Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C271/06—Esters of carbamic acids
• • 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
  • A01N47/22—O-Aryl or S-Aryl esters thereof
• • G—PHYSICS
  • G06—COMPUTING OR CALCULATING; COUNTING
  • G06C—DIGITAL COMPUTERS IN WHICH ALL THE COMPUTATION IS EFFECTED MECHANICALLY
  • G06C29/00—Combinations of computing machines with other machines, e.g. with typewriter, with money-changing apparatus

Definitions

• the present invention relates to preparations for combating blood-sucking arthropodes which contain, as the active component, at least one compound ofgeneral formula as the free base or in the form of one of its salts, wherein R represents an alkyl residue containing not more than three carbon atoms and R, an alkyl residue containing two to four carbon atoms, together with a carrier.
• suitable carriers there may be mentioned solvents, diluents, dispersing agents, wetting agents, emulsifiers, thickeners as well as further known pesticides.
• the present invention also provides carbamates of the above formula (I) and their salts, on which the agents are based.
• the present invention also provides a process for preparing the carbamates of the above formula (I), which comprises reacting a phenol of formula with methylisocyanate or methylcarbamic acid chloride or by reacting an aminophenylcarbonate or aminophenylchlorocarbonate of formula X-CO-O with methylamine, in which formulae R and R have the meanings given above or represent substituents which can be converted into these quoted substituents by post-alkylation, X represents a halogen atom, preferably a chlorine atom.
• the phenols required as intermediate products can be manufactured by a method known per se. It is, for example, possible to alkylate o-aminophenol in the amino group by means of an alkyl sulphate or dialkyl sulphate, alkyl tosylate or alkyl halide, during which an acid-binding agent may be added.
• a further method consists in the reductive alkylation of o-nitrophenol or o-aminophenol with an aldehyde or ketone and catalytically activated hydrogen. lf R and R, are not identical, the alkylation reactions have to be carried out in two stages with different alkylating agents. Especially pure monoalkylaminophenols are obtained by alkylation and subsequent hydrolysis from 1,3-benz0xazol-2-one.
• the sequence of the synthesis stages hitherto described, up to the final product, can also be changed and suited to the specific properties of the carbamates. For example, it is possible first to manufacture o-nitrophenyl-carbonate or onitrophenyl-N-methylcarbamate and then to reduce and alkylate these. in the latter case the new carbamates are directly obtained, and in the former case a reaction with methylamine is still required.
• the active component can be present not only as the free base but also in the form of a salt.
• Inorganic and organic acids can be used for the salt formation, for example, sulphuric acid, hydrochloric acid, hydrobromic acid, nitric acid, phosphoric acid, oxalic acid, citric acid, methanesulphonic acid, toluenesulphonic acid, maleic acid, monochloracetic, dichloracetic and trichloractic acid and many others.
• Acid salts for example, the acid sulphate, are distinguished by good stability.
• the new carbamates of formula (I), according to the invention show very good biocidal properties in general combating of insects and pests of the order Acarina, in each case in all their stages of development. Thus cicadas are destroyed even by using small amounts of the active substance. Fruit flies are completely killed at concentrations of 2.5 ppm after one hour. The carbamates, however, generally possess exceptional pro perties in destroying blood-sucking arthropodes.
• This group of pests is not so much sub-divided through particular classes or orders but is especially characterized and defined by its behavior as parasites of warm-blooded animals.
• flies stinging flies, animal flies, tsetse flies and others
• mosquitoes yellow fever mosquito, malaria mosquito and others
• lice, bugs, fleas, and also ticks and mites should be mentioned.
• the new preparations can be employed in the most diverse manner in a solid, liquid or gaseous form, for example, in the form of sprays, dusting powders and emulsions and also in socalled fly plates or flypapers which are impregnated with a solution of at least one of the active substances.
• Possible materials for the manufacture of directly sprayable solutions of the compounds of general formula (I) are, for example, mineral oil fractions of high to medium boiling range, for example, Diesel oil or kerosene, coal tar oil and oils of vegetable or animal origin, as well as hydrocarbons, for example, alkylated naphthalenes or tetrahydronaphthalene, optionally using xylene mixtures, cyclohexanols, ketones and also chlorinated hydrocarbons, for example, trichloroethane and tetrachlorethane, trichlorethylene or trichlorobenzenes and tetrachlorobenzenes.
