CS237332B2 - Herbicide agent - Google Patents

Abstract

A herbicidal composition characterized in that that it contains the derivative 1- - (2,6-dimethoxybenzoyl) -3- (substituted phenyl) urea general formula I when R 2 and R 3 are the same and represent methoxy or a chlorine atom, then all R 4 represents hydrogen atoms, or if both R2 and R3 are fluorine atoms, then individual R4 symbols each independently represents fluorine or hydrogen, in combination with one or more agriculturally acceptable carriers; \ tor. \ t diluents.

Description

The invention relates to a group of novel 1-subst.-benzoyl-3-subst. phenylureas which have been found to act as herbicides.

The use of herbicides to combat the growth of undesirable vegetation has been the subject of considerable research efforts for many years. In many cases, combating undesirable vegetation has a considerable economic effect. There are many problems associated with the constant use of chemical herbicides, including environmental pollution, crop compatibility, weed resistance, and economic aspects. Accordingly, there continues to be a search for new economically acceptable herbicides that are selectively toxic to undesirable vegetation.

1-Benzoyl-1-phenylureas useful as herbicides are already known. Pillon et al. in U.S. Pat.

No. 384,473 describes the use of various 1-phenyl-1-benzoylureas useful as herbicidal agents. Lehureau et al. U.S. Pat. No. 3,342,586 widely discloses ureas exhibiting herbicidal activity, but only 1-phenyl-1-alkanoylureas are mentioned as a preferred class of ureas. U.S. Pat.

No. 166,124, and Dutch Patent Application No. 7,105,350, published Oct. 24, 1972 (equivalent Argentine Patent No. 187,843), disclose various 1- (2,6-disubstituted benzoyl) -3-phenylureas having insecticidal activity.

The present invention describes a narrow group of compounds within the general scope of the compounds of the aforementioned Dutch patent application, which have unexpectedly found a strong herbicidal activity which the other compounds of the Dutch application do not exhibit. This is in any doubt confirmed by the comparative efficacy test results of the five compounds of the present invention with the 76 closely related compounds described in the cited Dutch patent application.

The herbicidal compositions of the present invention are therefore novel, have a high novel effect and are an enrichment of the prior art.

Accordingly, the invention provides a herbicidal composition, characterized in that the: active ingredient 1- (2,6-dimethoxybenzoyl) -3- (subst.f) urea of formula I wherein when R ² and R ³ are the same and are methoxy or chlorine, then all R < ⁴ > are hydrogen or, when R < ² > and R < ³ > are fluorine, each R < ⁴ >

The 2,6-dimethoxybenzoylphenylureas of the formula I are prepared in a manner known per se, for example by the preparation of a 2,6-dimethoxybenzoyl derivative of the formula II

is reacted with a substituted benzene of formula III

in which

R ³ , R ³ and R ⁴ are as defined above and one of Q ¹ and Q ² is amino and the other isocyanato.

In accordance with a preferred process, the 2,6-dimethoxybenzoyl derivative is reacted with anhydrous ammonia to give the corresponding benzamide which is reacted with oxalic chloride to give the 2,6-dimethoxybenzoyl isocyanate of formula II wherein Q ¹ is an isocyanato group which is then reacting with the corresponding substituted benzene of formula III, in which Q ² is amino, to give the corresponding 1- (2,6-dimethoxybenzoyl) -3- (substituted phenyl) urea of formula I. This process is illustrated by the following reaction scheme. :

OCH,

OCH \ _

A) - "C" NH ~ C-NH-O R oc _Hi

In the formulas given in this Scheme, the symbols R ^2, R ³ and R · ^{Z 'are} as hereinbefore defined and X is halogen, hydroxyl, alkoxy having 1 to 6 carbon atoms, or an O-C-alkyl wherein alkyl

O contains 1 to 6 carbon atoms.

The final reaction step is generally carried out in a suitable solvent and under an inert atmosphere such as a nitrogen atmosphere. Temperature range suitable for. the addition of reactants may range from 0 to 30 degrees Celsius, with a preferred interval of 10 to 25 ° C when Q ¹ is an isocyanato group, and when Q ¹ is an amino group, the preferred temperature is 25 to 100 ° C. Suitable solvents include ethyl acetate, benzene and the above halogenated solvents, preferably methylene chloride, 1,2-dichloroethane and chloroform.

After addition of the reactants, the temperature of the reaction mixture is generally increased from about 20 ° C to 40 ^° C. If Q ¹ is an amino group, a tertiary amine base, such as triethylamine or pyridine, may optionally be present. The reaction mixture is worked up by standard procedures. Usually, either the precipitated solid product is filtered off or the solvent is evaporated in vacuo. If the solvent needs to be removed, the residue is suspended in a suitable solvent, usually an alcohol, and the solid product is filtered off. The product obtained can be further purified by recrystallization or column chromatography.

