SK281061B6 - Herbicidal product, herbicidal agent containing such product and method of fighting weed growth by making use of the product - Google Patents

Abstract

A herbicidal association is as a result of the combination of 2-chloro-6-nitro-3-phenoxyaniline and at least one substituted urea of the general formula (I) wherein Ar is a phenyl-substituted R1 and R2, in which R1 is C1-3alkyl, C1-3alkoxy, Cl, Br or 5-terc-butyl-2,3-dihydro-2-oxo-1,3,4- -oxandiazol-3-yl; R2 is benzthiazol-2-yl; R3 represents H, C1-4alkyl or methoxy and R4 represents H or methyl. Also disclosed is a herbicidal product, herbicidal agent containing such product and method of fighting weed growth by making use of the product. The ratio by weight of said 2-chloro-6-nitro-3- -phenoxyaniline and said at least one substituted urea is preferably between 0.033 and 0.333.

Description

Technical field

The invention relates to a herbicidal product which is formed by combining herbicidally active substituted ureas, or mixtures thereof, with aclonifene. This product is remarkably a suitable selectively effective agent for controlling weeds in crops.

The invention also relates to the use of this novel product as a herbicide, in particular in the form of a composition, and to a method of controlling weeds in crops using the product or composition.

BACKGROUND OF THE INVENTION

Substituted ureas have long been used to degrade crop crops. Among these, the following compounds are exemplified:

- isoproturon (N, N-dimethyl-N '- (4-isopropylphenyl) urea), which is mainly used to de-grain cereal fields,

- chlortoluron (N, N-dimethyl-N '- (3-chloro-4-methylphenyl) urea, in particular for the removal of cereal fields,

- dimefuron (N, N-dimethyl-N '- [3-chloro-4- (5-tert-butyl-2-oxo-2,3-dihydro-1,3,4-oxadiazol-3-yl) phenyl] urea) to remove fields with peas or rape,

- neburon (N-methyl-N-n-butyl-N '- (3,4-dichlorophenyl) urea, in particular for the removal of cereal fields,

- linuron (N-methyl-N-methoxy-N '- (3,4-dichlorophenyl) urea), in particular for the removal of corn and sunflower fields,

- metabenzothiazuron (1-benzothiazol-2-yl-1,3-dimethylurea), in particular for the removal of cereal, bean and pea fields.

In addition, aclonifene (2-chloro-6-nitro-3-phenoxyaniline) is known to be a selective herbicide in sunflower and pea cultures, and is usually used at a dose greater than 2 kg / h.

European patent application EP 163 598 describes formulations comprising at least one herbicidally active substituted urea and optionally another herbicide. Aclonifene is also cited in a very large list of possible herbicidally active compounds.

European patent application EP 185 231 discloses a product consisting of a combination of linuron and aclonifene on page 17, the two active ingredients being combined in an aclonifene / linuron ratio of 0.4.

European patent application EP 7 482 describes an optional combination of aclonifene with another known herbicide, citing linuron.

At present, it is still desirable to improve the effect of herbicidally active compounds.

SUMMARY OF THE INVENTION

The invention relates to a novel combination of herbicidally active substances which represents a limited choice of essentially infinite number of possibilities. This combination is characterized by great advantages, which are more apparent from the following description.

A new combination of two active substances has now been found which has a remarkably and unexpectedly improved effect compared to the isolated effect of the active substances which make up this combination in controlling a number of weeds which are particularly harmful in crops. This combination retains crop selectivity. It can achieve an improvement in the spectrum of efficacy and the possibility to reduce specific doses of each active substance. The latter is particularly important for environmental reasons and does not need to be further discussed.

Thus, the combination of the invention is characterized by a remarkable degree of synergism as defined in P. M. L. Tammes, Netherlans Joumal of Plant Pathology 70, p. 7,380 (1964) in an article entitled "Isobole, and the Representation of Synergy Dans Les Pesticides" (Isoboly, a graphical representation of synergism in pesticides), or by L. E. Limpel, P.H. Schuldt and D Lamont, Proc. NEWCC 16, 48-53 (1962), t. j. (using Colby) where

E represents the expected growth inhibition in% using a mixture of two herbicides at defined doses,

X represents the observed growth inhibition in% using herbicide A at a defined dose,

Y represents the observed growth inhibition in% using herbicide B at a defined dose.

