MXPA06010201A - Use of pyrimidine compounds in the preparation of parasiticides - Google Patents

Abstract

The invention relates to the use of compounds of the general formula (I), wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11,R12, R13, X1 and X2 have the significances given in claim 1, and optionally the enantiomers and geometrical isomers thereof, for controlling parasites on warm-blooded animals.

Description

USE OF PIRIM1D1NA COMPOUNDS IN THE PREPARATION OF PARASITICIDES The present invention relates to the use of 4,6-disubstituted 5-amino-pyrimidine compounds of the formula: wherein: Ri is hydrogen, halogen, cyano, OH, SH, NO2, COOH, COOR2, CONH2, CON R2R3, SO3H, SO2NR2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, halo-alkenyloxy of 2 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyloxy, haloalkyl of 1 to 6 carbon atoms-sulfonyloxy , alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms carbon-sulfinyl, alkoxy of 1 to 6 carbon atoms or sulfonyl, haloalkyl of 1 to 6 carbon-sulfonyl atoms, thioalkyl of 2 to 6 carbon atoms, halo-thioalkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon-sulfinyl atoms, haloalkyl of 2 to 6 carbon atoms-sulfinyl, alkenyl of 2 to 6 carbon atoms-sulfonyl, halo-alkenyl of 2 to 6 atoms carbon atoms-their lfonyl, N R2R3, unsubstituted or substituted aryl one to five times, or unsubstituted or substituted hetaryl, substituents being selected from the group consisting of halogen, cyano, OH, SH, NO2, COOH, COOR2, CON H2, CON R2R3, SO3H, SO2N R2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo-alkoxy of 1 to 6 carbon atoms , alkenyl of 2 to 6 carbon atoms, halo-alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms bond, haio-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, halo-alkenyl oxyl of 2 to 6 carbon atoms carbon, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyloxy, haloalkyl of 1 to 6 carbon atoms-sulfonyloxy, alkyloyl 1 to 6 carbon atoms - sulfinyl, haloalkyl of 1 to 6 carbon atoms - sulfinyl, alkyl of 1 to 6 carbon atoms - sulfonyl, haloalkyl of 1 to 6 carbon atoms - sulfonyl, thioalkenyl of 2 to 6 carbon atoms, halo-thioalkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon-sulfinyl atoms, haloalkyl of 2 to 6 carbon-sulfinyl atoms, alkenyl of 2 to 6 carbon-sulfonyl atoms, halo-alkenyl of 2 to 6 carbon atoms -sulfonyl, and N R2R3; R2 and R3, independently of one another, mean hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, formyl, alkyl of 1 to 6 carbon atoms, carbonyl, haloalkyl of 1 to 6 carbon atoms-carbonyl, alkoxy of 1 to 6 carbon atoms-carbonyl, halo-alkoxy of 1 to 6 carbon atoms-carbonyl, alkyl of 1 to 6 carbon atoms-amino-carbonyl, di-alkyl of 1 to 6 carbon atoms-amino-carbonyl, or substituted or unsubstituted benzyl of one to five times, the substituents being selected from the group consisting of halogen, cyano, OH, SH, NO2, COOH, COOR2, CON H2, CON R2R3, SO3H, SO2N R2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, halo-alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, allo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, halo-alkenyloxy of 2 to 6 carbon atoms, thioalkyl from 1 to 6 carbon atoms, halo-, thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyloxy, haloalkyl of 1 to 6 carbon atoms- sulfonyloxy, alkyl of 1 to 6 carbon atoms-sulfinyl, alkyl alkylene of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 atoms of carbon-sulfonyl, thioalkenyl of 2 to 6 carbon atoms, halo-thioalkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms-sulfinyl, haloalkyl of 2 to 6 carbon atoms- sulfinyl, alkenyl of 2 to 6 carbon-sulfonyl atoms, halo-alkenyl of 2 to 6 carbon atoms-sulfonyl; R, Rs, Re, R, Ra, Rg, R-io, Rn, R-? 2 and R13, independently of each other, are hydrogen, halogen, cyano, nitro, OH, SH, NO2, COOH, COOR2, CON H2, CON R2R3, SO3H, SO2N R2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, halo-alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, halo-alkenyloxy from 2 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyloxy, haloalkyl of 1 to 6 carbon atoms- sulfonyloxy, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, tioalqueni 2 to 6 carbon atoms, halo-thioalkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms-sulfinyl, haloalkyl of 2 to 6 carbon atoms-sulfinyl, alkenyl of 2 to 6 carbonsulfonyl atoms, haloalkenyl of 2 to 6 carbon atoms or sulfonyl, alkyls of 1 to 6 carbon atoms, -alkyl of 1 to 6 carbon atoms -amino, alkyl of 1 to 6 carbon atoms-sulfonyl amino, haloalkyl of 1 to 6 carbon atoms-sulphonyl amine, alkyl from 1 to 6 carbon atoms, carbonyl, haloalkyl from 1 to 6 carbon atoms, carbonyl, alkoxyl from 1 to 6 carbon atoms, carbonyl, alkoxy from 1 to 6 carbon atoms -carbonyl, dialkyl of 1 to 6 carbon-amino-carbonyl atoms, aryl unsubstituted or substituted one to five times, or unsubstituted or substituted hetaryl, the substituents being selected from the group consisting of halogen, cyano, OH, SH , N O2, COOH, COOR2, CONH2, CONR2R3, SO3H, SO2NR2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, halo-alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halo-cycloalkyl of 3 to 6 atoms of carbon, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, haloalkenyloxy of 2 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyloxy, haloalkyl of 1 to 6 carbon atoms-sulfonyloxy, alkyou of 1 to 6 carbon atoms-sulfinyl, haloalkyl uilo of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms or sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, thioalkenyl of 2 to 6 carbon atoms, haloalkyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon-sulfinyl atoms, haloalkenyl of 2 to 6 carbon atoms - sulfinyl, alkenyl of 2 to 6 carbon atoms - sulfonyl, haloalkenyl of 2 to 6 carbon atoms - sulfonyl, and N R2R3; Xi and X2, independently of each other, are C (R14) (R-? 5), N R14, O, S, SO or SO2; and R 14 and R 15, independently of one another, mean hydrogen, alkyl of 1 to 6 carbon atoms, formyl, alkyl of 1 to 6 carbon atoms-carbonyl, or halo-alkyl of 1 to 6 carbon atoms-carbonyl; in the control of ectoparasites, especially ticks, in non-human animals, especially in producing cattle and domestic animals, as well as pesticide compositions containing at least one of these compounds. In the literature, for example in International Publications Nos. WO9854154, WO0049001, WO0224663, or in U.S. Patent No. U S6342499, different compounds have been proposed as active ingredients having pesticidal properties. However, the biological properties of these known compounds are not completely satisfactory in the field of pest control, and is the reason why there is a need to produce additional compounds with pesticidal properties, especially for the control of ectoparasites; this problem is solved according to the invention, with the use of the present compounds I.

Alkyl - as a group by itself and as a structural element of other groups and compounds, such as haloalkyl, alkylamino, alkoxy, thioalkyl, alkylsulfinyl, and alkylsulfonyl - is, in each case with the appropriate consideration of the specific number of carbon atoms in the group or compound in question, whether straight chain, ie methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, or octyl, or branched chain, for example isopropyl, isobutyl, secondary butyl, tertiary butyl, isopentyl, neopentyl, or isohexyl. Cycloalkyl - as a group by itself and as a structural element of other groups and compounds, such as halocycloalkyl, cycloalkoxy, and cyclothioalkyl - is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl. Alkenyl - as a group by itself and as a structural element of other groups and compounds - is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question, and of the conjugated double bonds or isolated, either straight chain, for example allyl, 2-butenyl, 3-pentenyl, 1-hexenyl, 1-heptenyl, 1,3-hexadienyl, or 1,3-octadienyl, or branched chain, eg isopropenyl isobutenyl, isoprenyl, tertiary pentenyl, isohexenyl, isoheptenyl, or iso-octenllo. Alkynyl - as a group by itself and as a structural element of other groups and compounds - is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question, and of the conjugated double bonds or isolated, either straight chain, for example propargyl, 2-butynyl, 3-pentynyl, 1-hexynyl, 1-heptynyl, or 3-hexen-1-ynyl, or 1,5-heptadien-3-ynyl, or branched chain, for example 3-methylbut-1-ynyl, 4-ethylpent-1-ynyl, 4-methylhex-2-ynyl, or 2-methylhept-3-ynyl. Arllo is phenyl or naphthyl. Hetaryl is pyridyl, pyrimidyl, s-trlazinyl, 1,4-triazinyl, thienyl, furanyl, pyrryl, plrazolyl, imidazolyl, thiazolyl, triazolyl, oxazolyl, thiadlazolll, oxadiazolyl, benzotilenyl, benzofuranyl, benzothiazolyl, indolyl, or indazolyl, preferably pyridyl, pyrimidyl, pyrryl, imidazolyl, or furanyl, in particular pyridyl or pyrimidyl. As a rule, halogen means fluorine, chlorine, bromine, or iodine. The same applies to halogen in combination with other meanings, such as haloalkyl. The carbon-containing groups and compounds substituted by halogen may be partially halogenated or perhalogenated, wherein, in the case of multiple halogenation, the halogen substituents may be identical or different. The halo-alkyl examples - as a group by itself and as a Structural elements of other groups and compounds, such as haloalkoxy or halo-thioalkyl, are methyl which is mono- to tri-substituted by fluorine, chlorine and / or bromine, such as CHF2 or CF3; ethyl which is mono- to penta-substituted by fluorine, chlorine and / or bromine, such as CH2CF3, CF2CF3, CF2CCI3, CF2CHCI2, CF2CH F2, CF2CFCI2, CF2CH Br2, CF2CHCI F, CF2CH BrF or CCIFCHCIF; propyl or isopropyl which is mono- to hepta-substituted by fluorine, chlorine and / or bromine, such as CH2CH BrCH2Br, CF2CH FCF3, CH2CF2CF3, or CH (CF3) 2; butyl or one of its isomers, which is mono- to nona-substituted by fluorine, chlorine and / or bromine, such as CF (CF3) CH FCF3 or CH2 (CF2) 2CF3; pentylb or one of its isomers, which is substituted one to eleven times by fluorine, chlorine and / or bromine, such as CF (CF3) (CHF) 2CF3 or CH2 (CF2) CF3; and hexyl or one of its isomers, which is substituted one to thirteen times by fluorine, chlorine and / or bromine, such as (CH2) 4CH BrCH2Br, CF2 (CHF) 4CF3, CH2 (CF2) 4CF3, or C (CF3) 2 (CH F) 2CF3. Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Alcoxyl is, for example, methoxyl, ethoxy, propoxy, isopropoxy, normal butoxy, isobutoxy, secondary butoxyl, and tertiary butoxy, as well as the pentyloxy and hexyloxy isomers; preferably methoxy and ethoxy. The halo-alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Haloalkoxy is, for example, fluoro-methoxy, difluoro-methoxy, trifluoromethoxy, 2,2,2-trifluoro-ethoxy, 1,1-2,2-tetrafluoro-ethoxy, 2-fluoro-ethoxy, 2- chloro-ethoxy, 2,2-d-fluoro-ethoxy, and 2,2,2-trichloro-ethoxy; preferably difluoro- methoxy, 2-chloro-ethoxy, and trifluoro-methoxy. The preferred modalities, within the scope of the invention, are: (1) A com ponent of formula I, wherein: Ri is hydrogen, halogen, NO2, alkyl of 1 to 6 carbon atoms, halo- alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo-alkoxyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy from 3 to 6 carbon atoms, clclothioalkyl of 3 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, or halo-thioalkyl of 1 to 6 carbon atoms, or unsubstituted or substituted aryl of one to five times or unsubstituted or substituted hetaryl; in particular hydrogen, halogen, N O 2, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or haloalkoxy of 1 to 6 carbon atoms; in particular hydrogen, alkyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms; (2) A compound of the formula I, wherein: R2 and R3, independently of one another, mean hydrogen, alkyl having from 1 to 6 carbon atoms, formyl, alkyl having from 1 to 6 carbon atoms, carbonyl, 1 to 6 carbon atoms-carbonyl, alkyl of 1 to 6 carbon atoms-amino-carbonyl, dialkyl of 1 to 6 carbon atoms-amino-carbonyl, or benzyl unsubstituted or substituted one to five times; in particular, independently of one another, hydrogen, alkyl of 1 to 4 carbon atoms, formyl, alkyl of 1 to 4 carbon-carbonyl atoms, or benzyl; in particular, independently of one another, hydronogen, alkenyl of 1 to 2 carbon atoms, or formyl, or benzyl; (3) A compound of the formula I, wherein: R j R £ R £ R7, R £ R < River, . i -? 3 independently from each other, are hydrogen, halogen, cyano, nitro, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, or unsubstituted or substituted aryl from one to five times , or substituted or unsubstituted heteroaryl, especially, independently of one another, hydrogen, halogen, nitro, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms , or halo-alkoxy of 1 to 4 carbon atoms; in particular, independently of one another, hydrogen, halogen, nitro, alkyl of 1 to 2 carbon atoms, or haloalkyl of 1 to 2 carbon atoms; more preferably, independently of one another, hydrogen, halogen, nitro, or CF3; (4) A compound of formula I, where: X-i and X2, independently of one another, are NR14, O, or S; especially, independently of one another, N H, O, or S; in particular, O; (5) A compound of the formula I, wherein: -14 and i5, independently of one another, mean hydrogen, alkyl of 1 to 4 carbon atoms, formyl, alkyl of 1 to 4 carbon atoms-carbonyl; in particular, independently of one another, hydrogen or alkyl of 1 to 4 carbon atoms; in particular, hydrogen; (6) A compound of formula I, wherein: RT is hydrogen, halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo -alcoxyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, or halo-thioalkyl of 1 to 6 carbon atoms; R2 and R3, independently of one another, mean hydrogen, alkyl of 1 to 6 carbon atoms, formyl, alkyl of 1 to 6 carbon atoms-carbonyl, alkoxy of 1 to 6 carbon atoms-carbonyl, alkyl of 1 to 6 carbon-amino-carbonyl, dialkyl of 1 to 6 carbon atoms-amino-carbonyl, or benzyl; R4, R5, R6, R7, R8, R9, R10, R1 1,? 2 and R131 independently of one another, they are hydrogen, halogen, cyano, nitro, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6. carbon atoms, cycloalkyl of 3 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, or aryl unsubstituted or substituted one to five times, or unsubstituted or substituted hetaryl; Xi and X2, independently of one another, are NR14, O, or S; and R-? means hydrogen, alkyl of 1 to 4 carbon atoms, formyl, alkyl of 1 to 4 carbon atoms, carbonyl; (7) A compound of formula I, wherein: R-, is hydrogen, halogen, NO2, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms carbon, or halo-alkoxy of 1 to 6 carbon atoms; R2 and R3, independently of one another, mean hydrogen, alkyl of 1 to 4 carbon atoms, formyl, alkyl of 1 to 4 carbon atoms, or unsubstituted or substituted benzyl of one to five times; R, R5, R6, R, Ra, R9, R10, 111? 2 and R-13, independently of one another, are hydrogen, halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms. carbon, alkoxy of 1 to 4 carbon atoms, or haloalkoxy of 1 to 4 carbon atoms; and XT and X2, independently of one another, are NH, O, or S; (8) A compound of the formula I, wherein: RT is hydrogen, alkyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms; R2 and R3, independently of one another, mean hydrogen, alkyl of 1 to 2 carbon atoms, or formyl; R 4, R 5, R 6, R, R 3, R 9, R-io, R 11, R 2 and R 13. independently of one another, they are hydrogen, halogen, NO2, alkyl of 1 to 2 carbon atoms, or haloalkyl of 1 to 2 carbon atoms; and X1 and X2 are O; (9) A compound of the formula I, wherein: Ri is hydrogen, alkyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms; R2 and R3, independently of one another, mean hydrogen, alkyl of 1 to 2 carbon atoms, or formyl; R4 s. Re,? > s, 9, R 10, R 11, R 2 and R 13, independently of one another, are hydrogen, fluorine, or CF 3; Y Within the context of the invention, a particular preference is given to the compounds of the formula I listed in Table 1, and more particularly to those named in the synthesis examples. The compounds of formula I of the present invention, in free form or in salt form, respectively, can be prepared by a process, for example characterized in that a compound of the formula is reacted: which is known or can be produced in a manner analogous to the corresponding known compounds, and wherein Ri, R2, and R3 are defined as given for formula I, and Q, and Q2 are leaving groups, with a compound of the formula: which is known or can be prepared in a manner analogous to the corresponding known compounds, and wherein R, s, Re, R7, Rs, and X2 are defined as given for formula I, and the intermediate is subsequently reacted or at the same time with a compound of the formula: which is known or can be prepared in a manner analogous to the corresponding known compounds, and wherein R9, R10, R1 1, R? 2, R13, and X? they are defined as given for formula I, and if desired, a compound of formula 1 that can be obtained according to the method or otherwise, respectively in free form or in salt form, is converted to another compound of formula I; a mixture of isomers obtainable according to the method is separated and the desired isomer is isolated; and / or a free compound of the formula I obtainable according to the method is converted into a salt, or a salt of a compound of the formula I obtainable according to the method becomes the free compound of the formula I or in another salt. What has been mentioned above for the salts of the compounds I, is also applied in a manner analogous to the salts of the starting materials listed hereinabove and hereinafter. The reaction components can be reacted with each other as such, that is, without the addition of a solvent or diluent, for example in the melt. However, in most cases, it is convenient to add an inert solvent or diluent, or a mixture thereof. Examples of these solvents or diluents 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, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxy diethyl ether, tetrahydrofuran, or dioxane; ketones, such as acetone, methyl ethyl ketone, or methyl isobutyl ketone; amides, such as N, N-d-methyl-formamide, N, N-diethylformamide, N, N-dimethylacetamide, N-methyl-pyrrolidone, or hexamethyl-phosphoric acid triamide; nitriles, such as acetonitrile or propionitrile; and sulfoxides, such as dimethyl sulfoxide. N, N-dimethylformamide, N-methyl-pyrrolidone, or tetrahydrofuran are preferred. The preferred leaving groups Q are halogens, especially chlorine. Suitable bases for facilitating the reaction are, for example, alkali metal or alkaline earth metal hydroxides, hydrides, amides, alkanolates, acetates, carbonates, dialkyl amides, or alkyl silylamides; alkyl-amines, alkylene diamines, optionally N-alkylated, optionally unsaturated, cycloalkylamines, basic heterocycles, ammonium hydroxides, as well as carbocyclic amines. Those which may be mentioned by way of example are hydroxide, hydride, amide, methanolate, acetate, and sodium carbonate; terbutanolate, hydroxide, carbonate, and potassium hydride; di-isopropyl amide lithium, bis- (trimethylsilyl) -amide of potassium, calcium hydride, trilethyl amine, di-isopropyl-ethyl-amine, triethylene-d-amine, cyclohexyne-mine, N -cyclo-exine I- N, N -dimethyl-amine, N, N-diethyl-aniline, pyridine, 4- (N, N-dimethylamino) -pyridine, qulnuclidine, N-methyl-morpholine, benzyltrimethyl hydroxide -ammonium, as well as 1,5-diazabicyclo [5.4.0] -undec-5-ene (DBU). Sodium hydride or potassium carbonate is preferred. The reaction conveniently takes place in a temperature range from about 60 ° C to about 120 ° C, preferably from about 80 ° C to about 100 ° C. The salts of the compounds I can be produced in a known manner. For example, the acid addition salts of the compounds I can be obtained by treatment with a suitable acid or with an appropriate ion exchange reagent, and the salts with bases can be obtained by treatment with a suitable base or with an appropriate ion exchange reagent. The salts of the compounds I can be converted into the free compounds I by customary means, the acid addition salts, for example, by treatment with a suitable basic composition or with a suitable ion exchange reagent, and the salts with bases, for example, by treatment with a suitable acid or with an appropriate ion exchange reagent. The salts of the compounds I can be converted into other salts of the compounds I in a known manner; the acid addition salts can be converted, for example, into other acid addition salts, for example by treating a salt of an inorganic acid, such as a hydrochloride, with a suitable metal salt, such as a salt of sodium, barium, or silver, of an acid, example with silver acetate, in a suitable solvent in which a resulting inorganic salt, for example silver chloride, is insoluble, and which therefore precipitates out of the reaction mixture. Depending on the method and / or the reaction conditions, the compounds I with salt-forming characteristics can be obtained in free form or in the form of salts. The compounds I can also be obtained in the form of their hydrates, and / or they can also include other solvents used, for example, when necessary, for the crystallization of the compounds present in solid form. The compounds I may optionally be present as optical and / or geometric isomers, or as a mixture thereof.