The starting substituted anilines and acid chlorides are either commercially available or can be readily prepared by known methods.

A typical preparation of the starting materials used to produce the compounds of formula I is illustrated by the following examples.

2,6-dimethoxybenzamide

To 2.5 liters of diethyl ether was added 200 g

2,6-dimethoxybenzoyl chloride, the solution is cooled to 5 ° C under nitrogen, then the nitrogen introduction is stopped and ammonia gas is introduced into the solution for 2 hours maintaining the temperature between 5 and 10 ^° C. The reaction mixture was stirred for an additional 1 hour while allowing the temperature to rise to about 25 ° C. The resulting solution has a pH of 9.0. The solids were filtered off and stir in 2 liters of water while the pH of the aqueous suspension with ammonium hydroxide ¹ · adjusted to 8.0. The solid material was filtered again and dried after washing with water. 167 g (92%) of the desired product are obtained, which product is used as is in the following stage.

2,6-dimethoxybenzoyl isocyanate

167 g of 2,6-dimethoxybenzamide are stirred in 2 liters of toluene under nitrogen and 145 g of oxalic acid chloride are added over 1 hour. The resulting solution was heated to 60 ° C and maintained at this temperature overnight. Hydrogen chloride is allowed to escape, preventing condensation of water and its access to the reaction mixture.

The reaction mixture was heated to reflux (about 110 ° C) for 1.5 hours while nitrogen was bubbled under the surface of the reaction mixture. The mixture was allowed to cool to about 30 ° C with stirring, the resulting solution was filtered through a pad of diatomaceous earth under nitrogen and the solvent was evaporated in vacuo. 185 g (97%) of an oily product are obtained, which is stored under nitrogen.

Using 2,6-dimethoxybenzoyl isocyanate and an appropriately substituted aniline, compounds of formula (I) can be prepared.

EXAMPLE 1 1- (2,6-Dimethoxybenzoyl) -3- (2,6-dichlorophenyl) urea m.p.

In a reaction flask, 16.2 g of 2,6-dichloroaniline are dissolved in 200 ml of 1,2-dichloroethane under a nitrogen atmosphere at about 25 ° C. 25 g of 2,6-dimethoxybenzoyl isocyanate in 25 ml of 1,2-dichloroethane are added to the solution, and the resulting solution is then heated at 40 ° C for 2 hours after the addition is complete. Chromatography of a sample of the reaction mixture on a thin layer of silica gel in diethyl ether indicated that the mixture no longer contained 2,6-dlchloroaniline. The solvent was evaporated in vacuo, the residue was stirred in methanol, the solid material was filtered off and washed with methanol. 26.5 g (72%) of the desired product is obtained. Analysis for C · _E H | ₄ Cl ₂ N ₂ O ₄ calculated:

% C, 52.02;% H, 3.82;% N, 7.59.

% C, 51.81;% H, 3.69;% N, 7.36.

NMR: S shape signal and number of protons group

3.8 6.7 7.4 10.1 10.9

Example 2

1- (2,6-Dimethoxybenzoyl) -3- (2,6-difluorophenyl) urea g 2,6-Difluoroaniline is dissolved in 1500 ml of methylene chloride, cooled to 10 ° C and 90 g 2 are added dropwise under nitrogen. 6-dimethoxybenzoyl isocyanate in 200 ml of methylene chloride The mixture was stirred at 25 ° C for 3 hours, the solid material was filtered off and washed with water, the filtrate was evaporated to dryness, 150 ml of diethyl ether and 150 ml of ethanol were added. The material was filtered again to give 89.0 g of the desired product (60%), melting at 199-200 ° C.

Analysis: for C _J6 · H ₁₄ F ₂ N ₂ O ₄ Calculated:

% C, 57.15;% H, 4.20;% N, 8.33.

% C, 57.20;% H, 4.36;% N, 8.33.

Following the procedure of Example 2, the following compounds were prepared.

Example 3

1- (2,6-dimethoxybenzoyl) -3- (2,6-dimethoxyphenyl) urea

The title compound melts at 208-210 ° C.

s, 6H d, 2H m, 4H s, 1H s, 1H

2, OCH ₃ p-H on rings 4-H on NH NH rings

Analysis: _e Ci8H2oN ₂ O Calculated:

% C, 59.99;% H, 5.59;% N, 7.77%.

H, 5.39; H, 7.63. Example 4

1- (2,6-Dimethoxybenzoyl) -3- (2,4,6-trifluorophenyl) urea

The title compound melts at 202-203 ° C.

Analysis for creping ₁₃ F ₃ N ₂ O ₄ Calculated:

% C, 54.24;% H, 3.70;% N, 7.91%.

C 54.50, H 4.81, N 8.21.

The following compound can be prepared as described in Example 1.

Example 5

1- (2,6-dimethoxybenzoyl) -3- (2,3,5,6-tetrafluorophenyl) urea m.p.

