RU2654589C1 - Winter wheat and maize growth regulator - Google Patents

Abstract

FIELD: biotechnology; agriculture.

SUBSTANCE: invention relates to biotechnology and agriculture, in particular to a chemical agent that increases crop yields. 3-amino-4,5,6-trimethylthieno[2,3,6]pyridyl-2-carboxylic acid (furan-2-yl-methyl)-amide is proposed as a winter wheat and maize growth regulator. Compound increases the winter wheat yield by 3.9 c/ha and maize yield – by 6.9 c/ha.

EFFECT: crop yield is increased.

1 cl, 2 tbl, 4 ex

Description

The invention relates to chemicals that increase plant productivity, which is proposed 3-amino-4,5,6-trimethylthieno [2,3-b] pyridyl-2-carboxylic acid (furan-2-yl-methyl) -amide of the formula I:

Plant growth regulators are one of the most promising groups of pesticides, and it is no coincidence that every year it is replenished with new drugs. The advantage of growth regulators is that they have a significant effect on the growth and physiological processes occurring in the plant, allowing a person to control the development of the latter in the direction necessary for himself. The use of growth regulators provides, for example, the solution of such problems as increasing the yield and quality of cultivated products, increasing resistance to diseases and stressful situations and much more [Plant Protection and Quarantine - 2008. - No. 12. - S. 54].

The claimed compound has not been previously described in the literature, its growth-regulating properties are revealed for the first time.

The closest analogue to the claimed compound by properties (prototype) is the Bigus preparation, BP (potassium salts of humic acids, 20-25 g / l acid), which is used to increase productivity on winter wheat, corn and other crops ["State catalog of pesticides and agrochemicals approved for use on the territory of the Russian Federation. ” Ministry of Agriculture of Russia. Moscow. - 2016].

The closest analogue in structure is 2- [N- (2'-iodophenyl) carboxoamido] -3-amino-4,6-dimethylthieno [2,3-b] pyridine of formula II:

Compound II stimulates the germination of sunflower seeds [US Pat. RF, No. 2276845 dated 2006, Dmitrieva I.G., Dyadyuchenko L.V., Strelkov V.D., Isakova L.I., Krapivin G.D., Zaplynny V.N.].

The objective of the present invention is to expand the arsenal of biologically active substances obtained synthetically for use in agriculture as a plant growth regulator.

The technical result of the invention is to increase the yield of crops (winter wheat, corn).

This result is achieved using 3-amino-4,5,6-trimethylthieno [2,3-b] pyridyl-2-carboxylic acid (furan-2-yl-methyl) -amide of the formula I:

by treating vegetative plants of crops (winter wheat, corn).

The synthesis of the active substance is carried out by the authors in accordance with the scheme:

By the interaction of 4,6-dimethyl-3-cyano-2 (1H) -pyridinethione IV with N-furfuryl-2-chloroacetamide in the presence of the KOH equivalent in DMF solution, intermediate III was synthesized, which, without isolation from the reaction mixture, with the addition of an equimolar amount alkali is cyclized to the target compound I [Chem. farm. g. - 1992. - T. 26. - No. 11-12. - S. 62-66].

The starting 4,6-dimethyl-3-cyano-2 (1H) -pyridinethione IV was synthesized by a known method - the reaction of 4,5,6-trimethyl-2-chloro-nicotinonitrile with thiourea [Patent 2555450, Franse, application. 11/34/83; publ. 05.31.85].

Growth-regulating activity was determined according to the standard TsINAO methodology [Brief guidelines for conducting state tests of plant growth regulators. QINAO. Moscow - 1984 - p. twenty].

The invention is illustrated by the following examples.

Example 1. Synthesis of 3-amino-4,5,6-trimethylthieno [2,3-b] pyridyl-2-carboxylic acid (furan-2-yl-methyl) -amide (compound I).

To a suspension of 1.2 g (7.3 mmol) of 4,6-dimethyl-3-cyano-2 (1H) -pyridinethione IV in 25 ml of DMF, a solution of 0.41 g (7.3 mmol) of KOH is added in a minimal amount water and mix until the precipitate is completely dissolved. Then, a solution of 1.26 g (7.3 mmol) of N-furfuryl-2-chloroacetamide in 10 ml of DMF was added to the reaction mixture and stirred at room temperature for 30-40 minutes. After repeated addition of an aqueous solution of 0.41 g (7.3 mmol) KOH, stirring was continued for another 40 minutes, at the end, the reaction mixture was diluted with water twice and the precipitate formed was filtered off and dried. After recrystallization from ethanol, 1.63 g (77%) of the desired product I are obtained in the form of crystals with T _pl . 208-209 ° C.

Found,%: C 60.81; H 5.53; N, 13.45. C ₁₆ H ₁₇ N ₃ O ₂ S;

Calculated,%: C 60.94; H 5.44; N, 13.33.

¹ H NMR spectrum, δ, ppm (group): 2.25 (s, 3H, 5-CH ₃ ); 2.50 (s, 3H, 6-CH ₃ ); 2.65 (s, 3H, 4-CH ₃ ); 4.42 (d, 2H, CH ₂ ); 5.25, 6.35, 7.54 (m, 3H, Fu); 6.84 (br s, 2H, NH ₂ ); 8.05 (br s, 1H, NH).

