plant disease control composition and method comprising a pyridazine compound

专利摘要:
plant disease control compositions and their use. a plant disease control composition containing a pyridazine compound represented by the formula (i), wherein r1 represents a chlorine atom, a bromine atom, a cyano group or a methyl group, er4 24 represents a hydrogen atom or a fluorine atom, and at least one compound of qol selected from group (a). group (a): the group consisting of dimoxystrobin, azoxystrobin, fluoxastrobin, piraclostrobin, famoxadone, cresoxime methyl, picoxystrobin, trifloxystrobin, n-methyl- <244> -methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide and fenamidone.
公开号:BR112013003147B1
申请号:R112013003147
申请日:2011-08-09
公开日:2018-10-16
发明作者:matsuzaki Yuichi
申请人:Sumitomo Chemical Co；
IPC主号:

专利说明:

(54) Title: COMPOSITION AND METHOD OF PLANT DISEASE CONTROL
UNDERSTANDING A PYRIDAZINE COMPOUND (51) lnt.CI .: A01N 43/58; A01N 39/02; A01N 43/54; A01N 37/50; A01N 47/24; A01N 43/76; A01N 43/40; A01N 47/36; A01N 43/50; A01P 3/00 (30) Unionist Priority: 10/08/2010 JP 2010-179299 (73) Holder (s): SUMITOMO CHEMICAL COMPANY, LIMITED (72) Inventor (s): YUICHI MATSUZAKI (85) Phase Start Date National: 08/02/2013
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Descriptive Report of the Invention Patent for COMPOSITION AND METHOD OF CONTROL OF PLANT DISEASES UNDERSTANDING A PYRIDAZINE COMPOUND.
TECHNICAL FIELD
The present invention relates to a plant disease control composition and its use.
PREVIOUS TECHNIQUE
Conventionally, many compounds to control plant diseases have been developed and put to practical use (see, for example, Patent Literature 1, Patent Literature 2).
LIST OF QUOTES
PATENT LITERATURE
Patent literature 1: International Publication No. WO 2005/121104.
Patent literature 2: International Publication No. WO 2006/001175.
SUMMARY OF THE INVENTION TECHNICAL PROBLEM
An object of the present invention is to provide a composition having excellent efficacy in the control of plant diseases.
SOLUTION TO THE PROBLEM
The present invention mainly provides a plant disease control composition containing a pyridazine compound represented by the following formula (I) and at least one Qol compound selected from the group (A) below. The composition has an excellent effectiveness in the control of plant diseases.
More specifically, the present invention is as follows.
[1] A plant disease control composition, containing a pyridazine compound represented by formula (I):
03/13/2018, p. 16/23
2/40
Η * where
R1 represents a chlorine atom, a bromine atom, a cyano group or a methyl group, and
R2 represents a hydrogen atom or a fluorine atom, and at least one Qol compound selected from Group (A).
A group):
A group consisting of dimoxystrobin, azoxystrobin, fluoxastrobin, pyraclostrobin, famoxadone, cresoxymethyl, picoxystrobin, trifloxystrobin, N-methyl-a-methoxy-imino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide and phenamidone.
[2] The plant disease control composition according to [1], wherein the weight ratio of the pyridazine compound and the Qol compound satisfies the pyridazine compound / Qol compound = 0.1 / 1 a 10/1.
[3] A method for the control of plant diseases, including the step of applying effective amounts of a pyridazine compound represented by formula (I):
on what
R1 represents a chlorine atom, a bromine atom, a cyano group or a methyl group, and
R2 represents a hydrogen atom or a fluorine atom, and at least one Qol compound selected from Group (A) in a plant or soil for the growth of a plant.
A group):
A group consisting of dimoxystrobin, azoxystrobin, fluoxastrobin, pyraclostrobin, famoxadone, cresoxymethyl, picoxystrobin, trifloxystrobin, N-methyl-a-methoxy-imino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide and phenamidone.
[4] The plant disease control method according to [3], where
3/40 the weight ratio of the pyridazine compound and the Qol compound satisfies the pyridazine compound / Qol compound = 0.1 / 1 to 10/1.
[5] The method for controlling plant diseases according to [3] or [4], where the plant or soil for growing a plant is wheat or soil for growing wheat.
ADVANTAGE EFFECTS OF THE INVENTION
Plant diseases can be controlled by the present invention.
DESCRIPTION OF MODALITIES
The plant disease control composition of the present invention (hereinafter referred to as the composition of the present invention) contains a pyridazine compound represented by formula (I):
on what
R1 represents a chlorine atom, a bromine atom, a cyano group or a methyl group, and
R2 represents a hydrogen atom or a fluorine atom (hereinafter referred to as the pyridazine compound), and at least one Qol compound (hereinafter referred to as the Qol compound) selected from Group (A).