The invention relates both to the pure isomers and to all possible isomeric mixtures, and is thus to be understood hereinabove and hereinafter, even when the stereochemical details are not specifically mentioned in each case. The diastereoisomeric mixtures of the compounds I, which can be obtained by the process or otherwise, can be separated in a known manner, based on the physicochemical differences of their components, on the pure diastereomers, for example by fractional crystallization, distillation , and / or chromatography. The division of mixtures of enantiomers that can be obtained in accordance with the same, it can be achieved 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 acetyl cellulose, with the assistance of appropriate microorganisms; by dissociation with specific immobilized enzymes; through the formation of inclusion compounds, for example using chiral crown ethers, wherein only one enantiomer forms complex. According to the nvención apart from separation of corresponding isomer mixtures, can also be applied to generally known methods of diastereoselective synthesis or enantioselective for the diastereomers or pure enantiomers, for example by carrying out the method of the invention using educts with the correspondingly appropriate stereochemistry. It is convenient to isolate or synthesize the biologically more active isomer, for example the enantiomer, in the understanding that the individual components have different 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 in particular to the preparation methods described in the examples.

The starting materials and intermediates, which are new and which are used according to the invention for the preparation of the compounds I, as well as their use and process for their preparation, in a similar manner form an object of the invention. The compounds of the formula 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. They are particularly suitable in the control of endo- and ecto-parasites, and to a certain extent also to control endoparasites on and within animals, and in the field of hygiene, while they are well tolerated by warm-blooded animals. In the context of the present invention, it is understood that the ectoparasites are in particular insects, mites (mites and ticks), and crustaceans (sea lice). These include insects of the following orders: Lepidoptera, Coleoptera, Homoptera, Hemiptera, Heteroptera, Diptera, Dictyoptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura, Isoptera, Psocoptera, and Hymenoptera. However, the ectoparasites which may be mentioned in particular are those which trouble humans or animals, or carrying pathogens, for example flies such as Musca domestica, Musca vetustissima, Musca autumnalis, Fannia canicularis, carnaria Sarcophaga, Lucilia cuprina, Hypoderma bovis, Hypoderma lineatum, Chrysomyia chloropyga, Dermatobia hominis, Cochliomyia hominivorax, Gasterophilus intestinalis, Oestrus ovis, biting flies such com Haematobia irritans irritans, Haematobia irritans exigua, Stomoxys calcitrans, horse flies (Tabanidae) with the subfamilies of Tabanidae, such as Haematopota spp. (for example, Haematopota pluvialis) and Tabanus spp. (for example, Tabanus nigrovittatus), and Chrysopsinae such as Chrysops spp. (for example, Chrysops caecutiens); Hypoblasts such as Melophagus ovinus (sheep fly); tsetse flies, such as Glossinia spp; other biting insects such as moths, such as Ceratopogonidae (biting moths), Simuliidae (black flies), Psychodidae (sandflies); but also sucking insects blood, for example mosquitoes, such as Anopheles spp, Aedes spp and Culex spp, fleas, such as Ctenocephalides felis and Ctenocephalides canis (cat flea and dogs), Xenopsylla cheopis, Pulex irritans, Ceratophyllus gallinae, Dermatophilus penetrans , blood sucking lice (Anoplura), such as Linognathus spp., Haematopinus spp, Solenopotes spp, Pediculus humanis, but also chewing lice (Malophagus) such as Bovicola (Damalinia) ovis, Bovicola (Damalinia) bovis, and other Bovico.la spp. Ectoparasites also include members of the order Acariña, such as mites (for example Chorioptes bovis, Cheyletiella spp., Dermanyssus gallinae, Demodex canis, Sarcoptes scabiei, Psoroptes ovis and Psorergates spp., And ticks.) Known representatives of ticks are, for example. , Boophilus, Amblyomma, Anocentor, Dermacentor, Haemaphysalis, Hyalomma, Ixodes, Rhipicentor, Margaropus, Rhipicephalus, Argas, Otobius and Ornithodoros, and the like, which preferably infest warm-blooded animals, including greyish animals, such as cattle, horses, pigs, sheep and goats, poultry, such as chickens, turkeys, guinea fowl and geese, fur animals, such as mink, foxes, chinchillas, rabbits and the like, as well as domestic animals, such as cats and dogs, but also humans. The compounds of formula I according to the invention are also active against all individual stages of development of pests of animals showing normal sensitivity, as well as those showing resistance to widely used parasiticides. This is especially true for insects and members of the order Acariña resistant. The insecticidal, ovicidal and / or acaricidal effect of the active substances of the invention can be manifested directly, that is, annihilating the pests either immediately or after some time has elapsed, for example when the molt occurs, or by destruction of their eggs, or indirectly, for example by reducing the number of eggs laid and / or the hatching rate, a good efficiency corresponding to a pesticide index (mortality) of at least 50 to 60 percent. The compounds of the formula I can also be used against the. hygiene pests, especially in the order of the Diptera of the families Muscidae, Sarcophagidae, Anophilidae, and Culicidae; of the orders O rtópteros, Dictiópteros (for example, of the family Blattidae) (cockroaches), such as Blatella germanica, Blatta orientalis, Periplaneta americana), and H imenoptera (for example, of the families Formicidae (ants) and Vespidae (wasps) )). Surprisingly, the compounds of the formula I are also effective against the ectoparasites of the pesos, especially the subclass of Copepoda (for example of the order of Siphonostognatoida.e (sea lice)), while they are well tolerated by fish. Certain compounds of the formula I also appear to be effective against certain species of helminths. Helminths are commercially important, because they cause serious diseases in mammals and poultry, for example in sheep, pigs, goats, cattle, horses, donkeys, camels, dogs, cats, rabbits, guinea pigs, hamsters, chickens, turkeys, guinea fowl and other farm birds, as well as exotic birds. The typical nematodes: Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostonum, Oesophagostonum, Charbertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, and Parascaris. The trematodes include, in particular, the family of Fasciolideae, especially Fasciola hepatica. The good pesticidal activity of the compounds of the formula I according to the invention corresponds to a mortality index from at least 50 to 60 percent of the pests mentioned, more preferably at a mortality rate greater than 90 percent, and most preferably from 95 to 100 percent. The compounds of the formula I are preferably used internally and externally in an unmodified form, or preferably together with the adjuvants conventionally used in the formulation art, and therefore, can be processed in a known manner to give, by example, liquid formulations (for example, emulsions, suspensions, solutions, emulsifiable concentrates, and concentrates in solution, for greased, poured, or sprayed application), semi-solid formulations (e.g., creams, ointments, pastes, gels, liposomal preparations) ), and solid preparations (e.g., food-additive tablets, including, for example, capsules, powders including soluble powders, granules, embedded from the active ingredient in polymeric substances, similar implants, and microparticles). As with the compositions, the methods of application are selected in accordance with the intended objectives and the prevailing circumstances. The formulation, i.e., the agents, the preparations containing the active ingredient of the formula I, or combinations of these active ingredients with other active ingredients, and optionally a solid, semi-solid, or liquid adjuvant, are produced in a manner known per se, for example by intimate mixing, kneading, or dispersion of the active ingredients with excipient compositions, wherein in consideration of the physiological compatibility of the excipients of the formulation. The solvents in question may be: alcohols (aliphatic and aromatic), such as benzyl alcohol, ethanol, propanol, isopropanol, or butanol; fatty alcohols, such as oleyl alcohol; and glycols and their ethers and esters, such as glycerin, propylene glycol, dipropylene glycol ether, ethylene glycol, ethylene glycol mono-methyl or ethylene ether, and butyl dioxytol; ketones, such as propylene carbonate, cyclohexanone, isophorone or diacetanol alcohol, and polyethylene glycols, such as PEG 300. In addition, the compositions may comprise strong polar solvents, such as N-methyl-2-pyrrolidone, dlmethyl sulfoxide, or dimethylformamide, or water, esters of fatty acids, such as ethyl oleate or isopropyl palmitate, vegetable oils, such as rapeseed, castor oil, coconut, or soybean oil, mono-, di-, triglycerides synthetics such as, for example, glyceryl monostearate and medium chain triglycerides, and also, if appropriate, silicone oils. The mentioned ingredients can also serve as a vehicle for particulate application forms. As an ointment base, i.e., structural building ingredients, the following excipients may be used: Petroleum-based substances, such as petrolatum or paraffins, bases made of wool grease, such as, for example, lanolin or lanolin alcohols , polyethylene glycols such as, for example, macrogols; and lipid bases, such as, for example, phospholipids, or triglycerides, such as hydrogenated vegetable oils. In general, the use of emulsifiers, wetting agents, and extenders, such as lecithin, such as soy lecithin, fatty acid salts with alkaline earth and alkaline metals, alkylsulfates such as cetyl stearyl sulfate, can also be required. sodium, cholates, fatty alcohols such as cetyl alcohol, sterols such as cholesterol, polyoxyethylene sorbitan fatty acid esters such as polysorbate 20, sorbitan fatty acid esters with sorbitan sorbitan laureate, fatty acid esters and ethers of polyoxyethylene alcohols and polyoxyethylene polyoxyethylene copolymers, copolymers of polyoxypropylene-polyoxyethylene blocks, for example P luron icM R, sucrose esters such as sucrose distearate, polyglyceryl fatty acid esters such as oleate of polyglycerol, and esters of fatty acids such as, for example, ethyl oleate or isopropyl myristate. The formulations may also include gelling and hardening agents, such as, for example, poly acrylic acid derivatives, cellulose ethers, vinyl polyvinyl alcohols, polyvinyl pyrrolidones, and fine dispersed silicon dioxide. As polymeric agents with controlled release properties, derivatives made, for example, with polylactic acid, polylactic acid co-glycolic acid, poly-orfo ester, sodium carbonate, can be applied. polyethylene, polyanhydrides and starch, and matrices based on PVC. It may be necessary to add enhancers of the penetration as ketones, sulfoxides, amides, esters of fatty acids, and fatty alcohols. You can also add preservatives such as sorbic acid, benzyl alcohol and parabens, and antioxidants such as, for example, alpha-tocopherol. The active ingredient or combinations of the active ingredient can also be applied in capsules, such as hard gelatin capsules or soft capsules. 