CS237340B2 - Herbicide agent - Google Patents

Abstract

A herbicidal composition characterized in that that it contains a combination as an active ingredient a compound of formula (I) in which both R * 1 symbols are the same and mean methyl or ethyl; R2 and R3 are the same and represent a fluorine atom, chlorine atom or bromine atom and a second herbicide selected from the group consisting of including α, «, α-trifluoro-2,6-dinitro-N, N-dipropyl-p-toluidine, N-ethyl-N- (2-methyl-2- -propenyl J -2,6-dinitro-4- (trifluoromethyl) - benzenamine and 3,5-dinitro-4-dipropylaminophenylsulfonamide, in weight ratio the compound of formula I to the other herbicide from 4: 1 to 1: 3, along with one or several agriculturally usable carriers or diluents.

Description

(54) Herbicidal product

2

A herbicidal composition comprising, as an active ingredient, a combination of a compound of formula (I)

wherein both R ^{* 1} are the same and are methyl or ethyl and

R ² and R ³ are the same and are fluorine, chlorine or bromine, and a second herbicide selected from the group consisting of α ',,, α-trifluoro-2,6-dinitro-N, N-dipropyl-p-toluidine, N-ethyl-N- (2-methyl-2-propenyl) -2,6-dinitro-4- (trifluoromethyl) benzenamine and 3,5-dinitro-4-dipropylaminophenylsulfonamide, in a weight ratio of the compound of formula I to the second herbicide from 4: 1 to 1: 3, together with one or more agriculturally acceptable carriers or diluents.

The invention relates to a group of novel 1-substituted benzoyl-3-substituted phenyl ureas which have been found to act as herbicides, and to combinations thereof with known active compounds.

The use of herbicides to combat the growth of unwanted vegetation has been the subject of considerable research efforts for many years. In many cases, combating undesirable vegetation has a considerable economic effect. However, the constant use of chemical herbicides poses a number of problems, 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 have long been known. Pillon et al. 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

166,124 and Dutch Patent No. 7,105,350 disclose various 1- (2,6-dihalobenzoyl) -3-phenylureas having insecticidal activity.

The invention provides compounds of formula I

wherein both R ¹ are the same and are methyl or ethyl and

R ² and R ³ are identical and represent fluorine, chlorine or bromine.

A preferred group of compounds are those compounds of formula I wherein R ¹ is methyl and both R ² and 'R ³ represents a fluorine atom.

The present invention provides combination herbicidal compositions containing the above compounds as one component of the active ingredient.

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

is reacted with a substituted benzene of formula III

in which

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

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

In the formulas shown in this scheme, R ¹ , R ² and R ^{3 are} as defined above and X is halogen, hydroxy, C 1 -C 6 alkoxy, or -O-C-alkyl,

II o

wherein the alkyl 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. The temperature range suitable for the addition of the reactants may range from 0 to 30 ° C, 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 30 ° C. 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. When 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 the formula is illustrated by the following examples.

2,6-dimethoxybenzamide

To 2.5 liters of diethyl ether was added 200 g

2,6-methoxybenzoyl 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 hours while 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 and stirred in 2 liters of water, adjusting the pH of the aqueous suspension to 8.0 with ammonium hydroxide. 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 warmed to 60 ° C and kept at this temperature for 24 hours. 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 the appropriate 2,6-dialkoxybenzoyl isocyanate and substituted aniline, the compounds of formula (I) can be prepared.

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 under a nitrogen atmosphere at about 25 ° C. 25 g of 2,6-dimethoxybenzoyl isocyanate in 25 ml of 1,2-dichloroethane were added to the obtained solution, and the resulting solution was heated to 40 ° C for 2 hours after the addition was complete. TLC analysis of silica gel in diethyl ether indicated no 2,6-dichloroaniline. 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 are obtained. Analysis:

Calcd for C16H14Cl2N2O4

% H, 3.82;% N, 7.59; found

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

NMR:

with signal shape and number of protons group 3.8 s, 6H 2, OCH 3 6.7 d, 2H p-H on circles 7.4 m, 4H 4-H on circles 10.1 s, 1H NH 10.9 s, 1H NH

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 added dropwise under nitrogen. 90 g of 2,6-dimethoxybenzoyl isocyanate in 200 ml of methylene chloride. The mixture was stirred at 25 ° C for 3 hours, then the solid material was 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 again. 89.0 g of the desired product (60%) are obtained. The product melts at 199-200 ° C.

