RU2072781C1 - Herbicide composition - Google Patents

Abstract

FIELD: organic chemistry. SUBSTANCE: herbicide composition has an active compound - 0.5-55 wt.-% sulfonylurea of the general formula

where: R₁ - Cl, OCH₂CH₂Cl; R₂ - CH₃OCH₃; R₃ - OCH₃,CH₃ or its diethanolamine salt, 0.5-10 wt.-% activating addition - processing product of hemp resinification or its alkylamine or alkanolamine derivative and up to 100 wt.-% solvent - hydroxyethylated amines taken from monoalkylamines, dimethylalkylenediamines, tetramethyldialkylenetriamines that contain from 3 to 18 carbon atoms and from 10 to 15 hydroxyethyl groups in alkyl or alkylene moieties. Composition is used in agriculture for struggle against weed. EFFECT: improved method of synthesis. 3 tbl, 11 ex

Description

где R₁ Cl, OCH₂-CH₂Cl; R₂CH₃, OCH₃; R₃ OCH₃, CH₃.The invention relates to the field of agriculture, namely to the preparation of compositions for controlling weeds based on sulfonylurea derivatives of the general formula:

where R ₁ Cl, OCH ₂ —CH ₂ Cl; R ₂ CH ₃ , OCH ₃ ; R ₃ OCH ₃ , CH ₃ .

A feature of these compounds is that at a temperature of +5 ^o C and below, their hydrolysis in the soil is sharply reduced. In a continental climate with frosty winters and low temperatures in the autumn-spring period, the decomposition of sulfonylurea slows down, and its storage period in the soil is prolonged for 6-8 months. There is an increased risk of damage to sensitive crops as a result of the consequences. Therefore, the problem of reducing the hectare dose of the active substance consumption is relevant.

 A known method of using sulfonylurea chlorosulfuron (compound I) in the form of an aqueous solution of sodium salt (1). This composition has low stability (stable less than 6 months), a positive pour point, low concentration of the active substance in preparative form (5% aqueous solution), which creates a number of difficulties in storage, transportation and use. This composition is taken as a prototype and has the following ratio of components, wt.

N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl-2-chlorobenzenesulfamide sodium salt 5
Water 95
Working solutions based on this composition are successfully used in the control of annual and dicotyledonous weeds, but due to the low penetration ability into plants, effectiveness against most broad-leaved weeds is achieved only at consumption rates of 10-50 g / ha. Such doses of application cause long periods of aftereffect, significant difficulties in crop rotation and limits the scope of the drug to industrial and grain crops.

 The aim of the invention is to provide a composition with greater biological activity, a lower dose of the active substance and, as a consequence, a smaller aftereffect on chlorosulfuron-sensitive crops sown next year.

 This goal is achieved by introducing into the composition of additives that increase the permeability of working solutions in plants, and hence the herbicidal activity of the drug. As activating additives, abietic acid is used, which is part of hemp osmol processing products (rosin, balsam), as well as their derivatives. Fatty amine hydroxyethylation products were used as a solvent for the salt-forming agent.

 The proposed composition is characterized by the following ratio of components, wt.

Sulfonylurea or its diethylethanolamine salt 0.5-55.0
Hemp osmol processing product or its derivative 0.5-10.0
Thinner The rest is up to 100.

Example 1. In a three-necked flask equipped with a stirrer and a thermometer, 6.4 g of diethylethanolamine was charged, heated to 40 ^{° C.} and 20 g of sulfuron (compound I) was gradually added. After salt production, the composition is kept at a temperature of 40 ^° C for 2 hours and 63.6 g of hydroxyethylated dimethylalkyl (C ₁₂ -C ₁₈ ) amine are added as solvent, mixed well and 10 g of terpene esters of abietic acid are added and stirred for 30 minutes. The resulting preparation is a light brown liquid, readily soluble in water with a permeability constant of P 2.5 • 10 ^-5 cm / min.

 Example 2. Analogously to example 1 receive a preparation of the following composition, wt.

Diethylethanolamine salt of compound I 13.27
Diethylethanolamine salt of abietic acid 3.0
Solvent oxyethylated dimethylalkyl (C ₁₂ -C ₁₈ ) amine - 83-73
with a permeability constant P of 3.2 • 10 ^-5 cm / min.

 Example 3. Analogously to example 1 receive a preparation of the following composition, wt.

Diethylethanolamine salt of compound I 6.64
Monoethanolamine salt of abietic acid 0.5
solvent ethoxylated dimethylalkyl (C ₁₂ -C ₁₄ ) amine - 92.86
with a permeability constant P of 3.4 • 10 ^-5 cm / min.

 Example 4. Analogously to example 1 receive a preparation of the following composition, wt.

Diethylethanolamine salt of compound I 0.66
Abietic acid dimethylalkylamine salt 0.1
Ethoxylated Tetramethyldipropantriamine 99.24 Solvent
with permeability constant P 3.0 • 10 ^-5 cm / min.

 Example 5. Analogously to example 1 receive a preparation of the following composition, wt.

