WO2007045455A1 - Compositions fongicides - Google Patents

Compositions fongicides Download PDF

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Publication number
WO2007045455A1
WO2007045455A1 PCT/EP2006/010047 EP2006010047W WO2007045455A1 WO 2007045455 A1 WO2007045455 A1 WO 2007045455A1 EP 2006010047 W EP2006010047 W EP 2006010047W WO 2007045455 A1 WO2007045455 A1 WO 2007045455A1
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WIPO (PCT)
Prior art keywords
component
salt
metal complex
composition according
plants
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PCT/EP2006/010047
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English (en)
Inventor
Jeremy Godwin
Eric Guicherit
Christoph Neumann
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Syngenta Participations Ag
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Priority claimed from EP05022880A external-priority patent/EP1776864A1/fr
Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Publication of WO2007045455A1 publication Critical patent/WO2007045455A1/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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles

Definitions

  • the present invention relates to novel fungicidal compositions capable of controlling phyto- pathogenic fungi on plants and to a method of controlling such fungi on plants.
  • Chlorothalonil (2,4,5,6-tetrachloro-1 ,3-benzenedicarbonitrile) is a fungicide which is effective against a number of diseases caused by Ascomycetes sp. and Deuteromycetes sp..
  • Triazole fungicides including Propiconazole (1-[[2-(2,4-dichlorophenyl)-4-propyl-1 ,3- dioxolan-2-yl]methyl]-1H-1 ,2,4-triazole), Epoxiconazole (cis-1-[[3-(2-chlorophenyl)-2-(4- fluorophenyl)oxiranyl]methyl]-1 H-1 ,2,4-triazole), Prothioconazole (2-[2-(1 -chlorocyclopropyl)- 3-(2-chlorophenyl)-2-hydroxypropyl]-1 ,2-dihydro-3H-1 ,2,4-triazole-3-thione), Tebuconazole ( ⁇ -[2-(4-chlorophenyl)ethyl]-a-(1 ,1-dimethylethyl)-1 H-1 ,2,4-triazole-1-ethanol) and Metconazole (5-[(4-chloroph
  • Certain mixtures of two of said fungicides are known, such as, for example, mixtures of Chlorothalonil and Propiconazole and mixtures of Chlorothalonil and Epoxiconazole, .
  • Chlorothalonil and Tebuconazole which are both known from US-6, 319,949; mixtures of Chlorothalonil and Prothioconazole, which are known from AU-727-186; and mixtures of Propiconazole and Epoxiconazole and mixtures of Propiconazole and Metconazole, which are known from US-6,455,563.
  • Chlorothalonil and Metconazole are known from EP-0-951-831 and mixtures of Epoxiconazole and Metconazole are known from WO96/01054. Mixtures of Chlorothalonil and Tebuconazole are known from EP-0-951-831.
  • Crop tolerance and activity against phytopathogenic plant fungi of both fungicides does not always satisfy the needs of agricultural practice in many respects.
  • a composition capable of controlling phytopathogenic fungi on a plant or propagation material thereof said composition comprising as active ingredient a mixture of component (A), component (B) and component (C); wherein component (A), component (B) and component (C) are present in the composition in amounts producing a synergistic effect; and wherein component (A) is Chlorothalonil; component (B) is selected from the group consisting of: Propiconazole; Epoxiconazole; Prothioconazole; Tebuconazole; and Metconazole or in each case a salt or metal complex thereof; and component (C) is a triazole fungicide selected from Fluquinconazole and a compound of formula A-1
  • L is a chemical bond, -CH 2 -, -CH 2 -CH 2 - Or -CHR 3 -CH 2 -;
  • R 1 is hydrogen, hydroxy or cyano
  • R 2 is phenyl, tert.-butyl, -CH 2 -O-CF 2 -CHF 2 or 1-chlorocyclopropyl; or R 1 together with R 2 is -0-CHR 4 -CH 2 -O- or -0-CHR 5 -; or R 3 together with R 2 is -CH 2 -CH 2 -CR 6 R 7 -;
  • R 4 is methyl
  • R 5 is 2-chlorphenyl
  • R 6 is isopropyl or methyl
  • R 7 is hydrogen or methyl
  • R 8 is hydrogen or chlor
  • R 9 is hydrogen, chlor, fluor or 4-chlorophenoxy; or a salt or metal complex of component (C), and wherein component (B) and component (C) are different.
