CS237332B2 - Herbicidal agent - Google Patents

Abstract

Herbicidal composition, characterized in that it contains as an active ingredient a derivative of 1-(2,6-dimethoxybenzoyl)-3-(subst.phenyl) urea of the general formula I if R2 and R3 are the same and represent a methoxy group or a chlorine atom, then all R4 symbols represent hydrogen atoms, or if both R2 and R3 symbols represent fluorine atoms, then the individual R4 symbols independently of each other always represent fluorine or hydrogen, in combination with one or more agriculturally acceptable carriers or diluents.

Description

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

The use of herbicides to control the growth of unwanted vegetation has been the subject of considerable research effort for many years. This control of unwanted vegetation has in many cases a considerable economic effect in agriculture. The continuous use of chemical herbicides is associated with a number of problems, including environmental pollution, tolerance of useful plants, weed resistance, as well as economic aspects. Accordingly, the search for new economically acceptable herbicides that would be selectively toxic to unwanted vegetation is still ongoing.

L-benzoyl-l-phenylureas useful as herbicides are already known. Pillon et al. in U.S. Pat. No. 5,111,111.

No. 384,473 describes the use of various 1-phenyl-1-benzoylureas useful as herbicidal agents. Lehureau et al. in U.S. Patent No. 3,342,586 broadly describe ureas exhibiting herbicidal activity, but only 1-phenyl-1-alkanoylureas are mentioned as a preferred group of such agents. In U.S. Patent No.

166,124 and in Dutch Patent Application No. 7,105,350, published on October 24, 1972 (equivalent to Argentine Patent No. 187,843), various 1-(2,6-disubstituted benzoyl)-3-phenylureas are described which exhibit insecticidal activity.

The invention describes a narrow group of compounds falling within the general scope of the substances disclosed in the above-cited Dutch patent application, which have been unexpectedly found to have a strong herbicidal activity which the other compounds of the Dutch patent application do not exhibit. This fact is demonstrated beyond any doubt by the results of comparative efficacy tests of the five compounds of the invention with 76 closely related substances disclosed in the cited Dutch patent application, given below.

The herbicidal compositions which are the subject of the invention are therefore new, are characterized by a high new effect and represent an enrichment of the prior art.

Accordingly, the subject of the invention is a herbicidal composition, characterized in that: as an active ingredient it contains 1-(2,6-dimethoxybenzoyl)-3-(subst.phenyl) urea of the general formula I in which if R ² and R ³ are the same and represent a methoxy group or a chlorine atom, then all R ⁴ symbols represent hydrogen atoms, or if both R ² and R ³ represent fluorine atoms, then the individual R ⁴ symbols independently of each other always represent fluorine or hydrogen.

2,6-Dimethoxybenzoylphenylureas of the general formula I are prepared in a manner known per se, for example by reacting a 2,6-dimethoxybenzoyl derivative of the general formula II

is reacted with substituted benzene of general formula III

in which

R ³ , R ³ and R ⁴ have the above-mentioned meaning and one of the symbols Q ¹ and Q ² represents an amino group and the other an isocyanato group.

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

OCH,

OCH \_

A )—“C“NH~Č-NH-Ó R oc _Hi

In the formulas shown in this scheme, the symbols R ² , R ³ and R ² ' have the above meaning and X represents a halogen atom, a hydroxy group, an alkoxy group with 1 to 6 carbon atoms or an O-C-alkyl group, where alkyl

O contains 1 to 6 carbon atoms.

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

After addition of the reactants, the temperature of the reaction mixture is usually raised from about 20°C to 40 ^° C. If ^Q1 represents 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, the precipitated solid product is either filtered off or the solvent is evaporated off in vacuo. If it is necessary to remove the solvent, the residue is suspended in a suitable solvent, usually 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.

The following examples illustrate typical preparations of starting materials used to produce compounds of formula I.

