Diethylethanolamine salt of 2-etoxycarbonyl-n- [(4 - methoxy-6-chloro-1,3-pyrimidine-2-yl) -aminocarbonyl]- benzosulfimide with herbicide activity and herbicide composition based on it

 

(57) Abstract:

Usage: in agriculture, in particular as a herbicide funds. The inventive product diethylethanolamine salt of 2-etoxycarbonyl-N- [(4-methoxy-6-chloro-1,3-pyrimidine-2-yl) aminocarbonyl] benzosulfimide. In the herbicide composition is specified compound in a mixture with 2(or 4)-chlorobenzenesulfonyl - N-ethylaminoethanol in a ratio equal to 4:1. 2 S. p. f-crystals, 2 tab.

The invention relates to new derivatives of arylsulfonamides, which can be used in agriculture as a herbicide for weed control in soybean crops, in particular in a mixture with other compounds.

Known 2-etoxycarbonyl-N-[(4-methoxy-6-chloro-1,3-pyrimidine-2-yl)amino - carbonyl] benzosulfimide exhibiting herbicide activity in soybean (compound I) [1]

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(I)

However, due to its low solubility in water (0.025 g) 100 ml at 25aboutC, pH 5) the connection cannot be used in the form of a true aqueous solution, is preferred for use in agriculture. In addition, it is not hydrolytically stable, PR pH 5-7 it is hydrolyzed with a half-life of 4-8 weeks.
(C2H5)2NCH2CH2OH

(II) which can be used in aqueous-glycolic solution comprising the active substance 10% of the stabilizer of diethylethanolamine, emulsifier OP-7 or OP-10 and solvent mixture triethylene glycol and water in the ratio 1:1. Sol is stable for more than two years, herbicide composition based on diethylethanolamine salt of compound (II) is stable for 18 months. (when stored in a plastic container brand NS), and does not change its physical and chemical indicators. As salt and herbicide composition limited mixed with water and can be applied by the method of small-volume or ultra-low volume spraying. Connection and preparation to effectively suppress weeds in soybean crops, increasing the grain yield.

However, the greatest effect is obtained by mixing the herbicide from the salt and stimulator of plant growth on the basis of diethylethanolamine salt of 2-(4)-chlorobenzenesulfonyl-N-diethylaminoethylamine formula III

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(III)

Know the use of the herbicide on the basis of 2-etoxycarbonyl-N-(4-methoxy-6-chloro-1,3-pyrimidine-2-yl)aminocarbonyl] benzene sulphonamide (compound I) in a mixture with the compound of the formula

it 40-80 g/ha [2]

However, this mixture is not effective and does not show properties, which increases the amount of nitrogen-containing root nodules, which affect the growth of grain yield of soybean.

Joint use of salt II and III at a ratio of 4:1 gives a substantial increase in grain yield of soybean.

The mixture of salts is used in the form of an aqueous-glycolic solution of the following composition, wt. diethylethanolamine salt of 2-etoxycarbonyl-N-[(4-methoxy-6-chloro-1,3-PI - rimidine-2-yl)aminocarbonyl]bansilal - pamida-10,0; diethylethanolamine salt of 2-(4)-chlorobenzenesulfonyl-N-diethylaminoethylamine 2,5; diethylethanolamine 2,5; triethylene glycol 5,3; OP 7 (10) 5,0; water the rest.

Drug-resistant, when stored at low and elevated temperatures does not change the composition within 18 months.

As active ingredients, and preparative form in terms of the medium lethal dose when injected into the stomach belong to toxic substances, 3rd hazard class (GOST 12.1.007 76).

P R I m e R 1. Diethylethanolamine salt of 2-etoxycarbonyl-N-[(4-methoxy-6-chloro-1,3-pyrimidine-2-yl)aminocarbonyl] benzo of sulfamide (compound II).

To 300 ml of water added is 41.45 g (0.1 mol) 2-ecocut of 11.7 g (0.1 mol) of diethylethanolamine. Then the reaction mass is heated to 40-45aboutC and maintained at this temperature for one hour, cooled, the water evaporated under reduced pressure, dried in a vacuum desiccator to constant weight. Get 53,15 g (yield 100%) diethylethanolamine salt 2-etoxycarbonyl-N-[(4-methoxy-6-chloro-1,3-pyrimidine-2-yl)aminocarbonyl]benzo of sulfamide in the form of oil is light yellow in color.

WITH21H30ClN5O7S

Found, To 47.46; H Ceiling Of 5.60; N 13,19; S 6,00; Cl Of 6.71. Calculated: 47,41; N 5,64; N 13,17; S 6,02; Cl 6,88

IR-spectrum (in pure form):C=01668 cm-1, 1702 cm-1;WITH=N1596 cm-1; SO21170 cm-1, 1365 cm-1.

PMR-spectrum (Cl3-d1) : 1,12, CH3(C2H5); 3,10 CH2(C2H5); 3,84-a 3.87 m, CH2CH2the co3; 6,30 Shire.p. HE; 7,35 m, 8,10 c Ar.

