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Dokumentenidentifikation EP0956769 14.08.2003
EP-Veröffentlichungsnummer 0956769
Titel Fungizide Mischungen
Anmelder BASF AG, 67063 Ludwigshafen, DE
Erfinder Sieverding, Ewald Gerhard, 55578 St. Johann, DE
DE-Aktenzeichen 69909365
Vertragsstaaten AT, BE, CH, DE, DK, ES, FI, FR, GB, GR, IE, IT, LI, LU, NL, PT, SE
Sprache des Dokument EN
EP-Anmeldetag 12.05.1999
EP-Aktenzeichen 993037191
EP-Offenlegungsdatum 17.11.1999
EP date of grant 09.07.2003
Veröffentlichungstag im Patentblatt 14.08.2003
IPC-Hauptklasse A01N 43/84

Beschreibung[en]
BACKGROUND OF THE INVENTION

The present invention includes a fungicidal composition comprising a fungicidally acceptable carrier and/or surface active agent and synergistically effective amounts of at least one compound of formula I, and at least one N-pyridylaniline compound.

Fungicidal N-pyridylaniline compounds are known for example from EP 0 031 257. The International patent application WO 95/04460 suggest to prepare fungicidal water dispersible granules containing 3-chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-2,6-dinitro-4-trifluoromethylbenzene and optionally other fungicidal compounds including dimethomorph.

However, until now it has not been known that the compounds of formula I with N-pyridylaniline compounds, when admixed in a tank mix or when co-formulated, would show synergistic effects. Moreover, it has not been known that a liquid concentrated composition comprising a synergistic mixture of these compounds can be advantageously be used for controlling diseases caused by oomycetes, e.g. Phytophtora infestans.

A mixture of fungicides shows synergistic effect if the fungicidal activity of the mixture is larger than the sum of activities of the separately applied compounds. The expected fungicidal activity for a given mixture of two fungicides can be calculated as follows (See Colby, S.R., "Calculating synergistic and antagonistic response of herbicide combinations", Weeds 15, pp 20-22 (1967): EE = x+y-(x.y/100) wherein

x
is the efficacy in % compared with an untreated control upon treatment with a fungicidal active ingredient A at a dose rate a;
y
is the efficacy in % compared with an untreated control upon treatment with a fungicidal active ingredient B at a dose rate b;
EE
is the expected efficacy with a combination of fungicidal active ingredients A and B at a dose of a + b, respectively.

If the actual efficacy (E) exceeds the expected (calculated) one (EE), the mixture displays a synergistic effect.

SUMMARY OF THE INVENTION

The present invention includes a liquid concentrated fungicidal composition comprising a fungicidally acceptable carrier and/or surface active agent and synergistically effective amounts of

  • (a) at least one acrylic acid morpholide of formula I
    in which

    R1 and R2 each independently represent hydrogen or halogen atom or an optionally substituted alkyl, alkoxy, alkenyl, alkynyl, alkadienyl, aryl, aryloxy, heteroaryl, cycloalkyl, cycloalkenyl, bicycloalkyl or heterocyclyl group, or an acid addition salt thereof;
  • (b) and at least one fungicidal N-pyridylaniline compound.

The fungicidal compounds of formula I to be used according to the present invention are known from European patent application EP 0 120 321.

The present invention also includes a method for controlling the growth of phythopathogenic fungi comprising application of synergistically effective amounts of at least one compound of formula I and at least one N-pyridylaniline compound as defined above.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

Surprisingly, a strong synergy between the compounds of formula I and N-pyridylaniline compounds was found when these two compounds were tank mixed or co-formulated, compared to the activity of each compound in a solo formulation.

In general terms, unless otherwise stated, as used herein the term halogen atom may denote a bromine, iodine, chlorine or fluorine atom, and is especially a bromine, chlorine or fluorine atom, in particular a bromine or chlorine atom.

