MXPA01000554A - Diphenylimidazolines - Google Patents

Abstract

The invention relates to novel diphenylimidazolines of formula (I), wherein Ar1, Ar2 and R have the meaning mentioned in the description. The invention also relates to several methods of production thereof and to their use in controlling animal pests.

Description

DIFENILIMIDAZOLINAS. FIELD OF THE INVENTION The invention relates to novel diphenylimidazolines, to processes for their preparation and to their use for the control of animal pests. Description of the prior art. Only a small number of 2,4-diaryl-4,5-dihydroimidazoles, which are optionally substituted in the nitrogen and aryl radicals, are known to date. The base compound, 2,4-diphenyl-4,5-dihydro-lH-imidazole, was synthesized as early as the 19th century (Chem. Ber. 28, 3172 (1895)). In addition, N-methoxycarbamate has been described in Tetrahedron 29, 3137 (1973), in SU 466231 (cited in CA 83: 79277) the N-cyclohexyl derivative, in EP-A 10 852 the N-hydroxyethyl derivative and finally in Synlett 10, 1031 (1995), the 2-para-methyl-4-para-methoxy-substiutide derivative in both phenyl rings as well as the corresponding mono-substituted compounds. Finally, two derivative compounds have been described with respect to the formula of the 3H-imidazole tautomer, 5- (3,4-dimethylphenyl) -l-methyl-2-phenyl-4,5-dihydro-1H-imidazole in Pol. Ann. . Univ. Mariae Curie-Sklodowska, Sect. D 36, 111 (1981) and 2-hydroxy-phenyl-1-methyl-5-phenyl-4,5-dihydro-1H-imidazole in Proc. Indian Acad. Sci., Chem. Sci. JO4, 383 (1992). Diphenylimidazolines have been described in other patent publications without specific examples: BE 695 703; BE 839 503; BE 846 373; DD 155296 (cited in C.A. 98: 57781); DOS 25 12 513; DOS 27 38 270; DOS 29 46 085; DOS 32 04 333; DOS 32 1 1 301; DOS 32 36 598; DOS 36 10 758; DOS 40 17 801; DOS 42 35 590; EP-A 1 468; EP-A1 516 982; EP-A2 617 069; FR-A1 2629092; JP-A 56 90982 (cited in C.A. 96: 147323); JP-A 56 90984 (cited in C.A. 96: 147322); JP-A 58 152085 (cited in C.A. 100: 213975); JP-A 59 116660 (cited in C.A. 102: 36786); JP-A2 62 195369 (cited in C.A.108: 167467) JP-A 04 180944 (cited in C.A. 118: 23600); US 3,202,674; US 4,066,625; US 4,661,600; WO Ref: 126781 93/04045; WO 93/04046; substituted derivatives in both phenyl rings have been described in DOS 27 01 372 (only the methyl and ethyl substituents), in DOS 32 17 875 (if the term aryl is understood to mean 6 to 15 carbon atoms, for example tolyl or xylyl) ), in US 4,389,371 as well as in US 4,452,758 (exclusively alkali metal salts of N- (alkoxy) -alkylcarboxylic acids) and in DOS 27 44 782 as well as in EP-A1 596 326 ( especially heterocyclylmethyl substituent). To date, nothing has been disclosed about the use of 2,4-diaryl-4,5-dihydroimidazoles as pesticidal agents. Detailed description of the invention. New diarylimidazolines of the formula (I) have now been found where Ar means grouping (a) wherein R 1 signifies halogen, alkyl, alkoxy or halogenoalkoxy and R 2 signifies hydrogen, halogen, alkyl or alkoxy, Ar 2 means groupings (b) or (c) wherein R3, R4, R5 and R6, independently of each other, mean, respectively, hydrogen, halogen, alkyl, alkoxy, haloalkyl or haloalkylthio, R7 means hydrogen, halogen, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio and Y means a direct bond, oxygen, methylene, -O-CH2- or -CH2O- and R means cyano, alkoxyalkyl, formyl, alkylcarbonyl, alkoxycarbonyl or -C (X) -NHR8, where X means oxygen or sulfur and R8 means hydrogen or alkyl, in this case halogen means F, Cl, Br and iodine, especially means F, Cl and Br.

The compounds of the formula (I) encompass N-substituted derivatives of both tautomeric forms of the cyclic imidate function on which the imidazoline is based. These are lH-4,5-dihydroimidazoles of the formula (I) a and 3H-4,5-dihydroimidazoles of the formula (I) b, which has been expressed by means of the broken line in the formula (I).

The compounds of the formulas (I) a and (I) b can be present both in the form of mixtures and also in the form of the pure isomers and also, depending on the type of the substituents, in the form of geometrical and / or optical isomers or mixtures of isomers of different composition. These isomers can be separated, if appropriate, in a customary manner. The invention relates both to the pure isomers and also to their mixtures. It has also been found that the novel compounds of the formula (I) are obtained according to one of the methods described below. A) Diphenylimidazolines of the formula (I-a) can be obtained wherein Ar1 and Ar2 have the meanings indicated above and R means alkyl having 1 to 4 carbon atoms, if ß-chlorocarbamates of the formula (II) are condensed wherein Ar and R have the meanings indicated above, with benzonitriles of the formula (III), Ar'-CN (III) in which Ar1 has the meanings indicated above, in the presence of sulfuric acid, B) diphenylimidazolines can be obtained of the formula (Ib) wherein R has the meanings stated above and R1"1 means fluorine, chlorine, alkyl, alkoxy or halogenoalkoxy, R2" 1 means hydrogen, fluorine, chlorine, alkyl or alkoxy, R5"1 and R6" 1 independently of each other, mean respectively hydrogen, fluorine, chlorine, alkyl, alkoxy, haloalkyl or haloalkylthio and R 1 means hydrogen, fluorine, chlorine, cyano, alkyl, alkoxy, alkylthio, haloalkyl or haloalkylthio, if halogen compounds of the formula (Ic) are coupled wherein R, R ", R" and R "have the meanings indicated above and Z means bromine or iodine, with boronic acids of the formula (IV) wherein R6"1 and R7" 1 have the meanings indicated above, in the presence of a catalyst, and, if appropriate, in the presence of an acid-binding agent as well as, if appropriate, in the presence of a diluent, C) diphenylimidazolines of the formula (I) can be obtained in which Ar ^ Ai ^ and R have the meanings indicated above, if condensed diphenyl imidazolines, not substituted in the nitrogen, of the formula (V) wherein Ar1 and Ar2 have the meanings indicated above, with compounds of the formula (VI) R'-X1 (VI) in which R has the meanings indicated above, and X1 signifies a suitable dissociable group, in solution of the rest R , such as -Cl, -Br, -OSO2OR10 or -OR10, where R10 means alkyl or aryl, if appropriate in the presence of a reaction auxiliary agent, D) phenylimidazolines of the formula (Id) can be obtained wherein Ar1, Ar2 and X have the meanings indicated above, if nitriles of the formula (I-e) are reacted wherein Ar and Ar have the meanings indicated above, with water or hydrogen sulfide, if appropriate in the presence of an auxiliary agent of the reaction. It has also been found that the compounds of the formula (I) and their salts with biological activity are suitable for the control of animal pests, especially against insects, arachnids and nematodes. The new compounds are defined in general by means of formula (I). The preferred substituents or the ranges of the residues indicated in the formulas indicated above and which be indicated below, are explained below. Preferably, Ar1 means the grouping (a) Preferably, Ar2 means groupings (b) or (c) Preferably, R means cyano, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, alkoxycarbonyl with 1 to 4 carbon atoms or -C (X) -NHR8. Preferably, R 1 means halogen, alkyl having 1 to 3 carbon atoms, alkoxy with 1 to 3 carbon atoms or halogenalkoxy with 1 to 3 carbon atoms. Preferably, R 2 is hydrogen, halogen, alkyl having 1 to 3 carbon atoms or alkoxy with 1 to 3 carbon atoms.

Preferably, R3, R4, R5 and R6 mean, independently of each other, respectively hydrogen, halogen, alkyl having 1 to 12 carbon atoms or alkoxy with 1 to 12 carbon atoms. Preferably, R7 signifies hydrogen, halogen, cyano, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms halogenalkyl with 1 to 6 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms. carbon or halogenalkylthio atoms with 1 to 4 carbon atoms. Preferably, R8 means hydrogen or alkyl having 1 to 4 carbon atoms. Preferably, X means oxygen or sulfur. Preferably, Y means a direct bond or oxygen. Preferably, halogen means, in this case F, Cl, Br and iodo, especially means F, Cl and Br.