Analysis calculated for C16H14F2N2O4

H, 4.20; N, 8.33. found

% 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-dibromophenyl) urea

The title compound melts at 214-215 ° C.

Analysis:

for C 16 H 14 Br 2 N 2 O 4 calculated

% H, 3.08;% N, 6.12; found

H, 2.93; N, 5.98.

Example 4 1- (2,6-Diethoxybenzoyl) -3- (2,6-difluorophenyl) urea

The title compound melts at 129-130 ° C.

Analysis calculated for C18H18F2N2O4

% C, 59.34;% H, 4.98;% N, 7.69;

% H, 5.10;% N, 7.52.

The novel compounds of formula (I) have been found to have useful herbicidal activity in post-emergence and pre-emergence application against a number of different weed species. The disclosed compounds can be applied directly to plants when young, but are preferably applied to the soil prior to emergence of the plants. These compounds may either be applied to the soil using a conventional disc cultivator or harrow 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, and 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:

Chenopodium album Amaranthus retroflexus Xanthium orientale Ambrosia arimisiifolia Datura stramonium Ipomoea purpurea Echinochloa crus galii Brassica juncea Setaria viridis Avena sativa Abutilon theophrasti Zinia elegans

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

gooseberry white pigweed bent beetroot ragweed durman virgin cucumber rosebud bloody hedgehog corn leg crucifer sitinaceae green oat deaf abutilon perch purslane cabbage frog psill field prickly camomile chickweed tussock spike and undesirable species persian eleusely lilac.

It has also been found that the compounds of formula (I) are safe for a wide variety of desirable plants, so that they exhibit Zea mays Triticum aestivum

Oryza sativa Gossypium hirsutum Sorghum vulgare var.

Saccharatum Pisum sativum Medicago sativa Lycopersicon esculentum Arachis hypogaea Beta vulgaris Brassica napus Brassica oleracea capitata Brassica rapa

As mentioned above, the compounds of formula (I) may be used in combination with other herbicides. Such combinations are advantageous when a wider spectrum of herbicidal activity against undesirable vegetation is desirable than can be achieved by using the herbicide alone according to the unique selectivity. Representative examples of useful plant species that tolerate the compounds of the invention, depending on the concentration used, are:

corn wheat rice barley soy cotton sorghum sugar peas alfalfa cucumber tomato peanuts oilseed rape oilseed cabbage head turnips finding. For example, the compounds of the invention may be combined with herbicides to control grass plants. Preferred grass weed herbicides for use in the combinations of the present invention include trifluralin, i.e., α, α, α-trifluoro-2,6-dinitro-N, N-dipropyl-β-toluidine of the formula

ethalfluralin, ie N-ethyl-N- (2-methyl-2-propenyl) -2,6-dinitro-4- (trifluoromethyl) benzenamine of the formula

and oryzalin, i.e., 3,5-dinitro-4-dipropylaminophenylsulfonamide of the formula

The most preferred combination of the invention consists of trifluralin and 1- (2,6-dimethoxybenzoyl) -3- (2,6-difluorophenyl) urea.

The invention also relates to a method of controlling undesirable plants, characterized in that a combination of a benzoylphenylurea of the formula I together with another herbicide, in an effective amount inhibiting the growth of the plants, is applied to these plants. The application rate required for each individual herbicide in the above combination depends on a number of factors, including the type of weeds and grasses to be controlled, the type of herbicides to be used in combination, the climatic and soil conditions, the weed population and related factors. In general, the compounds of the invention are used in combination with other herbicides in a ratio of about 1 to 10 parts by weight of the benzoylphenyl urea of the invention to about 10 to 1 part by weight of the other herbicide. Preferably, these active compound ratios range from 1 to 4 parts by weight of the compound of the formula I to 3 to 1 part by weight of the further herbicide. A particularly preferred combination comprises the individual games of the bicidally active ingredient in a weight ratio of about 1: 1. The combinations of the invention are applied in doses effective to kill unwanted plants to the desired extent.

