Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
  • C07D295/26—Sulfur atoms
• • 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Definitions

• the present invention relates to new aryl-N-alkyl-carbamates, a process for their preparation and their use as insecticides.
• N-methylphenyl carbamates e.g. 2-sec-butylphenyl- or 2-iso-propoxyphenyl-N-methylcarbamate
• insecticidal properties see US Pat. No. 3,111,539, German Auslegeschrift 1,159,929 and 1,166,180.
• Hal represents halogen, preferably chlorine, if appropriate in the presence of an acid acceptor and a solvent.
• the aryl-N-alkyl-carbamates according to the invention have a better insecticidal action than the carbamates of analogous constitution and the same direction of action known from the literature.
• the fabrics according to the present invention thus represent a real enrichment of technology.
• the process for the preparation of the compounds according to the invention is preferably carried out using suitable solvents or diluents.
• suitable solvents or diluents Practically all inert organic solvents can be considered as such. These include in particular aliphatic and aromatic, given if chlorinated hydrocarbons, such as benzene, toluene, xylene, gasoline, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene or ether, for example diethyl and dibutyl ether, dioxane, and also ketones, for example acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, also nitriles, such as aceto- and propionitrile or pyridine.
• chlorinated hydrocarbons such as benzene, toluene, xylene, gasoline, methylene chloride, chloroform, carbon tetrachloride, chlor
• All customary acid binders can be used as acid acceptors.
• Alkali carbonates and alcoholates such as sodium and potassium carbonate, sodium and potassium methylate or ethylate, and also aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine and pyridine, have proven particularly useful.
• the reaction temperature can be varied within a wide range. In general, one works between 0 and 8 0 ° C, preferably at lo to 35 ° C.
• the reaction is generally allowed to proceed at normal pressure.
• the starting components are usually used in an equivalent ratio.
• An excess of one or the other reaction component has no significant advantages.
• the reaction components are usually combined in one of the solvents listed above and are usually stirred for several hours at room temperature to complete the reaction.
• the reaction mixture is then poured onto an ice / acid mixture and the oil which separates out is taken up in an organic solvent, e.g. Toluene.
• the organic phase is worked up by washing, drying and distilling off the solvent.
• the new compounds are obtained in the form of oils, some of which cannot be distilled without decomposing, but by so-called “distillation", i.e. can be freed from the last volatile constituents by prolonged heating under reduced pressure to moderately elevated temperatures and can be cleaned in this way.
• the refractive index is used to characterize them.
• the active ingredients are suitable for controlling animal pests, especially insects, that occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• the pests mentioned above include:
• the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, seed powders, active ingredient-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc. as well as ULV cold and warm fog formulations.
• customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, seed powders, active ingredient-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc. as well as
• formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, ie liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
• extenders ie liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• organic solvents can, for example, also be used as auxiliary solvents.
• liquid solvents aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water;
• Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers: natural rock flours, such as kaolins,
• Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
• the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
• the active compounds according to the invention are used in the form of their commercially available formulations and / or the use forms prepared from these formulations.
• the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
• the active substance concentration of the use forms can be from 0.0000001 to 100% by weight of active substance, preferably between 0.01 and 10% by weight.
• the application takes place in a customary manner adapted to the application forms.
• the active ingredients When used against hygiene pests and pests of stored products, the active ingredients are distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
• Cabbage plants (Brassica oleracea), which are heavily infested with peach aphids (Myzus persicae), are sprayed to runoff point with the preparation of active compound.
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
• the active ingredient preparation is intimately mixed with the soil.
• the treated soil is filled into pots and planted with cabbage (Brassica oleracea).
• the active ingredient can be taken up from the soil by the plant roots and transported to the leaves.
• a solution of 113 g (0.5 mol) of 2-ethylthiomethylphenyl-N-methyl-carbamate in 300 ml of pyridine is mixed with 57 g (0.5 mol) of dimethylaminosulfenyl chloride at room temperature and with exclusion of moisture and stirred at room temperature for 18 hours.
• the reaction mixture is poured onto a mixture of ice and 360 ml of pure, concentrated hydrochloric acid and the oil which has precipitated is taken up in toluene.
• the organic phase is washed with water, then with a bicarbonate solution and dried over sodium sulfate.

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• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Plant Pathology (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (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)
• Pyridine Compounds (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

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Family Applications (1)

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Cited By (1)

Citations (5)

• 1977
  • 1977-08-20 DE DE19772737606 patent/DE2737606A1/de active Pending
• 1978
  • 1978-08-07 EP EP78100609A patent/EP0000895A1/de not_active Withdrawn
  • 1978-08-17 IL IL7855381A patent/IL55381A0/xx unknown
  • 1978-08-18 ZA ZA00784699A patent/ZA784699B/xx unknown
  • 1978-08-18 AU AU39060/78A patent/AU3906078A/en active Pending
  • 1978-08-18 DK DK367778A patent/DK367778A/da unknown
  • 1978-08-18 IT IT7826848A patent/IT7826848A0/it unknown
  • 1978-08-18 ES ES472669A patent/ES472669A1/es not_active Expired
  • 1978-08-18 JP JP10012078A patent/JPS5441842A/ja active Pending
  • 1978-08-19 PL PL20913278A patent/PL209132A1/xx unknown

Patent Citations (5)

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