Particularly preferably, Ar1 means the grouping (a) Particularly preferably, Ar2 means groupings (b-a) or (c-a) Particularly preferably, R means cyano, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 3 -alkylcarbon, C 1 -C 2 -alkoxycarbonyl or -C (X) -NHR8. Particularly preferably, R 1 represents fluorine, chlorine, bromine, iodine, alkyl having 1 to 3 carbon atoms and alkoxy with 1 to 3 carbon atoms. Particularly preferably, R 2 represents hydrogen, fluorine, chlorine, bromine, alkyl having 1 to 3 carbon atoms or alkoxy with 1 to 3 carbon atoms. Particularly preferably, R3, R4, R5 and R6 mean, independently of one another, hydrogen, fluorine, chlorine, bromine, iodine, alkyl having 1 to 6 carbon atoms or alkoxy with 1 to 6 carbon atoms. Particularly preferably, R7 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, means alkyl having 1 to 4 carbon atoms. to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or alkylthio with 1 to 4 carbon atoms substituby fluorine or chlorine. Particularly preferably R8 is hydrogen or alkyl having 1 to 4 carbon atoms. Particularly preferably, X means oxygen or sulfur. Very particularly preferably, Ar1 means groupings (a-1), (a-2) or (a-3) (a-1) «.a- /). (a-3).

Very particularly preferably, Ar2 means groupings (b-b) or (c-b) Very particularly preferably, R means cyano, ethoxymethyl, acetyl, propionyl, butyryl, methoxycarbonyl, ethoxycarbonyl or -C (X) -NHR8. Very particularly preferably R1 means fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy. Very particularly preferably R represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy. Very particularly preferably, R3, R4, R5 and R6 mean, independently of each other, respectively hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.-butyl, tere -butyl, pentyl, hexyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec. -butoxy, tert-butoxy, pentyloxy or hexyloxy. Very particularly preferably R7 means fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.-butyl, tere-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n - butoxy, isobutoxy, sec. -butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, 1,1-difluoroethoxy, 1,1,2-trifluoroethoxy, 1,1, 2,2-tetrafluoroethoxy, 2-chloro-l, l, 2-trifluoroethoxy, 2,2,2-trichloro-1,1-difluoroethoxy, pentafluoroethoxy, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, 1,1-difluoroethylthio, 1,1, 2-trifluoroethylthio, 2,2,2-trifluoroethylthio, 1, 1, 2,2-tetrafluoroethylthio, 2-chloro-1, 1,2-trifluoroethylthio, 2,2,2-trichloro-1,1-difluoroethylthio or pentafluoroethylthio. Very particularly preferably R represents hydrogen, methyl or ethyl. Very particularly preferably, X means oxygen or sulfur. In a particularly particularly preferred manner, Ar1 means the grouping (a-3) In particular, very particularly preferably, Ar2 means the grouping (b-c) In particular, very particularly preferably, R1 and R2 are the same or different and denote hydrogen, F, Cl, CH3 or ethyl, where R1 and R2 can not simultaneously mean hydrogen. In particular, R 3 signifies particularly substitubromine, phenyl or phenoxy, with substituents in this case being -OCF 3, -SCF 3 or t-butyl. In particular, very particularly preferably, R means methyl, ethyl, propyl, i-propyl, cyano, O O -C-NH, - C-O-C2H5 -C-C-CH2-O-C, 2H "" 5 In a very special way, particularly preferably, Ar1 means the grouping (a-3) In a very special way, particularly preferably, Ar2 means the grouping (b-c) Very particularly preferably, R and R are the same or different and represent F, Cl and hydrogen, where R and R can not simultaneously mean hydrogen. In a very special way, particularly preferably, R3 means bromine or 4-trifluoromethoxyphenyl. In a very special way, particularly preferably, R means O-C-O-C2HS CN, -C -O-CH II S 2 '' 5-C-CH, II - • C-NH, The definitions of the remains or the explanations given above in a general manner or indicated in the preferred ranges can be combined arbitrarily with each other, ie even between the respective ranges and the preferred ranges. These are valid for the final products as well as correspondingly for the starting products and for the intermediate products. According to the invention, the compounds of the formula (I) are preferred, in which a combination of the meanings indicated above is preferably present (preferably). According to the invention, the compounds of the formula (I), in which a combination of the meanings indicated above are especially preferred, are particularly preferred.

According to the invention, the compounds of the formula (I), in which a combination of the abovementioned meanings is very particularly preferably present, are very particularly preferred. According to the invention, the compounds of the formula (I), in which a combination of the abovementioned meanings are particularly particularly preferred, are particularly particularly preferred according to the invention, particularly preferably those of the formula (I). compounds of the formula (I) in which a combination of the meanings indicated above is present in a very special manner, particularly preferably. The saturated or unsaturated hydrocarbon radicals, such as alkyl, can be, respectively, straight-chain or branched chain, insofar as possible, even in combination with heteroatoms, such as, for example, alkoxy. The substituted radicals can be mono- or polysubstituted, the substituents being the same or different in the case of polysubstitutions. If, for example, ethyl N- [2-chloroethyl-2- (3-methylphenyl)] -carbamidate and 2-propylbenzonitrile are used as starting materials, the reaction sequence of process (A) according to the invention can be represented. the invention by means of the following formula scheme: If, for example, 4- (4-bromophenyl) -l-ethoxycarbonyl-2- (2,6-difluorophenyl) -4,5-dihydro-1H-imidazole is employed. and 4-methylphenylboronic acid as starting materials, the development of the reaction of process (B) according to the invention can be represented by means of the following formula scheme: If, for example, 4- (2-chlorophenyl) -2- (2,6-difluorophenyl) -4,5-dihydro-1 H-imidazole and N-methylcarbamoyl chloride are used as starting materials, it may be represented the development of the reaction of process (C) according to the invention by means of the following formula scheme: If it is reacted, for example, 4- (2-chlorophenyl) -l-cyano-2- (2,6-difluorophenyl) ) -4,5-dihydro-1 H-imidazole as starting material with aqueous sulfuric acid, the development of the reaction of the process (D) according to the invention can be represented by means of the following formula scheme: The β-chlorocarbamates, necessary for carrying out the process (A) according to the invention, are generally defined by means of formula (II). In this formula, Ar2 and R9 preferably have those meanings that have already been mentioned as being preferred with the description of the diarylimidazolines of the formula (I) The β-chlorocarbamates of the formula (II) can be obtained, for example, by the addition of ethyl N, N-dichlorocarbamidate of the formula (VII) on styrenes of the formula (VIII) in a dipolar aprotic solvent such as, for example, acetonitrile , at temperatures between -20 and + 20 ° C and halogenation of the N-chlorocarbamide acid ester, formed first, with a reducing agent, such as for example bisulfite solution, according to the following reaction scheme: (VII ) (VIII) (II) The ethyl N, N-dichlorocarbamidates of the formula (VII) are commercially available, known from the literature or can be obtained analogously to known processes (see for example the publications Thomas A. Foglia, Daniel Swern, J. Org. Chem. 31 (1966) 3625-3631; Ronald E. White, Peter Kovacic, J. Am. Chem. Soc. 97 (1975) 1180-1184). The benzonitriles needed in addition to carry out the procedure (A) according to the invention are generally defined by means of formula (III). In this formula Ar1 preferably has that meaning which has already been mentioned as being preferred in relation to the description of the diarylimidazolines of the formula (I).

