Antidote against phytotoxic action of 2,4-dichlorophenoxyacetic acid herbicide onto germinated sunflower seeds

FIELD: herbicides.

SUBSTANCE: invention relates to application of 2-diethylamino-6-methoxy-4-[(4'-ethoxycarnonyl-5'-methyl-1',2',3'-triazole)-1'yl]1,3,5,-triazine of formula as antidote against phytotoxic action of 2,4-dichlorophenoxyacetic acid herbicide onto germinated sunflower seeds.

EFFECT: more effective sunflower germ root length and hypocotyl elongation on background of phytotoxic 2,4-D herbicide action.

2 tbl, 3 ex

 

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 2-methoxy-4-morpholin-6-[(4'-phenylcarbamoyl-5'-methyl-1',2',3'-triazole)-1'-yl]-1,3,5-triazine (MFT) formula:

which is the antidote from fetotoksicheskoe action of the herbicide 2,4-D on the germinating seeds and seedlings of sunflower [see Pat of the Russian Federation No. 2230066; (10.06.2004,) IPC707 D 403/04, A 01 N 43/68; Snehalatha, Ann, Ightmare, Avezov, Nscontrol, Vinsanity 2-Methoxy-4-morpholin-6-[(4'-phenylcarbamoyl-5'-methyl-1',2',3'-triazole)-1'-yl]-1,3,5-triazine as an antidote. Bull. Fig. 2004, No. 16]. The disadvantage of its use is relatively low activity in reducing fetotoksicheskoe action of the herbicide 2,4-D on seeds and seedlings of sunflower.

Technical solution to the problem is a more effective increase in the length of roots and hypocotyls of seedlings of sunflower in the background fetotoksicheskoe action of herbicides of the group of 2,4-D, as well as extending the range of known antidotes.

The task is achieved by using 2-diethylamino-6-methoxy-4-[(4'-etoxycarbonyl-5'-methyl-1',2',3'-triazole)-1'-yl]-1,3,5-triazine of the formula:

which is can be used as an effective antidote, from fetotoksicheskoe action of the herbicide 2,4-dichlorphenoxy acid in sunflower.

The novelty of the claimed proposal is seen in the application of the previously known ("TimTec Stock Library, CAS" 01.06.2004, No. 663936-89-8) connection 2-diethylamino-6-methoxy-4-[(4'-etoxycarbonyl-5'-methyl-1',2',3'-triazole)-1'-yl]-1,3,5-triazine (DMAT) (information as antidote in the literature are absent) as the antidote of seedlings and vegetative plants of sunflower, which allows to increase the length of the roots and hypocotyls of sunflower seedlings and reduce fetotoksicheskoe action herbicide.

When this connection is (DMAT) 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 30-40° [see General organic chemistry / edited by Dbarton and Udelays. - M.: Chemistry. 1981, vol. 1, s]. The original 2-azido-4,6-disubstituted 1,3,5-triazine also get a known method [see Weigand-Hilgetag. Methods experiment in organic chemistry. - M.: Chemistry, 1969. s].

Used acetoacetic ether, dimethylformamide and triethylamine immediately before use are cleaned and dried by known methods [see Agordon, Rford. Satellite chemical is and. M: Peace. 1976. - 541 S.].

Examples of performance stated suggestions are presented below.

Example 1. 2 Diethylamino-6-methoxy-4-[(4'-etoxycarbonyl-5'-methyl-1',2',3'-triazole)-1'-yl]-1,3,5-triazine (DMAT). To the solution at 3.35 g (0.01 mol) 2-azido-4-methoxy-6-diethylamino-1,3,5-triazine in 20 ml of dried and purified dimethylformamide under stirring at a temperature of 20±1°C, was added dropwise a mixture of 3.0 g (0.02 mol) of acetoacetic ester and 2.03 g (0.02 mol) of dry and fresh of triethylamine. The reaction mixture is stirred for 40 h at 35-40°and, under stirring, a squirt poured into 100 ml of chilled 10°With water. The resulting white precipitate is filtered off, washed thoroughly with water from the remnants of the solvent and triethylamine and dried at 50-60°C. Receive 1,95 g (87,0%) DMAT in the form of a white powder with TPL 100-101°insoluble in water, but soluble in polar organic solvents.

Found, %: C Repossessed A 50.01; H Of 6.49; N 29,03. With14H21N7About3. Calculated, %: C 50,13; N. Of 6.31;N 29,24.

X νcm-1(group): 1720 cf. (C=O); 1530, 1580 C. (C=C, C=N, N=N - t. and cyanurates cycle.); 1050, 1110 cf. s-O-S.

