HU185226B - Herbicide composition containing carbamide derivative further process for preparing the active substance of composition - Google Patents

Abstract

The invention relates to novel herbicidal compositions which, in addition to conventional auxiliaries and traeger substances, and optionally further herbicides as the active ingredient. 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea. The active ingredient is particularly suitable for controlling weeds that grow in crops such as corn, barley and especially wheat.

Description

The present invention relates to a process for the preparation of a new urea derivative and to a herbicidal composition containing it.

A large number of herbicidal urea derivatives are disclosed in U.S. Patent No. 2,655,447. In the 25 years since the first production of these derivatives, much research has focused on the use of urea derivatives as herbicides. The most important urea derivative is 3- (4-isopropylphenyl) -1,1-dimethylurea, commercially available as Jsoproturon. This compound is widely used in Europe for weed control (live in cereals. The main advantage of the compound is that it is effective against a wide variety of weeds and that it can be used as a pre- or post-emergent agent in autumn and winter. However, it has the disadvantage of Thus, it is ineffective against perennial broadleaf weeds, perennial weeds, weeds and veronica.

It has been found that certain phenylurea derivatives not specifically described in U.S. Patent No. 2,655,447, wherein the phenyl ring has two specific substituents, have particularly useful herbicidal properties.

SUMMARY OF THE INVENTION The present invention relates to a process for the preparation of a compound of formula I, namely 3- (3-melyl-4-isopropyl-phenyl) -1,1-dimethylurea. As a pre- or post-emergence agent, this compound is particularly useful for controlling weeds growing in cereals, such as corn, barley, and especially wheat. As evidenced by the data in Examples 4 and 5, this compound has distinct advantages over the commercially available "Isoproturon" herbicide in wheat weed control.

According to the invention, the compound of formula I is prepared by reacting the aniline derivative of formula II or a hydrohalide salt thereof (a) with a dimethylcarbamoyl halide, preferably chloride, optionally in the presence of a dehydrohalogenating agent.

Process variant (a) may be carried out in a solvent, without the use of a solvent. Suitable solvents are hydrocarbons and halogenated hydrocarbons such as benzene, toluene and carbon tetrachloride. The reaction is preferably carried out under substantially anhydrous conditions. Since the reaction is a condensation reaction involving the elimination of hydrogen halide, it is preferable to work in the presence of a dehydrohalogenating agent. Suitable dehydrohalogenating agents are particularly preferred when working with organic or inorganic bases, such as solvents, or sodium bases such as triethylamine and pyridine in solvents. The reaction is preferably carried out at a temperature between 0 ° C and 80 ° C, preferably at room temperature, and the reaction mixture is worked up by conventional methods,

A further object of the present invention is to provide a herbicidal composition comprising a compound of formula I and a suitable carrier. A further object of the present invention is to provide a method for writing undesired plants, which method comprises treating the site of plants with the composition of the invention.

In some cases, it may be desirable to mix the compound of the invention with other herbicidal compounds, so that the compound of the present invention may be mixed with other broad-spectrum herbicides such as 2- (4-chloro-6-ethylamino-s-triazine). 2-amino) -2-methylpropionitrile (traditionally called cyanazine) or more specific herbicides. such as alanine-type wild oat herbicides. The latter herbicides are disclosed in British Patent No. 1,164,160, of which herbicides are ethyl N-benzyl-N- (3,4-dichlorophenyl) -2-aminopropionate (traded as benzoyl propyl ethyl). and a racemic mixture or (-) isomer (trade name of flamprop-isopropyl and flamprop-methyl) of isopropyl or melyl N-benzoyl-N- (3-chloro-4-fluorophenyl) -2-aminopropionate.

In the composition of the invention, the carrier may be any material which is combined with the active ingredient to facilitate application of the active ingredient to the site of application. The treatment site may be, for example, a plant, seed or soil. The carrier can also facilitate storage, transportation and handling of the material. The carrier may be a solid or liquid, including those which are in the normal state of being gaseous but have been liquefied, and any other carrier conventionally used in the production of herbicides.

