EP3429359A1 - Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals as a seed treatment - Google Patents

Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals as a seed treatment

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Publication number
EP3429359A1
EP3429359A1 EP17710540.0A EP17710540A EP3429359A1 EP 3429359 A1 EP3429359 A1 EP 3429359A1 EP 17710540 A EP17710540 A EP 17710540A EP 3429359 A1 EP3429359 A1 EP 3429359A1
Authority
EP
European Patent Office
Prior art keywords
compound
phenyl
chlorophenoxy
triazol
trifluoromethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP17710540.0A
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German (de)
French (fr)
Inventor
Markus Gewehr
Jurith Montag
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BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP3429359A1 publication Critical patent/EP3429359A1/en
Pending legal-status Critical Current

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Classifications

    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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 the use of a 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3- methyl-phenyl]-4-methyl-tetrazol-5-one (herein also referred to as compound I) for combating Microdochium nivale, which has a G143A mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors, on wheat as a seed treatment.
  • Qo inhibitor fungicides often referred to as strobilurin-type fungicides (Sauter 2007: Chapter 13.2. Strobilurins and other complex III inhibitors. In: Kramer, W.; Schirmer, U. (Ed.) - Modern Crop Protection Compounds. Volume 2. Wiley-VCH Verlag 457-495), are conventionally used to control a number of fungal pathogens in crops.
  • Qo inhibitors typically work by inhibiting respiration by binding to a ubihydroquinone oxidation center of a cytochrome bci complex (electron transport complex III) in mitochondria. Said oxidation center is located on the outer side of the inner mitochrondrial membrane.
  • Qo inhibitors A prime example of the use of Qo inhibitors includes the use of, for example, strobilurins on wheat for the control of Corynespora cassiicola (also known as Mycosphaerella graminicola), which is the cause of wheat leaf blotch.
  • Corynespora cassiicola also known as Mycosphaerella graminicola
  • pathogens In some pathogens, the major part of resistance to Qo inhibitors in agricultural uses has been attributed to pathogens containing a single amino acid residue substitution G143A in the cytochrome b gene for their cytochrome bci complex, the target protein of Qo inhibitors (see, for example Lucas, Pestic
  • Microdochium nivale show increasing resistance towards Qo inhibitors due to their G143A mutation.
  • new methods and compositions are desirable for controlling these pathogen induced diseases in crops comprising plants subjected to pathogens that are resistant to Qo inhibitors.
  • the fungicidal activity of the known fungicidal strobilurin analogue compounds is unsatisfactory, especially in case that a high proportion of the fungal pathogens contain a mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors. Based on this, it was also an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against such resistant phytopathogenic harmful fungi on wheat as a seed treatment.
  • Qo inhibitor includes any substance that is capable of diminishing and/or inhibiting respiration by binding to an ubihydroquinone oxidation center of a cytochrome bci complex in mitochondria.
  • the oxidation center is typically located on the outer side of the inner mitochrondrial membrane.
  • the compounds I have surprisingly high action against Microdochium nivale if applied as a seed treatment.
  • the present invention relates to the use of 1 -[2-[[1-(4-chlorophenyl)pyrazol-3- yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (herein also referred to as compound I) for combating Microdochium nivale, which has a G143A mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors on wheat as a seed treatment.
  • the present invention also relates to the use of a mixture comprising compound I in
  • thiabendazole metalaxyl, carboxin, thiram, thiamethoxam, flutriafol, chlotianidin, fluxapyroxad, sedaxane, fluoxastrobin, azoxystrobin and pyraclostrobin.
  • the present invention also relates to the use of a mixture comprising compound I in
  • Microdochium nivale which has a mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors is hereinafter referred to as "resistant fungi”.
  • the present invention also relates to the use of a mixture comprising compound I in
  • the present invention relates to the use of any of the mixtures M-1 to M-21 as defined in Table 1 for combating Microdochium nivale on wheat as a seed treatment.
