WO2007039214A1 - Compositions fongicides - Google Patents

Compositions fongicides Download PDF

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Publication number
WO2007039214A1
WO2007039214A1 PCT/EP2006/009404 EP2006009404W WO2007039214A1 WO 2007039214 A1 WO2007039214 A1 WO 2007039214A1 EP 2006009404 W EP2006009404 W EP 2006009404W WO 2007039214 A1 WO2007039214 A1 WO 2007039214A1
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WO
WIPO (PCT)
Prior art keywords
plants
component
useful plants
spp
phytopathogens
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PCT/EP2006/009404
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English (en)
Inventor
Birgit Forster
Duncan Mckenzie
Colin Mills
Jeremy R. Godwin
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Syngenta Participations Ag
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Priority claimed from EP06792290A external-priority patent/EP1947940A2/fr
Publication of WO2007039214A1 publication Critical patent/WO2007039214A1/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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present invention relates to novel fungicidal compositions for the treatment of diseases of useful plants caused by phytopathogens, especially by phytopathogenic fungi, and to a method of controlling diseases on useful plants caused by phytopathogens.
  • EP-0-310-550 discloses Cyprodinil ( ⁇ -cyclopropyl- ⁇ -methyl-pyrimidin ⁇ -yO-phenyl-amine), an anilinopyrimidine fungicide which is effective against a number of diseases caused by ascomycetes or deuteromycetes.
  • Penthiopyrad (/V-[2-(1 ,3-dimethylbutyl)-3-thienyl]-1-methyl-3- (trifluoromethyl)-i /-/-pyrazole-4-carboxamide) is a fungicide which is effective against a number of diseases caused by Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Penthiopyrad Mixtures of Penthiopyrad with compounds, which act at the bci complex of the fungal mitochondrial respiratory electron transfer site, are described in WO 2006/036827.
  • Fungicidal compositions comprising a thiophene derivative and a second fungicide selected from Fludioxonil, an anilinopyrimidine, Fluazinam, lminoctadine albesilate and Polyoxin as well as their agrochemical uses are described in Japanese patent application JP-11- 302110.
  • the thiophene derivative is defined broadly and covers Penthiopyrad amongst many other thiophene derivatives.
  • the definition of the anilinopyrimidine encompasses - inter alia - Cyprodinil.
  • JP-1 1-302110 exemplifies Penthiopyrad-Fludioxonil-, Penthiopyrad- Mepanipyrim-, Penthiopyrad-lminoctadine albesilate- and Penthiopyrad-Fluazinam-mixtures and their synergistic efficacy to prevent gray mold disease (Botrytis cinerea) on peas.
  • Crop tolerance and activity against phytopathogenic plant fungi of both fungicides do not always satisfy the needs of agricultural practice in many incidents and aspects.
  • a novel synergistic composition for control of diseases on useful plants or on propagation material thereof caused by phytopathogens that in addition to inert formulation adjuvants, comprises as active ingredient a mixture of component (A) and a synergistically effective amount of component (B), wherein component (A) is Cyprodinil; and component (B) is Penthiopyrad.
  • the active ingredient mixture according to the invention not only brings about the additive enhancement of the spectrum of action with respect to the phytopathogen to be controlled that was in principle to be expected but achieves a synergistic effect which extends the range of action of the component (A) and of the component (B) in two ways. Firstly, the rates of application of the component (A) and of the component (B) are iowered whilst the action remains equally good. Secondly, the active ingredient mixture still achieves a high degree of phytopathogen control even where the two individual components have become totally ineffective in such a low application rate range. This allows, on the one hand, a substantial broadening of the spectrum of phytopathogens that can be controlled and, on the other hand, increased safety in use.
  • the pesticidal compositions according to the invention can also have further surprising advantageous properties which can also be described, in a wider sense, as synergistic activity.
  • advantageous properties that may be mentioned are: broadening of the spectrum of fungicidal activity to other phytopathogens, for example to resistant strains; improved curativity; improved rainfastness; a reduction in the rate of application of the active ingredients; more advantageous degradability; improved toxicological and/or ecotoxicological behaviour; or improved characteristics of the useful plants including: crop yields, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf colour, less fertilizers needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth and improved plant vigor.
  • a further aspect of the instant invention is a synergistic composition for control of diseases on cereal plants caused by phytopathogens, that in addition to inert formulation adjuvants, comprises as active ingredient a mixture of component (A) and a synergistically effective amount of component (B), wherein component (A) is Cyprodinil; and component (B) is Penthiopyrad.