  • component (B) is Propiconazole a salt or metal complex thereof and wherein component (C) is not Propiconazole.
  • component (B) is Epoxiconazole a salt or metal complex thereof and wherein component (C) is not Epoxiconazole.
  • component (B) is Prothioconazole a salt or metal complex thereof and wherein component (C) is not Prothioconazole.
  • component (B) is Tebuconazole a salt or metal complex thereof and wherein component (C) is not Tebuconazole.
  • component (B) is Metconazole or a salt or metal complex thereof and wherein component (C) is not Metconazole.
  • component (A); component (B) and component (C) not only brings about the enhancement of the spectrum of action with respect to the phytopathogen to be controlled but achieves a synergistic effect which extends the range of action of component (A), component (B) and component (C) in two ways. Firstly, the rates of application of component (A), component (B) and component (C) are lowered whilst the action remains equally good. Secondly, the active ingredient mixture still achieves a high degree of phytopathogen control even where the three 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 are: a broadening of the spectrum of fungicidal activity to other phytopathogens, for example to resistant strains; a reduction in the rate of application of the active ingredients; more advantageuos degradability; improved toxicological and/or ecotoxicological behaviour; or improved characteristics of the plants including: emergence, 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, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigor, and early germination.
  • tert.-butyl means the group -C(CH 3 ) 3 and the term
  • isopropyl means the group -CH(CH 3 ) 2 .
  • R 3 together with R 2 is -CH 2 -CH 2 -CR 6 R 7 - the carbon atom substituted by R 6 and R 7 is directly adjacent to the carbon atom substituted by
  • R 4 is methyl
  • R 8 is chlor
  • R 9 is 4-chlorophenoxy
  • R 5 is 2-chlorphenyl
  • R 8 is hydrogen
  • R 9 is fluor
  • R 8 is hydrogen
  • R 9 is chlor is known by the name Fenbuconazole.
  • R 8 is chlor
  • R 9 is hydrogen
  • Prothioconazole The compound of formula A-1 , wherein Q is Q1 , L is -CH 2 -CH 2 -, Ri is hydroxy, R 2 is tert. -butyl, R 8 is hydrogen, R 9 is chlor is known by the name Tebuconazole.
  • Difenoconazole, Fenbuconazole, Fluquinconazole, Ipconazole, and Tetraconazole are also described in "The Pesticide Manual”. Difenoconazole is described therein under entry number (247), Fenbuconazole under (329), Fluquinconazole under (385), Ipconazole under (468) and Tetraconazole under (778).
  • the triazole fungicide of components (B) and (C) can exist in different stereoisomeric forms.
  • the invention covers mixtures comprising all those stereoisomeric forms or mixtures of those stereoisomeric forms in any ratio.
  • the triazole fungicide of components (B) and (C) can be used in their free form or as a salt or metal complex thereof.
  • the mentioned salt of the triazole fungicide of component (B) and (C) can be prepared by reacting the respective free form of the triazole fungicide with an acid.
  • hydrohalic acids such 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 such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid
  • sulfuric acid, phosphoric acid, nitric 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.
  • a particular embodiment of the present invention is represented by those mixtures which comprise as component (C) a compound of formula A-1 or a salt or metal complex thereof.
  • a further embodiment of the present invention is represented by those mixtures which comprise as component (C) a compound of formula A-1 , wherein Q is Q1 ; or a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) a compound of formula A-1 , wherein Q is Q2; or a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) a compound of formula A-1 , wherein Q is
  • L is a chemical bond, -CH 2 -, -CH 2 -CH 2 - or -CHR 3 -CH 2 -;
  • R 1 is hydroxy
  • R 2 is tert.-butyl or 1-chlorocyclopropyl, or R 1 together with R 2 is -0-CHR 5 -; or R 3 together with R 2 is -CH 2 -CH 2 -CR 6 R 7 -;
  • R 5 is 2-chlorphenyl
  • R 6 is methyl or isopropyl
  • R 7 is hydrogen or methyl
  • R 8 is hydrogen or chlor
  • R 9 is hydrogen, chlor or fluor; or a salt or metal complex thereof.