Optionally substituted moieties may be unsubstituted or have from one up to the maximal possible number of substituents. Typically, 0 to 2 substituents are present. Each optionally substituted group independently may be substituted by one or more halogen atoms or nitro, cyano, cycloalkyl, preferably C3-6 cycloalkyl, cycloalkenyl, preferably C3-6 cycloalkenyl, haloalkyl, preferably C1-6 haloalkyl, halocycloalkyl, preferably C3-6 halocycloalkyl, alkoxy, preferably C1-6 alkoxy, haloalkoxy, preferably C1-6 haloalkoxy, phenyl, halo- or dihalo-phenyl or pyridyl groups.

Unless otherwise stated herein, the terms alkyl, alkenyl, alkynyl, alkadienyl and alkoxy as used herein with respect to a radical or moiety refer to a straight or branched chain radical or moiety. As a rule, such radicals have up to 10, in particular up to 6 carbon atoms. Suitably an alkyl or alkoxy moiety has from 1 to 6 carbon atoms, preferably from 1 to 5 carbon atoms. A preferred alkyl moiety is the methyl, ethyl, n-propyl, isopropyl or n-butyl group.

Unless otherwise stated herein, the term aryl, as used herein with respect to a radical or moiety refers to an aryl group having 6, 10 or 14 carbon atoms, preferably 6 or 10 carbon atoms, in particular phenyl being optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C1-6 alkyl, alkoxy, preferably C1-6 alkoxy, haloalkyl, preferably C1-6 haloalkyl, haloalkoxy, preferably C1-6 haloalkoxy groups.

Unless otherwise stated herein, the term cycloalkyl or cycloalkenyl, as used herein with respect to a radical or moiety refers to a cycloalkyl group having 3 to 8 carbon atoms or a cycloalkenyl group having 5 to 8 carbon atoms, preferably 5 to 7 carbon atoms, in particular cyclopentyl, cyclohexyl or cyclohexenyl being optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C1-6 alkyl, alkoxy, preferably C1-6 alkoxy.

Unless otherwise stated herein, the term heteroaryl, as used herein with respect to a radical or moiety, refers to an aromatic heterocyclic group having 5 or 6 ring atoms selected from carbon, nitrogen, oxygen and sulfur, at least one of which is nitrogen, oxygen or sulfur, and is optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C1-6 alkyl, alkoxy, preferably C1-6 alkoxy, in particular azolyl, triazolyl, furanyl, oxazolyl, thienyl, thiazolyl, dithiazolyl, pyridyl or pyrimidyl.

Unless otherwise stated herein, the term heterocyclyl, as used herein with respect to a radical or moiety, refers to a non-aromatic heterocyclic group having 5 or 6 ring atoms selected from carbon, nitrogen, oxygen and sulfur, at least one of which is nitrogen, oxygen or sulfur, and is optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C1-6 alkyl, alkoxy, preferably C1-6 alkoxy, in particular tetrahydropyranyl, tetrahydrofuranyl, tetrahydrothienyl, tetrahydropyridyl or tetrahydropyrimidyl.

Preferred compounds of formula I are those in which R1 and R2 are defined as follows: R1 R2 a) Cl H b) Br H c) CF3 H d) CF3O H e) propyl H f) butoxy H g) phenyl H h) 4-chlorophenoxy H i) H 3-phenoxy
Particularly preferred compounds of formula I are those wherein R1 represents a halogen atom and R2 represents a hydrogen atom.

A particularly preferred compound of formula I is dimethomorph, which is described in the "The Pesticide Manual", 10th Edition, The British Crop Protection Council and The Royal Society of Chemistry, 1994, (hereinbelow abbreviated as "Pesticide Manual"), page 351.

Preferred N-pyridylaniline compounds are the compounds of formula II,

wherein
R3 and R4
each independently represent a hydrogen or halogen atom or an optionally substituted alkyl group, preferably chloro or trifluoromethyl;
Y
each independently represents a halogen atom or an optionally substituted alkyl group, preferably chloro or trifluoromethyl;
m
is 0 or an integer of 1, 2, 3 or 4, preferably 2.