These doses generally range from about 0.056 to about 16.8 kg of active ingredient per hectare. The disclosed active ingredients are preferably applied at rates of about 0.28 to 8.96 kg / ha. The required concentration of the active ingredient in each case varies depending on the weed species to be controlled, the type of composition, the type of soil, the climatic conditions and the like.

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 in combination with another herbicide. The disclosed active ingredients can be applied to the soil to selectively control unwanted plants by causing the weed seeds to come into contact with the treated soil at the time of germination and emergence. The active ingredients of the invention can also be used to directly control emerging weeds by contact with aerial parts of these plants.

The active ingredients according to the invention can 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 formulations usually contain from about 0.1 to 10% active ingredient. 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 containing the active ingredients of the present invention are in the form of concentrated sprayable compositions in the form of aqueous dispersions or emulsions containing about 0.1 to about 10% of the active ingredient. The water dispersible or emulsifiable compositions may be either solid (usually known as wettable powders) or liquid (usually known as emulsifiable concentrates).

A typical wettable powder is a homogeneous mixture of active ingredient, inert carrier and surfactants. 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. The surfactants, from about 0.5% to about 10% by weight of the wettable powder, are selected from the group consisting of sulfonated lignins, condensed naphthalenesulfonates, and alkyl sulfates.

A typical emulsifiable concentrate contains about 12 to 720 g of active ingredient per 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 addition products with ethylene oxide, the emulsifiers being used at the same percentages as wettable powders.

Solid granular compositions are suitable for application to the soil and contain the active ingredient in an amount of about 0.1 to 20% by weight. The granules consist of the active ingredient deposited on a granular inert carrier, such as coarse crushed clay having a particle size of about 0.1 to 3 mm. The active ingredient is most conveniently applied to this 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 applicator only needs to be careful to adjust 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 the desired application rate of the active ingredient, treated plants.

The active compounds of the combinations according to the invention can be mixed as such and then formulated together, or they can be individually formulated into suitable formulations and then applied as a combination or individually to the locus of undesirable plants.

The following examples serve to illustrate typical herbicidal compositions containing the compound of Formula I alone as the active ingredient

Wettable powder Concentration concentration (% by weight) 1- (2,6-dimethoxybenzoyl) -3- (2,6-difluorophenyl) urea 50.0 non-ionic surfactant (Igepalj 5.0 lignosulfonate dispersant (Polyphon O) 5.0 precipitated hydrated oxide Silica as botnadle (Zeolex 7) 5.0 clay 35.0

---- The individual 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) or a combination thereof with another herbicide may be used as the active ingredient in the above formulation.

Aqueous suspension concentration component (% w / w)

1- J 2,6-dimethoxybenzoyl J-3-

- (2,6-dichlorophenyl) urea 45,00 anionic surfactant and dispersant based on lignosulfonate (Polyphon HJ 5.00 clay-type gelling agent (Min-u-gel 200) 2.00 anti-foam additive (Antifoam C) 0.05 water 47.95 100.00

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

Dust concentration component (% by weight)

1- (2,6-Dimethoxybenzoyl) -3- (2,6-difluorophenyl) urea 5.00

Diatomite clay (Diatomite 95,00

WOO

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 µm. 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) or a combination thereof with another herbicide may be used as the active ingredient in the above formulation.

Granulate concentration component (% by weight)

1- (2,6-dimethoxybenzoyl) -3- (2,6-difluorophenyl) 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) or a combination thereof with another herbicide may be used as the active ingredient in the above formulation.

The following is an example of a typical herbicidal composition comprising a combination of the invention.

Tank-mix preparation ingredient% by weight

1- (2,6-dimethoxybenzoyl) -3- (2,6-difluorophenyl) urea as 50% wettable powder 60.0 trifluralin as granular concentrate (480 g / liter) 40.0

100.0

A wettable powder containing 50% by weight of the active compound of the formula I is introduced into water and an emulsifiable concentrate containing 480 g of triflurallin per liter is added to the mixture while stirring. The resulting mixture is sprayed onto the soil surface, whereupon it is usually incorporated to a depth of approx

7.5 to 10 cm.

