WO2017162557A1 - Procédé de lutte contre la septoriose due à des souches de zymoseptoria tritici résistantes - Google Patents

Procédé de lutte contre la septoriose due à des souches de zymoseptoria tritici résistantes Download PDF

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Publication number
WO2017162557A1
WO2017162557A1 PCT/EP2017/056505 EP2017056505W WO2017162557A1 WO 2017162557 A1 WO2017162557 A1 WO 2017162557A1 EP 2017056505 W EP2017056505 W EP 2017056505W WO 2017162557 A1 WO2017162557 A1 WO 2017162557A1
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Prior art keywords
compound
prothioconazole
difenoconazole
tebuconazole
seed
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PCT/EP2017/056505
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English (en)
Inventor
Andreas MEHL
Jochen KLEEMANN
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Bayer Cropscience Aktiengesellschaft
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Priority to EP17710762.0A priority Critical patent/EP3432718A1/fr
Publication of WO2017162557A1 publication Critical patent/WO2017162557A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to a method for controlling septoria leaf blotch on cereal plants caused by Zymoseptoria tritici containing the V136A and/or 138 IV mutation, comprising treating cereal plants, their seed or the soil with a composition comprising (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II.
  • the present invention also relates to the use of a composition
  • a composition comprising (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II for controlling septoria leaf blotch on cereal plants caused by the pathogen Zymoseptoria tritici containing the V136A and/or 138 IV mutation by treating cereal plants, their seed or the soil with the composition.
  • Zymoseptoria tritici is a species of filamentous fungus, an ascomycete in the family Mycosphaerellaceae. It is a plant pathogen causing Septoria leaf blotch, which is currently the most dominant cereal disease in Western Europe and is among the top two or three most economically damaging diseases of cereals in the United States. Control of Septoria leaf blotch is becoming more and more difficult for farmers. Reason is the capability of the fungi to develop resistance to widely used powerful fungicidal agents.
  • Fungicides containing azole mixtures have been widely and successfully used in recent years for Zymoseptoria tritici control. Due to particular mutations detected in the cyp51 gene of some plant pathogens, including Zymoseptoria tritici, a sensitivity shift against particular fungicides, including azole fungicides, has been observed during the last years but not all azole fungicides are affected to the same extent.
  • a change from valine to alanine at position 136 in the cyp5 ⁇ gene - the V136A mutation - or a change from isoleucine to valine at position 381 in the cyp5 ⁇ gene - the 138 IV mutation - govern a sensitivity shift or resistance to some azoles but not all azoles are affected to the same extent. Additionally, cross-resistances of azoles have been observed. Such cross-resistances even more increase the difficulties in controlling Septoria leaf blotch caused by such resistant strains.
  • Azoles are fungicides well known as sterol biosynthesis inhibitors, see FRAC classification (FRAC website http://www/frac.info/), classified as subgroup Gl. It is in particular known that azole fungicides are inhibitors of fungal sterol C14 demethylase (cyp5 l, demethylation inhibitor (DMI) fungicides), which is a cytochrome P450 monooxygenase. Therefore, occurrence of cross-resistance between two azole fungicides having the same mode of action is not a surprise.
  • FRAC classification FRAC website http://www/frac.info/
  • the present invention comprises a method for controlling Septoria leaf blotch on cereal plants caused by Zymoseptoria tritici containing the V136A and/or 138 IV mutation, comprising treating cereal plants, their seed or the soil with a composition comprising (a) prothioconazole as compound I; and
  • the present invention comprises a method for controlling Septoria leaf blotch on cereal plants caused by Zymoseptoria tritici containing the V136A and 138 IV mutation, comprising treating cereal plants, their seed or the soil with a composition comprising (a) prothioconazole as compound I; and
  • compositions according to the present invention comprising the particular combinations of (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II excellently control Septoria leaf blotch caused by those Zymoseptoria tritici mutants.