  • the present invention preferably relates to the use of any of the mixtures of compound I and compound II for combating Microdochium nivale as a seed treatment on wheat, wherein compound II is selected from the group consisting of 2-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol, 2-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-3-methyl-1-(1 ,2,4-triazol-1 -yl)butan-2-ol, 1-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-1-cyclopropyl-2-(1 ,2,4-triazol-1-yl)ethanol, prothioconazole,
  • difenoconazole triticonazole, fludioxonil, fluxapyroxad and pyraclostrobin, wherein Y is Y1.
  • the present invention relates to the use of any of the mixtures MB-1 to MB-9 as defined in Table 2 for combating Microdochium nivale on wheat as a seed treatment.
  • the present invention also relates to the use of a mixture comprising compound I in
  • thiabendazole metalaxyl, carboxin, thiram, thiamethoxam, flutriafol, chlotianidin, fluxapyroxad, sedaxane, fluoxastrobin, azoxystrobin and pyraclostrobin for combating Microdochium nivale on wheat as a seed treatment.
  • the present invention relates to the use of any of the mixtures M4A-1 to M4A-24 as defined in Table 4A for combating Microdochium nivale on wheat as a seed treatment.
  • Table 4A
  • M4A-1 1 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- pyraclostrobin
  • use of compound I or any of the inventive mixtures for combating Microdochium nivale on wheat as a seed treatment comprises a method for controlling Microdochium nivale on wheat as a seed treatment, wherein the plant propagation material (preferably seed) are treated with an pesticidally effective amount of a compound I as defined above or a mixture of compound I with one or two compounds II.
  • effective amount means that compound I or the inventive mixtures are used in a quantity which allows obtaining the desired effect which is a synergistic control of resistant fungi, but which does not give rise to any phytotoxic symptom on the treated plant.
  • the ratio by weight of compound I and compound II in binary inventive mixtures is from 20000:1 to 1 :20000, from 500:1 to 1 :500, preferably from 100:1 to 1 :100 more preferably from 50:1 to 1 :50, most preferably from 20:1 to 1 :20, and utmost preferably ratios from 10:1 to 1 :10, which also includes ratios of 1 :5 to 5:1 ,1 :1.
  • the ratio by weight of compound I, II and second compound II in each combination of two ingredients in the mixture of three ingredients is from 20000:1 to 1 :20000, from 500:1 to 1 :500, preferably from 100:1 to 1 :100 more preferably from 50:1 to 1 :50, most preferably from 20:1 to 1 :20, and utmost preferably ratios from 10:1 to 1 :10 including also ratios from 1 :5 to 5:1 , or 1 :1.
  • Compound I or the inventive mixtures can be accompanied by further pesticides, e.g. one or more insecticides, fungicides, herbicides.
  • pesticides e.g. one or more insecticides, fungicides, herbicides.
  • compositions e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, dispersions, and mixtures thereof.
  • composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), dispersible concentrates (DC), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and
  • compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New
  • Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
  • tetrahydronaphthalene alkylated naphthalenes
  • alcohols e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol
  • glycols DMSO
  • ketones e.g. cyclohexanone
  • esters e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone
  • fatty acids phosphonates
  • amines amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e.g. cellulose, starch
  • fertilizers
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated
  • tridecylbenzenes sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • phosphates are phosphate esters.
  • carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I or the inventive mixtures on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkyliso- thiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron
  • organic colorants e.g. alizarin-, azo- and phthalocyanine colorants.
  • Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers. Examples for composition types and their preparation are:
  • alcohol alkoxylates are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%.
  • a water-soluble solvent e.g. alcohols
  • the active substance dissolves upon dilution with water.
  • polyvinylpyrrolidone are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
  • organic solvent e.g. cyclohexanone
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble organic solvent e.g. aromatic hydrocarbon
  • a compound I or the inventive mixture are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0.1 -2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0.1 -2 wt% thickener e.g. xanthan gum
  • a compound I or the inventive mixture are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a compound I or the inventive mixture are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g.
