ARYLCYCLOALKYL ETHER DERIVATIVES, THEIR USE AND PREPARATION

Abstract: Arylcycloalkyl ether derivatives having the formula (I), wherein R represents certain optionally chloro- or fluorosubstituted phenoxybenzyl groups, certain heterocyclic or unsaturated groups or certain aryl groups, R1 represents hydrogen, halogen, straight or branched chain C1 - C6 alkyl, straight or branched chain C1 - C6 alkoxy or C1 - C6 haloalkyl, R2 represents hydrogen, halogen, C1 - C6 alkyl, C1 - C6 alkoxy or C1 - C6 haloalkyl, or R1 and R2 together form a methylendioxy group, R3 represents hydrogen, halogen or C1 - C6 alkyl, X and Y each independently represents hydrogen or halogen, m is an integer of from 1 to 5, and n is an integer of from 0 to 3, which derivatives can be prepared in a known manner, have pesticidal and particularly insecticidal, acaricidal and tickicidal activities, and said derivatives and compositions containing them are thus applicable for combating pests and particularly insects, acarids and ticks.

Description: Arylcycloalkyl ether derivatives, their use and prepa¬ ration. The present invention relates to novel aryl¬ cycloalkyl ether derivatives having biocidal properties, particularly insecticidal, acaricidal and tickicidal properties. The invention also relates to a pesticide based on the arylcycloalkyl ether derivatives of the invention and the use of said derivatives for combating pests, as well as their preparation. The arylcycloalkyl ether derivatives of the invention are characterized by being novel compounds of the general formula I wherein R represents a group of one of the following formulae A to M O PI I K R, represents a hydrogen or halogen atom, a straight or branched chain alkyl group of 1 to 6 carbon atoms, a straight or branched chain alkoxy group of 1 to 6 carbon atoms or a haloalkyl group of 1 to 6 carbon atoms, R~ represents a hydrogen or halogen atom, an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms or a haloalkyl group of 1 to 6 carbon atoms, or R-, and R 2 together form a methylenedioxy group, R 3 represents a hydrogen or halogen atom or an alkyl group of 1 to 6 carbon atoms, X and Y each independently represents a hydrogen or halogen atom, OMPI ' m is an integer of from 1 to 5, and n is an integer of from 0 to 3. Formula I is to be regarded as comprising racemates as well as optically active isomers of the compounds of the invention. Particularly preferable according to the inven¬ tion are arylcycloalkyl ether derivatives of the general formula I, wherein R represents a group of one of the formulae A, B, C or K as stated above, R, represents a hydrogen atom, R 2 represents a halogen atom or an ethoxy, difluoro- methoxy, methoxy, methyl, ethyl or isopropyl group, or R. and R 2 together form a methylenedioxy group, R_ represents a hydrogen atom, m is 1 or 3, and n is 0 or 1. As mentioned above the invention also relates to a pesticidal composition, particularly an insecti¬ cide, acaricide or tickicide, which is characterized by containing as an active component an arylcycloalkyl ether derivative according to the invention. Furthermore, the invention relates to a method for combating pests, particularly insects, acarids or ticks, which method is characterized by applying to a locus attacked by or liable to be attacked by the pest concerned, an arylcycloalkyl ether derivative according o the invention or a preparation containing at least one such derivative. The invention also relates to the use of aryl- cycloalkyl ether derivatives according to the invention for combating pests, particularly insects, acarids or ticks. The arylcycloalkyl ether derivatives of the invention may be prepared by a process, in