  • a particular embodiment of the present invention is represented by those mixtures which comprise as component (C) a triazole fungicide selected from Difenoconazole, Epoxiconazole, Fenbuconazole, Fluquinconazole, Ipconazole, Metconazole, Prothioconazole, Tebuconazole and Tetraconazole; or in each case a salt or metal complex thereof.
  • a further embodiment of the present invention is represented by those mixtures which comprise as component (C) a triazole fungicide selected from Epoxiconazole, Ipconazole, Metconazole, Prothioconazole and Tebuconazole; or in each case a salt or metal complex thereof.
  • component (C) a triazole fungicide selected from Epoxiconazole, Ipconazole, Metconazole, Prothioconazole and Tebuconazole; or in each case a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) a triazole fungicide selected from Epoxiconazole, Ipconazole and Prothioconazole; or in each case a salt or metal complex thereof.
  • component (C) a triazole fungicide selected from Epoxiconazole, Ipconazole and Prothioconazole; or in each case a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) Epoxiconazole; or a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) Ipconazole; or a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) Metconazole; or a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) Prothioconazole; or a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) Tebuconazole; or a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) a compound of formula A-1 , wherein Q is
  • Q1 L is a chemical bond, -CH 2 -CH 2 - Or -CHR 3 -CH 2 -;
  • R 1 is hydrogen, hydroxy or cyano;
  • R 2 is phenyl, -CH 2 -O-CF 2 -CHF 2 ; or R 1 together with R 2 is -0-CHR 4 -CH 2 -O-; or R 3 together with R 2 is -CH 2 -CH 2 -CR 6 R 7 -;
  • R 4 is methyl
  • R 6 is isopropyl
  • R 7 is hydrogen
  • R 8 is hydrogen or chlor
  • R 9 is chlor or 4-chlorophenoxy; or in each case a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) a triazole fungicide selected from Difenoconazole,
  • Fenbuconazole Ipconazole and Tetraconazole; or in each case a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) Difenoconazole; or a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) Fenbuconazole; or a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) Tetraconazole; or a salt or metal complex thereof.
  • a still further embodiment of the present invention is represented by those mixtures which comprise as component (C) Fluquinconazole; or a salt or metal complex thereof.
  • the compound of component (B) is in the free form.
  • the triazole fungicide of component (C) is used in the free form.
  • the compound representing component (B) is different to the compound representing component (C).
  • composition stands for the various mixtures or combinations of component (A), component (B) and component (C), 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.
  • component (A), component (B) and component (C) is not essential for working the present invention.
  • compositions according to the invention may also comprise additional pesticides.
  • compositions according to the invention are effective against harmful microorganisms, such as microorganisms, that cause disease in plants, 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); Basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); Fungi imperfecti (also known as De ⁇ teromycetes; e.g.
  • Botrytis Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyhcularia and Pseudocercosporella); Oomycetes (e.g. Phytophthora, Peronospora, Pse ⁇ doperonospora, Albugo, Bremia, Pythium, Pseudosclerospora, Plasmopara).
  • plant'V'plants includes plants of the following species: 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;
  • plant'V'plants also includes genetically modified plants including those plants which have been rendered resistant to herbicides, insecticides, fungicides or have been modified in some other way such as to enhance yield, drought tolerance or quality. Such genetically modified plants may have been modified via recombinant nucleic acid techniques well know to the person skilled in the art.
  • 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 means seeds.
  • compositions according to the invention are particularly effective against powdery mildews; rusts; leafspot species; early blights and molds; especially against Septoria, Puccinia, Erysiphe, Pyrenophora, Fusarium and/or Tapesia in cereals; Phakopsora in soybeans; Hemileia in coffee; Phragmidium in roses; Alternaria 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; Monilinia spp. in fruits.