  • a compound I or the inventive mixture are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1 -5 wt% thickener e.g. carboxymethylcellulose
  • wt% of a compound I or the inventive mixture are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alcohol ethoxylate and arylphenol ethoxylate
  • Microcapsules An oil phase comprising 5-50 wt% of a compound I or the inventive mixture, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.
  • methylmethacrylate, methacrylic acid and a di- or triacrylate are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radi- cal initiator results in the formation of poly(meth)acrylate microcapsules.
  • a protective colloid e.g. polyvinyl alcohol.
  • Radical polymerization initiated by a radi- cal initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I or the inventive mixture according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
  • a polyamine e.
  • hexamethylenediamine results in the formation of polyurea microcapsules.
  • the monomers amount to 1 -10 wt%.
  • the wt% relate to the total CS composition
  • Dustable powders (DP, DS)
  • a compound I or the inventive mixture are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.
  • solid carrier e.g. finely divided kaolin
  • a compound I or the inventive mixture is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%.
  • solid carrier e.g. silicate
  • organic solvent e.g. aromatic hydrocarbon
  • compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • auxiliaries such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • the resulting agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Solutions particularly suitable for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • the compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing.
  • Methods for applying the compound I or the inventive mixtures and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material.
  • the compound I or the inventive mixtures or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • amounts of active substance of from 0.01-10kg, preferably from 0.1-1000 g, more preferably from 1-100 g per 100 kilogram of plant propagation material (preferably seeds) are generally required.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1 ) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally one or two further active components II as defined herein above.
  • Compound I according to the present invention was formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.
  • the stock solution of compound I according to the present invention was mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations.
  • MTP micro titer plate
  • a spore suspension of a sensitive and a Qol resistant isolate of Microdochium nivale in an aqueous biomalt or yeast- bactopeptone-glycerine solution was then added.
  • the plates were placed in a water vapor- saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation. The results are shown in Table 1 .
  • WO2013/092224 were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.
  • the stock solutions of compound I according to the present invention and compound 1-213 from prior art (WO2013/092224) were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations.
  • MTP micro titer plate
  • a spore suspension of a sensitive and a Qol resistant isolate of Microdochium nivale in an aqueous biomalt or yeast-bactopeptone-glycerine solution was then added.
  • the plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation. The results are shown in Table 2.

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  • Agronomy & Crop Science (AREA)
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  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

The present invention relates to the use of tetrazolinone fungicide for combating Microdochium nivale, which has a G143A mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors, on wheat as a seed treatment.

Description

Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals as a seed treatment
Description
The present invention relates to the use of a 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3- methyl-phenyl]-4-methyl-tetrazol-5-one (herein also referred to as compound I) for combating Microdochium nivale, which has a G143A mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors, on wheat as a seed treatment.
Qo inhibitor fungicides, often referred to as strobilurin-type fungicides (Sauter 2007: Chapter 13.2. Strobilurins and other complex III inhibitors. In: Kramer, W.; Schirmer, U. (Ed.) - Modern Crop Protection Compounds. Volume 2. Wiley-VCH Verlag 457-495), are conventionally used to control a number of fungal pathogens in crops. Qo inhibitors typically work by inhibiting respiration by binding to a ubihydroquinone oxidation center of a cytochrome bci complex (electron transport complex III) in mitochondria. Said oxidation center is located on the outer side of the inner mitochrondrial membrane. A prime example of the use of Qo inhibitors includes the use of, for example, strobilurins on wheat for the control of Corynespora cassiicola (also known as Mycosphaerella graminicola), which is the cause of wheat leaf blotch. Unfortunately, widespread use of such Qo inhibitors has resulted in the selection of mutant pathogens which are resistant to such Qo inhibitors (Gisi et al., Pest Manag Sci 56, 833-841 , (2000). Resistance to Qo inhibitors has been detected in several phytopathogenic fungi. In some pathogens, the major part of resistance to Qo inhibitors in agricultural uses has been attributed to pathogens containing a single amino acid residue substitution G143A in the cytochrome b gene for their cytochrome bci complex, the target protein of Qo inhibitors (see, for example Lucas, Pestic
Outlook 14(6), 268-70 (2003); and Fraaije et al., Phytopathol 95(8), 933-41 (2005), (which both are expressly incorporated by reference herein), whereas in other pathogens a substitution of F129L confers resistant to Qo inhibitors (see for example Sierotzki et al., PEST MANAGEMENT SCIENCE 63(3), 225-233 (2007); Semar et al., JOURNAL OF PLANT DISEASES AND
PROTECTION 1 14(3), 1 17-1 19 (2007); and Pasche et al., CROP PROTECTION 27(3-5), 427- 435 (2008).