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 (for example methyl cellulose, carboxy methyl cellulose, ethyl hydroxy ethyl) cellulose, proteins such as zein, gelatin, and the like), as well as synthetic polymers, such as polyvinyl alcohol, polyvinyl pyrrolidone, etc. The tablets also contain fillers (for example, starch, microcrystalline cellulose, sugar, lactose, etc.), skimmers (eg, magnesium stearate), and disintegrants (eg, cellulose derivatives), and acid resistant coatings, such as, for example, acrylic acid esters . 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 sphere of activity, for example to increase activity, or with substances that have another sphere of activity, for example to expand the activity interval. It may also make sense to add so-called repellents. Because the compounds of the formula I are adulticides, that is, because they are effective in particular against the adult stages of the target parasites, the addition of pesticides that instead attack the juvenile stages of the parasites can be very convenient. In this way, most of the parasites that produce great economic damage will be covered. Moreover, this action will contribute substantially to avoid 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 combination components, and especially preferred combination components are mentioned in the following, wherein the combinations may contain one or more of these components in addition to a compound of formula I. Suitable components in the mixture may to be biocides, for example insecticides and acaricides with different mechanisms of activity, which are mentioned in the following, and have been known to the person skilled in the art for a long time, for example inhibitors of chitin synthesis, regulators of growth; active ingredients that act as juvenile hormones; active ingredients that act as adulticides; broadband insecticides, broad band acaricides, and nematicides; and also the well-known anthelmintics and the substances that keep insects and / or mites away, and the repellents or aforementioned repellents. Non-limiting examples of suitable insecticides and acaricides are: 1. Abamectin 2. AC 303630 3. Acetate 4. Acrynatrin 5. Alanicarb 6. Aldicarb 7. a-cypermethrin 8. Alfamethrin 9. Amitraz 10. Avermectin Bi 11. AZ 60541 12. Azinfos A 13. Azinfos M 14. Azinphos-methyl 15. Azocyclotin 16. Bacillus subtil toxin. 17. Bendiocarb 18. Benfuracarb 19. Bensultap 20. β-Cyfluthrin 21. Bifenthrin 22. BPMC 23. Brofenprox 24. Bromophos A 25. Bufencarb 26. Buprofezin 27. Butocarboxim 28. Butylpyridaben 29. Cadusafos 30. Carbaryl 31. Carbofuran 32. Carbophenothion 33. Cartap 34. Cloetocarb 35. Chloretoxyphos 36. C lorien apy 37. Clorifluzuron 38. Clomorphs 39. Chlorpyrifos 40. Cis-resmethrin 41. Clocitrin 42. Clofentecin 43. Cyanophos 44. Cycloprothrine 45. Cyfluthrin 46. Cyhexatin 47. D 2341 48. Deltamethrin 49. Demeton M 50. Demeton S 51. Demeton-S-methyl 52. Dibutylthioamine 53. Diclofention 54. Dicliphos 55. Diet 10 56. Diflubenzuron 57. Dimethoate 58. Dimethylvinfos 59. Dioxatión 60. DPX-MP062 15 61. Edifenfos 62. Emamectin 63. Endosulfan 64. Esfenvalerate 65. Etiofencarb 66. Etión 67. Etofenprox 68. Etoprofos 69. Etrimfos 70. Fenamiphos 25 71. Fenazaquina 72. Fenbutatinoxide 73. Fenitrothion 74. Phenoxycarb 75. Phenothiocarb 76. Phenoxcarb 77. Phentratrine 78. Phenirad 79. Piroximate 80. Phthion 10 81. Fenvalerate 82. Fipronil 83. Fluazinam 84. Fluazuron 85. Flucycloxuron 86. Flucitrinate '87. Flufenoxuron 88. Flufenprox 89. Fonofos 90. Formothion 91. Fostiazate 92. Fubfenprox 93. H CH 94. Heptenofos 95. Hexaflum urón 96. Hexltiazox 97. Hydroprene 98. Imidacloprid 99. Insect-active fungi 100. Insect-active nematodes 5 101. Insect-active viruses 102. Iprobenfos 103. Isofenfos 104. Isoprocarb 105. Isoxatión 10 106. Ivermectin 107.? -Cyhalothrin 108. Lufenuron 109. Malathion 110. Mecarbam 15 111. Mesulfenfos 112. Metaldéhído 113. etamidophos 114. Methiocarb 115. Methomyl 20 116. Methoprene 117. Metolcarb 118. Mevinfos 119. Milbemectin 120. Moxidectin. 25 121. Naled 122. NC 184 123. NI-25, Acetamiprid 124. Nitenpyram 125. Ometoate 126. Oxamyl 127. Oxidemetone M 128. Oxideprofos 129. Parathion 130. Parathion-methyl 10 131. Permethrin 132. Fentoate 133. Forate 134. Fosalone 135. Fosmet 15 136. Forte 137. Pirimicarb 138. Pirimiphos A 139. Pirimiphos M 140. Promecarb 20 141. Propaphos 142. Propoxur 143. Protiofos 144. Protoate 145. Piraclofos 25 146. Pyrafalonion 147. Piresmethrin 148. Pyrethrum 149. Pyridaben 150. Pirimidifen 5 151. Pirlproxifen 152. RH 5992 153. RH-2485 154. Salitium 155. Sebufos 156. Silafluofen 157. Espinosad 158. Sulfotep 159. Sulphophos 160. Tebufenozide 15 161. Tebufenpyrad 162. Tebupyrimphos 163. Teflubenzuron 164. Tefluthrin 165. Temephos 20 166. Terbam .167. Terbufos 168. Tetrachlorovphos 169. Tiafenox 170. Thiodicarb 25 171. Tiofanox 172. Thionazine 173. Turinglensin 174. Tralometrin 175. Triartene 176. Triazamate 177. Triazophos 178. Triazuron 179. Trichlorfon 180. Triflumuron 181. Trlmetacarb 182. Vamidothion 183. XMC (3,5-xylyl methylcarbamate) 184. Xylilcarb 185. Yl 5301 / 5302 186.? -Cpermethrin 187. Zetamethrin The non-limiting examples of suitable anthelmintics are mentioned in the following; a few representatives have an anthelmintic activity in addition to the insecticidal and acaricidal activity, and are already partially in the previous list. (A1) Praziquantel = 2-cyclohexylcarbonyl-4-oxo-1, 2,3,6,7,11 b-hexahydro-4H-pyrazino [2,1-] ¡squinoline. (A2) Closantel = 3,5-diiodo-N- [5-chloro-2-methyl-4- (-cyano-4-chlorobenzyl) phenyl] -salicylamide. (A3) Triclabendazole = 5-chloro-6- (2,3-dichlorophenoxy) -2-thiomethyl-1H- benzimidazole (A4) Levamisole = L - (-) - 2,3,5,6-tetrahydro-6-phenylimidazo [2,1-b] thiazole. (A5) Mebendazole = 5-benzoyl-1 H-benzimidazol-2-yl) carbaminic acid methyl ester. (A6) Omfalotin = a macrocyclic fermentation product of the fungus Omphalotus olearius described in International Publication Number WO 97/20857. (A7) Abamectin = avermectin B1. (A8) Ivermectin = 22,23-dlhydroavermectin B1. (A9) Moxidectin = 5-O-demethyl-28-deoxy-25- (1,3-dimethyl-1-butenyl) -6,28-epoxy-23- (methoxy-imino) -milbemicine B. (AIO) ) Doramectin = 25-clclohexyl-5-O-demethyl-25-de (1-methyl-propyl)-avermectin A1a. (A1 DMilbemectin = mixture of milbemycin A3 and milbemicin A4. (A12) Milbemycin oxime = 5-oxime of milbemectin The non-limiting examples of suitable repellents and promoters are: (R1) DEET = (NN-diethyl-m-toluamide). (R2) KBR 3023 = N-butyl-2-oxycarbonyl- (2-hydroxy) -pyridine (R3) Cymyzole = N-2,3-dihydro-3-methyl-1,3-thiazole -2-iliden-2,4-xylidene The components of the mixture are better known to those skilled in the art, most of which are described in the various editions of The Pesticide Manual, The British Crop Protection Council, London, and others. the different editions of The Merck Index, Merck & Co., Inc., Rahway, New Jersey, E.U.A., 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- (thomethyl) proplonaldehyde-O-methylcarbamoyl-oxime (Aldicarb), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 26; (I l) S- (3,4-dihydro-4-oxobenzo [d] - [1,2,3] -triazin-3-ylmethyl) -O, O-dimethyl-phosphorodithioate (Azinphos-methyl), from The Pesticide Manual, 11- Edition (1997), The British Crop Protection Council, London, page 67; (III) Ethyl-N- [2,3-dihydro-2,2-dimethyl-benzofuran-7-yloxycarbonyl-. (methyl) thioamino] -N-isopropyl-β-alaninate (Benfuracarb), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 96; (IV) 2-Methylbiphenyl-3-ylmethyl- (Z) - (1 RS) -cis-3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dlmethyl-c clopropan-carboxylate (Bifenthrin), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 118; (V) 2-tert-butyl-imino-3-isopropyl-5-phenyl-1, 3,5-thiadiazin-4-one (Buprofezin), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council , London, page 157; (VI) 2,3-dlhydro-2,2-dlmethyl-benzofuran-7-yl-methyl-carbamate (Carbofuran), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 186; (Vil) 2,3-dihydro-2,2-dimethyl-benzofuran-7-yl- (dibutylthioamino) -methyl carbamate (Carbosulfan), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council , London, page 188; (VIII) S, S '- (2-d-methyl-amino-trimethylene) -bis- (thiocarbamate) (Cartap), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 193; (IX) 1- [3,5-dlchloro-4- (3-chloro-5-trifluoro-methyl-2-pyridyloxy) -pheni] -3- (2,6-d-fluorobenzoyl) -urea (Clorifluzuron), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 213; (X) O, O-diethyl-O-3,5,6-trichloro-2-pyridyl phosphorothioate (Chlorpyrifos), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 235; (XI) (RS) -acyano-4-fluoro-3-phenoxybenzyl- (1RS, 3RS; 1RS, 3RS) -3- (2,2-dichlorovinyl) -2,2-dimethyl-cyclopropanecarboxylane (Ciflutrin ), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 293; (XII) Mixture of (S) -a-cyano-3-phenoxybenzyl- (Z) - (1 R, 3R) -3- (2-chloro-3, 3, 3-trif I or oro-propeni l) -2, 2-di methyl-cyclopropanecarboxylate and (R) -acyano-3-phenoxy-benzyl- (Z) - (1R, 3R) -3- (2-chloro-3, 3, 3 -trif I uoro-pro peni l) -2, 2-d methyl-cyclopro-pan-carboxylate (Lambda-Cihalotrine), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 300; (XI II) Racemate consisting of (S) -a-cyano-3-phenoxy-benzyl- (Z) - (1 R, 3R) -3- (2,2-dichloro-vinyl) -2.2 -dimetylcyclopropane carboxylate and (R) -acyano-3-phenoxybenzyl- (1S, 3S) -3- (2,2-dichloro-vinyl) -2,2-dimethyl-cyclopropane- carboxylate (Alpha-cypermethrin), from The Pesticide Manual, 1st Edition (1997), The British Crop Protection Council, London, page 308; (XIV) a mixture of the stereoisomers of (S) -a-cyano-3-phenoxy-benzyl- (1 RS, 3RS, 1 RS, 3RS) -3- (2,2-dichloro-vinyl) -2.2 - dimethyl-cyclopropane carboxylate (zeta-cypermethrin), from The Pesticide Manual, 1st Edition (1997), The Brltish Crop Protection Council, London, page 314; (XV) (S) -acyano-3-phenoxy-benzyl- (1R, 3R) -3- (2,2-d.bromo-vinyl) -2,2-dimethyl-cyclopropane-carboxylate (Deltamethrin) , from The Pesticide Manual, 1st Edition (1997), The British Crop Protection Council, London, page 344; (XVI) (4-Chloro-phenyl) -3- (2,6-difluoro-benzoyl) -urea (Diflubenzuron), from The Pesticide Manual, 1st Edition (1997), The British Crop Protection Council, London, page 395; (XVII) (1, 4, 5,6,7, 7-hexachloro-8, 9, 10-trinorborn-5-en-2,3-ilen-bismethylene) -sulfitol (Endosulfan), from The Pesticide Manual, 11a Edition (1997), The British Crop Protection Council, London, page 459; (XVI I I) a-thioethyl-o-tolyl-methyl-carbamate (Etiofencarb), from The Pesticide Manual, 11th Edition (1997), The British Crop Protectio? Council, London, page 479; (XIX) 0, O-dimethyl-0-4-nitro-m-tolyl-phosphorothioate (Fenitrothion), from The. Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 514; (XX) 2-sec-butyl-phenyl-methyl-carbamate (Fenobucarb), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 516; (XXI) (RS) -a-cyano-3-phenoxy-benzyl- (RS) -2- (4-chloro-phenyl) -3-methyl-butyrate (Fenvalerate), from The Pesticide Manual, 11th Edition (1997) , The British Crop Protection Council, London, page 539; (XXII) S- [formyl- (methyl) -carbamoyl-methyl] -O, O-dimethyl-phosphorodithioate (Formothion), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 625; (XXIII) 4-thiomethyl-3,5-xyl-methyl-carbamate (methiocarb), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 813; (XXIV) 7-chloro-bicyclo- [3.2.0] -hepta-2,6-dien-6-yl-dimetri I-phosphate (Heptenophos), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 670; (XXV) 1- (6-chloro-3-pyridyl-methyl) -N-nitro-midazolidin-2-ylidenamine (Imidacloprid), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 706; (XXVI) 2-isopropyl-phenyl-methyl-carbamate (Isoprocarb), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 729; (XXVII) O, S-dimethyl-phosphoramidothioate (Methamidophos), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 808; (XXVIII) S-methyl-N- (methyl-carbamoyloxy) -thioacetimidate (Methomyl), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 815; (XXIX) Methyl-3- (dimethoxy-phosphinoyloxy) -but-2-enoate (Mevinfos), del The Pesticide Manual, 11th Edition (1997); The British Crop Protection Council, London, page 844; (XXX) O, O-diethyl-O-4-nitrophenyl-phosphorothioate (Parathion), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 926; (XXXI) O, O-d¡meti! -O-4-nitrofen i l-f osf orothioate (Parathion-methyl), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 928; (XXXII) S-6-chloro-2,3-dihydro-2-oxo-1,3-benzoxazol-3-ylmethyl-O, O-diethylphosphorodithioate (Fosalone), from The Pesticide Manual, 11a Edition (1997), The British Crop Protection Council, London, page 963; (XXXIII) 2-Dimethyl-amino-5,6-dimethyl-pyrimidin-4-yl-dimethyl-carbamate (Pirimicarb), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 985; (XXXIV) 2-isopropoxy-phenyl-methyl-carbamate (Propoxur), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1036; (XXXV) 1- (3,5-Dichloro-2,4-difluoro-phenyl) -3- (2,6-difluoro-benzoyl) -urea (Teflubenzuron), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1158; (XXXVI) S-tertbutyl-thiomethyl-O, O-dimethyl-phosphorodithioate (Terbufos), from The Pestlcide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1165; (XXXVII) Ethyl- (3-tert-butyl-1-dimethyl-carbamoyl-1H-1,2,4-triazoI-5-ylthio) -acetate (Triazamate), from The Pesticide Manual, 11th Edition (1997) , The British Crop Protection Council, London, page 1224; (XXXVIII) Abamectin, from The Pesticide Manual, 11th Edition (1997), The Brltish Crop Protection Council, London, page 3; (XXXXIX) 2-sec-butyl-phenyl-methyl-carbamate (Phenobucarb), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 516; (XL) N-tert-butyl-N '- (4-ethyl-benzoyl) -3,5-d-methyl-benzo-hydrazide (Tebufenozide), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1147; (XLI) (i) -5-amino-1- (2,6-dichloro-, a, α-trifluoro-p-tolyl) -4- trifluoromethyl-sulfinylpyrazole-3-carbonitrile (Fipronil), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 545; (XLII) (RS) -acyano-4-fluoro-3-phenoxy-benzyl- (1 RS.3RS; 1RS, 3RS) -3- (2,2-dichloro-vinyl) -2, 2-di meti l-cyclopropane carboxylate (beta-Cyfluthrin), from The Pesticide Manual, 11a Edition (1997), The British Crop Protection Council, London, page 295; (XLIII) (4-ethoxy-phenyl) - [3- (4-fluoro-3-phenoxy-phenyl) -propyl] - (dimethyl) -silane (Silafluofen), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1105; (XLIV) (E) - - (1,3-dimethyl-5-phenoxy-pyrazol-4-ylmethylene-amino-oxy) -p-toluate-tert-butyl ester (Fenpyroximate), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 530; (XLV) 2-tert-butyl-5- (4-tert-butyl-thiobenzyl) -4-chloro-pyridazin-3 (2H) -one (Pyridaben), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1161; (XLVI) 4 - [[4- (1,1-dimethyl-phenyl) -phenyl] -ethoxy] -quinazoline (Fenazaquine), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 507; (XLVII) 4-phenoxy-phenyl- (RS) -2- (pyridyloxy) -propi I-ether (Pyriproxyfen), from The Pesticide Manual, 11th Edition (19.97), The British Crop Protection Council, London, page 1073; (XLVIII) 5-chloro-N-. { 2- [4- (2-ethoxyethyl) -2,3-d-methylphenoxy] -ethyl} -6- ethylpyrimidin-4-amine (pyrimidifen), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1070; (XLIX) (E) -N- (6-chloro-3-pyridylmethyl) -N-ethyl-N'-methyl-2-nitro-vinylidene diamine (Nitenpyram), from The Pesticide Manual, 11a Edition (1997), The British Crop Protection Council, London, page 880; (L) (E) -N1 - [(6-chloro-3-pyridyl) -methyl] -N2-Cyano-N1-methyl-acetamidine (NI-25, Acetamiprida), from The Pesticide Manual, 11- Edition (1997) ), The British Crop Protection Council, London, page 9; (Ll) Avermectin B1t from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 3; (Lll) an extract of an active plant against insects, especially (2R, 6aS, 12aS) -1, 2,6,6a, 12,12a-hexahydro-2-iso-propenyl-8,9-dimethoxy-chromene [ 3,4-b] furo [2,3-h] chromen-6-one (Rotenone), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1097; and an extract of Azadirachta indica, especially azadirachtin, from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 59; and (Lili) a preparation containing insect nematodes, preferably Heterorhabditis bacteriophora and Heterorhabditis megidis, from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 671; Steinernema feltiae, from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1115, and Steinernema scapterisci, from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1116; (LIV) a preparation obtainable from Bacillus subtilis, from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 72; or from a strain of Bacillus thuringiensis with the exception of compounds isolated from GC91 or from NCTC11821; The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 73; (LV) a preparation containing fungi active against insects, preferably Verticillium lecanii, from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1266; Beauveria brogniartii, from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 85; and Beauveria bassiana, from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 83; (LVI) a preparation containing insect-active viruses, preferably Neodipridon Sertifer NPV, from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 1342; Mamestra brassicae NPV, from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 759, and Cydia pomonella granulosis virus, from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 291; (CLXXXI) 7-chloro-2,3,4a, 5-tetrahydro-2- [methoxy-carbonyl- (4-trifluoromethoxy-phenyl) -carbamoyl] -indol [1,2e] oxazolin-4a-carboxylate (DPX -MP062, Indoxicarb), from The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 453; (CLXXXII) N'-tert-butyl-N '- (3,5-dimethyl-benzoyl) -3-methoxy-2-methyl-benzo-hydrazide (RH-2485, Methoxyfenozide) ,. of The Pesticide Manual, 11th Edition (1997), The British Crop Protection Council, London, page 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. Editor: American Chemical Society, Washington, D.C. CONEN: 63BFAF. As a consequence of the above details, a further essential aspect of the present invention relates to combination preparations 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, with an equal or different sphere of activity, and at least one physiologically acceptable vehicle. The present invention is not restricted to double combinations. As a rule, the insecticidal and acaricidal compositions according to the invention contain from 0.1 to 99 percent by weight, especially from 0.1 to 95 percent by weight of the active ingredient of the formula I, the, 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 weight percent, especially from 0.1 to 25 weight percent of a surfactant. 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 (floods), powders, tablets, boluses, capsules, necklaces, ear tags, and poured formulations. It is understood that preferred topical formulations refer to a ready-to-use solution in the form of a greased, spilled, or sprayed formulation, which often consists of a dispersion or suspoemulsion or. a combination of the active ingredient and auxiliary extenders. It is understood that the term "greased or poured method" refers to a ready-to-use concentrate intended to be applied topically or locally on the animal. It is intended that this kind of formulation is applied directly to a relatively small area of the animal, preferably on the back or back of the animal. animal, or in one or several points along the line of the back and the back. It is applied as a low volume of about 0.05 to 1 milliliter per kilogram, preferably about 0.1 milliliter per kilogram, with a total volume of 1 to 100 milliliters per animal, preferably limited to a maximum of about 50 milliliters. However, it remains without saying that the total volume has to be adapted to the animal that needs the treatment, and it will clearly be different, for example in young cats and in cattle. These poured and smeared formulations are designed to spread all around the animal, giving protection or treatment to almost any part of the animal. Even so, the administration is carried out by applying a cotton swab or spray of the formulation poured or greased to a relatively small area of the hair, and it is observed that the active substance is dispersed almost automatically over wide areas of the skin, due to the extensor nature of the components of the formulation, and assisted by the movements of the animal. Poured or properly coated formulations 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-octyl-dodecanol or oleyl alcohol; solutions in esters of monocarboxylic acids, such as isopropyl myristate, isopropyl palmitate, lauric acid oxalate, oleyl oleic acid ester, oleic acid decyl ester, hexyl laurate, oleyl oleate, decyl oleate, capric acid esters of saturated fatty alcohols with a chain length of 12 to 18 carbon atoms; solutions of dicarboxylic acid esters, such as dibutyl phthalate, diisopropyl isophthalate, di-isopropyl ester of the acid. adipic, normal dibutyl adipate, or also 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 art. 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. In general, a poured or smeared formulation contains from 1 to 20 weight percent of a compound of 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 greased method is especially suitable for use in gregarious animals, such as cattle, horses, sheep, or pigs, where it is difficult or time consuming to treat all animals orally or by injection. Because of its simplicity, This method, of course, can also be used for all other animals, including individual pets or pets, and is greatly favored by animal caretakers, because it can often be carried out without the specialist presence of the animal. vet. Although it is preferred to formulate commercial products as concentrates, the end user will often use diluted formulations. However, this depends on the mode of administration. Orally administered products are most often used in a diluted form or as food additives, while commercial poured and smeared formulations are "normally concentrated ready to use." These compositions may also contain additional additives, such as stabilizers., anti-foaming agents, viscosity regulators, binding agents, or viscosifiers, as well as other active ingredients, in order to achieve special effects. Insecticidal and acaricidal 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 ingredients of the formula I can be used in all their steric configurations or in mixtures thereof.