which a compound of the general formula I, wherein R represents a hydrogen atom, and R, , R 2 , R- , X, Y, m og n are as defined above, is reacted with a chloride of the formu¬ la R-Cl, wherein R is as defined above, in the presence • of a base and a catalyst and in the presence or absence of a solvent. By means of the arylcycloalkyl ethers according to the invention a pesticidal composition can be pre- pared in the form of a pesticidal preparation containing a carrier or a surface-active agent or both a carrier and a surface-active agent, and at least one of the arylcycloalkyl ethers of the invention. The term "carrier" as used in the present speci- fication means a solid or liquid material which may be inorganic or organic and of synthetic or natural origin, with which the active compound is mixed or formulated to facilitate its application to plants, seeds, the soil or other objects to be treated, or its storage, transport or handling. The surface-active agent may be an emulsifying agent, a dispersing agent or a wetting agent, and it may be nonionic or ionic. Any of the carriers or surface-active agents usually employed in formulating pesticides may be used for the compositions according to the invention, and suitable examples thereof are described, e.g., in British patent specification No. 1,232,930. The compositions of the invention may be formula- ted as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension con¬ centrates or aerosols. Wettable powders are usually formulated to contain 25, 50 or 75% of active component and usually contain, in addition to solid carrier, 3-10% by weight of a dispersing agent and, where necessary,0-10% by weight of stabilisers and/or additives such as penetrants or stickers. Dusts are usually formulated as a dust concen¬ trate having a similar composition to that of a wettable powder but without a dispersant and are diluted in the field with further solid carrier to give a composition usually containing 1/2-10% by weight of active compo¬ nent. Granules are usually prepared to have a size • between 10 and 100 BS mesh, (1.676-0.152 mm) and may be manufactured by agglomeration or impregnation techniques. Generally, granules will contain 1-25% by weight of active component and 0-10% by weight of additives such as stabilisers, slow release modifiers and binding agents. Emulsifiable concentrates usually contain, in addition to the solvent and, when necessary, co-solvent, 10-50% w/v active component, 2-20% w/v emulsifiers and 0-20% w/v of appropriate additives such as stabilisers, penetrants and corrosion inhibitors. Suspension concentrates are compounded so as to obtain a stable, non-sedimenting, flowable product and usually contain 10-75% by weight of active component, 1/2-15% by weight of dispersing agents, 0.1-10% by weight of suspending agents such as protective colloids and thixo- tropic agents, 0-10% by weight of appropriate additives such as defoamer-s, corrosion inhibitors, stabilisers, penetrants and stickers, and as carrier, water or an organic liquid in which the active component is substantially insoluble. Certain organic solids or inorganic salts may be dissolved in the carrier to assist in preventing sedimentation or as antifreeze agents for water. Aqueous dispersions and emulsions, for example, compositions obtained by diluting a wettable pov/der or a concentrate according to the invention with water, also lie within the scope of the present invention. The said emulsions may be of the water-in-oil or the oil-in-water type, and may have a thick "mayonnaise"- like consistency. The compositions may also contain other ingredi¬ ents, for example, other compounds having pesticidal, particularly