The title compound melts at 183.5-187 ° C.

Analysis: for C ₁₆ H ₁₂ F ₄ N ₂ O ₄ Calculated '

% C, 51.62;% H, 3.25;% N, 7.53.

% C, 51.44;% H, 3.29;% N, 7.64.

¹ has been found that the novel compounds of formula I have useful herbicidal activity in post-emergence and pre-emergence application against a number of weed species rů.zných. The disclosed compounds can be applied directly to plants when young, but are preferably applied to the soil prior to emergence of the plants. The compounds of the invention may either be applied to the soil using a conventional disc cultivator or gates prior to sowing the desired crop or may be applied to the soil surface before emergence of the plants. In the latter process, the active substances are not incorporated into the soil, but are only allowed to infuse into the soil, for example by means of rain.

The compounds of formula I exhibit activity against a wide variety of different weed species, including the following:

Amaranthus retrofle us Xanthium orientale Ambrosia artemisiifolia Datura stramonium Ipomoea purpurea Echinochloa crusgalli Brassica juncea Setaria viridis Avena sativa Abutilon theophrasti Zinnia elegans Portulaca oleracea Sida spinosa

Dicotomiflorum Bidens frondosa Eclipta juncea Alopecurus myosuroides Galium Aparine Matricaria chamomilla Stellaria media Veronica persica Acanthospermum hispidum Cenchrus echinatus Eleusine indica Richardie brasiliensis Solanum spp.

gooseberry buckwheat bent beetroot ragweed durman virgin cucumber rosebud bloody reed rind corn leg rushed rush green oat deaf abutilon perch purslane cabbage frog psuriasum prickly clover camomile chickweed tussock spike and other species persian eleusin l.

It has also been found that the compounds of formula I are safe for a wide variety of desirable plants, thus exhibiting unique selectivity. Representative examples of useful plant species that tolerate the compounds of the invention, depending on the concentration used, are:

Zea mays

Triticum aestivum Oryza sativa Gossypium hirsutura Hordeum vulgare Sorghum vulgare var. saccharatum Pisum sativum Medicago sativa Cucumis sativus Lycopersicon esculentum Arachis hypogaea Beta vulgaris

Brassica napus

Brassica oleracea capitata

Brassica rapa corn wheat rice barley soybean sorghum sugar peas alfalfa cucumber tomato peanuts oilseed rape oilseed cabbage head turnips

The invention also relates to a method for controlling the growth of undesirable vegetation, characterized in that a herbicidally effective amount of a compound of the aforementioned general formula I is applied to the site at which vegetative growth is to be controlled.

The term "herbicidally effective amount" as used hereinabove means an amount of a compound of formula I that either kills the weed species to be controlled or causes it to stifle. ¹ The amount generally ranges from about 0.056 to about 16.8 kilograms per hectare benzoylphenylureas derivatives. The disclosed compounds are preferably applied at rates of about 0.28 to 8.96 kg / ha. The required concentration of active substance in each case varies depending on the weed species to be controlled, the type of composition, the type of soil, the climatic conditions, etc.

The term "undesirable vegetation" as used herein refers to both weeds and weed seeds present at a site to be treated with a compound of formula I. The active compounds described herein can be applied to the soil to selectively control undesirable plants by: that the weed seeds at the time of germination and emergence also come into contact with the treated to directly control the emerging weeds by contact with the aerial parts of these plants.

The compounds of formula (I) may also be formulated together with a suitable agriculturally acceptable carrier or diluent. These compositions contain, depending on the type of composition desired, from about 0.1 to about 95.0% by weight of the active ingredient. Sprayable compositions are preferred due to the speed and economy of their application.

Powder compositions containing a compound of Formula I generally contain from about 0.1% to about 10% of the compound. Powder formulations are prepared by intimately mixing and finely grinding the active ingredient with an inert solid, such as crushed montmorillonite clay, attapulgite clay, talc, crushed volcanic rock, kaolin clay or other inert, relatively dense and inexpensive materials.

Most of the compositions comprising compounds of formula I is in the form of concentrated compositions for spraying in the form of aqueous dispersions or emulsions containing from about 0.1 to about 10% of a compound of formula I. In ^one water-dispersible or "emulsifiable compositions may be either solids (usually known as wettable powders) or liquid (usually known as emulsifiable concentrates).

A typical wettable powder is a homogeneous mixture of a compound of formula I, an inert carrier, and a surfactant. The concentration of active ingredient is usually from about 25% to 90% by weight. The inert carrier is usually selected from the group of materials including attapulgite clays, montmorillonite clays, diatomaceous clays and purified silicates.

Surfactants, forming about 0.5 why. % to about 10% by weight of the wettable powder is selected from the group consisting of sulfonated lignins, condensed naphthalenesulfonates, and alkyl sulfates.

