FR2768902A1 - NOVEL FUNGICIDE COMPOSITION - Google Patents

Abstract

The invention concerns a fungicide composition comprising a compound A which is 2-(2,4- dichlorophenyl)-3- (1H-1,2,4, -triazol-1-yl)propyl-1, 1,2,2-tetrafluorethylether in racemic form or not, and a compound B which is (E)-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3- methyl methoxyacrylate. The invention also concerns a curative or preventive method for fighting against phytopathogenic fungi using such a composition.

Description

New fungicidal composition
The subject of the present invention is a novel fungicidal composition and a process using said composition and intended to protect, as a curative or preventive action, the cultures against fungal attacks.

 EP 234242 discloses 2-phenylpropyl triazole derivatives having anti-fungal properties.

 Patent EP 382375 describes ortho-phenylmethoxyacrylates also having fungicidal properties on cereals, vines, rice, etc. This patent also describes the possibility of associating these methoxyacrylates with triazole derivatives, without, however, clearly indicating the advantage obtained with such associations.

 Although possessing good fungicidal activities, the compounds described in these patents do not exhibit a sufficiently broad spectrum of fungicidal activity for the preventive or curative treatment of diseases affecting the cultures.

 An object of the present invention is to provide novel fungicidal compositions filling these gaps.

 Indeed, it is still desirable to improve the spectrum of activity and the effectiveness of such fungicidal compounds, or to strengthen them by combining them with other molecules to obtain a more effective product or to prevent the appearance of fungal strains resistant to these new fungicides.

 It is also very desirable to have fungicidal products having an improved persistence of action, such as to space out in time the number of phytosanitary treatments necessary for good pest control.

 In any case, it is particularly advantageous to be able to reduce the quantity of chemicals spread in the environment, while providing effective crop protection against fungal attack.

 It has now been found that one or more of the foregoing objectives could be achieved by the fungicidal composition of the present invention.

The subject of the present invention is therefore a fungicidal composition comprising:
a compound A which is 2- (2,4-dichlorophenyl) -3- (1H-1,2,4, -triazol-1-
yl) propyl-1,1,2,2-tetrafluoroethyl ether, in racemic or non-racemic form,
described in EP 234242, and
a compound B which is (E) - {2- [6- (2-cyanophenoxy) pyrimidin-4-
methyl yloxy] phenyl-3-methoxyacrylate, described in EP 382375.

The structures corresponding to the names of the active ingredients A and B are indicated in "The pesticide manual" published by Clive TOMLIN and published by the
British Crop Protection Council, 10th edition (compound No. 667, page 965 for compound A and compound No. 394, page 579 for compound B).

 The fungicidal composition according to the invention advantageously comprises the components A and B in a ratio by weight A / B of between 1/12 and 12/1, preferably between 1/4 and 4/1, and even more advantageously in a ratio between 1/2 and 1/1.

 Due to the presence of an asymmetric carbon in the compound A, it can be used in its racemic form or in the form of one or other of its optical isomers or in the form of a mixture of its two isomers. In the latter case, the enantiometric ratio between the two isomers is between 50% (racemic) and 100% (pure enantiomer). In the present invention, the term compound A therefore includes the racemic compound A, its R isomer or S isomer, as well as any mixture of these two isomers in any proportion.

In the following of the present invention, it is understood that
- unless otherwise indicated the term "compound A" refers to racemic; and,
when compound A is not used in its racemic form (that is to say isomer pure or in mixture), the amount of compound A may advantageously be between 40% and 99.9% relative to that of racemic more preferably between 50% and 85%.

 When compound A is not used in its racemic form, it will preferably be used a mixture of R and S isomers in which the R isomer is predominant. More preferably still, the pure R isomer will be used.

 Unexpectedly, the Applicant has discovered that the composition according to the invention then significantly improves the action of active ingredients taken separately for a number of fungi particularly harmful to crops, especially cereals.