If the percent inhibition observed with the combination is greater than E, synergism occurs.

In addition, it has unexpectedly been found that when aclonifene is used in a dose that cannot be industrially described as a herbicidal dose (i.e., a dose at which efficacy is zero or inadequate), the herbicidal effect of the substituted ureas is substantially increased or extended. Therefore, this case represents an interesting innovation regarding the application of these ureas.

The invention relates to a product which is a combination

(a) aclonifene p

(b) one or more substituted ureas of formula (I) (I), wherein

Ar is a ring of formula

where

R ¹ is C 1 -C 3 alkyl, C 1 -C 3 alkoxy, chlorine, bromine, 5-tert-butyl-2,3-dihydro-2-oxo-1,3,4-oxadiazole- A 3-yl group of formula (CH ₃ ) ₃ C yy y. N --- N

R ² is H, Cl, hereinafter Ar is a ring of formula

R ³ is H, alkyl of 1 to 4 carbon atoms or methoxy,

R ⁴ represents a hydrogen atom or a methyl group, the weight ratio of component a) / component b) being between 0.033 and 0.333.

When alkyl or alkoxy groups contain at least 3 carbon atoms, they may be linear or branched.

Among the substituted ureas of formula (I), mention may be made in particular of: isoproturon (3- (4-isopropylphenyl) -1,1-dimethylurea), chlortoluron (3- (3-chloro-p-tolyl) -1,1- dimethylurea), neburon (1-butyl-3- (3,4-dichlorophenyl) -1-methylurea), diuron (3- (3,4-dichlorophenyl) -1,1-dimethylurea), methoxuron (3- (3 -chloro-4-methoxyphenyl) -1,1-dimethylurea), linuron (3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea), monolinuron (3- (4-chlorophenyl) -1-methoxy- 1-methylurea), methabenzthiazuron (1-benzothiazol-2-yl-1,3-dimethylurea), metobromuron (3- (4-bromophenyl) -1-methoxy-1-methylurea and dimethyluron (3- [4- (5-tert-butyl)) butyl-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl) -3-chlorophenyl] -1,1-dimethylurea.

In particular, isoproturon (3- (4-isopropylphenyl) -1,1-dimethylurea) chlortoluron (3- (3-chloro-p-tolyl) -1,1-) is used in view of the problems which can be solved according to the invention. dimethyl urea and methabenzthiazorone (1-benzothiazol-2-yl-1,3-dimethylurea), in particular for the removal of cereals, beans and peas.

These products may be used as herbicides in the aclonifene / urea ratio indicated, which depends in part on the type of crop to be treated, the climatic conditions, the nature of the soil, the degree of development of the main weeds at the time of treatment and, where appropriate, the user's requirements. whether the user desires complete cleaning of the treated area from weeds, or is sufficient but effective elimination of weeds.

The products according to the invention are suitable for herbicidal use, in particular for simultaneous or separate treatment or, over time, for a checkerboard-alternating treatment against undesirable plants, in particular weeds, which accompany crops. The type of crops under consideration may vary depending on the particular urea used. This aspect will be discussed further in the following description of the treatment methods.

In the case of simultaneous preferred treatment, ready-to-use products containing a combination of said active ingredients may be used. It is also possible to use products which are prepared only before the actual application by mixing the said active ingredients together at a suitable time.

The user may also use the products according to the invention by treating the crops successively first with one and then the second active ingredient, i.e. the active ingredient. j. aclonifen and ureas to produce the product of the invention "in situ" directly on the plant.

In particular, combinations of binary type are used, but sometimes thematic and quaternary combinations with one or more compatible pesticides (including fungicides or insecticides) are also contemplated.

As already mentioned, one of the problems that the present invention solves is the extension of the urea effect. In this case, aclonifen has the role of a potentiator or, if the terminology used in the field of crop protection is used, a "synergist".