acaricidal, herbicidal or fungicidal properties. The compounds of the invention possess pestici¬ dal and especially insecticidal properties, which are superior to the properties of some of the known common¬ ly used pyrethroids , e.g., permethrin (52645-53-1) (3-phenoxybenzyl-2,2-dimethyl-3-(2,2-dichlorovinyl)- cyclopropane carboxylate) and fenvalerate (51630-58-1) (α-cyano-3-phenoxybenzyl-2-(4-chlorophenyl)-3-methyl butyrate and allethrin (584-79-2) and cismethrin (10453-86-8) . The figures indicated in parentheses are the so-called CAS numbers. With regard to the pesticidal spectrum the compounds of the invention exhibit a selective or non-selective activity on organisms of various orders such as Coleoptera, Lepidoptera, Diptera, Orthoptera, Hemiptera, Homoptera, Dictyoptera and Acarina.The compounds have a distinct vapour activity and are active against soil living insect pests. Other important properties of these compounds are that they are active against insect pests which are resistant to pesticides hitherto used, because the basal structure of the compounds differs from that of the known pesticides to which the insects are resistant, and that they possess a generally low toxicity against mammals, fish and man. Examples of insecticidal and acaricidal activi¬ ties against various pests are given below. The effect of the compounds can be substantially increased by means of known synergists, and the compounds have a remarkable effect against resistant insects or acarids. In the following Examples A denotes complete or almost complete kill, B_ some kill and C extremely low kill. The Tables of results show the results from the testing of test compounds as well as from the testing of known standard insecticides. Comparative tests illustrating the above-men¬ tioned circumstances and other properties characteri¬ zing the compounds of the invention are stated in the following Examples 45 to 62, whereas Examples 1 to 44 illustrate the preparation of the compounds of the invention. In the Examples 45 to 62 the tested compounds of the invention are only designated by a figure corre- ponding to the number of the Example of preparing the compound concerned. OMP Synthesis Example 1 (Method A) Preparation ' of 1-(4-difluoromethoxyphenyl)cyclopropyl- methyl-3-ρhenoxybenzyl ether. A mixture of 1-(4-difluoromethoxyphenyl)cyclo- propylmethanol (0.71 g) , 3-phenoxybenzylchloride (0.66g) and triethylbenzylammoniumchloride (0.23 g) is heated to 56 C on an oil bath. To this mixture a 50% aqueous solution of sodium hydroxide (6.0 g) is added in one portion. The mixture is kept under vigorous stirring o at 56 C for one hour and is then poureα onto ice-cooled 4 N hydrochloric acid (50 ml) . Extraction is performed with ether (2 x 30 ml) and the ethereal phase is dried over sodium sulphate and evaporated under reduced pressure to a slightly coloured oil. The oil is subject- ed to chromatography on a column of silica gel (25 g) , eluting with a 9:1 mixture of n-hexane and ethyl ace¬ tate to thereby give the desired product as a colour¬ less oil. The yield is 0.90 g (68%). 25 n" : 1.5581 δCDCl 3 (ppm) : 0.85 (4 H, S) , 3.53 (2 H, S) , 4.47 (2 H, S) , 6.47 (1 H, S, J = 75 Hz), 6.80 - 7.57 (13 H, m) . Synthesis Example 2 (Method B) Preparation of 1-(4-ethoxyphenyl)cyclopropylmethyl-3- phenoxybenzyl ether. A suspension of sodium hydride (0.50 g of a 55-60% dispersion in mineral oil washed free from mineral oil with petroleum ether) in a mixture of toluene (8 ml) and dimethylformamide (1 ml) is heated at 85°C on an oil bath. To this mixture a solution of 1-(4-ethoxyphenyl)cyclopropyl ethanol (0.87 g) in toluene (8 ml) is added dropwise. The mixture is stir¬ red at 85°C for 30 minutes, whereupon solid potassium iodide (0.70 g) is added in one portion. Finally a solution of 3-phenoxybenzylchloride (1.00 g) in toluene (2.5 ml) is added and the reaction mixture is boiled under reflux for 3 hours. After cooling to room temperature hydrolysis is performed with 4 N hydrochloric acid (20 ml) . The toluene phase is separa- ted, and the> aqueous phase is extracted with ether (2 x 2 ml) . The organic phases are combined, dried over sodium sulphate and evaporated under reduced pressure to give a brownish oil (1.80 g) . The oil is subjected to chromatography on a column of silica gel (25 g) , eluting with a 9:1 mixture of n-hexane and ethyl acet¬ ateto thereby give the desired product as a colourless oil. The yield is 1.24 g (73%) . n^ 6 : 1.5761 δCDCl 3 (ppm) : 0.80 (4H, S) , 1.37 (3 H, t, J = 7 Hz), 3.48 (2 H, S) , 3.97 (2 H, q, J = 7 Hz), 4.41 (2 H, S), 6.65 - 7.47 (13 H, m) . Examples 3 to 44 By a similar procedure to that described in Example 1 or 2 further compounds of the invention are prepared. These compounds together with their physical characteristics are tabulated in Table I below. Table I Example Formula Method Refractive MR spectrum No. " index/m.p. (CDC1 3 ) n D 25.. . i.a -t,s»β.a 0 (2 .8 H 3 fS (4 ) > H 3 .S >g ) 3 , 3 (2 .5 H 0 >s)f ^^ ■ -lr 4.28 (2 H,S), 5.95 (1 H,S), 7.17 - 7.47 (10 H,m) 12 A 4 s - 1.5693 0.78 (4 H,S), 3.45 (2 H.S), 3.92 (2 H.S), 4.28 (2 H.S), 5.90 (2 H.S) , 5.96 (1 H,S), <' 2fO? & 6.59 - 7.07 (3 H,m), 7.24 (1 H,S), 7.28 (5 H.S) 13 A 4 s - 1.5861 1.35 - 2.23 (8 H,m), -^ o- r--χ~- 3.40 (2 H.S), 4.35 . (2 H.S), 6.69 - 7.60 (13 H.m) 14 A , 2.31 . ». 5 = 1.5793 0.83 (4 H,S) (3 H.S), 3.55 (2 H.S), 4-45 (2 H.S) , 6.78 - 7.60 (13 H.m) 15 W j Oy- A 0.83 (4 H.S) , 3.53 1.5826 (2 H.S), 3.85 (6 H.S), 4.47 (2 H.S), 6.67 - 7.63 ( 12 H.m) A 0.91 (4 H.S), 3.57 17 -_ 5 = 1.5472 (2 H.S), 4.47 (2 H, S), 6.80 - 7.77 (13 H.S) 18 A 0.81 (4 H,S), 3.50 s_?r*r-§>_ ■ ? ■ • 1.5920 (2 H.S), 4.47 (2 H, S), 5.93 (2 H.S), 6.59 - 7.50 (11 H.m) f OMH Table I (Cont.) Example Formula Method Refractive NMR spectrum No. index/m.p. (CDCL 19 20 21 ': 1.5845 0.67 - 0:38 (4 K,-.), 1.12 (3 K,d, J = 6.5 Hz), 3.10 (1 H.c, J = < )§ - 0 ^ ^ 6.5 Hz), 4.63 (2 H.S), 5.93 (2 K.S), 6.77 - 7.60 (12 K.-Λ) 23 0.32 (4 H.SJ, 3.51 -T&f 1.54S2 (2 H.S), 4.40 (2 H.S), .- L<- 6.33 - 7.62 (12 E.ai) Table I (Cont.) Ex≤π-TPle Formula Method Refractive NMR spectrum No. " ir-dex/m.p. (CDC1 3 ) 41 Z. .52 ^=^gr°^x. τι O~: 1.5718 0.S4 (4 K.S), 3 (2 H.S), 4.45 (2 K.S) , 6.77 - 7.50 ( 12 K,a) Table I (Cont . ) - E-<---- pie For_τrαla Method Refractive K5S spectrum ] _ Q Example 45 Musca domestica L. (Common house fly) . Acetone solutions or formulations of the compounds to be tested are prepared in a concentration of 0.025 micrograms per microlitre. 15 Adult flies anaesthetized with carbon dioxide/ ether are treated with a 2 microlitre drop per insect of the solution of the test compound.20 Flies are treated with each compound, the flies having free access to water and sugar in the test period of 48 hours. The 20 number of dead and moribund flies is counted at the end of the test period. Compound Insecticidal activity 1 A 25 2 A 4 A 9 A 20 A 13 A 30 3 B 11 B 17 B Cismethrin B 8 C 35 5 C Allethrin C 22 A OMPI ^ MAΎ Compound Insecticidal activity 23 A 26 A 27 A 28 A 29 A 39 B 40 A 41 B 42 B 44 ' B In a test on multiresistant house flies (strain 381 zb, from the Danish Pest Infestation Laboratory) , the compounds mentioned below being tested, the follow¬ ing sequence of effect was obtained (the most active compound being mentioned first) : 20, 1, 39, 42,13, 18, Permethrin, Fenvalerate. Example 46 Locusta migratoria igratorioides (R & F) (African migratory locust) . Solutions of the test compounds are prepared as mentioned in Example 45, but with a concentration of active compound of 0.25 micrograms per microlitre. 