This improvement is reflected in particular:
by a higher fungicidal activity of the mixture of compounds A and B relative to compounds A and B taken separately;
by reducing the doses of each of the constituents, which is particularly advantageous for the user and the environment, and
- by a significant increase in crop yields.

 The fungicidal composition according to the invention comprises, as active ingredient, compound A and compound B in admixture with agriculturally acceptable solid or liquid carriers and / or surfactants also acceptable in agriculture. In particular, the inert and conventional supports and the usual surfactants can be used. These compositions cover not only the compositions ready to be applied to the crop to be treated by means of a suitable device, such as a spraying device, but also the commercial concentrated compositions which must be diluted before application to the crop.

 These compositions may also contain all kinds of other ingredients such as, for example, protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilizers, sequestering agents, etc. More generally the compounds A and B can be combined with any solid or liquid additives corresponding to the usual techniques of formulation.

 In general, the compositions according to the invention usually contain from 0.05 to 95% (by weight) of active ingredient (mixture A + B), one or more solid or liquid carriers and, optionally, one or more agents. surfactants.

 By the term "carrier", in the present description, is meant an organic or inorganic material, natural or synthetic, with which the active ingredient is combined to facilitate its application to the aerial parts of the plant. This support is therefore generally inert and must be acceptable in agriculture, especially on the treated plant. The support may be solid (clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, etc.) or liquid (water, alcohols, especially butanol, etc.).

 The surfactant may be an emulsifier, dispersant or wetting agent of ionic or nonionic type or a mixture of such surfactants. There may be mentioned, for example, salts of polyacrylic acids, salts of lignosulfonic acids, salts of phenolsulphonic or naphthalenesulphonic acids, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines. substituted phenols (especially alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (especially alkyltaurates), phosphoric esters of polyoxyethylated alcohols or phenols, acid esters and polyols, sulfates, sulfonates and phosphates-based derivatives of the foregoing compounds. The presence of at least one surfactant is generally indispensable when the active ingredient and / or the inert carrier are not soluble in water and the application carrier agent is water.

 Thus, the compositions for agricultural use according to the invention may contain the active ingredient within very wide limits, ranging from 0.05% to 95% by weight. Their content of surfactant is advantageously between 5% and 40% by weight. Unless otherwise indicated, the percentages given in this specification and in the claims are percentages by weight.

 These compositions according to the invention are themselves in quite diverse forms, solid or liquid.

 As forms of solid compositions, mention may be made of dusting powders (with an active matter content of up to 100%) and granules, in particular those obtained by extrusion, by compacting, by impregnation of a granulated support, by granulation from a powder (the content of active material in these granules being between 0.5 and 90% for the latter cases), tablets or effervescent tablets.

 The fungicidal composition according to the invention can also be used in the form of a powder for dusting; a composition comprising 50 g of active material and 950 g of talc can also be used; a composition comprising 20 g of active material, 10 g of finely divided silica and 970 g of talc can also be used; these constituents are mixed and milled and the mixture is applied by dusting.

 As forms of compositions that are liquid or intended to constitute liquid compositions during application, mention may be made of solutions, in particular concentrates that are soluble in water, emulsions, concentrated suspensions, aerosols, wettable powders (or powder to spray), pasta, gels.

 The concentrated suspensions, which are applicable as sprays, are prepared in such a way as to obtain a stable fluid product which does not deposit and usually contain from 10 to 95% of active substance, from 0.5 to 15% of surfactants, from 0 to 1 to 10 No. of thixotropic agents, from 0 to 10 Wo of suitable additives, such as antifoams, corrosion inhibitors, stabilizers, penetrants and adhesives and, as carrier, water or an organic liquid in which the active ingredient is little or not soluble: some organic solids or mineral salts can be dissolved in the support to help prevent sedimentation or as antifreezes for water.

