WO2011135838A1 - Plant disease control composition and its use - Google Patents

Plant disease control composition and its use Download PDF

Info

Publication number
WO2011135838A1
WO2011135838A1 PCT/JP2011/002421 JP2011002421W WO2011135838A1 WO 2011135838 A1 WO2011135838 A1 WO 2011135838A1 JP 2011002421 W JP2011002421 W JP 2011002421W WO 2011135838 A1 WO2011135838 A1 WO 2011135838A1
Authority
WO
WIPO (PCT)
Prior art keywords
chlorothalonil
carboxamide compound
diseases
composition
plant disease
Prior art date
Application number
PCT/JP2011/002421
Other languages
French (fr)
Inventor
Yuichi Matsuzaki
Original Assignee
Sumitomo Chemical Company, Limited
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
Application filed by Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Priority to US13/643,818 priority Critical patent/US8969399B2/en
Priority to KR1020127028103A priority patent/KR101812360B1/en
Priority to BR112012027382-5A priority patent/BR112012027382B1/en
Priority to MX2012012306A priority patent/MX2012012306A/en
Priority to CN2011800208409A priority patent/CN102858165A/en
Priority to CA2797382A priority patent/CA2797382C/en
Publication of WO2011135838A1 publication Critical patent/WO2011135838A1/en

Links

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
    • A01N43/48—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
    • 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
    • A01N37/18—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 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • 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
    • 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
    • A01N43/92—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more halogen atoms as ring hetero atoms