The following compounds of formula II are preferred: R3 R4 (Y)m a) CF3 Cl 3-Cl 5-CF3 b) CF3 Cl 3-Cl 5-Cl c) CF3 H 3-Cl 5-CF3 d) CF3 H 3-Cl 5-Cl e) CF3 2-hydroxyphenoxy 3-Cl 5-CF3 f) CF3 ethoxy 3-Cl 5-CF3

A particularly preferred compound of formula II is fluazinam, which is described in the "The Pesticide Manual", page 474.

Preferred fungicidal compositions of this invention include liquid concentrated co-formulations comprising the following constituents:

  • a surface active agent;
  • an acrylic acid morpholide of formula I, in particular dimethomorph;
  • at least one N-pyridylaniline compound; in particular fluazinam,
  • optionally a foam breaking agent, in particular a mixture of perfluoroalkyphosphonic acids and/or perfluoroalkylphosphinic acids, in particular Defoamer® SF or Fluowett® PL, which are commercially available from Clariant GmbH, Germany.

The compounds of formula I and the N-pyridylaniline compound are to be applied together, in synergistically effective amounts. They exhibit an extraordinary efficacy against a broad range of phytopathogenic fungi. They are systemic and may be applied as leaf or soil fungicides.

The mixture according to the invention may be preferably applied for controlling diseases caused by phytopathogenic fungi of the genera of Phythophthora, Plasmopara, Pseudoperonospora, Bremia, Peronospora, Alternaria, Guignardia, Septoria, Botrytis, Phomopsis, Rhizoctonia, and in particular of the species Phythophthora infestans and Plasmopara viticola.

The preferred application rate of the compound of formula I according to this invention is in the approximate range of 5 to 2000 grams of active ingredient (g a.i.) per hectare, with rates of about 50-500 g a.i./ha often achieving satisfactory control. The optimal rate for a specific application will depend on the crop(s) under cultivation and the predominant species of infesting fungus, and readily may be determined by established biological tests known to those skilled in the art.

In general, the preferred application rate of the N-pyridylaniline compound is in the approximate range of 20 to 500 g a.i./ha, preferably 50-300 g a.i./ha.

The optimal rate for the formula II fungicidal compound will, however, depend on the crop(s) under cultivation and the level of infestation by the fungus, and can readily be determined by established biological tests.

The preferred ratio (by weight) of the compound of formula I to the N-pyridylaniline compound is from 1:20 to 20:1, more preferably from about 1 : 10 to about 10 : 1, in particular from about 1 : 2 to about 2 : 1.

The active compounds may be formulated together in a suitable ratio according to the present invention, together with carriers and/or additives known in the art.

Accordingly, the invention further provides a concentrated liquid fungicidal composition which comprises a carrier and, as active ingredient, at least one compound of formula I as defined above and a N-pyridylaniline compound, in particular fluazinam.

A method of making such a composition is also provided, which comprises bringing a compound of formula I and a N-pyridylaniline compound into association with at least one carrier. It is also envisaged that different isomers or mixtures of isomers may have different levels or spectra of activity and thus compositions may comprise individual isomers or mixtures of isomers.

A composition according to the invention preferably contains from 0.5% to 95% by weight (w/w) of active ingredients.

A carrier useful in a composition according to the invention may include any material which facilitates application of the composition to the locus to be treated, which locus may, for example, be a plant, seed or soil, or which will facilitate storage, transport or handling. A carrier may be a solid or a liquid, including material which is normally a gas but which has been compressed to form a liquid.

The compositions may be manufactured into, e.g., emulsion concentrates, solutions, oil in water emulsions, suspension concentrates, micro-capsules, gels and other formulation types by well-established procedures. These procedures include intensive mixing and/or milling of the active ingredients with other substances, such as solvents, solid carriers, surface active compounds (surfactants), and optionally solid and/or liquid auxilaries and/or adjuvants. The form of application such as spraying, atomizing, dispersing or pouring may be chosen like the compositions according to the desired objectives and the given circumstances.

