Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
  • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
  • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
  • A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
  • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
  • A01N31/14—Ethers
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
  • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
  • A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
  • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
  • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
  • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
  • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
  • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/14—Unsaturated ethers
  • C07C43/164—Unsaturated ethers containing six-membered aromatic rings
  • C07C43/168—Unsaturated ethers containing six-membered aromatic rings containing six-membered aromatic rings and other rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/14—Unsaturated ethers
  • C07C43/17—Unsaturated ethers containing halogen
  • C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
  • C07C43/1747—Unsaturated ethers containing halogen containing six-membered aromatic rings containing six membered aromatic rings and other rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
  • C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
  • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
  • C07C43/267—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing other rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
  • C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
  • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
  • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
  • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
  • C07D317/54—Radicals substituted by oxygen atoms

Definitions

• Arylcycloalkyl ether derivatives their use and preparation.
• the present invention relates to novel arylcycloalkyl 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.
• R represents a group of one of the following formulae A to M
• R 1 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 2 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 1 , 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
• ' m is an integer of from 1 to 5
• 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.
• R represents a group of one of the formulae A, B, C or K as stated above,
• R 1 represents a hydrogen atom
• R 2 represents a halogen atom or an ethoxy, difluoromethoxy, methoxy, methyl, ethyl or isopropyl group, or
• R 1 and R 2 together form a methylenedioxy group
• R 3 represents a hydrogen atom, m is 1 or 3, and n is 0 or 1.
• the invention also relates to a pesticidal composition, particularly an insecticide, acaricide or tickicide, which is characterized by containing as an active component an arylcycloalkyl ether derivative according to the invention.
• 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 arylcycloalkyl 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 1 , R 2 , R 3 , X, Y, m og n are as defined above, is reacted with a chloride of the formula R-C1, wherein R is as defined above, in the presence of a base and a catalyst and in the presence or absence of a solvent.
• a pesticidal composition can be prepared 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.
• carrier 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.
• compositions of the invention may be formulated as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates 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 concentrate 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 component.
• 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.
• 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 thixotropic agents, 0-10% by weight of appropriate additives such as defoamers, 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.
• compositions may also contain other ingredients, for example, other compounds having pesticidal, particularly acaricidal, herbicidal or fungicidal properties.
• the compounds of the invention possess pesticidal and especially insecticidal properties, which are superior to the properties of some of the known commonly used pyrethroids , e.g., permethrin (52645-53-1) (3-phenoxybenzyl-2,2-dimethyl-3-(2,2-dichlorovinyl)- cyclopropane carboxylate) and fenvalerate (51630-58-1) ( ⁇ -cyano-3-phenoxybenzyl-2-(4-chlorophenyl)-3-methyl butyrate and allethrin (584-79-2) and cismethrin (10453-86-8).
• permethrin (52645-53-1) (3-phenoxybenzyl-2,2-dimethyl-3-(2,2-dichlorovinyl)- cyclopropane carboxylate) and
• the compounds of the invention exhibit a selective or non-selective activity on organisms of various orders such as Coleoptera, Lepidoptera, Diptera, Orthoptera,
• 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 activities 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.
• Acetone solutions or formulations of the compounds to be tested are prepared in a concentration of 0.025 micrograms per microlitre.
• 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 number of dead and moribund flies is counted at the end of the test period.
• Example 46 Locusta migratoria migratorioides (R & F) (African migratory locust).
• Test compounds 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 treated 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.
• 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).
• 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.
• Example 49 Plutella xylostella (L.) (Diamond-backed moth).
• 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 put on, and after 48 hours the number of dead and moribund larvae and the condition of the discs of cabbageleaves are assessed.
• Formulations 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.
• Example 51 Heliothis zea (Boddie), (Corn earworm).
• test compound Insecticidal activity
• 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.
• 10 fruit flies are added and the tube is covered again with Parafilm and placed at 27oC for 6 hours.
• the flies are transferred to tubes containing standard nutrient medium. The number of dead and moribund flies is counted after 24 hours.
• Example 54 Orvzaephilus surinamensis (L . ) (Saw-toothed ⁇ rain beetle) .
• Filter paper discs (about 4 cm in diameter) are impregnated with acetone solutions of the test compounds, 0.003 mg/cm 2. After evaporation of the solvent the filter paper discs are placed in Petri dishes which are provided with 3 to 4 oatmeal flakes. 10 Adult grain beetles are let out in the dishes and placed at 27oC. After 72 hours the number of dead and moribund beetles is counted.
• the following example demonstrates that the compounds of the invention have a clearly lower toxicity to guppies than the known pyrethroid fenvalerate.
• Alcoholic solutions containing various concentrations of each compound are prepared.
• the test solutions are mixed with tap water (100 ml), wherein 3 fishes are let out per concentration of test compound.
• LC 5 0 the concentration at which 50% of the fishes die within 24 hours.
• the Table shows the toxicity index of the tested compounds calculated from the following equation:
• 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.
• 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 is 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.
• 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, v ⁇ ereupon the number of dead and moribund larvae is counted.
• 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.
• Manduca sexta (Joh.) (Tobacco hornworm).
• the test compounds are dissolved in acetone and admixed to the nutrient medium of the larvae in a concentration 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.

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• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Dentistry (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Plant Pathology (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (10)

• 1983
  • 1983-04-25 DK DK181683A patent/DK181683A/da not_active Application Discontinuation
• 1984
  • 1984-04-18 IL IL71572A patent/IL71572A0/xx unknown
  • 1984-04-24 ZA ZA843029A patent/ZA843029B/xx unknown
  • 1984-04-25 WO PCT/DK1984/000034 patent/WO1984004298A1/en unknown
  • 1984-04-25 EP EP84901748A patent/EP0143806A1/en not_active Withdrawn

Patent Citations (10)

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