A group):
A group consisting of dimoxystrobin, azoxystrobin, fluoxastrobin, pyraclostrobin, famoxadone, cresoxymethyl, picoxystrobin, trifloxystrobin, N-methyl-a-methoxy-imino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide and phenamidone.
Examples of the pyridazine compound to be used in the composition of the present invention include the following pyridazine compounds: a pyridazine compound represented by formula (I) wherein R1 is a chlorine atom or a methyl group;
4/40 a pyridazine compound represented by formula (I) wherein R1 is a chlorine atom;
a pyridazine compound represented by formula (I) wherein R1 is a methyl group;
a pyridazine compound represented by formula (I) wherein R1 is a cyano group;
a pyridazine compound represented by formula (I) in which
R2 is a hydrogen atom;
a pyridazine compound represented by formula (I) in which
R2 is a fluorine atom;
a pyridazine compound represented by formula (I) in which R1 is a chlorine atom or a methyl group and R2 is a hydrogen atom; and a pyridazine compound represented by formula (I) in which R1 is a chlorine atom or a methyl group and R2 is a fluorine atom.
Specific examples of the pyridazine compound include the following compounds:
a pyridazine compound represented by formula (I) where R1 is a chlorine atom and R2 is a hydrogen atom (hereinafter referred to as the pyridazine compound (1));
a pyridazine compound represented by formula (I) wherein R1 is a bromine atom and R2 is a hydrogen atom (hereinafter referred to as the pyridazine compound (2));
a pyridazine compound represented by formula (I) where R1 is a group and cyano and R2 is a hydrogen atom (hereinafter referred to as the pyridazine compound (3));
a pyridazine compound represented by formula (I) where R1 is a methyl group and R2 is a hydrogen atom (hereinafter referred to as the pyridazine compound (4));
a pyridazine compound represented by formula (I) wherein R1 is a chlorine atom and R2 is a fluorine atom (hereinafter referred to as the pyridazine compound (5));
a pyridazine compound represented by formula (I) where R1 is a
5/40 bromine atom and R2 is a fluorine atom (hereinafter referred to as the pyridazine compound (6));
a pyridazine compound represented by formula (I) wherein R1 is a cyano group and R2 is a fluorine atom (hereinafter referred to as the pyridazine compound (7)); and a pyridazine compound represented by formula (I) where R1 is a methyl group and R2 is a fluorine atom (hereinafter referred to as the pyridazine compound (8)).
Of the pyridazine compounds, the pyridazine compound represented by formula (I) wherein R1 is a chlorine atom or a bromine atom can be produced by a method described, for example, in International Publication No. WO 2005/121104.
Of the pyridazine compounds, the pyridazine compound represented by formula (I) in which R1 is a methyl group can be produced by a method described, for example, in International Publication No. WO 2006/001175.
Of the pyridazine compounds, a compound (I-2) represented by the formula (I) in which R1 is a cyano group can be produced by reacting, for example, a compound (1-1) represented by the formula (I) in that R1 is a bromine atom among copper cyanide pyridazine compounds.
The reaction is usually carried out in the presence of a solvent. As the solvent to be used in the reaction, for example, a polar aprotic solvent such as Ν, Ν-dimethylacetamide is mentioned.
The amount of copper cyanide to be used in the reaction is usually 1 to 1.5 mol with respect to 1 mol of the compound (1-1) through the
6/40 reason.
The reaction temperature of the reaction generally falls within the range of 120 to 180 oC and the reaction time generally falls within the range of 1 to 24 hours.
After completion of the reaction, for example, the reaction mixture is mixed with water and an organic solvent and filtered. After the filtrate is separated, the obtained organic layer is further washed with water, dried and concentrated. Through these operations, the compound (I-2) can be isolated. The isolated compound (I-2) can be further purified by chromatography, recrystallization, and others.
Of the pyridazine compounds, a pyridazine compound (I-4) represented by the formula (I) in which R1 is a methyl group can be produced by reacting a pyridazine compound (I-3) in which R1 is an atom chlorine between pyridazine compounds with a Grignard reagent represented by formula (II):
CH3-MgX (II) where X represents a bromine atom or a chlorine atom in the presence of an iron catalyst.
The reaction is usually carried out in the presence of a solvent. As the solvent to be used in the reaction, for example, tetrahydrofuran, diethyl ether and N-methylpyrrolidone and a mixture of these are mentioned. In the case where the reaction solvent is a mixture of tetrahydrofuran and N-methylpyrrolidone, the mixing ratio (volume ratio) from tetrahydrofuran to N-methylpyrrolidone generally falls within the range of 30: 1 to 3: 1.
As the iron catalyst to be used in the reaction, for example 7/40 pio, iron (III) acetylacetonate and iron (III) chloride are mentioned. The amount of iron catalyst to be used is generally 0.01 to 0.3 mol with respect to 1 mol of the compound (I-3) through the ratio.
