FR2742633A1 - Synergistic plant fungicide composition - Google Patents

Abstract

Fungicidal composition comprises a mixture of (A) stroliburin analogue of formula (I), and (B) dimethomorph or flumetover, the ratio of (A) to (B) being 0.1-10. In (I), A = N or CH; B = OCH2, CH2O or a group of formula (i); R1 = 1-4C alkyl (preferably Me); R2 = OMe or NHMe; X = halo, CN or 1-4C alkyl (preferably Me) with X preferably being in position 2 or 4; and n = 1 or 2; provided that when n= 2 then X may be different.

Description

Synergistic fungicidal composition comprising a similar compound
strobilurin.

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

 European patent applications EP 253213 or 398692 or international application WO 9208703 disclose strobilurin analogue compounds with a fungicidal action, making it possible to prevent the growth and development of phytopathogenic fungi that can attack crops.

 However, 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 in order to obtain a more effective product or to prevent it. 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 the number of phytosanitary treatments necessary for good pest control over time.

 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 can be achieved by the fungicidal composition of the present invention.

dans laquelle:
A est l'atome d'azote ou le groupe -CH,
B est le groupe -OCH2-, -CH20- ou le groupe

The subject of the present invention is therefore first and foremost a synergistic fungicidal composition comprising a compound A of formula (I):

in which:
A is the nitrogen atom or the group -CH,
B is the group -OCH2-, -CH20- or the group

R 1 is an alkyl group of 1 to 4 carbon atoms, preferably the methyl group,
R2 is -OCH3 or -NHCH3,
X is a halogen atom, the cyano group or an alkyl group of 1 to 4 carbon atoms, preferably the methyl group, preferably X is in position 2 and / or 4,
n is equal to 1 or 2, with when n is equal to 2 the possibility of having different groups X,
and dimethomorph or flumetover as a fungicidal compound B.

 The fungicidal composition according to the invention advantageously comprises the components A and B in a weight ratio A / B of between 0.1 and 10.

 The fungicidal composition according to the invention for which the compound A is methyl (E) -2- [2- (2-anophenoxy) pyrimidin-4-yloxy] phenyl) -3-methoxyacrylate, methyl (E) is preferred. ) -methoximino [α- (o-tolyloxy) -o-tolyl] acetate or N-methyl- (E) -methoxymino [2- (2,5-dimethylphenoxymethyl) phenyl] acetamide. Even more preferably, N-methyl (E) -methoxymino [2- (2,5-dimethylphenoxymethyl) phenyl] acetamide is preferred.

In a perfectly unexpected manner, the composition according to the invention then appreciably improves the action of the active ingredients taken separately for a certain number of fungi which are particularly harmful for crops, such as, in particular, the vine or the solaneae. This improvement is reflected in particular by a decrease in the doses of each of the constituents, which is particularly advantageous for the user and the environment. The fungicidal product thus has synergistic properties attested by the application of the method of Tammes, "Isoboles, a graphic representation of synergism in pesticides" Netherlands Journal of Plant Pathology, 70 (1964), p. 73-80 or as defined by Limpel, LE, PH Schuldt and D.Lammont, 1962, Proc.NEWCC 16: 4853, using the following formula, also called Colby's formula:
E = X + Y - XY / 100
in which:
- E is the expected percentage inhibition of growth of the fungus by a mixture of the two fungicides A and B at defined doses, respectively equal to a and b;
X is the percentage inhibition observed by the fungicide A at the dose a,
Y is the percentage inhibition observed by the fungicide B at the dose b.

When the observed percentage inhibition of the mixture is greater than E, there is synergy.

 Preferably, the weight ratio A / B is between 0.1 and 10, preferably between 0.33 and 3 for all the crops envisaged.

 Flumetover (compound B) is the common name for N-methyl-N-ethyl-4-trifluoromethyl-2- (3,4-dimethoxyphenyl) benzamide which is described in European Patent Application EP 0360701.