TMR, δ, ppm (group): 3,2-4,40 (2N square, co2CH3J-4,5); 3,56-3,85 (N, m, NCH2+Co3); 2.83 (3H S.=CLO3); 1,53-1,73 (6N m, CH2 piperidyl)); 1.32-1.40 (3H, t, och2CH2) J=4,5.

Mol. ion (mass by a spectroscope) 335.

When is EP 2. 2 Diethylamino-6-methoxy-4-[(4'-etoxycarbonyl-5'-methyl-1',2',3'-triazole)-1'-yl]-1,3,5-triazine (DMAT). Under conditions analogous to example 1, from the 3.35 g (0.01 mol) 2-azido-4-methoxy-6-diethylamino-1,3,5-triazine 2.6 g (0.02 mol) of acetoacetic ester and 2.02 g (0.02 mol) of dry and fresh of triethylamine, with the only difference that the addition of acetobromo ether and triethylamine carried out at 23±1°and the stirring of the mixture continued for 38 h at 40-43°receive 1,95 g (87,0%) DMAT in the form of a white color powder with TPL 100-101°insoluble in water, but soluble in polar organic solvents.

Found, %: C Repossessed A 50.01; H Of 6.49; N 29,03. With14H21N7About3. Calculated, %: C 50,13; N. Of 6.31; N 29,24.

X ν, cm1(group): 1720 cf. (C=O); 1530, 1580 C. (C=C, C=N, N=N - t. and cyanurates cycle.); 1050, 1110 cf. s-O-S.

TMR, δ, ppm (group): 3,2-4,40 (2N square, co2CH3J=4,5); 3,56-3,85 (N, m, NCH2+Co2); 2.83 (3H S.=CLO3); 1,53-1,73 (6N m, CH2 piperidyl)); 1.32-1.40 (3H, t, och2CH3) J=4,5.

Mol. ion (mass by a spectroscope) 335.

DMAT used to reduce fetotoksicheskoe action of the herbicide 2,4-D on germinated seeds (seedlings) of sunflower in laboratory experience. While preparing for his workers aqueous solutions of concentrations from 0.01 to within 0.00001 wt.% and treated germinated sunflower seeds varieties VNIIMK 8883, in advance of Riscani water dispersion of 2,4-D (standard) as follows, example 3. For comparison, using an aqueous solution MFT (prototype). Due to the poor solubility in water, used MFT, GMAT and 2,4-D pre "podrastet" in a small amount of alcohol. As a control, use the option of processing water.

Example 3. In laboratory experience, couched in constantly moist filter paper in a Petri dish sunflower seeds (25 seeds per Cup in five replicates) after 4 days from the beginning of germination at 23°subjected to sequential exposure to aqueous dispersions of the herbicide 2,4-D, and after 1 h in an aqueous solution of the stated DMAT a 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/C)·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. To control spending experience 4 using only water (control) as well as experience using only the herbicide 2,4-D in the specified concentrations (reference). For comparison, in similar conditions and conduct experiments using as an antidote known connections MFFT. All the experts who mental data is subjected to statistical processing, 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 connection DMAT as antidote provides in comparison with the standard increase in root length of seedlings of sunflower on 45,16-70,96% (45-53 mm instead of 31 mm in the case of the standard), while the use of known means MFT provides an increase of only 23.1-46,0% (32-38 mm instead of 26 mm in the case of the standard). It is also clear that if as a result of fetotoksicheskoe steps of the standard length of the hypocotyl of seedlings is reduced in comparison with control at 64.5 per cent (30 mm instead of 66), the application stated DMAC reduces fetotoksicheskoe herbicide action and the length of the hypocotyl is increased in comparison with the standard up to 38.3-58,3% (41,5-47.5 mm), while the application of the known compounds of the prototype MFT reduces this figure only 8.9-14.3 per cent.

Thus, the use as an antidote 2-diethylamino-6-methoxy-4-[(4'-etoxycarbonyl-5'-methyl-1',2',3'-triazole)-1'-yl]-1,3,5-triazine allows background fetotoksicheskoe effects of the herbicide 2,4-D, to increase the length of the roots and hypocotyls of seedlings, as well as to expand the range of known antidotes.

The use of 2-diethylamino-6-methoxy-4-[(4'-etoxycarbonyl-5'-methyl-1,2',3'-triazole)-1'-yl]-1,3,5-triazine (DMAT) formula

as an antidote from fetotoksicheskoe action of the herbicide 2,4-dichlorophenoxyacetic acid on sprouted sunflower seeds.



 

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