Definitions

  • the present invention relates to a plant disease control composition and its use.
  • An object of the present invention is to provide a composition having an excellent effect for controlling plant disease.
  • a plant disease control composition comprising a carboxamide compound represented by formula (I): wherein R 1 represents a hydrogen atom or a methyl group, and R 2 represents a methyl group, a difluoromethyl group or a trifluoromethyl group, and chlorothalonil.
  • a method of controlling plant disease which comprises a step of treating a plant or the soil where a plan grows with an effective amount of a carboxamide compound represented by formula (I): wherein R 1 represents a hydrogen atom or a methyl group, and R 2 represents a methyl group, a difluoromethyl group or a trifluoromethyl group, and chlorothalonil.
  • various plant diseases can be controlled.
  • composition comprises a carboxamide compound represented by formula (I): wherein R 1 and R 2 represent the same meanings as defined in the above (hereinafter referred to as “carboxamide compound”), and chlorothalonil.
  • the "carboxamide compound” are those as described in, for example, WO86/02641 or WO92/12970 and can be prepared by the method described therein.
  • carboxamide compound represented by formula (1) (hereinafter referred to as “carboxamide compound (1) "); carboxamide compound represented by formula (2): (hereinafter referred to as “carboxamide compound (2)”); carboxamide compound represented by formula (3): (hereinafter referred to as “carboxamide compound (3)”): carboxamide compound represented by formula (4): (hereinafter referred to as “carboxamide compound (4)”); carboxamide compound represented by formula (5): (hereinafter referred to as "carboxamide compound (5)”).
  • Chlorothalonil is a known compound and described in, for example, "THE PESTICIDE MANUAL - 14 th EDITION (published by BCPC) ISBN 1901396142. This compound can be obtained from the product containing said compound in the market or can be synthesized by publicly known method.
  • the weight ratio of the "carboxamide compound” to chlorothalonil in the “composition” is usually from 0.001/1 to 500/1, and preferably from 0.01/1 to 1/1.
  • the “composition” may be a mixture itself of a “carboxamide compound” and chlorothalonil
  • the “composition” is usually prepared by mixing a “carboxamide compound", chlorothalonil and an inert carrier, and if necessary, by adding a surfactant and/or another auxiliary for formulation and by formulating the mixture into oil formulation, emulsifiable concentrate, flowable formulation, wettable powder, water dispersible granules, powder, granules, or the like.
  • the formulation which is used alone or by adding another inert component, can be used as a plant disease control agent.
  • the total content of a "carboxamide compound” and chlorothalonil in a “composition” is usually from 0.1% to 99% by weight, preferably from 0.2% to 90% by weight, and more preferably from 1% to 80% by weight.
  • solid carriers used for the formulation include fine powder or granules of, for example, mineral materials such as kaolin clay, attapulgite, bentonite, montmorillonite, acid clay, pyrophillite, talc, diatomaceous earth and calcite; natural organic materials such as corncob powder and walnut powder; synthesized organic materials such as urea; salts such as potassium carbonate and ammonium sulfate; synthetic inorganic materials such as synthesized hydrous silicon oxide.
  • mineral materials such as kaolin clay, attapulgite, bentonite, montmorillonite, acid clay, pyrophillite, talc, diatomaceous earth and calcite
  • natural organic materials such as corncob powder and walnut powder
  • synthesized organic materials such as urea
  • salts such as potassium carbonate and ammonium sulfate
  • synthetic inorganic materials such as synthesized hydrous silicon oxide.
  • liquid carriers examples include aromatic hydrocarbons such as xylene, alkylbenzene and methylnaphthalene; alcohols such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol mono-ethyl ether; ketones such as acetone, cyclohexanone and isophorone; vegetable oils such as soybean oil and cotton seed oil; petrolic aliphatic hydrocarbons; esters; dimethylsulfoxide; acetonitrile; and water.
  • aromatic hydrocarbons such as xylene, alkylbenzene and methylnaphthalene
  • alcohols such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol mono-ethyl ether
  • ketones such as acetone, cyclohexanone and isophorone
  • vegetable oils such as soybean oil and cotton seed oil
  • petrolic aliphatic hydrocarbons esters
  • dimethylsulfoxide acetonitrile
  • surfactants examples include anionic surfactants such as alkyl sulfate ester salts, alkylarylsulfonate salts, dialkylsulfosuccinate salts, polyoxyethylene alkylaryl ether phosphoric acid ester salts, lignin sulfonare and naphthalene sulfonate formaldehyde polycondensed products; non-ionic surfactants such as polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers and sorbitan fatty acid esters; and cationic surfactants such as alkyl trimethyl ammonium salts.
  • anionic surfactants such as alkyl sulfate ester salts, alkylarylsulfonate salts, dialkylsulfosuccinate salts, polyoxyethylene alkylaryl ether phosphoric acid ester salts, lignin sulfonare and naphthalene
  • auxiliaries for formulation examples include water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone; polysaccharides such as gum arabic, alginic acid and its salt, CMC (carboxymethylcellulose) and xanthan gum; inorganic materials such as aluminum magnesium silicate and alumina sol; preservatives; coloring agents; and stabilizers such as PAP (acidic isopropyl phosphate) and BHT.
  • water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone
  • polysaccharides such as gum arabic, alginic acid and its salt, CMC (carboxymethylcellulose) and xanthan gum
  • inorganic materials such as aluminum magnesium silicate and alumina sol
  • preservatives coloring agents
  • stabilizers such as PAP (acidic isopropyl phosphate) and BHT.
  • composition can be also prepared by formulating a "carboxamide compound” and chlorothalonil according to the method as described in the above, and then making the formulations or their diluents.
  • composition can be used for protecting plant from a plant disease.
  • plant diseases which can be controlled by the "composition” include the followings.
  • Rice diseases Magnaporthe grisea, Cochliobolus miyabeanus, Rhizoctonia solani, Gibberella fujikuroi; Wheat diseases: Erysiphe graminis, Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium nivale, Puccinia striiformis, P. graminis, P.
  • Ustilago nuda, Rhynchosporium secalis, Pyrenophora teres, Cochliobolus sativus, Pyrenophora graminea, Rhizoctonia solani; Maize diseases: Ustilago maydis, Cochliobolus heterostrophus, Gloeocercospora sorghi, Puccinia polysora, Cercospora zeae-maydis, Rhizoctonia solani;
  • Citrus diseases Diaporthe citri, Elsinoe fawcetti, Penicillium digitatum, P. italicum, Phytophthora parasitica, Phytophthora citrophthora; Apple diseases: Monilinia mali, Valsa ceratosperma, Podosphaera leucotricha, Alternaria alternata apple pathotype, Venturia inaequalis, Colletotrichum acutatum, Phytophtora cactorum; Pear diseases: Venturia nashicola, V.
  • pirina Alternaria alternata Japanese pear pathotype, Gymnosporangium haraeanum, Phytophtora cactorum; Peach diseases: Monilinia fructicola, Cladosporium carpophilum, Phomopsis sp.; Grape diseases: Elsinoe ampelina, Glomerella cingulata, Uninula necator, Phakopsora ampelopsidis, Guignardia bidwellii, Plasmopara viticola; Persimmon diseases: Gloesporium kaki, Cercospora kaki, Mycosphaerela nawae; Gourd diseases: Colletotrichum lagenarium, Sphaerotheca fuliginea, Mycosphaerella melonis, Fusarium oxysporum, Pseudoperonospora cubensis, Phytophthora sp., Pythium sp.; Tomato diseases: Alter
  • Soybean diseases Cercospora kikuchii, Elsinoe glycines, Diaporthe phaseolorum var. sojae, Septoria glycines, Cercospora sojina, Phakopsora pachyrhizi, Phytophthora sojae, Rhizoctonia solani, Corynespora casiicola, Sclerotinia sclerotiorum; Kidney bean diseases: Colletrichum lindemthianum; Peanut diseases: Cercospora personata, Cercospora arachidicola, Sclerotium rolfsii; Pea diseases : pea: Erysiphe pisi; Potato diseases: Alternaria solani, Phytophthora infestans, Phytophthora erythroseptica, Spongospora subterranean, f.
  • Agricultural crops maize, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugar cane, tobacco, and the like;
  • Vegetables Solanaceous vegetables (eggplant, tomato, green pepper, hot pepper, potato, etc.), Cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, melon, squash, etc.); Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, cauliflower, etc.), Asteraceous vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceous vegetables (Welsh onion, onion, garlic, asparagus, etc.), Umbelliferous vegetables (carrot, parsley, celery, parsnip, etc.), Chenopodiaceous vegetables (spinach,
  • the above-described plants may be those having resistance imparted by genetic engineering technique.
  • the “composition” is expected to have excellent controlling effect particularly to plant diseases caused in wheat.
  • wheat diseases to which especially excellent effect of the "composition” can be expected are Puccinia striiformis, P. graminis, P. recondita, Mycosphaerella graminicola, Stagonospora nodorum, Pyrenophora tritici-repentis, and the like.
  • compositions exemplify embodiments of the "composition”: a composition comprising "carboxamide compound (1)” and chlorothalonil; a composition comprising "carboxamide compound (2)” and chlorothalonil; a composition comprising "carboxamide compound (3)” and chlorothalonil; a composition comprising "carboxamide compound (4)” and chlorothalonil; a composition comprising "carboxamide compound (5)” and chlorothalonil;
  • compositions comprising "carboxamide compound (1)” and chlorothalonil in which the weight ratio of "carboxamide compound (1)” to chlorothalonil is 0.01/1 to 1/1; a composition comprising "carboxamide compound (2)” and chlorothalonil in which the weight ratio of "carboxamide compound (2)” to chlorothalonil is 0.01/1 to 1/1; a composition comprising "carboxamide compound (3)” and chlorothalonil in which the weight ratio of "carboxamide compound (3)” to chlorothalonil is 0.01/1 to 1/1; a composition comprising "carboxamide compound (4)” and chlorothalonil in which the weight ratio of "carboxamide compound (4)” to chlorothalonil is 0.01/1 to 1/1; a composition comprising "carboxamide compound (5)” and chlorothalonil in which the weight ratio of "carboxamide compound (5)” to chlorothalonil is 0.01/1 to 1/1;
  • controlling method can be carried out by treating a plant or the soil where a plan grows with an effective amount of a "carboxamide compound” and chlorothalonil.
  • the part of a plant to be treated is stem and leaf of a plant, seed or bulb of a plant, and the bulb means bulb, corm, rootstock, tuber, tuberous root and rhizophore.
  • the treatment of a plant or the soil where a plan grows with a "carboxamide compound” and chlorothalonil can be carried out separately at the same timing, but the treatment is usually carried out by using a "composition” in light of convenience.
  • the treatment with a “carboxamide compound” and chlorothalonil is, for example, stems and leaves application, soil application, roots application or seeds application.
  • Examples of the stems and leaves application include a treatment for surface of cultivated plant by a stem and leaves splay or a stem and tree spray.
  • Examples of the root application include a method of dipping a whole plant or root of a plant into a liquid containing a "carboxamide compound” and chlorothalonil and a method of sticking a solid preparation comprising a "carboxamide compound", chlorothalonil and a solid carrier onto root of a plant.
  • Examples of the soil application include a method of spraying a "composition" onto the soil, a method of mixing a "composition” with a soil and a method of irrigating a "composition” into the soil.
  • Examples of the seed application include a method of treating seeds or bulbs of a plant to be protected from a plant disease with a "composition". Particularly, the application can be carried out by spraying a suspension of a "composition" to the surface of seeds or bulbs, or by spreading wettable powder, emulsifiable concentrate or flowable formulation itself or a mixture thereof with a small amount of water on the seeds or the bulbs, or by dipping the seeds into a solution of a "composition” for a prescribed time, or by film coating application or pellet coating application.
  • the amount of a "carboxamide compound” and chlorothalonil used in the “controlling method” is different depending on the kind of a plant to be treated, the kind of a plant disease to be controlled and its frequency, the kind of a formulation, timing of treatment, method of treatment, place of treatment, weather condition, and the like.
  • the total amount of a "carboxamide compound” and chlorothalonil is usually from 1g to 500g / 1000m 2 , preferably from 2g to 200g / 1000m 2 , and more preferably from 10g to 100g / 1000m 2 .
  • the total amount of a "carboxamide compound” and chlorothalonil is usually from 0.001g to 10g / 1kg of the seeds, and preferably from 0.01g to 1g / 1kg of the seeds.
  • An emulsifiable concentrate, wettable powder or flowable formulation is usually used by diluting the formulation with water and spraying the diluted formulation.
  • the concentration of a "carboxamide compound” and chlorothalonil in total of the diluted formulation is usually from 0.0005 to 2% by weight and preferably from 0.005 to 1% by weight.
  • a powder formulation, granule formulation, and the like is usually used without dilution.
  • Test Example 1 Each plastic pot was filled with soil, and seeds of wheat (variety: Apogee) were seeded in the soil followed by growing for 14 days in a greenhouse. Test compounds were formulated into formulations according to Formulation Example 5, and the formulation was diluted with water to prescribed concentration. Foliar application of dilution was carried out so that dilution would adhere to surface of leaves of wheat sufficiently. After spraying, the plant was air-dried and two days after, the plant was inoculated by spraying aqueous suspension of conidiospores of Mycosphaerella graminicola (about 1,000,000/ml).
  • treated plot After the inoculation, the plants were placed under high humidity condition at 18 0 C for 3 days, taken out from the high humidity condition and then placed in a thermostatic room at 18 0 C for 14 days (hereinafter referred to as "treated plot"). Thereafter, the lesion area by Mycosphaerella graminicola was investigated. On the other hand, wheat was grown in the same way as above “treated plot” except for that the dilution of the test compound was not applied to the stems and leaves (hereinafter referred to as "non-treated plot”). The lesion area by Mycosphaerella graminicola lesion was investigated as above "treated plot".
  • a plant disease control composition comprising a "carboxamide compound” represented by formula (I) and chlorothalonil is useful for controlling plant disease.