  • compositions comprising (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II to control Zymoseptoria tritici containing the V136A and/or 138 IV mutation is important for appropriate resistance management, since Zymoseptoria tritici showing a sensitivity shift to azole applications can be successfully controlled without increasing the dosage rates. It has been found that presence of the V136A mutation increases the sensitivity of Septoria leaf blotch populations against tebuconazole and difenoconazole whereas prothioconazole shows stronger intrinsic activity on strains carrying the 138 IV mutation but not the V136A mutation.
  • prothioconazole creates a selection pressure enriching the V136A mutation in the Zymoseptoria tritici population and on the other hand application of difenoconazole or tebuconazole creates a selection pressure enriching the 138 IV mutation in the Zymoseptoria tritici population.
  • compositions according to the present invention comprising the particular combinations of (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound It can perfectly be used for controlling Zymoseptoria tritici containing the V136A and/or the 138 IV mutation, preferably for controlling Zymoseptoria tritici containing both, the V136A and/or the 138 IV mutation.
  • Containing both, the V136A and the 138 IV mutation means that both mutations are present in the pathogen population, preferably that both mutations are present in the same genome, preferably that both mutations are present in the cyp51 gene.
  • the present invention also comprises the use of a composition
  • a composition comprising
  • the present invention also comprises the use of a composition comprising
  • the use according to the invention is an important use for resistance management by controlling Zymoseptoria tritici being less susceptible to azoles.
  • the composition comprises prothioconazole as compound I and tebuconazole as compound II. In other preferred embodiments of the present invention the composition comprises prothioconazole as compound I and difenoconazole as compound II.
  • composition used according to the present invention comprises an additional active ingredient, preferably a further fungicide as compound III.
  • Such a further active ingredient can be a known fungicide, bactericide, acaricide, nematicide or insecticide, in order thus to broaden, for example, the activity spectrum or to further prevent development of resistance.
  • the weight ratio of the compound I to compound II in the composition is from 10: 1 to 1 : 10, preferably from 5: 1 to 1 :5, more preferably from 4: 1 to 1 :4, most preferably from 3: 1 to 1 :3.
  • the composition comprises a further fungicide as compound III.
  • a further fungicide can be preferably selected from the group consisting of other demethylation inhibitor (DMI) fungicides, multisite fungicides, strobilurine fungicides or succinate dehydrogenase inhibitor (SDHI) fungicides.
  • DMI demethylation inhibitor
  • SDHI succinate dehydrogenase inhibitor
  • the present invention also comprises the use of a composition comprising (a) prothioconazole as compound I; and
  • SDHI fungicides for controlling septoria leaf blotch on cereal plants caused by the pathogen Zymoseptoria tritici containing the V136A and/or 138 IV mutation by treating cereal plants, their seed or the soil with the composition SDHI fungicides are succinate dehydrogenase inhibitors, classified in group C (in particular C2: Inhibition of complex II: Succinate dehydrogenase) of the FRAC classification (FRAC website http://www/frac.info/).
  • Preferred SDHI fungicides are selected from the group consisting of bixafen (compound III- 1), fluopyram (compound III-2), fluxapyroxad (compound III-3), isopyrazam (compound III-4), bezovindiflupyr (compound III-5), pydiflumetofen (compound III-6), penthiopyrad (compound III-7) and boscalid (compound III-8) or selected from the group consisting of
  • N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-l -methyl- lH-pyrazole-4- carboxamide (compound 111-20); N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-l -methyl- lH-pyrazole-4- carboxamide (compound 111-21);
  • composition comprises one of the combinations according to Table 1.
  • compositions comprising
  • compositions comprising
  • SDHI fungicides show excellent control of septoria leaf blotch on cereal plants caused by Zymoseptoria tritici
  • the sensitivity against fungicides having this mode of action is also affected by resistant mutants.
  • the presence of a SDHI (Succinate dehydrogenase inhibitor) fungicide in combinations with azole fungicides reduces the selection pressure and the efficacy of the additional SDHI fungicide is not affected by any of the V136A and 138 IV mutations at all.