By way of example, a concentrated suspension composition (SC) consists of
Example SC 1:
active ingredient 500 g
- polyethoxylated tristyrylphenol phosphate 50 g
polyethoxylated alkylphenol 50 g
- sodium polycarboxylate 20 g
- ethylene glycol 50 g
- organopolysiloxane oil (antifoam) 1 g
- polysaccharide 1.5 g
water 316.5 g
Wettable powders (or spray powder) are usually prepared to contain from 20 to 95% active ingredient, and usually contain, in addition to the solid support, from 0 to 30% of a wetting agent, at 20% of a dispersing agent, and, when necessary, from 0.1 to 10% of one or more stabilizers and / or other additives, such as penetrating agents, adhesives, or anti-caking agents, dyes, etc.

 In order to obtain the spraying powders or wettable powders, the active ingredients in the appropriate mixers are intimately mixed with the additional substances and milled with suitable mills or other mills. Spray powders are thus obtained, the wettability and suspension of which are advantageous; they can be suspended with water at any desired concentration and these suspensions can be used very advantageously especially for application to the leaves of plants.

 In place of the wettable powders, pasta can be made. The conditions and methods of production and use of these pastes are similar to those of wettable powders or powders to be sprayed.

By way of example, wettable powders (PM) compositions (or powders for spraying) consist of
Example PM 1
- active ingredient 50%
- ethoxylated fatty alcohol (wetting agent) 2.5%
- ethoxylated phenylethylphenol (dispersing agent) 5%
- chalk (inert support) 42.5%
Example PM 2:
- active ingredient 10%
- oxo synthetic alcohol of branched type, in
C13 ethoxylated with 8 to 10 ethylene oxide
(wetting agent) 0.75%
- neutral calcium lignosulfonate (agent
dispersant) 12%
- calcium carbonate (inert filler) qs 100%
Example PM 3:
This wettable powder contains the same ingredients as in the previous example, in the following proportions
- active ingredient 75%
- wetting agent 1.50%
- dispersing agent 8%
- calcium carbonate (inert filler) qs 100%
Example PM 4:
- active ingredient 90%
- ethoxylated fatty alcohol (wetting agent) 4%
- ethoxylated phenylethylphenol (dispersing agent) 6%
Example PM 5:
- active ingredient 50%
- mixture of anionic surfactants and
nonionic (wetting agent) 2.5%
- sodium lignosulfonate (dispersing agent) 5%
- kaolinic clay (inert support) 42.5%
The aqueous dispersions and emulsions, for example the compositions obtained by diluting with water a wettable powder or an emulsifiable concentrate according to the invention, are included in the general scope of the present invention. The emulsions may be of the water-in-oil or water-water type and may have a thick consistency such as that of a "mayonnaise".

 The fungicidal compositions according to the invention may be formulated in the form of water-dispersible granules also included in the scope of the invention.

 These dispersible granules, with an apparent density generally of between approximately 0.3 and 0.6, have a particle size generally of between approximately 150 and 2000 and preferably between 300 and 1500 clams.

 The active ingredient content of these granules is generally between about 1% and 95%, and preferably between 25% and 90%.

 The remainder of the granule is essentially composed of a solid filler and optionally surfactant adjuvants conferring on the granule properties of dispersibility in water. These granules can be essentially of two distinct types depending on whether the charge retained is soluble or not in water. When the filler is water soluble, it may be inorganic or, preferably, organic. Excellent results have been obtained with urea. In the case of an insoluble filler, it is preferably mineral, such as kaolin or bentonite. It is then advantageously accompanied by surfactants (in a proportion of 2 to 20% by weight of the granule) of which more than half is, for example, constituted by at least one dispersing agent, essentially anionic, such as an alkaline polynaphthalene sulphonate. or alkaline earth or an alkaline or alkaline earth lignosulfonate, the remainder being nonionic or anionic wetting agents such as an alkaline or alkaline earth alkyl naphthalene sulfonate.

 On the other hand, although not essential, other adjuvants such as antifoam agents may be added.

 The granulate according to the invention can be prepared by mixing the necessary ingredients and then granulating according to several techniques known per se (dredger, fluid bed, atomizer, extrusion, etc ...). It is generally finished by crushing followed by sieving at the particle size chosen within the limits mentioned above. It is also possible to use granules obtained as above and then impregnated with a composition containing the active ingredient.