Example 2. Synthesis of 2- [N- (2'-iodophenyl) carboxoamido] -3-amino-4,6-dimethylthieno [2,3-b] pyridine (compound II, prototype in structure)

To a suspension of 0.72 g (4.4 mmol) of 3-cyano-4,6-dimethyl-1 (H) -pyridinethione-2 in 15 ml of DMF, a solution of 0.25 g (4.4 mmol) is added with stirring at room temperature ) KOH dissolved in a min amount of water is stirred until the precipitate is completely dissolved and a solution of 1.3 g (4.4 mmol) of N- (2-iodophenyl) chloroacetic acid amide in 5 ml of DMF is added. Stirring is continued at the same temperature for another 1 hour, then a solution of 0.25 g (4.4 mmol) of KOH in min of water is added to the reaction mixture and stirred for another 40 minutes. The reaction mixture was diluted with 50 ml of water, the precipitate formed was filtered off, washed with water and dried. After recrystallization from DMF, 1.2 g (67%) of the expected product are obtained in the form of a white, fine-crystalline powder with T _pl . 242-244 ° C.

Found,%: C 45.66; H 3.51; N, 9.80. C ₁₆ H ₁₄ IN ₃ OS;

Calculated,%: C 45.40; H 3.34; N, 9.93.

¹ H NMR spectrum, δ, ppm (group): 2.52 (3H, s, 6-CH ₃ Py); 2.75 (3H, s, 4-CH ₃ Py); 6.88 (2H, br s, NH ₂ ); 7.09 (1H, m, 5-H Py); 7.30-7.91 (4H, m, Ar-H); 8.99 (1H, br s, NH).

Example 3. Evaluation of compound I and prototypes for growth-regulating activity on winter wheat plants in a field experiment.

Assessment of the growth-regulating activity of the claimed compound on winter wheat plants of the Kalym variety was carried out in the experimental field of VNIBZR. Winter wheat plants were treated with an aqueous solution of the synthesized compound twice — in the tillering phase (dose of 30 g / ha) and in the flag leaf phase (dose of 30 g / ha). The prototype in structure (compound II) was used similarly, Bigus solution, BP (prototype for use) was applied in the same phases (dose of 250 ml / ha) with a working fluid flow rate of 300 l / ha.

Spraying was carried out using an OEMP-16 sprayer. The experimental plot area is 5.6 m ² , the repetition is 4-fold, the allocation of plots is consistent. Wheat harvesting was carried out during the period of full ripening of grain.

Growth-regulating activity was determined by increasing the grain yield of plants processed by the proposed method and by the reference method, in comparison with the control (untreated plants). The accounting data was subjected to statistical processing using NDS ₀₅ [B.A. Armor. Methodology of field experience. - M: Kolos. - 1979. - S. 294-303]. The data obtained are presented in table 1.

NDS ₀₅ = 0.91

Thus, tests conducted on winter wheat, it was found that the claimed 3-amino-4,5,6-trimethylthieno [2,3-b] pyridyl-2-carboxylic acid (furan-2-yl-methyl) -amide when applied twice at a dose of 30 g / ha, it exhibits the properties of a growth promoter; it provided a significant and reliable increase in the yield of winter wheat grains in comparison with the control and prototypes. Compound I increased the yield of winter wheat by 3.9 kg / ha, which is 9.6% in relation to the control. In this case, compound II (prototype in structure) contributed to an increase in productivity by 2.9 kg / ha (7.1%), Bigus, BP - by 2.5 kg / ha (6.1%).

Example 4. Evaluation of compound I and prototypes for growth-regulating activity on corn plants in a field experiment.

The growth-regulating activity of the claimed compound I was also studied on maize under the conditions of a small-field field experiment according to the generally accepted TsINAO technique. For this, the corn plants of the Krasnodar 370MV variety were treated with a solution of compound I twice - in the phase of 2-4 leaves (dose 30 g / ha) and in the phase of 5-6 leaves (dose 30 g / ha). The prototype in structure (compound II) was used similarly, Bigus solution, BP was applied in the same phases (dose 300 ml / ha) with a working fluid flow rate of 300 l / ha.

The area of the experimental plot is 5.6 m ² with a fourfold repetition of experiments. Harvesting and assessment of the crop was carried out during the period of complete ripening of seeds.

Growth-regulating activity was determined by increasing the yield of corn seeds treated with the claimed compound or prototype, in comparison with the control (untreated plants). The accounting data was subjected to statistical processing using NDS ₀₅ . The data obtained are shown in table 2.

NDS ₀₅ = 2.13

As follows from table 2, the treatment of corn plants with 3-amino-4,5,6-trimethylthieno [2,3-b] pyridyl-2-carboxylic acid (furan-2-yl-methyl) -amide I has an advantage over prototypes, providing a yield increase of 6.9 kg / ha, which is 9.0%, while compound II contributes to a yield increase of 3.1 kg / ha (4.0%), and Bigus, BP - by 4 , 2 kg / ha (5.5%).

Thus, the invention realizes the indicated purpose: the claimed 3-amino-4,5,6-trimethylthieno [2,3-b] pyridyl-2-carboxylic acid (furan-2-yl-methyl) -amide I exhibits the properties of a growth regulator plants, significantly increasing the yield of winter wheat and corn.

Claims (3)

The use of 3-amino-4,5,6-trimethylthieno [2,3-b] pyridyl-2-carboxylic acid (furan-2-yl-methyl) -amide of the formula I:

as a regulator of the growth of winter wheat and corn.