DE1175243B - Process for the preparation of sulfur-containing pyrazine derivatives - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Boarding school KL: C07d

German class: 12p-6

Number: 1175 243

File number: F 32596IV d / 12 ρ

Filing date: November 22, 1960

Opening day: August 6, 1964

It has been found that sulfur-containing pyrazine derivatives are obtained by using a method known per se Way 2,3-dimercaptopyrazine of the formula Process for the preparation of sulfur-containing pyrazine derivatives

with phosgene, thiophosgene, thionyl chloride or sulfuryl chloride.

This reaction leads to binuclear heterocyclic compounds.

The compounds obtainable according to the invention surprisingly have better insecticidal properties Effectiveness than that according to the published documents of the Belgian patent 580 478 known quinoxaline derivatives with an analogous structure, applicant:

Paint factories Bayer Aktiengesellschaft, Leverkusen

Named as inventor: Karlfried Dickore, Leverkusen, Klaus Sasse, Cologne-Stammheim, Richard Wegler, Leverkusen

as can be seen from the following results of comparative experiments.

links use
against Active ingredient
concentration
in ° / o Mortification
the pests Complete
Mortification
after minutes Fly maggots 0.1 100 - (Example 1) [Y 1 ^{c = s}
VA _n A ₈ / Fly maggots 0.1 0 - (known from the well-known
made documents of the belgi
patent 580 478) (T c = o
(Example 2) To fly
Grain beetle
Fly maggots
Scrape
Mosquitoes 0.01
0.01
0.01
0.01
0.01 100
100
100 60
60 YY YC = O
VA _n A ₈ /
(known from the well-known
made documents of the belgi
patent 580 478) To fly
Grain beetle
Fly maggots
Scrape
Mosquitoes 0.1
0.1
0.1
0.1
0.1 I OO O I 240
180

409 639/405

The comparative experiments were carried out as follows: First, an active ingredient preparation is used prepared by adding 1 part by weight of the active ingredient in about 1 part by weight of dimethylformamide dissolves, about 0.2 part by weight of an emulsifier is added and this concentrate with water on the desired final concentrations.

When testing against fly maggots, about ten fly maggots are placed in a covered petri dish laid, in which a dripping wet filter paper lies, which is soaked with the active ingredient solution beforehand has been. The degree of destruction is determined after 10 days.

To determine the effect against grain beetles, about ten grain beetles are placed in a covered one Petri dish, in which there is a dripping wet filter paper, which was previously filled with the active ingredient solution was soaked. The degree of destruction is determined after 24 hours.

To determine the effect against flies, put about fifty flies in a covered Petri dish, in which there is a dripping wet filter paper, which was previously filled with the active ingredient solution was soaked. The degree of destruction is determined after 24 hours.

To determine the effect against cockroaches, about ten cockroaches are placed in a covered Petri dish given, in which there is a dripping wet filter paper, which was previously with the active ingredient solution was soaked. The degree of destruction is determined after 24 hours.

To determine the effect against mosquitoes, about ten mosquitoes are covered in one Given a Petri dish, in which there is a dripping wet filter paper, which was previously filled with the active substance solution was soaked. The degree of destruction is determined after 24 hours.

The production of the new substances takes place according to methods known per se. So you can 2,3-Dimercaptopyrazine in aqueous solution, in mixtures of water and miscible with water or immiscible organic solvents or in inert organic solvents such as hydrocarbons, Dioxane or acetone, in the presence of acid-binding agents with the acid-chlorides mentioned realize. The reaction mixtures are worked up according to the methods used in organic chemistry usual methods.

The following examples illustrate the invention.

example 1

6 g of thiophosgene are added ^{dropwise at 0 to 5 °} C. to a solution of 7.2 g of 2,3-dimercaptopyrazine in a solution of 5 g of sodium hydroxide in 100 ml of water. The mixture is stirred for 1 hour at room temperature, the precipitated solid product is filtered off with suction, washed with water and dried in vacuo. 7 g (75% of theory) of the cyclic trithiocarbonate of the formula are obtained

F. = 169 to 171 ⁰ C.

Example 2

28.8 g of 2,3-dimercaptopyrazine are suspended in 250 ml of toluene, a concentrated aqueous solution of 16 g of sodium hydroxide is added and the water is azeotropically distilled off. Then passed without cooling phosgene, where the internal temperature to about 6O ⁰ C is rising, then the solvent is heated with further introduction to boiling, and finally distills off all of the solvent in vacuo.

The residue is recrystallized from acetone. 27 g (80% of theory) of the compound are obtained the formula

C = O

M.p. = 81 ° C.

Claims (1)

Claim: Process for the production of sulfur-containing pyrazine derivatives, characterized in that that in a known manner 2,3-dimercaptopyrazine of the formula with phosgene, thiophosgene, thionyl chloride or sulfuryl chloride. Considered publications:
Notice of publication of the Belgian patent No. 580 478. 409 639/405 7.64 θ Bundesdruckerei Berlin