RU2567515C1 - Method of protecting vegetative sunflower plants from damaging effect of 2,4-dichlorophenoxyacetic acid - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: method includes treating sunflower with an antidote in amount of 200 g/ha one day after using 2,4-D. As the antidote N-(4-ethylphenyl)-4-methyl-2,6-dichloronicotinamide of formula I is used:

.

EFFECT: high sunflower yield.

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. and others. The current level and promising areas of protection of crops from undesirable consequences of the use of herbicides // Agrochemistry, 1986, No. 4, p. 107-136].

The objective of the invention is to expand the arsenal of antidotes for 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, providing for their treatment with an antidote after using the herbicide, according to the invention, N- (4-ethylphenyl) -4-methyl-2,6- is used as an antidote dichloronicotinamide of the formula I:

in an amount of 200 g / ha 1 day after using the herbicide.

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

Synthesis Method:

To a solution of 1.0 g (4.5 mmol) of 4-methyl-2,6-dichloronicotinic acid chloride in 10 ml of anhydrous benzene, a solution of 0.58 g (4.9 mmol) of 4-ethylaniline and 0.46 g (4 , 5 mmol) of triethylamine in 15 ml of anhydrous benzene and stirred at room temperature for 7 hours. The reaction mass is filtered off from the precipitate of triethylamine hydrochloride and evaporated to dryness. The residue is treated with water, dried, after recrystallization and a mixture of cyclohexane 6 ethyl acetate = 5: 1, 1.05 g (71%) of the desired product I are obtained, mp 171-172 ° C.

Found,%: C 58.45; H 4.48; N, 9.27; C ₁₅ H ₁₄ CI ₂ N ₂ O.

Calculated,%: C 58.26; H 4.57; N, 9.06.

¹ H NMR spectrum, δ, ppm (J, Hz): 1.18 (t, 3H, CH ₂ CH ₃ , J = 6.8 Hz); 2.32 (s, 3H, CH ₃ -4); 2.60 (q, 2H, CH ₂ CH ₃ , J = 6.8 Hz); 7.20 ... 7.58 (m, 4H, aryl-H); 7.60 (s, 1H, pyridin-H); 10.61 (br s, 1H, NH).

Mass spectrum, m / z (relative intensity,%): M ⁺ 308 (17); 188 [M-NHC ₆ H ₄ (C ₂ H ₅ ) -2] ⁺ (100); 160 [188-CO] ⁺ (14); 124 [160-HCI] ⁺ (20).

The synthesis of 4-methyl-2,6-dichloronicotinic acid and its acid chloride is described by us in [Dyadyuchenko L.V. et al. Synthesis of some halogen and nitro substituted nicotinic acids and their fragmentation under electron impact // Chemistry heterocycle. compounds, 2004, No. 3, p. 381-388].

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 used the well-known antidote 2,4-D - sulfalene (List of pesticides and agrochemicals approved for use on the territory of the Russian Federation. Appendix to the journal "Protection and Quarantine of Plants", 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, flagman sunflower plants in the 10-16 leaf phase were treated with 2,4-dichlorophenoxyacetic acid butyl ether at a dose of 18 g / ha and after 1 day 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 , five 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:

where 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.

Thus, the present invention allows to provide an antidote effect at the level of 41% against 20% of the prototype, which increases the yield of sunflower by 8.7 kg / ha.

Claims (1)

A method of protecting vegetative sunflower plants from the damaging effects of 2,4-D, providing for their treatment with an antidote after using the herbicide, characterized in that N- (4-ethylphenyl) -4-methyl-2,6-dichloronicotinamide of the formula I is used as an antidote:

in an amount of 200 g / ha 1 day after using the herbicide.