The product of the invention is thus defined as a urea-based herbicidal product which contains aclonifene as a potentiator. At the same time, aclonifene has no herbicidal effect at the dose used.

Preferred alternatives with respect to the ureas used according to the invention naturally also apply to this embodiment. Even when aclonifene is used as a potentiator, the preferred ureas are chlortoluron and isoproturon.

The products of the invention are generally used in the form of herbicidal compositions which contain one or more agriculturally acceptable carriers and / or one or more surfactants.

In the case of formulations manufactured at the site of application, each of the active ingredients may be in the form of a formulation. On the other hand, in the case of ready-to-use mixtures, only the active ingredient combination is formulated.

In the following description, the term active agent and active agent combination are used without distinction.

Sometimes formulations of a suitable composition that are suitable for practicing the invention can be obtained directly on the market, other times it is necessary to prepare suitable formulations, but this is within the skill of the ordinary artisan.

In the following general description, the term 'formulation' is used in a non-discriminatory manner both to designate two formulations containing two active substances separately and to designate a formulation containing a combination thereof.

Applicable compositions may contain, in addition to the active ingredient or a combination thereof described herein, solid or liquid carriers and surfactants which must be agriculturally acceptable. Specific substances which can be used for this purpose are the usual inert carriers and the usual surfactants.

These compositions usually contain 0.5 to 95% of the active ingredient or a combination thereof according to the invention. Unless otherwise indicated, percentages are by weight.

The term "carrier" is used in this specification to refer to organic or inorganic substances of natural or synthetic origin with which the active substances can be combined to facilitate application to plants, seeds or soil. The carrier must therefore generally be inert and suitable from an agricultural point of view, in particular with regard to the plants to be treated. The carrier can be solid (clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, etc.) or liquid (water, alcohols, ketones, petroleum fractions, aromatic or paraffinic hydrocarbons, chlorinated hydrocarbons, liquefied gases and the like. ).

The surfactant may be an emulsifier, dispersant, or ionic type wetting agent. Examples are polyacrylic acid salts, lignosulfonic acid salts, phenolsulfonic acid salts or naphthalenesulfonic acid salts, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines, substituted phenols (especially alkylphenols or arylphenols), salts of sulfonate succinic acid salts alkyltaurides), esters of phosphoric acid with alcohols or polycondensates of ethylene oxide with phenols. The presence of at least one surfactant is of crucial importance since the active compounds (aclonifene and urea) are not water soluble and water is used as the delivery vehicle.

Examples of the various types of agricultural compositions which can be used are powders for use as dusts or for the production of dispersions (containing up to 100% of active compound combinations according to the invention) or granules obtained, in particular, by extrusion, compression or impregnation of a granular carrier or granulation of powders. . The content of the active compound combination according to the invention in these granules can be 1 to 80%.

The various types of liquid compositions or compositions from which the liquid compositions are made include emulsifiable concentrates, emulsions, suspensions, aerosols, wettable powders (or spray powders) and pastes.

Emulsifiable concentrates or soluble concentrates generally contain from 10 to 80% of the active ingredients, emulsions usually contain from 0.01 to 20% of the active ingredients. Suspensions usually contain 10 to 75% of active ingredient, 0.5 to 15% of surfactants, 0.1 to 10% of thixotropic agents and 0 to 10% of suitable additives such as antifoams, corrosion inhibitors, stabilizers and penetration agents.

In addition, these compositions can usually contain various other ingredients, such as thixotropic colloids, penetrating agents, stabilizers, sequestering agents, and the like, as well as other active substances known to have pesticidal properties (especially insecticides and fungicides). or plant growth-accelerating properties (in particular fertilizers) or plant growth-regulating properties. In general, the compounds of the invention can be combined with all solid or liquid additives normally used in the art.

For example, in addition to the solvent, the emulsifiable concentrates may optionally contain 2 to 20% of suitable additives such as stabilizers, surfactants, penetration agents, corrosion inhibitors, colorants or adhesion promoters.