Suitable solid carriers include:

natural and synthetic materials and silicates, such as natural silicates, such as silica; magnesium silicates, such as talc; magnesium aluminum silicas such as attapulgites and vermiculites; aluminosilicates such as kaolinites, montmorillonites and mica; calcium carbonate; calcium sulfate; synthetic hydrated silicas and synthetic calcium or aluminum silicates; elements such as sulfur or carbon; natural or synthetic resins such as coumarone resins, polymers and copolymers of polyvinyl chloride and styrene; solid polychlorophenols; bitumen; waxes such as beeswax, paraffin wax and chlorinated solid fertilizers such as superphosphates.

Suitable liquid carriers include:

water; alcohols such as isopropanol and glycols; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers; aromatic and araliphatic hydrocarbons such as benzene, toluene and xylenes petroleum distillates such as kerosene and light mineral oils; chlorinated hydrocarbons such as carbon tetrachloride. perchlorethylene and trichloroethane. Mixtures of different liquids can often be used.

Agricultural products are often prepared or transported in a concentrated form which is diluted immediately before use. A small amount of the surfactant present as a carrier helps dilution. Therefore, the invention

At least one of the carriers in the composition according to 185 226 is a surfactant. For example, the composition may contain at least two carriers, one of which is a surfactant.

The surfactant may be an emulsifier, dispersant or wetting agent; which may or may not be ionic. Among the surfactants that may be used are the sodium and calcium salts of polyacrylic acids and lignin sulfonic acids; fatty acids or aliphatic amines or amides having at least 12 carbon atoms with ethylene oxide and / or. condensation products of propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol; condensation products of glycerine, sorbitan, sucrose or pentaerythritol with ethylene oxide and / or propylene oxide; condensation products of fatty alcohols or alkyl phenols such as p-octylphenol or octylcresol ethylene oxide and / or propylene oxide; sulphates or sulphonates of these condensation products; salts of sulfuric or sulfuric acid esters of at least 10 carbon atoms with alkali metals or potassium earth metals, preferably sodium, such as sodium lauryl sulfate, sodium (sec-alkyl) sulfates, sodium salts of sulfonated castor oil, and sodium alkoxylate, benzene; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.

The compositions of the invention may be formulated, for example, as wettable powders, powders, granules, solutions, emulsifiable concentrates, suspension concentrates, and aerosols. Wettable powders generally contain 25, 50 and 75% by weight of wetting agent and 3-10% by weight of dispersant, in addition to the solid inert carrier, and optionally 0 to 10% by weight of stabilizer (s) and / or other additives such as penetrants or adhesives. containing enhancers. Powders are generally prepared in a composition similar to that of wettable powders, except that the powders do not contain dispersants. The powders are diluted with additional solid carriers at the site of application to form formulations which generally contain from 0.5 to 10% by weight of the active ingredient. The granules are prepared to have a particle size of 10 to 100 BS mesh (1.676-0.152 mm). The granules are prepared by agglomeration or impregnation techniques. The granules generally contain 0.5 to 25 seconds of active ingredient ^H and 0 to 10% by weight of additives such as slip stabilizers, slow release agents and binders. The emulsifiable concentrates contain from 10 to 50% by weight of the active ingredient, from 2 to 20% by weight of the emulsifier and from 0 to 20% by weight of the other additives, such as stabilizers, penetrants and corrosion inhibitors. The suspension concentrates are formulated to give a stable, non-settling, liquid product which is generally 10-75% by weight, of the active ingredient, 0.5-15% by weight, of a dispersant, 0.1-10% by weight of a suspending agent, e.g. lixolrop agents 0 to 10% by weight, other additives such as antifoam, corrosion resistant. stabilizers, penetrants and tackifiers, and water or an organic liquid in which the active ingredient is substantially insoluble. The composition, when dissolved, may contain ncg of certain organic solids or inorganic salts which will prevent sedimentation and water freeze inhibitors.