The benzonitriles of the formula (III) and the styrenes of the formula (VIII) are generally known compounds of organic chemistry (see the manuals of organic chemistry such as for example Beyer-Walter, manual of organic chemistry, 21st edition, 1988 ), and in part they can be obtained commercially. The halogen compounds of the formula (Ic) which are necessary for carrying out the process (B) according to the invention are an integral part of the compounds according to the invention of the general formula (I) and can be prepared, for example, according to processes (A), (C) or (D). The boronic acids also necessary for carrying out the procedure (B) according to the invention are defined in general by means of formula (IV). In this formula R6"'and R7" 1 preferably have those meanings which have already been mentioned as being preferred in relation to the description of the diarylimidazolines of the formula (I), with the exception of bromine and iodine. The aromatic boronic acids of the formula (IV) are commercially available, are known from the literature or can be prepared analogously to known methods [cf. Chem. Rev. 45, 2457 (1995); Puree Appl. Chem. 66, 213 (1994)]. The diarylimidazolines necessary for carrying out the process (C) according to the invention are generally defined by the formula (V). In this formula, Ar1 and Ar2 preferably have those meanings which have already been mentioned as being preferred in relation to the description of the N-substituted diarylimidazolines of the formula (I). The diarylimidazolines of the formula (V) are new and also constitute an object of the present application. The diarylimidazolines of the formula (V) can be prepared, for example, if carbamates of the formula (Ia) are dissociated with alkali metal hydroxides, such as, for example, potassium hydroxide, in the presence of a solvent, such as, for example, ethanol, at temperatures from 20 to 120 ° C, according to the following reaction scheme: (I-a) (V) The carbamates of the formula (I-a) are an integral part of the compounds according to the invention of the general formula (I) and can be prepared, for example, according to process (A). The N-cyanodiphenylimidazolines of the formula (Id), necessary for carrying out the process (D) according to the invention, are an integral part of the compounds according to the invention of the general formula (I) and can be prepared, for example, according to the process (C). ). The process (A) according to the invention is carried out in the presence of sulfuric acid (aqueous). In general, it works at concentrations of 80% up to 100%. The temperature of the reaction in the case of process (A) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 50 ° C, preferably between 0 and 30 ° C. When carrying out the process (A) according to the invention, in general, per mol of β-chlorocarbamate of the formula (II), from 0.5 to 3 mol, preferably from 1 to 2 mol, of benzonitrile of the formula ( III). In this case, the acid will be used in a large excess, for example 2 to 20 times, if necessary, the acid will also be used as solvent. For carrying out the process (B) according to the invention, palladium complex catalysts are suitable. Preferred catalysts are, for example, tetrakis (triphenylphosphine) palladium and dichloro-bis (triphenylphosphine) palladium. Suitable acid acceptors for carrying out process (B) according to the invention are inorganic or organic bases. These preferably include hydroxides, acetates, carbonates or bicarbonates of alkaline earth metals or alkali metals, such as, for example, sodium, potassium, barium or ammonium hydroxide, sodium, potassium, calcium or ammonium acetate. , sodium, potassium or ammonium carbonate, sodium or potassium bicarbonate, alkali fluorides such as for example cesium fluoride, as well as tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N -dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). Suitable diluents for carrying out the process (B) according to the invention are water, organic solvents and mixtures thereof. Examples which may be mentioned are: aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as for example chlorobenzene, dichlorobenzene, methylene chloride, chloroform, tetrachloromethane, dichloro-, trichloroethane or tetrachlorethylene; ethers, such as, for example, diethyl-, diisopropyl-, methyl-t-butyl-, methyl-t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, diethylene glycolimelethyl ether or anisole; alcohols, such as for example methanol, ethanol, n- or iso-propa-nol, n-, iso-, sec- or tere. -butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether; Water. The temperature of the reaction in the case of process (B) according to the invention can vary within wide limits. In general, the process is carried out at temperatures between 0 ° C and + 140 ° C, preferably between 50 ° C and + 100 ° C. In carrying out the process (B) according to the invention, the boronic acids of the formula (IV) and the halogen compound of the formula (Ic) are used in molar proportions of 1: 1 to 3: 1, preferably 1: 1 to 2. :1. In general, from 0.005 to 0.5 mol, preferably from 0.01 mol to 0.1 mol of catalyst are used per mol of the compound of the formula (I-c). The base is generally used in excess. The process (C) according to the invention is carried out in the presence of a suitable reaction auxiliary agent. As such, all usual inorganic or organic bases are suitable. These preferably include hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates of alkaline earth metals or alkali metals, such as, for example, sodium hydride, sodium, potassium or ammonium hydroxide, sodium amide, diisopropylamide. of lithium, sodium methylate, sodium ethylate, potassium tert-butylate, sodium, potassium, calcium or ammonium acetate, sodium, potassium or ammonium carbonate, sodium bicarbonate, or potassium carbonate, as tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethyl-aminopyridine, diazabicyclooctane (DABCO), diazabicyclononene ( DBN) or diazabicycloundecene (DBU). The process (C) according to the invention can be carried out, if appropriate, in the presence of a suitable phase transfer catalyst. Examples of such catalysts include: iodide, bromide or tetrabutylammonium chloride, tributylmethylphosphonium bromide, trimethyl-alkylammonium chloride or bromide with 13/15 carbon atoms, dibenzyldimethylammonium methylisulfate, dimethyl-alkylbenzylammonium chloride with 12/14 carbon atoms. carbon, 15-crown-5, 18-crown-6 or tris- [2- (2-methoxyethoxy) -ethyl] -amine. The process (C) according to the invention is preferably carried out in the presence of a diluent. In this case, water, organic solvents and arbitrary mixtures thereof are considered. Examples which may be mentioned are: aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as for example chlorobenzene, dichlorobenzene, methylene chloride, chloroform, tetrachloromethane, dichloro-, trichloroethane, or tetrachlorethylene; ethers, such as, for example, diethyl-, diisopropyl-, methyl-t-butyl-, methyl-t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, diethylene glycol dimethyl ether or anisole; ketones, such as for example acetone, butanone, methyl isobutyl ketone or cyclohexanone; nitriles, such as for example acetonitrile, propionitrile, n- or isobutyronitrile or benzonitrile; amides, such as for example formamide, N, N-dimethylformamide, N, N-dimethyl-acetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide; N-oxides such as N-methylmorpholine N-oxide; esters such as for example methyl, ethyl or butyl acetate; sulfoxides, such as, for example, dimethyl sulfoxide; sulfones, such as sulfolane; alcohols, such as for example methanol, ethanol, n- or iso-propanol, n-, iso-, sec- or tert.-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether; Water. The temperature of the reaction in the case of process (C) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 100 ° C, preferably between 0 ° C and 60 ° C.

When carrying out the process (C) according to the invention, generally 1 to 5 mol of the compound of the formula (VI) are used per mole of the compound of the formula (V). However, a higher excess of the compound of the formula (VI) can be used when convenient, for example in the case of a gaseous reactant. The process (D) according to the invention is carried out in the presence of a reaction auxiliary agent. In the reaction with sulfuric acid, for example, tertiary amines such as pyridine or triethylamine are used. These can also serve as diluents at the same time. In the case of the reaction with water, for example, aqueous mineral acids such as sulfuric acid or hydrochloric acid are used, preferably 96% sulfuric acid. The acids can also serve as diluents at the same time.

The temperature of the reaction in the case of process (D) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 100 ° C, preferably between 0 ° C and 60 ° C.

The amount of hydrogen sulphide or water, used in carrying out the process (D) according to the invention, is not critical. At least 1 mole of hydrogen sulphide or water will be required per mole of nitrile of the formula (I-e). It is convenient in the case of hydrogen sulfide to use a higher excess. The reactions of the processes according to the invention (A to D) can be carried out at normal pressure or at higher pressure. Preferably work at normal pressure. The conduct of the reaction, the preparation and the isolation of the products of the reaction is carried out according to known methods, generally customary. The final products are preferably purified by crystallization, separation by chromatography or by removal of the volatile components, optionally in vacuo (see also the preparation examples). The active compounds according to the invention are suitable, with a good compatibility for plants and a toxicity suitable for mammals, for the control of animal pests, preferably against insects, arachnids and nematodes, which occur in agriculture, in forestry, for the protection of stored products and materials as well as in the field of hygiene. They are active against normally sensitive and resistant species as well as against all or some of the stages of development. The plagues cited above belong: From the order of the isopods, for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the diplópodos, for example, Blaniulus guttulatus.