  • compositions according to the invention are particularly useful for controlling the following plant diseases:
  • Rhizoctonia species in cotton, soybean, cereals, maize, potatoes, rice and lawns are Rhizoctonia species in cotton, soybean, cereals, maize, potatoes, rice and lawns.
  • compositions 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.
  • the present invention still further provides a composition as described above wherein the weight ratio of component (A) to component (B), the weight ratio of component (A) to component (C) and the weight ratio of component (B) to component (C) is from 1000 : 1 to 1 : 1000.
  • component (B) and component (C) 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 ratios of component (A) to component (B), of component (A) to component (C), and of component (B) to component (C) are selected in a way to give a synergistic activity.
  • the weight ratio of component (A) to component (B), the weight ratio of component (A) to component (C), and the weight ratio of component (B) to component (C) is from 1000 : 1 to 1 : 1000.
  • Chlorothalonil : Propiconazole : Epoxiconazole is 10:1 :1.
  • the weight ratio of Chlorothalonil : Propiconazole (A:B) is 10:1
  • the weight ratio of Chlorothalonil : Epoxiconazole (A:C) is 10:1
  • the weight ratio of Propiconazole: Epoxiconazole (B:C) is 1:1.
  • the weight ratio of component (A) to component (B), the weight ratio of component (A) to component (C), and the weight ratio of component (B) to component (C) is from 100 : 1 to 1 : 100.
  • the weight ratio of component (A) to component (B), the weight ratio of component (A) to component (C), and the weight ratio of component (B) to component (C) is from 20 : 1 to 1 : 20.
  • the weight ratio of component (A) to component (B), the weight ratio of component (A) to component (C), and the weight ratio of component (B) to component (C) is from 10 : 1 to 1 : 10.
  • the synergistic activity of the compositions according to the invention is apparent from the fact that the fungicidal activity of the composition comprising component (A), component (B) and component (C) is greater than the sum of the fungicidal activities of component (A), component (B) and component (C).
  • a method of controlling phytopathogenic fungi on a plant or propagation material thereof which comprises applying to said plant or said propagation material thereof a composition as described above.
  • the present invention still further provides a method as described above wherein said plant is a cereal plant.
  • 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), 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 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.
  • 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.
  • compositions according to the invention are applied by treating the fungi, the plants, 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 plants or the propagation material thereof by the fungi.
  • component (A) When applied to the plants component (A) is applied at a rate of 5 to 4000 g a.i./ha, particularly 10 to 2000 g a.i./ha, e.g. 100, 200, 500, 750, 1000 or 1500 g a.i./ha, in association with 1 to 2000 g a.i./ha, particularly 5 to 1000 g a.i./ha, e.g. 50, 75, 100, 150 or 200 g a.i./ha of component (B) and in association with 1 to 2000 g a.i./ha, particularly 5 to 1000 g a.i./ha, e.g. 50, 75, 100, 150 or 200 g a.i./ha of component (C).
  • component (C) When applied to the plants component (A) is applied at a rate of 5 to 4000 g a.i./ha, particularly 10 to 2000 g a.i./ha, e.g. 100, 200, 500,
  • the application rates of the compositions according to the invention depend on the type of effect desired, and typically range from 7 to 8000 g of total composition per hectare, more specifically from 20 to 4000 g ot total composition per hectare.
  • compositions according to the invention are used for treating seed, rates of 0.001 to 50 g of component (A) per kg of seed, more specifically from 0.01 to 10g per kg of seed, and 0.001 to 50 g of component (B), per kg of seed, more specifically from 0.01 to 10g per kg of seed, and 0.001 to 50 g of component (C), per kg of seed, more specifically 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/triple 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
  • 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.
  • 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 formulation form, e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • suitable seed dressing formulation 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 component (A) together with component (B) together with component (C), 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.
  • compositions as described above in the prevention and/or treatment of growth and/or infestation of a phytopathogenic fungi on a plant.
