0.80% Silicic acid highly dispersed 0.80% Corn starch 8.40% II Crystalline lactose 22.50% Corn starch 17.00% Microcrystalline cellulose 16.50% Magnesium stearate 1.00% I. Methylcellulose is stirred in water. After the material is swollen, the silicic acid is stirred in, and the mixture is suspended homogeneously. The active ingredient and corn starch are mixed. The aqueous suspension is processed in this mixture and kneaded to a dough. The resulting mass is granulated through a 12M sieve and dried. II. The four excipients are completely mixed. III. The preliminary mixtures obtained according to I and II are mixed and pressed into tablets or boluses. 10. Injectables A. Oily vehicle (slow release) Active ingredient 0.1-1.0 g peanut oil up to 100 ml 2. Active ingredient 0.1-1.0 g sesame oil up to 100 ml Preparation: The active ingredient is dissolved in a part of the oil with stirring, and is required, with a slight heating; then, after cooling, it is brought to the desired volume and sterile filtered through a suitable membrane filter with a pore size of 0.22 mm.

B. Water miscible solvent (Average release rate) Active ingredient 0.1-1.0 g 4-hydroxymethyl -1, 3-dioxolane (glycerol-formal) 40 g 1,2-propanediol up to 100 ml an active ingredient 0.1-1.0 g dimethyl ketal of glycerol 40 g 1,2-propanediol up to 100 ml Preparation: The active ingredient is dissolved in a portion of the solvent with stirring, brought to the desired volume, and sterile filtered through a suitable membrane filter with a pore size of 0.22 mm.

C. Aqueous solubilized (rapid release) 1. Active ingredient 0.1-1.0 g polyethoxylated castor oil (40 units of ethylene oxide) 10 g 1,2-propanediol 20 g benzyl alcohol 1 g water for injection up to 100 ml Active ingredient 0.1 -1.0 g Polyethoxylated sorbitan mono-oleate (20 units of ethylene oxide) 8 g 4-hydroxymethyl-l, 3-dioxolane (glycerol-formal) 20 g. Benzyl alcohol ig Water for injection up to 100 ml, Preparation: The active ingredient is dissolved in the solvents and the surfactant, and brought to the desired volume with water. Sterile filtration through an appropriate membrane filter with a pore size of 0.22 mm. 11 ~ Pouring A. Active ingredient 5 g Isopropyl myristate 10 g Isopropanol up to 100 ml B. Active ingredient 2 g Hexyl laureth 5 g Medium chain triglycerides 15 g Ethanol up to 100 ml Active ingredient 2 g Oleyl oleate 5 g N-methyl pyrrolidone 40 g Isopropanol up to 100 ml Aqueous systems can also be used preferably for oral and / or intraruminal application. The compositions may also contain other additives, such as stabilizers, for example, where appropriate, epoxidized vegetable oils (coconut oil, rapeseed oil, or epoxidized soybean oil); defoamers, usually silicone oil, preservatives, viscosity regulators, binders, and tackifiers, as well as fertilizers or other chemical agents to achieve special effects. Other biologically active substances or additives, which are neutral towards the compounds of the formula I, and which do not have a harmful effect on the host animal to be treated, as well as mineral salts or vitamins, can also be added compositions described. The following examples serve to illustrate the invention. They do not limit the invention. The letter "h" means hours.

