EP0000895A1 - Aryl-N-alkylcarbamates, method for their preparation and their use as insecticides - Google Patents

Aryl-N-alkylcarbamates, method for their preparation and their use as insecticides Download PDF

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Publication number
EP0000895A1
EP0000895A1 EP78100609A EP78100609A EP0000895A1 EP 0000895 A1 EP0000895 A1 EP 0000895A1 EP 78100609 A EP78100609 A EP 78100609A EP 78100609 A EP78100609 A EP 78100609A EP 0000895 A1 EP0000895 A1 EP 0000895A1
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Prior art keywords
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aryl
formula
alkyl
carbamates
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German (de)
French (fr)
Inventor
Hellmut Prof. Dr. Hoffmann
Ingeborg Dr. Hammann
Bernhard Dr. Homeyer
Wilhelm Dr. Stendel
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Bayer AG
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Bayer AG
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    • 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)

Abstract

Aryl N-alkylcarbamates of the formula <IMAGE> are synthesised in which R and R<1> represent identical or different alkyl and R<2> represents dialkylamino or a nitrogen-containing heterocycle in which the heterocycle can additionally contain further heteroatoms. These compounds are distinguished by strong insecticidal properties. They are obtained when aryl N-alkylcarbamates of the formula <IMAGE> in which R and R<1> have the abovementioned meaning, are reacted with sulphenyl halides of the formula R<2>-S-Hal, if appropriate in the presence of an acid acceptor and of a solvent.

Description

Die vorliegende Erfindung betrifft neue Aryl-N-alkyl-carbamate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide.The present invention relates to new aryl-N-alkyl-carbamates, a process for their preparation and their use as insecticides.

Es ist bereits bekannt, daß N-Methyl-phenylcarbamate, z.B. 2-sek.-Butylphenyl- bzw. 2-iso-Propoxyphenyl-N-methylcarbamat, insektizide Eigenschaften aufweisen (vergleiche US-Patent 3 111 539, Deutsche Auslegeschriften 1 159 929 und 1 166 180).It is already known that N-methylphenyl carbamates, e.g. 2-sec-butylphenyl- or 2-iso-propoxyphenyl-N-methylcarbamate, have insecticidal properties (see US Pat. No. 3,111,539, German Auslegeschrift 1,159,929 and 1,166,180).

Es wurden nun die neuen Aryl-N-alkyl-carbamate der Formel

Figure imgb0001
synthetisiert, worin

  • R und R1 für gleiches oder verschiedenes Alkyl und
  • R 2 für Dialkylamino oder einen stickstoffhaltigen Heterocyclus stehen, wobei der Heterocyclus noch weitere Heteroatome enthalten kann.
There have now been the new aryl-N-alkyl-carbamates of the formula
Figure imgb0001
 synthesized in which
  • R and R 1 for the same or different alkyl and
  • R 2 is D ialkylamino or a nitrogen-containing heterocycle, where the heterocycle may contain additional heteroatoms.

Diese neuen Verbindungen zeichnen sich durch starke insektizide Eigenschaften aus.These new compounds are characterized by strong insecticidal properties.

Weiterhin wurde gefunden, daß die Aryl-N-alkyl-carbamate der Formel (I) erhalten werden, wenn man Aryl-N-alkyl- carbamate der Formel (II)

Figure imgb0002
in welcher

  • R und R1 die oben angegebene Bedeutung haben,

mit Sulfenylhalogeniden der Formel (III)
Figure imgb0003
in welcher
  • R2 die oben angegebene Bedeutung hat und
It has furthermore been found that the aryl-N-alkyl-carbamates of the formula (I) are obtained if aryl-N-alkyl-carbamates of the formula (II)
Figure imgb0002
 in which
  • R and R 1 have the meaning given above,

with sulfenyl halides of the formula (III)
Figure imgb0003
 in which
  • R 2 has the meaning given above and

Hal für Halogen, vorzugsweise Chlor, steht,
gegebenenfalls in Gegenwart eines Säureakzeptors und eines Lösungsmittels umsetzt.Hal represents halogen, preferably chlorine,
if appropriate in the presence of an acid acceptor and a solvent.