  • the method of application such as spraying, atomising, dusting, scattering, coating or pouring can be chosen in accordance with the prevailing circumstances.
  • the composition may also be added to the place that the plants are growing such as the soil in which the plants are growing.
  • compositions as described above for the protection of industrial materials.
  • said industrial materials are selected from the group consisting of: wood; plastic; wood plastic composite; paint; paper; and wallboards.
  • Industrial material means those materials used for construction and the like.
  • industrial material includes structural timber, doors, cupboards, storage units, carpets, particularly natural fibre carpets such as wool and hessian, paints, plastics, wood (including engineered wood) and wood plastic composite.
  • industrial material includes adhesives, sealants, joining materials and joints and insulation material.
  • "industrial material” means structural timber.
  • “industrial material” means engineered wood.
  • “industrial material” means plastic.
  • Plastics includes plastic polymers and copolymers, including: acrylonitrile butadiene styrene, butyl rubber, epoxies, fluoropolymers, isoprene, nylons, polyethylene, polyurethane, polypropylene, polyvinyl chloride, polystyrene, polycarbonate, polyvinylidene fluoride, polyacrylate, polymethyl methacrylate, polyurethane, polybutylene, polybutylene terephthalate, polyether sulfone, polyphenyllenoxide, polyphenylene ether, polyphenylene sulfide, polyphtatamide, polysulphene, polyester, silicone, styrene butadiene rubber and combinations of polymers.
  • plastic polymers and copolymers including: acrylonitrile butadiene styrene, butyl rubber, epoxies, fluoropolymers, isoprene, nylons, poly
  • “industrial material” means polyvinyl chloride (PVC). In a further embodiment “industrial material” means polyurethane (PU). In a further embodiment “industrial material” means paint. In a further embodiment “industrial material” means wood plastic composite (WPC). Wood plastic composite is a material that is well known in the art. A review of WPCs can be found in the following publication - Craig Clemons - Forrest Products Journal. June 2002 VoI 52. No. 6. pp 10-18.
  • Wood is to be understood as meaning wood and wood products, for example: derived timber products, lumber, plywood, chipboard, flakeboard, laminated beams, oriented strandboard, hardboard, and particleboard, tropical wood, structural timber, wooden beams, railway sleepers, components of bridges, jetties, vehicles made of wood, boxes, pallets, containers, telegraph-poles, wooden fences, wooden lagging, windows and doors made of wood, plywood, chipboard, joinery, or wooden products which are used, quite generally, for building houses or decks, in building joinery or wood products that are generally used in house-building including engineered wood, construction and carpentry.
  • "Industrial material” also includes cooling lubricants and cooling and heating systems, ventilation and air conditioning systems and parts of production plants, for example cooling- water circuits.
  • the methods of the invention can be used in the prevention and/or treatment of the growth/infestation by/of a fungus as described within this specification.
  • the fungus can be controlled by treating the fungus or the industrial material with a composition according to the invention in a convenient manner.
  • Examples of ways in which the fungus or industrial material can be treated with a fungicide according to the invention are: by including said fungicide in the industrial material itself, absorbing, impregnating, treating (in closed pressure or vacuum systems) said material with said fungicide, dipping or soaking the industrial material, or coating the industrial material for example by curtain coating, roller, brush, spray, atomisation, dusting, scattering or pouring application.
  • Industrial materials comprising a composition as described above.
  • said Industrial materials are selected from the group consisting of: wood; plastic; wood plastic composite; paint; paper; and wallboards.
  • said materials are wood.
  • active ingredient denotes a mixture of Chlorothalonil (component A), Propiconazole or Epoxiconazole or Prothioconazole or Tebuconazole or Metconazole or in each case a salt or metal complex thereof (component B) and a triazole fungicide of component (C) (component C) wherein component (B) and component (C) are different, 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) :C) 1 :6:6) 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) :C) 1 :6:6(a), 1 :2:2(b), 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) :C) 2:1 :1 ) 15 %
  • 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) :C) 1 :10:10) 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) :C) 1 :8:8) 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %
  • Silicone oil (in the form of a 75 % emulsion in water) 1 %
  • 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. Using such dilutions, 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) :C) 1 :8:8) 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.