4th Stage unanaesthetized grasshopper nymphs are trea¬ ted with 4 microlitres of solution of test compound. 5 to 10 grasshoppers are treated with each compound, the grasshoppers having free access to fresh barley leaves and wheat-bran in the test period of 72 hours. The number of dead and moribund grasshoppers is counted at the end of the test period. Compound Insecticidal activity 1 A 2 A 20 A Compound Insecticidal activity 14 B 9 B 18 B 12 B 5 C 10 C Permethrin C Fenvalerate C 22 A 23 A 28 A 29 B 30 B 31 B 39 B 40 B 42 B 44 B Example 47 Sitophilus granarius (L.) (European granary weevil) . The test is carried out as mentioned in Example 45, only that 1 microlitre of solution containing 0.1 microgram of test compound is used per insect. The insects are fed with whole grains of wheat. Test period 96 hours. (Similar activities were obtained against Sitophilus oryzae) . Compound Insectic 18 A 20 A 14 B Permethrin B 22 A 23 A 26 A 28 A OMPI Compound Insecticidal activity 31 B 39 B 40 B Example 48 Dysdercus cingulatus (F.) (Cotton stainer ). The test is carried out as the other tests, using the same dose of compound as mentioned in Example 47, 10 5th stage nymphs per test compound and a period of observation of 72 hours. The animals have free access to water and cotton seed during the tests. Compound Insecticidal activity 4 A 20 A 9 A 18 A 1 B 5 B Permethrin B 12 B 23 A 27 A 40 A 41 B Example 49 Plutella xylostella (L.) (Diamond-backed moth) . The test compounds are dissolved in a Triton X-155 (1000 ppm) acetone solution. This formulation is diluted in water (1:9) to give a mixture of 10% acetone and 100 ppm Triton X-155 in water. The concentration of the test compound is 1 ppm. Discs (diameter of about 35 mm) of leaves of Chinese cabbage are dipped in these solutions. After drying 10 3rd stage larvae of diamond-backed moth are OMPI put oii, and after 48 hours the number of dead and mori¬ bund larvae and the condition of the discs of cabbage- leaves are assessed. Compound Insecticidal activity 1 A 2 A 13 A 18 A 4 B 'ermethrin B 22 A 23 A 25 A 26 A 27 A 28 A 29 B 30 B 41 B 44 A Example 50 Tetranychus urticae Koch (Spider mite) . Foiπnulations of test compounds are prepared (as mentioned in Example 49) and diluted in water to a concentration of test compound of 0.1%. Leaves of bean plants are dipped in these solutions.24 to 48 hours before being dipped these plants are infested with spinning mites at several stages of development. The bean plants are observed for 7 to 10 days, whereupon the effect in terms of mite killing and plant protection is assessed. Compound Insecticidal activity Permethrin C 1 B 2 B 4 B OMPI Compound Insecticidal activity 14 B Example 51 Heliothis zea (Boddie) , (Corn earworm) . The tests are carried out as mentioned in Example 49, except that leaves of maize are used instead of discs of cabbage-leaves. The concentration of test compound is 5 ppm. Compound Insecticidal activity Fenvalerate B 2 A 4 B 20 B 1 B 13 B 18 B 22 A 23 A 26 A 27 A 28 A Permethrin A Example 52 Experiments carried out as mentioned in Examples 45, 47 and 49, respectively, wherein insects (house flies, granary weevils and diamond-backed moths) are treated with test compounds belonging to the present group of compounds admixed with or after pretreatment with synergists, have demonstrated up to tenfold increase in effect. The following synergists have been used in the test: Piperonyl butoxide (51-03-6) , GK 264 (113-48-4) and octachlorodipropyl ether. Example 53 Drosophila