Überraschenderweise besitzen die erfindungsgemäßen Aryl-N-alkyl-carbamate eine bessere insektizide Wirkung als die aus der Literatur vorbekannten Carbamate analoger Konstitution und gleicher Wirkungsrichtung. Die Stoffe gemäß vorliegender Erfindung stellen somit eine echte Bereicherung der Technik dar.Surprisingly, 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.

Verwendet man beispielsweise 2-n-Propylthiomethyl-phenyl-N-n-propyl-carbamat und Diäthylaminosulfenylchlorid als Ausgangsstoffe, so kann der Reaktionsverlauf durch das folgende Formelschema wiedergegeben werden:

Figure imgb0004
If, for example, 2-n-propylthiomethyl-phenyl-Nn-propyl-carbamate and diethylaminosulfenyl chloride are used as starting materials, the course of the reaction can be represented by the following formula:
Figure imgb0004

Die zu verwendenden Ausgangsstoffe sind durch die Formeln (II) und (III) allgemein definiert. Vorzugsweise stehen darin jedoch

  • R und R1 für gleiches oder verschiedenes, geradkettiges oder verzweigtes Alkyl mit 1 bis 6, vorzugsweise 1 bis 4, Kohlenstoffatomen und
  • R 2 für Dialkylamino mit 1 bis 4, vorzugsweise 1 bis 3, Kohlenstoffatomen je Alkylrest, für einen 5 bis 7 gliedrigen, vorzugsweise 5 oder 6 gliedrigen, gesättigten Stickstoffheterocyclus, der gegebenenfalls durch Sauerstoff, Schwefel oder einem weiteren Stickstoffatomen, bevorzugt durch Sauerstoff, unterbrochen sein kann.
The starting materials to be used are generally defined by the formulas (II) and (III). Preferably, however, are in it
  • R and R 1 are the same or different, straight-chain or branched alkyl having 1 to 6, preferably 1 to 4, carbon atoms and
  • R 2 for dialkylamino with 1 to 4, preferably 1 to 3, carbon atoms per alkyl radical, for a 5 to 7-membered, preferably 5 or 6-membered, saturated nitrogen heterocycle which is optionally interrupted by oxygen, sulfur or another nitrogen atom, preferably by oxygen can be.

Die als Ausgangsstoffe zu verwendenden Aryl-N-alkyl-carbamate (II) sind bekannt oder können nach bekannten Verfahren leicht hergestellt werden (vergleiche Deutsche Auslegeschrift 1 254 617 und Belgische Patentschrift 746 649). Als Beispiele dafür seien im einzelnen genannt:

  • 2-Methylthiomethyl-phenyl, 2-Äthylthiomethyl-phenyl-, 2-n-Propylthiomethyl-phenyl- und 2-iso-Propylthiomethyl-phenyl-, 2-n-Butylthiomethyl-phenyl-, 2-iso-Butylthiomethyl-phenyl-und 2-sek.-Butylthiomethyl-phenyl-N-methyl- bzw. -N-äthyl-, -N-n-propyl-, -N-iso-propyl-, -N-n-butyl-, -N-iso-butyl- und -N-sek.-butyl-carbamat.
The aryl-N-alkyl-carbamates (II) to be used as starting materials are known or can easily be prepared by known processes (see German Ausleschrift 1,254,617 and Belgian Patent 746,649). The following are examples of this:
  • 2-methylthiomethylphenyl, 2-ethylthiomethylphenyl, 2-n-propylthiomethylphenyl and 2-iso-propylthiomethylphenyl, 2-n-butylthiomethylphenyl, 2-iso-butylthiomethylphenyl and 2 -sec.-Butylthiomethyl-phenyl-N-methyl- or -N-ethyl-, -Nn-propyl-, -N-iso-propyl-, -Nn-butyl-, -N-iso-butyl- and -N sec-butyl carbamate.

