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WO2007128428A2 - Compositions fongicides - Google Patents

Compositions fongicides Download PDF

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Publication number
WO2007128428A2
WO2007128428A2 PCT/EP2007/003693 EP2007003693W WO2007128428A2 WO 2007128428 A2 WO2007128428 A2 WO 2007128428A2 EP 2007003693 W EP2007003693 W EP 2007003693W WO 2007128428 A2 WO2007128428 A2 WO 2007128428A2
Authority
WO
WIPO (PCT)
Prior art keywords
component
useful plants
plants
phytopathogens
diseases
Prior art date
Application number
PCT/EP2007/003693
Other languages
English (en)
Other versions
WO2007128428A3 (fr
Inventor
Christoph Neumann
Colin Edward Mills
Ulrich Johannes Haas
Original Assignee
Syngenta Participations Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from EP06008895A external-priority patent/EP1856978A1/fr
Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Publication of WO2007128428A2 publication Critical patent/WO2007128428A2/fr
Publication of WO2007128428A3 publication Critical patent/WO2007128428A3/fr

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Classifications

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

Definitions

  • the present invention relates to 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.
  • Cyproconazole (2-(4-chiorophenyl)-3-cyclopropyl-1-(1 H-1 ,2,4-triazol-1-yl)butan-2-ol), is a steroid demethylation inhibitor (ergosterol biosynthesis inhibitor) and is used as a fungicide which is effective against a number of diseases caused by ascomycetes, basidiomycetes and deuteromycetes.
  • Penthiopyrad ( ⁇ /-[2-(1 ,3-dimethylbutyl)-3-thienyl]-1 -methyl-3-(trifluoromethyl)-1 H-pyrazole-4- carboxamide) is a fungicide which is effective against a number of diseases caused by ascomycetes, basidiomycetes and deuteromycetes. Mixtures of penthiopyrad with compounds, which act at the bc ⁇ complex of the fungal mitochondrial respiratory electron transfer site, are described in WO 2006/36827.
  • 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 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 cyproconazole; and component (B) is penthiopyrad; with the proviso that if further compounds are present, which act at the Oc 1 complex of the fungal mitochondrial respiratory electron transfer site, said compounds are selected from group consisiting of azoxystrobin, kresoxim-methyl, dimoxystrobin and metominostrobin.
  • the mixture of component (A) and component (B) 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.
  • This synergistic activity is apparent from the fact that the fungicidal activity of the composition comprising component (A) and component (B) is greater than the sum of the fungicidal activities of component (A) and of component (B).
  • This synergistic activity extends the range of action of component (A) and component (B) in two ways.
  • compositions according to the invention can also have further surprising advantageous properties.
  • advantageous properties are: more advantageuos degradability; improved toxicological and/or ecotoxicological behaviour; or improved characteristics of the useful 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.
  • Cyproconazole 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 (207) and (1962), respectively. http://www/ penthiopyrad and cyproconazole can exist in different stereoisomeric forms.
  • the invention covers mixtures comprising all those stereoisomeric forms or mixtures of those stereoisomeric forms in any ratio.
  • composition stands for the various mixtures or combinations of component (A) and component (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 component (A) and component (B) is not essential for working the present invention.
  • the compositions according to the invention may comprise one or more additional active ingredient, such as a fungicide, insecticide, herbicide or growth regulator.
  • compositions according to the invention comprise, besides cyproconazole and penthiopyrad, a further active ingredient and said active ingredient acts at the Oc 1 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 bc ⁇ complex is sometimes referred to by other names in the biochemical literature, including complex III of the electron transfer chain and ubihydroquinonexytochrome c oxidoreductase.
  • the Oc 1 complex is described in, for example, J. Biol. Chem. 1989, 264, 14543-4-8; Methods Enzymol. 1986, 126, 253-71 ; and references cited therein.
  • 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
  • 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 cyproconazole; 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 cyproconazole; and component (B) is penthiopyrad.
  • 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); basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); fungi imperfecti (also known as deuteromycetes; e.g. Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Altemaria, Pyricularia and Pseudocercosporella).
  • ascomycetes e.g. Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula
  • basidiomycetes e.g. the genus Hemilei
  • 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 tolerant 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) inhibitors
  • 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® , Herculex I® 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.
  • VIP vegetative insecticidal proteins
  • 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 involved 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 so-called
  • 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.
  • compositions according to the invention are particularly useful for controlling the following plant diseases on useful plants: Alternaria species in fruit and vegetables; Ascochyta species in pulse crops; Botrytis cinerea in strawberries, tomatoes, sunflower, pulse crops, vegetables and grapes, such as Botrytis cinerea on grape; Cercospora arachidicola in peanuts; Cochliobolus sativus in cereals; Colletotrichum species in pulse crops; Erysiphe species in cereals; such as Erysiphe graminis on wheat and Erysiphe graminis on barley; Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits; Fusarium species in cereals and maize; Gaumannomyces graminis in cereals and lawns; Helminthosporium species in maize, rice and potatoes; Hemileia vastatrix on coffee; Microdochium species in wheat and rye; Mycosphaerella fijiensis in banana;
  • 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 or soil; the type of treatment, such as, for example spraying or dusting; the purpose of the treatment, such as, for example prophylactic or therapeutic; the type of fungi to be controlled or the application time.
  • 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 component (A) to component (B) is so selected as to give a synergistic activity.
  • the weight ratio of component (A) to component (B) is from 50 : 1 to 1 : 50, preferably from 10 : 1 to 1 : 10, more preferably from 5 : 1 to 1 : 5.
  • the synergistic activity of the compositions according to the invention is apparent from the fact that the fungicidal activity of the composition of component (A) and component (B) is greater than the sum of the fungicidal activities of component (A) and component (B).
  • the method of the invention comprises applying to the useful plants or the locus 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 or soil fungicides. With the 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 applied by treating the fungi, the useful plants or the locus thereof with a composition according to the invention.
  • compositions according to the invention may be applied before or after infection of the useful plants by the fungi.
  • component (A) When applied to the useful plants component (A) is applied 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.i./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 50 to 500 g of total composition per hectare.
  • composition of the invention may be employed in any conventional form, for example in the form of a twin pack, 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), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.
  • EC emulsion concentrate
  • SC suspension concentrate
  • SE suspo-emulsion
  • CS capsule suspension
  • WG water dispersible
  • 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.
  • 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), 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 Cyproconazole (component A) and Penthiopyrad (component B) in a specific mixing ratio.
  • Kaolin 62 % 27 % 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.
  • Emulsifiable concentrate active ingredient (A): B) 1 :5) 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.
  • Active ingredient [A) : B) 1 :5(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.
  • Active ingredient (A) : B) 2: 1 ) 15 % sodium lignosulfonate 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 :5) 8 % polyethylene glycol (mol. wt. 200) 3 % Kaolin 89 %
  • 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 :5) 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. Using such dilutions, living plants can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • 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; preferred 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 Erysiphe graminis, Pseudocercosporella herpotrichoides, Puccinia recondita, Puccinia striiformis, Pyrenophora tritici-repentis and Septoria tritici.
  • the disease is selected from Erysiphe graminis, Pseudocercosporella herpotrichoides, Puccinia recondita, Puccinia striiformis, Pyrenophora tritici-repentis and Septoria tritici.
  • 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.
  • Puccinia recondita on wheat plants, which comprises applying to the wheat plants or to the locus thereof a composition according to the
  • 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 Erysiphe graminis, Puccinia recondita, Pyrenophora teres, Ramularia collo-cygni and Rhynchosporium secalis; preferred is a method, wherein the disease is Puccinia recondita.
  • a synergistic effect exists whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components.
  • the action actually observed (O) is greater than the expected action (E)
  • the action of the combination is super-additive, i.e. there is a synergistic effect.
  • the synergism factor SF corresponds to O/E.
  • Example B-1 Action against Colletotrichum orbiculare (Glomerella laqenarium) on cucurbits 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 measured photometrically after 3 days.
  • DMSO DMSO
  • Example B-2 Action against Sclerotinia sclerotiorum (cottony rot) Mycelial fragments of the fungus, prepared from a fresh liquid culture, 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 48 hrs.
  • DMSO DMSO
  • Example B-3 Action against Venturia inaequalis (scab of apple) 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 measured photometrically after 11 days.
  • DMSO DMSO

