RU2495569C1 - Method of increasing rice yield - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: invention relates to agriculture. Presowing treatment of rice seeds is carried out with 4-[4-(tert-butyl)phenyl sulphanyl]-6-methyl-1,3-dihydrofuro [3,4-c]pyridin-3-none, which has growth-regulating activity in a dose of 0.1-0.3 g/t seeds with working liquid consumption of 10 l/t seeds.

EFFECT: invention increases rice yield.

2 tbl, 3 ex

Description

The invention relates to agriculture and can be used in growing rice.

The use of plant growth regulators along with the use of fertilizers, chemical and biological plant protection products is one of the most promising ways to increase crop productivity.

As a prototype, the well-known growth regulator furolan at a dose of 0.427 ml / t of seeds (density 989 g / l) was selected during pre-sowing treatment, the rate of flow of working fluid was 10 l / t (List of pesticides and agrochemicals. Appendix to the journal "Plant Protection and Quarantine" No. 6, 2010).

As the claimed growth regulator to increase the yield of rice used 4- [4- (tert-butyl) phenylsulfanyl] -6-methyl-1,3-dihydro-furo [3,4-c] pyridin-3-one of the formula:

The claimed compound is known earlier (Izv. Akademii Nauk. Ser. Khimich. - 1994. - No. 12. - P.2215), however, its growth-regulating properties, allowing to increase the yield of rice, were revealed for the first time. The compound is used for pre-sowing treatment of rice seeds, respectively, at a dose of 0.1-0.3 g / t of seeds with a working fluid flow rate of 10 l / t of seeds.

The synthesis of compounds 4- [4- (tert-butyl) phenylsulfanyl] -6-methyl-1,3-dihydrofuro [3,4-c] pyridin-3-one was carried out electrochemically by thioalkylation of 2-chloro-1,2-dihydro-3 -pyridinecarbonitrile 4-tert-butylthio-phenol according to the scheme:

The technical result is to increase rice yield by pre-sowing treatment of rice seeds with 4- [4- (tert-butyl) phenylsulfanyl] -6-methyl-1,3-dihydrofuro [3,4-c] pyridin-3-one of the formula I, which exhibits growth-regulating properties.

The technical result is achieved by the fact that in the method of increasing the yield of rice, including pre-sowing seed treatment with a growth regulator at a rate of flow of working fluid of 10 l / t of seeds, according to the invention, 4- [4- (tert-butyl) phenyl sulfanyl] is used as a growth regulator -6-methyl-1,3-dihydrofuro [3,4-c] pyridin-3-one at a dose of 0.1-0.3 g / t of seeds.

The invention is illustrated by the following examples.

Example 1

4- [4- (tert-butyl) phenylsulfanyl] -6-methyl-1,3-dihydrofuro [3,4-c] pyridin-3-one (compound I)

60 ml of a 0.3N Et ₄ NBr solution in absolute acetonitrile containing a mixture of 1.66 g (0.01 mol) of 4-tert-butylthiophenol and 1.84 g of 6-methyl-4-chloro-1 are placed in the cathode compartment of the cell with a glass diaphragm , 3-dihydrofuro [3,4-c] pyridin-3-one (0.01 mol). Anolyte - 50 ml of background solution. The cathode is a plate of Pt (35 cm ³ ). The anode is an Mg rod with a diameter of 1 cm. The electrolysis is carried out in an argon atmosphere at 20-25 ° C in the galvanostatic mode at a current density of 3-5 mA · cm ^-2 . The catholyte is stirred using a magnetic stirrer. After passing 1.05-1.10 F · mol ^{-1 of} electricity, the catholyte is drained and the solvent is distilled off in vacuo. The residue is treated with water, extracted with CH ₂ Cl ₂ , dried with MgSO ₄ . The solvent was evaporated in vacuo, the obtained product was extracted with cold hexane and then hot hexane to purify disulfide impurities. The residue was recrystallized from a mixture of acetone and hexane. Yield 2.29 g (73%).

Elemental analysis: Found: C, 68.89; H, 6.00; N, 4.38. C ₁₈ H ₁₉ NO ₂ S. Calculated: C 68.98; H, 6.11; N, 4.47. _Mp 181-182 ° C.

IR spectrum: v, cm ^-1 (liquid paraffin): 3015.2070 (C-H _Ar ); 1105, 1070, 1020 (C-O-C); 1750, 1740 (C = O).