Solvents may be aromatic hydrocarbons, e.g. Solvesso® 200, substituted naphthalenes, phthalic acid esters, such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons, e.g. cyclohexane or paraffins, alcohols and glycols as well as their ethers and esters, e.g. ethanol, ethyleneglycol mono- and dimethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, or γ-butyrolactone, higher alkyl pyrrolidones, e.g. n-octylpyrrolidone or cyclohexylpyrrolidone, epoxidized plant oil esters, e.g. methylated coconut or soybean oil ester and water. Mixtures of different solvents are often suitable.

Pesticidal compositions are often formulated and transported in a concentrated form which is subsequently diluted by the user before application. The presence of small amounts of a carrier which is a surfactant facilitates this process of dilution. Thus, preferably at least one carrier in a composition according to the invention is a surfactant. For example, the composition may contain at two or more carriers, at least one of which is a surfactant.

Surfactants used in formulations of this invention may be nonionic, anionic, cationic or zwitterionic substances with good dispersing, emulsifying and wetting properties depending on the nature of the compound according to general formula I to be formulated, and may also include mixtures of individual surfactants.

The compositions of the invention may, for example, be formulated as solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols. Emulsifiable concentrates usually contain, in addition to a solvent or a mixture of solvents, 1 to 80% w/v active ingredient, 2 to 20% w/v emulsifiers and 0 to 20% w/v of other additives such as stabilizers, penetrants and corrosion inhibitors. Suspension concentrates are usually milled so as to obtain a stable, non-sedimenting flowable product and usually contain 5 to 75% w/v active ingredient, 0.5 to 15% w/v of dispersing agents, 0.1 to 10% w/v of suspending agents such as protective colloids and thixotropic agents, 0 to 10% w/v of other additives such as defoamers, corrosion inhibitors, stabilizers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation and crystalization or as antifreeze agents for water.

Aqueous dispersions and emulsions, for example compositions obtained by diluting the formulated product according to the invention with water, also lie within the scope of the invention.

Of particular interest in enhancing the duration of the protective activity of the compounds of this invention is the use of a carrier which will provide slow release of the pesticidal compounds into the environment of a plant which is to be protected as disclosed for example by U.S Patent no. 5,705,174.

The biological activity of the active ingredient can also be increased by including an adjuvant in the spray dilution. An adjuvant is defined here as a substance which can increase the biological activity of an active ingredient but is not itself significantly biologically active. The adjuvant can either be included in the formulation as a coformulant or carrier, or can be added to the spray tank together with the formulation containing the active ingredient. Preferably, linoleic acid is used as adjuvant.

As a commodity, the compositions may preferably be in a concentrated form whereas the end user generally employs diluted compositions. The compositions may be diluted to a concentration down to 0.001% of active ingredient. The doses usually are in the range from 0.01 to 10 kg a.i./ha.

Examples of formulations according to the invention are: Emulsion Concentrate (EC) active ingredient dimethomorph/fluazinam (1:1 w/w) 30 % (w/v) emulsifier(s) Atlox® 4856 B and Atlox® 4857 B 1) 5 % (w/v) (mixture containing calcium alkyl aryl sulfonate, fatty alcohol ethoxylates and light aromatics / mixture containing calcium alkyl aryl sulfonate, fatty alcohol ethoxylates and light aromatics) solvent Shellsol® A 2) (mixture of C 9 - C 10 aromatic hydrocarbons) to 1000 ml
1) Product commercially available from ICI Surfactants 2) Product commercially available from Deutsche Shell AG Suspension Concentrate (SC) active ingredient dimethomorph/fluazinam (1:1 w/w) 50 % (w/v) dispersing agent Soprophor®FL 3) (polyoxyethylene polyaryl phenyl ether phosphate amine salt) 3 % (w/v) antifoaming agent Rhodorsil® 422 3) (nonionic aqueous emulsion of polydimethylsiloxanes) 0.2 % (w/v) structure agent Kelzan® S 4) (Xanthan gum) 0.2 % (w/v) antifreezing agent Propylene glycol 5 % (w/v) biocidal agent Proxel® 5) (aqueous dipropylene glycol solution containing 20% 1,2-benisothiazolin-3-one) 0.1 % (w/v) Water to 1000 ml
3) Product commercially available from Rhone-Poulenc 4) Product commercially available from Kelco Co. 5) Product commercially available from Zeneca

A concentrated composition according to the invention preferably contains from 0.5% to 95% by weight of active ingredients.