The invention also includes a method for the prophylactic protection of animals, especially of producing cattle, domestic animals and pets, against parasitic helminths, which is characterized in that the active ingredients of the formula I, or the formulations of active ingredients prepared to From them, they are administered to animals as an additive to food or beverages, or else in a solid or liquid form, orally, 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 serve merely to illustrate the invention, without restricting it, with the term "active ingredient" representing a substance listed in Table 1. In particular, preferred formulations are formed as follows: (% = percent by weight) Examples of Formulation 1. 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 subsequently the solvent is concentrated by vacuum evaporation. The granulates of this class are They can mix with the animal's food. 2. Granulate Active ingredient 3% Polyethylene glycol (MW: 200) 3% Kaolin 94% (MW: molecular weight) The finely ground active ingredient is uniformly applied in a mixer to the kaolin, which has been moistened with polyethylene glycol. In this way, coated granules free of dust are obtained. 3. Tablets or boluses I. Active ingredient 33.00% Methylcellulose 0.80% Highly dispersed silicic acid 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 has swollen, the silicic acid is stirred, 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 12 M sieve, and dried.

II. The four excipients are completely mixed. III. The preliminary mixtures obtained according to I and II are mixed and compressed to give tablets or boluses. 4. Injectables A. Oily vehicle (slow release) Active ingredient 0.1-1.0 grams Peanut oil up to 100 milliliters 2. Active ingredient 0.1-1.0 grams Sesame oil up to 100 milliliters Preparation: The active ingredient dissolves in a part of the oil with agitation, and if required, with gentle 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 microns. B. Water miscible solvent (average release rate) Active ingredient 0.1-1.0 grams 4- hydroxy methi 1-1, 3-dioxolane 40 grams (glycerol-formal) 1,2-propanediol up to 100 milliliters Active ingredient 0.1-1.0 grams Glycerol-dimethyl ketal 40 grams 1,2-propanediol up to 100 milliliters 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 size of 0.22 micron pores. C. Aqueous Solubilized (Quick Release) 1. Active ingredient 0.1-1.0 grams Polyethoxylated castor oil 10 grams (40 units of ethylene oxide) 1,2-propanediol 20 grams Benzyl alcohol 1 gram Water for injection up to 100 milliliters 2. Ingredient Active 0.1-1.0 grams Sorbitan polyethoxy mono-8 grams side (20 units of ethylene oxide) 4-hydroxymethyl-1,3-dioxolane 20 grams (glycerol-formal) Benzyl alcohol 1 gram Water for injection up to 100 milliliters 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 microns.

. Pouring A. Active ingredient 5 grams Soapyl myristate 10 grams Isopropanol up to 100 milliliters B. Active Ingredient 2 grams Hexyl Laurate 5 grams Triglyceride 15 grams of medium chain. Ethanol up to 100 milliliters.

C. Active ingredient 2 grams Oleyl oleate 5 grams N-methyl pyrrolidone 40 grams Isopropanol up to 100 milliliters. 6. Spread Active ingredient 10-15 grams Diethylene glycol monoethyl ether up to 100 milliliters B. Active ingredient 10-15 grams Octyl Palmitate 10 grams Isopropanol up to 100 milliliters C. Active ingredient 10-15 grams Isopropanol 20 grams Benzyl alcohol up to 100 milliliters 7. Spray A. Active ingredient 1 gram Isopropanol 40 grams Propylene carbonate up to 100 milliliters B. Active ingredient 1 gram Propylene glycol 10 grams Isopropanol up to 100 milliliters The aqueous systems can also be used preferably for oral and / or intraruminal application. The compositions may also contain additional additives, such as stabilizers, for example, where appropriate, epoxidized vegetable oils (coconut oil, rape seed oil, or epoxidized soybean oil); antifoams, for example silicone oil, preservatives, viscosity regulators, binders, viscosifiers, as well as fertilizers or other active ingredients to achieve special effects. Biologically active substances or additional additives which are neutral to the compounds of the formula I can also be added, and they do not have a harmful effect on the host animal to be treated, as well as mineral salts or vitamins, to the compositions described. The following examples serve to illustrate the invention. Do not limit the invention. The letter 'h' denotes hours. The starting substances used can be produced by the methods described in the literature, or they are commercially available. Examples of Preparation Example 1: 4.6-bis- (4-fluoro-3-methyl-phenoxy) -pyrimidin-5-ylamine. In 1 milliliter of N, N-dimethylformamide, 154 milligrams of 4-fluoro-3-methy1-phenol are dissolved, and 30 milligrams of sodium hydride are added slowly. The reaction mixture is stirred for 1 hour at room temperature, and then 0.5 milliliters of a N, N-dimethylformamide solution containing 66 milligrams of 4,6-dichloro-5-amino-pyrimidine in a portion. The. The resulting reaction mixture is stirred and heated for 2 hours at 100 ° C, and for an additional 8 hours at 80 ° C. The reaction mixture is allowed to cool to room temperature. The precipitate is filtered using polyethylene filter cartridges, and washed with 2 milliliters of acetonitrile. The crude mixture is finally purified using reverse phase chromatography of preparation on a Daisogel C 18-ODS AP column with a gradient of water / formic acid (1 0, 000: 1) to acetoniiril / formic acid (1, 000: 1 ). The title compound is isolated by removing the solvent. Example 2: 4.6-bis- (3-fluoro-phenoxy) -pyrimidin-5-ylamine. A mixture of 171 milligrams of 3-fluoro-phenol and 1.38 grams of potassium carbonate is stirred together, and then 1 milliliter of a solution of N, N-dimethylformamide is added. containing 84 milligrams of 4,6-dichloro-5-amino-pyridine, followed by 1 additional milliliter of N, N-dimethylformamide. The resulting reaction mixture is stirred for 18 hours at 80 ° C. Then the reaction mixture is allowed to cool to room temperature. The precipitate is filtered using polyethylene filter cartridges, and washed with 2 milliliters of acetonitrile. The crude residue is purified by preparative reverse phase chromatography on a Daisogel C18-ODS AP column with a water / formic acid gradient (10,000: 1) to acetonitrile / formic acid (10,000: 1). The title compound is isolated by removal of the solvent. Example 3: 4,6-bis- (4-fluoro-3- (trifluoromethyl) -phenoxy) -pyrimidin-5-ylamine. Dissolved in 70 milliliters of N, N-dimethylformamide, are shaken 40. 8 grams of 4-fluoro-3- (trifluoromethyl) -phenol under an inert gas atmosphere, and cooled to 10 ° C. To this, 5.8 grams of sodium hydride are slowly added under vigorous stirring. The mixture is then allowed to cool to room temperature, and is stirred for 1 hour. Then a solution of 19.9 grams of 4,6-dichloro-5-amino-pyrimidine in 50 milliliters of N, N-dimethylformamide, and the reaction mixture is heated for 24 hours to 80 ° C. After quenching with water, and concentration under reduced pressure, the crude mixture is extracted twice with ethyl acetate. The combined organic phases are washed with water and saturated sodium chloride, and finally dried over magnesium sulfate and carbon. The oily dark brown residue dissolves in 100 milliliters of diethyl ether, and treated with 1000 μl hexane. The title compound is crystallized as a colorless solid with a melting point of 104 ° C to 1 05 ° C. Example 4: r4.6-bis- (4-fluoro-3- (trifluoro-methy1) -phenoxy) -1-pyrimidin-5-yl-acetamide. In 2 milliliters of dichloromethane and 57 milligrams of ethyl-diisopropylamine, 100 milligrams of 4,6-bis- (4-fluoro-3- (trifluoromethyl) -phenoxy)] - 5-amino-pyrimidine are dissolved. , and treated with 3.2 milligrams of dimethylaminopyridine and 41 milligrams of acetic acid anhydride. The reaction mixture is stirred at room temperature for 72 hours, the solvent is evaporated, the residue is recovered in. ethyl acetate, and extracted with 2 milliliters of 1N hydrochloric acid, saturated sodium bicarbonate and brine, and finally dried over magnesium sulfate. The organic layer is evaporated, and the resulting solid is purified by column chromatography (eluents: dichloromethane, ethyl acetate). Removal of the solvent provides the title compound. Example 5: Ethyl ester of 4,6-rbis- (4-fluoro-3- (trifluoro-methyl) -phenoxy) -1-pyrim idin-5-ylcarbamoic acid. In 2 milliliters of pyridine, 1 00 milligrams of 4,6-bis- (4-fluoro-3- (trifluoromethyl) -phenoxy) -5-amino-pyrimidine are dissolved and treated with 44 milligrams of chloroformate. ethyl. The reaction mixture is stirred at room temperature for 1 8 hours. Then 2 milliliters of 2N hydrochloric acid are added, and the mixture is extracted three times with diethyl ether. The combined organic layers are washed with Sodium bicarbonate saturated and salted, and finally dried on its magnesium sulfate. After the solvent has been removed, the crude residue is purified by high pressure liquid chromatography in the normal preparation phase, providing the title compound. Example 6: 4.6-rb¡s- (3- (trifluoromethyl) -phenyl-amino) -pyrimidi n-5-ylamine. In 10 milliliters of tetrahydrofuran / water (1: 1), 1.0 grams of 3- (trifluoromethyl) -aniline and 0.5 grams of 5-nitro-4,6-dichloropyrimidine are added, followed by 2 drops of water. Concentrated hydrochloric acid. The reaction mixture is stirred under reflux for 18 hours, cooled to room temperature, and then 2.5 grams of tin dichloride are added. The mixture is stirred under reflux for 1 8 hours, evaporated under reduced pressure, and ethyl acetate is added. The organic phase is washed with saturated sodium bicarbonate and brine, and finally dried over magnesium sulfate. After removing the solvent, the residue is purified by reverse phase chromatography of preparation on a Daisogel C 1 8-ODS AP column with a gradient of water / formic acid (1: 1,000: 1) to aceionitrile / formic acid. The title compound is isolated by removal of the solvent as a solid. The substances mentioned in the following table can also be prepared in a manner analogous to the method described above.