With respect to particular active substances, the following may be considered in the practice of the invention: aclonifene, which is commercially available as a suspension containing 600 g / l of active ingredient, isoproturon, which is also commercially available as a suspension (containing 440-500 g / l) Chlortoluron, which can be obtained in the form of a suspension (containing 500-510 g of active ingredient), a wettable powder, a granulate or a microgranulate.

Those skilled in the art will readily be able to formulate a combination based on these active ingredients, for example as a suspension. This embodiment of the invention is preferred.

The invention also relates to a method for controlling weeds, particularly in an environment where crops are growing or where crops are to be grown. This inhibition is accomplished by applying an effective dose of the product or composition containing the product to the weeds.

When applied, the amount used should be sufficient to suppress weed growth without substantially sustaining crop damage. As used herein, effective dose means a dose that makes it possible to achieve this result.

Application to crops is carried out post-emergence. By post-emergence application is meant that the product is applied to the plants up to. then when they come out of the soil.

The product or composition of the invention is particularly effective against weeds, although it also has a pre-emergence effect, i. j. has an effect on plants that have not yet come out of the soil.

The effect of the product (or composition) according to the invention is effected by means of leaves and roots in a proportion which can vary depending on the particular active ingredients used.

The product (which can be applied simultaneously or separately or over time by a checkered treatment) can be used at a rate ranging from 460 to 5000 g / ha.

Among the weeds that can be suppressed with the product (or composition of the invention), mention may be made of the common ragwort (Galium aparine), the deaf oat (Avena Fatua), the buttermilk (Lolium multiflorum), the violet (Viola tricolor), white mustard (Sinapis). alba), Purple Deadnettle (Lamium purpurea), Veronica persica, Agrostis tenuis, Alopecurus myosuroides. Veronica hederifolia.

The following is a description of particularly preferred embodiments of the invention:

The isoproturon / aclonifen combination is particularly suitable for the treatment of cereals, in particular wheat and barley. The preferred dosage per hectare will be up to 600 g / ha aclonifene a

400 to 3600 g / ha of isoproturon, preferably thereafter

100 to 500 g / ha aclonifene a

500 to 3000 g / ha of isoproturon.

The chlortoluron / aclonifen combination is particularly suitable for the treatment of cereals, especially barley and wheat. The preferred dosage per hectare will be up to 600 g / ha aclonifene a

400 to 3600 g / ha of chlortoluron, preferably thereafter

100 to 500 g / ha aclonifene a

500-3000 g / ha chlortoluron.

The dimefuron / aclonifen combination is particularly suitable for the treatment of cereals such as peas and rape. The preferred dosage per hectare will be up to 600 g / ha aclonifene a

400 to 3600 g / ha of dimefuron, preferably thereafter

100 to 500 g / ha aclonifene a

500 to 2000 g / ha of dimefuron.

The aclonifen / methabenzthiazuron combination is particularly suitable for the treatment of winter wheat and winter barley. The preferred dosage per hectare will be

600 to 1000 g / ha aclonifene a

500 to 4000 g / ha of isoproturon, preferably thereafter

100 to 500 g / ha aclonifene a

1000 to 3000 g / ha of methabenzthiazuron.

The invention is described by way of example. These examples are illustrative only and do not limit the scope of the invention in any way.

To simplify the method and to provide a better basis for comparing the results, the efficacy of the products of the invention is tested against the following weeds.

Gallium aparine,

Avena futua (deaf oats),

Lolium multiflorum,

Viola tricolor,

Sinapis alba (White Mustard),

Lamium purpurea (Purple Deadnettle),

Veronica persica,

Agrostis tenuis,

Alopecurus myosuroides,

Stellaria media.

Weed plants are grown in wheat to demonstrate the selectivity of the products of the invention to this crop.

General Experimental Procedure:

Application to plants is carried out post-emergence.

A certain number of seeds, determined by plant type, are sown in 9x9x9 cm pots filled with light agricultural land. The seeds are covered with a layer of soil about 3 mm thick and germinated. The treatment is carried out only after the seedlings have grown to a suitable stage. In the case of grass weeds, treatment is carried out at a time when the plant reaches the second leaf stage. In the case of dicotyledonous plants, the treatment is carried out at the stage where the cotyledon is opened and the first leaf has been developed.