Landscapes

  • 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

A plant disease control composition comprising a carboxamide compound represented by following formula (I), wherein R1 represents a hydrogen atom or a methyl group, and R2 represents a methyl group, a difluoromethyl group or a trifluoromethyl group, and chlorothalonil is provided by the present invention, and this composition has an excellent effect for controlling a plan disease.

Description

Plant disease control composition and its use
The present invention relates to a plant disease control composition and its use.
Many compounds have been developed for controlling plant diseases and actually used (see, for example, PTL 1 and 2).
[PTL 1] : WO86/02641
[PTL 2] : WO92/12970
An object of the present invention is to provide a composition having an excellent effect for controlling plant disease.
The inventor of the present invention studied for seeking a composition having an excellent effect for controlling plant disease and found that a composition comprising a carboxamide compound represented by following formula (I) and chlorothalonil has an excellent effect for plant diseases and then completed the present invention.
The present invention provides the following [1] to [5].
[1] A plant disease control composition comprising a carboxamide compound represented by formula (I):
Figure JPOXMLDOC01-appb-C000001
 wherein
R1 represents a hydrogen atom or a methyl group, and
R2 represents a methyl group, a difluoromethyl group or a trifluoromethyl group,
and chlorothalonil.
[2] The plant disease control composition according to above [1], wherein the weight ratio of the carboxamide compound to chlorothalonil is from 0.01/1 to 1/1 of the carboxamide compound / chlorothalonil.
[3] A method of controlling plant disease which comprises a step of treating a plant or the soil where a plan grows with an effective amount of a carboxamide compound represented by formula (I):
Figure JPOXMLDOC01-appb-C000002
 wherein
R1 represents a hydrogen atom or a methyl group, and
R2 represents a methyl group, a difluoromethyl group or a trifluoromethyl group, and chlorothalonil.
[4] The method of controlling plant disease according to above [3], wherein the weight ratio of the carboxamide compound to chlorothalonil is from 0.01/1 to 1/1.of the carboxamide compound / chlorothalonil.
[5] The method of controlling plant disease according to above [3] or [4], wherein the plant or the soil where a plan grows is wheat or the soil where wheat grows, respectively.
Advantageous Effect of Invention
According to the present invention, various plant diseases can be controlled.
The plant disease control composition of the present invention (hereinafter referred to as "composition") comprises a carboxamide compound represented by formula (I):
Figure JPOXMLDOC01-appb-C000003
 wherein
R1 and R2 represent the same meanings as defined in the above (hereinafter referred to as "carboxamide compound"),
and chlorothalonil.
The "carboxamide compound" are those as described in, for example, WO86/02641 or WO92/12970 and can be prepared by the method described therein.
Particular examples of the "carboxamide compounds" are as follows:
carboxamide compound represented by formula (1):
Figure JPOXMLDOC01-appb-C000004
 (hereinafter referred to as "carboxamide compound (1) ");
carboxamide compound represented by formula (2):
Figure JPOXMLDOC01-appb-C000005
 (hereinafter referred to as "carboxamide compound (2)");
carboxamide compound represented by formula (3):
Figure JPOXMLDOC01-appb-C000006
 (hereinafter referred to as "carboxamide compound (3)"):
carboxamide compound represented by formula (4):
Figure JPOXMLDOC01-appb-C000007
 (hereinafter referred to as "carboxamide compound (4)");
carboxamide compound represented by formula (5):
Figure JPOXMLDOC01-appb-C000008
 (hereinafter referred to as "carboxamide compound (5)").
Chlorothalonil is a known compound and described in, for example, "THE PESTICIDE MANUAL - 14th EDITION (published by BCPC) ISBN 1901396142. This compound can be obtained from the product containing said compound in the market or can be synthesized by publicly known method.
The weight ratio of the "carboxamide compound" to chlorothalonil in the "composition" is usually from 0.001/1 to 500/1, and preferably from 0.01/1 to 1/1.
Although the "composition" may be a mixture itself of a "carboxamide compound" and chlorothalonil, the "composition" is usually prepared by mixing a "carboxamide compound", chlorothalonil and an inert carrier, and if necessary, by adding a surfactant and/or another auxiliary for formulation and by formulating the mixture into oil formulation, emulsifiable concentrate, flowable formulation, wettable powder, water dispersible granules, powder, granules, or the like. The formulation, which is used alone or by adding another inert component, can be used as a plant disease control agent.
The total content of a "carboxamide compound" and chlorothalonil in a "composition" is usually from 0.1% to 99% by weight, preferably from 0.2% to 90% by weight, and more preferably from 1% to 80% by weight.
Examples of the solid carriers used for the formulation include fine powder or granules of, for example, mineral materials such as kaolin clay, attapulgite, bentonite, montmorillonite, acid clay, pyrophillite, talc, diatomaceous earth and calcite; natural organic materials such as corncob powder and walnut powder; synthesized organic materials such as urea; salts such as potassium carbonate and ammonium sulfate; synthetic inorganic materials such as synthesized hydrous silicon oxide.
Examples of the liquid carriers include aromatic hydrocarbons such as xylene, alkylbenzene and methylnaphthalene; alcohols such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol mono-ethyl ether; ketones such as acetone, cyclohexanone and isophorone; vegetable oils such as soybean oil and cotton seed oil; petrolic aliphatic hydrocarbons; esters; dimethylsulfoxide; acetonitrile; and water.
Examples of the surfactants include anionic surfactants such as alkyl sulfate ester salts, alkylarylsulfonate salts, dialkylsulfosuccinate salts, polyoxyethylene alkylaryl ether phosphoric acid ester salts, lignin sulfonare and naphthalene sulfonate formaldehyde polycondensed products; non-ionic surfactants such as polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers and sorbitan fatty acid esters; and cationic surfactants such as alkyl trimethyl ammonium salts.
Examples of the other auxiliaries for formulation include water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone; polysaccharides such as gum arabic, alginic acid and its salt, CMC (carboxymethylcellulose) and xanthan gum; inorganic materials such as aluminum magnesium silicate and alumina sol; preservatives; coloring agents; and stabilizers such as PAP (acidic isopropyl phosphate) and BHT.
The "composition" can be also prepared by formulating a "carboxamide compound" and chlorothalonil according to the method as described in the above, and then making the formulations or their diluents.
The "composition" can be used for protecting plant from a plant disease.
Examples of plant diseases which can be controlled by the "composition" include the followings.