melanogaster Meig (Fruit fly) . A drop or a few crystals are placed at the bottom of a test tube of a height of 10 cm and a diameter of 15 mm. The tube is provided with a web about 3 cm above the bottom. The tube is covered with Parafilm (trade mark) and placed at 27°C for 48 hours. Hereafter 10 fruit flies are added and the tube is covered again with Parafilm and placed at 27 C for 6 hours. Hereafter the flies are transferred to tubes containing standard nutrient medium. The number of dead and moribund flies is counted after 24 hours. Compound Insecticidal activitv 13 A 14 A Permethrin C Fenvalerate C Example 54 Orvzaephilus surinamensis (L . ) (Saw-toothed σrain beet¬ le) . Filter paper discs (about 4 cm in diameter) are impregnated with acetone solutions of the test com- pounds, 0.003 mg/cm 2. After evaporation of the solvent the filter paper discs are placed in Petri dishes which are pro¬ vided with 3 to 4 oatmeal flakes. 10 Adult grain beetles are let out in the dishes and placed at 27 C. After 72 hours the number of dead and moribund beetles is counted. Compound Insecticidal activity 20 A 9 B Permethrin B 23 A 27 OMPI Example 55 Toxicity to fish. Hitherto known pyrethroids, to which the com- 5 • pounds of the present invention are comparable to some extent, generally have a high toxicity to fish. The following example demonstrates that the compounds of the invention have a clearly lower toxicity to guppies than the known pyrethroid fenvalerate. •- - Poecilia reticulata Peters (Guppy) . Alcoholic solutions containing various concen¬ trations of each compound are prepared. The test solu¬ tions are mixed with tap water (100 ml) , wherein 3 fishes are let out per concentration of test compound. 15 From the observed dose-effect relation Cj- (the con¬ centration at which 50% of the fishes die within 24 hours) is calculated. The Table shows the toxicity index of the tested compounds calculated from the fol¬ lowing equation: 0 Toxicity index = LC 50 of fenvalerate x 100 LC 50 of test compound Compound Toxicitv index Fenvalerate 100 4 8 5 20 8 8 20 9 20 11 20 12 20 0 13 20 2 50 22 33 24 15 26 20 5 29 20 31 15 39 20 C CQ of fenvaleratehas been determined to be 0.3 ppm. Example 56 Blattella germanica (L.) (German cockroach) . The test is carried out using adult insects and as described in Example 47. During the test period the cockroaches have access to water and oatmeal feed. Compound Insecticidal activity Permethrin C 1 B 4 A 20 A Fenvalerate B Example 57 Phaedon cochleariae F. (Mustard beetle) . The test compounds are dissolved in acetone and applied to adult beetles in a dose of 2 nanograms per beetle. 10-20 Beetles are used per test and the observation period is 24 hours, whereupon the number of dead and moribund beetles is counted. Compound Insecticidal activity Fenvalerate A 1 B 22 B 23 B 27 A 28 B Example 58 Spodoptera littoralis (Boisd.) (Cotton leafworm) . The test compounds are dissolved in acetone and applied to 2nd stage larvae in a dose of 5 nanograms per larva. 10-20 Larvae are used per test and the observation period is 24 hours, whereupon the number of dead and moribund larvae is counted. Compound Insecticidal activity Fenvalerate B 1 C 2 B 4 C 20 B 22 B 23 B 27 A 28 A 29 B Example 59 Spodoptera exigua (Hb.) (Lesser armyworm) . The test compounds are dissolved in acetone and applied to 3rd stage larvae in a dose of 15 nanogram per larva. 10-20 Larvae are used per test and the observation period is 24 hours, whereupon the number of dead and moribund larvae is counted. Compound Insecticidal activity Fenvalerate B 2 A 4 B 1 B 20 A 22 A 23 A 26 C 27 A 28 A 29 A Example 60 Heliothis virescens Fab. (Tobacco budworm) . The test compounds are dissolved in acetone and applied to 3rd stage larvae in a dose of 15 nanograms per larva. 