P R I m m e R 2. An aqueous solution diethylethanolamine salt 2-etoxycarbonyl-N-[(4-methoxy-6-chloro-1,3-pyrimidine-2-yl)aminocarbonyl]benzo of sulfamide.

To 10 g of 2-etoxycarbonyl-N-[(4-methoxy-6-chloro-1,3-pyrimidine-2-yl)aminocarbonyl] benzosulfimide added under stirring to 45.6 ml of water, 3.8 g of diethylethanolamine. The mixture was kept at a temperature of 40-45aboutC for one hour, cooled, add co-chemical properties: pour point -28aboutWith, a surface tension of 48 nm/m, is stable for 1.5 years.

P R I m e R 3. An aqueous solution of a mixture of compound (II) and 2-chlorobenzenesulfonyl-N-diethylaminoethylamine.

To 12.8 g diethylethanolamine salt 2-ethoxycarbonyl-N-[(4-methoxy-6-chloro-1,3 - piridin-2-yl)aminocarbonyl] benzene - sulphonamide added under stirring 3.4 g diethylethanolamine salt 2-chlorobenzenesulfonyl-N-diethylaminoethyl-Balata, 38,65 ml of water, 1.5 g of diethylethanolamine, 38,65 g of triethylene glycol, 5 g of OP-7. The mixture is stirred for one hour.

The resulting composition has the following physical and chemical properties: pour point -28aboutWith, a surface tension of 42 nm/m, is stable for 1.5 years (herbicide composition 2).

P R I m e R 4. An aqueous solution of a mixture of compounds II and diethylethanolamine salt 4-chlorobenzenesulfonyl-N-diethylaminoethylamine.

To 10 g of 2-etoxycarbonyl-N-[(4-methoxy-6-chloro-1,3-pyrimidine-2-yl)aminocarbonyl] benzosulfimide and 2.5 g of 4-chlorobenzenesulfonyl-N-diethylaminoethylamine added under stirring 38,65 g of water and 5.2 g of diethylethanolamine. The mixture is stirred while heating to 40-45aboutC for one hour, cooled, add 38,65 g of triethylene glycol, 5 g of OP-10 and the temperature of solidification -32aboutWith, a surface tension of 42 nm/m, is stable for 1.5 g (herbicide composition 3).

P R I m e R 5. Tests of individual compounds and mixtures of soybean.

The tests were conducted at the stage of 3-4 leaves herbicide formulations I-III in the form of a water-glycol solutions and acid components of compounds I-III in the form of solutions in organic solvents with the addition of emulsifiers OP-7 or OP-10. Determined the destruction of weeds as a percentage of the control, as well as a lot of raw and dry weeds. Compounds 1-3 were effective against annual dicotyledonous weeds, including species of serizy and Marie white (see tab. 1). In the formation of the soybean crop is important, the number of nitrogen-fixing nodule bacteria. Therefore, we determined the number of nodule bacteria during processing of soybean in the phase of 2-3 leaves and grain yield of soybean (see table. 2).

Thus, diethylethanolamine salt of 2-etoxycarbonyl-N-[(4-methoxy-6-chloro-1,3-pyrimidine-2-yl)aminocarbonyl] benzo of sulfamide and, more herbicide composition based on it, representing a mixture with diethylethanolamine salt of 2 - or 4-chlorobenzenesulfonyl-N-diethylaminoethylamine allows to increase the yield of soybean on 42-64% CPA - chloro-1,3-pyrimidine-2 - yl)-aminocarbonyl] benzosulfimide formula

< / BR>
have a weed-killing activity.

2. Herbicide composition containing the active substance-derived 2-etoxycarbonyl-N- [(4-methoxy-6-chloro - 1,2-pyrimidine-2-yl) aminocarbonyl)- benzosulfimide, stabilizer, emulsifier and a solvent, characterized in that the active substance use diethylethanolamine salt of 2-etoxycarbonyl-N- [(4-methoxy-6-chloro-1,3 - pyrimidine-2-yl)- aminocarbonyl]- benzosulfimide mixed with diethylethanolamine salt of 2-(or 4)-chlorobenzenesulfonyl - N)-diethylaminoethylamine when the following ratio of components, as a stabilizer diethylethanolamine, and as a solvent a mixture of triethylene glycol and water in the ratio of 1 to 1 wt.

Diethylethanolamine salt of 2-etoxycarbonyl - N-[(4-methoxy-6 - chloro-1,3-pyrimidine-2-yl)- aminocarbonyl] benzosulfimide 10,0

Diethylethanolamine salt of 2-(or 4)- chlorobenzenesulfonyl-N - diethylaminoethylamine 2,5

Diethylethanolamine 2,5

Triethylene glycol 5,3

Emulsifier (OP-7 or OP-10) 5,0

Water The Rest

 

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