The reaction temperature of the reaction generally falls within the range of -20 oC to 30 oC and the reaction time generally falls within the range of 0.1 to 6 hours.
After completion of the reaction, for example, the reaction mixture is mixed with hydrochloric acid and extracted with an organic solvent. The obtained organic layer is washed with water, dried and concentrated. Through these operations, the compound (I-4) can be isolated. The isolated compound (I4) can be further purified by chromatography, recrystallization, and others.
The Qol compounds are each known and described, for example, in “THE PESTICIDE MANUAL - 14th EDITION (published by BCPC) ISBN 1901396142” and International Publication No. WO 95/27693. These compounds are formed from commercially available preparations or synthesized by known methods.
In the composition of the present invention, the weight ratio of the pyridazine compound and the Qol compound generally satisfies the pyridazine compound / Qol compound = 0.01 / 1 to 500/1 and preferably 0.1 / 1 to 10/1.
The composition of the present invention can be a mixture of the pyridazine compound and the Qol compound as is; however, the composition of the present invention is generally formulated into a preparation by mixing the pyridazine compound, the Qol compound and an inactive vehicle, optionally adding a surfactant and other preparation aids and preparing an oily solution. , an emulsion, a flowable agent, a wetting powder, a granular wetting powder, a powder, a granule, and others. Such a preparation can be used as an agent for the control of plant diseases, directly or as a mixture with other inactive components.
In the composition of the present invention, the pyridazine compound and the Qol compound are generally contained in a total amount
8/40 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 a solid carrier that is used in the formulation in a preparation include fine powders or grains formed from minerals such as kaolin clay, atapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth and calcite; naturally occurring organic substances such as a corn cob powder and a nutshell flour; synthetic organic substances such as urea; salts such as calcium carbonate and ammonium sulfate; and synthetic inorganic substances such as synthesized silicon oxide containing water. Examples of a liquid carrier include aromatic hydrocarbons such as xylene, alkylbenzene and methylnaphthalene; alcohols such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol monoethyl ether; ketones such as acetone, cyclohexanone and isophorone; vegetable oils such as soybean oil and cottonseed oil; aliphatic hydrocarbons of petroleum, esters, dimethyl sulfoxide, acetonitrile and water.
Examples of a surfactant include anionic surfactants such as an alkyl sulfate, an alkylaryl sulfonate, a dialkyl sulfosuccinate, a polyoxyethylene alkylaryl ether phosphate, a lignin sulfonate and a polycondensate formaldehyde naphthalene sulfonate; nonionic surfactants such as polyoxyethylene alkylaryl ether, a polyoxyethylene alkyl polyoxypropylene block copolymer and a sorbitan fatty acid ester; and cationic surfactants such as an alkyl trimethyl ammonium salt.
Examples of other preparation adjuvants include water-soluble polymers such as polyvinyl alcohol and polyvinyl pyrrolidone; polysaccharides such as arabic gum, alginic acid and a salt thereof, CMC (carboxymethylcellulose) and xanthan gum; inorganic substances such as magnesium aluminum silicate and alumina solution; antiseptic, coloring and stabilizing agents such as PAP (isopropyl acid phosphate) and BHT.
The composition of the present invention can also be prepared by formulating the pyridazine compound and the Qol sepa9 / 40 compound radically in preparations using the aforementioned method, and after that, mixing the preparations or, if necessary, diluting and mixing the dilutions.
The composition of the present invention can be used to protect plants against plant diseases.
Examples of the plant diseases from which plants are effectively controlled by the composition of the present invention include the following.
Rice diseases: explosion (Magnaporthe grisea), leaf spot Helminthosporium (Cochliobolus miyabeanus), plant pest (Rhizoctonia solani) and bakanae disease (Gibberella fujikuroi).
Wheat diseases: powdery mold (Erysiphe graminis), pest of Fusarium plants (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita), mold like pink snow ( Micronectriella nivale), pest of plants such as snow Typhula (Typhula sp.), Loose rust (Ustilago tritici), wheat fungus (Tilletia caries), ocellus (Pseudocercosporella herpotrichoides), leaf blister (Mycosphaerella graminicola), gloom bubble (Stagonospor ), and yellowish brown spot (Pyrenophora tritici-repentis).
Barley diseases: powdery mold (Erysiphe graminis), pest of Fusarium plants (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. hordei), loose rust (Ustilago nuda ), yellowing of the leaves (Rhynchosporium secalis), liquid bubble (Pyrenophora teres), spot bubble (Cochliobolus sativus), leaf stripe (Pyrenophora gramínea), and Rhizoctonia rot (Rhizoctonia solani).
