RU2156242C1 - 3,5-disubstituted 2,4-triazinones-6 having growth- regulating activity - Google Patents

Abstract

FIELD: agriculture. SUBSTANCE: described are 3,5-disubstituted 1,2,4-triazinones-6 of general formula I:

wherein R¹ is C₆H₅, C₆H₁₃;; R² is C₅H₁₁, C₆H₅CH₂ which have growth-regulating activity and are useful in agriculture for increasing the yield of crops. EFFECT: improved properties of the title compounds. 4 ex, 2 tbl

Description

 The invention relates to the field of chemistry of heterocyclic compounds, namely, derivatives of 1,2,4-triazinones-6, 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 этих 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. B.I. 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 R¹=C₆H₅, C₆H₁₃;
R² = C₅H₁₁, C₆H₅CH₂.The invention consists in the creation of new compounds of the heterocyclic series by the reaction:

where R ¹ = C ₆ H ₅ , C ₆ H ₁₃ ;
R ² = C ₅ H ₁₁ , C ₆ H ₅ CH ₂ .

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

 Example 1. 3-Hexyl-5-benzyl-1,2,4-triazinon-6.

In a conical flask, 2.2 g (0.008 M) of alpha-enantoylaminocinnamic acid hydrazide in 20 ml of a 4% NaOH solution were vigorously stirred at a temperature of 70 ^° C. After cooling, the reaction mixture was neutralized with concentrated hydrochloric acid to pH 2. The precipitate was filtered off, washed three times with cold water and dried.

1.5 g (69.1%) of 3-hexyl-5-phenyl-1,2,4-triazinone-6 were obtained; Mp. 128 ... 130 ^o C.

UV spectrum (nm) 305;
IR (cm ^-1 ) 2880, 1650;
Mass spectrum (m / z) 271, 242, 214, 111.

Elemental analysis (%):
Found: 15.8N;
Calculated: 15.5 N.

 Example 2. Similarly obtained 3-phenyl-5-amyl-1,2,4-triazinon-6.

Yield 73.2%; Mp 240 ... 242 ^o C;
UV spectrum (nm) 300;
IR (cm ^-1 ) 2875, 1640;
Mass spectrum (m / z) 243.214.103.77;
Elemental analysis (%):
Found: 17.5 N;
Calculated: 17.3 N.

Example 3. The sticky seeds of corn, cucumbers, radishes, wheat were laid on filters in Petri dishes and poured with solutions of new compounds. The working concentration of the solutions is 1 ... 10 mg / l. The repetition of each option is 4-fold. Then the Petri dishes were placed in a thermostat for 4 days at a temperature of 25 ^o C. After this period, the effectiveness of the compounds was determined in comparison with the control and the prototype according to the length (l), weight (m) of the seedlings. The test results are shown in table 1.

 The data in Table 1 show that the new 1,2,4-triazinones-6 have growth-regulating activity and increase the length and mass of seedlings. In terms of activity, they are not inferior to the taken prototype.

 Example 4. Seeds of corn, sunflower for 12 hours soaking in solutions of new compounds. The working concentration of solutions is 1 mg / l. Then, the treated seeds were sown in vegetation vessels with a diameter of 30 cm. The repetition of each option is 4-fold. The results of the experiment are given in table. 2. The above data indicate the effectiveness of new compounds, not inferior in effectiveness to the prototype. New substances stimulate germination, seed germination energy, increase plant biomass.

 Thus, the tests showed that the new derivatives of 1,2,4-triazinone-6 have growth-regulating activity and can be used in agricultural practice to increase crop yield.

Claims (1)

3,5-disubstituted 1,2,4-triazinones-6 of the general formula

where R ¹ -C ₆ H ₅ , C ₆ H ₁₃ ;
R ² -C ₅ H ₁₁ , C ₆ H ₅ CH ₂ ,
with growth regulating activity.

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