A typical emulsifiable concentrate contains about 12 to 720 g of a compound of formula I in 1 liter of liquid, the active ingredient being dissolved in a mixture of organic solvents and emulsifiers. The organic solvent is selected for this purpose taking into account its solubility and cost. Useful solvents include aromatic solvents, especially xylenes and aromatic oils. Hydrophilic cosolvents such as cyclohexanone and glycol ethers, for example 2-methoxyethanol, may also be added. Other organic solvents, including terpenic solvents and kerosene, may also be used. Suitable emulsifiers for the preparation of emulsifiable concentrates are selected from the group consisting of alkylbenzene sulfonates, naphthalene sulfonates and nonionic surfactants such as alkylphenol-ethylene oxide addition products, which emulsifiers are used at the same percentages as wettable powders.

The solid granular compositions are suitable for application to the soil of the compounds of formula (I) and contain from 0.1 to 20% by weight of active ingredient. The granules consist of a compound of formula (I) deposited on a granulated inert carrier such as coarse crushed clay having a particle size of about 0.1 to 3 mm. The active ingredient is most effectively applied to the clay by dissolving it in a cheap solvent and applying the solution to a clay of the desired particle size in a suitable mixer.

The active agents are applied to plants by methods common in agrochemistry. Sprayable compositions are easy to apply using any of the many types of sprayers known and available in the art. Self-propelled sprayers, tractor mounted sprayers and trailed sprayers that apply water-dispersed agents by means of calibrated spray nozzles are suitable and effective. Also suitable are volumetric delivery devices that can apply precisely metered amounts of granular compositions to the soil. The operator of the application equipment only needs to take care of adjusting the device to apply an appropriate amount of the water-dispersed or granulated composition per hectare in order to achieve the desired application rate of the active ingredient and to achieve a uniform distribution of this amount on the treated plants.

The following examples serve to illustrate typical herbicidal compositions of the invention.

Wettable powder Concentration concentration (° / o weight)

1- (2,6-dimethoxybenzoyl) -3- (2,4,6-trifluorophenyl) urea 50.0 non-ionic surfactant (Igepal) 5.0 lignosulfonate-based dispersant (Polyfon O) 5.0 precipitated hydrated silica as botnadlo (Zeolex 7) 5.0 clay 35.0

100.0

The components are mixed and ground to a free-flowing powder which can be suspended in water for conventional spray application. Of course, any of the compounds of formula (I) may be used as the active ingredient in the above formulation.

Aqueous suspension concentration component (% by weight)

1- (2,6-dimethoxybenzoyl) -3- (2,6-dichlorophenyl) urea 45.00 anionic surfactant and dispersant based on lignosulfonate (Polyfon H) 5.00 clay-forming agent (Min-u-gel 200) 2, 00 Antifoam (Antifoam C) 0,05 Water 47,95

100.00

The above ingredients are thoroughly mixed and finely ground to form a suitable suspension which is further diluted with water at the application site. Of course, any of the compounds of formula (I) may be used as the active ingredient in the above formulation.

Dust concentration component (% by weight)

1- (2,6-dimethoxybenzoyl) -3- (2,3,5,6-tetrafluorophenyl) urea 5,0 diatomaceous earth (Diatomite) 95,0

The benzoylphenylurea is thoroughly mixed with diatomaceous earth and the mixture is ground to a fine powder with a uniform particle size of about 16 to 40 μΐη. The dusts thus obtained can be applied by a number of conventional methods, for example by air. Of course, any of the compounds of formula (I) may be used as the active ingredient in the above formulation.

Granulate component concentration (° / o weight)

1- (2,6-dimethoxybenzoyl) -3- (2,3,5,6-tetrafluorophenyl) urea 5,0 aromatic oil 5,0 granulated clay (Florex 30/60) 90,0

100.0

The herbicide is dissolved in petroleum and sprayed onto granulated clay, usually with stirring, whereupon the resulting granulate is sieved to a uniform particle size. Of course, any of the compounds of formula (I) may be used as the active ingredient in the above formulation.

The herbicidal activity of representative compounds of formula I is illustrated by the following experiments.

Experiment 1

The compounds of formula I exhibit herbicidal activity. The initial herbicidal activity test was carried out at an active compound concentration of 16.8 kg / ha.

A standard mixture of equal parts of sand and soil is used for the test and sterilized for 24 hours in an autoclave at about 118 ° C. After sterilization, separate soil containers are filled with standard soil mixture into which the seeds of tomato, bloody dew and seedlings bent are sewed in rows. Four days before treatment, the soil in each pot is fertilized with machine fertilizer 23—21—17.