• Organic solvents of which the boiling point is above C are advantageously used.
• Aqueous application forms are especially appropriately manufactured from emulsion concentrates, pastes or wettable spraying powders by adding water.
• Possible emulsifiers or dispersing agents are non-ionic products, for example, condensation products of aliphatic alcohols, amines or carboxylic acids having a long-chain hydrocarbon residue of about 10 to 20 carbon atoms with ethylene oxide, for example, the condensation product of octadecyl alcohol and 25 to 30 mols of ethylene oxide, or that of technical oleylamine and 15 mols of ethylene oxide or that of dodecylmercaptan and 12 mols of ethylene oxide.
• anionic emulsifiers which can be employed there may be mentioned: the sodium salt of dodecyl alcohol sulphuric acid ester, the sodium salt of dodecylbenzenesulphonic acid, the potassium or tn'ethanolamine salt of oleic acid or of abietic acid or of mixtures of these acids, or the sodium salt of a petroleum-sulphonic acid.
• Possible cationic dispersing agents are quaternary ammonium compounds, for example, cetylpyridinium bromide, or dihydroxyethylbenzyldodecylammonium chloride.
• Talc kaolin, bentonite, calcium carbonate, calcium phosphate, but also charcoal, cork powder, wood flour and other materials of vegetable origin can be employed for the manufacture of dusting agents and scattering agents, for example for combating mites in poultry.
• the manufacture of the preparations in a granular form is also to be recommended for special uses.
• the various forms of use can be provided in the usual manner with additions of substances which improve the distribution, the adhesion, the rain resistance or the penetrating power; amongst these there may be mentioned: fatty acids, resin, glue, casein or alginates.
• the preparations according to the invention can be employed by themselves or together with customary pesticides, especially insecticides, acaricides, nematocides, bactericides and fungicides.
• the concentration of the active ingredient employed can vary within wide limits depending on the nature of the use. It is generally 0.01 percent by weight of 20 percent by weight for more dilute preparations, whilst more concentrated preparations contain 20 percent by weight to 98 percent by weight of active ingredient. Preparations of maximum concentration are, say, used in the so-called ULV technique (ultra-low volume) with minimum amounts of additives.
• ULV technique is employed with very finely atomizing spraying equipments, preferably with the aid of aircraft.
• the action of the carbamates according to the invention can be further increases by synergistic agents.
• Dusting agents Equal parts of an active substance according to the invention and of precipitated silica are finely ground. Dusting agents preferably containing one to six percent of active substance can be manufactured therefrom by mixing with kaolin or talc. Spraying powders In order to manufacture a spraying powder, the following components are for example mixed and finely ground:
• HlSlL highly adsorbent silica
• Bolus alba kaolin
• a reaction product of p-tert. octylphenol and ethylene oxide 1.5 parts of sodium 1-benzyl-2-stearyl-benzimidazole-6,3'-
• Emulsion concentrate Easily soluble active substances can also be formulated as an emulsion concentrate according to the following instruction:
• EXAMPLE 1 a Concentration experiment Female mosquitoes are placed for six hours on a coating of the substance to be tested, in Petri dishes of ll cm diameter. This coating is produced by treating the bottom of the dish with 1 ml of a solution of the substance in acetone and subsequent drying for one hour. Solutions of 1,000, 100, and 1 ppm are employed, corresponding to a concentration of 1, 0.1, 0.01 and 0.001 mg of active substance/dish lmg/dish E l g/9.4 m). The mosquitoes are cooled in ice and counted out 10 at a time into the dishes. 4 repeats are run per concentration. The evaluation takes place after 45, 90 and 360 minutes.
• mosquitoes After an exposure time of 2, 4, 8, 16, 32, 60 or 120 minutes the mosquitoes are again briefly anaesthetised and introduced into a clean Petri dish with fodder (honey water).

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

Applications Claiming Priority (2)

Publications (1)

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Cited By (3)

• 1969
  • 1969-10-16 DE DE19691952230 patent/DE1952230A1/de active Pending
  • 1969-10-20 US US867862A patent/US3676486A/en not_active Expired - Lifetime
  • 1969-10-20 IL IL33218A patent/IL33218A/en unknown
  • 1969-10-21 FR FR6936082A patent/FR2022311A1/fr not_active Withdrawn
  • 1969-10-21 CS CS696669A patent/CS157075B2/cs unknown
  • 1969-10-24 GB GB52231/69A patent/GB1244414A/en not_active Expired
  • 1969-10-25 JP JP44085171A patent/JPS4824250B1/ja active Pending

Non-Patent Citations (2)

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