RU2338748C1 - 3-AMINO-4,5,6-TRIMETHYL-2-(BENZIMIDAZOLYL-2(TIENO[2,3-b]PYRIDINE AS SUGAR BEET GROWTH REGULATOR - Google Patents

Abstract

FIELD: agriculture.

SUBSTANCE: new chemically biologically active compound 3-amino-4,5,6-trimethyl-2-(benzimidazolyl-2)tieno[2,3-b]pyridine of formula 1

revealing growth regulating properties is described.

EFFECT: increasing sugar beet crop yield and sugar content.

1 tbl, 3 ex

Description

The invention relates to a new chemical biologically active substance from a number of heterocyclic compounds of the formula 1:

showing growth-regulating properties on sugar beet plants.

The closest analogs in structure to the claimed compound may include 2- [N- (2-iodophenyl) carboxoamido] -3-amino-4,6-dimethylthieno [2,3-b] pyridine structure:

known as a regulator of the growth of sunflower plants [RF Patent No. 2276845 of 05.27.2006, Dmitrieva IG, Dyadyuchenko LV, Strelkov VD, Isakova LI, Krapivin GD, Zaplichny V. N. “Use of 2- [N- (2'-iodophenyl) carboxoamido] -3-amino-4,6-dimethylthieno [2,3-b] pyridine as a stimulator of germination of sunflower seeds”].

As an analogue in properties, the preparation of humic acids is known as potassium salts - Bigus, BP (20-25 g / l in acid) of NTO Agroecologiya CJSC, which is used to increase yield on sugar beets [List of pesticides and agrochemicals allowed for use on the territory RF 2004. No. 5, p. 311-313].

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

This is achieved by using 3-amino-4,5,6-trimethyl-2- (benzimidazolyl-2) thieno [2,3-b] pyridine 1 by spraying sugar beet plants.

The growth-regulating properties of the claimed compounds are revealed for the first time.

In this case, the inventive thienopyridine 1 is obtained by a known two-stage method - the interaction of 3-cyano-4,5,6-trimethyl-2- (1H) pyridine-thione with an equimolar amount of KOH and 2-bromobenzimidazole at a temperature of 20-25 ° C followed by cyclization [ cm. Synthesis of substituted 2-alkyl (aryl) thio-3-cyanopyridines and 3-aminothieno [2,3-b] pyridines / E.A. Kaygorodova, L.D. Konyushkin, S.N. Mykhaylichenko. V.K. Vasilin, G. Kulnevich // -HGS, 1996, No. 10, p. 1432-1437]. The starting 3-cyano-4,5,6-trimethyl-2 (1H) -pyridinethione is obtained and purified by a known method [Weigand-Hilgetag. Experimental methods in organic chemistry. - M .: Chemistry, 1969. p. 581-582].

Growth-regulating activity was determined according to the standard method [Brief guidelines for conducting state tests of plant growth regulators. QINAO. Moscow - 1984. P.20].

The invention is illustrated by the following examples:

Example 1. 3-amino-4,5,6-trimethyl-2- (benzimdazolyl-2) thieno [2,3-b] pyridine (compound 1).

To a suspension of 1.2 g (7 mmol) of 4,5,6-trimethyl-3-cyano-2 (1H) -pyridine-thione in 15 ml of DMF was added a solution of 0.4 g (7 mmol) of KOH in a minimum amount of water and mix until the precipitate is completely dissolved. Then a solution of 1.38 g (7 mmol) of 2-bromobenzimidazole in 5 ml of DMF is added and stirring is continued for another 40 minutes. Without isolating the product, the equivalent of KOH dissolved in a minimum amount of water is introduced into the reaction mass, and mixed for 50 minutes. The reaction mass is diluted with water twice, the precipitate is filtered off, dried. After recrystallization from ethanol, 1.6 g (81%) of the expected product are obtained with mp. 184-185 ° C.

Found,%: C 66.63; H 5.07; N, 18.44; C ₁₇ H ₁₆ N ₄ S;

Calculated,%: C 66.21; H 5.23; N, 18.17.