In wheat, Microdochium nivale show increasing resistance towards Qo inhibitors due to their G143A mutation. Thus, new methods and compositions are desirable for controlling these pathogen induced diseases in crops comprising plants subjected to pathogens that are resistant to Qo inhibitors. Furthermore, in many cases, in particular at low application rates, the fungicidal activity of the known fungicidal strobilurin analogue compounds is unsatisfactory, especially in case that a high proportion of the fungal pathogens contain a mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors. Based on this, it was also an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against such resistant phytopathogenic harmful fungi on wheat as a seed treatment.
"Qo inhibitor," as used herein, includes any substance that is capable of diminishing and/or inhibiting respiration by binding to an ubihydroquinone oxidation center of a cytochrome bci complex in mitochondria. The oxidation center is typically located on the outer side of the inner mitochrondrial membrane.
From WO2013/092224, the use of Qo inhibitors is known for combating phytopathogenic fungi that are resistant to Qo inhibitors is generally known. However, neither Microdochium nivale as resistant pathogen nor the specific compound of formula I are not explicitly disclosed therein. Thus, there is a constant need to find further compounds with even improved action against fungi that are resistant to Qo inhibitors on top of those disclosed in WO2013/092224.
The compounds I have surprisingly high action against Microdochium nivale if applied as a seed treatment.
Thus, the present invention relates to the use of 1 -[2-[[1-(4-chlorophenyl)pyrazol-3- yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (herein also referred to as compound I) for combating Microdochium nivale, which has a G143A mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors on wheat as a seed treatment. The present invention also relates to the use of a mixture comprising compound I in
combination with a second compound II, wherein compound II is selected from
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1 -yl)propan-2-ol, 2-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1 ,2,4-triazol-1 -yl)butan-2-ol, 1-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1 ,2,4-triazol-1 -yl)ethanol, prothioconazole, difenoconazole, triticonazole, ipconazole, imidacloprid, fludioxonil,
thiabendazole, metalaxyl, carboxin, thiram, thiamethoxam, flutriafol, chlotianidin, fluxapyroxad, sedaxane, fluoxastrobin, azoxystrobin and pyraclostrobin.
The present invention also relates to the use of a mixture comprising compound I in
combination with two compounds II, wherein compound II is defined above.
Microdochium nivale, which has a mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors is hereinafter referred to as "resistant fungi". The present invention also relates to the use of a mixture comprising compound I in
combination with a second compound II, wherein compound II is selected from
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1 -yl)propan-2-ol, 2-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1 ,2,4-triazol-1 -yl)butan-2-ol, 1-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1 ,2,4-triazol-1 -yl)ethanol, prothioconazole, difenoconazole, triticonazole, ipconazole, imidacloprid, fludioxonil,
thiabendazole, metalaxyl, carboxin, thiram, thiamethoxam, flutriafol, chlotianidin, fluxapyroxad, sedaxane, fluoxastrobin, azoxystrobin and pyraclostrobin for combating Microdochium nivale on wheat as a seed treatment. Thus, the present invention relates to the use of any of the mixtures M-1 to M-21 as defined in Table 1 for combating Microdochium nivale on wheat as a seed treatment.