  • a further aspect of the instant invention is a method of controlling diseases on useful plants or on propagation material thereof caused by phytopathogens, which comprises applying to the useful plants, the locus thereof or propagation material thereof a composition according to the invention.
  • a further aspect of the instant invention is a method of controlling diseases on cereal plants caused by phytopathogens, which comprises applying to the cereal plants or the locus thereof a composition according to the invention.
  • Cyprodinil and Penthiopyrad are described in ,,The Pesticide Manual” [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. Tomlin; The British Crop Protection Council] under entry numbers (208) and (1962), respectively. http://www/ Penthiopyrad and Cyprodinil can exist in different stereoisomeric forms. The invention covers mixtures comprising all those stereoisomeric forms or mixtures of those stereoisomeric forms in any ratio.
  • component (A) can be used to prepare the compositions of the invention either in the free form or as a salt or metal complex thereof.
  • hydrohalic acids s ⁇ ch as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid; sulfuric acid, phosphoric acid, nitric acid, and organic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, formic acid, benzenesulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, salicylic acid, p- aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid and 1 ,2-naphthalene- disulfonic acid.
  • hydrohalic acids s ⁇ ch as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid
  • sulfuric acid phosphoric acid,
  • Metal complexes consist of the underlying organic molecule and an inorganic or organic metal salt, for example a halide, nitrate, sulfate, phosphate, acetate, trifluoroacetate, trichloroacetate, propionate, tartrate, sulfonate, salicylate, benzoate, etc., of an element of main group II, such as calcium and magnesium, and of main groups III and IV, such as aluminium, tin or lead, and of subgroups I to VIII, such as chromium, manganese, iron, cobalt, nickel, copper, zinc, etc. Preference is given to the subgroup elements of the 4th period.
  • the metals may have any of the different valencies in which they occur.
  • the metal complexes can be mono- or poly-nuclear, i.e. they can contain one or more organic molecule components as ligands.
  • cyprodinil is used in the free form to prepare the compositions of the invention.
  • composition stands for the various mixtures or combinations of components A) and B), for example in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • the order of applying the components A) and B) is not essential for working the present invention.
  • compositions according to the invention are effective against harmful microorganisms, such as microorganisms, that cause plant diseases, in particular against phytopathogenic fungi and bacteria.
  • compositions according to the invention are effective especially against phytopathogenic fungi belonging to the following classes: Ascomycetes (e.g. Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula, Botrytis, Helminthosporium, Fusarium, Septoria, Cercospora, Rhynchosporium, Pyricularia and Pseudocercosporella); Basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); Fungi imperfecti (also known as Deuteromycetes; e.g. Alternaria).
  • Ascomycetes e.g. Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula, Botrytis, Helminthosporium, Fusarium, Sept
  • useful plants typically comprise the following species of plants: grape vines; cereals, such as wheat, barley, rye or oats; beet, such as sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas or soybeans; oil plants, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans or groundnuts; cucumber plants, such as marrows, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruit or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceae, such as avocados, cinnamon or camphor; maize; tobacco
  • useful plants is to be understood as including also useful plants that have been rendered toierant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • EPSPS 5-enol-pyrovyl-shikimate-3-phosphate-synthase
  • GS glutamine synthetase
  • PPO protoporphyrinogen-oxidase
  • imazamox by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola).
  • crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®.
  • useful plants is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
  • Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, for example insecticidal proteins from Bacillus cereus or Bacillus popliae; or insecticidal proteins from Bacillus thuringiensis, such as ⁇ -endotoxins, e.g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bi) or Cry9c.
  • useful plants is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-O 392 225).
  • PRPs pathogenesis-related proteins
  • Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-O 392 225, WO 95/33818, and EP-A-O 353 191.
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1 , KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; the so-called "pathogenesis-related proteins" (PRPs; see e.g. EP-A-O 392 225); antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g. WO 95/33818) or protein or polypeptide factors invoived in plant pathogen defence (so-called "plant disease resistance genes", as described in WO 03/000906).