2,6-dimethoxybenzamide

To 2.5 liters of diethyl ether is added 200 g

2,6-dimethoxybenzoyl chloride, the solution is cooled to 5 °C under nitrogen, then the introduction of nitrogen is interrupted and gaseous ammonia is introduced into the solution for 2 hours while maintaining the temperature between 5 and 10 ^° C. The reaction mixture is stirred for another 1 hour, while its temperature is allowed to rise to approximately 25 °C. The resulting solution has a pH of 9.0. The solids are filtered off and mixed in 2 liters of water, while the pH of the aqueous suspension is adjusted to 8.0 with ^ammonium hydroxide. The solid material is filtered off again and, after washing with water, dried. 167 g (92%] of the desired product is obtained, which can be used in the next step.

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 to the solution over 1 hour. The resulting solution is 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 (approximately 110 °C) for 1.5 hours, while nitrogen was introduced under the surface using a gas introduction tube. The mixture was allowed to cool to approximately 30 °C with constant stirring, the resulting solution was filtered through a pad of diatomaceous earth under nitrogen, and the solvent was evaporated in vacuo. 185 grams (97%) of an oily product were obtained, which was stored under nitrogen.

Using 2,6-dimethoxybenzoyl isocyanate and aniline which is substituted in each case, it is possible to prepare compounds of the general formula I. The following section provides examples of the preparation of these compounds.

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

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

52.02% C, 3.82% H, 7.59% N, found:

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

NMR: S signal shape and proton number 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 milliliters of methylene chloride, the solution is cooled to 10°C and 90 g of 2,6-dimethoxybenzoyl isocyanate in 200 ml of methylene chloride are added dropwise under a nitrogen atmosphere. The mixture is stirred at 25°C for 3 hours, then the solid material is filtered off and washed with water. The filtrate is evaporated to dryness, 150 ml of diethyl ether and 150 ml of ethanol are added to the residue, and the solid material is filtered off again. 89.0 g of the desired product (60%) are obtained. The product melts at 199-200°C.

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

57.15% C, 4.20% H, 8.33% N, found:

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

The following compounds were prepared according to the procedure of Example 2.

Example 3

1-(2,6-dimethoxybenzoyl)-3-(2,6-dimethoxyphenyl j 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 rings NH NH

Analysis: for Ci8H2oN ₂ O _e calculated:

59.99% C, 5.59% H, 7.77% N, found:

59.70% C, 5.39% H, 7.63% N. Example 4

1-(2,6-dimethoxybenzoyl)-3-(2,4,6-trifluorophenylurea

The title compound melts at 202-203 °C.

Analysis _: for _{C13H13F3N2O4 calculated :}

54.24% C, 3.70% H, 7.91% N, n o 1 p 7pn o·

54.50% C, 4.81% H, 8.21% N.

The following compound can be prepared by the procedure described in Example 1.

Example 5

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

The title compound melts at 183.5 to 187 °C.

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

51.62% C, 3.25% H, 7.53% N, found:

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

It has been found ¹ that the novel compounds of formula I exhibit useful herbicidal activity when applied post-emergence and pre-emergence against a variety of different weed species. The compounds described can be applied directly to the plants when they are young, but are preferably applied to the soil before the plants emerge. The compounds of the invention can either be applied to the soil using a conventional disc cultivator or harrow before sowing the desired crop, or they can be applied to the soil surface before the plants emerge. In this latter process, the active ingredients are not incorporated into the soil, but are simply allowed to leach into it, for example by rain.

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

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

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

white merle, bent leaf ragweed, datura, virgin cucumber, blood-red sundew, cowslip, sedge, green oat, deaf abutilon, common purslane, cabbage purslane, field dogwood, field bindweed, chamomile, bird's-foot trefoil, Persian eleusinian eggplant and against a number of other species including unwanted weeds and grassy weeds.