Table 1 Ί" is compound I, "II" is compound Ι
If mixtures are used, the present invention preferably relates to the use of any of the mixtures of compound I and compound II for combating Microdochium nivale as a seed treatment on wheat, wherein compound II is selected from the group consisting of 2-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol, 2-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-3-methyl-1-(1 ,2,4-triazol-1 -yl)butan-2-ol, 1-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-1-cyclopropyl-2-(1 ,2,4-triazol-1-yl)ethanol, prothioconazole,
difenoconazole, triticonazole, fludioxonil, fluxapyroxad and pyraclostrobin, wherein Y is Y1.
Thus, the present invention relates to the use of any of the mixtures MB-1 to MB-9 as defined in Table 2 for combating Microdochium nivale on wheat as a seed treatment.
Table 2
MB-2 I 2- [4-(4-chlorophenoxy)- 2-
(trifluoromethyl)phenyl]-
3- methyl-1 -(1 ,2,4- triazol-1 -yl)butan-2-ol MB-3 I 1 -[4-(4-chlorophenoxy)- 2-
(trifluoromethyl)phenyl]- 1 -cyclopropyl-2-(1 ,2,4- triazol-1-yl)ethanol MB-4 1 prothioconazole MB-7 1 fludioxonil
MB-5 1 difenoconazole MB-8 1 fluxapyroxad
MB-6 1 triticonazole MB-9 1 pyraclostrobin
The present invention also relates to the use of a mixture comprising compound I in
combination with a two compounds II selected from the group consisting of 2-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol, 2-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol, 1-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1 ,2,4-triazol-1 -yl)ethanol, prothioconazole, difenoconazole, triticonazole, ipconazole, imidacloprid, fludioxonil,
thiabendazole, metalaxyl, carboxin, thiram, thiamethoxam, flutriafol, chlotianidin, fluxapyroxad, sedaxane, fluoxastrobin, azoxystrobin and pyraclostrobin for combating Microdochium nivale on wheat as a seed treatment.
Thus, the present invention relates to the use of any of the mixtures M4A-1 to M4A-24 as defined in Table 4A for combating Microdochium nivale on wheat as a seed treatment. Table 4A
Ί" is com pound I, "II" is compound II"
No I II II (2)
M4A-1 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- fludioxonil
(1 ,2,4-triazol-1 -yl)propan-2-ol
M4A-2 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- fluxapyroxad
(1 ,2,4-triazol-1 -yl)propan-2-ol
M4A-3 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- pyraclostrobin
(1 ,2,4-triazol-1 -yl)propan-2-ol
M4A-4 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- triticonazole
(1 ,2,4-triazol-1 -yl)propan-2-ol
M4A-5 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3- fludioxonil
methyl-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol
M4A-6 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3- fluxapyroxad
methyl-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol
M4A-7 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3- pyraclostrobin
methyl-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol
M4A-8 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3- triticonazole
methyl-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol
M4A-9 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- fludioxonil
cyclopropyl-2-(1 ,2,4-triazol-1 -yl)ethanol
M4A-10 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- fluxapyroxad
cyclopropyl-2-(1 ,2,4-triazol-1 -yl)ethanol
M4A-1 1 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- pyraclostrobin
cyclopropyl-2-(1 ,2,4-triazol-1 -yl)ethanol M4A-12 I 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- triticonazole
cyclopropyl-2-(1 ,2,4-triazol-1 -yl)ethanol
M4A-13 I prothioconazole fludioxonil
M4A-14 I prothioconazole fluxapyroxad
M4A-15 I prothioconazole pyraclostrobin
M4A-16 I difenoconazole fludioxonil
M4A-17 I difenoconazole fluxapyroxad
M4A-18 I difenoconazole pyraclostrobin
M4A-19 I triticonazole fludioxonil
M4A-20 I triticonazole fluxapyroxad
M4A-21 I triticonazole pyraclostrobin
M4A-22 I fludioxonil fluxapyroxad
M4A-23 I fludioxonil pyraclostrobin
M4A-24 I fluxapyroxad pyraclostrobin
All above-referred mixtures are herein blow abbreviated as "inventive mixtures".