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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 lutter contre des maladies sur des plantes utiles, ces maladies étant causées par des agents phytopathogènes. Outre des adjuvants de préparations inertes, cette composition comprend, comme ingrédients actifs, un constituant (A) et une dose synergiquement efficace d'un constituant (B), le constituant (A) étant le cyproconazole et le constituant (B) étant le penthiopyrad, à condition que des composés supplémentaires soient présents, ces composés agissant comme le complexe bc1 du site de transport des électrons respiratoires mitochondriaux fongiques, lesdits composés étant choisis dans le groupe constitué par l'azoxystrobine, le krésoxim-méthyle, la dimoxystrobine et la métominostrobine.
PCT/EP2007/003693 2006-04-28 2007-04-26 Compositions fongicides WO2007128428A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP06008895A EP1856978A1 (fr) 2006-04-28 2006-04-28 Compositions fongicides à base de Penthiopyrad et Cyproconazole
EP06008895.2 2006-04-28
EP06018727 2006-09-07
EP06018727.5 2006-09-07

Publications (2)

Publication Number Publication Date
WO2007128428A2 true WO2007128428A2 (fr) 2007-11-15
WO2007128428A3 WO2007128428A3 (fr) 2008-01-03

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Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5747518A (en) * 1995-04-11 1998-05-05 Mitsui Toatsu Chemicals, Inc. Substituted thiophene derivative and agricultural and horticultural fungicide containing the same as active ingredient
JP4090639B2 (ja) * 1999-09-03 2008-05-28 三井化学株式会社 植物病害防除剤組成物
DK1796465T3 (da) * 2004-09-27 2008-12-15 Du Pont Svampedræbende blandinger af thiophenderivat
EP2452562A3 (fr) * 2005-02-04 2012-10-24 Mitsui Chemicals Agro, Inc. Composition de prévention des maladies de plantes et procédé de prévention des maladies

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