  • the resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
  • COLBY (additive action or action to be expected).
  • X % action by active ingredient A) using p ppm of active ingredient.
  • X AB % action by a mixture (A+B), for example, using p ppm of active ingredient.
  • synergism corresponds to a positive value for the difference of (O-E).
  • expected activity said difference (O-E) is zero.
  • a negative value of said difference (O-E) signals a loss of activity compared to the expected activity.
  • Example B-1 Action against Botrvtis cinerea on grapes a) Fungal growth assay
  • Example B-2 Action against Septoria tritici on wheat a) Fungal growth assay
  • Conidia of the fungus from cryogenic storage were 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 was added.
  • nutrient broth PDB potato dextrose broth
  • test plates were incubated at 24 0 C and the inhibition of growth was determined photometrically after 72 hrs.
  • the fungicide interactions in the combinations are calculated according to COLBY method.
  • Example B-3 Action against Pyricularia oryzae on rice a) Fungal growth assay
  • Rice leaf segments are placed on agar in multiwell 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-4 Action against Alternaria solani (early blight) a) Fungal growth assay
  • Example B-5 Action against Pyrenophora teres (Net blotch) a) Fungal growth assay
  • Barley leaf segments are placed on agar in multiwell 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-6 Action against Venturia inaegualis on apple a) Fungal growth assay
  • Example B-7 Action against Pvthium ultimum (Damping off) - fungal growth assay
  • Mycelial fragments of the fungus prepared from a fresh liquid culture, were directly mixed into nutrient broth (PDB potato dextrose broth).
  • a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added.
  • the test plates were incubated at 24°C and the inhibition of growth was determined photometrically after 48 hrs.
  • the fungicide interactions in the combinations are calculated according to COLBY method.
  • Example B-8 Action against Leptosphaeria nodorum (glume blotch) - fungal growth assay
  • Conidia of the fungus from cryogenic storage were 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 was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically after 48 hrs. The fungicide interactions in the combinations are calculated according to COLBY method.
  • Example B-9 Action against Pseudocercosporella herpotrichoides var. acuformis (eyespot/cereals) - fungal growth assay
  • Conidia of the fungus from cryogenic storage were 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 was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically after 72 hrs. The fungicide interactions in the combinations are calculated according to COLBY method.
  • Example B-10 Action against Ustilago maydis (corn smut) - fungal growth assay
  • Conidia of the fungus from cryogenic storage were 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 was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically after 48 hrs. The fungicide interactions in the combinations are calculated according to COLBY method.
  • Example B-11 Action against Phytophthora infestans (late blight) on tomato - protective treatment
  • Tomato leaf disks are placed on water agar in multiwell 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-12 Action against Plasmopara viticola (downy mildew) on grape vines - protective treatment
  • Grape vine leaf disks are placed on agar in multiwell 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 7 days after inoculation as preventive fungicidal activity.
  • the fungicide interactions in the combinations are calculated according to COLBY method.
  • Example B-13 Action against Botrytis cinerea (Grey mould) on beans - protective treatment
  • Bean leaf disks are placed on agar in multiwell 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-14 Action against Erysiphe graminis f.sp. hordei (Barley powdery mildew) on barley - protective treatment
  • Barley leaf segments are placed on agar in multiwell 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-15 Action against Ervsiphe graminis f.sp. tritici (Wheat powdery mildew) on barley - protective treatment Barley leaf segments are placed on agar in multiwell 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-16 Action against Puccinia recondita (Brown rust) on wheat a) Protective Treatment of leaf segments
  • Example B-17 Action against Septoria nodorum on wheat a) Protective Treatment of leaf segments
  • Example B-18 Action against Podosphaera leucotricha (Powdery mildew) on apple - protective treatment
  • Example B-19 Action against Ervsiphe qraminis (Powdery mildew) on barley - protective treatment
  • Example B-20 Action against Botrytis cinerea on tomatoes - protective treatment 4 week old tomato plants cv. Roter Gnom are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. Two days after application, the tomato plants are inoculated by spraying a spore suspension (1x10 5 conidia/ml) on the test plants. After an incubation period of 4 days at 2O 0 C and 95% relative humidity in a growth chamber the disease incidence is assessed. The fungicide interactions in the combinations are calculated according to COLBY method.