Die weiterhin als Ausgangsstcffe zu verwendenden Sulfenylhalogenide (III) sind ebenfalls bekannt oder nach bekannten Verfahren herstellbar (vergleiche Belgische Patentschriften 817 515 und 817 517). Als Beispiele dafür seien im einzelnen genannt:

  • Dimethylamino-, Diäthylamino-, Di-n-propylamino-, Di-isopropylamino-, Pyrrolidinyl(1), Piperidyl (1) und Morpholinyl(4)-sulfenylchlorid.
The sulfenyl halides (III) which are also to be used as starting materials are also known or can be prepared by known processes (see Belgian patents 817 515 and 817 517). The following are examples of this:
  • Dimethylamino, diethylamino, di-n-propylamino, di-isopropylamino, pyrrolidinyl (1), piperidyl (1) and morpholinyl (4) sulfenyl chloride.

Das Verfahren zur Herstellung der erfindungsgemäßen Verbindungen wird bevorzugt unter Mitverwendung geeigneter Lösungs-oder Verdünnungsmittel durchgeführt. Als solche kommen praktisch alle inerten organischen Solventien infrage. Hierzu gehören insbesondere aliphatische und aromatische, gegebenenfalls chlorierte Kohlenwasserstoffe, wie Benzol, Toluol, Xylol, Benzin, Methylenchlorid, Chloroform, Tetrachlorkohlenstoff, Chlorbenzol, oder Äther, z.B. Diäthyl- und Dibutyl- äther, Dioxan, ferner Ketone, beispielsweise Aceton, Methyl- äthyl-, Methylisopropyl- und Methylisobutylketon, außerdem Nitrile, wie Aceto- und Propionitril oder Pyridin.The process for the preparation of the compounds according to the invention is preferably carried out using 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.

Als Säureakzeptoren können alle üblichen Säurebindemittel Verwendung finden. Besonders bewährt haben sich Alkalicarbonate und -alkoholate, wie Natrium- und Kaliumcarbonat, Natrium- und Kaliummethylat bzw. -äthylat, ferner aliphatische, aromatische oder heterocyclische Amine, beispielsweise Triäthylamin, Trimethylamin, Dimethylanilin, Dimethylbenzylamin und Pyridin.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.

Die Reaktionstemperatur kann innerhalb eines größeren Bereichs variiert werden. Im allgemeinen arbeitet man zwischen 0 und 80°C, vorzugsweise bei lo bis 35°C.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.

Die Umsetzung läßt man im allgemeinen bei Normaldruck ablaufen.The reaction is generally allowed to proceed at normal pressure.

Zur Durchführung des Verfahrens setzt man die Ausgangskomponenten meist in äquivalentem Verhältnis ein. Ein Überschuß der einen oder anderen Reaktionskomponente bringt keine wesentlichen Vorteile. Die Reaktionskomponenten werden meist in einem der oben angeführten Lösungsmittel zusammengegeben und meist bei Raumtemperatur zur Vervollständigung der Reaktion mehrere Stunden gerührt. Danach gibt man die Reaktionsmischung auf ein Gemisch aus Eis/Säure und nimmt das sich ausscheidende Öl in einem organischen Lösungsmittel, z.B. Toluol, auf. Die organische Phase wird wie üblich durch Waschen, Trocknen und Abdestillieren des Lösungsmittels aufgearbeitet.To carry out the process, 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. As usual, the organic phase is worked up by washing, drying and distilling off the solvent.

Die neuen Verbindungen fallen in Form von ölen an, die sich zum Teil nicht unzersetzt destillieren lassen, jedoch durch sogenanntes "Andestillieren", d.h. durch längeres Erhitzen unter vermindertem Druck auf mäßig erhöhte Temperaturen von den letzten flüchtigen Anteilen befreit und auf diese Weise gereinigt werden. Zu ihrer Charakterisierung dient der Brechungsindex.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.