The structure corresponding to dimethomorph (compound B) is indicated in at least one of the two following works:
- "The pesticide manual" published by Clive TOMLIN and published by the
British Crop Protection Council, 10th edition;
- the 1996 Phytosanitary Index, published by the Association de
Agricultural Technical Coordination, 32nd edition.

 For analogous derivatives of strobilurin A, methyl (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl-3-methoxyacrylate (or ICIA5504) is described in US Pat. International Application WO 9208703; methyl- (E) methoximino [o :- (o-tolyloxy) -o-tolyl] acetate (or BAS490F) is described in European Patent Application EP 253213; N-methyl- (E) -methoxymino [2- (2,5-dimethylphenoxymethyl) phenyl] acetamide (or SSF-129) is described in European Patent Application EP 398692. Furthermore, ICIA5504 and BAS490F are listed in US Pat. book "The pesticide manual" supra.

 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 surfactants which are also agriculturally acceptable. In particular, the usual inert carriers and surfactants are usable. 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. Active ingredient means the combination of compound A with compound B.

 These compositions may also contain any other kind of 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 material, one or more solid or liquid carriers and, optionally, one or more 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 The presence of at least one surfactant is generally essential when the active ingredient and / or the inert carrier are not soluble in water and the presence of at least one surfactant. the application vector 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.

 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 active substance content in these granules being between 0.5 and 80% for the latter cases), tablets or effervescent tablets.

 The fungicidal composition according to the invention can also be used in the form of dusting powders; 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 which are liquid or intended to constitute liquid compositions during application, mention may be made of solutions, in particular water-soluble concentrates, emulsifiable concentrates, emulsions, concentrated suspensions, aerosols and powders. wettable (or powder spray), pasta, gels.

 The emulsifiable or soluble concentrates most often comprise 10 to 80% of active material, the emulsions or solutions ready for application containing, for their part, 0.001 to 20% of active ingredient.

 In addition to the solvent, the emulsifiable concentrates may contain, when necessary, 2 to 20% of appropriate additives such as stabilizers, surfactants, penetrating agents, corrosion inhibitors, dyes or adhesives previously cited.

 From these concentrates, emulsions of any desired concentration can be obtained by dilution with water, which are particularly suitable for application to crops.

As an example, here is the composition of some emulsifiable concentrates:
Example CE 1:
active ingredient 400 g / l
alkaline dodecylbenzene sulphonate 24 g / l
- Nonylphenol oxyethylated to 10 molecules
16 GB ethylene oxide
cyclohexanone 200 g / l
- aromatic solvent qsp l liter
According to another emulsifiable concentrate formula, use is made of:
Example CE 2
- active ingredient 250 g
- epoxidized vegetable oil 25 g
- Alkylaryl sulfonate mixture and
of polyglycol ether and fatty alcohols 100 g
dimethylformamide 50 g
- xylene 575 g
The concentrated suspensions, also applicable in spraying, are prepared in such a way as to obtain a stable fluid product which does not settle and usually contain from 10 to 75% of active substance, from 0.5 to 15% of surfactants, from 0 to 1 to 10% of thixotropic agents, 0 to 10% 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 may be dissolved in the support to help prevent sedimentation or as antifreezes for water.

For example, here is a concentrated suspension composition:
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, here are various compositions of wettable powders (or powders for spraying):
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, having 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 microns.

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

 The rest 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 for example 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 the half is, for example, constituted by at least one dispersing agent, essentially anionic, such as an alkaline or alkaline earth polynaphthalene sulfonate or an alkaline or alkaline earth lignosulfonate, the remainder being constituted by nonionic or anionic wetting agents such as an alkaline or alkaline earth alkyl naphthalene sulphonate.

 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 Gel: dispersible granules
In a mixer, 90% 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 microns 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.