Rice diseases: Magnaporthe grisea, Cochliobolus miyabeanus, Rhizoctonia solani, Gibberella fujikuroi;
Wheat diseases: Erysiphe graminis, Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium nivale, Puccinia striiformis, P. graminis, P. recondita, Micronectriella nivale, Typhula sp., Ustilago tritici, Tilletia caries, Pseudocercosporella herpotrichoides, Mycosphaerella graminicola, Stagonospora nodorum, Pyrenophora tritici-repentis;
Barley diseases: Erysiphe graminis, Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium nivale, Puccinia striiformis, P. graminis, P. hordei, Ustilago nuda, Rhynchosporium secalis, Pyrenophora teres, Cochliobolus sativus, Pyrenophora graminea, Rhizoctonia solani;
Maize diseases: Ustilago maydis, Cochliobolus heterostrophus, Gloeocercospora sorghi, Puccinia polysora, Cercospora zeae-maydis, Rhizoctonia solani;
Citrus diseases: Diaporthe citri, Elsinoe fawcetti, Penicillium digitatum, P. italicum, Phytophthora parasitica, Phytophthora citrophthora;
Apple diseases: Monilinia mali, Valsa ceratosperma, Podosphaera leucotricha, Alternaria alternata apple pathotype, Venturia inaequalis, Colletotrichum acutatum, Phytophtora cactorum;
Pear diseases: Venturia nashicola, V. pirina, Alternaria alternata Japanese pear pathotype, Gymnosporangium haraeanum, Phytophtora cactorum;
Peach diseases: Monilinia fructicola, Cladosporium carpophilum, Phomopsis sp.;
Grape diseases: Elsinoe ampelina, Glomerella cingulata, Uninula necator, Phakopsora ampelopsidis, Guignardia bidwellii, Plasmopara viticola;
Persimmon diseases: Gloesporium kaki, Cercospora kaki, Mycosphaerela nawae;
Gourd diseases: Colletotrichum lagenarium, Sphaerotheca fuliginea, Mycosphaerella melonis, Fusarium oxysporum, Pseudoperonospora cubensis, Phytophthora sp., Pythium sp.;
Tomato diseases: Alternaria solani, Cladosporium fulvum, Phytophthora infestans;
Eggplant diseases: Phomopsis vexans, Erysiphe cichoracearum;
Brassicaceous vegetable diseases: Alternaria japonica, Cercosporella brassicae, Plasmodiophora brassicae, Peronospora parasitica;
Welsh onion diseases: Puccinia allii, Peronospora destructor;
Soybean diseases: Cercospora kikuchii, Elsinoe glycines, Diaporthe phaseolorum var. sojae, Septoria glycines, Cercospora sojina, Phakopsora pachyrhizi, Phytophthora sojae, Rhizoctonia solani, Corynespora casiicola, Sclerotinia sclerotiorum;
Kidney bean diseases: Colletrichum lindemthianum;
Peanut diseases: Cercospora personata, Cercospora arachidicola, Sclerotium rolfsii;
Pea diseases : pea: Erysiphe pisi;
Potato diseases: Alternaria solani, Phytophthora infestans, Phytophthora erythroseptica, Spongospora subterranean, f. sp. Subterranean;
Strawberry diseases: Sphaerotheca humuli, Glomerella cingulata;
Tea diseases: Exobasidium reticulatum, Elsinoe leucospila, Pestalotiopsis sp., Colletotrichum theae-sinensis;
Tobacco diseases: Alternaria longipes, Erysiphe cichoracearum, Colletotrichum tabacum, Peronospora tabacina, Phytophthora nicotianae;
Rapeseed diseases: Sclerotinia sclerotiorum, Rhizoctonia solani;
Cotton diseases: Rhizoctonia solani;
Beet diseases: Cercospora beticola, Thanatephorus cucumeris, Thanatephorus cucumeris, Aphanomyces cochlioides;
Rose diseases: Diplocarpon rosae, Sphaerotheca pannosa, Peronospora sparsa;
Diseases of chrysanthemum and asteraceae: Bremia lactuca, Septoria chrysanthemi-indici, Puccinia horiana;
Diseases of various plants: Pythium aphanidermatum, Pythium debarianum, Pythium graminicola, Pythium irregulare, Pythium ultimum, Botrytis cinerea, Sclerotinia sclerotiorum;
Radish diseases: Alternaria brassicicola;
Zoysia diseases: Sclerotinia homeocarpa, Rhizoctonia solani;
Banana diseases: Mycosphaerella fijiensis, Mycosphaerella musicola;
Sunflower diseases: Plasmopara halstedii;
Seed diseases or diseases in the initial stage of growth of various plants caused by Aspergillus spp., Penicillium spp., Fusarium spp., Gibberella spp., Tricoderma spp., Thielaviopsis spp., Rhizopus spp., Mucor spp., Corticium spp., Rhoma spp., Rhizoctonia spp., Diplodia spp., or the like;
Virus diseases of various plants mediated by Polymixa spp., Olpidium spp., or the like.
Examples of the plants for which the "composition" can be used include the followings:
Agricultural crops: maize, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugar cane, tobacco, and the like;
Vegetables: Solanaceous vegetables (eggplant, tomato, green pepper, hot pepper, potato, etc.), Cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, melon, squash, etc.); Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, cauliflower, etc.), Asteraceous vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceous vegetables (Welsh onion, onion, garlic, asparagus, etc.), Umbelliferous vegetables (carrot, parsley, celery, parsnip, etc.), Chenopodiaceous vegetables (spinach, chard, etc.), Lamiaceous vegetables (Japanese basil, mint, basil, etc.), strawberry, sweet potato, yam, aroid, and the like;
Flowering plants;
Ornamental foliage plants;
Turf;
Fruit trees: pome fruits (apple, common pear, Japanese pear, Chinese quince, quince, etc.), stone fruits (peach, plum, nectarine, Japanese plum, cherry, apricot, prune, etc.), citrus (mandarin, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazel nut, almond, pistachio, cashew nut, macadamia nut, etc.), berry fruits (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, olive, loquat, banana, coffee, date, coconut palm, and the like;
Trees other than fruit trees: tea, mulberry, flowering trees, street trees (ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew), and the like.
The above-described plants may be those having resistance imparted by genetic engineering technique.
Among the above plants, the "composition" is expected to have excellent controlling effect particularly to plant diseases caused in wheat.
Among the above plant diseases, wheat diseases to which especially excellent effect of the "composition" can be expected are Puccinia striiformis, P. graminis, P. recondita, Mycosphaerella graminicola, Stagonospora nodorum, Pyrenophora tritici-repentis, and the like.
Following compositions exemplify embodiments of the "composition":
a composition comprising "carboxamide compound (1)" and chlorothalonil;
a composition comprising "carboxamide compound (2)" and chlorothalonil;
a composition comprising "carboxamide compound (3)" and chlorothalonil;
a composition comprising "carboxamide compound (4)" and chlorothalonil;
a composition comprising "carboxamide compound (5)" and chlorothalonil;
a composition comprising "carboxamide compound (1)" and chlorothalonil in which the weight ratio of "carboxamide compound (1)" to chlorothalonil is 0.01/1 to 1/1;
a composition comprising "carboxamide compound (2)" and chlorothalonil in which the weight ratio of "carboxamide compound (2)" to chlorothalonil is 0.01/1 to 1/1;
a composition comprising "carboxamide compound (3)" and chlorothalonil in which the weight ratio of "carboxamide compound (3)" to chlorothalonil is 0.01/1 to 1/1;
a composition comprising "carboxamide compound (4)" and chlorothalonil in which the weight ratio of "carboxamide compound (4)" to chlorothalonil is 0.01/1 to 1/1;
a composition comprising "carboxamide compound (5)" and chlorothalonil in which the weight ratio of "carboxamide compound (5)" to chlorothalonil is 0.01/1 to 1/1;