Die Wirkstoffe eignen sich bei guter Pflanzenverträglichkeit und günstiger Warmblütertoxizität zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten,
die in der Landwirtschaft, in Forsten, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören:With good plant tolerance and favorable warm-blooded toxicity, 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:

Aus der Ordnung der Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

  • Aus der Ordnung der Diplopoda z. B. Blaniulus guttulatus.
  • Aus der Ordnung der Chilopoda z. B. Geophilus carpophagus, Scutigera spee.
  • Aus der Ordnung der Symphyla z. Be Scutigerella immaculata.
  • Aus der Ordnung der Thysanura z. B. Lepisma saccharina.
  • Aus der Ordnung der Collembola z. B. Onychiurus armatus.
  • Aus der ordnung der Orthoptera z. B. Blatta orientalis, Periplaneta aaericana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
  • Aus der Ordnung der Dermaptera z. B. Forficula auricularia.
  • Aus der Ordnung der Isoptera z. B. Reticulitermes spp..
  • Aus der Ordnung der Anoplura z. B. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
  • Aus der Ordnung der Mallophaga z.B. Trichodectes spp., Damalinea spp.
  • Aus der Ordnung der Thysanoptera z.B. Hercinothrips femoralis, Thrips tabaci.
  • Aus der Ordnung der Heteroptera z.B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
  • Aus der Ordnung der Homoptera z.B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Erio soma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp..
  • Aus der Ordnung der Lepidoptera z. B. 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, Carpocapaa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana. Aus der Ordnung der Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidiua 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 auleatus, Cosmopolites sordidus, Ceuthorrhynchus assinilis, Hypera postica, Dermestes spp., Trogoderma app., Anthrenus app., Attagenus spp., Lyctus app., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
  • Aus der Ordnung der Hymenoptera z. B. Diprion app., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. Aus der Ordnung der Diptera z.B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami,Ceratitts capitata, Dacus oleae, Tipula paludosa.
  • Aus der Ordnung der Siphonaptera z.B. Xenopsylla cheopis, Ceratophyllus spp..
From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • From the order of the Diplopoda z. B. Blaniulus guttulatus.
  • From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spee.
  • From the order of the Symphyla z. B e Scutigerella immaculata.
  • From the order of the Thysanura z. B. Lepisma saccharina.
  • From the order of the Collembola z. B. Onychiurus armatus.
  • From the order of Orthoptera z. B. Blatta orientalis, Periplaneta aaericana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
  • From the order of the Dermaptera z. B. Auricular Forficula.
  • From the order of the Isoptera z. B. Reticulitermes spp ..
  • From the order of the Anoplura z. B. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
  • From the order of the M allophaga, 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, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Erio soma lanigerum, Hyalopterus arundinis, Macrosiphum humenae, Phyopodosum, Phyophorosumi, Myzus sononum, Myzus sononum. Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp ..
  • From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisppella, Phyllella. Phyllella , Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapaa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Caulacoecelliaella, Galleria mellella Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana. From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidiua 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 auleatus, Cosmopolites sordinh. Anthrenus app., Attagenus spp., Lyctus app., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimalltraon solealandas, Cost
  • From the order of the Hymenoptera z. B. Diprion app., 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., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca ., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitts capitata, Dacus oleae, Tipula paludosa.
  • From the order of the Siphonaptera, for example Xenopsylla cheopis, Ceratophyllus spp ..

Die Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Schäume, Pasten, lösliche Pulver, Granulate, Aerosole, Suspensions-Emulsionskonzentrate, Saatgutpuder, Wirkstoff-imprägnierte Natur- und synthetische Stoffe, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, ferner in Formulierungen mit Brennsätzen, wie Raucherpatronen, -dosen, -spiralen u.ä. sowie ULV-Kalt- und Warmnebel-Formulierungen.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.

Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen urd/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen infrage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chloräthylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, Alkohole, wie Butanol oder Glycol sowie deren Äther und Ester, Ketone, wie Aceton, Methyläthylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser; mit verflüssigten gasförmigen Streckmitteln oder Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol-Treibgase, wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid; als feste Trägerstoffe: natürliche Gesteinemehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate; als feste Trägerstoffe für Granulate: gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehle, Kokosnußschalen, Maiskolben und Tabakstengel; als Emulgier-und/oder schaumerzeugende Mittel: nichtionogene und anionische Emulgatoren, wie Polyoxyäthylen-Fettsäure-Ester, Polyoxyäthylen-Fettalkohol-Äther, z.B. Alkylaryl-polyglykol-äther, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel: z.B. Lignin-Sulfitablaugen und Methylcellulose.These 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. The following are essentially suitable as 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, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flours, such as highly disperse silica, aluminum oxide and silicates; as solid carriers for granules: broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifiers and / or foam-generating agents: nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxy ethylene-fatty alcohol ether, for example alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersing agents: eg lignin sulfite liquor and methyl cellulose.

Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat,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.

Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo-Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.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.

Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

Die Anwendung der erfindungsgemäßen Wirkstoffe erfolgt in Form ihrer handelsüblichen Formulierungen und/oder den aus diesen Formulierungen bereiteten Anwendungsformen.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.

Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren. Die Wirkstoffkonzentration der Anwendungsformen kann von 0,0000001 bis zu 100 Gew.-% Wirkstoff, vorzugsweise zwischen 0,01 und 10 Gew.-% liegen.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.

Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise.The application takes place in a customary manner adapted to the application forms.

Bei der Anwendung gegen Hygiene- und Vorratsschädlinge zeichnen sich die Wirkstoffe durch eine hervorragende Residualwirkung auf Holz und Ton sowie durch eine gute Alkalistabilität auf gekälkten Unterlagen aus.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.

Beispiel AExample A

Myzus-Test (Kontakt-Wirkung)

  • Lösungsmittel: 3 Gewichtsteile Dimethylformamid
  • Emulgator: 1 Gewichtsteil Alkylarylpolyglykoläther
Myzus test (contact effect)
  • Solvent: 3 parts by weight of dimethylformamide
  • Emulsifier: 1 part by weight of alkylaryl polyglycol ether

Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und der angegebenen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of 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.

Mit der Wirkstoffzubereitung werden Kohlpflanzen (Brassica oleracea), welche stark von der Pfirsichblattlaus (Myzus persicae) befallen sind, tropfnaß besprüht.Cabbage plants (Brassica oleracea), which are heavily infested with peach aphids (Myzus persicae), are sprayed to runoff point with the preparation of active compound.

Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele überlegene Wirkung gegenüber dem Stand der Technik, 1, 10, 6, 3, 12, 2, 8, 4, 7, 11, 5In this test, e.g. the following compounds of the preparation examples superior activity over the prior art, 1, 10, 6, 3, 12, 2, 8, 4, 7, 11, 5

Beispiel BExample B

Grenzkonzentrations-Test / Wurzelsystemische WirkungLimit concentration test / root systemic effect

Testinsekt: Myzus persicae

  • Lösungsmittel: 3 Gewichtsteile Aceton
  • Emulgator: 1 Gewichtsteil Alkylarylpolyglykoläther
Test insect: Myzus persicae
  • Solvent: 3 parts by weight of acetone
  • Emulsifier: 1 part by weight of alkylaryl polyglycol ether

Zur herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of 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.

Die Wirkstoff Zubereitung wird innig mit dem Boden vermischt. Dabei spielt die Konzentration des Wirkstoffs in der Zubereitung praktisch keine Rolle, entscheidend ist allein die Wirkstoffgewichtsmenge pro Volumeneinheit Boden, welche in ppm (= mg/1) angegeben wird. Man füllt den behandelten Boden in Töpfe und bepflanzt diese mit Kohl (Brassica oleracea). Der Wirkstoff kann so von den Pflanzenwurzeln aus dem Boden aufgenommen und in die Blätter transportiert werden.The active ingredient preparation is intimately mixed with the soil. The concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (= mg / 1). 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.

Für den Nachweis des wurzelsystemischen Effektes werden nach 7 Tagen ausschließlich die Blätter mit den obengenannten Testtieren besetzt. Nach weiteren 2 Tagen erfolgt die Auswertung durch Zählen oder Schätzen der toten Tiere.To prove the root systemic effect, only the leaves are populated with the test animals mentioned above after 7 days. After a further 2 days, the evaluation is carried out by counting or estimating the dead animals.

Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele überlegene Wirkung gegenüber dem Stand der Technik: 1, 2.In this test, e.g. the following compounds of the preparation examples have a superior action over the prior art: 1

Beispiel CExample C

Test mit parasitierenden Fliegenlarven

  • Testinsekt: Lucilia cuprina
  • Emulgator: 80 Gew.-Teile Alkylarylpolyglykoläther
Test with parasitic fly larvae
  • Test insect: Lucilia cuprina
  • Emulsifier: 80 parts by weight of alkylaryl polyglycol ether

Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 20 Gew.-Teile der betreffenden aktiven Substanz mit der angegebenen Menge des Emulgators und verdünnt das so erhaltene Gemisch mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 20 parts by weight of the active substance in question are mixed with the stated amount of the emulsifier and the mixture thus obtained is diluted with water to the desired concentration.

Etwa 20 Fliegenlarven (Lucilia cuprina) werden in ein mit Wattestopfen entsprechender Größe beschicktes Teströhrchen gebracht, welches ca. 3 ml einer 20 %igen Eigelbpulver-Suspension in Wasser enthält. Auf diese Eigelbpulver-Suspension werden 0,5 ml der Wirkstoffzubereitung gebracht. Nach 24 Stunden wird der Abtötungsgrad bestimmt.About 20 fly larvae (Lucilia cuprina) are placed in a test tube filled with cotton plugs of the appropriate size, which contains approx. 3 ml of a 20% egg yolk powder suspension in water. 0.5 ml of the active ingredient preparation is added to this egg yolk powder suspension. The degree of destruction is determined after 24 hours.

Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele überlegene Wirkung gegenüber dem Stand der Technik: 2, 3, 7, 8.In this test, e.g. the following compounds of the preparation examples superior activity over the prior art: 2, 3, 7, 8.

HerstellungsbeispieleManufacturing examples

Figure imgb0005
Figure imgb0005

Eine Lösung aus 113 g (o,5 Mol) 2-Äthylthiomethylphenyl-N-methyl-carbamat in 3oo ml Pyridin wird bei Raumtemperatur und unter Feuchtigkeitsausschluß mit 57 g (o,5lMol) Dimethylaminosulfenylchlorid versetzt und 18 Stunden bei Raumtemperatur gerührt. Das Reaktionsgemisch wird auf eine Mischung aus Eis und 360 ml reiner,konzentrierter Salzsäure gegossen und das ausgefallene Öl in Toluol aufgenommen. Die organische Phase wird mit Wasser, anschließend mit einer Bicarbonatlösung gewaschen und über Natriumsulfat getrocknet. Das Toluol wird im Vakuum am Rotationsverdampfer abgezogen und der verbleibende Rückstand im Hochvakuum bei einer Badtemperatur von 50-6°C andestilliert. Man erhält 9o g (60 % der Theorie) 2-Äthylthiomethyl-phenyl-N-dimethylaminosulfenyl-N-methyl-carbamat mit dem Brechungsindex n21.5 D :1,5605.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. The toluene is removed in a vacuum on a rotary evaporator and the remaining residue is distilled in a high vacuum at a bath temperature of 50-6 ° C. 90 g (60% of theory) of 2-ethylthiomethyl-phenyl-N-dimethylaminosulfenyl-N-methyl-carbamate with a refractive index n 21.5 D : 1.5605 are obtained.

Analog können die Verbindungen der Formel

Figure imgb0006
hergestellt werden:
Figure imgb0007
 The compounds of the formula
Figure imgb0006
 getting produced:
Figure imgb0007

Claims (6)