The pots are then sprayed with a mixture corresponding to an application rate of 500 l / ha containing test substances. The mixtures are prepared by diluting the appropriate agents with water. The following means shall be used:

- aclonifene suspension containing 600 g / l, 'Challenge 600 *',

- isoproturon suspension containing 500 g / l, "Augur®",

- a chlorotoluron suspension containing 500 g / l, 'Dicuran®',

a dimefuron suspension containing 400 g / l of Surdone®.

These compositions are duly approved and known in the art.

The pots are placed in containers adapted to supply irrigation water from below and maintained at ambient temperature and 60% relative humidity for 24 days.

After 24 days, the number of live plants in pots treated with a mixture containing the test active substances and the number of live plants in a control pot that were treated under the same conditions were determined, but using a mixture that did not contain the active compound. In this way, the percentage of treated plants destroyed in percentage, relative to the untreated sample, was determined. A 100% suppression means that this type of plant has been completely destroyed and a 0% suppression means that the number of live plants in the treated pot is the same as the number of live plants in the control pot.

In the tables of Examples 1 to 16, the amount of aclonifene is shown in the first column and the amount of substituted urea in the first row. Both quantities are expressed in grams of active ingredient per hectare.

DETAILED DESCRIPTION OF THE INVENTION

Example 1

This experiment demonstrates the nature of the synergistic biological effect of the combination of isoproturon and aclonifen on Lolium multiflorum.

The experiment is carried out using the pre-sown seeds of the Buttercup.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value represents the value actually achieved and the lower value the value expected from the Colby formula calculations.

aclonifen

isoproturon

0 500 1000 2000 0 0 30 65 50 62 0 60 30 90 65 85 50 125 0 65 30 90 65 95 50 250 0 90 65 98 50

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 2

This experiment demonstrates the nature of the synergistic biological effect of the combination of isoproturon and aclonifen on Alopeeurus myosuroides.

The experiment is performed using pre-sown seeds of Alopecurus myosuroides.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value represents the value actually achieved and the lower value the value expected from the Colby formula calculations.

isoproturon

0 500 1000 2000 0 0 20 50 85 62 0 30 20 75 50 - 125 0 55 20 65 50 83 85 250 0 85 50 93 85

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 3

This experiment demonstrates the nature of the synergistic biological effect of the combination of isoproturon and aclonifen on Agypstis tenuis. . _T

The experiment is performed using pre-sown Agrostis tenuis seeds.

The following table shows the average values measured in the greenhouse experiment. At each level give)? higher value represents the value actually achieved. * required and lower value the value expected from the Colby calculations.

isoproturon

aclonifen

0 50 0 1 000 2 000 0 0 30 90 95 62 0 90 30 100 90 100 95 125 0 95 30 100 90 100 95 250 0 100 90 100 95

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 4

This experiment demonstrates the nature of the synergistic biological effect of the combination of isoproturon and aclonifen on Lamium purpurea.

The experiment is carried out using pre-sown Lamium purpurea seeds.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value is the value actually achieved and the lower value is the value expected based on the Colby formula calculations.

aclonifen

isoproturon

0 500 1000 2000 0 0 0 15 20 62 0 20 0 20 15 25 20 125 20 40 20 30 30 40 36 250 20 50 32 75 36

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 5

This experiment demonstrates the nature of the synergistic biological effect of the combination of isoproturon and aclonifen on Viola tricolor.

The experiment is performed using pre-sown Viola tricolor seeds.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value represents the value actually achieved and the lower value the value expected from the Colby formula calculations.

isoproturon

aclonifen

0 500 1000 2000 0 0 0 15 20 62 0 15 0 25 15 25 20 125 0 25 0 25 15 30 20 250 15 30 28 40 32

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 6

This experiment shows that the combination of isoproturon and aclonifene does not show any phytotoxicity to common wheat (Triticum aestivum).

