Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
  • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
• • G—PHYSICS
  • G05—CONTROLLING; REGULATING
  • G05B—CONTROL OR REGULATING SYSTEMS IN GENERAL; FUNCTIONAL ELEMENTS OF SUCH SYSTEMS; MONITORING OR TESTING ARRANGEMENTS FOR SUCH SYSTEMS OR ELEMENTS
  • G05B2219/00—Program-control systems
  • G05B2219/20—Pc systems
  • G05B2219/24—Pc safety
  • G05B2219/24108—Correct fault so that microprocessor functions correctly, without reset

Definitions

• the present invention relates to new N, N-dialkyl-O-pyrimidinyl-carbamic acid esters, processes for their preparation and their use as insecticides.
• N, N-dimethyl-O-pyrimidinylcarbamic acid esters e.g. N, N-dimethyl-0- (2-isopropyl-6-methyl-pyrimidine (4) yl) - or -O- (2-dimethylamino-6-methyl-pyrimidine (4) yl) -carbamic acid esters have insecticidal properties (see USA - Patent 2 694 712 and British Patent 1 181 657).
• the N, N-dialkyl-O-pyrimidinyl-carbamic acid esters according to the invention have a better insecticidal action than the compounds 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 2-hydroxy-4'-dialkylamino-pyrimidines (II) to be used as starting materials can be prepared by processes known from the literature; in the event that R 4 is hydrogen, alkyl or halogen, from the corresponding 2-halogen compounds by hydrolysis and in the event that R 4 is alkylthio, from the corresponding 2-hydroxy- 'pyrimidines which are unsubstituted in the 5-position , Dimethyl disulfide and sulfuryl chloride optionally in the presence of a solvent.
• the processes for the preparation of the compounds according to the invention are 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, optionally 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, and also nitriles, such as aceto and propionitrile.
• hydrocarbons such as benzene, toluene, xylene, gasoline, Methylene chloride, chloroform, carbon tetrachloride, chlorobenzene, or
• All customary acid binders can be used as acid acceptors.
• Alkali carbonates and alcoholates such as sodium and potassium carbonate, methylate or ethylate, and also aliphatic, aromatic or heterocyclic amines, for example trimethylamine, triethylamine, dimethylaniline, dimethylbenzylamine and pyridine, have proven particularly useful.
• the reaction temperature can be varied within a wide range. Generally one works between 0 and 100 ° C, preferably at 30 to 80 ° C.
• the reaction is generally allowed to proceed at normal pressure.
• the carbamic acid halide component is preferably used in a 10 to 30% excess.
• the reactants are usually combined in an organic solvent in the presence of an acid acceptor and boiled under reflux. If necessary, the undissolved is filtered off and concentrated.
• the new compounds are obtained in crystalline form and are characterized by their melting point.
• N, N-dialkyl-O-pyrimidinylcarbamic acid esters according to the invention are notable for excellent insecticidal activity.
• the active ingredients can be converted into the usual 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.
• formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
• extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate 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.
• water e.g. organic solvents can also be used as auxiliary 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, e.g.
• Petroleum fractions oil 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 pressure, e.g.
• Aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers: natural rock flour, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, 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 emulsifying and / or foaming agents: nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
• 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.
• 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.
• the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
• 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.
• the root systemic effect of the active ingredient is derived from the number of killings. It is 100% when all test animals have been killed and 0% - when as many test insects are still alive as in the untreated control.
• the 2-hydroxy-4-dialkylamino-pyrimidines (II) to be used as starting materials can e.g. can be produced as follows:
• a solution of 4.7 g (0.05 mol) of dimethyl disulfide in 150 ml of methylene chloride is mixed with 6.8 g (0.05 mol) of sulfuryl chloride at -20 ° C. within 30 minutes. After 20 minutes, this solution is added dropwise at -10 ° C. to a suspension of 17 g (0.1 mol) of 2-hydroxy-4-dimethylamino-6-methyl-pyrimidine sodium salt in 200 ml of methylene chloride. The mixture is then stirred for 18 hours at room temperature. The solution is then extracted with 200 ml of water, the organic phase is dried over sodium sulfate and the solvent is distilled off in vacuo. This leaves 8.8 g (45% of theory) of 2-hydroxy-4-dimethylamino-5-methylthio-6-methyl-pyrimidine in the form of colorless crystals with a melting point of 209 ° C.

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• Agricultural Chemicals And Associated Chemicals (AREA)

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• 1977
  • 1977-07-05 DE DE19772730273 patent/DE2730273A1/de not_active Withdrawn
• 1978
  • 1978-06-14 US US05/915,623 patent/US4162320A/en not_active Expired - Lifetime
  • 1978-06-26 PT PT68215A patent/PT68215A/pt unknown
  • 1978-06-28 EP EP78100251A patent/EP0000198B1/de not_active Expired
  • 1978-06-28 DE DE7878100251T patent/DE2860049D1/de not_active Expired
  • 1978-07-03 IL IL55060A patent/IL55060A0/xx unknown
  • 1978-07-03 IT IT25287/78A patent/IT1098344B/it active
  • 1978-07-03 TR TR19760A patent/TR19760A/xx unknown
  • 1978-07-03 NZ NZ187759A patent/NZ187759A/xx unknown
  • 1978-07-03 CS CS784409A patent/CS197325B2/cs unknown
  • 1978-07-03 JP JP7984878A patent/JPS5414984A/ja active Granted
  • 1978-07-04 ZA ZA00783822A patent/ZA783822B/xx unknown
  • 1978-07-04 AU AU37757/78A patent/AU515147B2/en not_active Expired
  • 1978-07-04 DK DK783026A patent/DK302678A/da unknown
  • 1978-07-04 BR BR7804295A patent/BR7804295A/pt unknown
  • 1978-07-04 ES ES471418A patent/ES471418A1/es not_active Expired
  • 1978-07-05 EG EG419/78A patent/EG13466A/xx active
  • 1978-07-05 AR AR272844A patent/AR220717A1/es active
  • 1978-07-05 AT AT486678A patent/AT359333B/de not_active IP Right Cessation

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