In a preferred embodiment, the active ingredients are each added to the tank mix as a solo formulation containing a single active ingredient to form the composition of this invention.

Therefore, the present invention also relates to a kit for the preparation of a spray mixture consisting of two separate units:

  • (i) a unit which comprises at least one fungicide of formula I, conventional adjuvants and carriers;
  • (ii) a unit which comprises at least one N-pyridylaniline compound, in particular fluazinam, conventional adjuvants and carriers.

In a preferred embodiment, the said kit will consist of two bottles with dispensing means which allow the easy and correct addition of appropriate amounts of the active ingredients to the tank mix.

For a more clear understanding of the invention, specific examples are set forth below. These examples are merely illustrations and are not to be understood as limiting the scope and underlying principles of the invention in any way. Various modifications of the invention in addition to those shown and described herein will become apparent to those skilled in the art from the following examples and foregoing description. Such modifications are also intended to fall within the scope of the appended claims.

The test results described below demonstrate the enhancement in efficacy (synergy) of the combination of the compounds of formula I and N-pyridylaniline compounds of this invention.

Example 1

For this greenhouse study, formulated dimethomorph (500 g/l SC,) and commercially available formulated fluazinam (500 g/l SC, trade name SHIRLAN) were used.

Potato var. 'Bintje' were grown up in small pots and, after having obtained a height of approximately 10 cm, were sprayed with 12.5 g ai/ha of dimethomorph or fluazinam using the 'solo' products, and with the combination of 12.5 + 12.5 g ai/ha of dimethomorph + fluazinam (in-tank mixture). The spray volume was equivalent to 400 I/ha into which the products were suspended. A track sprayer with an even spray nozzle was used for the application. Five days after application of the products the plants were inoculated with a zoospore suspension of Phytophthora infestans. The plants were then transferred to a greenhouse cabinet in which the relative humidity was maintained at around 99-100%.

Disease symptoms (potato late blight) were assessed 11 and 15 days after application (DAT) of the products. The efficacy of the products was calculated in relation to the untreated plants.

The results of this evaluation are shown in Table I. 11 days efficacy (%) 15 days efficacy (%) Treatment dose (g/ha) obtained expected obtained expected dimethomorph 12.5 25 - 22 - fluazinam 12.5 37 - 27 - dimethomorph 12.5 + fluazinam 12.5 89 53 78 43
Whereas the 'solo' products provided 25 and 22% disease control (dimethomorph) and 37 and 27 % disease control (fluazinam) at 11 and 15 DAT, the in-tank mixed combination of dimethomorph with fluazinam provided 89 and 78% disease control at 11 and 15 DAT, respectively. The efficacy of the combination was clearly higher than could have been expected from the additive efficacy of the two products which would have been 53 and 43% at 11 and 15 DAT, respectively. Hence, it is clear that synergism occurred between dimethomorph and fluazinam. When an adjuvant was added to the in-tank mixture of dimethomorph plus fluazinam, the synergism was also observed.

Example 2

Effect of fungicidal SC formulations of dimethomorph and fluazinam as active ingredients in combination with an adjuvant against potato late blight.

The adjuvant is formulated as described in the following Recipe: Soprophor 796/Ba) 100 g (ethoxypropoxylated tristyrylphenol) Edenor SB 0.5 b) to 1000 ml
a) commercially available from Rhône-Poulenc b) commercially available composition consisting of about 70 % by weight of linoleic acid and about 30 % by weight of linolenic acid

The formulations were applied in a small band on the leaves, 5 days before inoculation. Fungicidal efficacy at 11 days after treatment is shown in table II: treatment dose (g/ha) efficacy (%) dimethomorph + 25 86 fluazinam 25 dimethomorph + 25 fluazinam + 25 linoleic acid 500 94 linoleic acid 500 9

The 94 % efficacy observed with the adjuvant in the mixture was higher than that predicted from the components alone according to the Colby formula (EE = 87 %).