  • compositions according to the present invention comprising the particular combinations of (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II and (c) at least one SDHI fungicide as compound III can perfectly be used for decreasing the selection pressure towards one of the mutations as well as for controlling Zymoseptoria tritici containing the V136A and/or the 138 IV mutation, even preferably for controlling Zymoseptoria tritici containing the V136A and the 138 IV mutation.
  • the present invention also comprises the use of a composition comprising
  • At least one multisite fungicide as compound III for controlling septoria leaf blotch on cereal plants caused by the pathogen Zymoseptoria tritici containing the V136A and/or 138 IV mutation by treating cereal plants, their seed or the soil with the composition.
  • Multisite fungicides are fungicides having multiple modes of action, so they affect multiple target sites, and simultaneously interfere with numerous metabolic processes of the fungus. Such multisite fungicides are classified in group M ("Multi Site Action") of the FRAC classification (FRAC website http://www/frac.info/).
  • Preferred multisite fungicides are selected from the group consisting of chlorothalonil, manocozeb, propineb or folpet. Therefore, in further preferred embodiments of the present invention the composition comprises one of the combinations according to Table 1.
  • the most preferred multisite fungicide is chlorothalonil.
  • the composition comprises prothioconazole as compound I and tebuconazole as compound II and chlorothalonil as compound III.
  • composition comprises prothioconazole as compound I and difenoconazole as compound II and chlorothalonil as compound III. Also part of the present invention are novel compositions comprising
  • Such novel compositions comprise prothioconazole as compound I and difenoconazole as compound II and at least one multisite fungicide selected from the group consisting of chlorothalonil, manocozeb, propineb or folpet as compound III.
  • such novel compositions comprise prothioconazole as compound I and tebuconazole as compound II and at least one multisite fungicide selected from the group consisting of chlorothalonil, manocozeb, propineb or folpet as compound III.
  • such novel compositions comprise prothioconazole as compound I and difenoconazole as compound II and chlorothalonil as compound III.
  • such novel compositions comprise prothioconazole as compound I and tebuconazole as compound II and chlorothalonil as compound III.
  • Multisite fungicides have multiple modes of action, so that they affect multiple target sites, and simultaneously interfere with numerous metabolic processes of the fungus. Fungicide resistance occurs when a fungus develops a genetic mutation at the target site that reduces its sensitivity to a specific fungicide. Because they affect multiple target sites, multisite fungicides have a very low risk of causing fungicide resistance as it is highly unlikely for a fungus to simultaneously develop all of the mutations necessary for resistance.
  • compositions according to the present invention comprising the particular combinations of (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II and (c) at least one multisite fungicide as compound III can perfectly be used for decreasing the selection pressure towards one of the mutations as well as for controlling Zymoseptoria tritici containing the V136A and/or the 138 IV mutation, even preferably for controlling Zymoseptoria tritici containing the V136A and the 138 IV mutation.
  • Adding a further fungicide as compound III advantageously would also control septoria leaf blotch on cereal plants caused by the pathogen Zymoseptoria tritici containing the G143A mutation.
  • the present invention also comprises the use of a composition comprising (a) prothioconazole as compound I; and
  • the present invention also comprises the use of a composition comprising
  • At least one strobilurine fungicide as compound III. for controlling septoria leaf blotch on cereal plants caused by the pathogen Zymoseptoria tritici containing the V136A and 138 IV and optionally the G143A mutation by treating cereal plants, their seed or the soil with the composition.
  • the present invention also comprises the use of a composition comprising
  • difenoconazole or tebuconazole as compound II (c) at least one strobilurine fungicide as compound III. for controlling septoria leaf blotch on cereal plants caused by the pathogen Zymoseptoria tritici containing the G143A and V136A or the G143A and the 138 IV mutation, more preferably the V136A and 138 IV and G143A mutation by treating cereal plants, their seed or the soil with the composition.
  • Preferred strobilurine fungicides are selected from the group consisting of trifloxystrobin, picoxystrobin, pyraclostrobin, fluoxastrobin, azoxystrobin, dimoxystrobin and metominostrobin.
