RU2726431C1 - (4,6-dimethyltriazolo[1,5-a]pyrimidyl-2-sulphanyl)-2-trifluoroacetanilide as maize growth regulator - Google Patents

Abstract

FIELD: chemistry.SUBSTANCE: invention relates to agrochemistry and can be used in maize cultivation.EFFECT: application of 4,6-dimethyl triazolo[1,5-]pyrimidyl-2-sulphanyl)-2-trifluoroacetanilide for treatment of corn in amount of 30 g/ha in phase of 2–4 leaves and in phase of 5–6 leaves provides yield increase and stimulation of corn growth.1 cl, 1 tbl

Description

The invention relates to chemistry and agriculture and can be used in the cultivation of corn.

Plant growth regulators are one of the most promising groups of pesticides, and it is no coincidence that it is replenished with new preparations every year. 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 he needs. The use of growth regulators provides, for example, a solution to such problems as increasing the yield and quality of grown products, increasing resistance to diseases and stressful situations, and much more (Plant Protection and Quarantine - 2008. - No. 12. - P. 54).

Corn is one of the main crops of modern world agriculture. This is a crop of versatile use and high yield. About 20% of corn is used for food in Russia, 15-20% for technical purposes, and about two-thirds for animal feed. It is obvious that the search for ways and means of increasing the yield and quality of corn grain is an urgent task. One of these techniques is the use of growth regulators in culture cultivation technology.

The objective of the invention is to expand the arsenal of corn growth regulators.

The technical result of the invention is to increase the yield of corn.

This result is achieved by using (4,6-dimethyltriazolo- [1,5- a ] pyrimidyl-2-sulfanyl) -2-trifluoroacetanilide of formula I:

as a growth regulator for maize when sprayed twice at a dose of 30 g / ha in the phase of 2-4 leaves and in the phase of 5-6 leaves.

The claimed compound I was obtained by the authors for the first time by the interaction of 4,6-dimethyl-1,2,4-triazolo [1,5- b ] -pyrimidyl-3-thiol III with N- (2-trifluorophenyl) chloroacetic acid amide IV, which was previously obtained the interaction of chloroacetyl chloride with 2-trifluoroaniline:

Synthesis scheme:

The complete synthesis of 4,6-dimethyl-1,2,4-triazolo [1,5- b ] -pyrimidyl-3-thiol III is described in the work ["Synthesis of new herbicide antidotes for sunflower", Strelkov V.D., Dyadyuchenko L .V., Dmitrieva I.G., Krasnodar, "Education-South", 2014, S. 96].

The closest analogue in structure to the claimed compound is a compound of formula II ["Method for increasing the yield of soybeans". Dyadyuchenko L.V., Nazarenko D.Yu., Morozovsky V.V., Dmitrieva I.G., Golubeva N.V., Pat. RF, No. 2617322 dated 04.24.2017. Application No. 2016111921 dated 03.29.2016]:

The well-known growth regulator Bigus, BP (State catalog of pesticides and agrochemicals permitted for use in the Russian Federation. Ministry of Agriculture of Russia. Moscow - 2018) was chosen as an analogue in properties (reference).

Growth-regulating activity was determined according to the standard method (Guidelines for registration tests of plant growth regulators, defoliants and desiccants in agriculture. Ministry of Agriculture of the Russian Federation. Moscow, 2016).

Synthesis techniques:

(4,6-dimethyltriazolo [1,5- a ] pyrimidyl-2-sulfanyl) -2-trifluoroacetanilide (compound I).

To a suspension of 1.0 g (5.6 mmol) of 4,6-dimethyl-1,2,4-triazolo [1,5- b ] -pyrimidyl-3-thiol III in 20 ml of DMF, add a solution of 0.31 g ( 5.6 mmol) KOH in a minimum amount of water and stirred for 0.5 h.Then a solution of 1.03 g (5.6 mmol) of M- (2-trifluorophenyl) chloroacetic acid amide IV in 10 ml of DMF is added and stirred for another 3 h The reaction mass is diluted with 30 ml of water, the separated precipitate is filtered off, washed with water, and dried. After purification by recrystallization from ethanol, 1.19 g (67%) of the target product I are obtained in the form of white crystals with T _pl . 194-195 ° C.