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 relatively tolerant to the compounds of the invention, depending on the concentration used, include:

Zea mays

Triticum aestivum Oryza sativa Hordeum vulgare Glycine max Gossypium hirsutura 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 cotton sorghum sugar peas alfalfa cucumber tomato peanuts oil beet sugar canola oil cabbage turnips

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

The term "herbicidally effective amount" as used above means that amount of a compound of formula I which either kills the weed species to be controlled or causes stunting of their growth. ^This amount generally ranges from about 0.056 to about 16.8 kg of benzoylphenylurea derivative per hectare. The compounds described are preferably applied at rates of about 0.28 to 8.96 kg/ha. The required concentration of active ingredient in any given case varies depending on the weed species to be controlled, the type of composition, the type of soil, climatic conditions, etc.

The term "undesirable vegetation" used above refers to both weeds and weed seeds that are present on the site to be treated with the compound of general formula I. The described active ingredients can be applied to the soil for the selective destruction of unwanted plants, which occurs when weed seeds come into contact with the treated plant during germination and emergence, or can be used for the direct destruction of emerging weeds by contact with the above-ground parts of these plants.

The compounds of the general formula I can also be processed together with a suitable, agriculturally usable carrier or diluent to form appropriate compositions. These compositions contain, depending on the desired type of composition, from about 0.1 to about 95.0% by weight of active ingredient. Compositions that can be applied by spraying are preferred, due to the speed and economy of their application.

Powder compositions containing a compound of formula I usually contain from about 0.1 to about 10% of the compound. Powder compositions 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 compositions containing compounds of formula I are in the form of concentrated compositions for spray application in the form of aqueous dispersions or emulsions containing about 0.1 to about 10% of the compound of formula ^I. Water-dispersible or emulsifiable compositions can be either solid (commonly known as wettable powders) or liquid (commonly known as emulsifiable concentrates).

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

The surfactants, constituting about 0.5% to about 10% by weight of the wettable powder, are selected from the group consisting of sulfonated lignins, condensed naphthalene sulfonates, and alkyl sulfates.

A typical emulsifiable concentrate contains about 12 to 720 g of a compound of the general formula I in 1 liter of liquid, the active ingredient being dissolved in a mixture of organic solvents and emulsifiers. The organic solvent is chosen for this purpose taking into account its dissolving power and cost. Among the solvents that can be used are aromatic solvents, in particular xylenes and aromatic petroleums. Hydrophilic auxiliary solvents, such as cyclohexanone and glycol ethers, for example 2-methoxyethanol, can also be added. Other organic solvents can also be used, including terpenic solvents and petroleum. Suitable emulsifiers for the preparation of emulsifiable concentrates are selected from the group comprising alkylbenzenesulfonates, naphthalenesulfonates and nonionic surfactants, such as addition products of alkylphenols with ethylene oxide, these emulsifiers being used in the same percentage concentrations as in the case of wettable powders.

Solid granular compositions are suitable for applying compounds of the general formula I to soil and contain the active ingredient in an amount of about 0.1 to 20% by weight. The granules consist of a compound of the general formula I applied to a granular inert carrier, such as coarsely ground clay with a particle size of about 0.1 to 3 mm. The active ingredient is most conveniently applied to this clay by dissolving it in an inexpensive solvent and applying the solution to the clay of the desired particle size in a suitable mixer.

The active agents are applied to the plants by methods conventional in agrochemistry. Sprayable agents are easily applied using any of the numerous types of sprayers known and available in the art. Self-propelled sprayers, tractor-mounted sprayers and trailed sprayers which apply water-dispersed agents by means of calibrated spray nozzles are suitable and effective. Metered application devices which can apply precisely measured amounts of granular agents to the soil are also suitable. The operator of the application device only needs to take care to set the device to apply the appropriate amount of water-dispersed or granular agent per hectare to achieve the desired application rate of active ingredient and to achieve uniform distribution of this amount over the treated plants.

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

Wettable powder component concentration (%/o weight)

1-(2,6-dimethoxybenzoyl)-3-(2,4,6-trifluorophenyl) urea 50.0 nonionic wetting agent (Igepal) 5.0 lignosulfonate-based dispersant (Polyfon O) 5.0 precipitated hydrated silica as swelling agent (Zeolex 7) 5.0 clay 35.0

100.0

The individual components are mixed and ground into a free-flowing powder which can be suspended in water for conventional spray application. Any of the compounds of general formula I can of course be used as the active ingredient in the above-mentioned composition.