Table 1 Table 2 15 20 25 15 20 25 15 20 Table 3 Table 4 Examples Biological: 1. In vitro activity against Dermanyssus qallinae (red chickens mite). A clean population of female mites is used to seed a properly formatted 96-well plate containing the test substances to be evaluated for antiparasitic activity. Each compound is tested by serial dilution with the objection to determine its Minimum Effective Dose (M ED). The mites are left in contact with the test compound for 10 minutes, and then incubate at 25 ° C and with 60 percent relative humidity (RH) for 5 days, d uring which, the effect of the test com ponent is m oned. The acarid activity was confirmed if the mites were killed without having laid eggs. Oviposition and the subsequent development of mites are also recorded in order to identify the possible growth regulating activity. 2. In vitro activity against Rhipicephalus sanquineus (dog ticks). A clean population of adult ticks is used to seed a properly formatted 96-well plate containing the test substances to be evaluated for antiparasitic activity. Each compound is tested by serial dilution, in order to determine its Minimum Effective Dose. The ticks are allowed to be contacted with the test compound for 10 minutes, and then incubated at 28 ° C and 80% relative humidity (RH) for 7 days, during which the effect of the compound is monitored. proof. Acaricidal activity is confirmed if and when adult ticks are dead. 3. In vitro activity against Ctenocephalides felis (cat fleas). An adult mixed flea population is placed in a properly formatted 96-well plate, allowing fleas to access and feed on treated blood by means of an artificial feeding system. Each compound is tested by serial dilution, in order to determine its Dosage Minimum Effectiveness The fleas are fed with treated blood for 24 hours, after which the effect of the compound is recorded. The insecticidal activity is determined based on the number of dead fleas recovered from the feeding system. The compounds numbers 1.2, 1.3, 1.7, 1.9, 1.22, 1.36, 2.1, 2.2, 2. 5, 2.11, 2.13, 2.14, and 2.17 show in the HTS, an insecticidal or acaricidal efficacy greater than 80 percent. In particular, compounds numbers 1.7, 1.9, 1.22 showed efficacy against Ctenocephalides felis of more than 80 percent in 100 parts per million.

Claims (26)

REVIVALATION IS The use of a compound of the formula: wherein: R'i is hydrogen, halogen, cyano, OH, SH, NO2, COOH, COOR2, CON H2, CON R2R3, SO3H, SO2N R2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo-alkoxy of 1 to 6 atoms carbon, alkenyl of 2 to 6 carbon atoms, halo-alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halo-cycloalkyl of 3 to 6 carbon atoms carbon, cycloalkyloxy from 3 to 6 carbon atoms, cyclothioalkyl from 3 to 6 carbon atoms, alkenyloxy from 2 to 6 carbon atoms, haloalkenyloxy from 2 to 6 carbon atoms, thioalkyl from 1 to 6 carbon atoms, halo -thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyloxy, haloalkyl of 1 to 6 carbon atoms-sulfonyloxy, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms - sulfinyl, alkyl of 1 to 6 carbon atoms - sulfonyl, haloalkyl of 1 to 6 carbon atoms - sulfonyl, thioalkenyl from 2 to 6 carbon atoms, halo-thioalkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms-sulfinyl, halo-alkenyl of 2 to 6 carbon atoms-their lfinyl, alkenyl of 2 to 6 atoms carbon-sulfonyl, halo-alkenyl of 2 to 6 carbon-sulfonyl atoms, N R2R3, unsubstituted or substituted aryl of one to five times, or unsubstituted or substituted hetaryl, the substituents being selected from the group consisting of halogen, cyano, OH, SH, NO2, COOH, COOR2, CON H2, CON R2R3, SO3H, SO2NR2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms , haloalkoxy of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkinyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms , halo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, alkyl eniloxyl of 2 to 6 carbon atoms, halo-alkenyloxy of 2 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyloxy , haloalkyl of 1 to 6 carbon atoms-sulfonyloxy, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl , haloalkyl of 1 to 6 carbon atoms-sulfonyl, thioalkenyl of 2 to 6 carbon atoms, halo-thioalkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms-sulfinyl, halo-alkenyl of 2 to 6 carbon atoms-sulfinyl, alkenyl of 2 to 6 carbon atoms- sulfonyl, haloalkenyl of 2 to 6 carbon atoms-sulfonyl, and NR2R3; R 2 and R 3, independently of one another, mean hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, formyl, alkyl of 1 to 6 carbon atoms, carbonyl, haloalkyl of 1 to 6 carbon atoms-carbonyl, alkoxy of 1 to 6 carbon atoms-carbonyl, halo-alkoxy of 1 to 6 carbon atoms-carbonyl, alkoxy of 1 to 6 carbon atoms-amino-carbonyl, di-alkyl 1 to 6 carbon atoms-amino-carbonyl, or unsubstituted or substituted benzyl from one to five times, the substituents being selected from the group consisting of halogen, cyano, OH, SH, N02, COOH, COOR2, CON H2, CON R2R3, SO3H, SO2NR2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, halo-alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, allo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, halo-alkenyloxy of 2 to 6 carbon atoms, thioalkyl from 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyloxy, haloalkyl of 1 to 6 carbon atoms-sulfonyloxy, alkyl of 1 to 6 atoms of carbon-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 atoms carbon-sulfonyl, haloalkyl of 1 to 6 carbon-sulfonyl atoms, thioalkenyl of 2 to 6 carbon atoms, halo-thioalkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms-sulfinyl, halo-alkenyl of 2 to 6 carbon atoms-sulfinyl, alkenyl of 2 to 6 carbon atoms-sulfonyl, halo-alkenyl of 2 to 6 carbon atoms-sulfonyl; R4, R5, Re, R7, Rs, R9, R10, R11, R? 2 and R-i 3 > independently of one another, they are hydrogen, halogen, cyano, nitro, OH, SH, NO2, COOH, COOR2, CONH2, CONR2R3, SO3H, SO2NR2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms. carbon, alkoxy of 1 to 6 carbon atoms, halo-alkoxy of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, halo-alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms , cycloalkyl of 3 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, haloalkenyloxy of 2 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyloxy, haloalkyl of 1 to 6 carbon atoms-sulfonyloxy, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, thioalkenyl of 2 to 6 carbon atoms, halo-thioalkenyl from 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms-sulfinyl, halo-alkenyl of 2 to 6 carbon atoms-sulfinyl, alkenyl of 2 to 6 carbon atoms-sulfonyl, halo-alkenyl of 2 to 6 carbon-sulfonyl atoms, alkyl of 1 to 6 carbon-amino atoms, di-alkyl of 1 to 6 carbon atoms-amino, alkyou of 1 to 6 carbon atoms-sulfonyl-amino, halo- alkyl of 1 to 6 carbon atoms-sulfonyl-amino, alkyl of 1 to 6 carbon atoms-carbonyl, halo-alkyl of 1 to 6 carbon atoms-carbonyl, alkoxy of 1 to 6 carbon atoms-carbonyl, alkyl of 1 to 6 carbon-amino-carbonyl atoms, d i -alkyl of 1 to 6 carbon atoms-amino-carbonyl, unsubstituted or substituted aryl from one to five times, or unsubstituted or substituted hetaryl, being selected the substituents from the group consisting of halogen, cyano, OH, SH, N2O, COOH, COOR2, CON H2, CON R2R3, SO3H, SO2NR2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo-alkoxy of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, halo-alkenyl of 2 to 6 carbon atoms, alkyne ilo of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, halo-alkenyloxy of 2 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyloxy, halo- alkyl of 1 to 6 carbon atoms-sulfonyloxy, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, halo-alkyl from 1 to 6 carbon atoms-sulfonyl, thioalkenyl of 2 to 6 carbon atoms, halo-thioalkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms-sulfinyl, haloalkyl of 2 to 6 carbon atoms-sulfinyl, alkenyl ienyl of 2 to 6 carbon-sulfonyl atoms, haloalkenyl of 2 to 6 carbon atoms-sulfonyl, and N R2R3; Xi and X2, independently of each other, are C (R14) (R1 5), N R14, O, S, SO or SO2; and R? and R15, independently of one another, mean hydrogen, alkyl of 1 to 6 carbon atoms, formyl, alkyl of 1 to 6 carbon atoms-carbonyl, or haloalkyl of 1 to 6 carbon atoms-carbonyl; in the control of ectoparasites in animals. 2. The use of a compound of the formula according to claim 1, wherein: Ri is hydrogen, halogen, NO2, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, or halo-thioalkyl of 1 to 6 carbon atoms. 3. The use of a compound of the formula according to claim 1, wherein: Ri is hydrogen, halogen, NO2, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 a 6 carbon atoms, or haloalkoxyl of 1 to 6 carbon atoms. 