The method of controlling plant disease (hereinafter referred to as "controlling method") can be carried out by treating a plant or the soil where a plan grows with an effective amount of a "carboxamide compound" and chlorothalonil.
The part of a plant to be treated is stem and leaf of a plant, seed or bulb of a plant, and the bulb means bulb, corm, rootstock, tuber, tuberous root and rhizophore.
In the "controlling method", the treatment of a plant or the soil where a plan grows with a "carboxamide compound" and chlorothalonil can be carried out separately at the same timing, but the treatment is usually carried out by using a "composition" in light of convenience.
In the "controlling method", the treatment with a "carboxamide compound" and chlorothalonil is, for example, stems and leaves application, soil application, roots application or seeds application.
Examples of the stems and leaves application include a treatment for surface of cultivated plant by a stem and leaves splay or a stem and tree spray.
Examples of the root application include a method of dipping a whole plant or root of a plant into a liquid containing a "carboxamide compound" and chlorothalonil and a method of sticking a solid preparation comprising a "carboxamide compound", chlorothalonil and a solid carrier onto root of a plant.
Examples of the soil application include a method of spraying a "composition" onto the soil, a method of mixing a "composition" with a soil and a method of irrigating a "composition" into the soil.
Examples of the seed application include a method of treating seeds or bulbs of a plant to be protected from a plant disease with a "composition". Particularly, the application can be carried out by spraying a suspension of a "composition" to the surface of seeds or bulbs, or by spreading wettable powder, emulsifiable concentrate or flowable formulation itself or a mixture thereof with a small amount of water on the seeds or the bulbs, or by dipping the seeds into a solution of a "composition" for a prescribed time, or by film coating application or pellet coating application.
The amount of a "carboxamide compound" and chlorothalonil used in the "controlling method" is different depending on the kind of a plant to be treated, the kind of a plant disease to be controlled and its frequency, the kind of a formulation, timing of treatment, method of treatment, place of treatment, weather condition, and the like.
When a "composition" is applied to stems and/or leaves of a plant or to the soil where a plan grows, the total amount of a "carboxamide compound" and chlorothalonil is usually from 1g to 500g / 1000m2, preferably from 2g to 200g / 1000m2, and more preferably from 10g to 100g / 1000m2.
When a "composition" is applied to seeds of a plant, the total amount of a "carboxamide compound" and chlorothalonil is usually from 0.001g to 10g / 1kg of the seeds, and preferably from 0.01g to 1g / 1kg of the seeds.
An emulsifiable concentrate, wettable powder or flowable formulation is usually used by diluting the formulation with water and spraying the diluted formulation. In this case, the concentration of a "carboxamide compound" and chlorothalonil in total of the diluted formulation is usually from 0.0005 to 2% by weight and preferably from 0.005 to 1% by weight.
A powder formulation, granule formulation, and the like is usually used without dilution.
Example
The present invention is further explained in detail with Formulation Examples and Test Examples. However, the present invention is not limited by the following Examples.
In the following Examples, "part" means "part by weight" unless otherwise provided.
Formulation Example 1
One of "carboxamide compounds" (1) to (5) (1 part), chlorothalonil (9 parts), a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1:1) (35 parts) and water (55 parts) are mixed and milled by wet-milling method to give each of formulations, respectively.
Formulation Example 2
One of "carboxamide compounds" (1) to (5) (3 parts), chlorothalonil (12 parts), sorbitan tri-oleate (1.5 parts) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts) are mixed and the mixture is milled by wet-milling method. To the milled mixture is added an aqueous solution (45 parts) containing xanthan gum (0.05 parts) and aluminum magnesium silicate (0.1 part), and further propylene glycol (10 parts) is added to the mixture. The resultant mixture is mixed by stirring to give each of formulations, respectively.
Formulation Example 3
One of "carboxamide compounds" (1) to (5) (1 part), chlorothalonil (4 parts), synthesized hydrous silicon oxide (1 part), calcium ligninsulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are thoroughly mixed and milled. Water is added to the mixture and the mixture is sufficiently kneaded, granulated and then dried to give each of formulations, respectively.
Formulation Example 4
One of "carboxamide compounds" (1) to (5) (12.5 parts), chlorothalonil (37.5 parts), calcium ligninsulfonate (3 parts), sodium lauryl sulfate (2 parts) and synthesized hydrous silicon oxide (45 parts) are thoroughly mixed and milled to give each of formulations, respectively.
Formulation Example 5
One of "carboxamide compounds" (1) to (5) (0.5 parts), chlorothalonil (4.5 parts), kaolin clay (85 parts) and talc (10 parts) are thoroughly mixed and milled to give each of formulations, respectively.
Test Examples using each of the "compositions" are shown in the following.
Test Example 1
Each plastic pot was filled with soil, and seeds of wheat (variety: Apogee) were seeded in the soil followed by growing for 14 days in a greenhouse. Test compounds were formulated into formulations according to Formulation Example 5, and the formulation was diluted with water to prescribed concentration. Foliar application of dilution was carried out so that dilution would adhere to surface of leaves of wheat sufficiently. After spraying, the plant was air-dried and two days after, the plant was inoculated by spraying aqueous suspension of conidiospores of Mycosphaerella graminicola (about 1,000,000/ml). After the inoculation, the plants were placed under high humidity condition at 180C for 3 days, taken out from the high humidity condition and then placed in a thermostatic room at 180C for 14 days (hereinafter referred to as "treated plot"). Thereafter, the lesion area by Mycosphaerella graminicola was investigated.
On the other hand, wheat was grown in the same way as above "treated plot" except for that the dilution of the test compound was not applied to the stems and leaves (hereinafter referred to as "non-treated plot"). The lesion area by Mycosphaerella graminicola lesion was investigated as above "treated plot".
On the basis of the above lesion areas in "treated plot" and "non-treated plot", efficacy in "treated plot" was evaluated by the following calculation formula (1).
The results are shown in Table 1 and Table 2.
Calculation formula (1):
Efficacy (%) =
[1 - (lesion area in "treated plot" / lesion area in "non-treated plot")] x 100
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000002
A plant disease control composition comprising a "carboxamide compound" represented by formula (I) and chlorothalonil is useful for controlling plant disease.

