RU2146252C1 - 1,2,4-triazinone-5 azomethines having growth regulating activity - Google Patents

Abstract

FIELD: agriculture. SUBSTANCE: described are new 3-azomethino-6-methyl-1,2,4-triazinones-5 of general formula:

Description

 The invention relates to the field of chemistry of heterocyclic compounds, namely, derivatives of 1,2,4-triazinones-5, with growth-regulating activity, and which can be used in agriculture.

где R¹ = -NHNH₂; NHC(S)NHCH₂CH=CH₂;
R² = -H, -NH₂;
R³ = -C₆H₅, C₆H₅CH₂,
обладающие рострегулирующей активностью. Недостатком данных соединений является органическая селективность.Close in structure (prototype) are 1,2,4-triazinones-5 [publ. application N 93019283/04, cl. C 07 D 253/075, 1993 / BI N 6, 1996] of the general formula

where R ¹ = —NHNH ₂ ; NHC (S) NHCH ₂ CH = CH ₂ ;
R ² = -H, -NH ₂ ;
R ³ = —C ₆ H ₅ , C ₆ H ₅ CH ₂ ,
with growth regulating activity. The disadvantage of these compounds is organic 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 = phenyl, n-chlorophenyl, furyl, butyl.

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

Example 1. 3-Phenylazomethino-6-methyl-1,2,4-triazinon-5
In a three-necked flask equipped with a mechanical stirrer, with a Dean-Stark trap and a thermometer, 1.26 g (0.01 mol) of 3-amino-6-methyl-1,2,4-triazinone-5, 40 ml of toluene, 0 99 g (0.0093 mol) of benzaldehyde; and 0.0225 g (0.0001 mol) of n-toluenesulfonic acid. The reaction mixture was boiled until water evolution ceased, cooled. The product was washed with toluene, dried. 1.85 g (93%) of 3-phenylazomethino-6-methyl-1,2,4-triazinone-5 were obtained.

Mp 278 ^° C (decomp.).

 UV spectrum (nm) 336.

IR spectrum (cm ^-1 ) 1600-1650, 1680, 1590.

 Mass spectrum (m / e) 214, 186, 1586, 28.

Elemental analysis (%):
Found: 26.6 N.

 Calculated: 26.2 N.

 Example 2

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

Yield 89%, T. pl. 266 ^o C (decomp.).

 UV spectrum (nm) 336.

IR (cm ^-1 ) 1600-1650, 1680, 1590, 750.

 Mass spectrum (m / e) 248.5; 220.5; 192.5; 28.

Elemental analysis (%):
Found: 22.5 N; 13.9 Cl.

 Calculated: 22.1 N; 14.3 Cl.

 Example 3

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

Yield 91%, mp. 139 ^o C (decomp.).

 UV spectrum (nm) 336.

IR spectrum (cm ^-1 ) 1600-1650, 1680, 1590, 1160.

 Mass spectrum (m / e) 204, 176, 148, 28.

Elemental analysis (%):
Found: 27.1 N; 7.4 O.

 Calculated: 27.5 N; 7.8 O.

 Example 4

 Under similar conditions, 3-butylazomethino-6-methyl-1,2,4-triazinon-5 was obtained from 3-amino-6-methyl-1,2,4-triazinone-5 and valerian aldehyde.

Yield 95%, mp. 176 ^o C.

 UV spectrum (nm) 336.

IR spectrum (cm ^-1 ) 1600-1650, 1680, 1590.

 Mass spectrum (m / e) 194, 166, 138, 28.

Elemental analysis (%):
Found: 28.5 N.

 Calculated: 28.9 N.

 Example 5. Determination of biological activity.

The express method in laboratory conditions determined the biological activity of new compounds. For this, the sprouted seeds of barley, wheat, cucumbers, sunflowers, peas (seedlings 2-3 mm long) were laid out on a layer of filter paper in Petri dishes and 4 ml of the drug solution were poured at a concentration of 1-10-50-100 mg / l. Then the Petri dishes were placed in a thermostat at a temperature of 26 ^o C for four days. After this period, measurements were made of the length and mass of the experimental and control samples. The repetition for each option is 4-fold. In the control version, distilled water was used.

 The results of laboratory tests are given in table. 1. The data show that the new compounds exhibit a positive growth-regulating effect, which affects the increase in the length (L) and mass (m) of the seedlings in comparison with the control. The degree of activity of the new compounds are not inferior to the taken prototype.

 Example 6. The activity of new compounds in vegetation experiments.

 The seeds of wheat, peas, and sunflower were soaked for 12 hours in a solution of the test compounds: the concentration of the working solution of the preparations was 1-10 mg / l. Then, the treated seeds were sown in vegetation vessels with a diameter of 25 cm, filled with soil. The repetition of each option is 4-fold. The effectiveness of the compounds was determined after 30 days from the day of sowing seeds. The results of vegetation experiments are given in table. 2. The data obtained show that the effectiveness of the new compounds significantly exceed the control options and are not inferior to the prototype. The inventive compounds stimulate germination, seed germination energy, increase the length and mass of plants.

 Example 7. Vegetative testing of new compounds.

 New compounds were tested on corn to increase seed germination and increase green mass of the plant by pre-sowing seed treatment at a flow rate of 25-15 g / m of seeds and a working solution of 10 l / m. The seeds treated one week before sowing were sown in vegetation vessels with a diameter of 25 cm. Efficiency analysis was carried out 30 days after sowing seeds. The test results are given in table. 3. The data obtained confirm the results of 5 and 6 examples.

 Thus, the new derivatives of 6-methyl-1,2,4-triazinone-5 have positive growth-regulating activity and can be recommended for agricultural practice to identify germination and germination energy of seeds and crops.

Claims (1)

Azomethines 1,2,4-triazines-5 of the general formula

where R = phenyl, n is chlorophenyl, furyl, butyl,
with growth-regulating and herbicidal activity.

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