NMR ¹ H, δ, ppm (group): 2.22 (3H, s, 6-CH ₃ Ru); 2.29 (3H, s, 5-CH ₃ Ru); 2.43 (3H, s, 4-CH ₃ Ru); 5.69 (2H, br s, NH ₂ ); 7.38 ... 7.45 (4H, m, Ar); 9.71 (1H, s, NH of pyrazole).

Example 2. 2- [N- (2-iodophenyl) carboxoamido] -3-amino-4,6-dimethylthieno [2,3-b] pyridine (compound 2).

To a suspension of 0.72 g (4.4 mmol) of 4,6-dimethyl-3-cyano-2 (1H) -pyridine-thione in 12 ml of DMF is added a solution of 0.25 g (4.4 mmol) of KOH in a minimum amount water and mix until the precipitate is completely dissolved. Then a solution of 1.3 g (4.4 mmol) of N- (2-iodophenyl) amide of chloroacetic acid in 5 ml of DMF is poured and stirring is continued for 1 more hour. Without isolating the product, 0.25 g (4.4 mmol) KOH, dissolved in a minimum amount of water, is stirred for 1 h. The reaction mass is diluted with water twice, the precipitate is filtered off and dried. After recrystallization from DMF, 1.2 g (67%) of the expected product are obtained with mp. 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, 9.83.

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

Example 3. Evaluation of the growth-regulating activity of the claimed compounds on sugar beet plants.

Druzhba - MS 34 varieties of sugar beets were sprayed twice in the phase of 6-8 leaves and when closed in rows [Brief guidelines for conducting state tests of plant growth regulators. QINAO. Moscow - 1984. P.20].

The flow rate of the working fluid is 250 l / ha. Working solutions were prepared in tap water (pH = 6.8) with the addition of OP-7 (0.1%).

Spraying was carried out using a backpack sprayer. The experimental plot area is 5.6 m ² , 4-fold repetition, the allocation of the plots is randomized.

At the end of the growing season, root crops were recorded and the sugar content was determined. The mass of root crops from the plot was weighed on a commodity balance, the sugar content was determined refractometrically (IRF-22) [A.V. Peterburgsky. Workshop on agronomic chemistry. State Publishing House of Agricultural Literature, 1959. p.192-197]. The accounting data was subjected to statistical processing using NDS ₀₅ [B.A. Dospekhov. Methodology of field experience. - M: Kolos, 1979. S.294-303].

The data obtained are presented in the table.

Tests conducted on sugar beets, it was found that the claimed compound 1 at a dose of 28-40 g / ha exhibits the properties of a growth stimulant.

Compound 1 at a dose of 28 g / ha increased the yield of root crops by

3.9 t / ha and increased sugar content by 1.5% relative to the control, at a dose of 40 g / ha, the root crop increased by 5.3 t / ha, and sugar content by 2.2%.

The structural analogue of compound 2 in doses of 28-40 g / ha did not exhibit growth-regulating properties.

Thus, 3-amino-4,5,6-trimethyl-2- (benzimidazolyl-2) thieno [2,3-b] pyridine (compound 1) stimulate the growth of sugar beet plants, increase its sugar content and exceed the analogue in properties Bigus, BP and an analogue in structure of compound 2.

Table
Growth-regulating activity of compounds 1-2 and the preparation "Bigus, BP" on sugar beet cultivar Druzhba MS-34. Preparations Dose g / ha Root crop productivity, t / ha The increase to the control, t / ha Sugar content,% Sugar harvest, t / ha The control - 34.2 - 21.8 7.45 Compound 1 28 38.1 3.9 23.3 8.49 40 35.9 5.3 24.0 9.48 Compound 2 28 34.5 0.3 22.0 7.59 40 34.2 0 21.0 7.18 Bigus, BP 300 l / ha 37.5 3.3 22.5 8.43 NDS ₀₅ = 1.65

Claims (1)

3-amino-4,5,6-trimethyl-2- (benzimidazolyl-2) thieno [2,3-b] pyridine of the formula 1:

as a growth regulator of sugar beet plants.