Claims (5)

  1. A plant disease control composition comprising a carboxamide compound represented by formula (I):
    Figure JPOXMLDOC01-appb-C000009
     wherein
    R1 represents a hydrogen atom or a methyl group, and
    R2 represents a methyl group, a difluoromethyl group or a trifluoromethyl group,
    and chlorothalonil.
  2. The plant disease control composition according to claim 1, wherein the weight ratio of the carboxamide compound to chlorothalonil is from 0.01/1 to 1/1 of the carboxamide compound / chlorothalonil.
  3. A method of controlling plant disease which comprises a step of treating a plant or the soil where a plan grows with an effect amount of a carboxamide compound represented by formula (I):
    Figure JPOXMLDOC01-appb-C000010
     wherein
    R1 represents a hydrogen atom or a methyl group, and
    R2 represents a methyl group, a difluoromethyl group or a trifluoromethyl group,
    and chlorothalonil.
  4. The method of controlling plant disease according to claim 3, wherein the weight ratio of the carboxamide compound to chlorothalonil is from 0.01/1 to 1/1 of the carboxamide compound / chlorothalonil.
  5. The method of controlling plant disease according to claim 3 or claim 4, wherein the plant or the soil where a plan grows is wheat or the soil where wheat grows, respectively.
PCT/JP2011/002421 2010-04-28 2011-04-25 Plant disease control composition and its use WO2011135838A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US13/643,818 US8969399B2 (en) 2010-04-28 2011-04-25 Plant disease control composition and its use
KR1020127028103A KR101812360B1 (en) 2010-04-28 2011-04-25 Compositions for controlling plant fungal diseases comprising carboxamide compound and chlorothalonil
BR112012027382-5A BR112012027382B1 (en) 2010-04-28 2011-04-25 Plant disease control composition comprising a carboxamide compound and plant disease control method
MX2012012306A MX2012012306A (en) 2010-04-28 2011-04-25 Plant disease control composition and its use.
CN2011800208409A CN102858165A (en) 2010-04-28 2011-04-25 Plant disease control composition and its use
CA2797382A CA2797382C (en) 2010-04-28 2011-04-25 Compositions for controlling plant fungal diseases comprising carboxamide compound and chlorothalonil

