RU2497359C1 - Method of increasing yield of grain crops - Google Patents

Abstract

FIELD: agriculture.

SUBSTANCE: invention relates to agriculture. The presowing treatment of cereal seeds is carried out with 6-methyl-4-(2-pyridylsulfanil)-1,3-dihidrofuror-3,4-c]pyridin-3, exhibiting growth-regulating activity in a dose of 0.2-0.6 g/t of seeds at a consumption rate of operating fluid 10 l/t of seeds.

EFFECT: invention enables to improve productivity.

6 tbl, 7 ex

Description

The invention relates to agriculture and can be used for growing crops.

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.

Known growth regulators were selected as prototypes: on rice, furolan at a dose of 0.427 ml / t of seeds (active substance content of 989 g / l), on winter wheat and corn - carvitol (active substance content of 10 g / l) at a dose of 25 ml / t during pre-sowing seed treatment, the working fluid flow rate is 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 cereals - rice, winter wheat, corn used 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [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, which allow to increase the yield of grain crops, were revealed for the first time. The compound is used for pre-sowing treatment of seeds of rice, corn and winter wheat at a dose of 0.2-0.6 g / t of seeds at a rate of flow of working fluid of 10 l / t.

The synthesis of 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one was carried out electrochemically by thioalkylation of 2-chloro-1,2-dihydro-3-pyridinecarbonitrile with 2-pyridinethiol according to scheme:

The technical result is to increase the yield of crops (rice, winter wheat, corn) by pre-sowing seed treatment of 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one, exhibiting growth regulating properties.

The technical result is achieved by the fact that in the method of increasing the yield of grain crops (rice, winter wheat, corn), 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, 6-methyl-4 is used as a growth regulator - (2-pyridyl-sulfanyl) -1,3-dihydrofuro- [3,4-c] pyridin-3-one at a dose of 0.2-0.6 g / t of seeds.

The invention is illustrated by the following examples.

Example 1

6-Methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one.

60 ml of a 0.3N Et ₄ NBr solution in absolute acetonitrile containing a mixture of 1.11 g (0.01 mol) of 2-pyridinethiol and 1.84 g of 6-methyl-4-chloro-1 are placed in the cathode compartment of a 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. The product was further purified by silica gel column chromatography. The eluent is hexane-acetone (5-6: 1). Yield 1.78 g (69%).

Elemental analysis: Found: C, 60.32; H 3.79; N, 10.75. C ₁₃ H ₁₀ N ₂ O ₂ S. Calculated: C 60.45; H 3.90; N, 10.85. T _pl. 178-179 ° C.

IR spectrum: ν, cm ^-1 (liquid paraffin): 3075.3035 (С-H _Ar ); 1100, 1080, 1025 (C-O-C); 1730 (C = O).

¹ H NMR Spectrum (CDCl ₃ ): 2.40 (3H, s, CH ₃ -Py); 5.17 (2H, s, CH ₂ O); 6.80-7.50 (m, 3H, N-Ru '); 6.97 (1H, s, H-Ru), 8.54 (dd, 1H, 6-H-Ru ', J = 4.9; J = 1.3).

Example 2

Initial assessment of the growth-regulating activity of 6-methyl-4- (pyridin-2-ylthio) furo [3,4-c] pyridin-3 (1H) -one.

The growth-regulating activity of 6-methyl-4- (pyridin-2-ylthio) furo [3,4-c] pyridin-3 (1H) -one was determined by model laboratory screening experiments on Liman rice seeds. During 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.

6-Methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one in an optimal concentration of 0.001 wt.% Increases the germination energy by 3.0%, germination - 3.0 %%, root length - 15.0%, sprout - 15.4%, dry matter mass of the root - 27.8%, sprout - 38.9% in comparison with the control.

Example 3

Assessment of the growth-regulating activity of 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one under the conditions of a shallow field experiment on rice seeds.

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

Before sowing rice seeds were treated with a solution of the drug. Control - seeds treated with water.

