AT202151B - Process for the preparation of new triazine derivatives. - Google Patents

Description

  

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  Process for the preparation of new triazine derivatives.



   The present invention relates to a process for the preparation of new triazine derivatives with phytobiological activity.



   It has surprisingly been found that s-triazine derivatives of the general formula:
 EMI1.1
 wherein R is an alkyl radical or an alkenyl radical which is optionally substituted by halogen or hydroxyl groups, R ″, R, and R are hydrogen, or identical or different, optionally substituted by halogen or hydroxyl groups
 EMI1.2
 or morpholino residues mean that even in very low concentrations they have a growth-inhibiting and ultimately killing effect on plants.



   The s-triazine compounds defined above can be prepared in a simple manner by mixing cyanuric bromide in the presence of an acid-binding agent with 2 moles of an amine of the general formula:
 EMI1.3
 or with one mole each of an amine of the above formula and a different amine of the general formula:
 EMI1.4
 implemented in any order. In these general formulas II and III, R1'R2, Ra and R4 have the meaning given under formula I.



  As an acid-binding agent, for. B. an excess of the amine or amines to be reacted or an alkali metal carbonate or hydroxide are used. The reaction can e.g. B. can be carried out at room temperature or moderately elevated temperature in the presence or absence of solvents or diluents.



   For reaction with cyanuric bromide, amines of the general formula II and III are, for example, methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, n-hexylamine, allylamine, dimethylamine, diethylamine, di-n-propylamine, di-
 EMI1.5
 
Di-allylamine, N-methyl-n-butylamine, ethyleneimine, pyrrolidine, piperidine and morpholine are possible. The general formula III also includes ammonia as a further starting material.



   The following examples are intended to explain the preparation of the new compounds in more detail.



  Parts therein mean parts by weight and the temperatures are given in degrees Celsius. Example 1: 31.8 parts of cyanuric bromide are suspended in 100 parts of dioxane, and 19 parts of ethylamine in 11 parts of water are added dropwise at room temperature. The mixture is stirred for two hours at 40-500, then the sparingly soluble reaction product is filtered off and it is recrystallized twice from ethyl acetate. An analytically pure sample of 2-bromo-4,6-bis-ethylamino-s-triazine melts at 219-220. The melting point, however, depends on the rapidity of heating.



   Half of the amine can also be replaced by the equimolecular amount of sodium or potassium carbonate or sodium or potassium hydroxide.



     Example 2: 63.6 parts of cyanuric bromide are suspended in 300 parts of ice water and 53 parts of isopropylamine in 13 parts of water are added dropwise at 0 # 20. The mixture is stirred for two hours at 40-500, then the sparingly soluble reaction product is filtered off and it is recrystallized from ethyl acetate. An analytically pure sample of the 2-bromine

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 4,6-bis-isopropylamino-s-triazine melts at 200 to 204 ". The melting point, however, depends on the rapidity of heating.



   Half of the amine can also be replaced by the equimolecular amount of sodium or potassium carbonate or sodium or potassium hydroxide.



   Compounds of the general formula I defined at the beginning are particularly suitable as active ingredients for weed control agents, both for the selective suppression and eradication of weeds among crops, as well as for
 EMI2.1
 th vegetation. The compounds defined above are also suitable as active ingredients for exercising other inhibitory influences on plant growth, in particular defoliation, eg. B. of BaumwoHpSanzen, acceleration of ripening due to premature drying out, z. B. of potato plants, furthermore also reduction of fruit set, delay of flowering, extension
 EMI2.2
 producible azine, 2-bromo-4-ethyleneimino-6-ethylamino-s-triazine,
 EMI2.3


 

Claims (1)

PATENT CLAIM: Process for the production of new triazine EMI2.4 EMI2.5 EMI2.6 : Alkyl radicals substituted by halogen or hydroxyl groups, furthermore alkenyl radicals and Rl and R2 and / or Rj and R. together with the associated nitrogen atom also mean polymethylene-amino radicals or morpholino radicals, characterized in that cyanuric bromide is mixed with two moles of an amine of the general formula in the presence of an acid-binding agent: EMI2.7 or with one mole each of an amine of the above formula and a different amine of the general formula: EMI2.8 wherein R, R, Rg and R are those given above EMI2.9