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010-104098 2010-04-28
JP2010104098A JP5724212B2 (en) 2010-04-28 2010-04-28 Plant disease control composition and use thereof

Publications (1)

Publication Number Publication Date
WO2011135838A1 true WO2011135838A1 (en) 2011-11-03

Family

ID=44861160

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2011/002421 WO2011135838A1 (en) 2010-04-28 2011-04-25 Plant disease control composition and its use

Country Status (8)

Country Link
US (1) US8969399B2 (en)
JP (1) JP5724212B2 (en)
KR (1) KR101812360B1 (en)
CN (1) CN102858165A (en)
BR (1) BR112012027382B1 (en)
CA (1) CA2797382C (en)
MX (1) MX2012012306A (en)
WO (1) WO2011135838A1 (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013186325A1 (en) 2012-06-15 2013-12-19 Stichting I-F Product Collaboration Synergistic compositions for the protection of agrarian crops and the use thereof
WO2014083088A2 (en) 2012-11-30 2014-06-05 Bayer Cropscience Ag Binary fungicidal mixtures
WO2014083089A1 (en) 2012-11-30 2014-06-05 Bayer Cropscience Ag Ternary fungicidal and pesticidal mixtures
WO2014082950A1 (en) 2012-11-30 2014-06-05 Bayer Cropscience Ag Ternary fungicidal mixtures
WO2014083031A2 (en) 2012-11-30 2014-06-05 Bayer Cropscience Ag Binary pesticidal and fungicidal mixtures
WO2014083033A1 (en) 2012-11-30 2014-06-05 Bayer Cropsience Ag Binary fungicidal or pesticidal mixture
WO2019195591A1 (en) 2018-04-04 2019-10-10 Fmc Corporation Emulsifiable concentrate formulations of sdhi fungicides

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986002641A1 (en) * 1984-10-29 1986-05-09 Sumitomo Chemical Company, Limited Pyrazolecarboxamide derivatives, process for their preparation, and bactericides containing them as effective ingredients
JPS6296472A (en) * 1985-10-22 1987-05-02 Sumitomo Chem Co Ltd Pyrazolecarboxamide derivative and germicide containing said derivative as active constituent
WO1992012970A1 (en) * 1991-01-28 1992-08-06 Monsanto Company 3-difluoromethylpyrazolecarboxamide fungicides
JP2009502747A (en) * 2005-07-14 2009-01-29 ビーエーエスエフ ソシエタス・ヨーロピア Bactericidal mixtures based on 1-methyl-pyrazol-4-ylcarboxyanilides

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2517176A1 (en) 1981-12-01 1983-06-03 Rhone Poulenc Agrochimie INSECTICIDE AND ACARICIDE ASSOCIATION OF PYRETHROID
WO1995027693A1 (en) 1994-04-06 1995-10-19 Shionogi & Co., Ltd. α-SUBSTITUTED PHENYLACETIC ACID DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND AGRICULTURAL BACTERICIDE CONTAINING THE SAME
AR036872A1 (en) 2001-08-13 2004-10-13 Du Pont ANTRANILAMIDE COMPOSITE, COMPOSITION THAT INCLUDES IT AND METHOD FOR CONTROLLING AN INVERTEBRATE PEST
US7247647B2 (en) 2003-01-28 2007-07-24 E. I. Du Pont De Nemours And Company Cyano anthranilamide insecticides
DE10347090A1 (en) * 2003-10-10 2005-05-04 Bayer Cropscience Ag Synergistic fungicidal drug combinations
RS52173B (en) 2004-02-18 2012-08-31 Ishihara Sangyo Kaisha Ltd. Anthranilamides, process for the production thereof, and pest controllers containing the same
JP4150379B2 (en) 2004-02-18 2008-09-17 石原産業株式会社 Anthranilamides, production methods thereof, and pest control agents containing them
GB0422401D0 (en) * 2004-10-08 2004-11-10 Syngenta Participations Ag Fungicidal compositions
US20090239748A1 (en) * 2005-06-30 2009-09-24 Basf Aktiengesellschaft Fungicidal Mixtures Based on 2,5-Disubstituted N-Biphenylpyrazolcarboxamides
JP5186751B2 (en) 2005-10-14 2013-04-24 住友化学株式会社 Hydrazide compounds and their pest control applications
US7867949B2 (en) 2005-10-14 2011-01-11 Sumitomo Chemical Company, Limited Hydrazide compound and pesticidal use of the same
TWI398433B (en) 2006-02-10 2013-06-11 Dow Agrosciences Llc Insecticidal n-substituted (6-haloalkylpyridin-3-yl)alkyl sulfoximines
TWI435863B (en) * 2006-03-20 2014-05-01 Nihon Nohyaku Co Ltd N-2-(hetero) arylethylcarboxamide derivative and pest controlling
JP2008100946A (en) 2006-10-19 2008-05-01 Bayer Cropscience Ag Fungicidal and insecticidal composition
CL2008000979A1 (en) 2007-04-11 2008-10-17 Sumitomo Chemical Co PROCESS TO PRODUCE A COMPOUND DERIVED FROM 2-PIRIDIN-2-IL-2H-PIRAZOL-3-PHENYLAMIDE; INTERMEDIARY COMPOUNDS; THE COMPOUND IN YES; PESTICIDE COMPOSITION CONTAINING SUCH COMPOUND; USE OF SUCH COMPOUND AS A PESTICIDE; AND METHOD FOR CONTROL
JP5365047B2 (en) * 2008-03-28 2013-12-11 住友化学株式会社 Plant disease control composition and plant disease control method
JP2010013389A (en) 2008-07-03 2010-01-21 Nissan Chem Ind Ltd Agrochemical composition exhibiting promoted elution into water
JP5939557B2 (en) 2008-08-19 2016-06-22 石原産業株式会社 Method for inhibiting decomposition of active ingredients of agricultural chemicals
AR073109A1 (en) 2008-08-26 2010-10-13 Sumitomo Chemical Co DERIVATIVES OF N-BENZOTIAZOL ACETAMIDE USEFUL TO CONTROL PHYTO-DISEASES AND COMPOSITIONS THAT CONTAIN THEM.
WO2010024365A1 (en) 2008-08-26 2010-03-04 Sumitomo Chemical Company, Limited Amide compounds and use thereof
JP2010083869A (en) 2008-09-08 2010-04-15 Nissan Chem Ind Ltd Agrochemical packaged bag for applying to paddy field water inlet
JP2010083883A (en) 2008-09-08 2010-04-15 Nissan Chem Ind Ltd Isoxazoline-substituted benzamide compound and harmful organism-controlling agent