Examples dβ Preparation Example 1; [N- (5-cyano-4-trifluoromethylthiazol-2-yl)] -1- [3,5-dichloropyrid-2-yl] -cyclopropyl-1-carbonamide. 278 milligrams of 1- [3,5-dichloropyrid-2-yl] -cyclopropyl-1-carboxylic acid are dissolved at room temperature under a nitrogen atmosphere, in 3.3 milliliters of oxalyl chloride, a drop of dimethylformamide is added, and The mixture is boiled under reflux for 2 hours. After concentration by evaporation in vacuo, the residue is dissolved in 5 milliliters of dry dichloromethane, then 193 milligrams of 2-amino-5-cyano-4-trifluoromethylthiazole are added followed by 0.46 milliliters of di-isopropylethylamine and 23.6 milligrams of 4-dimethylamino-pyridine. The mixture is stirred for 20 hours at room temperature in a nitrogen atmosphere, then washed with a little water, 25 milliliters of a saturated solution of sodium bicarbonate, and finally 25 milliliters of a saturated solution of sodium chloride. After drying the organic phase with magnesium sulfate, filtering, and concentrating by evaporation, the residue is purified on an HPLC column, yielding the title compound with a melting point of 195-197 ° C. The substances mentioned in the following tables 1 to 3 can also be prepared in a manner analogous to the method described above. The values of the melting points are given in C °. Table 1 or. R, R3, R4 n Physical data 1.1 Cl H, H 0 3-Cl 1.2 Cl H, H 0 5-Cl 1.3 Cl H, H 0 5-CF 3 1.4 Cl H, H 0 3,5-Cl 2 1.5 Cl H, H 0 3-Br, 5-Cl 1.6 Cl H, H 0 3-F, 5-Cl 1.7 Cl H, H 0 3-Cl, 5-CF3 1.8 Cl H, H 3-Cl 1.9 Cl H, H 5- Cl 1.11 Cl H, H 3,5-Cl 2 1.12 Cl H, H 3-Br, 5-Cl 1.13 Cl H, H 1 3-F, 5-Cl 1.14 Cl H, H 1 3-Cl, 5-CF 3 1.15 Cl -CH2CH2- 0 3-Cl 1.16 Cl -CH2CH2- 0 5-Cl 1.17 Cl -CH2CH2- 0 5-CF3 1.18 Cl -CH2CH2- 0 3.5-Cl2 1.19 Cl -CH2CH2- 0 3-Br, 5-Cl 1.20 Cl-CH2CH2- 0 3-F, 5-Cl 1.21 Cl -CH2CH2- 0 3-Cl, 5-CF3 1.22 Cl -CH2CH2- 1 3-Cl 1.23 Cl -CH2CH2- 1 5-Cl 1.25 Cl -CH2CH2- 1 3.5-Cl2 1.26 Cl -CH2CH2- 1 3-Br, 5-Cl 1.27 Cl -CH2CH2- 1 3-F, 5-Cl 1.28 Cl -CH2CH2- 1 3-Cl, 5-CF3 1.29 CF3 H, H 0 3-Cl 1.30 CF3 H, H 0 5-Cl 1.31 CF3 H, H 0 5-CF3 1.32 CF3 H, H 0 3.5-Cl2 1.33 CF3 H, H 0 3-Br, 5-Cl 1.34 CF3 H, H 0 3-F, 5-Cl 1.35 CF3 H, H 0 3-Cl, 5-CF3 1.36 CF3 H, H 1 3-Cl 1.37 CF3 H, H 1 5-Cl 1.38 CF3 H, H 5-CF3 1.39 CF3 H , H 3.5-Cl2 1.40 CF3 H, H 3-Br, 5-Cl 1.41 CF3 H, H 3-F, 5-Cl 1.42 CF3 H, H 3-Cl, 5-CF3 1.43 CF3 -CH2 CH2- 0 3-Cl 1.44 CF3 -CH2CH2- 0 5-Cl 1.45 CF3 -CH2CH2- 0 5-CF3 1.46 CF3 -CH2CH2- 0 3.5-Cl2 mp: 195-197 ° C 1.47 CF3 -CH2CH2- 0 3- Br, 5-Cl mp: 157-159 ° C 1.48 CF3 -CH2CH2- 0 3-F, 5-Cl 1.49 CF3 -CH2CH2- 0 3-Cl, 5-CF3 1.50 CF3 -CH2CH2- 3-Cl 1.51 CF3 -CH2CH2 - 5-Cl 1.52 CF3 -CH2CH2- 5-CF3 CF3 1.53 -CH2CH2- 3,5-Cl2 1.54 CF3 -CH2CH2- 3-Br, 5-Cl 1.55 CF3 -CH2CH2- 3-F, 5-Cl 1.56 CF3 CH2CH2 - 3-Cl, 5-CF3 Table 2 (R5) m No. Ri R3, R4 (R5) m Physical data 2. 1 Cl H, H 3-Cl 2.2 Cl H, H 5-Cl 2.3 Cl H, H 5-CF 3 p.f .: 177-178 ° C 2. 