  • composition comprises one of the combinations according to Table 1.
  • the most preferred strobilurine fungicide is trifloxystrobin.
  • the composition comprises prothioconazole as compound I and tebuconazole as compound II and trifloxystrobin as compound III.
  • the composition comprises prothioconazole as compound I and difenoconazole as compound II and trifloxystrobin as compound III.
  • compositions comprising
  • such novel compositions comprise prothioconazole as compound I and difenoconazole as compound II and at least one strobilurine selected from the group consisting of trifloxystrobin, picoxystrobin, pyraclostrobin, fluoxastrobin, azoxystrobin, dimoxystrobin and metominostrobin as compound III.
  • such novel compositions comprise prothioconazole as compound I and tebuconazole as compound II and at least one strobilurine selected from the group consisting of trifloxystrobin, picoxystrobin, pyraclostrobin, fluoxastrobin, azoxystrobin, dimoxystrobin and metominostrobin as compound III.
  • such novel compositions comprise prothioconazole as compound I and difenoconazole as compound II and trifloxystrobin as compound III.
  • such novel compositions comprise prothioconazole as compound I and tebuconazole as compound II and trifloxystrobin as compound III.
  • the present invention also comprises the use of a composition comprising
  • DMI fungicides are inhibitors of fungal sterol C14 demethylase (cyp5 l, demethylation inhibitor (DMI) fungicides) which is a cytochrome P450 monooxygenase, see FRAC classification (FRAC website http://www/frac.info/), classified as subgroup Gl.
  • a preferred DMI fungicide is prochloraz.
  • the composition comprises prothioconazole as compound I and tebuconazole as compound II and prochloraz as compound III.
  • the composition comprises prothioconazole as compound I and difenoconazole as compound II and prochloraz as compound III.
  • compositions comprising
  • such novel compositions comprise prothioconazole as compound I and difenoconazole as compound II and prochloraz as compound III.
  • such novel compositions comprise prothioconazole as compound I and tebuconazole as compound II and prochloraz as compound III.
  • the weight ratio of the compound I to compound II in the composition is from 10: 1 to 1 : 10, preferably from 5: 1 to 1 :5, more preferably from 4: 1 to 1 :4, most preferably from 3: 1 to 1 :3,
  • the weight ratio of the compound I to compound III in the composition is from 10: 1 to 1 : 10, preferably from 5: 1 to 1 :5, more preferably from 4: 1 to 1 :4, most preferably from 3: 1 to 1 :3
  • the weight ratio of the compound II to compound III in the composition is from 10: 1 to 1 : 10, preferably from 5: 1 to 1 :5, more preferably from 4: 1 to 1 :4, most preferably from 3: 1 to 1 :3.
  • compositions according to the invention comprising a ternary mixture of compound I, II and III, wherein compound III is a multisite fungicide
  • the weight ratio of the compound I to compound II in the composition is from 10: 1 to 1 : 10, preferably from 5: 1 to 1 :5, more preferably from 4: 1 to 1 :4, most preferably from 3 : 1 to 1 :3
  • the weight ratio of the compound I to compound III in the composition is from 20: 1 to 1 :20, preferably from 15: 1 to 1 : 15, more preferably from 12: 1 to 1 : 12, most preferably from 10: 1 to 1 : 10
  • the weight ratio of the compound II to compound III in the composition is from 20: 1 to 1 :20, preferably from 15: 1 to 1: 15, more preferably from 12: 1 to 1 : 12, most preferably from 10: 1 to 1 : 10.
  • the cereal plants, their seed or the soil in which the plant is growing or in which it is desired to grow can be treated.
  • Treatment of plants according to the inventions also includes treatment of plant parts.
  • the compositions used according to the invention can be used to curatively or preventively control the disease.
  • Preferably the cereal plants or plant parts are treated with the compositions according to the present invention.
  • Cereals according to the present invention include wheat and triticale.