From the order of the chilopoda, for example, Geophilus carpophagus, Scutigera spec .. From the order of the syphilis, for example, Scutigerella immaculata. From the order of the tisane, for example, Lepisma saccharina. From the order of springtails, for example, Onychiurus armatus. From the order of the orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Germanic Blattella, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria. From the order of dermápteros, for example, Forfícula auricularia. From the order of the Isoptera, for example, Reticulitermes spp. From the order of the anopplides, for example, Pediculus humanus corporis, Haematopinus spp., Linognathus spp. From the order of the malophagus, for example, Trichodectes spp., Damalinea spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci. From the order of the heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex Lectularius, Rhodnius prolixus, Triatoma spp. From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cruptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium ate , Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens; Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp. Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofinannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanimous, Tortrix viridana. From the order of Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica. From the order of Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera, for example, Aedes spp. Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tas spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Typula paludosa. From the order of the siphonoptera, for example, Xenopsylla cheopis, Ceratophyllus spp. From the order of the arachnids, for example Scorpio maurus, Lactrodectus mactans.

From the order of mites, for example Acarus siró, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp. ., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp. The plant parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp. The active compounds according to the invention of the formula (I) are characterized in particular by an excellent effect against larvae of the leaf beetle. of the horseradish (Phaedon cochleariae), against the caterpillars of the moth nochiela (Spodoptera frugiperda), and against all the stages of the common red spider mite (Tetranychus urticae). The active compounds according to the invention can be converted into customary formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active product, as well as microencapsulated in polymer materials. These formulations are prepared in known manner, for example by mixing the active compounds with extenders, ie with liquid solvents and / or solid excipients, optionally with the use of surfactants, ie emulsifiers and / or dispersants and / or foam generating means. When water is used as an extender, organic solvents can be used, for example, as auxiliary solvents. Preferred liquid solvents are: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol, as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethisulfoxide as well as water. Suitable solid excipients are, for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly dispersed silicic acid, aluminum oxide and silicates, as solid excipients for granulates are considered: for example broken and fractionated natural minerals, such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granules of organic material, such as sawdust, coconut husks, corn ears and tobacco stems; suitable emulsifiers and / or foamers are, for example, nonionic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated ethers of fatty alcohols, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulphates, arylsulfonates, as well as albumin hydrolysates; Suitable dispersants are, for example, sulphite lignin bleach and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers that are pulverulent, granulable or in the form of latex, such as gum arabic, polyvinyl alcohol, acetate, can be used in the formulations. polyvinyl, as well as natural phospholipids such as cephalin and lecithin, and synthetic phospholipids.

Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, Prussian blue and organic dyes, such as metallic alizarin, azo and phthalocyanine dyes as well as trace nutrients, such as iron salts, manganese, may be employed. , boron, copper, cobalt, molybdenum and zinc. The formulations contain, in general, between 0.1 and 95% by weight, preferably between 0.5 and 90% of active product. The active compounds according to the invention can be present in their commercially available formulations as well as in the application forms prepared from these formulations, in admixture with other active ingredients, such as insecticides, baits, sterilants, acaricides, nematicides, fungicides, growth regulating products or herbicides. Insecticides include, for example, esters of phosphoric acid, carbamates, esters of carbonic acid, chlorinated hydrocarbons, phenylureas, products prepared by means of micro-organisms and the like. Particularly convenient components of the mixture are, for example, the following: Fungicides: 2-Aminobutane; 2-anilino-4-methyl-6-cyclopropylpyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) -acetamide; 8-hydroxyquinolinesulfate; methyl- (E) -2-. { 2- [6- (2-Cyanophenoxy) -pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; methyl- (E) -methoxyimino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), Aldimorph, Ampropylfos, Anilazin, Azaconazole, Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate, calcium polysulfide, Captafol, Captan, Carbendazim, Carboxin, Chinomethionat (Quinomethionat), Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Cufraneb, Cymoxanil, Cyproconazole, Cyprofuram, Dichlorophen, Diclobutrazol, Dicloftianid, Diclomezin, Dicloran, Diethofencarb, Difenoconazole, Dimethirimol, Dimethomo h, Diniconazole, Dinocap, Diphenylamin, Dipyrithion, ditalimfos, dithianon, Dodin, drazoxolon, edifenphos, Epoxyconazole, ethirimol, Etridiazole, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, Fenpropimorf, Fentinacetate, Fentinhydroxyd, Ferba, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Flutriafol, Folpet, Fosetyl-Aluminum, Fthalide, Fuberidazole, Furalaxil, Furmecyclox, Guazatine, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imibenconazole, Iminoctadin, iprobenfos (IBP), Iprodion, Isoprothiolan, kasugamycin, copper compositions such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, oxide copper, copper oxine and mixture Bordeux, Mancopper, Mancozeb, Maneb Mepanipyrim, Mepronil, Metalaxyl, Metconazole, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil, Nickel dimethyldithiocarbamate, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin, Perf razoat, Penconazole, Pencycuron, Phosdiphen, Phthalid, Pimaricin, Piperalin, Polycarbamate, Polyoxin, Probenazole, Prochloraz , Procymidon, Propamocarb, Propiconazole, Propineb, Pyrazophos, Pyrefenox, Pyrimethanil, Pyroquilon, Quintozen (PCNB), Sulfur and sulfur compositions, Tebuconazole, Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazoxid, Trichlamid, Tricyclazole, Tridemofh, Triflumizol, Triforin, Triticonazole, Validamycin A, Vinclozolin, Zineb, Ziram. Bactericides: bronopol, dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, Octhilinon, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations. Insecticides / Acaricides / Nematicides: Abamectin, Acephat, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculovirus, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyluthrin, Bifenazate, Bifenthrin, Bioethanomethrin, Biopermethrin, BPMC, Bromophos A, Bufencarb, Buprofezin, Butathiophos, Butocarboxin, Butylpiridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap , Chloethocarb, Chlorethoxyphos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Chlovaporthrin, Cis-Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Cyanophos, Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazine, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diacloden, Diafenthiuron, Diazinon, Dichlorvos, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn, Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiophencarb, Ethion, Ethoprophos, Ethofenprox, Etoxazole, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufenoxuron, Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb, Granulosevirus, Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazophos, Isofenphos, Isoxathion, Ivermectin, Nuclear polyhedrovirus, Lamda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Metaldehyd, Methamidophos, Metharhizium anisopliae, Metharhizium flavoviride , Methidathion, Methiocarb, Methomyl, Methoxyfenizide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos, Naled, Nitenpyram, Nithiazine, Novaluron, Omethoat, Oxamyl, Oxydemethon M, Paecilomyces fi mosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb , Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiophos, Prothoat, Pymetrozine, Pyrachlophos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion, Pyrimidifen, Pyriproxifen, Quinalphos. Ribavirin, Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos, Tau-fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Theta-cypermethrin, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thuringiensin, Tralocythrin, Tralomethrin, Triarathene, Triazamate, Triazophos, Triazuron, Trichlophenidine, Trichlorfon, Triflumuron, Trimethacarb, Vamidothion, Vaniliprole, Verticillium lecanii, Yl 5302, Zeta-cypermethrin, Zolaprofos, (1 R-cis) - [5 - (phenylmethyl) -3-cyanyl] -methyl-3 - [(dihydro-2-oxo-3 (2H) -franylidene) -methyl] -2,2-dimethylcyclopropanecarboxylate (3-phenoxyphenyl) -methyl-2,2,3 , 3 - tetramethylcyclopropanecarboxylate l - [(2-chloro-5-thiazolyl) methyl] tetral idro-3,5-dimethyl-N-mfro-l, 3,5-triazin-2 (lH) -imine 2- (2- chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazole 2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione 2-chloro-N- [[[4- (l-phenylethoxy) -phenyl] -amino] - carbonyl] -benzamide 2-chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) -phenyl] -amino] -carbonyl] -benzamide 3-methylphenyl-propylcarbamate 4- [4- ( 4-Ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene 4-chloro-2- (1, 1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -3 (2H) -pyridazinone 4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) -pyridazinone 4- chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) -pyridazinone Bacillus thuringiensis strain EG-2348 [2-benzoyl-l- (l, l-dimethyl) -hydrazide of benzoic acid butanoate of 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-l-oxaspiro [4.5] dec-3-en-4-yl [3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] -cianamide dihydro-2- (nitromethylene) -2H- 1, 3-thiazine- 3 (4H) -carboxaldehyde ethyl- [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] -carbamate N- (3, 4,4-trifluoromethyl) 1-oxo-3-butenyl) -glycine N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-lH-pyrazole-l-carboxamide N - [( 2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanide N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazindicarbotioamide N-methyl-N' -2-propenyl-, 1, 2-hydrazindicarbothioamide O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] -ethyl-phosphoramidothioate A mixture with other active ingredients, such as herbicides, is also possible. or with fertilizers and growth regulators. The active compounds according to the invention can also be present in their commercially available formulations as well as in the application forms prepared from these formulations in a mixture with synergists. The synergists are compounds through which the effect of the active products is increased without the synergetic aggregate having to be active in itself. The active ingredient content of the application forms prepared from the commercially available formulations can vary within wide limits. The concentration in active product of the application forms can be found from 0, 0000001 up to 95% by weight of active product, preferably between 0.0001 and 1% by weight.