1. Aryl-N-alkyl-carbamate der Formel (I)
Figure imgb0008
worin Rund R1 für gleiches oder verschiedenes Alkyl steht und R 2 für Dialkylamino oder einen stickstoffhaltigen Heterocyclus steht, wobei der Heterocyclus noch weitere Heteroatome enthalten kann. 1. Aryl-N-alkyl-carbamates of the formula (I)
Figure imgb0008
 wherein R 1 represents the same or different alkyl and R 2 is D ialkylamino or a nitrogen-containing heterocycle, where the heterocycle may contain additional heteroatoms. 2. Verfahren zur Herstellung der Aryl-N-alkyl-carbamate der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, daß man Aryl-N-alkylcarbamate der Formel (II)
Figure imgb0009
in welcher Rund R1 die oben angegebene Bedeutung haben,
mit Sulfenylhalogeniden der Formel (III)
Figure imgb0010
in welcher R 2 die oben angegebene Bedeutung hat und Hal für Halogen, vorzugsweise Chlor, steht, gegebenenfalls in Gegenwart eines Säureakzeptors und eines Lösungsmittels umsetzt. 2. A process for the preparation of the aryl-N-alkyl-carbamates of the formula (I) according to claim 1, characterized in that aryl-N-alkyl carbamates of the formula (II)
Figure imgb0009
 in which R 1 have the meaning given above,
with sulfenyl halides of the formula (III)
Figure imgb0010
 in which R 2 has the meaning given above and Hal represents halogen, preferably chlorine, if appropriate in the presence of an acid acceptor and a solvent. 3. Insektizide Mittel gekennzeichnet durch einen Gehalt an Aryl-N-alkyl-carbamate der Formel (I) gemäß Anspruch 1.3. Insecticidal agents characterized by a content of aryl-N-alkyl-carbamate of the formula (I) according to claim 1. 4. Verwendung von Aryl-N-alkyl-carbamate der Formel (I) gemäß Anspruch 1 zur Bekämpfung von Insekten.4. Use of aryl-N-alkyl-carbamates of the formula (I) according to Claim 1 for combating insects. 5. Verfahren zur Bekämpfung von Insekten, dadurch gekennzeichnet, daß man Aryl-N-alkyl-carbamate der Formel (I) gemäß Anspruch 1 auf Insekten und/oder ihren Lebensraum einwirken läßt.5. A method of controlling insects, characterized in that aryl-N-alkyl-carbamates of the formula (I) according to Claim 1 are allowed to act on insects and / or their habitat. 6. Verfahren zur Herstellung insektizider Mittel, dadurch gekennzeichnet, daß man Aryl-N-alkyl-carbamate der Formel (I) gemäß Anspruch 1 mit Streckmitteln und oberflächenaktiven Stoffen vermischt.6. A process for the preparation of insecticidal agents, characterized in that aryl-N-alkyl-carbamates of the formula (I) according to Claim 1 are mixed with extenders and surface-active substances.
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DE2628574A1 (en) * 1975-06-26 1977-01-20 Union Carbide Corp NEW PESTICIDAL COMPOUNDS AND PROCEDURES FOR THEIR PRODUCTION
DE2632692A1 (en) * 1975-07-24 1977-02-10 Ciba Geigy Ag SCHAEDLING INHIBITOR
DE2655212A1 (en) * 1976-01-02 1977-07-14 Upjohn Co AMINOTHIOCARBAMATES, THE PROCESS FOR THEIR MANUFACTURING AND PESTICIDES CONTAINING THEM
DE2724764A1 (en) * 1976-06-04 1977-12-15 Ciba Geigy Ag N-SULFONYL-DIAMINOSULFIDES, METHOD FOR THE PREPARATION THEREOF AND AGENTS CONTAINING THE SAME
DE2727614A1 (en) * 1976-06-22 1978-01-05 Ciba Geigy Ag N, N'-BIS-CARBAMIC ACID-SULPHIDE DERIVATIVES, PROCESS FOR THEIR MANUFACTURING AND PEST-CONTROLLERS

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ES472669A1 (en) 1979-02-16
ZA784699B (en) 1979-08-29
AU3906078A (en) 1980-02-21
DE2737606A1 (en) 1979-03-01
IL55381A0 (en) 1978-10-31
IT7826848A0 (en) 1978-08-18
PL209132A1 (en) 1979-05-21
JPS5441842A (en) 1979-04-03
DK367778A (en) 1979-02-21

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