4 Cl H, H 3,5-Cl 2 2.5 Cl H, H 3-Br, 5-Cl 2.6 Cl H, H 3 -F, 5-Cl 2.8 Cl -CH2CH2- 3-Cl 2.9 Cl -CH2CH2- 5-Cl 2.10 Cl-CH2CH2- 5-CF3 2.11 Cl-CH2CH2- 3,5-Cl2 2.12 Cl -CH2CH2- 3-Br, 5-Cl 2.13 Cl -CH2CH2- 3-F, 5-Cl 2.14 Cl -CH2CH2- 3-Cl , 5-CF3 2.15 CF3 H, H 3-Cl 2.16 CF3 H, H 5-Cl 2.18 CF3 H, H 3.5-Cl2 2.19 CF3 H, H 3-Br, 5-Cl 2.20 CF3 H, H 3-F , 5-Cl 2.21 CF3 H, H 3-Cl, 5-CF3 C? OR N > r ro Ni t ro ro ro ro ro ro n > ro N > ro ro ro ro > > ro h '-t * f > > 4 ^ 4 ^? »^? ? ? w? w? ? 00 00 ro ro ro fo fo O) n • ^ 00 N > or CD oo - i to Oí 4 ^? > O D 00 O) OÍ ^ > 4 ^ oo faith ffi ffi ffi ffi 1 I o o o? ooo ffi ffi ffi ffi ffi ffi ffi or O or OO oo ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi opopooooooooon ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi -ffi F ffi > C? C? OJ OJ OJ OJ C? < * OJ OJ OJ OJ OJ C? C? OJ OJ OJ OJ OJ C? n OJ X p? Q? T? ? or Ó? Ti? O | H Ó p p? T? !? IT ? or? a _ * C? Q TI * - * C? O T 1 l 1 'C? u T »il '' C? ß- "C? < r? Q? o Q O O Ti Q T Q? n TI Q I heard oo or VO OJ or O 2. 47 CF3 H, H 3-Br, 5-Cl 2. 48 CF3 H, H 3-F, 5-Cl 2. 49 CF3 H, H 3-Cl, 5-CF3 2. 50 CF3 -CH2CH2- 3-Cl 2. 51 CF3 -CH2CH2- 5-Cl 2.53 CF3 -CH2CH2- 3,5-Cl2 2. 54 CF3 -CH2CH2- 3-Br, 5-Cl 2. 55 CF3 -CH2CH2- 3-F, 5-Cl 2. 56 CF3 -CH2CH2- 3-Cl, 5-CF3 Table 3 or. Ri R2 R3, 4 (R5) m Physical data .1 Cl CH3 H, H 5-CF3 .2 Cl CH3 H, H 3.5-Cl2 .3 Cl CH3 H, H3-Cl, 5-CF3 3.4 Cl CH3 -CH2CH2- 5-CF3 3.5 Cl CH3 -CH2CH2- 3,5-Cl2 3.6 Cl CH3 -CH2CH2- 3-Cl, 5-CF3 3.7 Cl C2H5 H, H 5-CF3 3.8 Cl C2H5 H, H 3.5-Cl2 3.9 Cl C2H5 H, H 3-Cl, 5-CF3 Cl C2H5 -CH2CH2- 3.10 5-Cl C2H5 -CH2CH2- 3.11 CF3 3,5-Cl2 3.12 Cl C2H5 -CH2CH2- 3-Cl, 5-Cl 3.14 CF3 COCH3 H , H 3.5-Cl2 3.15 Cl COCH3 H, H 3-Cl, 5-CF3 3.16 Cl COCH3 -CH2CH2- 5-CF3 3.17 Cl COCH3 -CH2CH2- 3,5-Cl2 K (or J OJ OJ J OJ OJ k OJ > k > > io tO O 00 O O O O O O O C O O O O O O O O O O O O O O n p O ffi ffi ffi ff ffi I on O ffi i O oo ffi fif ffi ooo ffi ffi ffi or O or ffi ffi ffi ot ffio t ffio (ffio ffi ffi ffi l ffio t ffio t ffio ffi ffi ffi l ffi t ffi t ffio ffi ffi ffi t ffio t ffi ffi ffio t ffio ffi ffio ooo t O t O onopnopo ffio ffio t t t ffi ffi ffi ffio t t t ffio ffio ffio t t t ffio ffi f 1 t ffio ffio O o O O O O O O O O O O O O O o O ci O O O O n O O O O TI Tj TJ J Tj O O a O O O O O O O O O O O p O O O O O O O O O O ffi ffi ffi ffi ffi ffi Q 0 or O Q O O O O O O O O O O O O O O O O O O O O O O O O O O i ffi O O O O O O O O * °. o O ffi ffi ffi ffi ffi ffi • > > , o ff ffi ffi ffi ffi ffi ffi O O O O O T uT oT oT ffi ffi ffi ffi ffi ffi ffi O oo ffi ffi ffi O p ffi ffi ffi OOO o ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi m ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi oooooooo OOOO ffi ffi ffi ffi ffi ffi ffi & ffi ffi ffi ffi 1 Ul 1 O O J o O | p O o o p? | O O "H O O O O" H O Or p. 