The application is carried out in a form adapted to the forms of application. When used against hygiene pests and stored products, the active products are characterized by the outstanding residual effect on wood and clay as well as good alkali stability on whitewashed substrates. The active compounds according to the invention not only act against plant pests, hygiene and stored products, but also in the veterinary sector against animal parasites (ectoparasites) such as hard ticks, soft ticks, mites of the scabies, migratory mites, flies (choppers and suckers), larvae of parasitic flies, lice, hair nits, nits of feathers and fleas. To these parasites belong: From the order of the anopplides, for example Haematopinus spp., Linognathus spp., Pediculus, Pthirus spp., Solenopotes spp. From the order of the Mallofagos and the suborders of the amblicerines as well as the Isqunocerines, by. example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp. From the order of the dipterans and the suborders of the nematocerines as well as the brachykeri, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the siphonoptera, for example Pulex spp., Ctenocephalides spp., Xenospsylla spp., Ceratophyllus spp .; From the order of the heteroptera, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp. From the order of the blatarids, for example Blatta orientals, Periplaneta americana, Blattela germanica, Supella spp .. From the subclass of the mites (Acarida) and the suborder of the meta- as well as mesostigmata, for example Argas spp., Ornithodorus spp., Otabius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp. From the order of actinedides (Prostigmata) and acaridids (Astigmata), for example Acarapis spp., Cheyletieella spp. ., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterilichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. ., Laminosioptes spp .. By way of example, the active compounds of the formula (I), according to the invention, show an excellent activity against all the larval stages of the Lucilia cuprina fly. The active compounds according to the invention are also suitable for the control of arthropods, which attack animals useful in agriculture, such as, for example, cows, lambs, goats, horses, pigs, donkeys, camels, hippos, rabbits, chickens, ducks, turkeys, geese, bees, other domestic animals such as, for example, dogs, cats, game birds, aquarium fish as well as so-called test animals such as, for example, hamsters, guinea pigs, rats and mice . Through the fight against these arthropods deaths and decreases in productivity (in meat, milk, wool, skins, eggs, honey, etc.) are avoided, so that, by using the active products according to the invention, a more economical maintenance is possible and simple of the animals. The application of the active compounds according to the invention is carried out, in the veterinary sector, in a known manner by enteral administration in the form, for example of tablets, capsules, beverages, dragees, pastes, bolis, by means of the feed-through procedure, suppositories, by parenteral administration, such as for example by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal application, by dermal application in the form of for example immersion or bathing (Dippen), spray (Spray), irrigated (Pour-on and Spot- on), washed, powdered as well as with the aid of molded bodies containing the active product such as collars, ear tags, tail tags, limb bands, halters, marking devices etc. When used for livestock, poultry, domestic animals, the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, spreadable agents), containing the active compounds in amounts of 1 to 80% by weight. weight, directly or after a dilution of 100 to 10,000 times or can be applied as a chemical bath. It has also been found that the compounds of the formula (I) show a high insecticidal effect against the insects that destroy industrial materials.

In an exemplary and preferred way - however without limitation - the following insects can be mentioned: Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium cafine, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis; Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus. Hymenoptera, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur. Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicala, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucif gus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus. Thysanides, such as Lepisma saccarina. By industrial materials, non-living materials will be understood in the present context, such as, preferably, synthetic materials, glues, glues, paper and cardboard, leather, wood and wood processing products and paints. In a very special way, the materials to be protected against attack by insects are made of wood and wood products. For wood and wood processing products, which can be protected by means of the agents according to the invention or of the mixtures containing them, it should be understood, for example: construction wood, wooden beams, railway sleepers, parts for bridges, boat ribs, wooden vehicles, boxes, pallets, containers, telephone poles, wooden coverings, wooden windows and doors, wooden plywood, plywood boards, carpentry works or wood products, which find application, in a very general way, at home or in the construction industry.

The active compounds can be used as such, in the form of concentrates or customary formulations in general, such as powders, granules, solutions, suspensions, emulsions or pastes. Said formulations can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersants and / or binder or binding agent, water repellent, optionally drying agents and stabilizers. against UV and, if necessary, dyes and pigments as well as other processing aids. The insecticidal agents or concentrates to be used for the protection of wood and wood materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, especially 0.001 to 60% by weight. The amounts of the agents or concentrates used depend on the type and origin of the insects and the environment. The optimum application quantities can be determined respectively by means of series of tests prior to the application. In general, however, it is sufficient to employ from 0.0001 to 20% by weight, preferably from 0.001 to 10% by weight of the active product, based on the material to be protected. A solvent or a mixture of organochemical solvents and / or a solvent or mixture of organo-chemical, oleaginous or oil-like solvents, which are difficult to volate and / or a solvent or mixture of polar organochemical solvents, is used as solvent and / or diluent. and / or water and, if appropriate, an emulsifier and / or humectant. As organochemical solvents, oleaginous or oleaginous solvents are preferably used, with an evaporation value above and a flame point located above 30 ° C, preferably located above 45 ° C. By way of such water-insoluble, oil-insoluble or oleaginous-type solvents which are difficult to volatile, corresponding mineral oils or their aromatic fractions or solvent mixtures containing mineral oils will be used., preferably benzine for tests, petroleum and / or alkylbenzene. Advantageously, mineral oils with a boiling range of 170 to 220 ° C, benzine for tests with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatic hydrocarbons with a boiling range of 160 to 280 ° C, terpene oil and the like. In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C or a high-boiling mixture of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 220 ° C and / or oil for use are used. spindles and / or monochloronaphthalene, preferably a-monochloronaphthalene. Organic solvents, which are difficult to volatile, oleaginous or oil-based, with an evaporation index above 35 and with a flame point above 30 ° C, preferably above 45 ° C, can be partially replaced by solvents light or medium volatility organochemicals, provided that the solvent mixture has an evaporation index above 35 and a flame point above 30 ° C, preferably above 45 ° C, and that the insecticidal-fungicidal mixture is soluble or emulsifiable in this mixture of solvents. According to a preferred embodiment, a part of the solvent or mixture of organochemical solvents or a solvent or mixture of aliphatic, polar organochemical solvents will be replaced. Preference is given to using aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ether, esters or the like. As organic-chemical binders, synthetic resins and / or setting drying oils, known per se, dilutable with water and / or soluble or dispersible or emulsifiable in the organic-chemical solvents used, will be used within the scope of the present invention. especially binders consisting of or containing acrylic resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indeno-coumaron resin, silicone resin, vegetable drying and / or drying oils and / or physical drying binders based on a natural and / or synthetic resin. The synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In a complementary manner, dyes, pigments, water-repelling agents, odor correctors and inhibitors or anticorrosive agents known per se and the like can be used. It is preferred to use at least one alkyd resin or a modified alkyd resin and / or a drying vegetable oil in the medium or concentrate according to the invention as an organochemical binder. Preferably, alkyd resins having an oil content of greater than 45% by weight, preferably from 50 to 68% by weight, are preferably used according to the invention. The aforementioned binder can be partially or completely replaced by a fixing agent (mixture) or by a plasticizer (mixture). These additives should avoid volatilization of active products as well as crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used). The plasticizers are of the chemical class of phthalic acid esters such as dibutyl, dioctyl or benzylbutyl phthalate, phosphoric acid esters, such as tributyl phosphate, adipic acid esters, such as di- (D-adipate). 2-ethylhexyl), stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerin ethers or high molecular weight glycol ethers, glycerin esters as well as esters of p-toluenesulfonic acid. The fixing agents are chemically based on polyvinylalkyl ethers such as polyvinyl methyl ether or on ketones such as benzophenone, ethylenebenzophenone. Suitable as solvent or diluent is water, optionally mixed with one or more of the aforementioned solvents or diluents, emulsifier and organochemical dispersants. Especially effective protection of the wood is achieved by impregnation processes on an industrial scale, for example vacuum, double vacuum or pressure processes. The ready-for-application agents can optionally contain other insecticides and, if appropriate, one or more additional fungicides. The insecticides and fungicides mentioned in WO 94/29 268 are preferably used as additional components of the mixture. The compounds mentioned in this document are expressly an integral part of the present application. Particularly preferred mixing components are insecticides, such as Chlorpyriphos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron and Triflumuron, as well as fungicides such as Epoxiconazole, Hexaconazole. , Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Imazalil, Dichlorfluanid, Tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one . The preparation and use of the active compounds according to the invention is apparent from the following examples. Examples of obtaining. Example 1-1.