4. The use of a compound of the formula according to claim 1, wherein: Ri is hydrogen, alkyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms. 5. The use of a compound of the formula according to claim 1, wherein: R2 and R3, independently of one another, mean hydrogen, alkyl of 1 to 6 carbon atoms, formyl, alkyl of 1 to 6 carbon atoms carbon-carbonyl, alkoxy of 1 to 6 carbon atoms-carbonyl, alkyl of 1 to 6 carbon atoms-amino-carbonyl, dialkyl of 1 to 6 carbon atoms-amino-carbonyl, or unsubstituted or substituted benzyl of one to five times; the substituents being selected from the group consisting of halogen, cyano, OH, SH, NO2, COOH, COOR2, CON H2, CON R2R3, SO3H, SO2N R2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms carbon, cycloalkyl of 3 to 6 carbon atoms, halo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, halo -alkenyloxy of 2 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms- sulfonyloxy, haloalkyl of 1 to 6 carbon-sulfonyloxy atoms, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, thioalkenyl of 2 to 6 carbon atoms, halo-thioalkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms-sulfinyl, halo-alkenyl of 2 to 6 carbon atoms-sulfinyl, alkenyl of 2 to 6 carbon atoms-sulfonyl, halo-alkenyl of 2 to 6 carbon atoms-sulfonyl. 6. The use of a compound of the formula according to claim 1, wherein: R2 and R3, independently of one another, mean hydrogen, alkyl of 1 to 4 carbon atoms, formyl, alkyl of 1 to 4 carbon atoms, carbon-carbonyl, or benzyl. 7. The use of a compound of the formula according to claim 1, wherein: R2 and R3, independently of one another, mean hydrogen, alkyl of 1 to 2 carbon atoms, benzyl, or formyl. 8. The use of a compound of the formula according to claim 1, wherein: R4, R5, Re, R7, R3, R9, R10, Rn > R 2 and R 13, independently of one another, are hydrogen, halogen, cyano, nitro, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo -alcoxyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms carbon, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, or aryl unsubstituted or substituted one to five times, or unsubstituted or substituted hetaryl; the substituents being selected from the group consisting of halogen, cyano, OH, SH, N2O, COOH, COOR2, CONH2, CONR2R3, SO3H, SO2NR2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 atoms carbon, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, haloalkyl uen 2-C6-C2-C2-C2-C2-C2-C2-C3-C3-C2-C3-C3-C3-C2-C3-C3-C2-C3-C3-C3-C3-C2-C3-C2-C3-C3-C3-C2-C3-C3-C3-C2-C3-C3-C3-C3-C3-C3-C3-C3-C3-C3-C3- -sulfonyloxyalkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, thioalkenyl from 2 to 6 carbon atoms, halo-thioalkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms-sulfinyl, halo-alkenyl of 2 to 6 carbon atoms-sulfinyl, alkenyl of 2 to 6 atoms of carbon-sulfonyl, halo-alkenyl of 2 to 6 carbon atoms-sulfonyl, and N R2R3. 9. The use of a compound of the formula in accordance with Claim 1, wherein: R, R5, R, R7. Rs. R 91 R 10, R 1, R 2 and R 13, independently of one another, are hydrogen, halogen, nickel, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxyl of 1 to 4 carbon atoms, or halo-alkoxy from 1 to 4 carbon atoms. 10. The use of a compound of the formula according to claim 1, wherein: R4, R5, Re, R7, Re, RT < R 10, R 11, R 2 and R 13, independently of one another, are hydrogen, halogen, nitro, alkyl of 1 to 2 carbon atoms, or haloalkyl of 1 to 2 carbon atoms. 11. The use of a compound of the formula according to claim 1, wherein: R, R5, Re, R7. Rßi Rg > River, R11, R12 and Ri3, independently of each other, are hydrogen, halogen, nitro, or CF3. 12. The use of a compound of the formula according to claim 1, wherein: Xi and X2, independently of one another, are NR14, O, or S. The use of a compound of the formula according to claim 1, wherein: X1 and X2, independently of one another, are NH, O, or S. 14. The use of a compound of the formula agreement with ia
1. Claim 1, wherein: The use of a compound of the formula according to claim 1, wherein: R 4 and R 15, independently of one of the other, mean hydrogen, alkyl of 1 to 4 carbon atoms, formyl, alkyl of 1 to 4 carbon atoms-carbonyl. 16. The use of a compound of the formula according to claim 1, wherein: R? and R15, independently of one another, mean hydrogen or alkyl of 1 to 4 carbon atoms. 17. The use of a compound of the formula according to claim 1, wherein: R 4 and R 15 mean hydrogen. 18. The use of a compound of the formula according to claim 1, wherein: Ri is hydrogen, halogen, NO2, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cyclothioalkyl of 3 to 6 carbon atoms, Iioalkyl of 1 to 6 carbon atoms, or halo-thioalkyl of 1 to 6 carbon atoms; R2 and R3, independently of one another, mean hydrogen, alkyl of 1 to 6 carbon atoms, formyl, alkyl of 1 to 6 carbon atoms - carbonyl, alkoxy of 1 to 6 carbon atoms - carbonyl, alkyl of 1 to 6 carbon atoms - amino carbonyl, dialkyl of 1 to 6 carbon atoms or - amino carbonyl, or benzyl; R, R5, R, R, R3. RT, R10, R11 1 R? 2 and Ri 3, independently of one another, are hydrogen, halogen, cyano, nitro, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo- alkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, or unsubstituted or substituted aryl of one to five times, or unsubstituted or substituted hetaryl; the substituents being selected from the group consisting of halogen, cyano, OH, SH, N O2, COOH, COOR2, CON H2, CON R2R3, SO3H, SO2N R2R3, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 atoms carbon, cycloalkyl of 3 to 6 carbon atoms, halo-cycloalkyl of 3 to 6 carbon atoms, cycloalkyloxy of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms , halo-alkanoxygen of 2 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halo-thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyloxy, halo-alkyl of 1 to 6 carbon-sulfonyloxy, alkyl of 1 to 6 carbon atoms-sulfinyl, halo-alkyl of 1 to 6 carbon-sulfinyl atoms, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, thioalkenyl of 2 to 6 carbon atoms, halo-thioalkenyl of 2 to 6 atoms carbon atoms, alkoyl of 2 to 6 carbon atoms-sulfinyl, halo-alkenyl of 2 to 6 carbon atoms-sulfinyl, alkenyl of 2 to 6 carbon-sulfonyl atoms, halo-alkenyl of 2 to 6 carbon-sulfonyl atoms, and N R2R3. Xi and X2, independently of one another, are N R? 4, O, or S; and R 4 represents hydrogen, alkyl of 1 to 4 carbon atoms, formyl, alkyl of 1 to 4 carbon atoms, carbonyl. 19. The use of a compound of the formula according to claim 1, wherein: Ri is hydrogen, halogen, NO2, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or haloalkoxy of 1 to 6 carbon atoms; R2 and Rs, independently of one another, mean hydrogen, alkyl of 1 to 4 carbon atoms, formyl, alkyl of 1 to 4 carbon atoms, carbonyl, or benzyl; R4, R5, R6, R7, R8, R9, R1, Rn, R2 and R13. independently of one another, they are hydrogen, halogen, nitro, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, or halo-alkoxy of 1 to 4 atoms of carbon; and Xi and X2, independently of one another, are N H, O, or S. 20. The use of a compound of the formula according to claim 1, wherein: Ri is hydrogen, alkyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms; R2 and R3, independently of one another, mean hydrogen, alkyl of 1 to 2 carbon atoms, formyl, or benzyl; R 4, R 5, R 3, R, R 5 R 9, R 10, R 11 R 12 and R 13, independently of one another, are hydrogen, halogen, nitro, alkyl of 1 to 2 carbon atoms, or haloalkyl of 1 to 2 carbon atoms; and X1 and X2 are O. The use of a compound of the formula according to claim 1, wherein: R1 is hydrogen, alkyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms; R2 and R3, independently of one another, mean hydrogen, alkyl of 1 to 2 carbon atoms, formyl, or benzyl; R4, R5, R6, R7. Re, R9, R10, R111 R12 and R-I3, independently of one another, are hydrogen, halogen, nitro, or CF3; and X1 and X2 are O. 22. An ectoparasiticidal composition, which comprises a compound of formula I as defined in any of claims 1 to 20, and a physiologically acceptable carrier and / or dispersant. 23. The ectoparasiticide composition according to claim 22, which consists of a poured or greased formulation. 24. A method for controlling ectoparasites, wherein an effective amount of at least one compound of the formula I according to claim 1 is administered to the habitat of the parasites. 25. The use of a compound of the formula I as defined in any of claims 1 to 21, for the preparation of an ectoparasiticide composition according to claim 22. 26. The compound of the formula I as defined in any of claims 1 to 21, for use in the treatment of ectoparasites in non-human animals.