 Finally, the subject of the invention is a method of control, as a curative or preventive action, against phytopathogenic fungi of the cultures, characterized in that an effective and non-phytotoxic quantity of a fungicidal composition is applied to the aerial parts of the plants. according to the invention.

Phytopathogenic fungi of crops that can be combated by this process include:
- from the group of oomycetes:
- of the genus Phytophthora such as Phytophthora infestans (late blight of solanaceae, in particular of potato or tomato),
Phytophthora citrophthora, Phytophthora caps here, Phytophthora cactorum,
Phytophthora palmivora, Phytophthora cinnamoni, Phytophthora megasperma,
Phytophthora parasitica,
- of the Peronosporaceae family, in particular
Plasmopara viticola (downy mildew), Plasmopara halstedei (sunflower mildew), Pseudoperonospora sp (including late blight of cucurbitaceae and hops), Bremia lactucae (late blight of lettuce), Peronospora tabacinae (tobacco blight),
- of the group of adenomycetes ::
- of the genus Alternaria, for example Altemaria solani (alternaria of solanaceae, especially tomato and potatoes),
- of the genus Guignardia, in particular Guignardia btdwellii (black rot of the vine),
- the Oidium group, for example powdery mildew (Uncinula necator); powdery mildew in vegetable crops, eg Erysiphe polygoni (cruciferous oidium); Leveillula taurica, Erysiphe cichoraceanum, Sphaerothecafuligena; (powdery mildew of cucurbits, compounds, tomato);
Erysiphe communis (powdery mildew beet and cabbage),
- of the genus Septoria, for example Septoria lycopersisi (septoria of tomato and potatoes),
- of the genus Botrytis cinerea (gray mold of the vine),
- of the genus Phomopsis viticola (excoriose of the vine).

A ranking made either by targeted fungi but by target crops can be illustrated as below:
- vine: powdery mildew (Uncinula necator), late blight (Plasmopara viticole), rot (Botrytis cinerea), excoriose (Phomopsis viticola) and black rot (Guignardia bidwellii),
- solanaceae: late blight (Phytophthora infestans), alternaria (Alternaria solani), rot (Botrytis cinerea), septoria (Septoria lycopersisi),
- vegetable crops: Mildew (Peronospora spp., Bremia lactucae, Pseudoperonospora spp.), Alternaria (Alternaria spp.), Sclerotinia (Sclerotinia spp.), Rot (Botrytis cinerea), Powdery mildew (Erysiphe spp .;
Sphaerotheca fuliginea), root or root rot (Rhizoctonia spp.),
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.

 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 the fungi present or likely to appear on the cultures, and which does not cause for said cultures any 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.

The doses of use during the implementation of the process according to the invention will then be:
on vine, vegetable crops, solanées:
50 to 500 g of dimethomorph + 50 to 500 g / ha of compound A and more precisely 100 to 300 g + 100 to 300 g / ha, ie a total dose of composition according to the invention of between 100 and 1000 g / ha, preferably between 200 and 600 g / ha.

 The following example is given purely by way of illustration of the invention, which it does not limit in any way.

 In the figure attached to this text, the dose of each active ingredient taken alone, required for the control of the phytopathogenic fungus at the indicated level, is compared with that of the 2 active ingredients taken in mixture.

The effective dose of each active ingredient taken alone is indicated on the abscissa and ordinate axis and a straight line is drawn intersecting these 2 axes and connecting these 2 doses. When an active ingredient taken alone is not effective the straight line is parallel to the coordinate axis which indicates the doses of this active ingredient. For the 2 active ingredients taken as a mixture, the dose of the mixture at a given ratio is indicated by a dot.