For administration, the test compounds are treated by dissolving 20 mg of the test substance in 2 ml of solvent. The solvent is prepared by adding 1.174 g of Toximul R and 0.783 g of Toximul S (these preparations consist of mixtures of anionic and non-ionic surfactants) to 100 ml of acetone and 100 ml of ethyl alcohol. A solution of the test substance in this solvent is diluted to 8 ml with deionized water and applied postemergence and some preemergence to some sown containers using a modified DeVilbiss atomizer. Postemergence treatment is performed 11 to 13 days after sowing, preemergence treatment is performed 1 day after sowing.

After application of the test compounds, the treated dishes were placed in a greenhouse and according to the invention

100.0 needs are irrigated. About 10 to 13 days after application of the test compounds, the experiments are evaluated, in each case untreated control plants are used as standards. The degree of herbicidal activity is evaluated using a scale 1-5, where level 1 represents no plant damage, level 2 moderate plant damage, level 3 moderate plant damage, level 4 severe plant damage, and level 5 plant destruction or non-emergence. The various types of plant damage are identified by the following letters:

A = abscissae

B = incineration

C - chlorose

D - destruction

E - epinastia

F = formative effects

G = dark green color

I = increase in plant growth

L = local necrosis

N = no germination

P = red pigmentation

R = limited germination

S = stunting

U = unclassified damage

The herbicidal activity of the typical 2,6-dimethoxybenzoylphenylureas according to the invention, evaluated using the test described above, is shown in the following Table I.

In this and the following tables, the compounds of the invention are designated by the Roman numerals I to V according to the following key:

1- (2,6-Dimethoxybenzoyl) -3- (2,6-dichlorophenyl) urea m.p.

II 1- (2,6-Dimethoxybenzoyl) -3- (2,6-difluorophenyl) urea

III 1- (2,6-dimethoxybenzoyl) -3- (2,6-dimethoxyphenyl) urea

IV 1- (2,6-Dimethoxybenzoyl) -3- (2,4,6-trifluorophenyl) urea

1- (2,6-Dimethoixybenzoyl) -3- (2,3,5,6-tetrafluorophenyl) urea

Table I below shows the activity values for the 76 closely related compounds known from Dutch Patent Application No. 7,105,350, as determined in the above-described assay. These substances are designated by numbers 1-76 according to the following key:

1- (2,6-Dimethoxybenzoyl) -3-phenylurea

1- (2,6-difluorobenzoyl) -3- (4-chlorophenyl) urea

1- (2,6-dimethoxybenzoyl) -3- [4- (cyanophenylmethyl) phenyl] urea m.p.

1- (2,6-dimethoxybenzoyl) -3- (2,6-dibromophenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (3,4-dichlorophenyl) urea

1- (2,6-dimethoxybenzoyl) -3- (2,4-dichlorophenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (3-trifluoromethylphenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (4-methylphenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2-methoxyphenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2,6-diethylphenyl) urea m.p.

1- (2,6-Dimethoxybenzoyl) -3- (2-fluorophenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2-tert-butyl-6-methylphenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2-ethyl-6-isopropylphenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2-chloro-6-nitrophenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2,4,6-tribromophenyl) urea

1- (2,6-dimethoxybenzoyl) -3- (2,4,6-trichlorophenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2,6-dimethylphenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2,6-dichloro-4-nitrophenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2-acetylphenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2-ethyl-6-sec-butylphenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2-fluoro-5-trifluoromethylphenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2-ethyl-6-methylphenyl) urea 1- (2,6-Dimethoxybenzoyl) -3-pentachlorophenylurea

1- (2,6-Dimethoxybenzoyl) -3- (2-trifluoromethylphenyl) urea

1- (2,6-dimethoxybenzoyl) -3- [3,5-bis (trifluoromethyl) phenyl] urea m.p.

1- (2,6-dimethoxybenzoyl) -3- (2,4,6-trimethylphenyl) urea m.p.

1- (2,6-Dimethoxybenzoyl) -3- (2-chloro-6-methylphenylurea)

1- (2,6-dimethoxybenzoyl) -3- (3,5-dichlorophenyl) urea m.p.

1- (2,6-dimethoxybenzoyl) -3- (2-methoxy-5-methylphenyl) urea m.p.

1- (2,6-Dimethoxybenzoyl) -3- (2-ethoxycarbonylphenyl) Urea

1- (2,6-Dimethoxybenzoyl) -3- (2-methoxycarbonyl-3,4,5-trimethoxyphenyl) urea

1- (2,6-Dimethoxybenzoyl) -3- (2,6-dichloro-4-methylsulfonylphenyl) urea

1- (2,6-difluorobenzoyl) -3- (2,6-difluorophenyl) urea

1- (2-chloro-6-methoxybenzoyl) -3- (2,6-difluorophenyl) Urea

1- (2-Methoxybenzoyl) -3- (2,6-dichlorophenyl) Urea

1- (2-methoxybenzoyl) -3- (2,6-difluorophenyl) urea

1- (2-chlorobenzoyl) -3- (4-fluoro-3-trifluoromethylphenyl) urea

1- (2,6-dichlorobenzoyl) -3- {2 - [(3,7-dimethyl-2,6-octadienyl) oxy] -5-trifluoromethylphenyl urea