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986002641A1 (en) * 1984-10-29 1986-05-09 Sumitomo Chemical Company, Limited Pyrazolecarboxamide derivatives, process for their preparation, and bactericides containing them as effective ingredients
JPS6296472A (en) * 1985-10-22 1987-05-02 Sumitomo Chem Co Ltd Pyrazolecarboxamide derivative and germicide containing said derivative as active constituent
WO1992012970A1 (en) * 1991-01-28 1992-08-06 Monsanto Company 3-difluoromethylpyrazolecarboxamide fungicides
JP2009502747A (en) * 2005-07-14 2009-01-29 ビーエーエスエフ ソシエタス・ヨーロピア Bactericidal mixtures based on 1-methyl-pyrazol-4-ylcarboxyanilides

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013186325A1 (en) 2012-06-15 2013-12-19 Stichting I-F Product Collaboration Synergistic compositions for the protection of agrarian crops and the use thereof
US11477983B2 (en) 2012-06-15 2022-10-25 Stichting I-F Product Collaboration Synergistic compositions for the protection of agrarian crops and the use thereof
EP3788875A1 (en) 2012-06-15 2021-03-10 Stichting I-F Product Collaboration Synergistic compositions for the protection of agrarian crops and the use thereof
US9615578B2 (en) 2012-11-30 2017-04-11 Bayer Cropscience Ag Binary fungicidal mixtures
US9775351B2 (en) 2012-11-30 2017-10-03 Bayer Cropscience Ag Ternary fungicidal and pesticidal mixtures
WO2014083033A1 (en) 2012-11-30 2014-06-05 Bayer Cropsience Ag Binary fungicidal or pesticidal mixture
CN104981162A (en) * 2012-11-30 2015-10-14 拜耳作物科学股份公司 Ternary fungicidal mixtures
US9510596B2 (en) 2012-11-30 2016-12-06 Bayer Cropscience Ag Binary pesticidal and fungicidal mixtures
WO2014082950A1 (en) 2012-11-30 2014-06-05 Bayer Cropscience Ag Ternary fungicidal mixtures
US9775349B2 (en) 2012-11-30 2017-10-03 Bayer Cropscience Ag Binary fungicidal or pesticidal mixture
WO2014083031A2 (en) 2012-11-30 2014-06-05 Bayer Cropscience Ag Binary pesticidal and fungicidal mixtures
US9943082B2 (en) 2012-11-30 2018-04-17 Bayer Cropscience Ag Ternary fungicidal mixtures
EA030235B1 (en) * 2012-11-30 2018-07-31 Байер Кропсайенс Акциенгезельшафт Ternary fungicidal mixtures
US10111434B2 (en) 2012-11-30 2018-10-30 Bayer Cropscience Ag Binary fungicidal mixtures
WO2014083088A2 (en) 2012-11-30 2014-06-05 Bayer Cropscience Ag Binary fungicidal mixtures
US10575522B2 (en) 2012-11-30 2020-03-03 Bayer Cropscience Ag Ternary fungicidal mixtures
WO2014083089A1 (en) 2012-11-30 2014-06-05 Bayer Cropscience Ag Ternary fungicidal and pesticidal mixtures
WO2019195591A1 (en) 2018-04-04 2019-10-10 Fmc Corporation Emulsifiable concentrate formulations of sdhi fungicides

Also Published As

Publication number Publication date
US20130102647A1 (en) 2013-04-25
CA2797382C (en) 2018-04-10
JP5724212B2 (en) 2015-05-27
MX2012012306A (en) 2012-11-23
US8969399B2 (en) 2015-03-03
CA2797382A1 (en) 2011-11-03
CN102858165A (en) 2013-01-02
KR101812360B1 (en) 2017-12-26
BR112012027382A2 (en) 2015-09-15
BR112012027382B1 (en) 2018-05-15
KR20130066590A (en) 2013-06-20
JP2011231064A (en) 2011-11-17

Similar Documents

Publication Publication Date Title
CA2797532C (en) Plant disease controlling compositions comprising a carboxamide compound and a strobilurin fungicide
EP2563135A1 (en) Plant disease control composition and its use
US8969393B2 (en) Plant disease control composition and its use
CA2797534C (en) Plant disease control compositions comprising a carboxamide compound and metalaxyl or benalaxyl
EP2563140B1 (en) Plant disease control composition and its use
US9161539B2 (en) Plant disease control composition and its use
CA2797382C (en) Compositions for controlling plant fungal diseases comprising carboxamide compound and chlorothalonil

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201180020840.9

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11774624

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: MX/A/2012/012306

Country of ref document: MX

ENP Entry into the national phase

Ref document number: 2797382

Country of ref document: CA

ENP Entry into the national phase

Ref document number: 20127028103

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 3518/KOLNP/2012

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 13643818

Country of ref document: US

122 Ep: pct application non-entry in european phase

Ref document number: 11774624

Country of ref document: EP

Kind code of ref document: A1

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112012027382

Country of ref document: BR

ENP Entry into the national phase

Ref document number: 112012027382

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20121025