'Q > - * O TJ p ¿~ 'O TJ ¿-1 Q T), r- O TJ Ó O O O UNCLE TJ Ój? O TJ TJ OR OJ OJ OH O O 0 ro UO t ^ - s. fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi fi ffi ffi "ffi" u u u ffi "ffi" ro ro r ro ro r ro r ro ro r ro ro ro ro ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi e ffi ffi ffi ffi ffi ffi ffi ffi ffi B ffi ffi OR ? U U U U U U U U U U U U U U U U U U u u 00 sv or (ro • * uo VO t "- 00 sv or C r • T o vo t oo sv o T? VO vo t- ^ t-; t-; t t? t-; 1 t ~; t- ^ 00 oo oo oq 00 00 oo 00 oo 00 sv sv sv ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro or rs 3. 93 CF3 COOC2H5 H, H 3-Cl, 5-CF3 3. 94 CF3 COOC2H5 -CH2CH2- 5-CF3 3. 95 CF3 COOC2H5 -CH2CH2- 3,5-Cl2 3. 96 CF3 COOC2H5 -CH2CH2- 3-Cl, 5-CF3 3. 97 CF3 COOC6H5 H, H 5-CF3 3. 98 CF3 COOC6H5 H, H 3.5-Cl2 3. 99 CF3 COOC6H5 H, H 3-Cl, 5-CF3 3. 100 CF3 COOC6H5 -CH2CH2- 5-CF3 3. 101 CF3 COOC6H5 -CH2CH2- 3,5-Cl2 3. 102 CF3 COOC6H5 -CH2CH2- 3-Cl, 5-CF3 3. 103 CF3 COOCH2C6H5 H, H 5-CF3 3. 104 CF3 COOCH2C6H5 H, H 3.5-Cl2 3. 105 CF3 COOCH2C6H5 H, H 3-Cl, 5-CF3 3. 106 CF3 COOCH2C6H5 -CH2CH2- 5-CF3 3. 107 CF3 COOCH2C6H5 -CH2CH2- 3,5-Cl2 3. 108 CF3 COOCH2C6H5 -CH2CH2- 3-Cl, 5-CF3 3. 109 CF3 COC6H5 H, H 5-CF3 3. 110 CF3 COC6H5 H, H 3.5-Cl2 3. # 3. 190 CF3 C2H5 -CH2CH2- 5-CF3 3. 191 CF3 C2H5 -CH2CH2- 3,5-Cl2 3. 192 CF3 C2H5 -CH2CH2- 3-Cl, 5-CF3 3.193 CF3 COCH3 H, H 5-CF3 3. 194 CF3 COCH3 H, H 3.5-Cl2 3. 195 CF3 COCH3 H, H 3-Cl, 5-CF3 3. 196 CF3 COCH3 -CH2CH2- 5-CF3 3. 197 CF3 COCH3 -CH2CH2- 3,5-Cl2 3. 198 CF3 COCH3 -CH2CH2- 3-Cl, 5-CF3 3. 199 CF3 CH2C6H5 H, H 5-CF3 3. 200 CF3 CH2CóH5 H, H 3.5-Cl2 3. 201 CF3 CH2C6H5 H.H 3-Cl, 5-CF3 3. 202 CF3 CH2C6H5 -CH2CH2- 5-CF3 3. 203 CF3 CH2C6H5 -CH2CH2- 3,5-Cl2 3. 204 CF3 CH2C6H5 -CH2CH2- 3-Cl, 5-CF3 3. 205 CF3 CH2OC2H5 H, H 5-CF3 3. 206 CF3 CH2OC2H5 H, H 3.5-Cl2 3. 207 CF3 CH2OC2H5 H, H 3-Cl, 5-CF3 3. 208 CF3 CH2OC2H5 -CH2CH2- 5-CF3 3. 209 CF3 CH2OC2H5 -CH2CH2- 3,5-Cl2 3. 210 CF3 CH2OC2H5 -CH2CH2- 3-Cl, 5-CF3 3. 211 CF3 COOC2H5 H, H 5-CF3 3. 212 CF3 COOC2H5 H, H 3.5-Cl2 3. 213 CF3 COOC2H5 H, H 3-CL 5-CF3 3. 214 CF3 COOC2H5 -CH2CH2- 5-CF3 3. 215 CF3 COOC2H5 -CH2CH2- 3,5-Cl2 3. 216 CF3 COOC2H5 -CH2CH2- 3-Cl, 5-CF3 3. 217 CF3 COOC6H5 H, H 5-CF3 rs rs < s rs < N rs rs ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi u o f ffi ffi. ° * O rs u rS u c u ts u O, < ? (SO cs u < s O < S ffi fi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi "ffi? Ou ffi" ffi ffi "uuo ffi" ffi "ffi ouu ffi "ffi" ffi "O uu *. ffi vo ffi vo ffi ffi ffi vo ffi vo wo * n wo u u u u ffi ffi ffi ffi ffi ffi ffi ff ffi i rs oi ff ffi rs tf ffi ffi tf ffi ffi O uu ? u O uu U ou ffi fi ffi tf ffi U tf U TJ ffi uJ uu • of fi ooooo O oo O oooouu? Pi wfu J? zzzz jooooooooooooooooo oO or O oouou? uouuuuuuu? uoouuu ü ou ro ro ro ro r ro ro ro ro ro ro ro ro ro ro ro ro ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi or OU or U or O u OO u? u U uu U? OO & UO 00 sv o CN ro "* o VO r- 00 sv o (N ro« * uo vo t-- oo sv o (N