The term "use of compound I or any of the inventive mixtures for combating Microdochium nivale on wheat as a seed treatment" comprises a method for controlling Microdochium nivale on wheat as a seed treatment, wherein the plant propagation material (preferably seed) are treated with an pesticidally effective amount of a compound I as defined above or a mixture of compound I with one or two compounds II. The term "effective amount" means that compound I or the inventive mixtures are used in a quantity which allows obtaining the desired effect which is a synergistic control of resistant fungi, but which does not give rise to any phytotoxic symptom on the treated plant.
If the compound I is applied with one or two compounds II, such application can be made simultaneous that is jointly or separately, or in succession.
The ratio by weight of compound I and compound II in binary inventive mixtures is from 20000:1 to 1 :20000, from 500:1 to 1 :500, preferably from 100:1 to 1 :100 more preferably from 50:1 to 1 :50, most preferably from 20:1 to 1 :20, and utmost preferably ratios from 10:1 to 1 :10, which also includes ratios of 1 :5 to 5:1 ,1 :1.
The ratio by weight of compound I, II and second compound II in each combination of two ingredients in the mixture of three ingredients is from 20000:1 to 1 :20000, from 500:1 to 1 :500, preferably from 100:1 to 1 :100 more preferably from 50:1 to 1 :50, most preferably from 20:1 to 1 :20, and utmost preferably ratios from 10:1 to 1 :10 including also ratios from 1 :5 to 5:1 , or 1 :1.
Compound I or the inventive mixtures can be accompanied by further pesticides, e.g. one or more insecticides, fungicides, herbicides.
The compound I or the inventive mixtures can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, dispersions, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), dispersible concentrates (DC), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and
international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife
International.
The compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New
developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated
arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and
tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid
alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I or the inventive mixtures on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkyliso- thiazolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron
hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers. Examples for composition types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of a compound I or the inventive mixture and 5-15 wt% wetting agent (e.g.
alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of a compound I or the inventive mixture and 1-10 wt% dispersant (e. g.
polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC)
15-70 wt% of a compound I or the inventive mixture and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES)
5-40 wt% of a compound I or the inventive mixture and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a compound I or the inventive mixture are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0.1 -2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a compound I or the inventive mixture are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a compound I or the inventive mixture are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g.
alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a compound I or the inventive mixture are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
ix) Microemulsion (ME)
5-20 wt% of a compound I or the inventive mixture are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
x) Microcapsules (CS) An oil phase comprising 5-50 wt% of a compound I or the inventive mixture, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.
methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radi- cal initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I or the inventive mixture according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g.
hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition,
xi) Dustable powders (DP, DS)
1 -10 wt% of a compound I or the inventive mixture are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.
xii) Granules (GR, FG)
0.5-30 wt% of a compound I or the inventive mixture is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or fluidized bed.
xiii) Ultra-low volume liquids (UL)
1 -50 wt% of a compound I or the inventive mixture are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.
The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
The resulting agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
Solutions particularly suitable for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying the compound I or the inventive mixtures and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, the compound I or the inventive mixtures or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.01-10kg, preferably from 0.1-1000 g, more preferably from 1-100 g per 100 kilogram of plant propagation material (preferably seeds) are generally required.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1 ) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally one or two further active components II as defined herein above.
The invention is further illustrated, but not limited by the examples set forth below: Examples 1 Activity against snow blight Microdochium nivale in the microtiter test
Compound I according to the present invention was formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide. The stock solution of compound I according to the present invention was mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of a sensitive and a Qol resistant isolate of Microdochium nivale in an aqueous biomalt or yeast- bactopeptone-glycerine solution was then added. The plates were placed in a water vapor- saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation. The results are shown in Table 1 .
Table 1 Growth (%) Growth (%)
Cone,
Compound Microdochium nivale Qol resistant isolate of
(ppm)
sensitive Microdochium nivale compound I of the
63 0
present invention 0 5
Comparative Example: Activity against snow blight Microdochium nivale in the microtiter test Compound I according to the present invention and compound 1-213 from prior art
(WO2013/092224) were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide. The stock solutions of compound I according to the present invention and compound 1-213 from prior art (WO2013/092224) were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of a sensitive and a Qol resistant isolate of Microdochium nivale in an aqueous biomalt or yeast-bactopeptone-glycerine solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation. The results are shown in Table 2.