Aqueous dispersions and emulsions prepared by diluting the concentrates or wettable powders of the invention with water are within the scope of the present invention. The emulsions mentioned may be of the water-in-oil or oil-in-water type and may have a dense, mayonnaise-like flavor.

The compositions of the invention may also contain other ingredients, such as other compounds having insecticidal or brain fungicidal activity.

The following examples illustrate the invention.

Example 7 Preparation of? - (3-methyl-4-isopropyl-phenyl) -1,1-dimethyl-urea

7.4 g of 3-methyl-4-isopropylaniline and 0.5 g of anhydrous sodium acetate are mixed and 5.4 g of dimethylcarbamoyl chloride are added over 15 minutes. After standing overnight at room temperature, water was added and the mixture was quenched with methylene chloride. After drying over magnesium sulfate, the solvent was evaporated and the resulting solid was recrystallized from hexane / toluene. 3.5 g of the desired compounds are obtained, m.p. 153-154 ° C.

Analysis for the compound of formula C _u H ₂₀ N ₂ O:

C [%,] H [%] N [%] Calculated: 70.9 9.1 12.7 Tahit: 69.9 9.1 12.1

Example 2

A further method of preparing the compound of the invention was the refluxing of 3-methyl-4-isopropylaniline (g, 80% purity) in 15C ml of toluene for 1.5 hours while purging with XOCl gas. Subsequently, dry nitrogen gas was bubbled through the solution in order to remove the excess COC1 _2. The mixture was cooled to room temperature and a solution of 5 g of dimethylamine in 20 ml of toluene was added. The toluene was then evaporated and hexane was added to the residue and the precipitate was triturated to give 5.5 g of the desired product. The product had a melting point of 154 ° C after recrystallization from hexane / toluene.

Example 3

Preparation of 3-Methyl-4-isopropylaniline starting material

186 g of 3-mcylaniline were dissolved in 600 ml of 85% sulfuric acid. The solution was heated to 80 ° C and 120 g of isopropyl alcohol was added. The mixture was stirred for 1 hour at 80 ° C. The mixture was then poured onto ice and then ammonium hydroxide was added to make the solution neutral. Diethyl ether was added and the ether extract was evaporated. Distillation of the residue afforded 110 g of the desired product, boiling at 100 ° C at 2.5 mmHg.

Example 4

The compound of the invention has a selective herbicidal activity

a) Comparative experiment

In this experiment, a comparison was made between 3- (3-methyl-4-isopiopylphenyl) -1,1-dimethylurea and isoproturon, i.e. 3- (4-isopropylphenyl) -1,1-dimethyl-. selective herbicide in wheat. Preemergent experiments were conducted on Trilicum vulgare and postemergent experiments on Maris Huntsman wheat. The following weeds were tested: tarack, Argopyron repens (Co); vadzab, avenna fatua / ludoviciana (Wo); Italian grass, Lolium multiflorum (Rg); perje, Poa annua (Pa); tippan, Agrostis tenuis (Bt); Brush Lawn, Alopecurus myosuroides (Am); large warbler, Apera spica venti (Wg); star string, Stellaría media (St); veronica, Veronica persica (Sw); rabies, Galiuin aparine (Gg); apricot bitter grass, Polygonum lapathifolium (Pp); tansy honeysuckle, Lamium purpureum (Dn); mustard rape, Sinapis arvensis (Ck); chair grass, Matricaria ipacs, Papaver rhoeas (Po).