Example 1 In Vivo Assay of the Association of SSF-129 with Dimethomorph on Potato Late Blight (Phytophthora infestans) by Preventive Treatment 24 Hours Prior to Contamination

The test methodology was as follows:
Fungicides are used at the following doses:
SSF-129 (SC 100g / l) (A): 7.5-15-31-62-125-250 ppm,
Dimethomorph (Forum, DC 150g / l) (B): 3.8-7.5-15-31-62-125-250 ppm,
SSF-129 (A) / Dimethomorph (B) = 2: 7.5 + 3.8 at 250 + 125mg / l,
SSF-129 (A) / Dimethomorph (B) = 1: 7.5 + 7.5 to 250 + 250mg / l,
SSF-129 (A) / Dimethomorph (B) = 0.5: 7.5 + 15 at 125 + 250mg / l,
3-week-old potato (Bintge) plants are treated with the experimental fungicides at the above dosages (2 replicates / dose). One day after treatment, the plants are contaminated with a suspension of Phytophthora infestans spores (30000 spores / ml). The plants are incubated for 6 days at 18-20 ° C, 100% relative humidity (RH). Then, the disease rating is carried out after contamination by global estimation of the health status of the plants.

Compared to the control (untreated), a percentage of effectiveness is calculated. The synergy is then quantified using the model of
Colby. The results are collated in the following tables.

 Moreover, the results obtained are reported in the form of points, corresponding to 90% of destruction of the parasite and placed in an isobole diagram of Tammes which contains in abscissa the doses of B expressed in ppm (mg / l) and on the ordinate the doses of A also in ppm (mg / l).

 The diagram in FIG. 1 is obtained. It appears that the addition of dimethomorph makes it possible, quite unexpectedly, to lower the dose of A necessary for the destruction of 90% of the parasite below 250 ppm (mg / l). which corresponds to the single dose of A that it is necessary to apply to obtain the same percentage of destruction.

 The arrangement of the points obtained thus indicates a bilateral effect, qualified in the English language according to the method of Tammes cited above of "two-sided effect". This arrangement corresponds to an isobole of type m according to said method (page 75 of the corresponding bibliographic reference already cited) and is characteristic of a synergy.

Efficiencies observed:

<tb><SEP> A / B <SEP> 0 <SEP> m <SEP> mg / l <SEP> 3.8 <SEP> 7.5 <SEP> 15 <SEP> 31 <SEP> 62 <SEP> 125 <SEP> 250
<tb> O <SEP><SEP> 0% <SEP> 6.9 <SEP> 12.1 <SEP> 6.9 <SEP> 22.4 <SE> 79.3 <SE> 58.6 <SEP> 100 <SEP>
<tb><SEP> 7.5 <SEP> 12.1 <SEP> 12.1 <SEP> 12.1 <SEP> 22.4
<tb><SEP> 15 <SEP> 12.1 <SEP> 17.3 <SEP> 22.4 <SEP> 63.8
<tb><SEP> 31 <SEP> 17.3 <SEP> 37.9 <SEP> 32.8 <SEP> 89.7
<tb><SEP> 62 <SEP> 58.6 <SEP> 79.3 <SEP> 99.0 <SEP> 89.7
<tb><SEP> 125 <SEP> 87.1 <SEP> 100.0 <SEP> 99.0 <SEP> 100.0
<tb><SEP> 250 <SEP> 89.7 <SEP> 100.0 <SEP> 100.0
<Tb>
Theoretical efficiencies according to Colby ::

<tb><SEP> A / B <SEP> 0 <SEP> mg / l <SEP> 3.8 <SEP> 7.5 <SEP> 15 <SEP> 31 <SEP> 62 <SEP> 125 <SEP> 250
<tb> 0 <SEP> mg / l <SEP> 0 <SEP> 6.9 <SEP> 12.1 <SEP> 6.9 <SEP> 22.4 <SE> 79.3 <SE> 58.6 <SEP> 100
<tb><SEP> 7.5 <SEP> 12.1 <SEP> 18.2 <SEP> 22.7 <SEP> 18.2
<tb><SEP> 15 <SEP> 12.1 <SEP> 32.1 <SEP> 18.2 <SEP> 31.8
<tb><SEP> 31 <SEP> 17.3 <SEP> 23.0 <SEP> 35.8 <SE> 82.9
<tb><SEP> 62 <SEP> 58.6 <SEP> 67.9 <SEP> 91.4 <SEP> 82.9
<tb><SEP> 125 <SEP> 87.1 <SEP> 97.3 <SEP> 94.7 <SEP> 100.0
<tb><SEP> 250 <SEP> 89.7 <SEP> 99.4 <SEP> 100.0
<Tb>
Synergy (Gain in%):