 Preferably, it is obtained by extrusion, operating as indicated in the examples below.

Example Gui: Dispersible granules
In a mixer, 90 Wo by weight of active material and 10% of urea beads are mixed. The mixture is then milled in a pin mill.

A powder is obtained which is moistened with about 8% by weight of water. The wet powder is extruded in a perforated roll extruder. A granule is obtained which is dried, then crushed and sieved so as to keep only the granules with a size of between 150 and 2000 μm, respectively.

Example GD2: Dispersible granules
In a mixer, the following constituents are mixed
- active ingredient 75%
- wetting agent (sodium alkylnaphthalene sulphonate) 2%
- dispersing agent (sodium polynaphthalene sulphonate) 8%
- inert load insoluble in water (kaolin) 15%
This mixture is granulated in a fluid bed, in the presence of water, then dried, crushed and sieved so as to obtain granules with a size of between 0.15 and 0.80 mm.

 These granules can be used alone, in solution or dispersion in water so as to obtain the desired dose. They can also be used to prepare combinations with other active ingredients, especially fungicides, the latter being in the form of wettable powders, or aqueous granules or suspensions.

 As regards the compositions suitable for storage and transport, they more preferably contain from 0.5 to 95% (by weight) of active material.

 The invention also relates to a method for the preventive or curative treatment of the multiplication products of plants, as well as the resulting plants, against fungal diseases, characterized in that said products are coated with an effective dose and not phytotoxic composition of the invention.

The fungicidal composition that is the subject of the invention is applied by means of various treatment methods such as:
spraying the aerial parts of the cultures to be treated with a liquid comprising said composition,
- dusting, incorporation into the ground of granules or powders, watering, injection into the trees or painting.

 Spraying a liquid on the aerial parts of the cultures to be treated is the preferred method of treatment.

 Among the multiplication products of the plants concerned, mention may in particular be made of seeds or seeds, and tubers.

 The methods of recovery of plant propagating products, in particular seeds, are well known in the art and make particular use of filming or coating techniques.

 By "effective and non-phytotoxic amount" is meant a quantity of composition according to the invention which is sufficient to allow the control or destruction of fungi present or likely to appear on the cultures, and which does not cause for said cultures any noticeable symptoms of phytotoxicity.

 Such an amount is likely to vary within wide limits depending on the fungus to be fought, the type of culture, the climatic conditions, and the compounds included in the fungicidal composition according to the invention. This amount can be determined by systematic field tests, within the reach of the skilled person.

 By curative or preventive treatment, we mean a treatment carried out one or more times before or after the appearance of the first symptoms of the fungal disease that we wish to combat.

 Compounds A and B are applied simultaneously, but can also be applied sequentially or separately.

The doses of use during the implementation of the process according to the invention will then generally be on vines, cereal and vegetable crops, arboriculture, citrus fruits, etc.
- by foliar treatment
50 to 800 g / ha of compound B + 50 to 800 g / ha of compound A and more precisely 100 to 400 g / ha + 100 to 400 g / ha, ie a total dose of composition according to the invention of between 100 and 1600 g / ha, preferably between 200 and 800 g / ha. Preferably, a total dose of composition according to the invention of 325 g / ha or 125 g / ha of compound A + 200 g / ha of compound is used.
B, or a total dose of composition according to the invention equal to 300 g / ha, ie 100 g / ha of compound A + 200 g / ha of compound B.

- by ground treatment (watering)
2 to 30 kg / ha of compound B + 2 to 30 kg / ha of compound A and more precisely 2 to 15 kg / ha + 2 to 15 kg / ha, ie a total dose of composition according to the invention of between 4 and 30 kg / ha, preferably between 4 and 15 kg / ha. Preferably, a total dose of composition according to the invention is used equal to 4.2 kg / ha, ie 1.6 kg / ha of compound A + 2.6 kg / ha of compound B.