  • ion channel blockers such as blockers for sodium and calcium channels
  • the viral KP1 , KP4 or KP6 toxins stilbene synthases; bibenzyl synthases; chitinases; glucanases; the
  • Useful plants of elevated interest in connection with present invention are cereals; soybean; rice; oil seed rape; pome fruits; stone fruits; peanuts; coffee; tea; strawberries; turf; vines and vegetables, such as tomatoes, potatoes, cucurbits and lettuce.
  • locus of a useful plant as used herein is intended to embrace the place on which the useful plants are growing, where the plant propagation materials of the useful plants are sown or where the plant propagation materials of the useful plants will be placed into the soil.
  • An example for such a locus is a field, on which crop plants are growing.
  • plant propagation material is understood to denote generative parts of a plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes.
  • vegetative material such as cuttings or tubers, for example potatoes.
  • plant propagation material is understood to denote seeds.
  • the compositions according to the invention are particularly effective against powdery mildews; rusts; leafspot species; early blights and molds; especially against Septoria, Puccinia, Erysiphe, Rhynchosporium, Pyrenophora and Tapesia in cereals; Phakopsora in soybeans; Hemileia in coffee; Phragmidium in roses; Altemaria in potatoes, tomatoes and cucurbits; Sclerotinia in turf, vegetables, sunflower and oil seed rape; black rot, red fire, powdery mildew, grey mold and dead arm disease in vine; Botrytis cinerea in fruits; Venturia and Monilinia spp. in fruits and Penicillium spp. in fruits.
  • compositions according to the invention are furthermore particularly effective against seedborne and soilborne diseases, such as Altemaria spp., Ascochyta spp., Botrytis cinerea, Cercospora spp., Claviceps purpurea, Cochliobolus sativus, Colletotrichum spp., Epicoccurn spp., Fusarium graminearum, Fusarium moniliforme, Fusarium oxysporum, Fusarium proliferatum, Fusarium solani, Fusarium subglutinans, Gaumannomyces graminis , Helminthosporium spp., Microdochium nivale, Phoma spp., Pyrenophora graminea, Pyricularia oryzae, Rhizoctonia solani, Rhizoctonia cerealis, Sclerotinia spp., Septoria spp., Sphacelotheca reilliana,
  • Verticillium spp. in particular against pathogens of cereals, such as wheat, barley, rye or oats; maize; rice; cotton; soybean; turf; sugarbeet; oil seed rape; potatoes; pulse crops, such as peas, lentils or chickpea; and sunflower.
  • compositions according to the invention are furthermore particularly effective against post harvest diseasese such as Botrytis cinerea, Colletotrichum musae, Curvularia lunata, Fusarium semitecum, Geotrichum candidum, Monilinia fructicola, Monilinia f ructigena, Monilinia laxa, Mucor piriformis, Penicilium italicum, Penicilium solitum, Penicillium digitatum or Penicillium expansum in particular against pathogens of fruits, such as pomefruits, for example apples and pears, stone fruits, for example peaches and plums, citrus, melons, papaya, kiwi, mango, berries, for example strawberries, avocados, pomegranates and bananas, and nuts.
  • post harvest diseasese such as Botrytis cinerea, Colletotrichum musae, Curvularia lunata, Fusarium semitecum, Geotrichum candidum, Monilinia fructicola, Monilini
  • the amount of a composition according to the invention to be applied will depend on various factors, such as the compounds employed; the subject of the treatment, such as, for example plants, soil or seeds; the type of treatment, such as, for example spraying, dusting or seed dressing; the purpose of the treatment, such as, for example prophylactic or therapeutic; the type of fungi to be controlled or the application time. It has been found that the use of component B) in combination with component A) surprisingly and substantially enhance the effectiveness of the latter against fungi, and vice versa. Additionally, the method of the invention is effective against a wider spectrum of such fungi that can be combated with the active ingredients of this method, when used solely.
  • the weight ratio of A): B) is so selected as to give a synergistic activity.
  • the weight ratio of A) : B) is between 2000 : 1 and 1 : 1000, preferably between 100 : 1 and 1 : 100, more preferably between 20 : 1 and 1 : 50, most preferably between 10 : 1 and 1 : 10.
  • compositions according to the invention is apparent from the fact that the fungicidal activity of the composition of A) + B) is greater than the sum of the fungicidal activities of A) and B).
  • the method of the invention comprises applying to the useful plants, the locus thereof or propagation material thereof in admixture or separately, a composition according to the invention.
  • compositions according to the invention have a systemic action and can be used as foliar, soil and seed treatment fungicides.