The procedure is as described in the preceding examples except that the seeds of wheat are sown in advance. The results shown in the following table are achieved.

isoproturon

aclonifen

0 500 1000 2000 0 0 0 0 0 62 0 0 0 0 125 0 0 0 0 250 0 0 0

Based on these results, it can be concluded that, although characterized by the increased activity of the active compounds against weed plants used in this example, it does not show any phytotoxicity to wheat.

Example 7

This experiment demonstrates the nature of the synergistic biological effect of the combination of chlortoluron and aclonifen on Alopeeurus myosuroides.

The experiment is performed using pre-sown seeds of Alopecurus myosuroides.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value represents the value actually achieved and the lower value the value expected from the Colby formula calculations.

aclonifen

chlorotoluron

0 500 1000 1500 0 0 65 70 80 62 0 60 65 97 70 97 80 125 10 70 68 85 73 99 82 250 20 98 76 100 84

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 8

This experiment demonstrates the nature of the synergistic biological effect of the combination of chlortoluron and aclonifen on deaf oats (Avena fatud).

The experiment is performed using pre-sown deaf oat seeds.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value represents the value actually achieved and the lower value the value expected from the Colby formula calculations.

aclonifen

chlorotoluron

0 500 1000 1500 0 0 10 55 93 62 0 35 10 75 55 88 93 125 0 35 10 70 55 88 93 250 0 88 55 90 93

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 9

This experiment demonstrates the nature of the synergistic biological effect of the combination of chlortoluron and aclonifen on Lolium multiflorum.

The experiment is carried out using the pre-sown seeds of Buttercup.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value represents the value actually achieved and the lower value the value expected from the Colby formula calculations.

aclonifen

chlorotoluron

0 500 1000 1500 0 0 78 93 62 0 100 78 100 93 125 5 98 79 100 93 250 10 100 94

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

and the lower value is the value expected from Colby's calculations.

chlorotoluron

aclonifen

0 500 1000 1500 0 0 15 25 45 62 0 30 15 40 25 65 45 125 0 45 15 70 25 80 45 250 15 70 36 70 53

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 12

This experiment shows that the combination of chlortoluron and aclonifen does not show any phytotoxicity to common wheat (Triticum aestivum).

The procedure is as described in the preceding examples except that the seeds of wheat are sown in advance. The results shown in the following table shall be achieved:

isoproturon

Example 10

This experiment demonstrates the nature of the synergistic biological effect of the combination of chlortoluron and aclonifen on Viola tricolor.

The experiment is performed using pre-sown Viola tricolor seeds.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value represents the value actually achieved and the lower value the value expected from the Colby formula calculations.

chlorotoluron

0 500 1000 1500 0 0 0 15 25 62 0 20 0 35 15 60 25 125 0 30 0 60 15 65 25 250 5 70 19 85 29

aclonifen

0 500 1000 1500 0 0 0 0 0 62 0 0 0 0 125 0 5 0 0 250 0 0 0

On the basis of these results, it can be concluded that, although characterized by the increased activity of the active compounds against weed plants used in this example, it does not show any phytotoxicity to wheat.

Example 13

This experiment demonstrates the nature of the synergistic biological effect of the combination of dimefuron and aclonifen on Sinapis alba.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value represents the value actually achieved and the lower value the value expected from the Colby formula calculations.

dimefuron

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 11

This experiment demonstrates the nature of the synergistic biological effect of a combination of chlortoluron and aclonifen on Galatine aparine.

The experiment is carried out using pre-seeded Gaium aparine seeds

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value is actually achieved by Aconifen

0 500 1000 2000 0 0 10 45 70 62 0 35 10 93 45 100 70 125 20 80 28 98 56 100 76 250 30 100 61 100 79

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

SK 281061 Β6

Example 14

This experiment demonstrates the nature of the synergistic biological effect of the combination of dimefuron and aclonifen on Viola tricolor.

The experiment is performed using pre-sown Viola tricolor seeds.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value represents the value actually achieved and the lower value the value expected from the Colby formula calculations.

dimefuron

aclonifen

0 500 1000 2000 0 0 25 45 85 62 0 25 35 50 45 95 85 125 0 30 25 70 45 95 85 250 10 83 50 100 86

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 15

This experiment demonstrates the nature of the synergistic biological effect of the combination of dimefuron and aclonifen on Lolium multiflorum.