- by treatment of the products of propagation of the plants:
1 to 400 g of compound B + 1 to 400 g of compound A per 100 kg of seed and more specifically 2 to 400 g + 1 to 200 g, ie a total dose of composition according to the invention of between 2 and 800 g, preferably between 3 and 600 g of active material per 100 kg of seed.

The phytopathogenic fungi of the cultures that can be fought by this process are those generally observed for the crop types concerned and in particular:
the fungi responsible for septoria diseases, for example Septoria spp., in particular Septoria tritici and Septoria nodorum,
the fungi responsible for the oldium, for example Erysiphe graminisforma specie tritici and Erysiphe graminisforma specie horde,
- the fungi responsible for rust, for example Pteccinic strEiformi.st, Puccinia triticina, Puccinia horclel and Puccinia reconclita,
fungi responsible for diseases of the potato tuber, for example Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Fluaritol solani.

 The crops contemplated in the context of the present invention are preferably cereal crops (wheat, rye, triricale and barley in particular), vegetables (beans, onions, cucurbits, cabbage, potatoes, tomatoes, peppers, spinach, peas, lettuce). , endive), fruit crops (strawberry, raspberry), tree crops (apple, pear, ginseng, lemon, coconut, cocoa, rubber, banana), vine, sunflower, beet, tobacco and ornamentals.

 Wheat and barley are the preferred plants for carrying out the method according to the invention.

 The following examples are given purely by way of illustration of the invention, which they do not limit in any way.

 Example 1: Wheat test (Recital variety).

Wheat (Récital variety) sown seven months earlier (at a rate of 185 kg / ha, in a clay-loam soil) is subjected to foliar spray treatment (at the rate of 333.33 l / ha) of the following agrochemical compositions diluted in water:
1) Compound A (in racemic form) assayed for application to
125 g / ha;
2) Compound B assayed for application at 250 g / ha;
3) mixture A + B dosed 100 g / ha for A (in racemic form) and
200 g / ha forB;
4) mixture A + B dosed 125 g / ha for A (in racemic form) and
200 g / ha for B.

 A single application is performed for each of compositions 1 to 4.

 The disease is allowed to develop naturally, in this case Septoria Septoria tritici.

Eighteen days after these treatments, a notation is made. This one
consists in estimating the proportion of plant affected by the disease by defining a
percentage of contamination:
100% indicates total contamination of the plant by the fungus;
0% indicates no contamination.

The following results are observed

<tb><SEP> Composition <SEP>% <SEP> of <SEP> Contamination <SEP>% <SEP> of <SEP> Contamination
<tb><SEP> 18 <SEP> days <SEP> after <SEP> treatment <SEP> 28 <SEP> days <SEP> after <SEP> treatment
<tb><SEP> A <SEP> 125 <SEG> g / ha <SEP> 66 <SEP><SEP> 17
<tb><SEP> B <SEP> 250 <SEP> g / ha <SEP> 71 <SEP> 25
<tb> A <SEP> 100 <SEP> g (ha <SEP> + <SEP> 61 <SEP> 4
<tb><SEP> B <SEP> 200 <SEP> a <SEP> l <SEP>
<tb><SEP> A <SEP> 125 <SEP> g / ha <SEP> + <SEP> 58 <SEP> 3
<tb><SEP> B <SEP> 200 <SEP> g / ha <SEP>
<Tb>
Very significant results with contamination percentages of only 3-4% with the A + B mixture and 17 and 25% with
A and B respectively.

It should be noted further that the doses of A and B in the mixture represent
80% of the doses used for the compounds A and B taken separately.

 Example 2: Wheat test (Oracle variety).

Wheat (Oracle variety) sown six months earlier (at a rate of 150 kg / ha, in a loam + stones area) is subjected to foliar spray treatment (at a rate of 333 l / hua) of the following agrochemical compositions diluted in water. 'water:
1) Compound A (in racemic form) assayed for application to
125 g / ha;
2) Compound B assayed for application at 250 g / ha;
3) mixture A + B dosed 100 g / ha for A (in racemic form) and
200 g / ha forB;
4) mixture A + B dosed 125 g / ha for A (in racemic form) and
200 g / ha for B.