The test compounds were formulated in the form of concentrates emulgúlhaló containing _n ° 20 and active material, 10 wt% in mineral oil, elulgálószereket and as solvent xylene. Each concentrate was diluted with water and the plants tested were sprayed at doses of 6.0, 2.0.0.6.0.2, 0.06 and 0.02 kg / ha of active ingredient. For each dose, 4 replicates were performed. As a control, seedlings growing on untreated soil were used in preemergent studies, whereas seedlings growing on untreated soil were used in postemergent studies. In post-emergence studies, the efficacy of the drug was assessed visually at 21 and 28 days and for evaluation. a scale from 0 to 9 was used. In Eb ⁰ , 0 is the increase in untreated control and 9 is the death of the plant. On this scale, a linear increase of 1 unit corresponds to an increase of about 10% in the effect level.

The results were subjected to probit analysis, in which the computer estimates the values of a and b in the following equation:

Probit (% effect signal) = a + b log (dose) ²⁰ Using the resulting curve, we can calculate the appropriate dose level for a given level of effect signal. GID ₅₀ values were calculated for each plant species, that is, the dose required to achieve a 50% effect.

From this value, the selectivity factor for wheat for each weed was calculated:

The higher the selectivity factor, the more selective the herbicide. Finally, the ratio of the selectivity factors obtained for the compound of the invention to the selectivity factors obtained for isoproturon was calculated. Values greater than 1 indicate that the compound of the invention is more selective than isoproturon. The results are shown in l. The compounds of the invention are designated by the letter A and isoproturon by the letter 1.

Table 1

Preemergent test Postemergent test

iNovcny- types gid ₅₀ I THE selectivity factor I A Ratio of selectivity factors gid _w selectivity factor 1 Ratio of selectivity factors I THE 1 THE Wheat 1.23 1.67 - - - 1.69 1.67 - - - Co 1.99 1.05 0.6 1.6 2.7 0.93 0.61 1.81 2.7 1.5 Wo 0.6 0.59 2.1 2.8 1.3 0.14 0.19 12.1 8.8 0.7 rg 0.07 0.16 17.6 9.3 0.5 0.16 0.21 10.6 8.0 0.8 Pa 0.06 0.08 20.5 20.9 1.0 0.05 0.03 33.8 55.7 1.7 bt 0.02 0.02 61.5 83.5 1.4 0.08 0.02 21.1 83.5 4.0 am 0.10 0.18 12.3 9.3 0.8 0.04 0.06 42.3 27.8 0.7 Wg - - - - - 0.04 0.07 42.3 23.9 0.6 St 0.11 0.14 11.2 H, 9 U 0.08 0.06 21.1 27.8 1.3 sw 0.48 0.18 2.6 9.3 3.6 1.10 0.27 1.5 6.2 4.0 gg 1.87 0.91 0.7 1.8 2.6 2.42 0.46 0.7 3.6 5.2 pp 0.37 0.24 3.3 7.0 2.1 0.25 0.07 6.8 23.9 3.5 dn 0.15 0.10 8.2 16.7 2 0 0.41 0.18 4.1 9.3 2.3 ck 0.17 0.08 7.2 20.9 2.9 0.011 0,006 96.7 176.2 1.8 mw - - - - - 0.12 0.5 14.1 33.4 2.4 sp - - - - 0.11 0,015 14.2 105.7 7.5 Po - - - - - 0,001 0,001 Average 1.8 2.5

185,276

The following conclusions can be drawn from the data in Table 1.

1) The compound of the invention in pre-emergence tests against the tested gyomnövényből 12 by 9, while poszlemergens studies INSPECTION GALT ⁵ show a greater selectivity of isoproturon against 11 with 15 gyomnövényből.

2) The compound of the present invention exhibits much greater activity against the very important practical weevil (perennial weed), weed and veronica weeds.