The following field trials illustrate the herbicidal activity of representative combinations of the invention.

Experiment 1

A field experiment was carried out using the compound of Example 2 above and trifluralin as active ingredients. For use in this experiment, a tank-mix formulation was prepared from these active ingredients by adding the compound of Example 2 as a 50% wettable powder to water with stirring and mixing this with an emulsifiable concentrate containing 480 g of trifluralin per liter. This combined preparation is incorporated into the soil to a depth of 7.5 centimeters before sowing and on the same day the treated soil is sown with soybean and cotton. The results shown in Table I are expressed as percent inhibition.

Table I

Efficacy of a combination of the compound of Example 2 and trifluralin

application rate (kg / ha) of the compound of Example 2 + trifluralin number of days after sowing soya inhibition in% cotton durman bér beet 2.24 + 0.56 20 May 0.3 5.0 100.0 97.5 99.5 35 0 0 100.0 97.5 98.2 1.68 + 0.56 20 May 0 0 98.8 100.0 99.7 35 0 0 97.5 98.8 98.8 1.12 + 0.56 20 May 0 0 98.2 99.0 98.0 ·> · '· 35 0 0 94.5 95.7 94.5 0.56 + 0.56 20 May 0 0 93.8 100.0 93.5 35 0 0 73.8 99.5 87.5

3 7 3 4 1

Experiment 2

A field trial was also conducted in Mississippi using a combination of the compound of Example 2 and trifluralin in cotton against a wide variety of different weed species. A tank-mix preparation was prepared from the combination of active ingredients, which was incorporated into the soil before sowing as in the previous experiment. The crop was sown 5 days after treatment.

The results obtained in this test are shown in Table II below

Table II

the observed effect number of days after treatment application rate (kg / haj of Example 2 + trifluralin efficiency damage to cotton plants 40 2.24 + 0.84 0 5 to 7.5 cm high 1.68 -j- 0.84 0 1.12 + 0.84 0 0.84 + 0.84 0 0.56 + 0.84 0 0.28 4- 0.84 0 untreated control 0 damage to cotton plants 90 2.24 + 0.84 0 early in flowering 1.68 -j- 0.84 0 1.12 + 0.84 0 0.84 + 0.84 0 0.56 + 0.84 0 - 0.28 4- 0.84 0 untreated control 0 damage to cotton plants 181 2.24 + 0.84 0 having 50 to 60% capsules 1.68 4- 0.84 0 open 1.12 4- 0.84 0 0.84 4- 0.84 0 0.56 4- 0.84 0 0.28 + 0.84 0 untreated control 0 number of cotton plants 51 2.24 + 0.84 109.7 always on two 3 meters 1.68 + 0.84 102.6 lines 1.12 4- 0.84 97.4 0.84 4- 0.84 90.3 0.56 + 0.84 102.6 0.28 -4 0.84 95.4 untreated control 100.0 Cotton seed yield 195 2.24 + 0.84 116.7 always from an area of 29.5 m ² 1.68 -4 0.84 134.4 1.12 -4 0.84 126.7 0.84 4- 0.84 132.2 0.56 4- 0.84 118.9 0.28 4- 0.84 113.3 untreated control 100.0 extermination of amaranth 40 2.24 + 0.84 100.0 1.68 4- 0.84 100.0 1.12 4- 0.84 100.0 0.84 4- 0.84 100.0 0.56 + 0.84 100.0 0.28 4- 0.84 100.0 untreated control 0 90 2.24 + 0.84 100.0 1.68 + 0.84 100.0 1.12 + 0.84 100.0 0.84 4- 0.84 100.0 0.56 + 0.84 100.0 0.28 + 0.84 100.0 untreated control 0 181 2.24 + 0.84 100.0 1.68 4- 0.84 100.0 1.12 + 0.84 100.0 0.84 4- 0.84 . 100.0

observed effect number applied rate (kg / ha) efficacy (%) days after compound of example 2 treatment + trifluralin pectoral eradication eradication of the perin