Aqueous suspension component concentration (% by weight]

1-(2,6-dimethoxybenzoyl)-3-(2,6-dichlorophenyl) urea 45.00 anionic wetting and dispersing agent based on lignosulfonate (Polyfon H) 5.00 clay-type gelling agent (Min-u-gel 200) 2.00 antifoam additive (Antifoam C) 0.05 water 47.95

100.00

The above-mentioned ingredients are thoroughly mixed and finely ground to form a suitable suspension, which is further diluted with water at the site of application. As an active substance in the above-mentioned composition, it is of course possible to use any of the compounds of general formula I.

Dust component concentration (% by weight)

1-(2,6-dimethoxybenzoyl j -3-(2,3,5,6-tetrafluorophenyl)urea 5.0 infusoria clay (diatomite) 95.0

Benzoylphenylurea is thoroughly mixed with diatomaceous earth and the mixture is ground to a fine powder with a uniform particle size of approximately 16 to 40 μΐη. The dust thus obtained can be applied by a number of conventional methods, for example by air. As an active ingredient in the above-mentioned composition, it is of course possible to use any of the compounds of general formula I.

Granule component concentration (% by weight)

1-(2,6-dimethoxybenzoyl)-3-(2,3,5,6-tetrafluorophenylurea 5.0 aromatic petroleum 5.0 granular clay (Florex 30/60) 90.0

100.0

The herbicidally active substance is dissolved in petroleum and sprayed onto the granulated clay, usually with stirring, after which the resulting granulate is sieved to a uniform particle size. As the active substance in the above composition, it is of course possible to use any of the compounds of general formula I.

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

Attempt 1

The compounds of the general formula I exhibit herbicidal activity. The initial herbicidal activity test is carried out with an active ingredient concentration of 16.8 kg/ha.

The test uses a standard mixture of equal parts sand and soil, which is sterilized for 24 hours in an autoclave at a temperature of approximately 118 °C. After sterilization, separate containers are filled with the standard soil mixture, into which tomato, blood-sown sundew and bent-leafed sweet clover seeds are sown in rows. Four days before treatment, the soil in each container is fertilized with a synthetic fertilizer 23—21—17.

For application, the test compounds are prepared 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 are mixtures of anionic and nonionic surfactants) to 100 ml of acetone and 100 ml of ethyl alcohol. The solution of the test substance in this solvent is diluted with deionized water to a volume of 8 ml and, using a modified DeVilbiss atomizer, is applied to some of the sown containers post-emergence and to some pre-emergence. Post-emergence treatment is carried out 11 to 13 days after sowing, pre-emergence treatment is carried out 1 day after sowing.

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

100.0 needs are irrigated. Approximately 10 to 13 days after application of the test compounds, the experiments are evaluated, in each case using untreated control plants as standards. The degree of herbicidal activity is evaluated using a scale of 1 to 5, where grade 1 represents no plant damage, grade 2 slight plant damage, grade 3 moderate plant damage, grade 4 severe plant damage, and grade 5 plant destruction or failure to emerge. The different types of plant damage are indicated by the following letters:

A = abscissa of the leaves

B = burn

C — chlorosis

D — destruction

E — epinasty

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

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

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

II 1-(2,6-dimethoxybenzoyl)-3-(2,6-difluorophenylurea

III 1-(2,6-dimethoxybenzoyl)-3-(2,6-dimethoxyphenylurea

IV 1-(2,6-dimethoxybenzoyl j -3-(2,4,6-trifluorophenyl j urea

V 1-(2,6-dimethoxybenzoyl)-3-(2,3,5,6-tetrafluorophenyl)urea

Table I below shows the potency values for 76 closely related compounds known from published Dutch patent application No. 7,105,350, determined in the above-described test. These substances are designated by the numbers 1-76 according to the following key:

1-(2,6-dimethoxybenzoyl j -3-phenylurea

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

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

1-(2,6-dimethoxybenzoyl)-3-(2,6-dibromophenylurea

1-(2,6-dimethoxybenzoyl j -3-(3,4-dichlorophenylurea

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

1-(2,6-dimethoxybenzoyl)-3-(3-trifluoromethylphenylurea

1-(2,6-dimethoxybenzoyl j -3-(4-methylphenylurea

1-(2,6-dimethoxybenzoyl j -3-(2-methoxyphenylurea

1-(2,6-dimethoxybenzoyl)-3-(2,6-diethylphenylurea

1-(2,6-dimethoxybenzoyl)-3-(2-fluorophenylurea

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

1-(2,6-dimethoxybenzoyl)-3-(2-ethyl-6-isopropylphenylurea)

1-(2,6-dimethoxybenzoyl)-3-(2-chloro-6-nitrophenylurea)

1-(2,6-dimethoxybenzoyl)-3-(2,4,6-tribromophenylurea)

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

1-(2,6-dimethoxybenzoyl j -3-(2,6-dimethylphenylurea

1-(2,6-dimethoxybenzoyl)-3-(2,6-dichloro-4-nitrophenylurea

1-(2,6-dimethoxybenzoyl j -3-(2-acetylphenyl urea

1-(2,6-dimethoxybenzoyl j -3-(2-ethyl-6-sec.butylphenylurea

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

1-(2,6-dimethoxybenzoyl j -3-(2-ethyl-6-methylphenylurea) l-(2,6-dimethoxybenzol)-3-pentachlorophenylurea

1-(2,6-dimethoxybenzoyl)-3-(2-trifluoromethylphenylurea

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

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

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

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

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

1- (2,6-dimethoxybenzoyl)-3-(2-ethoxycarbonylenyl) 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-trifluoromethylphenylurea

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-difluorophenylurea

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-isopropylenyl)urea

1-(2,Q-dimethyloxybenzoyl)-3-methyl-3-(2,4,5-trimethylphenyl)urea

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

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

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

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-dichlorophenyl)-3-methylurea

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

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

1-(2,6-dimethoxybenzoyl)-3-(2,6-dimethylphenylthiourea)

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-rnethylphenyl)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-Uimethoxybenzoyl)-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-dibromo·phenyl)thiourea 1-(2,6-dimethoxybenzoyl)-(xyphenyl)thiourea

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

1-(2,6-dimethoxybenzoyl)thylphenyl thioureab :-(2,5-dimetho 1-(2,4-dime):-(2,3-dime) 1-(2,6-dimethoxybenzoyl)-3-(3,5-dimethoxyphenyl)thiourea

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

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The herbicidal efficacy of some of the compounds according to the invention at different application rates was evaluated in a greenhouse test using a larger number of different types of test plants. Several other types of weeds and useful plants are used to determine the selectivity of herbicidal efficacy. The tested compounds are prepared into the appropriate compositions in the manner described above, with approximately 4 g of the active compound dissolved in 100 ml of a solvent containing a surfactant and approximately 1 part of this solution diluted with 12 parts of water before application to the seeded dishes.

The results of the herbicidal efficacy test for pre-emergence application are given in Table II below, and the results of the herbicidal efficacy test for post-emergence application are given in Table III. In these tables, the test plants are indicated by abbreviations with the following meanings:

Corn = corn

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

Jk = hedgehog's foot Me — merlík Rk = blood-red sundew Bs = net-like brassica La = honeysuckle Bé = bér Oh = deaf oats Ab = abutilon

Du = datura virgin cucumber Po — bindweed Os = ostalka

The doses of the test substances in Tables II and III are given in kg/ha. In some cases two or more tests were carried out for a given application rate and in such cases the average values are given.

