DD156810A1 - PROCESS FOR SYNTHESIS OF IN 1-POSITION SUBSTITUTED 6-ALKYLTHIO-4-AMINO-2-IMINO-1,2-DIHYDRO-1,3,5-TRIAZINENE - Google Patents

Abstract

The present invention relates to a process for the synthesis of 1-position-substituted 6-alkylthio-4-amino-2-imino-1,2-dihydro-1,3,5-triazines. The representatives of this class of substances claim as Abkoemmlinge of 1,3,5-triazine greater interest. These are potential crop protection products. So far, no method has been described in the patent and technical literature that allows the synthesis of these substances with a corresponding substituent pattern. The aim of the invention is to make this class of interesting substances accessible and, by varying the starting materials, to enable the synthesis of a large number of these compounds. The object is achieved in that N-cyanguanyl-imido-dithiokohlensaeurediester with primary amines in polar solvents, preferably alcohols having 1 to 4 carbon atoms, at temperatures between 30 degrees C and 120 degrees C to the substituted in 1-position 6- Alkylthio-4-amino-1,2-dihydro-1,3,5-triazines are reacted.

Description

Process for the synthesis of 1-substituted-6-Allryl-thio-4-amino-2-imino-1,2-dihydro-1,3,5-triazines

Field of application of the invention

The invention relates to a process for the synthesis of substituted in 1-position 6-All ^ lthio-4-amino-2-imino-1,2-dihydro-1,3,5-triazinen.Die biocidal activity of various derivatives of 1,3 | 5 ~ Triazines has been well known for a long time, so that the here presented substituted in the 1-position 6-alkylthio-4-amino-2-imino-1,2-dihydro-i, 3 »5-triazines for the crop protection of are of greater interest »

Characteristic of the known technical solutions

The class of 1-substituted-6-alkylthio-4-amino-2-imino-1,2-dihydro-1,3,5-triazines has hitherto not been described in the patent and technical literature The number of different syntheses for differently substituted dihydro-1,3,5-triazines, however, none of these methods, the representation of the described by una triazine derivatives having a corresponding substituent pattern to.

Object of the invention

The invention is based on the object by a suitable

Process to open the previously unknown in 1-position substituted 6-alkylthio-4-amino-2-imino-1,2-dihydro-1,3 »5-triazines. Using cheap, technically available starting materials, the process should lead to a large number of representatives of this substance class with any substituent pattern

Explanation of the invention of the invention

The object is achieved in that N-Gyanoguanyl-imido dithiokohlensäuredialkylester of the formula J [in which R is substituted or unsubstituted, branched or unbranched alkyl radicals having 1 to 4 carbon atoms or for substituted or unsubstituted benzyl radicals, with primary amines the

Formula 2, in which R represents substituted or unsubstituted branched or unbranched alkyl radicals, substituted or unsubstituted benzyl radicals or hetaryl radicals, implemented v / earth.

C C

I i

-l / А /

The reactions are carried out without pressure at temperatures between 30 ^° C. and 120 ^° C. in polar solvents, preferably alcohols having 1 to 4 carbon atoms. The reaction products are crystalline during the reaction in good yield and high purity. They can be further purified by recrystallization from DMF / ethanol. The advantage of the invention is the pressure-free, single-stage synthesis, which can be carried out without any technical effort. It leads to a large number of biological

interesting compounds using inexpensive, technically readily available starting products ·

The invention is illustrated by embodiments without being limited thereto.

embodiment

4-amino-2-amino-6-methylthio-1-n-propyl-1,2-dihydro-1,3,5-triazine

0.01 LIoI IJ-cyanguanyl-imido-dithiokohlensäiiredimethylester v / ird with 0.015 mol of n-propylamine in 30 ml of ether and boiled in a water bath for about two hours. The sparingly soluble crystals are recrystallized from ethanol. Pp .: 169-71 ⁰ C (Z.) Yield: 74.3 % d. Th.

2. 4-Amino-1-o-chlorobenzy1-2-imino-6-methylthio-i, 2-dihydro-1,3,5-triazine

0.01 l of IT-cyanguanyl-imido-dithiokohlensäuredimethylester are dissolved in 30 ml of ethanol and treated with 0.01 I.Iol o-chlorobenzylamine. The solution is refluxed until the end of the mercaptan development. The crystallizing product is filtered off with suction and recrystallized from DMF / ethanol for further purification

Pp .:> 205 ° C (Z.) Yield: 85.7 % d. Th.

3. 4-Ainino-i-p-chlorobenzyl-2-ітіпо-б-теthylthio-1,2-dihydro-1,3,5-triazine

0.01 mol of IT-Cyanguanyl-imido-dithiokohlensäuredimethylester v / erden implemented analogously to Example 2 with 0.01 IJoI p-chlorobenzylamine

Pp .:> 207 ^° C (Z.) Yield: 66.6 % d. Th.

4 »4-amino-1-benzyl-2-imino-6-methylthio-1,2-dihydro-1» 3,5-triazine

0 _f 01 LIoI H-Cyanguanyl-imido-dithiokohlensäui ^ edimethylester are dissolved in 30 ml of ethanol and treated with 0.01 mol of benzylamine. The mixture is stirred for 30 minutes. at 65 ⁰ C and then one hour at boiling temperature. Workup and purification of the reaction product is carried out analogously to Example 2 · mp _e : 200 - 04 ⁰ C (Z.) Yield: 95.4 % d. Th.

5. 4-Amino-1-furfuryl-2-indilo-6-ethyl-1,2-dihydro-1,3,5-triazine

0.01 mol of Il-Cyangiianyl-imido-dithiokohlensäuredimethylester be implemented analogously to Example 2 with 0.01 mol of furfurylamine.

Pp .: ^ 197 ⁰ O (Z.) Yield: 78.2 % d. Th.

Claims (1)

Erfindungsanspi-oh 1 · A process for the synthesis of 1-substituted in one position ß-alkylthio ^ -amino-a-imino-i, 2-dihydro-1 _# 3 | 5 ~ triazines of the formula ^, in which R is a substituted or unsubstituted, branched or unbranched alkyl radical having 1 to 4 carbon atoms or for a substituted or ρ unsubstituted benzyl radical and R are substituted, unsubstituted, branched or unbranched alkyl radicals, substituted or unsubstituted benzyl or Hetarylreste, characterized in that N-Cyanguanylimido ~ dithiokohlensäurediester of formula 1_, in which R has the above meaning, with primary amines of formula 2 , in which R has the above meaning, has been implemented 1.1, The method of item 1 #, characterized Flass, the reactions without pressure at temperatures between 30 ⁰ C and 120 ⁰ C are carried out in polar solvents, preferably alcohols with 1 to 4 carbon atoms, ·