(Procedure A). 3.1 g (10 mmol) of ethyl N- [2- (4-bromophenyl) -2-chloroethyl] -carbamidate were dissolved (for example from example II-1) and 2.09 g (15 mmol) of 2,6-difluorobenzonitrile in 10 ml of concentrated sulfuric acid and stirred for 3 hours at room temperature, whereby the solution was colored dark. The load was then carefully poured onto ice. It was extracted twice with dichloromethane, the aqueous phase was made alkaline with sodium hydroxide and extracted again. The combined organic phases were extracted with saturated common salt solution, dried and concentrated by evaporation. The 4.4 g of crude product obtained was chromatographed through a column of silica gel (cyclohexane: ethyl acetate = 5: 1). 3.6 g (88% of theory) of 4- (4-bromophenyl) -l-ethoxycarbonyl-2- (2,6-difluorophenyl) -4,5-dihydro-1 H-imidazole were obtained as an oil viscous yellow 1 H-NMR (400 MHz, CDC13): d [ppm] 1.1 (t, 3H); 3.7 (m, 1H); 4.1 (q, 2 H); 4.4 (m, 1H); 5.4 (m, 1H); 6.9-7.6 (m, 7 H).

Example 1-2.

(Procedure A). Obtained, in a manner analogous to that of Example 1-1, from 3.1 g (10 mmol) of ethyl N- [2- (4-bromophenyl) -2-chloroethyl] -carbamidate (e.g. Example II-1) and 2.1 g (15 mmol) of 2-chlorobenzonitrile, 2.9 g (72% of theory) of 4- (4-bromophenyl) 2- (2-chlorophenyl) -l-ethoxycarbonyl- 4,5-dihydro-1H-imidazole as viscous colorless oil. ? -NMR (400 MHz, CDCl 3): d [ppm] 1.0 (t, 3H); 3.9 (m, 1H); 4.0 (q, 2 H); 4.4 (m, 1H); 5.3 (m, 1H); 7.2-7.6 (m, 8 H). Example 1-3.

(Procedure B). 3.6 g (9 mmol) of 4- (4-bromophenyl) -l-ethoxycarbonyl-2- (2,6-difluorophenyl) -4,5-dihydro-1H-imidazole were dissolved (for example from example 1- 1) in 25 ml of dimethoxyethane and combined with 20 ml of 1 molar solution of sodium carbonate. Subsequently, 2.9 g (11 mmol) of 4-trifluoromidoxyphenylboronic acid (85%) and finally as a catalyst, 336 mg (0.48 mmol) of dichloro-bis (triphenylphosphino) palladium (II) were added. The mixture, initially yellow, is heated to reflux, with which a brown solution is formed. It was refluxed overnight, combined with water after cooling and extracted with ethyl acetate. The combined extracts were washed successively with ammonium chloride solution, with water and with common salt solution, concentrated by evaporation and chromatographed through a column of silica gel (cyclohexane: ethyl acetate = 10: 1). 2.50 g (57% of theory) of 1-ethoxycarbonyl-4- (4, -trifluoromethoxy-4-biphenyl) -2- (2,6-difluorophenyl) -4,5-dihydro-1H-imidazole were obtained. . Melting point: 105-107 ° C. Example 1-4 (Procedure B). In a manner analogous to that of Example 1-3, from 1.5 g (9.0 mmol) of 4- (4-bromophenyl) -2- (2-chlorophenyl) -1-ethoxycarbonyl-4,5 were obtained -dihydro- 1 H-imidazole (for example from example 1-2) and 1.0 g (4.8 mmoles) of 4-trifluoromethoxyphenylboronic acid, 1.38 g (76% of the theory) of 2- (2 chlorophenyl) -l-ethoxycarbonyl-4- (4'-trifluoromethoxy-4-biphenylyl) -4,5-dihydro-1H-imidazole as a colorless oil. 1 H-NMR (400 MHz, CDC13): d [ppm] 1.0 (t, 3H); 3.9 (m, 1H); 4.0 (q, 2H); 4.4 (m, 1H); 5.4 (m, 1H); 7.2-7.6 (m, 12H). Example 1-5 d-5a) (I-5b) (Method c). They were passed through a solution of 2.6 g (3.1 mmol) of 4- (4'-trifluoromethoxy-4-biphenylyl) -2- (2,6-difluorophenyl) -4,5-dihydrole H-imidazole (for example from example V1) in 260 ml of dichloromethane, at 5 ° C, 22.9 g (0.37 mol) of chlorocyano. Stirring was continued for 45 minutes at 0-5 ° C. A solution of 15.6 g (0.39 mole) of sodium hydroxide in 140 ml of water (10% strength) was then added dropwise. After separation of the organic phase, the aqueous phase was extracted with dichloromethane, the combined organic phases were washed with water, dried and concentrated by evaporation under vacuum of the water (30 ° C). 2.9 g of crude product were obtained, which were separated by column chromatography (silica gel 0 = 3 cm, 1 = 30 cm; cyclohexane gradient: ethyl acetate 7: 1 to 5: 1). 1.55 g (57% of theory) of l-cyano-4- (4'-trifluoromethoxy-4-biphenylyl) -2- (2,6-difluorophenyl) -4,5-dihydro-1H- were obtained. imidazole (I-5a) and 0.80 g (30% of theory) of 3-cyano-4- (4'-trifluoromethoxy-4-biphenylyl) -2- (2,6-difluorophenyl) -4,5- dihydro-3H-imidazole (I-5b). (I-5a): melting point: 123-124 ° C. (I-5b): 1 H-NMR (500 MHz, DMSO): d [ppm] 4.1 (m, 1H); 4.7 (m, 1H); 5.7 (m, 1H); 7.4-7.9 (m, 11 H). Example 1-6 (I-6a) (I-6b) (Procedure C). A solution of 1.5 g (3.6 mmol) of 4- (4'-trifluoromide toxy-4-biphenylyl) -2- (2,6-difluorophenyl) -4.5- was combined at 0 ° C. dihydro-1H-imidazole (for example from example V1) in 15 ml of dichloromethane, firstly with 0.75 ml (0.55 g, 5.4 mmol) of triethylamine and then with 4 ml (0.degree. 41 g, 4.32 mmol) of chloromethylethylether. After stirring overnight, approximately 50% of the educt (DC) was still present. Another 0.25 ml of triethylamine and 0.17 ml of ether were added. Since no further reaction could no longer be detected, 0.25 ml of triethylamine was added again and heated to boiling. For work-up, the reaction mixture was extracted with 10% citric acid and with IN sodium hydroxide solution, dried, concentrated by evaporation and chromatographed on a silica gel column (0 = 3 cm, 1 = 30 cm). By elution with cyclohexane / ethyl acetate with a gradient in five stages from 20: 1 to 3: 1, 0.30 g (17% of theory) of 1-ethoxymethyl-4- (as a second fraction) was obtained. 4'-trifluoromethoxy-4-biphenylyl) -2- (2,6-difluorophenyl) -4,5-dihydro-1H-imidazole (I-6a) and, as a third fraction, 0.34 g (20% of the theory) of 3-ethoxymethyl-4- (4Mrifluoromethoxy-4-biphenylyl) -2- (2,6-difluorophenyl) -4,5-dihydro-3H-imidazole (I-6b). (I-6a): 1 H-NMR (400 MHz, DMSO): d [ppm] 1.0 (t, 3H): 3.2-3.5 (m, 2 + 1H); 4.1 (m, 1 HOUR); 4.4 (s, 1H); 5.3 (m, 1H); 7.2-7.9 (m, 11H) (I-6b): 1 H-NMR (400 MHz, DMSO): d [ppm] 0.9 (t, 3H); 3.1-3.3 (m, 2H); 3.7 (m, 1 HOUR); 4.2 (m, 2H); 4.4 (m, 1H): 5.1 (m, 1H): 7.2-7.9 (m, 11H). Example 1-7.