Anspruch[de]
  1. Verfahren zur Verstärkung der Fungizidwirksamkeit von Verbindungen der Formel I
    in der
    R1 und R2
    jeweils unabhängig Wasserstoff oder Halogen oder Alkyl, Alkoxy, Alkenyl, Alkinyl, Alkadienyl, Phenyl, Phenoxy, C3-C8-Cycloalkyl oder C3-C8-Cycloalkenyl, wobei die aliphatischen Kohlenstoffketten bis zu 10 Kohlenstoffatome aufweisen,

    die durch bis zu 2 Substituenten aus der Gruppe Nitro, Cyan, C3-C6-Cycloalkyl, C3-C6-Cyclolkenyl, C1-C6-Halogenalkyl, C3-C6-Halogencycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, Phenyl oder Pyridyl substituiert sein können, bedeuten;
    mittels einer Tankmischung oder Coformulierung mit N-Pyridylanilinverbindungen der Formel II
    in der
    R3 und R4
    jeweils unabhängig Wasserstoff oder Halogen oder C1-C6-Alkyl, das wie oben definiert substituiert sein kann,
    die
    Y-Reste jeweils unabhängig ein Halogenatom oder C1-C6-Alkyl, das wie oben definiert substituiert sein kann, bedeuten und
    m
    0 oder eine ganze Zahl 1, 2, 3 oder 4 bedeutet,
    in synergistisch wirksamen Mengen.
  2. Verfahren nach Anspruch 1, wobei es sich bei der Verbindung der Formel I um Dimethomorph handelt.
  3. Verfahren nach Anspruch 2, wobei es sich bei der Verbindung der Formel II um Fluazinam handelt.
  4. Verwendung von Verbindungen der Formel I wie in den Ansprüchen 1 und 2 definiert zur Verstärkung der Fungizidwirksamkeit von Verbindungen der Formel II wie in den Ansprüchen 1 und 3 definiert.
  5. Flüssige konzentrierte fungizide Zusammensetzung enthaltend einen fungizidverträglichen Träger und/oder ein oberflächenaktives Mittel,
    • a) wenigstens eine Verbindung der Formel I, wie in den Ansprüchen 1 oder 2 definiert, und
    • b) wenigstens eine Verbindung der Formel II, wie in den Ansprüchen 1 oder 3 definiert,
    in synergistisch wirksamen Mengen.
  6. Flüssige konzentrierte fungizide Zusammensetzung gemäß Anspruch 5, zusätzlich enthaltend
    • c) Linolsäure als Hilfsstoff.
  7. Verfahren zur Bekämpfung des Wachstums eines phytopathogenen Pilzes an einem Ort, das dadurch gekennzeichnet ist, daß man eine flüssige konzentrierte fungizide Zusammensetzung wie in den Ansprüchen 5 oder 6 definiert ausbringt.
  8. Verfahren nach Anspruch 7, wobei die phytopathogenen Pilze aus der Klasse der Oomycetes stammen.
Anspruch[en]
  1. A method for enhancement of the fungicidal efficacy of compounds of formula I
    in which
    R1 and R2
    each independently represent hydrogen or halogen or alkyl, alkoxy, alkenyl, alkynyl, alkadienyl, phenyl, phenoxy, C3-C8-cycloalkyl, or C3-C8-cycloalkenyl, wherein the aliphatic carbon chains have up to 10 carbon atoms,