 A second application is made under the same conditions a month later.

 The disease is allowed to develop naturally, in this case Septoria tritici septoria, powdery mildew Erysiphe graminis and rust Puccinia triticina.

After these treatments, it is estimated the proportion of plant affected by the disease by defining a percentage of contamination:
100% indicates total contamination of the plant by the fungus;
0% indicates no contamination.

The following results are observed: a) for powdery mildew

<tb> Composition <SEP>% <SEP><SEP> of <SEP> contamination <SEP>% <SEP> of <SEP> contamination
<tb><SEP> 14 <SEP> days <SEP> after <SEP> treatment <SEP> 28 <SEP> days <SEP> after <SEP> treatment
<tb><SEP> A <SEP> 125 <SEP> g / ha <SEP> 54 <SEP> 46
<tb><SEP> B <SEP> 250 <SEP> g / ha <SEP> 62 <SEP> 72
<tb> A <SEP> 100 <SEP> g / ha <SEP> + <SEP> 40 <SEP> 22
<tb><SEP> B <SEP> 200 <SEP> g / ha <SEP>
<tb> A <SEP> 125 <SEP> g / ha <SEP> + <SEP> 23 <SEP> 25
<tb><SEP> B <SEP> 200 <SEP> g / ha
<Tb>
We also note here very significant results with low percentages of contamination with the mixture A + B, but also a prolonged effect over time, which is not observed with compound B alone, yet used at higher dose.
a) for rust

<tb> Composition <SEP>% <SEP> of <SEP> Contamination
<tb><SEP> 46 <SEP> days <SEP> after <SEP> treatment
<tb><SEP> A <SEP> 125 <SEP> g / ha <SEP> 11
<tb><SEP> B <SEP> 250 <SEP> 3
<tb> AiOOg / ha + <SEP> O <SEP>
<tb><SEP> B <SEP> 200 <SEP> g / ha <SEP>
<tb> A125g / ha + <SEP> + <SEP>
<tb><SEP> B <SEP> 200 <SEP> g / ha
<Tb>
The mixture A + B completely protects the cultures from rust, contrary to the compounds A or B taken separately and at higher doses.

In addition, there were significant increases in crop yields
yield increased by 4 q / ha compared to treatment with
compound B alone;
> yield increased by 11 q / ha compared to treatment with
compound A alone.

 Example 3: Test on wheat (variety Appolo).

Similar tests were carried out on wheat (Appolo variety) subjected to foliar spray treatment (at a rate of 200 I / ha) of the following agrochemical compositions diluted in water:
1) Compound A (in racemic form) assayed for application to
125 g / ha;
2) Compound B assayed for application at 250 g / ha;
3) mixture A + B dosed 100 g / ha for A (in racemic form) and
200 g / ha forB;
4) mixture A + B dosed 125 g / ha for A (in racemic form) and
200 g / ha for B.

 A single application is performed for each of compositions 1 to 4.

 The disease is allowed to develop naturally, in this case Septoria tritici septoria and powdery mildew Erysiphe graminis.

After these treatments, it is estimated the proportion of plant affected by the disease by defining a percentage of contamination
100% indicates total contamination of the plant by the fungus;
0% indicates no contamination.

The following results are observed a) for Septoria

<tb> Composition <SEP>% <SEP> of <SEP> Contamination
<tb><SEP> 74 <SEP> days <SEP> after <SEP> treatment
<tb><SEP> A <SEP> 125 <SEP> g / ha <SEP> 75
<tb><SEP> B250g / ha <SEP> 80
<tb> A <SEP> 100 <SEP> g / ha <SEP> 34
<tb><SEP> B <SEP> 200 <SEP> g / ha
<tb> A <SEP> 125 <SEP> g / ha <SEP> + <SEP> 41
<tb><SEP> B <SEP> 200 <SEP> g / ha
<Tb>
A significant improvement is again provided by the mixture of compounds A + B.
(b) for powdery mildew

