2 ethylamino-4-piperidyl-6-[4'-methylcarbamyl-5'-methyl-1',2', 3'-triazole)-1-yl]-1,3,5 - triazine as an antidote

 

(57) Abstract:

The invention relates to organic chemistry, in particular to derive SIM-triazine-2-ethylamino-4-piperidyl-6-[(4’-methylcarbamyl-5’-methyl-1’,2’,3’,-triazole)-1-yl]-1,3,5-triazine structure:

as an antidote from fetotoksicheskoe action of the herbicide 2,4 - dichlorophenoxyacetic acid in sunflower seedlings. table 2.

The invention relates to the field of chemistry and agriculture, specifically to the derived series of 1,3,5-triazine as a compound that protects against fetotoksicheskoe actions of herbicides in the cultivation of sunflower (antidote).

Known trimethylammonium salt derivatives SIM-triazine structure

containing alkylamino substituents in positions 4,6-triazine cycle, such as-N(CH3)2and - N(C2H5)2which are used as intermediates in the reactions of cyclization upon receipt bicyclic annelated derivatives SIM-triazine (centuries Dovlatyan, K. A., Eliasen, A. C. Dovlatyan. Rearrangements in the row halogenoalkane(amino)-SIM-triazines. - CHC. 1977, No. 7, S. 989-992). The use of such salts as compounds with the antidote"ptx2">

as a soil antidote protecting sunflower plants from fetotoksicheskoe action of 2,4-dichlorophenoxyacetic acid and its butyl ether (herbicide 2,4-D and EB 2,4-D) (Chemical encyclopedia. - M.: Soviet encyclopedia. 1983, C. 550). The disadvantages of using DMK are low efficiency, relatively high costs of its (200 g/ha of the active ingredient), the inability to effectively increase the length of roots of sunflower seedlings and yield on the background of the use of herbicides and the need for soil application.

Technical solution to the problem is to effectively increase the length of the roots and hypocotyls of seedlings of sunflower in the background fetotoksicheskoe of herbicides and expand the range of known antidotes.

This object is achieved by obtaining a new connection 2-ethylamino-4-piperidyl-6-[(4’-methylcarbamyl-5’-methyl-1’,2’,3’-triazole)-1-yl]-1,3,5-triazine of the formula

which can be used as an effective water-soluble antidote from fetotoksicheskoe action of the herbicide 2,4-dichlorophenoxyacetic acid on the seedlings of sunflower.

The novelty of the claimed proposal is seen in what is et to increase the length of the roots and hypocotyl last.

In this case the claimed connection get known method the interaction of the corresponding 2-azido-4,6-disubstituted 1,3,5-triazines with equimolar number of methylene-active dicarbonyl compounds in solution, in dimethylformamide in the presence of triethylamine at a temperature of 30-40C (General organic chemistry. /Edited by D. Barton and U. D. of Malaise. - M.: Chemistry. 1981, T. 1, S. 268]. The original 2-azido-4,6-disubstituted 1,3,5-triazine also get a known method (Weigand-Hilgetag. Methods experiment in organic chemistry. - M.: Chemistry, 1969, S. 443).

Used dimethylformamide and triethylamine immediately before use are cleaned and dried by known methods (A. Gordon, R. Ford. Satellite chemist. - M.: Mir. 1976. - 541 S.].

Examples of execution of their proposals.

Example 1. 2 ethylamino-4-piperidyl-6-[(4’-methylcarbamyl-5’-methyl-1’,2’,3’-triazole)-1-yl]-l,3,5-triazine (APMT). To a solution of 1 g (4.3 mmol) of 2-azido-4-piperidyl-6-ethylamino-1,3,5-triazine in 10 ml of dry and cleaned dimethylformamide under stirring and the temperature T, added dropwise a mixture of 0.99 g (8.6 mmol) of acetylacetone and 0.87 g (8.6 mmol) of triethylamine. The reaction mixture is stirred for 50 h at 35-40C and under stirring with a thin straydog of residual solvent and triethylamine and dried at 50-60C. Obtain 0.97 g (98.9 per cent) APMT in the form of a white powder with so pl. 139-140 C, insoluble in water and soluble in alcohol, acetone, methylene chloride and other polar organic solvents.

Found, %: C 54,66; N 6,89; N 34,13. C15H22N8O. Calculated, %: C 54,52; N. Of 6.71; N 33,92.

X , cm-1(group): 3335-3230 ush.S., (NH); 1665 cf. (C=O); 1590, 1550, 1530 c. (C=C, C=N - t. and cyanurates cycle.).