i ro ro ro ro ro ro ro ro ro o • < fr < < CN CN < < ~ 1 < CN CN < N CN cN (N if CN < ~ < N < (< < N CN Cv < N CN < C N ro 3. Activity on phytotoxic mites Tetranychus urticae sensitive to OP The primary leaves of bean plants (Phaseolus vulgaris) are covered 16 hours before the test with a piece grown in leaf mass infested with T. urticae. After removing the piece of leaf, the plants that are infested with all stages of the mites, are sprayed to the point of dripping with a test solution containing 0.2, 0.4, or 1.6 ppm of the compound that is going to try. The temperature in the greenhouse is approximately 25 ° C. After 7 days, an evaluation is made of the percentage of mobile stages (adults and nymphs) and eggs under a microscope. The compounds of the formula I achieve a total mortality at a concentration of the active ingredient of 0.4 ppm. 4. Activity on Lucilia sericata Li larvae One milliliter of an aqueous suspension of the active substance to be tested is mixed with 3 milliliters of a special larval culture medium at approximately 50 ° C, in such a way as to obtain a homogenate of 250 or 125 ppm of active ingredient. Approximately 30 Luci lia (Lx) larvae are used in each sample of each test tube. After 4 days, the mortality rate is determined. The compounds of the formula I reach a 100 percent activity with 250 ppm. 5. Acaricidal activity on Boophilus microplus (Biarra strain) A piece of sticky tape is attached horizontally to a PVC sheet, so that 10 female ticks, fully sated from Boophilus micro-plus (Biarra strain), can adhere to it by their loins , side by side, in a row. Using a needle for injection, one microliter of a liquid is injected into each tick. The liquid is a 1: 1 mixture of polyethylene glycol and acetone, and contains, dissolved in it, a certain amount of active ingredient selected from 1, 0.1, or 0.01 micrograms per tick. The control animals are given an injection with no active ingredient. After treatment, the animals are kept under normal conditions in an insectarium at approximately 28 ° C and 80% relative humidity, until oviposition takes place, and the larvae of the eggs of the control animals hatch. The activity of a tested substance is determined by IR90, that is, an evaluation is made of the dosage of the active ingredient in which 9 out of 10 female ticks (= 90 percent) lay eggs that are infertile even after 30 days. The compounds of the formula I reach an IR90 of 0. 1 micrograms. 6. Efficacy in vi tro on Boophilus microplus satiated females (BIARRA); 4 x 10 female ticks sated from the OP-resistant BIARRA strain are adhered to a sticky tape, and covered for 1 hour with a cotton swab soaked in an emulsion or suspension of the test compound in concentrations of 500, 125, 31, and 8 ppm, respectively. The evaluation takes place 28 days later, based on mortality, oviposition, and hatched larvae.