¹ H NMR spectrum (CDCl ₃ ): 1.30 (s, 9H, C (CH ₃ ) ₃ ) 2.37 (3H, s, CH ₃ -Py); 5.15 (2H, s, CH ₂ O); 6.85 (1H, s, H-Ru); 7.81 (s, 4H, C ₆ H ₄ ).

Example 2

Initial evaluation of the growth-regulating activity of compounds I, II

The growth-regulating activity of 6-methyl-4 - [(4-tert-butyl) phenylthio] -furo [3,4-c] pyridin-3 (1H) -one was determined by model laboratory screening experiments on Liman rice seeds. In the course of laboratory screening, the optimal growth-activating concentration of the compound, its effect on the sowing quality of seeds, the growth of seedlings, and the accumulation of dry mass in them were determined. As a control, seeds treated with water were used.

The compound was used in the form of aqueous solutions with concentrations of 0.1; 0.01; 0.005; 0.001 and 0.0005 wt.%. Rice seeds were soaked in solutions of these compounds and in water (control). The exposure of the treatment is 1 hour. After the treatment, the seeds were laid out in 100 pieces per Petri dish on filter paper saturated with water. Then the seeds were placed in a thermostat for germination at a temperature of 25 ° C. Germination energy was determined on the 4th day, germination - on the 7th day. To establish the effect of the compounds on the intensity of seed germination, the length of roots and sprouts and their dry weight per 100 seedlings were determined. The repetition in the experiment is fourfold.

The results of the laboratory experiment are shown in table 1.

4- [4- (tert-butyl) phenylsulfanyl] -6-methyl-1,3-dihydrofuro [3,4-c] pyridin-3-one in an optimal concentration of 0.0005 wt.% Increases the seed germination energy by 5, 2%, germination - by 4.3%, root length - by 15.0%, sprout - by 15.4%, dry matter mass of the root - by 33.3%, sprout - by 44.4% in comparison with the control .

Example 3

Assessment of growth-regulating activity in the conditions of the field small-plot experiment

The growth-regulating activity of the claimed compounds was determined under the conditions of a small-plot field experiment using the TsINAO method.

Rice seeds before sowing were treated with drug solutions. Control - seeds treated with water.

4- [4- (tert-butyl) phenylsulfanyl] -6-methyl-1,3-dihydrofuro [3,4-c] pyridin-3-one is used for presowing treatment of rice seeds in doses of 0.1, 0.2, respectively and 0.3 g / t of seeds at a flow rate of 10 l / t. Furolan prototype - at a dose of 0.427 ml / t of seeds (density 989 g / l) during pre-sowing treatment, the working fluid flow rate is 10 l / t.

The experimental plot area is 20 m ² , the experiment is repeated four times. Harvesting was carried out during the period of full maturity. Growth-regulating activity was determined by increasing the grain yield in the processing options of the claimed compound, the prototype furolan in comparison with the control. The test results are presented in table 2.

As follows from table 2, pre-sowing treatment of rice seeds 4- [4- (tert-butyl) phenylsulfanyl] -6-methyl-1,3-dihydrofuro [3,4-c] pyridin-3-one has an advantage over the prototype , providing an increase in the yield of rice by 7.9 kg / ha (+ 13.2%), while the prototype - furolan helps increase yields by 4.8 kg / ha (+ 8% to control).

table 2 The influence of growth regulators on the yield of rice of the Liman variety (with a working fluid consumption rate of 10 l / t rice seeds) A drug Dose g / t seeds Productivity c / ha Increase in control c / ha % the control - 59.7 - - 4- [4- (tert-butyl) phenyl-sulfanyl] -6-methyl-1,3-dihydrofuro [3,4-c] pyridin-3-one 0,100 64.6 4.9 8.2 0,200 67.6 7.9 13,2 0,300 65.1 5,4 9.0 furolan 0.422 64.5 4.8 8.0 NDS ₀₅ 2.7

The proposed method allows to increase the yield of rice.

Claims (1)

A method of increasing rice yield, including presowing treatment of rice seeds with a regulator at a rate of working fluid consumption of 10 l / t of seeds, characterized in that 4- [4- (tert-butyl) phenylsulfanyl] -6-methyl-1 is used as a growth regulator, 3-dihydrofuro [3,4-c] pyridin-3-one at a dose of 0.1-0.3 g / t of seeds.