0.56 + 0.84 100.0 0.28 + 0.84 100.0 untreated control 0 2.24 + 0.84 100.0 1.68 + 0.84 100.0 1.12 + 0.84 100.0 0.84 0.84 100.0 0.56 + 0.84 98.3 0.28 4- 0.84 100.0 untreated control 0 2.24 + 0.84 100.0 1.68 + 0.84 100.0 1.12 + 0.84 100.0 0.84 4- 0.84 100.0 0.56 4- 0.84 100.0 0.28 4- 0.84 93.3 untreated control 0 2.24 + 0.84 100.0 1.68 4- 0.84 99.3 1.12 4- 0.84 100.0 0.84 4- 0.84 100.0 0.56 4- 0.84 100.0 0.28 + 0.84 100.0 untreated control 0 2.24 + 0.84 33.3. 1.68 4 “0.84 6.7 1.12 4- 0.84 0 0.84 4- 0.84 0 0.56 + 0.84 0 0.28 + 0.84 0 untreated control 0 2.24 + 0.84 60.0 1.68 + - 0.84 0 1.12 + 0.84 0 0.84 4- 0.84 0 0.56 4- 0.84 16.7 0.28 4- 0.84 0 untreated control 0 2.24 + 0.84 75.0 1.68 4- 0.84 23.3 1.12 + 0.84 0 0.84 4- 0.84 10.0 0.56 + 0.84 13.3 0.28 + 0.84 0 untreated control 0 2.24 + 0.84 93.3 1.68 4- 0.84 96.7 1.12 + 0.84 90.0 0.84 4 0.84 78.3 0.56 4- 0.84 53.3 0.28 + 0.84 20.0 untreated control 0 2.24 + 0.84 100.0 1.68 4- 0.84 100.0 1.12 + 0.84 100.0 0.84 4- 0.84 100.0 0.56 + 0.84 96.7 0.28 4- 0.84 93.7 untreated control 0

P o k u s 3

In Brazil, a field trial was conducted to evaluate the herbicidal activity of the compound of Example 2, alone or in combination with either ethalfluralin or oryzalin, as well as the tolerability of the active ingredient or combinations thereof for useful plants. For both of these tests, the compound of Example 2 is made up to 50% wettable powder. For combination with the compound of Example 2, oryzalin is made into an aqueous suspension containing the active ingredient at a concentration of 480 grams per liter. In the above-mentioned test, the two compositions are mixed directly in the tank mixer and applied to the soil surface after sowing. Ethalfluralin is made into an emulsifiable concentrate containing the active ingredient at a concentration of 360 g / liter, combined with the compound of Example 2 and diluted with water to recover the tank-mix preparation. After sowing, this preparation is then incorporated into the soil by means of flexible spikes. The results of a visual comparison of the condition on the treated and untreated control boxes are recorded. Table III shows the results obtained with the combination of the compound of Example 2 and ethalfluralin, and Table IV shows the results obtained with the combination of the compound of Example 2 and oryzalin.

Table III

Efficacy of a combination of the compound of Example 2 and ethalfluralin

the observed effect number of days after treatment treatment application rate (kg / ha) efficiency rice damage 16 compound 1.5 + 0,9 0 from Example 2 1.0 + 0,9 0 + ethalfluralin 0.75 + 0,9 0 0.5 + 0,9 1.3 the compound of Example 2 1.0 0 untreated control 0 37 compound 1.5 + 0,9 0 from Example 2 1.0 ’Ί 0.9 0 -f-ethalfluralin 0.75 + 0,9 2.5 0.5 + 0,9 2.5 the compound of Example 2 1.0 0 untreated control 0 damage 16 compound 1.5 + 0,9 0 rice roots from Example 2 1.0 +: 0.9 0 -j- ethalfluralin 0.75 + 0,9 0 compound 0.5 + 0,9 ï from Example 2 1.0 0 untreated control 0 37 compound 1.5 + 0,9 0 from Example 2 1.0 + 0,9 2.5 ethalfluralin 0.75 + 0,9 0 0.5 + 0,9 0 the compound of Example 2 1.0 0 untreated control 0 extermination 37 compound 1.5 + 0,9 97.5 eleusinu from Example 2 1.0 + θ, 9 97.5 + ethalfluralin 0.75 0.9 95.0 0.5 + 0,9 95.0 the compound of Example 2 1.0 0 untreated control 0 extermination 37 compound 1.5 + 0,9 75.0 povijnice from Example 2 1.0 + θ, 9 82.5 -j- ethalfluralin 0.75 + θ, 9 77.5 0.5 + 0,9 66.3 the compound of Example 2 1.0 0 untreated control 0