Diethylethanolamine salt of 2-chloroethoxy-N - [(6-methoxy-4-methyl1,3,5-triazin-2-yl) aminocarboxylic sulfonamide] (compound II) 12.91
Abietic acid 2.0
Solvent oxyethylated dimethylpropanediamine 85.09
with a permeability constant P of 3.2 • 10 ^-5 cm / min.

 Example 6. Analogously to example 1 receive a preparation of the following composition, wt.

Diethylethanolamine salt of compound II 55.0
Abietic acid monoethanolamine salt 1.0
Solvent oxyethylated tetramethyldipropanediamine 44.0
with a permeability constant of P 2.9 • 10 ^-5 cm / min.

Example 7. In a three-necked flask with a stirrer, 93 g of ethoxylated dimethylalkyl (C ₁₂ -C ₁₄ ) amine are loaded, heated to 40 ^° C, 2 g of sulfonylurea (compound II) are added and stirred until complete dissolution. Then 5 g of terpene esters of abietic acid are added and stirred for 30 minutes. A light brown water-soluble liquid with a permeability constant of P 3.0 • 10 ^-5 cm / min is obtained.

 Example 8. Analogously to example 7 without the use of an activating additive receive the preparation of the following composition, wt.

Compound II 0.6
Oxyethylated dimethylalkyl (C ₁₂ -C ₁₈ amine 99.4
with a permeability constant P of 1.7 • 10.0 ^-5 cm / min.

 Example 9. Analogously to example 7 receive a preparation of the composition, wt.

Compound I 5.0
Abietic acid 6.0
Oxyethylated Dimethylalkyl (C ₁₂ -C ₁₄ ) Amine 89.0
with a permeability constant of P 3.3 • 10 ^-5 cm / min.

где ΔC_o и ΔC_τ разница в концентрации д.в. в начальный момент и момент времени t,, V₁ и V₂ объем растворов, находящихся по обе стороны мембраны, А площадь мембраны.Example 10. The permeability constant of the working solutions was determined by the in vitro method in the herbicide membrane water system [5]
As a membrane, a cuticle of a sunflower leaf was used in the development phase of 2-3 pairs of true leaves. The cuticular membranes were separated from the tissues below them by a mixture of ammonium oxalate and oxalic acid. Then washed with distilled water. The cuticle was fixed at the end of the glass tube with a working solution in contact with the outer surface of the cuticular disk and with water in the bottle from the outside. At certain intervals, the concentration of the active substance in the selected samples was measured. The permeability constant was calculated by the equation:

where ΔC _o and ΔC _{τ the} difference in concentration of AI at the initial moment and time t ,, V ₁ and V _{2 the} volume of solutions located on both sides of the membrane, And the area of the membrane.

Example 11. Crops of spring wheat were treated with herbicidal compositions prepared according to the examples at doses of 3,5,7,10,15,20 g / ha in the tillering phase. Weed vegetation was represented by the following species: pink sow thistle, white gauze, tar sap, buckwheat buckwheat, hawthorn, wild radish and other dicotyledonous weeds. The average number of weeds was 211 pcs / m ² . Accounting for herbicidal action was established by inhibition of the weight of the wet mass of weeds in relation to the control one month after spraying. Productivity was established by threshing plants from all over the plot (10 m ^{2 area} , four-fold repetition). The results are presented in table 1-3.

 Given in the table. 2, 3 data indicate a higher herbicidal activity and excellent selectivity of the proposed compositions in comparison with the prototype. So, to achieve the herbicidal effect of suppressing weeds by 7-10 g / ha, the prototype this activity is observed when applied at a dose of more than 15 g / ha. Due to the higher effect, it is possible to reduce the hectare dose of application, which will reduce the negative aftereffect of sulfonylurea on sensitive crops.

 Thus, the proposed herbicidal composition has a high biological activity.

 Note to Table 1-3.

Examples 1,2 show an ethoxylated amine with the number of carbon atoms C ₁₂ -C ₁₈ .

In examples 3.7, ethoxylated dimethylalkylamine with the number of carbon atoms C ₁₂ -C ₁₄ .

In examples 4.6, the ethoxylated amine is C ₆ -tetramethyldipropanetriamine oxyethylated 10 mol of ethylene oxide.

In Examples 5.8, the ethoxylated amine is C ₃ -tetramethyldipropanetriamine oxyethylated 10 moles of ethylene oxide.

Claims (1)

A herbicidal composition comprising a sulfonylurea of the formula I:

where R ₁ -Cl, -OCH ₂ CH ₂ Cl;
R ₂ —CH ₃ , —OCH ₃ ;
R ₃ —OCH ₃ , —CH ₃ ,
or its diethanolamine salt and solvent, characterized in that the solvent composition contains oxyethylated amines selected from monoalkylamines, dimethylalkylenediamines, tetramethyldialkylenetriamines, which contain in the alkyl or alkylene parts 3 18 carbon atoms and 10 15 oxyethyl groups, and additionally contains as an activating additives product of hemp osmol or its alkylamine or alkanolamine derivative in the following ratio, wt. Sulfonylurea of the formula I or its diethylethanolamine salt 0.5 55.0
Hemp osmol processing product or its derivative described above 0.5 10.0
Solvent described above Up to 100s

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