  • compositions according to the invention it is possible to inhibit or destroy the phytopathogenic microorganisms which occur in plants or in parts of plants (fruit, blossoms, leaves, stems, tubers, roots) in different useful plants, while at the same time the parts of plants which grow later are also protected from attack by phytopathogenic microorganisms.
  • compositions according to the invention are of particular interest for controlling a large number of fungi in various useful plants or their seeds, especially in field crops such as potatoes, tobacco and sugarbeets, and wheat, rye, barley, oats, rice, maize, lawns, cotton, soybeans, oil seed rape, pulse crops, sunflower, coffee, sugarcane, fruit and ornamentals in horticulture and viticulture, in vegetables such as cucumbers, beans and cucurbits.
  • the compositions according to the invention are applied by treating the fungi, the useful plants, the locus thereof or the propagation material thereof with a composition according to the invention.
  • compositions according to the invention may be applied before or after infection of the useful plants or the propagation material thereof by the fungi.
  • compositions according to the invention are particularly useful for controlling the following plant diseases on useful plants:
  • Blumeria species (formerly known as Erysiphe species) in cereals; such as Blumeria graminis f. sp. hordei (formerly known as Erysiphe graminis) in barley and Blumeria graminis f. sp. tritici (formerly known as Erysiphe graminis) in wheat;
  • Phakopsora species in soybeans such as Phakopsora pachyrizi in soybeans
  • Puccinia species in cereals, broadleaf crops and perennial plants such as Puccinia recondita on wheat, Puccinia striiformis on wheat and Puccinia recondita on barley;
  • Pseudocercosporella species in cereals such as Pseudocercosporella herpotrichoides in wheat;
  • Podosphaera species in fruits such as Pyrenophora teres on barley;
  • Rhizoctonia species in cotton, soybean, cereals, maize, potatoes, rice and lawns such as
  • Sclerotinia species in lawns, lettuce, vegetables and oil seed rape such as Sclerotinia sclerotiorum on oilseed rape and Sclerotinia homeocarpa on turf;
  • Venturia species in fruits such as Venturia inequalis on apple
  • Penicillium species on citrus and apples are Penicillium species on citrus and apples.
  • component A When applied to the useful plants component A) is applied at a rate of 5 to 2000 g a.i./ha, particularly 10 to 1000 g a.i./ha, e.g. 15, 25, 50, 300, 400, 500, 600 or 750 g a.i./ha, in association with 1 to 5000 g a.i./ha, particularly 2 to 2000 g a.i./ha, e.g. 100, 250, 500, 800, 1000, 1500 g a.L/ha of a compound of component B).
  • component A) is applied to the useful plants at a rate of 10 to 1000 g a.i./ha, e.g. 15, 25, 50, 300, 400, 500, 600 or 750 g a.i./ha, in association with 2 to 1000 g a.L/ha, e.g. 50, 75, 100, 150, 250, 500, 750, 1000 g a.L/ha of a compound of component B).
  • component (A) is applied to the useful plants at a rate of 10 to 500 g a.i./ha, particularly 20 to 200 g a.i./ha, e.g. 20, 50, 80, 100 or 200 g a.L/ha, in association with 10 to 500 g a.i./ha, particularly 50 to 150 g a.i./ha, e.g. 50, 75, 100, 150 g a.i./ha of component (B).
  • compositions according to the invention depend on the type of effect desired, and typically range from 20 to 4000 g of total composition per hectare.
  • compositions according to the invention are applied to the useful plants at a rate of 50 to 500 g of total composition per hectare.
  • compositions according to the invention are used for treating seed, rates of 0.001 to 10 g of Cyprodini! per kg of seed, preferably from 0.01 to 1 g per kg of seed, and 0.001 to 50 g of a compound of component B), per kg of seed, preferably from 0.01 to 10g per kg of seed, are generally sufficient.
  • composition of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK),
  • compositions may be produced in conventional manner, e.g. by mixing the active ingredients with appropriate inert formulation adjuvants (diluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects).
  • inert formulation adjuvants diiluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects.
  • conventional slow release formulations may be employed where long lasting efficacy is intended.
  • Particularly formulations to be applied in spraying forms such as water dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g.
  • compositions according to the invention may comprise one or more additional active ingredient, such as a fungicide, insecticide, herbicide or growth regulator.