3) The compound of the invention is on average 1.8 times more selective as isoproturon as preemergent and 2.5 times as average as postemergent.

b) Comparative experiment

A second experiment was conducted comparing 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea with another commercially available herbicide,

3- (3-chloro-4-methoxyphenyl) -1,1-dimethylurea ("Chloroluluron") and 3- (3-chloro-4-methylenenyl) -1,1-dimethylurea ("Metoxorun" ) selective herbicide. Except as noted below, the experimental method used in this preemergent assay was the same as that used for the preemergent assay in Comparative Experiment a). The following weeds were tested: tarack, Agropyron repens (Co); vadzab, Avena falua / Ltidoviciana (Wo); Italian fern, Lolliim multiflorum (Rg): fern, Poa annua (Pa); a fluffy silkworm, Holeus lanatus (Yo); Brush Lawn, Alcpecurus myosuroides (Am); sugar beet, Beta vulgaris (Sb); star string, Stellaria media (St); speedwell. Vcronica persica (Sw); cones, Convolvulus arvmsis (Cv); Apricot Fescue, Polygonum lapathifolium (Pp): Mustard, Sinapis arvensis (Ck). In this experiment, the results were evaluated after 20 days and the test results described in a) and in összehasonlítpő Experiment ¹⁵ except "Chlorotouron" herbicide calculated selectivity factors. Chlorotoluron was used as a standard. That is, the selectivity factors for each of the weeds obtained by chlorotoluron were divided by the selectivity factors for the other two corresponding compounds. Thus, the ratios in the chlorotholuron column are always 1. The results are summarized in Table 2. In the table, the compound of the invention is represented by the letter A, the chlorotoluron by the letter C, and the me'owuron by the letter M.

Table 2

plant Variety Cip ₅₀ selectivity factor Ratio of selectivity factors C M THE C M THE C M THE Wheat 2.11 1.54 2.13 - - - - - Co 1.71 3.23 1.36 1.23 0.48 1.57 1.00 0.39 1.28 Wo 1.58 0.82 0.58 1:34 1.88 3.67 1.00 1.40 2.74 rg 0.51 0.49 0.44 4.14 3:14 4.84 1.00 0.76 U7 Pa 0.19 0.22 0.11 11.11 7.00 19.36 1.00 0.63 L74 yo 0.19 0.19 0.14 11.11 8:11 15.21 1.00 0.73 1.37 am 0.33 0.87 0.26 6.39 1.77 8.19 1.00 0.28 1.28 sb 0.54 0.46 0.17 3.91 3.35 12:53 1.00 0.86 3.20 St 0.03 0.03 0.03 70.33 51.33 71.00 1.00 0.73 1.01 sw 0.45 0.29 0.19 4.46 5:31 11,21 1.00 1.13 2.39 Cu 0.25 0.64 0.90 1.65 2.41 2.37 1.00 1.46 1.44 pp 1.28 0.64 0.90 1.65 2.41 2.37 1.00 1.46 1.44 ck 0.67 0.24 0.10 3.15 6.12 21.30 1.00 2.04 6.76 Average 1.00 0.97 2.04

Table 2 shows that the compound of the present invention, when used as a preemergent in wheat, is more than twice as selective as either chlorotoluron or meloxurout.

Example 5

Evaluation of 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea in arable land

The efficacy and scope of 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylcarbanide and 3- (4-isopropylphenyl) -1,1-dimethylurea (isoproturon) were compared. between. The studies were conducted in Britain for a total of seven, winter; on a field sown with cereals. The tests were carried out on common winter wheat and winter barley containing naturally occurring weeds and / or broadleaf weeds.

Suspension concentrates containing 500 g / l of the compound of the invention and 509 g / l of isoproturon were diluted with water and four similar doses were used in each experiment. The following doses were used: 1.58. 2.10, 2.63, and 4.2 kg of active ingredient / ha. These doses are 3/4, 1, 1/4, and 2 times the recommended dose of 2.1 kg / ha for isoproturon for the spring preemergent treatment of ₆₅ winter grains.