  • Compounds I or compounds II or compounds III having at least one basic centre are capable of forming, for example, acid addition salts, e.g. with strong inorganic acids, such as mineral acids, e.g. perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid, a hydrohalic acid, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, or acidic salts, such as NaHSC and KHSO4, with strong organic acids, formic acid, carbonic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, maleic acid, fumaric acid, tartaric acid, sorbic acid oxalic acid, alkylsulphonic acids (sulphonic acids having straight- chain
  • Compounds I or compounds II or compounds III having at least one acid group are capable of forming, for example, salts with bases, e.g. metal salts, such as alkali metal or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl-, diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- or tri-hydroxy-lower alkylamine, e.g. mono-, di- or tri-ethanolamine.
  • bases e.g. metal salts, such as alkali metal or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a
  • corresponding internal salts may optionally be formed.
  • any reference to the free compounds I or free compounds II or free compounds III or to their salts should be understood as including also the corresponding salts or the free compounds I or free compounds II or free compounds III, respectively, where appropriate and expedient. The same also applies to tautomers of compounds I or compounds II or compounds III and to their salts.
  • composition used according to the invention may also comprise an agriculturally acceptable support, carrier or filler.
  • support denotes a natural or synthetic, organic or inorganic compound with which the active compound I and II and optionally III is combined or associated to make it easier to apply, notably to the parts of the plant.
  • This support is thus generally inert and should be agriculturally acceptable.
  • the support may be a solid or a liquid.
  • suitable supports include clays, natural or synthetic silicates, silica, resins, waxes, solid fertilisers, water, alcohols, in particular butanol, organic solvents, mineral and plant oils and derivatives thereof. Mixtures of such supports may also be used.
  • composition may also comprise additional components.
  • the composition may further comprise a surfactant.
  • the surfactant can be an emulsifier, a dispersing agent or a wetting agent of ionic or non-ionic type or a mixture of such surfactants.
  • polyacrylic acid salts lignosulphonic acid salts, phenolsulphonic or naphthalenesulphonic acid salts
  • polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines substituted phenols (in particular alkylphenols or
  • surfactant content may be comprised from 5% to 40% by weight of the composition.
  • Colouring agents such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyanblue, and organic pigments such as alizarin, azo and metallophthalocyanine dyes, and trace elements such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts can be used.
  • additional components e.g. protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilisers, sequestering agents.
  • the active compounds can be combined with any solid or liquid additive, which complies with the usual formulation techniques.
  • the composition according to the invention may contain from 0.05 to 99% by weight of active compounds, preferably from 10 to 70%o by weight.
  • the combination or composition according to the invention can be used as such, in form of their formulations or as the use forms prepared therefrom, such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ULV) liquid, ultra low volume (ULV) suspension, water dispersible granules or tablets, water dispersible powder for s
  • compositions used according to the invention include not only compositions which are ready to be applied to the plant, seed or soil to be treated by means of a suitable device, such as a spraying or dusting device, but also concentrated commercial compositions which must be diluted before application to the plant, seed or soil.
  • the application rates can be varied within a relatively wide range, depending on the kind of application.
  • the application rate of the active ingredients used according to the invention is generally and advantageously
  • leaves • in the case of treatment of plants or plant parts, for example leaves: from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 10 to 800 g/ha, even more preferably from 25 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used);
  • compositions of the invention are particularly suitable for the treatment of seeds.
  • the invention comprises a procedure in which the seed is treated at the same time with a compound I and a compound II and optionally a compound III. It further comprises a method in which the seed is treated with compound I and compound II and optionally compound III sequentially or separately, i.e. at different times. If the single active ingredients are applied in a sequential / separate manner, i.e. at different times, they are applied one after the other within a reasonably short period, such as a few hours or days. Preferably the order of applying the compounds I and II and optionally III is not essential for working the present invention.
  • One of the advantages of the present invention is that the particular systemic properties of the active ingredients and compositions mean that treatment of the seed with these active ingredients and compositions not only protects the seed itself, but also the resulting plants after emergence, from phytopathogenic fungi. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.
  • the active ingredients or compositions can especially also be used with transgenic seed, in which case the plant growing from this seed is capable of expressing a protein which acts against pests.