  • a seed dressing formulation is applied in a manner known per se to the seeds employing the compositions according to the invention and a diluent in suitable seed dressing forrnuiation form, e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • suitable seed dressing forrnuiation form e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • seed dressing formulations are known in the art.
  • Seed dressing formulations may contain the single active ingredients or the combination of active ingredients in encapsulated form, e.g. as slow release capsules or microcapsules.
  • the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts and adjuvant(s), the active agent consisting of at least the compound of formula I together with a compound of component B), and optionally other active agents, particularly microbiocides or conservatives or the like.
  • Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 70% by weight of active agent.
  • Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.
  • active ingredient denoting a mixture of cyprodinil (component A) and Penthiopyrad (component B) in a specific mixing ratio.
  • the active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
  • the active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • Emulsifiable concentrate active ingredient [A): B) 1 :6 (a), 1 :5 (b)] 10 % octylphenol polyethylene glycol ether 3 %
  • Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water. Dusts a) b) c)
  • Active ingredient [A) : B) 1 :6(a), 1 :2(b), 1 :10(c)] 5 % 6 % 4 %
  • Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
  • Active ingredient (A) : B) 2: 1 ) 15 % sodium iignosuifonate 2 % carboxymethylcellulose 1 %
  • the active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water.
  • the mixture is extruded and then dried in a stream of air.
  • Active ingredient [A): B) 1 :10 (a), 1 :5 (b)] 8 % polyethylene glycol (mol. wt. 200) 3 %
  • the finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
  • Suspension concentrate active ingredient [A): B) 1 :8 (a), 1 :5 (b)] 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • Flowable concentrate for seed treatment active ingredient (A) : B) 1 :8) 40 % propylene glycol 5 % copolymer butanol PO/EO 2 % tristyrenephenole with 10-20 moles EO 2 %
  • Silicone oil (in the form of a 75 % emulsion in water) 0, .2 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • 28 parts of a combination of cyprodinil and a compound of component B), or of each of these compounds separately, are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1).
  • This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved.
  • a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed.
  • the obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent.
  • the capsule suspension formulation contains 28% of the active ingredients.
  • the medium capsule diameter is 8-15 microns.
  • a further aspect of the instant invention is a method of controlling diseases on useful plants caused by phytopathogens, which comprises applying to the useful plants or the locus thereof a composition according to the invention.
  • a further aspect of the instant invention is a method of controlling diseases on useful plants caused by phytopathogens, which comprises applying to the useful plants a composition according to the invention.
  • a further aspect of the instant invention is a method of controlling diseases on cereal plants caused by phytopathogens, which comprises applying to the cereal plants or to the locus thereof a composition according to the invention; prefered cereal plants are wheat or barley.
  • a method of controlling diseases on wheat plants caused by phytopathogens which comprises applying to the wheat plants or to the locus thereof a composition according to the invention, wherein the disease is selected from
  • Blumeria graminis (Erysiphe graminis), Pseudocercosporella herpotrichoides, Puccinia recondita, Puccinia striiformis, Pyrenophora tritici-repentis, Septoria tritici and Tapesia spp.
  • a method of controlling Pseudocercosporella herpotrichoides or Septoria tritici on wheat plants which comprises applying to the wheat plants or to the locus thereof a composition according to the invention.
  • a method of controlling Pseudocercosporella herpotrichoides on wheat plants which comprises applying to the wheat plants or to the locus thereof a composition according to the invention.
  • a method of controlling Septoria tritici on wheat plants which comprises applying to the wheat plants or to the locus thereof a composition according to the invention.
  • a method of controlling Tapesia spp. on wheat plants which comprises applying to the wheat plants or to the locus thereof a composition according to the invention.
  • a method of controlling Blumeria graminis f. sp. tritici on wheat plants which comprises applying to the wheat plants or to the locus thereof a composition according to the invention.
  • a method of controlling diseases on barley plants caused by phytopathogens which comprises applying to the barley plants or to the locus thereof a composition according to the invention, wherein the disease is selected from Blumeria graminis (Erysiphe graminis), Puccinia recondita, Pyrenophora teres, Ramularia collo-cygni and Rhynchosporium secalis; prefered is a method, wherein the disease is selected from Blumeria graminis (Erysiphe graminis), Puccinia recondita, Pyrenophora teres, Ramularia collo-cygni and Rhynchosporium secalis; prefered is a method, wherein the disease is selected from Blumeria graminis (Erys
  • a method of controlling Pyrenophora teres on barley plants which comprises applying to the barley plants or to the locus thereof a composition according to the invention.