  • Example B-21 Action against Helminthosporium teres (Net blotch) on barley - protective treatment
  • Example B-22 Action against Uncinula necator (Powdery mildew) on grapes - protective treatment

Abstract

L'invention concerne une composition capable de supprimer les champignons phytopathogènes sur une plante ou sur un matériel de propagation de cette dernière, ladite composition comprenant comme ingrédient actif un mélange d'un composant (A), d'un composant (B) et d'un composant (C); le composant (A), le composant (B) et le composant (C) étant présents dans la composition dans des quantités exerçant un effet de synergie; et le composant (A) étant du chlorothalonil; le composant (B) étant choisi dans le groupe composé du propiconazole; de l'époxiconazole; du prothioconazole; du tébuconazole; et du metconazole ou, dans chaque cas, d'un sel ou d'un complexe métallique de ces derniers; et le composant (C) étant un fongicide triazole tel que décrit dans les revendications, les composants (B) et (C) étant différents. La composition de l'invention convient également à la protection d'équipement industriels.
PCT/EP2006/010047 2005-10-20 2006-10-18 Compositions fongicides WO2007045455A1 (fr)

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EP05022953 2005-10-20
EP05022955 2005-10-20
EP05022954 2005-10-20
EP05022880.8 2005-10-20
EP05022880A EP1776864A1 (fr) 2005-10-20 2005-10-20 Compositions fongicides
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WO2007062802A2 (fr) * 2005-11-29 2007-06-07 Syngenta Participations Ag Compositions fongicides
WO2008071915A2 (fr) * 2006-12-15 2008-06-19 Syngenta Limited Préparations
WO2009071389A1 (fr) * 2007-12-05 2009-06-11 Basf Se Mélanges fongicides
WO2009071419A1 (fr) * 2007-12-04 2009-06-11 Basf Se Mélanges fongicides
WO2009071450A1 (fr) * 2007-12-05 2009-06-11 Basf Se Mélanges fongicides
EP3114934A1 (fr) * 2015-07-07 2017-01-11 Spiess-Urania Chemicals GmbH Fongicide pour cereales et procede d'application sur une plante
WO2019186359A1 (fr) * 2018-03-26 2019-10-03 Upl Ltd Associations fongicides

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Cited By (11)

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Publication number Priority date Publication date Assignee Title
WO2007062802A2 (fr) * 2005-11-29 2007-06-07 Syngenta Participations Ag Compositions fongicides
WO2007062802A3 (fr) * 2005-11-29 2007-09-07 Syngenta Participations Ag Compositions fongicides
WO2008071915A2 (fr) * 2006-12-15 2008-06-19 Syngenta Limited Préparations
WO2008071915A3 (fr) * 2006-12-15 2008-11-06 Syngenta Ltd Préparations
EA020011B1 (ru) * 2006-12-15 2014-08-29 Синджента Лимитед Состав
WO2009071419A1 (fr) * 2007-12-04 2009-06-11 Basf Se Mélanges fongicides
WO2009071389A1 (fr) * 2007-12-05 2009-06-11 Basf Se Mélanges fongicides
WO2009071450A1 (fr) * 2007-12-05 2009-06-11 Basf Se Mélanges fongicides
EP3114934A1 (fr) * 2015-07-07 2017-01-11 Spiess-Urania Chemicals GmbH Fongicide pour cereales et procede d'application sur une plante
WO2019186359A1 (fr) * 2018-03-26 2019-10-03 Upl Ltd Associations fongicides
CN111988995A (zh) * 2018-03-26 2020-11-24 Upl有限公司 杀真菌组合

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