Table 2
The comparison of compound I according to the present invention with compound 1-213 from prior art (WO2013/092224) show the unexpected superior activity of compound I (1 -[2-[[1 -(4- chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one).

Claims

Claims
Use of a 1 -[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl- tetrazol-5-one (compound I) for combating Microdochium nivale, which has a G143A mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors on wheat as a seed treatment.
The use according to any of claims 1 , wherein compound I is applied in form of a mixture with second compound II, which is selected from the group consisting of
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol, 2-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1 ,2,4-triazol-1-yl)butan-2-ol, 1 -[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -cyclopropyl-2-(1 ,2,4-triazol-1-yl)ethanol, prothioconazole, difenoconazole, triticonazole, ipconazole, imidacloprid, fludioxonil, thiabendazole, metalaxyl, carboxin, thiram, thiamethoxam, flutriafol, chlotianidin, fluxapyroxad, sedaxane, fluoxastrobin, azoxystrobin and pyraclostrobin.
The use according to claim 1 , wherein compound I as defined in any of claims 1 to 5 is applied in form of a mixture with second compound II, which is selected from the group consisting of
2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol, 2-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1 ,2,4-triazol-1-yl)butan-2-ol, 1 -[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -cyclopropyl-2-(1 ,2,4-triazol-1-yl)ethanol, prothioconazole, difenoconazole, triticonazole, fludioxonil, fluxapyroxad and
pyraclostrobin.
The use according to any of the claims 1 to 3, wherein the ratio by weight of compound I and second compound II is 500:1 to 1 :500.
The use according to any of the claims 1 to 3, wherein the ratio by weight of compound I and second compound II is 100:1 to 1 :100.
A method for controlling Microdochium nivale on wheat as defined in any of the claims 1 to 3, wherein the plant propagation material is treated with an effective amount of a compound I or a mixture as defined in any of claims 2 to 3.
EP17710540.0A 2016-03-16 2017-03-14 Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals as a seed treatment Pending EP3429359A1 (en)

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UA120628C2 (en) 2014-11-07 2020-01-10 Басф Се Pesticidal mixtures
US11241012B2 (en) 2016-03-16 2022-02-08 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean
WO2017157920A1 (en) 2016-03-16 2017-09-21 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits
EP3429357A1 (en) 2016-03-16 2019-01-23 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals
BR112019027320B1 (en) 2017-07-05 2024-01-23 BASF Agro B.V. FUNGICIDAL MIXTURES, FUNGICIDAL COMPOSITION, METHODS FOR CONTROLLING HARMFUL PHYTOPATHOGENIC FUNGI, FOR IMPROVING THE HEALTH OF PLANTS, FOR THE PROTECTION OF PLANT PROPAGATION MATERIAL AND COATED SEED

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CA2856954C (en) * 2011-12-21 2020-09-22 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi resistant to qo inhibitors
JP6107377B2 (en) * 2012-04-27 2017-04-05 住友化学株式会社 Tetrazolinone compounds and uses thereof
JP6142752B2 (en) * 2012-09-28 2017-06-07 住友化学株式会社 Tetrazolinone compounds and uses thereof
WO2015012243A1 (en) * 2013-07-22 2015-01-29 住友化学株式会社 Plant disease control composition and application for same
WO2015012245A1 (en) * 2013-07-22 2015-01-29 住友化学株式会社 Plant disease control composition and application for same
US9781932B2 (en) * 2013-07-22 2017-10-10 Sumitomo Chemical Company, Limited Plant disease control composition and its use
EP2962568A1 (en) * 2014-07-01 2016-01-06 Basf Se Mixtures comprising a bacillus amyliquefaciens ssp. plantarum strain and a pesticide
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WO2015181035A1 (en) * 2014-05-30 2015-12-03 Basf Se Fungicidal mixtures based on 1,4-dithiine derivatives
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