  • a method of controlling Ramularia collo-cygni on barley plants which comprises applying to the barley plants or to the locus thereof a composition according to the invention.
  • a method of controlling Rhynchosporium secalis on barley plants which comprises applying to the barley plants or to the locus thereof a composition according to the invention.
  • a method of controlling Blumeria graminis f. sp. hordei on barley plants which comprises applying to the barley plants or to the locus thereof a composition according to the invention.
  • a further aspect of the instant invention is a method of controlling diseases on fruit plants or vegetable plants caused by phytopathogens, which comprises applying to the fruit plants or vegetable plants or to the locus thereof a composition according to the invention; prefered fruit plants are apple, citrus, pear, strawberry or banana; prefered vegetable plants are tomato; potato; cucurbit, such as cucumber or melon; leafy vegetables, such as lettuce, spinach or celery; brassica, such as cabbage, cauliflower, oilseed rape, broccoli or brussels sprouts; allium, such as onion or leek; root crops, such as sugar beet, carrots or parsnips; or legumes, such as peas or beans.
  • a method of controlling diseases on fruit plants or vegetable plants caused by phytopathogens which comprises applying to the fruit plants or vegetable plants or to the locus thereof a composition according to the invention, wherein the disease is selected from Botrytis spp, Venturia spp, Altemaria spp, Bremia spp, Diaporthe spp, Mycosphaerella spp, Sphaerotheca spp, Phytopthora spp, Perenospora spp, Pseudoperonospora spp, Pythium spp, Plasmopara spp, Sclerotinia spp, Phoma spp and Colletotrichum spp; prefered is a method, wherein the disease is selected from Botrytis spp and Venturia spp.
  • a method of controlling diseases on fruit plants caused by phytopathogens which comprises applying to the fruit plants or to the locus thereof a composition according to the invention, wherein the fruit plant is selected from apple, citrus, pear, strawberry and banana, and wherein the disease is selected from Botrytis spp, Venturia spp, Alternaria spp, Bremia spp, Diaporthe spp, Mycosphaerella spp, Sphaerotheca spp, Phytopthora spp, Perenospora spp, Pseudoperonospora spp, Pythium spp, Plasmopara spp, Sclerotinia spp, Phoma spp and Colletotrichum spp; prefered is a method, wherein the disease is Venturia spp.
  • a method of controlling Venturia spp. on apple plants which comprises applying to the apple plants or to the locus thereof a composition according to the invention.
  • a method of controlling diseases on vegetable plants caused by phytopathogens which comprises applying to the vegetable plants or to the locus thereof a composition according to the invention, wherein the vegetable plant is selected from tomato, potato, cucumber, lettuce, spinach, celery, cabbage, cauliflower, oilseed rape, broccoli, brussels sprouts, onion, leek, sugar beet, carrots, parsnips, peas and beans, and wherein the disease is selected from Botrytis spp, Venturia spp, Alternaria spp, Bremia spp, Diaporthe spp, Mycosphaerella spp, Sphaerotheca spp, Phytopthora spp, Perenospora spp, Pseudoperonospora spp, Pythium spp, Plasmopara spp, Sclerotinia spp, Phoma spp and Colletotrichum spp; prefered is a method, wherein the vegetable plant is selected from
  • a method of controlling Botrytis spp. on tomato plants which comprises applying to the tomato plants or to the locus thereof a composition according to the invention.
  • a method of controlling Botrytis cinerea on tomato plants which comprises applying to the tomato plants or to the locus thereof a composition according to the invention.
  • a further aspect of the instant invention is a method of controlling diseases on grape plants caused by phytopathogens, which comprises applying to the grape plants or to the locus thereof a composition according to the invention.
  • a method of controlling diseases on grape plants caused by phytopathogens which comprises applying to the grape plants or to the locus thereof a composition according to the invention, wherein the disease is selected from Botrytis cinerea, Uncinula necator, Guignardia bidwellii and Plasmopara viticola; prefered is a method, wherein the disease is Botrytis cinerea.