(I-7a) (I-7b) (Procedure C). 1.5 g 3.6 mmoles) of 4- (4'-trifluoromethoxy-4-biphenylyl) -2- (2,6-difluorophenyl) -4,5-dihydro-1 H-imidazole were dissolved (e.g. Example V1) in 20 ml of toluene were combined with 1.7 ml (1.84 g, 18 mmol) of acetic anhydride and boiled for 1 hour at reflux. It was then concentrated by evaporation and the residue was recrystallized from a mixture of cyclohexane and ethyl acetate. 1.07 g (65% of theory) of l-acetyl-4- (4'-trifluoromethoxy-4-biphenylyl) -2- (2,6-difluorophenyl) -4,5-dihydro-1H- were obtained imidazole (I-7a). 0.6 g of the concentration residue were removed by evaporation of the mother liquors by column chromatography (silica gel, 0 = 3 cm, 1 = 30 cm, cyclohexane: ethyl acetate = 5: 1). As a second fraction, 0.12 g (7% of the theory) of 3-acetyl-4- (4'-trifluoromethoxy-4-biphenylyl) -2- (2,6-difluorophenyl) -4.5- were obtained. dihydro-3H-imidazole (I-7b) in the form of oil. (I-7a): Melting point: 109-111 ° C. (I-7b): 1 H-NMR (400 MHz, DMSO): d [ppm] 1.9 (t, 3H); 3.7 (m, 1H); 4.6 (m, 1H); 5.6 (m, 1H); 7.2-7.9 (m, 11 H). Example 1-8.

(Procedure D). 1.0 g (2.3 mmol) of l-cyano-4- (4'-trifluoromethoxy-4-biphenylyl) -2- (2,6-difluorophenyl) -4,5-dihydro-1H-imidazole was placed. (for example from example 1-5, compound I-5a) in 15 ml of pyridine for analysis under argon. Hydrogen sulfide was passed through it at room temperature for 30 minutes, stirring was continued for 1.5 hours and then the remaining hydrogen sulfide was expelled. For working up, it was concentrated by evaporation in a vacuum, toluene was added and it was again concentrated by evaporation. The residue of 1.2 g was purified by chromatography (silica gel, 0 = 3 cm, 1 = 30 cm, cyclohexane gradient: ethyl acetate 4: 1 to 1: 2). The crystalline product obtained, which melted at 93-95 ° C, contained, in accordance with the spectrum 2D-NMR and GC-MS, in addition to 10% of the 4- (4'-trifluoromethoxy-4-biphenylyl) -2- (2,6-difluorophenyl) -1-thiocarbamoyl-4,5-dihydro-1H-imidazole desired, the N-unsubstituted imidazoline (Vl). MS (Cl): m / z: 477 (M +). Example 1-9.

(Procedure D). Analogous to Example 1-8, from 0.5 g (1.15 mmol) of 3-cyano-4- (4'-trifluoromethoxy-4-biphenylyl) -2- (2.6 -difluorophenyl) -4,5-dihydro-3H-imidazole (for example from example 1-3, compound I-3b), 0.50 g of crude product. Column chromatography (silica gel; 0 = 3 cm, 1 = 30 cm; cyclohexane gradient: ethyl acetate 8: 1 to 2: 1) gave 0.17 g of N-substituted imidazoline (Vl), which, according to the 1 H-NMR spectrum and GC-MS contained small proportions of 4- (4 -trifluoromethoxy-4-biphenylyl) -2- (2,6-difluorophenyl) -thiocarbamoyl-4,5-dihydro-3 H-imidazole desired. MS (Cl): m / z: 477 (M +). Obtaining the starting products. Example II-l. 9.8 ml (13.7 g, 0.075 mole) of p-bromostyrene was dissolved in 50 ml of acetonitrile for analysis and swept with an argon copy. A solution of 12 g (0.075 mole) of ethyl N, N-dichlorocarbamidate in 50 ml of acetonitrile was added dropwise at 5 to 10 ° C for analysis so slowly that the temperature did not exceed 10 ° C. ° C. Then, stirring was continued for 3 hours at room temperature. According to the reaction controls by GC (approximately 88% of product), 75 ml of a 20% solution of sodium bisulfite (exothermic reaction) were added under cooling at 5 to 10 ° C. After separation of the phases, the aqueous phase was extracted with twice 20 ml of diethyl ether. The combined organic phases were extracted with saturated sodium chloride solution and with water, dried and concentrated by evaporation. 22.10 g (96% of theory) of the crude ethyl N- [2- (4-bromophenyl) -2-chloroethyl] -carbamidate was obtained, which was then directly reacted. Melting point: 61-62 ° C. Example V-l. 2 g (4.08 mmol) of 4- (4'-trifluoromethoxy-4-biphenylyl) -l-ethoxycarbonyl-2- (2,6-difluorophenyl) -4,5-dihydro-1 H-imidazole (by example from example II-2), at room temperature, to a solution / suspension of 1.1 g (20 mmol) of potassium hydroxide in 15 ml of ethanol for analysis. After stirring for 1 hour under refluxing and conversion controls by DC, the mixture was cooled, poured into water and extracted with tert-butyl methyl ether. After drying and concentration by evaporation of the combined extracts, 1.7 g of the crude product were obtained. This was stirred with a mixture of dichloromethane and cyclohexane and was separated by filtration by suction of the precipitated crystals. The mother liquors were concentrated by evaporation and again stirred with a small amount of the mixture and a second crystal fraction was obtained.

Yield: 1.00 g (60% of theory) of 4- (4'-trifluoromethoxy-4-bife-nilyl) -2- (2, t-difluorophenyl) -4,5-dihydro-1 H-imidazole. Melting point: 125-127 ° C. Application examples: Example A Phaedon larvae test Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration. Cabbage leaves (Brassica olerácea) are treated by immersion in the preparation of active compound of the desired concentration and are covered with larvae of the horseradish leaf beetle (Phaedon cochleariae), while the leaves are still moist. After the desired time the destruction is determined in%. In this case 100% means that all the beetle larvae were destroyed, 0% means that no beetle larvae were destroyed. In this test, for example, the compounds according to Preparation Examples 1-4, I-5a, I-5b, I-6a, I-6b and 1-8, were shown at an exemplary concentration of active compound of 0.1. %, after 7 days, a degree of destruction of 100%, that of the obtaining example I-7a, a degree of destruction of, 90%. EXAMPLE B Assay with Spodoptera Solvent: 7 parts by weight of dimethylformamide.

Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration. Cabbage leaves (Brassica olerácea) are treated by being dipped into the preparation of the active compound of the desired concentration and covered with caterpillars of the autumn legionary (Spodoptera frugiperda), while the leaves are still moist. After the desired time, the degree of destruction in% is determined. In this case 100% means that all caterpillars were destroyed; 0% means that no caterpillar was destroyed. In this test they showed, for example, at a concentration of active compound of 0.1%, after 7 days, the compounds according to the preparation examples 1-4, 1-3, 1-5a, I-5b, I -6a, I-7a and 1-8, a degree of destruction of 100%. Example C Test with Tetranychus (OP-resistant / dip treatment) Solvent: 7 Parts by weight of dimethylformamide Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the indicated amount of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. Bean plants (Phaseolus vulgaris) are treated by immersion, which are strongly attacked by all the stages of mite debris of the common red spider mite (Tetranychus urticae), in a preparation of the active product of the desired concentration.

