DE1251576B - - Google Patents

Description

JBUN ⁱ DESREPUBLIC OF GERMANY Int. Cl .:

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GERMAN

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Godfather

German class: 451 - 9/36 £ \ θ \ KJ - / / j

EDITORIAL

Number:
File number:
Registration date:
Display day:

1,251,576
Stl9414 1Va / 451
June 29, 1962
5th October 1967

The invention relates to the use of certain compounds as insecticidal, nematocidal and acaricidal Middle. The compounds have the following formula

IO

in which R and Ri represent lower alkyl groups, X represent sulfur or oxygen and Ro and Ra represent hydrogen or lower alkyl groups. The connections can be represented as follows:

A. S- (4,6-Dimethylpyrimidyl-2) -0,0-diethyl phosphorodithioate

A mixture of 130.1 g (0.625 mol) of sodium 0,0-diethyldithiophosphate, 71.3 g (0.5 mol) of 2-chloro-4,6-dimethylpyrimidine and 500 ecm of toluene is refluxed for 3½ hours with stirring. The toluene is with a stream of air on the Steam bath evaporates. The residue is taken up in ethyl ether and water. The ethereal solution is washed with dilute aqueous saline solution, dried with anhydrous sodium sulfate and filtered. The ether is evaporated under reduced pressure. The raw product weighs 146 g (quantitative yield). A small amount of benzene was added. The solution will be dried with anhydrous sodium sulfate and filtered. The benzene is being depressed Pressure evaporates. The residue is heated to 60 to 70 ° C for 2 hours at IOOMikronHg. That Product, a light brown liquid, weighs 144.8 g (99%). n? = 1.5433.

The following can be produced in an analogous manner:

B. S- (4,6-dimethylpyrimidyl-2) -0.0-dimethylphosphorodithioate.

C. S- {4,6-Dimethylpyrirnidyl-2) -0,0-diisopropyl phosphorodithioate.

D. S- (4,6-Dimethylpyrimidyl-2) -0,0-diethyl phosphorothioate.

E. S-pyrimidyl-2-0,0-diethyl phosphorodithioate.
For the manufacturing process is under

No protection is claimed in the present invention.

The compounds were rated for their effects as insecticides and acaricides according to the following Process examined:

Insecticidal, nematocidal and acaricidal agents

Applicant: // / ~ / _r

Stauffer Chemical Company,
New York, NY (V. St. A.)

Representative:

Dr. W. Beil, A. Hoeppener and Dr. HJ Wolff,
Lawyers,

Frankfurt / M.- Höchst, Adelonstr. 58 Named as inventor: Arthur C. Thomson, San Antonio, Tex .; Mervin E. Brokke, Richmond, Calif .; Julius J. Menn, San Jose, Calif .; Richard C Maxwell, Pullman, Wash. (V. St. A.) Claimed priority: V. St. v. America June 30, 1961 (120 958) - - Testing of the acaricidal effect

The two-spotted mite, Tetranychus telarius (Linn.), Is used for the investigation. Young pinto bean plants are contaminated with several hundred mites. 0.5 g of the toxic material are dissolved in 10ccm acetone. This solution is then diluted with water, the 0.015% sulfonate wetting agent and 0.005% methyl cellulose emulsifying agent, the amount of water being sufficient to provide concentrations of the active ingredient from 0.25 to 0.005%. Then the test suspensions are grounded on the contaminated pimo bean plants injected. After 7 and 14 days, the plants are both postembryonic Forms of the mite as well as eggs were examined. The destruction percentage is through Comparison with control plants that were not sprayed and the LD-so value is determined below Calculated using known methods. In the table below, the mites are in the column "2-GM" and the embryonic forms are listed under "2-GM-E".

Examination of the insecticidal effect

Four insect species are subjected to the insecticide assessment tests:

709 650; 380

Claims (4)

1. American cockroach (cockroach)
Periplaneta americana (Linn.) 2. Large milkweed beetle (WMK)
Oncopeltus fasciatus (Dallas) 3. flour beetle (MK)
Tribolium confusum (DuvaI) 4. House fly (HF)
Musca domestica (Linn.) The procedure for the insects is similar to the test procedure for mite destruction. Test insects are locked in cardboard tubes with a diameter of 7.93 cm and a height of 6.66 cm. The cages are equipped with cellophane floors and lids made of wire mesh. Per cage will be 10 to 25 insects used. Each cage is provided with food and water. The flour beetles are locked in petri dishes with no food. The caged insects are sprayed with the active compound in various concentrations. After 24 or 72 hours, counts are made made to identify the living and dead insects. The evaluation tests for the house fly differ in this respect: the poison is in a volatile solvent, preferably acetone, and the solution is pipetted into a Petri dish inserted, then allowed to air dry and the residue placed in a cardboard tube. There are twenty-five females in the tube Flies locked up. The flies are continuously the residue of the active compound im Exposed cage. After 24 and 72 hours, respectively, counts are made to find the living and identify dead insects. The LD 50 values are calculated using known methods. The following LDöo values were achieved: link HF Cockroach WMK MK 2-GM 2-GM-E A. 5 ed 0.03% 0.10% 5 Rg 0.06% 0.12% B. 0.06% 0.10% 0.10% 0.25% C. 50 rg 0.12% D. > IOO _i Ug 0.5% 0.1% E. 1 Rg <0.01% 0.01% > 2 rg <0.005% <0.05% The diazinon used for comparison turned out to be compared to the embryonic form of the two-spotted one Mite as ineffective. The compounds of the invention were also found to be effective in destroying Roundworms. For example, S- (4,6-dimethylpyrimidyl-2) -0,0-diethylphosphorodithioate prevented at a dosage of 55 ppm, the life of root nodal worms in the soil. Otherwise S- (4,6-dimethylpyrirnidyl-2) -0,0-diethylphosphorodithioate was found and is therefore more effective than any other commercially available compound for combating apple pollen of major importance for apple, peach and walnut production. Claim:
Use of compounds of the formula RiO in which R and Ri are lower alkyl radicals, Ra and R3 are hydrogen or lower alkyl radicals and X is oxygen * or sulfur, as insecticidal, nematocidal and acaricidal agents. Considered publications:
U.S. Patent No. 2,980,675.