RU2479204C1 - Method of protecting vegetative sunflower plants from damaging effect of 2,4-dichlorophenoxy acetic acid - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: invention relates to agriculture. In order to protect vegetative sunflower plants from the damaging effect of 2,4-dichlorophenoxy acetic acid, said plants are treated with benzyl ether (4,6-dimethyltriazolo-[1,5-a]pyrimidyl-2-sulphanyl)-acetic acid of formula I:

in amount of 200 g/ha, three days after applying the herbicide.

EFFECT: invention increases sunflower yield.

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Description

The invention relates to a technology for the protection of cultivated plants from the damaging effects of herbicides.

A known method of protecting vegetative crops from the damaging effects of herbicides, providing for their treatment with an antidote after using the herbicide (Pitina M.R. et al. The current level and promising areas of crop protection from the undesirable effects of the use of herbicides. // Agrochemistry, 1986, No. 4, p. 107-136).

The objective of the invention is to expand the arsenal of antidotes of sunflower from the damaging effects of 2,4-D.

The technical result of the invention is the protection of vegetative sunflower plants from the damaging effects of 2,4-D, which is expressed in an increase in yield compared to a herbicide-treated control.

This result is achieved by the fact that in the method of protecting vegetative plants from the damaging effects of 2,4-D, which involves treating them with an antidote after using the herbicide, benzyl ether (4,6-dimethyltriazolo- [1,5- a ] is used as an antidote) pyrimidyl-2-sulfanyl) acetic acid of the formula I:

in an amount of 200 g / ha 3 days after using the herbicide.

The synthesis of the antidote was first carried out by the authors according to the scheme:

Synthesis Method:

To a suspension of 1.4 g (7.8 mmol) of 4,6-dimethyltriazolo- [1,5- a ] pyrimidin-2 thiol in 15 ml of DMF is added a solution of 0.44 g (7.8 mmol) of KOH in a minimum amount of water , stirred at room temperature for 10 minutes, then a solution of 1.44 g (7.8 mmol) of benzyl ester of chloroacetic acid in 15 ml of DMF was added and stirring was continued for another 1.5 hours. The reaction mixture was diluted with water twice, the precipitate that formed was filtered off, washed with water are dried. After recrystallization from cyclohexane, 1.80 g (71%) of the desired product I are obtained in the form of crystals with a melting point of 118-119 ° C.

Found,%: C 58.86; H 5.06; N, 17.30. C ₁₆ H ₁₆ N ₄ O ₂ S;

Calculated,%: C 58.52; H 4.91; N, 17.06.

¹ H NMR spectrum, δ, ppm (group): 2.59 (s, 3H, 4-CH ₃ Py); 2.79 (s, 3H, 6-CH ₃ Py); 3.79 (s, 2H, SCH ₂ ); 5.06 (s, 2H, CH ₂ ); 6.42 (s, 1H, 5-H Py); 7.07 ... 7.70 (m, 5H, Ar).

The antidote activity of the obtained compound in sunflower plants was evaluated on the experimental field of the All-Russian Research Institute for Plant Biological Protection. As a prototype, the well-known antidote 2,4-D-sulfalene was used (List of pesticides and agrochemicals approved for use on the territory of the Russian Federation. Appendix to the journal Plant Protection and Quarantine, 2002, No. 6). The standard was used in the recommended amount for sunflower 200 g / ha at a flow rate of 500 l / ha.

Evaluation of the antidote activity of the claimed compound I and prototype (sulfalene) was carried out according to the following method.

In the field, sunflower plants of VNIIMK 8883 cultivar were treated with 2,4-dichlorophenoxyacetic acid butyl ether at a dose of 18 g / ha in a 10-16 leaf phase and after 3 days an antidote solution was applied at a dose of 200 g / ha with a working fluid flow rate of 500 l / ha.

In the experiment, the following options are provided:

- control - untreated plants;

- “herbicide” (standard) - plants treated with a herbicide;

- "herbicide + antidote" - plants treated with herbicide and antidote.

The experiments were carried out on plots with an area of 2.8 m ² , a fivefold repetition. Harvesting of sunflower seeds was carried out at the time of complete ripening of seeds.

The antidote effect was determined by the absolute value of the yield increase to the herbicidal standard and in percentage by the formula:

A _x - antidote effect,%;

A - crop in the variant antidote + herbicide;

E - crop in the standard version (herbicide).

The data obtained are statistically processed using t-student test.

The test results are presented in the table.

Antidote activity of benzyl ester (4,6-dimethyltriazolo- [1,5- a ] pyrimidyl-2-sulfanyl) acetic acid (compound I) and prototype (sulfalene) in relation to 2,4-D in sunflower Antidote Dose of antidote, g / ha Experience Options 2,4-D (herbicide) 2,4-D + antidote Productivity, t / ha Productivity, t / ha Antidote activity c / ha % Compound I 200 17.1 22.3 5.2 thirty* Sulfalen (prototype) 200 17.1 20.1 3,1 eighteen The control - 40.6 - - - The differences between the variants are significant at P = 0.90

Thus, the present invention allows to provide an antidote effect at the level of 30% against 18% of the prototype, which increases the yield of sunflower by 5.2 c / ha.

Claims (1)

A method for protecting vegetative sunflower plants from the damaging effects of 2,4-D, comprising treating them with an antidote after using a herbicide, characterized in that benzyl ether (4,6-dimethyltriazolo- [1,5-a] pyrimidyl-2- is used as an antidote sulfanyl) -acetic acid of the formula I:

in an amount of 200 g / ha 3 days after using the herbicide.