  • a further aspect of the instant invention is a composition for control of diseases on useful plants caused by phytopathogens, that in addition to inert formulation adjuvants, comprises as active ingredients a component (A) and a synergistically effective amount of a component (B); wherein component (A) is Cyprodinil; and component (B) is Penthiopyrad; with the proviso that if further compounds are present, which act at the bc ⁇ complex of the fungal mitochondrial respiratory electron transfer site, said compounds are selected from group consisting of Azoxystrobin, Kresoxim-methyl, Dimoxystrobin and Metominostrobin.
  • compositions according to the invention comprise, besides Cyprodinil and Penthiopyrad, a further active ingredient and said active ingredient acts at the bc ⁇ complex of the fungal mitochondrial respiratory electron transfer site, said further active ingredient is selected from group consisiting of Azoxystrobin, Kresoxim-methyl, Dimoxystrobin and Metominostrobin.
  • Azoxystrobin, Kresoxim-methyl, Dimoxystrobin and Metominostrobin are described in ,,The Pesticide Manual” [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. Tomlin; The British Crop Protection Council] under entry numbers (47), (485), (226) and (551 ), respectively.
  • Strobilurin fungicides such as Azoxystrobin, Kresoxim-methyl, Dimoxystrobin and Metominostrobin, and the related fungicides famoxadone and fenamidone are known to have a fungicidal mode of action which inhibits the bc ⁇ complex of the fungal mitochondrial respiratory electron transfer site (Angew. Chem. Int. Ed. 1999, 38, 1328-1349 and Pest Management Science 2002, 58, 649-662).
  • the ⁇ c 1 complex is sometimes referred to by other names in the biochemical literature, including complex III of the electron transfer chain and ubihydroquinonercytochrome c oxidoreductase.
  • the invention provides a composition for control of diseases on useful plants caused by phytopathogens, that in addition to inert formulation adjuvants, comprises as active ingredients a component (A) and a synergistically effective amount of a component (B); wherein component (A) is Cyprodinil; and component (B) is Penthiopyrad; with the exception of compositions having as active ingredient a mixture comprising Cyprodinil, Penthiopyrad and a compound, which acts at the bc ⁇ complex of the fungal mitochondrial respiratory electron transfer site.
  • compositions according to the invention do not comprise an additional active ingredient.
  • This embodiment provides a composition for control of diseases on useful plants caused by phytopathogens, that in addition to inert formulation adjuvants, comprises an active ingredient, which consists essentially of a component (A) and a synergistically effective amount of a component (B); wherein component (A) is Cyprodinil; and component (B) is Penthiopyrad.
  • the active ingredient consists of a component (A) and a synergistically effective amount of a component (B); wherein component (A) is Cyprodinil; and component (B) is Penthiopyrad.
  • a further aspect of the instant invention is a composition for control of diseases on cereal plants caused by phytopathogens, that in addition to inert formulation adjuvants, comprises as active ingredients a component (A) and a synergistically effective amount of a component (B); wherein component (A) is Cyprodinil; and component (B) is Penthiopyrad; preferred are compositions for the control of Pseudocercosporella herpotrichoides, Pyrenophora teres or Septoria tritici.
  • a further aspect of the instant invention is a composition for control of diseases on wheat plants caused by phytopathogens, that in addition to inert formulation adjuvants, comprises as active ingredients a component (A) and a synergistically effective amount of a component (B); wherein component (A) is Cyprodinil; and component (B) is Penthiopyrad; preferred are compositions for the control of Pseudocercosporella herpotrichoides or Septoria tritici.
  • a further aspect of the instant invention is a composition for control of diseases on barley plants caused by phytopathogens, that in addition to inert formulation adjuvants, comprises as active ingredients a component (A) and a synergistically effective amount of a component (B); wherein component (A) is Cyprodinil; and component (B) is Penthiopyrad; preferred are compositions for the control of Pyrenophora teres.
  • a synergistic effect exists whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components.
  • Example B-1 Action against Pyrenophora teres (causal fungus of net blotch on barley) a) Fungal growth assay
  • Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically after 7 days. The fungicide interactions in the combinations are calculated according to the COLBY method. The data generated in this experiment indicate synergy between penthiopyrad and cyprodinil when used in mixture with one another.
  • Barley leaf segments are placed on agar in muitiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed 96 hrs after inoculation as preventive fungicidal activity.
  • the fungicide interactions in the combinations are calculated according to COLBY method.