The experiment is performed using pre-sown Lolium multiflorum seeds.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value represents the value actually achieved and the lower value the value expected from the Colby formula calculations.

dimefuron

aclonifen

0 500 1000 2000 0 0 10 25 60 62 0 15 10 35 25 80 60 125 0 20 10 55 25 65 60 250 5 55 29 65 62

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 16

This experiment demonstrates the nature of the synergistic biological effect of the combination of dimefuron and aclonifen on Veronica persica.

The experiment is performed using pre-sown seeds of Veronica persica.

The following table shows the average values measured in the greenhouse experiment. At each dosage level, the higher value represents the value actually achieved and the lower value the value expected from the Colby formula calculations.

aclonifen

dimefuron

0 500 1000 2000 0 0 55 97 100 62 0 68 55 80 97 100 100 125 5 100 57 100 97 100 100 250 5 94 97 100 100

The results shown in the above table clearly show (with respect to the formula quoted in the introductory part of this description) what excellent and unexpected degree of synergism is achieved using the combination of the invention.

Example 17

This experiment demonstrates the nature of the synergistic biological effect of the combination of aclonifene and methabenzthiazuron.

This experiment is carried out on 2 x 5 m test fields in the form of strips. The fields are sown in strips with two crops and a group of weeds, each experiment being repeated three times. Other weeds are present from natural infestation.

The treatment is carried out at a time when the crops and weeds reach the stage at which at least one complete shoot is developed, the monocotyledonous plants comprising three shoots and the dicotyledonous plants are in the development stage from the cotyledon stage to the small plant stage.

The fields shall be sprayed with a test sprayer mounted on the tractor at a rate of 195 l / ha. Aclonifene is used as a suspension containing 600 g / l (Challenge 600®), methabenzthiazuron as a liquid containing 700 g / l (Tribunyl *). The compositions are applied separately as a mixture.

After 60 days, the percentage of weeds present in comparison with the untreated control field (0 = no effect, 100 = complete destruction) was determined. The tests use Galium aparine and Avena fatua and winter wheat and winter barley.

The following table shows the average results obtained for three replicates of each experiment. The results are shown for each dose level observed compared to the result expected using the Colby formula.

Suppression 'V Suppression

Galiu · aparine Avena ŕatua active ingredient (j / ha) found expected found expected

250 Jj aclonifene

5C0 45

Override i% i

Galiu · aparina

3J

4S

The inhibition (s) of the substance (s) / (s) on the expected expected found aclonifene and the like. 3Ί M 91 aclonifene

94

SK 281061 Β6

The table below clearly demonstrates the synergistic behavior of the combination.

Claims (18)