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The results show that compounds I to V according to the invention are very effective herbicides, clearly superior to related compounds 1 to 76. The herbicidal activity of compounds I to V could not have been expected in advance, since none of the characteristic properties of compounds 1 to 76 indicated that compounds I to V would have such excellent herbicidal activity.

Attempt 3

Field trials are also conducted with the compound of Example 2 above, which is 1-(2,6-dimethoxybenzoyl)-3-(2,6-difluorophenyl)urea, to evaluate the herbicidal efficacy and tolerability for cultivated plants.

The test substance is processed into a 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 kaolinitic clay and the mixture is ground in a hammer mill or fluid bed mill to the desired particle size.

The composition prepared in this way, after dilution with water, is applied in various doses both to the soil surface and to the soil (with incorporation) before sowing of selected species of useful plants and weeds. Damage to useful plants is evaluated visually using a scale of 0 to 10, where 0 means no damage and 10 represents the destruction of the plant, while to convert to a percentage of inhibition this number is multiplied by ten. For each dose, the experiment is repeated three times and the average inhibition in percentage is shown in the following table. The evaluation is carried out 3 and 6 weeks after sowing (and treatment). The results of this field test are shown in the following table IV (surface application) and table V (pre-sowing application with incorporation into the soil). A dash ( —) in the table means that the compound has not been tested at the indicated concentration against the indicated species of plant.

Experimental plants are indicated in the tables by the following abbreviations:

sorghum Or corn Ku rice Ry barley jn wheat Psh soybean So cotton Ba annual grasses Jt abutilon Ab kinder: La sedge Po rutabaga Bs tn

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A field trial was also conducted in Great Britain to determine the efficacy and selectivity of the compound of Example 2 against a wide variety of different species of useful plants and weeds. The test substance is prepared into the appropriate composition by the general procedure described above, using Toximul R and S as surfactants and a mixture of acetone and ethanol in a 1:1 ratio. The effective composition is then applied pre-emergence to the soil surface. The efficacy of the test compound against the useful plants barley and wheat is determined by comparing the emergence of these useful plants with the condition in untreated control plots, as well as the ability of the test compound to kill certain types of weeds. The evaluation is carried out visually and the herbicidal efficacy is given in percentages determined by comparison with the condition in untreated control plots. The results obtained are shown in the following Table VI.

Table VI

detected effect number of days after treatment applied dose (kg/haj efficiency (%) percentage of plants that emerged 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 plants that emerged 37 1.0 104.8 barley 0.5 108.5 0.25 111.5 0.125 108.5 untreated control 100.0 percentage of plants that emerged 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 plants that emerged 39 1.0 100.0 wheat 0.5 79.6 0.25 70.9 0.125 79.6 untreated control 100.0 extermination of the field dogfish 28 1.0 2.3 0.5 0 0.25 4.7 0.125 0 untreated control 0

effect observed number of days applied dose efficacy after treatment (kg/ha) eradication of common knotweed eradication of common knotweed eradication of chamomile eradication of bird's-foot trefoil eradication of bird's-foot trefoil eradication of Persian knotweed

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 series of greenhouse tests were carried out with the following known comparators A to N (trade names are given in brackets):

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

B. 2-chloro-2',6'-diethyl-N-(methoxymethylacetanilide (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-dlone (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. 0,0-diisopropyl phosphorodithioate S-ester with N-(2-mercaptoethyl jbenzenesulfonamide (Prefar)

L. 2-(«-Naphthoxy)-N,N-diethylpropionamide (Devrinol)

M. 1,1,1-trifluoro-N-(2-methyl-4-phenylsulfonylphenyl jmethanesulfonamide (Destun)

F. S-ethyldipropylthiocarbamate (Eptam)

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N. Kethyl-5-(2,4-dichlorophenoxy)-2-nitrobenzoate (ModownJ

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

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 experimental plants are designated by the same abbreviations as in Table II.

Table VII

Efficacy in pre-emergence application

active substance applied dose (kg/ha) Yes To damage level Só Jk Be Mon, A 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 I 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.