An indication of the activity of the test compounds is shown by the number of females that: die quickly before laying eggs, survive for some time without laying eggs, lay eggs where embryos do not form, lay eggs where embryos are formed , of those that do not hatch larvae, and lay eggs where embryos are formed, from which larvae usually hatch within 26 to 27 days. In this test, the compounds of formula I effect a rapid mortality greater than 80 percent of female ticks. 7. Action by contact on Aphis craccivora The pea seedlings that have been infested with all the stages of development of the aphids, are sprayed with a solution of the active ingredient prepared from an emulsion concentrate, containing the solution 50, 25, or 12.5 ppm of active ingredient, as desired. After 3 days, an evaluation is made of more than 80 percent of the aphids that are dead or that have fallen. Only at this level of activity is a preparation classified as effective. The compounds of formula I achieve a total mortality (= 100 percent) at a concentration of 12.5 ppm. 8. Larvicidal Activity on Aedes aegypti A sufficient amount of an acetonic solution is added to 0.1 percent of the active ingredient for a selected concentration of 10, 3.3, or 1.6 ppm, by pipette, to the surface of 150 milliliters of water in a container. After evaporation of the acetone, the container is covered with approximately 30 to 40 3-day-old Aedes larvae. After 1, 2, and 5 days, mortality is tested. In this test, the compounds of the formula I, at a concentration of 1.6 ppm, effect a complete mortality of all the larvae after only one day. 9. Effectiveness. In vivo on adult Ctexioceph.alld.es fells in domestic cats after oral treatment Test substances are given orally to domestic cats in a gelatin capsule before or after feeding, varying the dose between 0.5 and 20 milligrams /kilogram. On days 1, 3, 7, and 10 after treatment, each cat is exposed to 100 fleas (approximately 50 males and approximately 50 females), depending on the result of previous flea colonization. The effectiveness (in percentage of reduction in the number of fleas) is based on the number of live fleas found after combing for 10 minutes one day after the other to the new flea colonization, where the efficiency in percentage corresponds to the arithmetic average of the number of live fleas in the control animals minus the number of live fleas in the treated animals, divided by the arithmetic average of the number of live fleas in the control animals and multiplied by 100. The dying fleas found in the cages of the cats are collected by combing, they are placed in an incubator at 28 ° C and with 70% relative humidity, and after 24 hours, they are tested to determine their survival / mortality. If most dying fleas die, the test compound is considered a flea adulticide, and if the majority survive, the test compound shows a "knock down" activity. In this test, the compounds of the formula I effect a mortality of at least 80 percent of the fleas. 10. Efficacy in vivo on adult Ctenocephalides felis in domestic cats after their exact treatment Test substances are given to domestic cats as an applied treatment, varying the dose between 0.5 and 10 milligrams / kilogram. On days 1, 3, 7, and 10 after treatment, each cat is exposed to 100 fleas (approximately 50 males and approximately 50 females), depending on the result of previous flea colonization.

The effectiveness (in percentage of reduction in the numbers of fleas) is based on the number of live fleas found after combing for 10 minutes a few days after each new colonization of fleas, whereby, the effectiveness in percentage corresponds to the average arithmetic of the number of live fleas in the control animals minus the number of live fleas in the treated animals, divided by the arithmetic average of the number of live fleas in the control animals and multiplied by 100. The dying fleas found in the Cats of cats and by combing are collected, placed in an incubator at 28 ° C and with 70 percent relative humidity, and after 24 hours, tested to determine their survival / mortality. If most dying fleas die, the test compound is considered a flea adulticide, and if the majority survive, the test compound shows a "knock down" activity. In this test, the compounds of formula I effect a mortality greater than 90 percent of the fleas after 35 days. 11. Efficacy in vitro on nymphs of Amblyomma hebraeum Approximately 5 fasting nymphs are placed in a polystyrene test tube containing two milliliters of the test compound in solution, suspension, or emulsion.