1- (2,6-dichlorobenzoyl) -3- (4 - [(3,7-dimethyl-2,6-octadienyl) oxy] -3-trifluoromethylphenylurea

1- (2,6-difluorobenzoyl) -3- (4-trifluoromethylphenyl) Urea

1- (2,6-Diethoxybenzoyl) -3- (2,6-difluorophenyl) urea

1- (2,6-Dimethylthiobenzoyl) -3- (2,6-difluorophenyl) Urea

1- (2,6-Dimethoxybenzoyl) -3- (2-tert-butyl-6-methylphenyl) -3-methylurea

1- (2,6-dimethoxybenzoyl) -3- (2,6-diethylphenyl) -3-methylurea

1- (2,6-Dimethoxybenzoyl) -3-methyl-3- (2-methyl-6-isopropynyl) urea

1- (2,6-Dimethoxy-benzoyl) -3-methyl-3- (2,4,5-trimethyl-phenyl) -urea

1- (2,6-dimethoxybenzoyl) -3- (2-ethylphenyl) -3-methylurea

1- (2,6-dimethoxybenzoyl) -3-ethyl-3- (2-methylphenyl) urea m.p.

1- (2,6-dimethoxybenzoyl) -3-ethyl 3- (3-methylphenyl) urea m.p.

1- (2,6-Dimethoxybenzoyl) -3- (2,6-dichlorophenyl) -3-ethylurea 1- (2,6-Dimethoxybenzoyl) -3-ethyl-3- (3-trifluoromethylphenyl) Urea

1- (2,6-Dimethoxybenzoyl) -3- (2,6-dichloro-phenyl) -3-methylurea

1-Benzoyl-3- (2,6-dichlorophenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (4-trifluoromethylphenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (2,6-dimethylphenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (2,6-difluorophenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (2-ethyl-6-methylphenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (2,6-dichlorophenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (2-fluoro-5-trifluoromethylphenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (2-chloro-6-methylphenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (2,4,6-trifluorophenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (2-methyl-6-isopropylphenyl) thiourea

1- (2,6-dimethoxybenzoyl) -3- (2,4-difluorophenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (3-trifluoromethylphenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (2-tert-butyl-6-methylphenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (4-fluoro-3-trifluoromethylphenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (2-methyl-6-nitrophenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- (2,3,4,6-tetrafluorophenyl) thiourea

1- (2,6-Dimethoxybenzoyl) -3- [3,5-bis (trifluoromethyl) phenyl] thiourea

1- (2,6-dimethoxybenzoyl) -3- (2,6-dimethoxyphenyl) thiourea

1- (2,6-dimethoxybenzoyl) -3- (2,6-dibromophenyl) thiourea 1- (2,6-dimethoxybenzoyl) -: xyphenyl) thiourea

1- (2,6-dimethoxybenzoyl) thylphenyl) thiourea

1- (2,6-dimethoxybenzoyl) thiophenylylthiourea :-( 2,5-dimethoxy- (2,4-dimime :-( 2,3-dimime) 1- (2,6-dimethoxybenzoyl) -3- (3 (5-dimethoxyphenyl) thiourea

1- (2,6-dimethoxybenzoyl) -3- (2,4-dimethoxyphenyl) thiourea.

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Experiment 2

The herbicidal activity of some of the compounds of the invention at different application rates was assessed by the greenhouse test using a number of different species of test plants. Several other weed and crop species are used to determine the selectivity of herbicidal activity. Test compounds are formulated as described above, dissolving about 4 g of the active compound in 100 ml of a surfactant solvent and diluting with about 12 parts water to about 1 part of this solution prior to sowing.

The results of the pre-emergence herbicidal activity test are shown in Table II, the results of the post-emergence herbicidal activity test are shown in Table III. In these tables, the test plants are abbreviated with the following meanings:

Ku = maize

Ba - cotton So = soybean Ps - wheat Vo = alfalfa Cř = sugar beet Rý = rice O = cucumber Ra = tomato

Jk = hedgehog corns Me - goosefoot Rk = bloody dewberry Bs = rushwort La = amaranth Bé = bér Oh = oat dea = Ab = abutilon

Du = durman virgin cucumber Po - broom Os = ostálka

The doses of the test substances in Tables II and III are reported in kg / ha. In some cases, two or more tests have been performed for a given application rate, and in such cases average values are reported.

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The results show that the compounds I to V of the present invention are very potent herbicides, clearly superior to the related compounds 1-76. The compounds I to V will have such excellent herbicidal activity.

Experiment 3

Field trials of the compound of Example 2 above, namely 2,6-dimethoxybenzoyl) -3- (2,6-difluorophenyl) urea, were also conducted to evaluate herbicidal activity and tolerance for crop plants.

