RU2146251C1 - 1,2,4-triazine azomethines having growth regulating and herbicidal activities - Google Patents

Abstract

FIELD: agriculture. SUBSTANCE: described are new 1,2,4-triazine azomethines of general formula I:

Description

 The invention relates to the field of chemistry of heterocyclic compounds, namely to derivatives of 1,2,4-triazines having growth-regulating activity, and which can be used in agriculture.

где R¹ = SH, n-C₆H₄NO₂;
R² = фурил, H;
R³ = фурил, n-C₆H₄Cl.Close in structure (prototype) are 1,2,4-triazines (publ. Application N 93019009/04, CL C 07 D 253/065, 1993. - B. I. N 6, 1996) of the General formula

where R ¹ = SH, nC ₆ H ₄ NO ₂ ;
R ² = furyl, H;
R ³ = furyl, nC ₆ H ₄ Cl.

 with growth regulating activity. The disadvantage of these compounds is the limited selectivity.

 The invention solves the technical problem of increasing the productivity of crops.

где R - фенил, n - хлорфенил, фурил, бутил.The invention consists in the creation of new compounds of the heterocyclic series by reaction

where R is phenyl, n is chlorophenyl, furyl, butyl.

 The preparation of new compounds is illustrated by the following examples.

 Example 1. 5-Phenylazomethino-3,6-dimethyl-1,2,4-triazine.

 In a three-necked flask equipped with a mechanical stirrer, a Dean-Stark trap, and a thermometer, 2 g (0.016 mol) of 5-amino-3,6-dimethyl-1,2,4-triazine, 50 ml of toluene, 1.63 g (0 , 0154 mol) of benzaldehyde; 0.0363 g (0.0002 mol) of n-toluenesulfonic acid. The reaction mixture was boiled until the water evolution ceased, cooled, toluene was distilled off under vacuum. The product was washed with diethyl ether and dried. 3.1 g (91%) of 5-phenylazomethino-3,6-dimethyl-1,2,4-triazine were obtained.

Mp 130 ^o C (decomp.).

UV spectrum (nm) 336
IR (cm ^-1 ) 1600-1650, 1670
Mass spectrum (m / e) 212, 184, 156, 28
Elemental analysis (%):
Found: 26.0 N
Calculated: 26.4 N
Example 2

 Under similar conditions, 5-n-chlorophenylazomethino-3,6-dimethyl-1,2,4-triazine was obtained from 5-amino-3,6-dimethyl-1,2,4-triazine and n-chlorobenzaldehyde.

Yield 93%, mp. 152 (decomp.)
UV spectrum (nm) 336
IR (cm ^-1 ) 1600-1650, 1670, 740
Mass spectrum (m / e) 246.5; 218.5; 190.5; 28
Elemental analysis:
Found: 22.3 N, 14.0 Cl
Calculated: 22.7 N, 14.4 Cl
Example 3

 Under similar conditions, 5- (2-furylazomethino) -3,6-dimethyl-1,2,4-triazine was obtained from 5-amino-3,6-dimethyl-1,2,4-triazine and furfural.

Yield 89%, mp. 180 ^o C (decomp.)
UV spectrum (nm) 336
IR (cm ^-1 ) 1600-1650, 1670, 1150
Mass spectrum (m / e) 202, 174, 146, 28
Elemental analysis:
Found: 27.3 N, 7.5 O
Calculated: 27.7 N, 7.9 O
Example 4
Under similar conditions, 5-butylazomethino-3,6-dimethyl-1,2,4-triazine was obtained from 5-amino-3,6-dimethyl-1,2,4-triazine and valerian aldehyde.

Yield 95%, mp. 243 ^o C
UV spectrum (nm) 336
IR (cm ^-1 ) 1600-1650, 1670
Mass spectrum (m / e) 192, 164, 136, 28
Elemental analysis:
Found: 29.6 N
Calculated: 29.2 N
Example 5. Laboratory testing of compounds.