6-Methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one is used for presowing treatment of rice seeds in doses of 0.2, 04 and 0.6 g / t, respectively seeds at a flow rate of 10 l / t. Furolan prototype - at a dose of 0.427 ml / t of seeds 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 was 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 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one has an advantage over the prototype, providing an increase in grain yield crops - rice, respectively, 7.5 kg / ha (+ 12.6% to

Table 1 The effect of 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one on the sowing qualities of rice seeds of the Liman variety Concentration,
mass fraction,% Energy
germination% Germination,% Length cm Dry weight, g / 100,
seedlings A drug root sprout the roots sprouts the control 92.0 94.0 4.0 1.3 0.18 0.18 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one 0.01 90.0 92.0 3.6 1.3 0.16 0.20 0.005 92.0 94.0 4.1 1.4 0.18 0.24 0.001 94.8 96.8 4.6 1,5 0.23 0.25 0,0005 92.8 94.8 4.4 1.4 0.19 0.24 NDS 2.9 2.9 0.1 0.05 0.01 0.01

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) Dose g / t seeds Productivity c / ha Increase in control A drug c / ha % the control - 59.7 - - 6-methyl-4- (2-pyridylsulfanil) -1,3-dihydrofuro- [3,4-c] pyridin-3-one 0,200 64,4 4.7 7.9 0.400 67.2 7.5 12.6 0,600 65.5 5.8 9.7 furolan 0.422 64.5 4.8 8.0 NDS ₀₅ 2.7

control), while the prototype - furolan helps to increase productivity by 4.8 c / ha (+ 8.0% of the control).

Example 4

Initial assessment of the growth-regulating activity of 6-methyl-4- (pyridin-2-ylthio) furo [3,4-c] pyridin-3 (1H) -one on winter wheat seeds.

The growth-regulating activity of 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-C] pyridin-3-one was determined by model experiments of laboratory screening on winter wheat seeds of the Irishka variety. During laboratory screening, we determined the optimal growth-activating concentration of the compound, its effect on the sowing quality of seeds (germination energy, germination, seed germination rate - the length of roots and sprouts and their mass). As a control, seeds treated with water were used. The compounds were used in the form of aqueous solutions with concentrations of 0.01, 0.005, 0.001 and 0.0005 wt.%. Exposure processing 1 hour. After processing, the seeds were laid out in 100 Petri dishes on filter paper saturated with water. Then the Petri dishes were placed in a thermostat for germination of seeds at a temperature of 25 ° C. Germination energy was determined on the 3rd day, germination - on the 7th day.

To establish the effect of the compound on the intensity of seed germination during the elimination of the experiment, we determined the length of the roots and sprouts, their mass (wet, dry) per 100 pcs. seedlings. The repetition of the experiment is fourfold.

The results of laboratory experiments are shown in table 3.

The compound 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one in an optimal concentration of 0.001 wt.% Increases the germination energy by 3.5%, germination - by 4 , 5%, spine length - by 14.5, sprouts - by 12.7; wet weight of roots — by 25.3, dry weight of roots by 15.7, wet and dry mass of sprouts — by 22.4 and 12.5%, respectively, in comparison with the control.

Example 5

Assessment of the growth-regulating activity of 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one under the conditions of a small-field experiment on wheat seeds.

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

Before sowing winter wheat seeds were treated with a solution of the drug. Control - seeds treated with water.

6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one is used for presowing treatment of winter wheat seeds in doses of 0.2, 0.4 and 0.6 g / t of seeds at a flow rate of 10 l / t. Prototype carvitol - at a dose of 25 ml / t of seeds during pre-sowing treatment, the rate of flow of working fluid 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 was carvitol, in comparison with the control. The test results are presented in table 4.

Table 4 The effect of 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro- [3,4-C] pyridin-3-one on the yield of winter wheat of the Irishka variety A drug Dose, g / t of seeds Productivity, t / ha Increase in control c / ha % The control - 43.1 - - 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one 0,200 45.8 2.7 6.3 0.400 49.4 6.3 14.6 0,600 46.7 3.6 8.4 carvitol 0.422 47.2 4.1 9.5 NDS ₀₅ 1.8

As follows from table 4, pre-sowing treatment of seeds of winter wheat 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one has an advantage over the prototype, providing a yield increase winter wheat by 6.3 kg / ha (+ 14.6% to control), while the prototype helps to increase yield by 4.1 kg / ha (+9.5 to control).