<tb><SEP> A / B <SEP> 0 <SEP> m <SEP> mg / l <SEP> 3.8 <SEP> 7.5 <SEP> 15 <SEP> 31 <SEP> 62 <SEP> 125 <SEP> 250
<tb> 0 <SEP> m <SEP> mg / l <SEP> 0 <SEP> 6.9 <SEP> 12.1 <SEP> 6.9 <SEP> 22.4 <SE> 79.3 <SEP > 58.6 <SEP> 100
<tb><SEP> 7.5 <SEP> 12.1 <SEP> -6 <SEP> -11 <SEP> +4
<tb><SEP> 15 <SEP> 12.1 <SEP> -15 <SEP> +4 <SEP> +32
<tb><SEP> 31 <SEP> 17.3 <SEP> +15 <SEP> -3 <SEP> +7
<tb><SEP> 62 <SEP> 58.6 <SEP> +11 <SEP> +8 <SEP> +7
<tb><SEP> 125 <SEP> 87.1 <SEP> +3 <SEP> +4 <SEP> 0
<tb><SEP> 250 <SEP> 89.7 <SEP> +1 <SEP> 0
<Tb>

Claims (8)

B is the group -OCH2-, -CH20- or the group A is the nitrogen atom or the group -CH,  in which:

 1. A synergistic fungicidal composition comprising a compound A of formula (I):  said composition comprising components A and B in a weight ratio A / B of between 0.1 and 10.  and dimethomorph or flumetover as a fungicidal compound B;  n is equal to 1 or 2, with when n is equal to 2 the possibility of having different groups X,  X is a halogen atom, the cyano group or an alkyl group of 1 to 4 carbon atoms, preferably the methyl group, preferably X is in position 2 and / or 4,  R2 is -OCH3 or -NHCH3,  R 1 is an alkyl group of 1 to 4 carbon atoms, preferably the methyl group, 2. Fungicidal composition according to claim 1 characterized in that the compound A is the compound of formula (I) is methyl- (E) -2- (2- [6- (2-cyanophenoxy) pyrimidin4-yloxy] phenyl} 3-methoxyacrylate, methyl- (E) methoximino [a- (o-tolyloxy) -o-tolyl] acetate or N-methyl- (E) -methoxymino [2 (2,5-dimethylphenoxymethyl) phenyl] acetamide . 3. Fungicidal composition according to claim 2, characterized in that the compound A is N-methyl- (E) -methoxymino [2- (2,5-dimethylphenoxymethyl) phenyl] acetamide. 4. Fungicidal composition according to one of claims 1 to 3, characterized in that the ratio A / B is between 0.33 and 3 for all crops envisaged. 5. Fungicidal composition according to one of claims 1 to 4, characterized in that it comprises the compounds A and B in admixture with solid or liquid carriers, acceptable in agriculture and surfactants also acceptable in agriculture. 6. Fungicidal composition according to one of claims 1 to 5, characterized in that it comprises from 0.05 to 95% (by weight) of active material. 7. A method for controlling, curative or preventive, against phytopathogenic fungi of cultures, characterized in that is applied to the aerial parts of plants an effective and non-phytotoxic amount of a fungicidal composition according to one of the claims 1 to 6. 8. A method for controlling phytopathogenic fungi of cultures according to claim 7, characterized in that a dose of between 100 and 1000 g / ha, preferably between 200 and 600 g / ha, of composition is applied.