In three experiments (Experiments 5, 6 and 7), the compounds of the present invention were used in combination with a spraying agent to improve the formulation properties. The mixture was formulated by mixing 1 part of a spraying agent with 2 parts of the active ingredient according to the invention. Experiments were performed on 10 x 3 m plots, and each experiment was repeated three times in random order. Spraying was performed using a gas pressure sprayer and 417 liters per hectare were applied. The data for each experiment are summarized in Table 3.

Evaluation of the effect of chemical treatment on herbaceous and broad-leaved weeds and the condition of the plants was performed 1 to 3 months after the treatment. For visual evaluation of crops, we used the EWRC 1-9 scale, where 0 represents inefficiency and 9 indicates crop death. The evaluation of broadleaf weeds consisted of estimating the coverage percentage of the individual weed species and the total weeds of the broadleaf weeds on the investigated plots. For herbaceous weeds, we evaluated the number of shoots on 6 or 8 parcels of equal size (0.5 m ² ) and converted this data into the number of flower beds. The following weeds were evaluated: a) broadleaf weeds: veronica, Veronica pcrsica (Sw), weed, Galium aparine (Gg), star string, Stellaria media (St), chair grass. Matricaria spp. (Mw), Orchid, Laminium purpurene (Dn); and (b) herbaceous weeds: brush ⁵ lawns, Alopecrus myrosuroides (Am); wild oats, vein spp. (Wo). Depending on the climatic conditions, the crops were harvested 138-169 days after treatment using a combine harvester. The grain weight of the harvested crops was measured.

¹ θ The results of the outdoor tests are summarized in Table 4 below. Each of the evaluated traits in the studies was averaged, i.e., the results from the various experiments were summarized. ¹⁵ h of crop yields were expressed as mean values from the EWRC scale obtained from the visual evaluation during the seven tests. The results for weed efficacy obtained according to the above procedures expressed a ² θ degree reduction in weed growth relative to the control. The efficacy against broadleaf weeds was also recorded during the experiment, and values for each weed in each experiment were reported as ²⁵ % of the weed growth relative to control in the "Total dicotyledonous" column. The weight of the crop was expressed as a percentage of the crop weight obtained on control plantations (100% of control)

Experiment produce Species Date of sowing (previous year) Treatment time Crop status (code below table) Temperature Soil for Hand Wet- Moisture Material equivalent [% J léskor rq ness [%] 1 winter wheat Sportsman 26, Sep 26, Mar. C, D 10.7 ° 27.1 26.0 34 2 winter barley Sonja 10, Oct. 28, Feb. A, F 6 ' 28.1 23.5 29 3 winter wheat M. Hobbit 9, Oct. 3, Mar. A, D 5 ' 28.3 31.2 44 4 winter wheat Hustler 17, Oct. 3, Mar. A, E 4,5 ' 22.3 33.5 41 5 winter wheat Flanders Oct 3, Apr THE 9.9 ° 38.6 36.1 52 6 winter wheat Flanders 11, Oct. 3, Apr C, D, G 10.0 ' 18.6 16.9 18 7 winter wheat What a lob bit 18, Oki. 3, Apr B, D 10.0 ' 16.1 16.8 16

Crop condition code:

A: 5 evolved leaves (seedlings)

B: 5 evolved leaves (seedlings)

C: 7 evolved leaves (seedlings)

D: mandibular and 2 lateral legs (mandibular)

E: mandibular and 3 lateral (peduncle)

F: shoots and 4 stems (shoots)

G: pseudo-stem development (stem elongation)