  • the active ingredients or compositions By virtue of the treatment of such seed with the active ingredients or compositions, merely the expression of the protein, for example an insecticidal protein, can control certain pests. Surprisingly, a further synergistic effect can be observed in this case, which additionally increases the effectiveness for protection against attack by pests.
  • transgenic seed As also described below, the treatment of transgenic seed with the active ingredients or compositions is of particular significance. This relates to the seed of plants containing at least one heterologous gene.
  • the composition is applied to the seed alone or in a suitable formulation.
  • the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment.
  • the seed can be treated at any time between harvest and sowing. It is customary to use seed which has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content of less than 15 % by weight. Alternatively, it is also possible to use seed which, after drying, for example, has been treated with water and then dried again.
  • compositions can be applied directly, i.e. without containing any other components and without having been diluted.
  • suitable formulations and methods for seed treatment are known to those skilled in the art and are described, for example, in the following documents: US 4,272,417, US 4,245,432, US 4,808,430, US 5,876,739, US 2003/0176428 Al, WO 2002/080675, WO 2002/028186.
  • the active ingredients usable in accordance with the invention can be converted to the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seed, and also ULV formulations.
  • customary seed dressing formulations such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seed, and also ULV formulations.
  • customary additives for example customary extenders and also solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • Useful dyes which may be present in the seed dressing formulations usable in accordance with the invention are all dyes which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1.
  • Useful wetting agents which may be present in the seed dressing formulations usable in accordance with the invention are all substances which promote wetting and which are conventionally used for the formulation of active agrochemical ingredients. Preference is given to using alkyl naphthalenesulphonates, such as diisopropyl or diisobutyl naphthalenesulphonates.
  • Useful dispersants and/or emulsifiers which may be present in the seed dressing formulations usable in accordance with the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Usable with preference are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants include especially ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ether, and the phosphated or sulphated derivatives thereof. Suitable anionic dispersants are especially lignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehyde condensates.
  • Antifoams which may be present in the seed dressing formulations usable in accordance with the invention are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone antifoams and magnesium stearate can be used with preference.
  • Preservatives which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophene and benzyl alcohol hemiformal.
  • Secondary thickeners which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions.
  • Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Adhesives which may be present in the seed dressing formulations usable in accordance with the invention are all customary binders usable in seed dressing products.
  • Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
  • the gibberellins are known (cf. R. Wegler "Chemie der convinced für Schweizer- und Schadlingsbekampfungsstoff" [Chemistry of the Crop Protection Compositions and Pesticides], vol. 2, Springer Verlag, 1970, p. 401-412).
  • the seed dressing formulations usable in accordance with the invention can be used, either directly or after previously having been diluted with water, for the treatment of a wide range of different seed, including the seed of transgenic plants. In this case, additional synergistic effects may also occur in interaction with the substances formed by expression.
  • the procedure in the seed dressing is to place the seed into a mixer, to add the particular desired amount of seed dressing formulations, either as such or after prior dilution with water, and to mix everything until the formulation is distributed homogeneously on the seed. If appropriate, this is followed by a drying process.
  • the compound ratio I/II, I/III or I/II/III may be advantageously chosen so as to produce a synergistic effect.
  • a synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
  • the expected activity for a given combination of two or three active compounds can be calculated as follows (cf. Colby, S.R., "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 1967, 15, 20-22). The latter article mentions the formula for combinations of 2 active compounds:
  • Y denotes the efficacy when using active compound B (or C) at an application rate of n ppm (or g/ha),
  • Z denotes the efficacy when using active compound C at an application rate of r ppm (or g/ha),
  • Ei denotes the efficacy when using active compounds A and B at application rates of m and n ppm (or g/ha)
  • E2 denotes the efficacy when using active compounds A and B and C at application rates of m and n and r ppm (or g/ha)
  • the term “synergistic effect” also means the effect defined by application of the Tammes method, "Isoboles, a graphic representation of synergism in pesticides", Netherlands Journal of Plant Pathology, 70(1964), pages 73-80.