  • Example B-2 Action against Septoria tritici (causal fungus of Septoria tritici leaf blotch in wheat) a) Fungal growth assay
  • Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically after 4 days. The fungicide interactions in the combinations are calculated according to the COLBY method. The data generated in this experiment indicate synergy between penthiopyrad and cyprodinil when used in mixture with one another.
  • Example B-3 Action against Pseudocercosporella herpotrichoides var. herpotrichoides (also known as Tapesia yallundae; causal fungus of eyespot disease in cereals) - fungal growth assay
  • Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 C and the inhibition of growth is determined photometrically after 7 days. The fungicide interactions in the combinations are calculated according to the COLBY method. The data generated in this experiment indicate synergy between penthiopyrad and cyprodinil when used in mixture with one another.
  • compositions according to the invention exhibit good activity in all of the above examples.

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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)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition destinée à contrôler des maladies sur des plantes utiles ou sur des matières de propagation de celles-ci causées par des agents phytopathogènes, qui, en plus d'adjuvants de formulation inertes, comprend comme ingrédient actif un mélange d'un composant (A) et d'une quantité efficace de manière synergique d'un composant (B), le composant (A) étant le cyprodinile ; et le composant (B) étant le penthiopyrade.
PCT/EP2006/009404 2005-09-29 2006-09-27 Compositions fongicides WO2007039214A1 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
EP05021278.6 2005-09-29
EP05021278 2005-09-29
EP05025915 2005-11-28
EP05025915.9 2005-11-28
EP06009297.0 2006-05-05
EP06009297 2006-05-05
EP06792290A EP1947940A2 (fr) 2005-09-29 2006-09-27 Compositions fongicides

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2233000A3 (fr) * 2007-09-12 2012-12-12 Bayer CropScience AG Traitement après récolte
CN103155924A (zh) * 2011-12-18 2013-06-19 深圳诺普信农化股份有限公司 一种含有吡噻菌胺的杀菌组合物
US8642506B2 (en) 2006-11-21 2014-02-04 Mitsui Chemicals, Inc. Plant disease damage control composition and plant disease damage prevention and control method
CN103651485A (zh) * 2012-09-11 2014-03-26 陕西美邦农药有限公司 一种含吡噻菌胺的高效杀菌组合物
AU2013202483B2 (en) * 2007-09-12 2015-04-23 Bayer Cropscience Aktiengesellschaft Post-harvest treatment
US11246704B2 (en) 2017-08-03 2022-02-15 Cardiovalve Ltd. Prosthetic heart valve

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EP0642735A1 (fr) * 1993-09-13 1995-03-15 BASF Aktiengesellschaft Mélanges fongicides
JPH11302110A (ja) * 1998-04-24 1999-11-02 Mitsui Chem Inc 植物病害防除剤組成物
WO2006036827A1 (fr) * 2004-09-27 2006-04-06 E.I. Dupont De Nemours And Company Melanges fongicides de derive de thiophene
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GB2279568A (en) * 1993-07-02 1995-01-11 Ciba Geigy Ag Synergistic microbicide composition for plants
EP0642735A1 (fr) * 1993-09-13 1995-03-15 BASF Aktiengesellschaft Mélanges fongicides
JPH11302110A (ja) * 1998-04-24 1999-11-02 Mitsui Chem Inc 植物病害防除剤組成物
WO2006036827A1 (fr) * 2004-09-27 2006-04-06 E.I. Dupont De Nemours And Company Melanges fongicides de derive de thiophene
WO2006105888A2 (fr) * 2005-04-06 2006-10-12 Bayer Cropscience Ag Combinaisons d'agents actifs fongicides synergiques

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8642506B2 (en) 2006-11-21 2014-02-04 Mitsui Chemicals, Inc. Plant disease damage control composition and plant disease damage prevention and control method
EP2233000A3 (fr) * 2007-09-12 2012-12-12 Bayer CropScience AG Traitement après récolte
AU2013202483B2 (en) * 2007-09-12 2015-04-23 Bayer Cropscience Aktiengesellschaft Post-harvest treatment
CN103155924A (zh) * 2011-12-18 2013-06-19 深圳诺普信农化股份有限公司 一种含有吡噻菌胺的杀菌组合物
CN103651485A (zh) * 2012-09-11 2014-03-26 陕西美邦农药有限公司 一种含吡噻菌胺的高效杀菌组合物
US11246704B2 (en) 2017-08-03 2022-02-15 Cardiovalve Ltd. Prosthetic heart valve

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