The test substance is processed to 50% wettable powder as follows.

127.2 g of the compound of Example 2 are thoroughly mixed with 19.8 g of Reax 45L (surfactant plus lignosulfonate acting as a combined wetting and dispersing agent), 12.3 g of precipitated silica (Zeolex 7) and 87, 7 g of kaolinite clay and the mixture is ground to a desired particle size in a hammer mill or a mill mill.

The composition thus prepared, after dilution with water in various doses, is applied both to the soil surface and to the soil (with incorporation) before sowing selected species of useful plants and weeds. Damage to the crop plants is assessed visually using a scale of 0-10, where 0 means no damage and 10 represents the destruction of the plant, multiplied by 10 to the percentage of inhibition. For each dose, the experiment is repeated three times and the average percent inhibition observed is shown in the following table. Evaluation is carried out 3 and 6 weeks after sowing (and treatment). The results of this field test are shown in Table IV (topical application) and Table V (pre-sowing application with soil incorporation). A dash (-) in the table indicates that the compound was not tested against the specified plant species at the indicated concentration.

The test plants are indicated in the tables with the following abbreviations:

sorghum or maize Ku rice Rice barley nec wheat Wheatgrass Soybean Soil cotton Ba annual grass Jt abutilon Ab kindly: La bittergrass Po rushing Bs tn

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A field trial was also conducted in the UK to investigate the potency and selectivity of the compound of Example 2 against a wide variety of different crop and weed species. The test substance is formulated into the formulation according to the above general procedure, using Toximul R and S as surfactants and a 1: 1 mixture of acetone and ethanol. The active formulation is then pre-emergence applied to the soil surface. The efficacy of the test compound against barley and wheat crops is determined by comparing the emergence of the crops with the untreated control fields and the ability of the test compound to control certain weed species. The evaluation is performed visually and the herbicidal efficacy is given as a percentage found by comparison with the condition on the untreated control fields. The results obtained are shown in Table VI below.

Table VI

the observed effect number of days after treatment dose applied (kg / ha) efficiency (%) percentage of emerging plants 14 1.0 94.0 barley 0.5 97.0 0.25 91.2 0.125 87.8 untreated control 100.0 28 1.0 0.8 0.5 2.3 0.25 0 0.125 1.6 untreated control 0 28 1.0 97.9 0.5 92.0 0.25 97.9 0.125 97.9 untreated control 100.0 percentage of emerging plants 37 1.0 104.8 barley 0.5 108.5 0.25 111.5 0.125 108.5 untreated control 100.0 percentage of emerging plants 14 1.0 92.4 wheat 0.5 103.2 0.25 103.4 0,125 ' 85.5 untreated control 100.0 28 ...... 1.0 1.3. 0.5 1.0 0.25 0.7 0.125 1.3 untreated control 0.7 28 1.0 96.1 0.5 91.6 0.25 91.6 0.125 91.6 untreated control 100.0 percentage of emerging plants 39 1.0 100.0 wheat 0.5 79.6 0.25 70.9 0.125 79.6 untreated control 100.0 extermination of field fox 28 1.0 2.3 0.5 0 0.25 4.7 0.125 0 untreated control 0

observed effect number of days applied dose efficacy after treatment (kg / haj (%) eradication of bedstraws eradication of bedstraws erupting of chamomiles eradication chickweed eradication chickweed eradication extermination of Persian speedwell

42 1.0 4.7 0.5 0 0.25 1.6 0.125 0 untreated control 0 28 1.0 7.4 0.5 0 0.25 0 0.125 2.9 untreated control 0 42 1.0 14.9 0.5 0 0.25 2.3 0.125 4.7 untreated control 0 28 1.0 100.0 0.5 98.4 0.25 96.3 0.125 52.8 untreated control 0 42 1.0 100.0 0.5 99.2 0.25 97.0 0.125 76.4 untreated control 0 28 1.0 100.0 0.5 100.0 0.25 100.0 0.125 98.4 untreated control 0 42 1.0 100.0 0.5 100.0 0.25 99.2 0.125 70.2 untreated control 0 42 1.0 100.0 0.5 100.0 0.25 85.1 0.125 100.0 untreated control 0

For comparative purposes, a number of greenhouse tests were carried out with the known comparators A to N listed below (trade names are given in brackets):