<tb> Composition <SEP>% <SEP> of <SEP> contamination <SEP>% <SEP> of <SEP> contamination
<tb><SEP> 39 <SEP> days <SEP> after <SEP> treatment <SEP> 74 <SEP> days <SEP> after <SEP> treatment
<tb><SEP> A <SEP> 125 <SEP> g / ha <SEP> 54 <SEP> 45
<tb><SEP> B <SEP> 250 <SEP> g / ha <SEP> 99 <SEP> 83
<tb> A <SEP> 100 <SEP> g / ha <SEP> + <SEP> 58 <SEP> 25
<tb><SEP> B2 () Og / ha <SEP>
<tb> A125g / ha + <SEP> 51 <SEP> 27
<tb><SEP> B <SEP> 200 <SEP> g / ha <SEP>
<Tb>
Very significant results are noted, especially on compound B, which has no fungicidal activity on oidium.

 Example 4: Example of Use of Non Racemic Compound A (1)

 The above three examples are similarly repeated by replacing the compound A in racemic form by the mixture of the two isomers R and S of compound A in the isomer ratio R / isomer S equal to 400.

 Doses of compound A (mixtures of isomers) represent 75% to 85% of the doses of compound A (racemic) used in the 3 previous examples.

 Results quite similar were observed. The enrichment in isomer R of the racemic therefore allows the use of a lower amount of compound A.

 Example 5: Example of Use of Non Racemic Compound A (2)

 Examples 1 to 3 above were reproduced using the pure R isomer of Compound A at doses of about 3/4 of the doses used with the racemic.

 Results quite similar were observed. The use of the R isomer in place of the racemic makes it possible to apply this compound at much lower doses. In addition, the R isomer confers a greater selectivity and a better efficiency compared to the racemic one.

Claims (10)

 A fungicidal composition comprising a compound A which is 2- (2,4-dichlorophenyl) -3- (1H-2,4,4-triazol-1-yl) propyl-1,1,2,2-tetrafluoroethyl ether, racemic form or not, and a -composition B which is the (E) - (2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate, said composition comprising the components A and B in a ratio by weight A / B of between 1/12 and 12/1, preferably between 1/4 and 4/1.  2. Fungicidal composition according to claim 1, characterized in that compound A is the R-isomer of 2- (2,4-dichlorophenyl) -3- (1H-1,2,4-triazol-1-yl) propyl-1,1,2,2-tetrafluoroethyl ether.  3. Fungicidal composition according to any one of claims 1 and 2, characterized in that the ratio A / B is between 1/4 and 4/1, and even more advantageously between 1/2 and 1/1 .  4. Fungicidal composition according to any one of claims 1 to 3, characterized in that it comprises the compounds A and B in admixture with solid or liquid carriers acceptable in agriculture and / or surfactants also acceptable in agriculture.  5. Fungicidal composition according to any one of claims 1 to 4, characterized in that it comprises from 0.05 to 95% (by weight) of active material.  6. Control method, as a curative or preventive, against phytopathogenic fungi of crops, characterized in that is applied to the aerial parts of plants or on the soil or on the multiplication products of said plants an effective amount and not phytotoxic composition of a fungicidal composition according to any one of claims 1 to 4.  7. A method for the preventive or curative treatment of plant propagation products, and plants resulting therefrom, against fungal diseases, characterized in that said products are coated with an effective and non-phytotoxic dose of a fungicidal composition according to any one of claims 1 to 4.  8. Treatment process according to claim 7, characterized in that a liquid comprising the fungicidal composition according to any one of claims 1 to 4 is sprayed onto the aerial parts of the crops to be treated.  9. Treatment process according to claim 8, characterized in that a total composition dose of between 100 and 1600 g / ha, preferably between 200 and 800 g / ha, is applied by foliar treatment.  A product comprising at least compound A and at least compound B as defined in any one of claims 1 to 4 for the fungicidal treatment of a medium by simultaneous, sequential or separate application.