Table 4

Effect against weeds

Crop weight is the control

Test compound

Fügefélék

Broad-leafed weeds

am Wo sw St mw gg Dicotyledons ⁿ total Λ-aoan 3- (3-methyl-4-isopropyl- -phenyl) - 1,1-DIMEL : Ylcarbamide 1.58 2.2 79.1 19.4 75.3 95.3 93.4 56.0 65.2 82.2 129.9 2.10 2.3 87.2 27.6 80.2 95.5 94.1 "0.6 53.8 85.0 138.8 2.63 2.2 93.2 33.0 85.5 98.9 94.5 (.7,0 66.8 90.1 141.8 4.20 2.4 97.7 53.2 89.7 99.6 98.0 92.8 77.3 94.4 136.1 3- (3-isopropyl phenyl) -l, l-dimethyl- kiii 1) ti 1111 <1 1.58 2.10 2.63 2.2 2.1 2.0 85.9 90.3 93.5 21.7 34.0 36.1 45.1 50.0 43.6 96.2 97.6 98.8 95.1 99.2 100.0 8.0 2.5 20.3 49.8 43.4 45.5 70.1 72.9 73.4 134.8 136.6 130.1 4.20 2.2 97.9 48.9 52.9 99.8 87.7 21.0 72.0 78.7 134.5 control - 2.6 - - - - - - 100

Example 6

Herbicidal activity of the compound of the invention:

Using the 3- (3-methyl-4-isopripylphenyl) -1,1-dimethylurea produced by the process of the present invention, the following compositions were prepared:

ingredients: composition A C 3- (3-Methyl-4-isopropyl-phenyl-1,1-dimethyl-carboxylic acid) mid 470,750 4,700 glycol 90 0,900 Bevaloid 692M (Antifoam) 1 0,010 Klezan (Commercial Xanthan Gum) 2 0,020 formalin 2.5 0,025 Celanol PS17 (phosphoric acid ethoxylated nonylphenol mono- and diester mixed sodium of mustard: 14 0,140 Polyphone H (dispersant: sulphonated sodium salt of Kraft lignin) 40

Aerosol OTB (wetting agent: sodium dioctylsulfosuccinate) - 20 Microcel E: Clay CTY 50: 50 (diatomaceous earth: kaolinite clay mineral) - 190

1 from

1 additional water - supplemented with water

The herbicidal activity of the formulations was classified as post-and preemergent in the following crops: maize (MA) rice (Ri), celandine (BG), oat (OA), flax (LI), mustard (MU), sugar beet ( SB), soy (SO).

In the case of post-emergence studies the soil was treated and in the case of pre-emergence studies the leaves were sprayed with the formulations. For visual evaluation of crops, we used the EWRC 1-9 scale, where 0 indicates inefficiency and 9 indicates crop failure.

The results of the tests are summarized in Table 5.

Table 5

Formulation Test form Dose Postemergent

Preemergent [kg / ha] test

TODAY Ri BG OA LI MU SB SO MA Rí BG OA LI MU SB SO THE 50% SC 5 4 9 9 9 9 9 9 9 3 - 9 6 8 9 9 5 1 0 8 9 7 9 9 9 9 2 - 9 6 7 9 9 3 B 75% WP 5 4 9 9 9 9 9 9 9 4 - 9 6 8 9 9 6 1 0 8 9 7 9 9 9 9 2 - 9 6 7 8 9 4 C 0.5% SC 5 4 9 9 9 9 9 9 9 3 - 9 6 8 9 9 5 1 2 8 9 7 9 9 9 9 2 - 9 6 7 9 9 4

Claims (3)

CLAIMS 1. A herbicidal composition comprising a biologically active agent and a solid carrier, preferably natural or synthetic clay or silicate, or a liquid carrier, preferably water and glycol, and a surfactant, preferably an alkyl lignin sulfonate, wherein the active ingredient is 0.5. Contains 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea in -75 s. 2. A process for the preparation of 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea as an active ingredient in the composition of claim 1. to 3-methyl-4-isopropylaniline or a hydrohalide salt thereof, 0 to 80 "C Sensor stopping, ^5, are reacted under anhydrous conditions in the presence of a dehydrohalogenating agent dimethyl karbamoilhalogeniddel. Third embodiment of the method according to claim 2, characterized in that the used dimethyl karbomoil ¹⁰ halide, dimethyl carbamoyl chloride.