The sticky seeds of barley, wheat, corn, oats, radishes, peas, sunflowers, cucumbers were laid out in Petri dishes and 4 ml of an aqueous solution of preparations with a concentration of 1 to 500 mg / l were poured. Then the Petri dishes were placed in a thermostat at a temperature of 26 ^o C for four days. After this period, the effectiveness of the compounds was determined in comparison with the control (distilled water) and the prototype. The length and weight of the seedlings of the taken cultures served as indicators of the action of the preparations. The test results are given in table. 1.

 Given in the table. 1 data show that new compounds in doses of 1-10, and sometimes 100 mg / l, have a stimulating effect, which affects the increase in the length (L) and mass (m) of the seedlings. In terms of activity, they are not inferior to the prototype. At a dose of 500 mg / l, and in dicotyledonous plants (radishes, peas, cucumbers, sunflowers) and at a dose of 100 mg / l, new compounds exhibit inhibitory activity. On cereals (barley, wheat, corn), inhibition was not observed. This suggests that new compounds are capable of causing plant inhibition with an increase in the dose. The data table. 1 also indicate that the compounds exhibit selectivity for cereal crops.

 Example 6. Vegetation tests.

 The seeds of barley, wheat, millet, oats, radish, cucumbers, and thyroid were poured for 12 hours in a solution of the tested preparations. The concentration of the working solution is 10 and 500 mg / l. Treated seeds were sown in vegetation vessels with a diameter of 25 cm. Each species was sown in a separate vessel. The repetition of each option is fourfold. The duration of the experiment is 30 days from the day of sowing seeds. The test results are given in table. 2.

 The data show that new compounds at a dose of 10 mg / l stimulate growth processes in all plant species taken. The degree of activity is different, the highest values are achieved in cereals (wheat, barley). The effectiveness of the compound exceeds the prototype.

 At a dose of 500 mg / l, the compounds inhibit the growth of millet, oats, radishes, cucumbers and shiritsa. The prototype does not have an inhibitory effect. Wheat and barley in the experiment are selective crops.

 Example 7

 New compounds were tested on barley, wheat, corn, rye to increase seed germination, increase plant biomass by pre-sowing seed treatment at a flow rate of 20-80 g / m seeds and a working solution of 10 l / m. Treated seeds were sown in vegetation vessels with a diameter of 25 cm. Performance accounting was carried out 30 days after sowing seeds. The results are shown in table. 3.

 The data obtained indicate that in small doses, the use of new compounds can stimulate seed germination, increase plant growth rates.

 Example 8

 In the vegetation vessels filled with soil with a diameter of 30 cm, the seeds of wild radish, shiritsa, mari, millet of chicken, mice, tar, bristles, rye, barley, wheat, and corn were laid out. Each species was laid out in a separate vessel. The repetition of each option is fourfold. Simultaneously with sowing, new compounds were introduced into each vessel in a dose of 1.0-1.5 kg / ha. The seeds were covered with a layer of earth. Accounting for effectiveness was determined after 30 days from the day of sowing. The results are shown in table. 4. Data indicate that the new compounds exhibit decent inhibitory activity against weeds (radish, shiritsa, millet, mice, tar, bristles), while at the same time showing selectivity for crops (rye, barley, wheat, corn). Thus, biological tests showed that the new compounds exhibit growth-regulating activity. In small doses, drugs stimulate the growth process in plants. This is especially pronounced on cereals (rye, barley, wheat, corn). They cause an increase in seed germination, an increase in the length and mass of plants. In high herbicidal doses, the new compounds show a positive inhibitory effect on both single and dicotyledonous annual weeds. Compounds are undoubtedly of interest to agriculture.

Claims (1)

Azomethines 1,2,4-triazines of the general formula

where R is phenyl, n is chlorophenyl, furyl, butyl,
with growth regulating and herbicidal activities.

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