PATENT CLAIMS A herbicidal product consisting of a synergistic combination of 2-chloro-6-nitro-3-phenoxyaniline and one or more substituted ureas of formula (I) (I) wherein Ar is a group of formula wherein R ¹ is an alkyl group containing 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a chlorine atom, a bromine atom or a 5-tert-butyl-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl group of the formula (CH) ₃ ) ₃ Y N - and R ² represents a hydrogen atom or a chlorine atom, or Ar further represents a group of the formula R ³ is H, alkyl of 1 to 4 carbon atoms or methoxy and R ⁴ is H or methyl, characterized in that it contains 2-chloro-6-nitro-3-phenoxyaniline, and substituted urea in a weight ratio of 0.033 to 0.333. A herbicidal product according to claim 1, characterized in that it contains, as a substituted urea of formula (I), a compound selected from the group consisting of: 3- (4-isopropylphenyl) -1,1-dimethylurea, 3- (3-chloro-p-tolyl) -1,1-dimethylurea, 1-butyl-3- (3,4-dichlorophenyl) -1-methylurea, 3- (3,4-dichlorophenyl) -1,1-dimethylurea, 3- (3-chloro-4-methoxyphenyl) -1,1-dimethylurea, 3- (3,4-dichlorophenyl) -1-methoxy-1 -methylurea, 3- (4-chlorophenyl) -1-methoxy-1-methylurea, 1-Benzothiazol-2-yl-1,3-dimethylurea 3- (4-bromophenyl) -1-methoxy-1-methylurea and N, N-dimethyl-N '- [3-chloro-4- (5-tert- butyl-2-oxo-2,3-dihydro-1,3,4-oxadiazol-3-yl) phenyl] urea. The herbicidal product according to claim 2, characterized in that it contains 3- (4-isopropylphenyl) -1,1-dimethylurea or 3- (3-chloro-p-tolyl) -1,1-dimethylurea as substituted urea. A herbicidal product according to claim 1, characterized in that it is adapted for simultaneous, separate or spaced use for controlling undesirable plants or weeds in crops. A herbicidal product according to claim 1, characterized in that it contains 2-chloro-6-nitro-3-phenoxyaniline in a herbicidally ineffective amount which potentiates the potency of urea in the herbicidal product. A herbicidal composition, characterized in that it comprises a herbicidal product according to any one of claims 1 to 5, at least one inert carrier and / or at least one surfactant. The herbicidal composition according to claim 6, characterized in that it contains 0.5 to 95% of the herbicidal product according to any one of claims 1 to 5. A method for controlling weed growth after emergence of crop plants, characterized in that the crop is applied to the site an effective dose of the herbicidal product according to any one of claims 1 to 5. The method according to claim 8, characterized in that weed growth is suppressed from the group comprising Gaium aparine, Avena fatua, Lolium multiflorum, Viola tricolor, Sinapis alba, Lamium purpurea, Veronica persica, Agrostis tenuis and Alopecurus myosuroides. Process according to claim 8, characterized in that the herbicidal product is applied in an amount of 460 to 5000 g / ha. Process according to claim 8, characterized in that a combination of 400 to 3600 g / ha of 3- (4-isopropylphenyl) -1,1-dimethylurea and 60 to 600 g / ha of 2-chloro-6-nitro-3 is applied. -phenoxyaniline and that the useful plants are cereals. Method according to claim 11, characterized in that a combination of 100 to 500 g / ha is applied 2-chloro-6-nitro-3-phenoxyaniline and 500-3000 g / ha of 3- (4-isopropylphenyl) -1,1-dimethylurea. Method according to claim 8, characterized in that a combination of 400 to 3600 g / ha is applied 3- (3-chloro-p-tolyl) -1,1-dimethylurea and 60-600 g / ha of 2-chloro-6-nitro-3-phenoxyaniline and that the useful plants are cereals. Method according to claim 13, characterized in that a combination of 100 to 500 g / ha of 2-chloro-6-nitro-3-phenoxyaniline and 500 to 3000 g / ha of 3- (3-chloro-p-tolyl) is applied. -l, l-dimethylurea. Ϊ " The method of claim 8, wherein a combination of 400 to 3600 g / ha of N, N-dimethyl-N '- [3-chloro-4- (5-tert-butyl-2-oxo-2) is applied. 3-dihydro-1,3,4-oxadiazol-3-yl) phenyl] urea and 60 to 600 g / ha 2-chloro-6-nitro-3-phenoxyaniline and that the useful plants are oilseed rape and peas. Method according to claim 15, characterized in that a combination of 100 to 500 g / ha is applied 3-chloro-6-nitro-3-phenoxyaniline and 500 to 2000 g / ha of N, N-dimethyl-N '- [3-chloro-4- (5-tert-butyl-2-oxo-2,3-dihydro) -1,3,4-oxadiazol-3-yl) phenyl] urea. The method according to claims 8-10, characterized in that a combination of 60 to 1000 g / ha of 2-chloro-6-nitro-3-phenoxyaniline and 500 to 4000 g / ha of 1-benzothiazol-2-yl-1,3 is applied. -dimets of urea. Process according to claim 17, characterized in that a combination of 100 to 500 g / ha of 2-chloro-6-nitro-3-phenoxyaniline and 1000 to 3000 g / ha of 1-benzothiazol-2-yl-1,3 is applied. dimethylurea.