A. 2-Chloro-4-ethylamino-6-isopropylamino-s-triazine (Aatrex)

B. 2-Chloro-2 ', 6'-diethyl-N- (methoxymethyl) acetanilide (Lasso)

C. 3- (3,4-dichlorophenyl) -1,1-dimethylurea (Karmex)

D. 1,1-Dimethyl-3- (3-trifluoromethylphenyl) urea (Cotoran)

E. 5-Bromo-3- (s-butyl) -6-methyluracil (Hyvar)

G. 2,4-Dichlorophenyl-4-nitrophenyl ether (TOK)

H. 2- (3,4-Dichlorophenyl) -4-methyl-1,2,4-oxadiazolidine-3,5-dlonone (Probe)

I. 2- (t-butyl) -4- (2,4-dichloro-5-isopropoxyphenyl) -A ² -1,3,4-oxadiazolin-5-one (Ronstar)

J. 2,6-dichlorobenzonitrile (Casoron)

K. O-Diisopropylphosphorodithioate S-ester with N- (2-mercaptoethylbenzenesulfonamide) (Prefar)

L. 2- (N-naphthoxy) -N, N-diethylpropionamide (Devrinol)

M. 1,1,1-Trifluoro-N- (2-methyl-4-phenylsulfonylphenyl) methanesulfonamide (Destun)

F. S-Ethyl dipropylthiocarbamate (Eptam)

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Ν. Kiethyl 5- (2,4-dichlorophenoxy) -2-nitrobenzoate (Modown J

The abovementioned comparative compounds were applied in a pre-emergence manner analogous to Example 2, and the results of the experiment were evaluated using a 0 to 0 scale.

10 where 0 means no damage and 10 means complete destruction of plants.

The results obtained are summarized in the following Table VII, in which the test plants are designated with the same abbreviations as in Table II.

Table VII

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active substance application rate (kg / ha) Ba Ku damage rating Só Jk Be After, AND 0.28 0 1 10 7 4 9.5 0.56 2 0 9 7 5 9.8 1.1 10 0 10 8 7 10 (B) 0.28 2 0 0 7 8 0 0.56 1 0 0 8 9 1 1.1 2 1 0 10 10 0 C 0.28 0 0 1 2 9.5 1 0.56 0 0 4 2 6 5 1.1 0 3 10 8 9.8 9.5 D 0.28 1 0 3 3 4 0 0.56 0 0 6 5 9 5 1.1 0 3 9 8 10 9.5 E 0.14 8 1 2 3 6 5 0.28 10 9 9.5 9 9 9.5 0.56 10 7 10 10 10 10 F 0.56 2 1 0 7 6 3 1.1 3 2 3 9 8 4 2.2 5 4 7 9.5 9 9 G 0.28 0 2 0 0 2 1 0.56 0 2 0 0 0 0 1.1 0 2 0 0 4 0 H 0.28 0 0 0 0 5 2 0.56 1 0 Ό 0 5 2 Ll 1 0 0 0 5 3 AND 0.28 0 2 0 2 8 1 0.56 0 2 0 2 10 0 1.1 0 4 0 5 10 2 J 0.28 5 2 0 0 9 2 0.56 10 3 5 4 9.5 4 1.1 10 6 10 9.5 10 5 TO 0.56 0 1 0 5 8 0 1.1 0 1 0 5 9 0 2.2 0 1 0 8 9 0 L 0.28 1 2 0 3 9 0 0.56 1 3 1 5 9 0 1.1 2 4 2 8 10 0 M 0.28 0 0 0 3 7 1 0.56 0 1 0 5 8 2 1.1 0 2 0 7 9 4 N 0.28 0 1 0 0 6 0 0.56 1 0 0 0 6 0 1.1 0 0 0 0 9 0

Claims (7)

SUBJECT 1. A herbicidal composition characterized in that it comprises as active ingredient 1- (2,6-dimethoixybenzoyl) -3- (substituted phenyl) ureas of the formula I, where R ² and R ³ are the same and represent methoxy or chlorine, then all R &lt; ⁴ &gt; are hydrogen, or when R &lt; ² &gt; and R &lt; ³ &gt; are fluorine, each R &lt; ⁴ &gt; independently represents fluorine or hydrogen in combination with one or more agriculturally acceptable carriers or diluents. 2. A composition according to claim 1, characterized in that it comprises as active ingredient sloučey yn A climbing Nin of the above formula I wherein both R ² and R ³ represent fluorine atoms and R ⁴ is defined as in point 1. 3. A composition according to claim 1, characterized in that it contains 1- (2,6-dimethoxybenzoyl) -3- (2,6-dichlorophenyl) urea as the active ingredient of the formula I. 4. A composition according to claim 1, characterized in that it contains 1- (2,6-dimethoxybenzoyl) -3- (2,6-difluorophenyl) urea as the active ingredient of the formula I. 5. A composition according to claim 1, characterized in that it contains 1- (2,6-dimethoxybenzoyl) -3- (2,6-dimethoxyphenyl) urea as the active ingredient of the formula I. 6. A composition according to claim 1, characterized in that it contains 1- (2,6-dimethoxybenzoyl) -3- (2,4,6-trifluorophenyl) urea as the active ingredient of the formula I. 7. A composition according to claim 1, characterized in that it contains 1- (2,6-dimethoxybenzoyl) -3- (2,3,5,6-tetrafluorophenyl) urea as the active ingredient of the formula I.