10-20 Larvae are used per test and the observation period is 24 hours, vαereupon the number of dead and moribund larvae is counted. Compound Insecticidal activity Permethrin A 4 B 23 A 27 B 28 A Example 61 Manduca sexta (Joh.) (Tobacco hornworm) . The test compounds are dissolved in acetone and applied to 3rd stage larvae in a dose of 15 nanograms per larva. 10-20 Larvae are used per test and the observation period is 24 hours, whereupon the number of dead and moribund larvae is counted. Comp -ound Insecticidal activit~y Permethrin B 1 A 2 A 4 B 14 C 20 B 22 A 23 A 26 B 27 A 28 A Example 62 Manduca sexta (Joh.) (Tobacco hornworm). The test compounds are dissolved in acetone and admixed to the nutrient medium of the larvae in a con¬ centration of 0.3 ppm. 10-20 3rd stage larvae are used per test and the observation period is 24 hours, whereupon the number of dead and moribund larvae is counted. Compound Insecticidal activity Cypermethrin B 1 B 2 C 4 B 20 B 22 A 23 B 26 C 27 B 28 A 29 C

Claims: P A T E N T C L A I M S 1. Arylcycloalkyl ether derivatives, characterized by having the general formula I wherein R represents a group of one of the following formulae A to M ti o K R, represents a hydrogen or halogen atom, a straight or branched chain alkyl group of 1 to 6 carbon atoms, a straight or branched chain alkoxy group of 1 to 6 carbon atoms or a haloalkyl group of 1 to 6 carbon atoms, R~ represents a hydrogen or halogen atom, an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to •6 carbon atoms or a haloalkyl group of 1 to 6 carbon atoms, or R-, and R 2 together form a methylenedioxy group, R-, represents a hydrogen or halogen atom or an alkyl group of 1 to 6 carbon atoms, X and Y each independently represents a hydrogen or halogen atom, m is an integer of from 1 to 5, and n is an integer of from 0 to 3. 2. Arylcycloalkyl ether derivatives according to claim 1, characterized in that R represents a group of one of the formulae A, B, C or K as stated in claim 1, R, represents a hydrogen atom, R 2 represents a halogen atom oran ethoxy, difluoro- methoxy, methoxy, methyl, ethyl or isopropyl group, or R, and R- together form a methylenedioxy group, R, represents a hydrogen atom, m is 1 or 3, and n is 0 or 1. OMPI ' 3. A pesticidal composition, particularly an insec¬ ticide, acaricide or tickicide, characterized by con¬ taining as an active component an arylcycloalkyl ether derivative according to claim 1 or 2. 4. A method for combating pests, particularly insects, acarids or ticks, characterized by applying to a locus attacked by or liable to be attacked by the pest concerned, an arylcycloalkyl ether derivative according to claim 1 or 2 or a preparation containing at least one such derivative. 5. use of arylcycloalkyl ether derivatives accor¬ ding to claim 1 or 2 for combating pests, particularly insects, acarids or ticks. 6. A process of preparing arylcycloalkyl ether derivatives of the general formula I as stated in claim 1, characterized by reacting a compound of the general formula I, wherein R represents a hydrogen atom, and R, , R_, R,, X, Y, m and n are as defined in claim 1, with a chloride of the formula R-Cl, wherein R is as defined in claim 1, in the presence of a base and a catalyst.

Inventors: JACOBSEN NIELS, KLEMMENSEN PER DAUSELL, PEDERSEN LARS-ERIK KRUSE, SVENDSEN AXEL KRISTIAN, JACOBSEN, NIELS, KLEMMENSEN, PER, DAUSELL, PEDERSEN, LARS-ERIK, KRUSE, SVENDSEN, AXEL, KRISTIAN
Applicants: CHEMINOVA AS, A/S CHEMINOVA
Application year: 1984
Main classification: C07C43
IPC codes: A01N31, A01N43, C07C43, C07D317, C07D407