  • the efficacy is determined in %. 0 % means an efficacy which corresponds to that of the control, whereas an efficacy of 100 % means that no infection is observed. If the actual fungicidal action exceeds the calculated value, the action of the combination is superadditive, i.e. a synergistic effect is present. In this case, the actually observed efficacy must exceed the value calculated using the above formula for the expected efficacy (Ei or E2).
  • Zymoseptoria tritici field strains carrying cyp51 mutation V136A Spore inoculum was produced by growing fungal isolates on Czapek-Dox agar medium, supplemented with 20 % (v/v) vegetable juice and 0.3 % (w/v) calcium carbonate, for one week at 20 °C. Spores were harvested by gentle scraping the agar surface and re-suspending the obtained spore material in glucose-peptone medium. The spore suspension was adjusted to lxlO 6 spores/mL. All fungal isolates were tested with the following final test compound concentrations: 0; 0.0064; 0.032; 0.16; 0.8; 4; 20 and 100 ⁇ g active ingredient per mL.
  • Microtiter plates were prepared as follows: Ten ⁇ . of compound dilution (prepared in 80 % methanol), containing the amount of compound required for each concentration, was added to the cavities. After complete evaporation of the solvent, compounds were dissolved by adding 140 ⁇ , glucose-peptone medium per cavity, followed by overnight incubation on a rotatory shaker at 150 rpm. After adding 60 ⁇ , spore suspension into each cavity, plates were incubated at 20 °C and 90 % relative humidity for seven days on a rotatory shaker at 150 rpm. Fungal growth was determined photometrically at 620 nm.
  • EC50 values concentration at which the pathogen growth is reduced by 50 % were calculated from the resulting dose- response for each strain and active ingredient, according to the extinction values. To determine the level of cross-resistance between pairs of the tested fungicides, the correlation of their EC50 values was evaluated by calculation of Pearson's correlation coefficient for each pair. A lower correlation coefficient between the active ingredients indicates a lower level of cross-resistance between them.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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Abstract

La présente invention concerne un procédé de lutte contre la septoriose sur des plants de céréales due à Zymoseptoria tritici contenant la mutation V136A et/ou I381V, consistant à traiter des plans de céréales, leurs semences ou le sol avec une composition comprenant (a) du prothioconazole comme composé I et (b) du difénoconazole ou du tébuconazole comme composé II. La présente invention concerne également l'utilisation d'une composition comprenant (a) du prothioconazole comme composé I et (b) du difénoconazole ou du tébuconazole comme composé II pour lutter contre la septoriose sur des plants de céréales due au pathogène Zymoseptoria tritici contenant la mutation V136A et/ou I381V en traitant des plants de céréales, leurs semences ou le sol avec la composition.
PCT/EP2017/056505 2016-03-24 2017-03-20 Procédé de lutte contre la septoriose due à des souches de zymoseptoria tritici résistantes WO2017162557A1 (fr)

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CN116046942A (zh) * 2023-01-03 2023-05-02 福建省农业科学院植物保护研究所 一种区分苯醚甲环唑敏感型和抗药型玉米大斑病菌菌株的组合物和方法及应用

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019074737A1 (fr) * 2017-10-10 2019-04-18 Dow Agrosciences Llc Molécules d'acide nucléique aldéhyde déshydrogénase (aldh1) qui régulent des pathogènes
US10913955B2 (en) 2017-10-10 2021-02-09 Dow Agrosciences Llc Aldehyde dehydrogenase (ALDH1) nucleic acid molecules that control pathogens
CN116046942A (zh) * 2023-01-03 2023-05-02 福建省农业科学院植物保护研究所 一种区分苯醚甲环唑敏感型和抗药型玉米大斑病菌菌株的组合物和方法及应用
CN116046942B (zh) * 2023-01-03 2023-09-12 福建省农业科学院植物保护研究所 一种区分苯醚甲环唑敏感型和抗药型玉米大斑病菌菌株的组合物和方法及应用

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