Example 6

Initial assessment of the growth-regulating activity of 6-methyl-4- (pyridin-2-ylthio) furo [3,4-c] pyridin-3 (1H) -onan in maize seeds.

The growth-regulating activity of 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one was determined by model experiments of laboratory screening on maize seeds of the FAO 340 hybrid. During the laboratory screening, the optimal growth-activating the concentration of the compound, its effect on the sowing quality of seeds (germination energy, germination, seed germination intensity - the length of the roots and sprouts and their mass). As a control, seeds treated with water were used. The compounds were used in the form of aqueous solutions with concentrations of 0.01, 0.005, 0.001 and 0.0005 wt.%. Exposure processing 1 hour. After processing, the seeds were laid out in 100 Petri dishes on filter paper saturated with water. Then the Petri dishes were placed in a thermostat for germination of seeds at a temperature of 25 ° C. Germination energy was determined on the 4th and 7th day, respectively.

To establish the effect of the compound on the intensity of seed germination during the elimination of the experiment, we determined the length of the roots and sprouts, their mass (wet, dry) per 100 pcs. seedlings. The repetition of the experiment is fourfold. The laboratory results are shown in table 5. The compound 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one in an optimal concentration of 0.005 wt.% Increases the germination energy by 2.0%, germination - 1.5%, spine length - 30.8%, sprouts - 22.2%; the fresh weight of roots — by 21.3%, the dry weight — by 32.6%, the fresh weight of sprouts — by 17.9 dry weight — by 28.7% in comparison with the control.

Table 5 The effect of 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one on the sowing quality of maize seeds of the hybrid FAO 340 A drug Concentration, mass fraction,% Energy
germination% Germination,% Length cm Weight, g / 100 pcs. seedlings Raw Dry spine sprout rootlets sprouts rootlets sprouts the control - 98.0 98.5 7.8 4,5 10.81 11.98 1.41 1.22 6-methyl-4- (2-pyridylsulfa-nyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one 0.01 100.0 one hundred 9.8 5,0 11.83 13.45 1,69 1.29 0.005 100.0 one hundred 10,2 5.5 13.11 14.13 1.87 1,57 0.001 98.5 99.5 9.6 5,4 12.22 13.08 1.74 1.41 0,0005 97.0 99.0 9.3 5.2 11.34 12.61 1,63 1.24 NDS ₀₅ 0.3 0.2 0.41 0.46 0.06 0.05

Example 7

Assessment of the growth-regulating activity of 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one under the conditions of a small-field experiment on seeds of maize of the hybrid FAO 340

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

Before sowing corn seeds were treated with a solution of the drug. Control - seeds treated with water.

6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one is used for presowing treatment of corn seeds in doses of 0.2, 0.4 and 0.6 g, respectively / t of seeds at a rate of flow of working fluid of 10 l / t. Prototype carvitol - at a dose of 25 ml / t of seeds during pre-sowing treatment, the rate of flow of working fluid 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 treatment options of the claimed compound, the prototype was carvitol, in comparison with the control. The test results are presented in table 6.

Table 6 The effect of 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro- [3,4-c] pyridin-3-one on the corn yield (in grain) of the FAO hybrid 340 A drug Dose, g / t of seeds Productivity, t / ha Increase in control c / ha % The control - 51,2 - - 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one 0,200 56.9 5.7 11.1 0.400 59.3 8.1 15.8 0,600 55.8 4.6 9.0 Carvitol 0.422 54.0 2,8 5.5 NDS ₀₅ 2,5

As follows from table 6, pre-sowing treatment of corn seeds 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro [3,4-c] pyridin-3-one has an advantage over the prototype, providing an increase in the corn crop - by 8.1 c / ha (+ 15.8% to the control), while the prototype - carvitol contributes to an increase in productivity by 2.8 (+ 5.5% to the control).

Claims (1)

A method of increasing the yield of grain crops, including pre-sowing seed treatment with a growth regulator at a flow rate of 10 l / t of seeds, characterized in that 6-methyl-4- (2-pyridylsulfanyl) -1,3-dihydrofuro is used as a growth regulator [3 , 4-c] pyridin-3-one at a dose of 0.2-0.6 g / t of seeds