After the desired time, the effect in% is determined. In this case they mean 100% that all the spider mites were killed; 0% means that no spider mite was killed. In this test, after 7 days, for example, the compounds according to Preparation Examples 1-3, I-5a, I-5b, I-6a and I-7a were shown at an exemplary concentration of the active compound of the invention. , 01% a degree of destruction of 100% and that of the obtaining example 1-8, a degree of destruction of 95%. Example D Test with Blo fly larvae / developmental inhibitor effect. Test animals: Lucilia cuprina larvae Solvent: Dimethylsulfoxide. 20 mg of active compound are dissolved in 1 ml of dimethyl sulfoxide, the lower concentrations are prepared by dilutions of distilled water. Approximately 20 Lucilia cuprina larvae are placed in test tubes, containing approximately 1 cm3 of horse meat and 0.5 ml of the preparation of active product to be tested. After 24 and 48 hours the activity of the preparation of the active product is determined. The test tubes are transferred to cups with the bottom covered with sand. After another 2 days, the test tubes are removed and the number of pupae is counted. The effect of the preparation of the active product is evaluated according to the number of flies that have hatched after 1.5 times the development time of an untreated control. In this case 100% means that no fly hatched; 0% means that all flies normally hatched. In this test the compounds according to the preparation examples I-3 and I-4a showed, at a concentration of the active compound of 100 ppm, a 100% effect. It is noted that in relation to this date, the best method known to the applicant, to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims (11)

2. Having described the invention as above, the contents of the following claims are recited as property: 1. Compounds of the formula (I) characterized because: Ar1 means the grouping (a) wherein R 1 signifies halogen, alkyl, alkoxy or halogenoalkoxy and R 2 signifies hydrogen, halogen, alkyl or alkoxy, Ar 2 means groupings (b) or (c) wherein R3, R4, R5 and R6, independently of each other, mean, respectively, hydrogen, halogen, alkyl, alkoxy, haloalkyl or haloalkylthio, R7 means hydrogen, halogen, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio and Y means a direct bond, oxygen, methylene, -O-CH2- or -CH2O- and R means cyano, alkoxyalkyl, formyl, alkylcarbonyl, alkoxycarbonyl or -C (X) -NHR8, where X means oxygen or sulfur and R8 means hydrogen or alkyl. 2. Compounds of the formula (I) according to claim 1, characterized by Ar1 means the grouping (a) wherein R 1 signifies halogen, alkyl having 1 to 3 carbon atoms, alkoxy with 1 to 3 carbon atoms or halogenalkoxy with 1 to 3 carbon atoms and R¿ means hydrogen, halogen, alkyl having 1 to 3 carbon atoms or alkoxy with 1 to 3 carbon atoms, Ar means groupings (b) or (c) wherein R3, R4, R5 and R6 independently of each other, respectively mean hydrogen, halogen, alkyl having 1 to 12 carbon atoms or alkoxy with 1 to 12 carbon atoms, R7 signifies hydrogen, halogen, cyano, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms, halogenoalkyl with 1 to 6 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or halogenalkylthio with 1 to 4 carbon atoms, Y means a direct bond or means oxygen and R means cyano, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbon, C 1 -C 4 -alkoxycarbonyl or - C (X) -NHR8, wherein X means oxygen or sulfur and R means hydrogen or alkyl having 1 to 4 carbon atoms. 3. Compounds of the formula (I) according to claim 1, characterized in that Ar1 means the grouping (a) wherein R 1 signifies fluorine, chlorine, bromine, iodine, alkyl having 1 to 3 carbon atoms and alkoxy with 1 to 3 carbon atoms and R means hydrogen, fluorine, chlorine, bromine, alkyl having 1 to 3 carbon atoms or alkoxy with 1 to 3 carbon atoms, Ar means groupings (ba) or (ca) in which R3, R4, R5 and R6 independently of each other, respectively, mean hydrogen, fluorine, chlorine, bromine, iodine, alkyl having 1 to 6 carbon atoms or alkoxy with 1 to 6 carbon atoms, R7 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, alkyl with 1 to 7 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or alkylthio with 1 to 4 carbon atoms substituted by fluorine or chlorine, R means cyano, C 1 -C 3 alkoxy-C 1 -C 3 -alkyl, C 1 -C 3 -alkylcarbonyl , alkoxycarbonyl having 1 to 2 carbon atoms or -C (X) -NHR8, where R means hydrogen or alkyl having 1 to 4 carbon atoms, X means oxygen or sulfur. 4. Compounds of the formula (I) according to claim 1, characterized perqué
3. Ar1 means groupings (a-1), (a-2) or (a-3) (a-1) < a-2). (a-3). wherein R1 means fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy and R means hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy, or ethoxy, Ar2 means groupings (b-b) or (c-b) in which R3, R4, R5 and R6 independently of each other, respectively, mean hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.-butyl, tere-butyl , pentyl, hexyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec.-butoxy, tert-butoxy, pentyloxy or hexyloxy,
4. R7 is fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tere-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n- butoxy, isobutoxy, sec .-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, 1,1-difluoroethoxy, 1,1,2-trifluoroethoxy, 1,1 , 2,2-tetrafluoroethoxy, 2-chloro-l, l, 2-trifluoroethoxy, 2,2,2-trichloro-1, 1 -diflúoretoxi, pentafluoroethoxy, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, 1,1-diflúoretiltio, 1.1 , 2-triflúoretiltio, 2,2,2-triflúoretiltio, 1,1,2,2-tetraflúoretiltio, 2-chloro-l, l, 2-triflúoretiltio, 2,2,2-trichloro-l, l- diflúoretiltio or pentaflúoretiltio R means cyano, ethoxymethyl, acetyl, propionyl, butyryl, methoxycarbonyl, ethoxycarbonyl or -C (X) NHR8, where R means hydrogen, methyl or ethyl, X means oxygen or sulfur.
5. 5. Process for obtaining compounds of the formula (I) according to claim 1, characterized in that A) diphenylimidazolines of the formula (I-a) are obtained wherein Ar1 and Ar2 have the meanings indicated above and R9 means alkyl with 1 to 4 carbon atoms, by condensation of β-chlorocarbamates of the formula (II) wherein 7 O Ar and R have the meanings indicated above, with benzonitriles of the formula (III), Ar'-CN (III), in which Ar1 has the meanings given above, in the presence of sulfuric acid, or B) diphenylimidazolines of the formula (Ib) are obtained wherein R has the meanings given above and R1"1 represents fluorine, chlorine, alkyl, alkoxy or haloalkoxy, R2" 1 represents hydrogen, fluorine, chlorine, alkyl or alkoxy, R5"1 and R6" 1 independently of one another, each hydrogen, fluorine, chlorine, alkyl, alkoxy, halogenoalkoxy or halogenoalkylthio and R7"1 represents hydrogen, fluorine, chlorine, cyano, alkyl, alkoxy, alkylthio, halogenoalkyl or halogenoalkoxy, by coupling halogen compounds of the formula (Ic) wherein R, R1"1, R2" 1 and R5"1 have the meanings indicated above, and Z means bromine or iodine, with boronic acids of the formula (IV) wherein R6"1 and R7" 1 have the meanings indicated above, in the presence of a catalyst and, if appropriate, in the presence of an acid-accepting agent, as well as, if appropriate, in the presence of a diluent, or ) diphenylimidazolines of the formula (I) are obtained, wherein Ar1, Ar2 and R have the meanings indicated above, by condensation of diphenyl imidazolines not substituted on nitrogen, of the formula (V) wherein 1 7 Ar and Ar have the meanings indicated above, with compounds of the formula (VI) R-X 1 (VI) in which R has the meanings given above and X 1 means a suitable dissociable group, as a function of the rest R , such as -Cl, -Br, -OSO2OR10 or -OR10, where R10 means alkyl or aryl, if appropriate in the presence of a reaction auxiliary agent, or D) diphenylimidazolines of the formula (Id) are obtained wherein Ar1, Ar2 and X have the meanings indicated above, by reaction of nitriles of the formula (I-e) wherein 1 • Ar and Ar have the meanings given above, with water or with hydrogen sulphide, if appropriate in the presence of an auxiliary agent of the reaction.
6. 6.- Compounds of the formula (V) characterized park Ar1 and Ar2 have the meanings indicated in claim 1.
7. 7.- Pesticidal agents, characterized in that they have a content in at least one compound of the formula (I) according to claim 1.
8. 8.- Use of the compounds of the Formula (I) according to claim 1, for the control of pests.
9. 9. Procedure for the control of pests, characterized in that compounds of the formula (I) according to claim 1 are allowed to act on the pests and / or on their environment.
10. 10. Process for obtaining pesticidal agents, characterized because compounds of the formula (I) according to claim 1 are mixed with extenders and / or with surfactants.
11. 11. Use of compounds of the formula (I) according to claim 1, for obtaining pesticidal agents. RESULTS OF THE INVENTION The invention relates to novel diphenyl imidazolines of the formula (I) in which Ar !, Ar2 and R have the meanings indicated in the description, to several procedures for obtaining them and to their use for the fight against animal pests.