    which may be substituted by up to 2 substituents selected from nitro, cyano, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, phenyl or pyridyl;
    by tank mixing or co-formulating with N-pyridylaniline compounds of formula II,
    wherein
    R3 and R4
    each independently represent hydrogen or halogen or C1-C6-alkyl, which may be substituted as defined above,
    Y
    each independently represents a hologen atom or C1-C6-alkyl, which may be substituted as defined above,
    m
    is 0 or an integer of 1, 2, 3, or 4,
    in synergistically active amounts.
  2. A method according to claim 1 wherein the compound of formula I is dimethomorph.
  3. A method according to claim 1 wherein the compound of formula II is fluazinam.
  4. Use of compounds of formula I as defined in claims 1 and 2 for enhancement of fungicidal efficacy of compounds of formula II as defined in claims 1 and 3.
  5. Liquid concentrated fungicidal composition comprising a fungicidally acceptable carrier and/or a surface active agent,
    • a) at least one compound of formula I as defined in claims 1 or 2, and
    • b) at least one compound of formula II as defined in claims 1 or 3,
    in synergistically active amounts.
  6. Liquid concentrated fungicidal composition according to claim 5, comprising additionally
    • c) linoleic acid as adjuvant.
  7. A method of controlling the growth of phthopathogenic fungi at a locus which comprises applying a liquid concentrated fungicidal composition as defined in claims 5 or 6.
  8. A method according to claim 7 wherein the phytopathogenic fungi are from the class of oomycetes.
Anspruch[fr]
  1. Procédé pour renforcer l'efficacité fongicide de composés de formule I
       dans laquelle

       R1 et R2 représentent chacun indépendamment un atome d'hydrogène ou un atome d'halogène ou un groupe alkyle, un groupe alcoxy, un groupe alcényle, un groupe alcynyle, un groupe alcadiényle, un groupe phényle, un groupe phénoxy, un groupe cycloalkyle en C3 à C8 ou un groupe cycloalcényle en C3 à C8, les chaînes carbonées aliphatiques présentant jusqu'à 10 atomes de carbone, qui peuvent être substitués par jusqu'à 2 substituants choisis parmi un groupe nitro, un groupe cyano, un groupe cycloalkyle en C3 à C6, un groupe cycloalcényle en C3 à C6, un groupe haloalkyle en C1 à C6, un groupe halocycloalkyle en C3 à C6, un groupe alcoxy en C1 à C6, un groupe haloalcoxy en C1 à C6, un groupe phényle ou un groupe pyridyle ;

       en mélangeant dans une citerne ou en coformulant avec des composés N-pyridylaniline de formule II
       dans laquelle

       R3et R4 représentent chacun indépendamment un atome d'hydrogène ou un atome d'halogène ou un groupe alkyle en C1 à C6, qui peut être substitué comme défini ci-dessus,

       Y représente à chaque fois indépendamment un atome d'halogène ou un groupe alkyle en C1 à C6, qui peut être substitué comme défini ci-dessus,

       m représente 0 ou un entier représentant 1, 2, 3 ou 4

       en des quantités synergiquement actives.
  2. Procédé selon la revendication 1, dans lequel le composé de formule I est le diméthomorphe.
  3. Procédé selon la revendication 1, dans lequel le composé de formule II est le fluaziname.
  4. Utilisation de composés de formule I tels que définis dans les revendications 1 et 2 pour renforcer l'efficacité fongicide de composés de formule II tels que définis dans les revendications 1 et 3.
  5. Composition fongicide concentrée liquide comprenant un support et/ou un agent tensioactif fongiciquement acceptable,
    • a) au moins un composé de formule I tel que défini dans les revendications 1 ou 2 et
    • b) au moins un composé de formule II tel que défini dans les revendications 1 ou 3
       en des quantités synergiquement actives.
  6. Composition fongicide concentrée liquide selon la revendication 5, comprenant en plus
    • c) de l'acide linoléique comme adjuvant.
  7. Procédé pour contrôler la croissance de champignons phytopathogéniques en un endroit, qui comprend l'application d'une composition fongicide concentrée liquide telle que définie dans les revendications 5 ou 6.
  8. Procédé selon la revendication 7 dans lequel les champignons phytopathogéniques sont de la classe des oomycètes.






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