Found,%: C = 58.7056; H = 5.28; N 21.16; S = 9.88. C ₁₆ H ₁₇ F ₃ N ₅ OS;

Calculated,%: C = 58.70; H = 5.23; N 21.39; S = 9.79.

¹ H NMR spectrum, δ, ppm (group): 2.52 (s, 3H, 4-CH ₃ ); 2.72 (s, 3H, 6-CH ₃ ); 3.72 (s, 2H, CH ₂ ); 6.65 (s, 1H, 5-H Py); 7.35 ... 8.03 (m, 4H, Ar), 10.80 (br. S, 1H, NH).

(4,6-dimethyltriazolo [1,5- a ] pyrimidyl-2-sulfanyl) -4-fluoroacetanilide (compound II).

To a suspension of 1.0 g (5.6 mmol) of 4,6-dimethyl-1,2,4-triazolo [1,5- b ] -pyrimidyl-3-thiol III in 20 ml of DMF, add a solution of 0.31 g ( 5.6 mmol) KOH in a minimum amount of water and stirred for 0.5 h. Then a solution of 1.05 g (5.6 mmol) of N- (4-fluorophenyl) chloroacetic acid amide IV in 10 ml of DMF is added and stirred for another 2 h The reaction mass is diluted with 30 ml of water, the separated precipitate is filtered off, washed with water, and dried. After purification by recrystallization from ethyl acetate, 2.55 g (72%) of the target product II are obtained in the form of white crystals with T _pl . 176-177 ° C.

Found,%: C = 54.66; H = 4.20; N 21.38; S = 9.51. C ₁₅ H ₁₄ FN ₅ S;

Calculated,%: C = 54.37; H = 4.26; N = 21.13; S = 9.68.

¹ H NMR spectrum, δ, ppm (group): 2.59 (s, 3H, 4-CH ₃ ); 2.78 (s, 3H, 6-CH ₃ ); 3.72 (s, 2H, CH ₂ ); 6.48 (s, 1H, 5-H Py); 7.21 ... 7.64 (m, 4H, Ar), 9.80 (br. S, 1H, NH).

Experiments on corn plants.

Evaluation of the growth-regulating activity of the synthesized compound on maize plants of Krasnodarskiy 377AMV (F1) variety was carried out in the experimental field of VNIIBZ. The reference was used in the recommended amount for maize of 300 ml / ha.

Maize plants Krasnodar 377AMB were treated with an aqueous solution of the claimed 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). Plants were treated with a solution of structural analogue II in a similar way; solution Bigus, BP was applied in the same phases (dose 300 ml / ha) with the rate of flow of the working fluid of 300 l / ha.

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

Growth-regulating activity was determined by increasing the grain yield of plants treated according to the proposed method and according to the reference method, in comparison with the control (untreated plants).

The data obtained are presented in the table.

Tests carried out on corn have shown that the claimed compound I, when applied twice at a dose of 30 g / ha, exhibits growth stimulating properties.

Thus, the proposed invention realizes the specified purpose, providing an increase in the corn yield of 8.2 c / ha (14.0%), while the standard contributes to an increase in the yield of corn by 4.4 c / ha (8.8%). The analogue exhibits weak growth-stimulating properties in structure.

Claims (3)

Use of (4,6-Dimethyltriazolo- [1,5- a ] pyrimidyl-2-sulfanyl) -2-trifluoroacetanilide of formula I:

as a growth regulator for maize when sprayed twice at a dose of 30 g / ha in the phase of 2-4 leaves and in the phase of 5-6 leaves.