DMR , M. D. (group): of 7.90 (1H, s, NH); 3,70-of 3.85 (2H square, MSN2(CH3) J=7,0; 3,35 is-3.45 (4H, m, NCH2); to 2.85 (3H, S=CLO3); to 2.65 (3H, PINES3); 1,55-1,75 (6N m, CHPiperidyl)); 1,15-1,25 (3H, t, NHCH2CH3) J-7,0.

Mol. ion (mass by a spectroscope) 330.

Example 2. 2 ethylamino-4-piperidyl-6-[(4’-methylcarbamyl-5’-methyl-1’,2’,3’-triazole)-1-yl]-1,3,5-triazine (APMT). Under conditions analogous to example 2, 1 g (4.3 mmol) of 2-azido-4-piperidyl-6-ethylamino-1,3,5-triazine, 0,99 g (8.6 mmol) of acetylacetone and 0.87 g (8.6 mmol) of triethylamine, with the only difference that 2-azido-4-piperidyl-6-ethylamino-1,3,5-triazine are added to a mixture of acetylacetone and triethylamine, and the process of peremeshivanija reduced to 45 hours, receive 0.97 g (98.9 per cent) APMT in the form of a white powder with so pl. 139-140 C, all constants which meet those for APMT in example 1.

The floor is and sunflower in laboratory experience. While preparing for his workers aqueous solutions of concentrations from 0.01 to within 0.00001 wt.% and process sunflower seeds varieties VNIIMK 8883, pre-sprayed with a dispersion of 2,4-D, as described below in example 3. For comparison, using an aqueous solution DMK (prototype). Due to the poor solubility in water source APMT and DMK pre “podrastet” in a small amount of alcohol. As a control, use the option of processing water.

Example 3. In laboratory experience seedlings of sunflower (25 seedlings per Cup in five replicates) after 4 days from the beginning of germination at 23 ° C is subjected to the successive action of water dispersion of the herbicide 2,4-D, and after 1 h in an aqueous solution of the stated APMT or known DMK given concentration. Continue germination under the same conditions for another 3 days and determine the root length of seedlings (data bring to the table). The decrease in root length and hypocotyl in the advanced options in comparison with control (Amind.in % is determined by the formula

ANDmind=(O/K)100,

where To and length of seedlings in the control and experimental variants, respectively.

Examples 4-9 carry out strictly the same experience 3 way. For comparison, in analogion the totype), and experience 8 - using to process only herbicide (standard) and control experience 9 - water treatment without the use of herbicide and antidote.

All experimental data are subjected to statistical analysis using t-student test at a confidence level of 0.95.

As can be seen from the data table.1, the application on the background of the impact of the herbicide 2,4-D proposed 2-ethylamino-4-piperidyl-6-[(4’-methyl-carbonyl-5’-methyl-1’,2’,3’-triazole)-1-yl]-1,3,5-triazine (APMT) as an antidote provides in comparison with the standard increase in root length of seedlings of sunflower by 34.6-50% (35-39 instead of 26 mm), while the use of known means 1,2-dioxymethylene provides an increase of only 16.4%. It is also clear that if as a result of fetotoksicheskoe steps reference (example 8) length of roots of seedlings is reduced in comparison with the control 71,43%, the use of the claimed APMT reduces fetotoksicheskoe herbicide action and length of roots decreased by 61.5-57,2,1%, while the use of known compounds prototype DMK - reduces this figure is 67.1%.

As can be seen from the data table.2, the application on the background of the impact of the herbicide 2,4-D proposed 2-ethylamino-4-pet in comparison with the benchmark of increasing the length of the hypocotyl of seedlings of sunflower 16.3-23% (40,7-40,3 instead of 35 mm), while the use of known means 1,2-dioxymethylene provides an increase of only 5.7%. It is also clear that if as a result of fetotoksicheskoe steps reference (example 8) length of roots of sunflower seedlings is reduced in comparison with control 52.7%, the use of the claimed APMT reduces fetotoksicheskoe herbicide action and length of roots decreases by only 45-47,9%, while the use of known compounds prototype DMK - reduces this figure to 50%.

The claimed connection APMT shows antidote effect when the concentration of the working solution of 0.01 to within 0.00001 wt.%, in which well-known compound prototype generally unhealthy, which confirms the greater efficiency and much lower costs claimed connection on the far East.

Thus, the use of the claimed compounds 2-ethylamino-4-piperidyl-6-[(4’-methylcarbamyl-5’-methyl-1’,2’,3’-triazole)-1-yl]-1,3,5-triazine as an antidote allows for the impact of herbicide to increase the length of the roots and hypocotyls of sunflower seedlings, as well as to expand the range of known antidotes.

2 Ethylamino-4-piperidyl-6-[(4’-methylcarbamyl-5’-methyl-1’,2’,3’-trucido 2,4-dichlorophenoxyacetic acid in sunflower seedlings.

 

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