After immersion for 10 minutes, and stirring for 10 seconds twice in a vortex mixer, the test tubes are blocked with a tight cotton napkin, and rotated. As soon as all the liquid has been soaked in the cotton wool ball, it is pushed halfway into the test tube that is still spinning, so that most of the liquid from the wool ball is squeezed out. of cotton and flow to a Petri dish below. Then the test tubes are kept at room temperature in a room with daylight, until they are evaluated. After 14 days, the test tubes are immersed in a beaker with boiling water. If the ticks begin to move in reaction to heat, the test substance is inactive at the tested concentration, and otherwise, the ticks are considered dead, and the test substances are considered active at the tested concentration. All substances are tested in a concentration range of 0.1 to 100 ppm. In this test, the compounds of the formula I effect a mortality greater than 80 percent of the ticks. 12. Activity with ra Dermanyssus gallinae Add 2 to 3 milliliters of a solution containing 10 ppm of active ingredient, and approximately 200 mites (Dermanyssus gallinae) in different stages of development, to a glass container that is open in the top The container is then closed with a cotton wool cotter, stirred for 10 minutes until the mites are completely wet, and then inverted briefly, so that remaining test solution can be absorbed by the cotton wool. After 3 days, the mortality of the mites is determined by counting the dead individuals, and it is indicated as a percentage. The compounds of formula I show a good activity against Dermanyssus gallinae. 13. Activity against Musca domestica A sugar cube is treated with a solution of the test substance in such a way that the concentration of the test substance in the sugar, after drying overnight, is 250 ppm. The cube treated in this way is placed on an aluminum plate with wet cotton wool and 10 adult Musca domestica from an OP resistant strain, covered with a beaker, and incubated at 25 ° C. The mortality rate is determined after 24 hours. In this test, the compounds of formula I show good activity against Musca domestica.

Claims

CLAIMS Compounds of the formula: wherein: Ri is hydrogen, halogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, or unsubstituted or mono- to penta-substituted phenyl, wherein the substituents are selected from the group comprising alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, aryloxy, halogen, cyano, and nitro, wherein, if the number of substituents is greater than one, the substitutes can be identical or different; R 2 is hydrogen, C 1 -C 6 alkenyl, (C 1 -C 6 -alkylene) phenyl, pyridyl, COOR 6, CONR 7 R 8, COR 6, allyl, or CH 2-0-R 6; Xi is N; X2 is C (CN), C (COOR6), C (COR6), C (SOR6), C (CONR7R8) or C (N02); X3 is O or S; Q is CH or N; R-3 and R independently of one another, are hydrogen, alkyl of 1 to 6 carbon atoms, or together with the carbon atom to which they are attached, a cycloalkyl ring of 3 to 7 carbon atoms; R5 is a substituent from the group comprising alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, aryloxy, halogen, cyano, hydroxyl, amino, nitro, and mono- to penta-substituted phenyl, wherein the substituents are selected from the group comprising alkyl of 1 to 6 carbon atoms, alkenyl from 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, aryloxy, halogen, cyano, hydroxyl, amino, and nitro, and if the number of phenyl substituents is greater than one, they may be identical or different, wherein, if m is greater than 1, the substituents R5 may be identical or different; R6 is alkyl of 1 to 6 carbon atoms, phenyl, or benzyl; R-7 and R-8 / independently of each other, are hydrogen or alkyl of 1 to 6 carbon atoms; m is 1, 2, or 3; and n is 0 or 1. 2. A process for the preparation of compounds of the formula I according to claim 1, wherein a compound of the formula: which is known or can be produced in a manner analogous to the corresponding known compounds, and wherein R1 t R2, i / and 2 are defined as given for formula I, is reacted with a compound of the formula: which is known or can be produced in a manner analogous to the corresponding known compounds, wherein X3, R3, R4, R5, m, n, and Q are defined as for formula I, and Z is a leaving group, optionally in the presence of a basic catalyst, and if desired, a compound of formula I that can be obtained by this process or otherwise, or an enantiomer thereof, can be converted to another compound of formula I or an enantiomer of the same; a mixture of enanti-mers that can be obtained by this process is separated, and the desired enantiomer is isolated. 3. A composition for the control of pests, which contains, as an active ingredient, at least one compound of the formula I according to claim 1, in addition to vehicles and / or dispersants. 4. The use of compounds of the formula I according to claim 1, in the control of pests. 5. A method for controlling pests, wherein a pesticidally active amount of at least one compound of the formula I according to claim 1 is used on the pests or on the locus thereof. 6. The use of a compound of the formula I according to claim 1, in a process for controlling parasites in warm-blooded animals. 7. The use of a compound of the formula I according to claim 1, in the preparation of a pharmaceutical composition against parasites.