ascertained effect number of treatments days after treatment applied dose efficiency (%) (kg / ha)

extermination of the purulent 37 compound 1.5 + 0,9 97.5 from Example 2 1.0 + 0,9 100.0 + ethalfluralin 0.75 + 0,9 100.0 0.5 + 0,9 100.0 compound from Example 2 1.0 100.0 untreated control 0 "Brazil 37 compound 1.5 + 0,9 90.0 Calalilly ' from Example 2 1.0 + 0,9 82.5 + ethalfluralin 0.75 + 0,9 82.5 0, 5. + 0,9 77.5 the compound of Example 2 1.0 0 untreated control 0 soya damage 17 compound 1.5 + 1.5 0 from Example 2 1.0 + 1.5 0 + oryzalin compound 0.75 + 1.5 0 from Example 2 1.0 0 untreated control 0 31 compound 1.5 7.5 from Example 2 1.0 + 1.5 0 + oryzalin 0.75 + 1.5 0 the compound of Example 2 1.0 5.0 untreated control 0 emergence of soybean 31 compound 1.5 + .1,5 82.7 from Example 2 1.0 + 1.5 75.6 + oryzalin compound 0.75 1.0 + 1.5 • 96.6 from Example 2 82.2 untreated control 100.0 damage 17 compound 1.5 + 1.5 0 soybean roots from Example 2 1.0 + 1.5 0 + oryzalin 0.75 + 1.5 0 the compound of Example 2 1.0 0 untreated control 0 31 compound 1.5 ^; + 1.5 10.0 from Example 2 1.0. -4-1.5 7.5 + oryzalin compound 0.75 + 1.5 10.0 from Example 2 1.0 5.0 untreated control 0 extermination 31 compound 1.5 + 1.5 98.2 Cenchrus echinatus from Example 2 1.0 + 1.5 95.0 + oryzalin compound 0.75 + 1.5 96.3 from Example 2 1.0 0 untreated control 0 extermination 31 compound 1.5 + 1.5 100.0 bloody blooms from Example 2 1.0 + 1.5 100.0 + oryzalin 0.75 + 1.5 100.0 the compound of Example 2 1.0 0 untreated control 0 extermination 31 compound 1.5 + 1.5 92.0 povijnice from Example 2 1.0 + 1.5 90.0 + oryzalin compound 0.75 + 1.5 85.0 from Example 2 1.0 0 untreated control 0

22 observed effect number of treatments applied dose efficacy (% j days after (kg / haj treatment)

extermination of the purulent 31 compound 1.5 + 1.5 100.0 from Example 2 1.0 + 1.5 100.0 + oryzalin 0.75 + 1.5 100.0 the compound of Example 2 1.0 98.8 untreated control 0 extermination 31 compound 1.5 + 1.5 97.5 Sida spinosa from Example 2 1.0 + 1.5 96.3 -j- oryzalin compound 0.75 + 1.5 100.0 from Example 2 1.0 0

untreated control

Claims (1)

SUBJECT A herbicidal composition comprising as active ingredient a combination of a compound of formula (I) wherein: OF THE INVENTION both R ¹ are the same and are methyl or ethyl and R ² and R ³ are the same and are fluorine, chlorine or bromine, and a second herbicide selected from the group consisting of α, α, α-trifluoro-2,6-dinitro-N, N-dipropyl-p-toluidine, N ethyl-N- (2-methyl-2-propenyl) -2,6-dinitro-4- (trifluoromethyl) benzenamine and 3,5-dinitro-4-dipropylaminophenylsulfonamide, in a weight ratio of the compound of formula I to the second herbicide of 4: 1 to 1: 3, together with one or more agriculturally acceptable carriers or diluents.