Corn diseases: rust (Ustilago maydis), brown spot (Cochliobolus heterostrophus), copper spot (Gloeocercospora sorghi), southern rust (Puccinia polysora), gray leaf spot (Cercospora zeae-maydis), and Rhizoctonia sol (Rhizoctonia sol) ).
Citrus diseases: melanosis (Diaporthe citri), crust (Elsinoe fawcetti), penicillium rot (Penicillium digitatum, P. italicum), and podri10 / 40 brown (Phytophthora parasitica, Phytophthora citrophthora).
Apple diseases: flower pest (Monilinia mali), cancer (Waltz ceratosperma), powdery mold (Podosphaera leucotricha), leaf spot Alternaria (Alternaria alternata apple patotype), crust (Venturia inaequalis), bitter rot (Colletotrichum acutatum) and crown rot (Phytophtora cactorum).
Pear diseases: crust (Venturia nashicola, V. pirina), black spot (Alternaria alternata Japanese pear pattern), rust (Gymnosporangium haraeanum), and phytophora fruit rot (Phytophthora cactorum).
Peach diseases: brown rot (Monilinia fructicola), crust (Cladosporium carpophilum), and Phomopsis rot (Phomopsis sp.).
Grape diseases: anthracnose (Elsinoe ampelina), ripe rot (Glomerella cingulata), powdery mold (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), and downy mold (Plasmopara viticola).
Japanese persimmon diseases: anthracnose (Gloeosporium kaki) and cercosporiosis (Cercospora kaki, Mycosphaerella nawae).
Gourd diseases: anthracnose (Colletotrichum lagenarium), powdery mold (Sphaerotheca fuliginea), gummy stem plague (Mycosphaerella melonis), Fusarium wilt (Fusarium oxysporum), shaggy mold (Pseudoperonospora cubensis), Phytophora (Phytophthophora) (Phytophthophora) (Phytophthophora). Pythium sp.).
Tomato diseases: early plant pest (Alternaria solani), leaf mold (Cladosporium fulvum) and late plant pest (Phytophthora infestans).
Eggplant diseases: brown spot (Phomopsis vexans) and powdery mold (Erysiphe cichoracearum).
Cruciferous vegetable diseases: Alternaria leaf spot (Alternaria japonica), white spot (Cercosporella brassicae), cruciferous hernia (Plasmodiophora brassicae), and downy mold (Peronospora parasitica).
11/40
Welsh onion diseases: rust (Puccinia allii), and shaggy mold (Peronospora destructor).
Soy diseases: purple seed spot (Cercospora kikuchii), Sphaceloma horse mackerel (Elsinoe glycines), pod pest and stem (Diaporthe phaseolorum var .oyae), Septoriosis brown spot (Septoria glycines), cercosporiosis (Cercospora sojina), (Phakopsora pachyrhizi), brown rot (Phytophthora soye), Rhizoctonia decay (Rhizoctonia solani) Corynespora target spot (Corynespora casiicola), and Sclerotinia rot (Sclerotinia sclerotiorum).
Common bean diseases: anthracnose (Colletotrichum lindemthianum).
Peanut diseases: cercosporiosis (Cercospora personata), brown cercosporiosis (Cercospora arachidicola) and southern pest (Sclerotium rolfsii).
Orchard pea diseases: powdery mold (Erysiphe pisi).
Potato diseases: black spot (Alternaria solani), late plant pest (Phytophthora infestans), pink rot (Phytophthora erythroseptica), and powdery crust (Spongospora underground f. Sp. Underground).
Strawberry diseases: powdery mold (Sphaerotheca humuli), and anthracnose (Glomerella cingulata).
Tea diseases: liquid bubble plague (Exobasidium reticulatum), white crust (Elsinoe leucospila), gray rust (Pestalotiopsis sp.) And anthracnose (Colletotrichum theae-sinensis).
Tobacco diseases: brown spot (Alternaria longipes), powdery mold (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mold (Peronospora tabacina), and black stalk (Phytophthora nicotianae).
Rape diseases: Sclerotinia rot (Sclerotinia sclerotiorum) and Rhizoctonia decay (Rhizoctonia solani).
Cotton diseases: Rhizoctonia decay (Rhizoctonia
12/40 solani).
Sugar beet diseases: Cercospora cercosporiosis (Cercospora beticola), leaf pest (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), and Aphanomyces root rot (Aphanomyces cochlioides).
Diseases of the rose: black spot (Diplocarpon rosae), powdery mold (Sphaerotheca pannosa), and fuzzy mold (Peronospora sparsa).
Chrysanthemum and plant diseases Asteraceae: downy mold (Bremia lactucae), leaf pest (Septoria chrysanthemi-indici), and white rust (Puccinia horiana).
Diseases of various groups: diseases caused by Pythium spp. (Pythium aphanidermatum, Pythium debarianum, Pythium graminicola, Pythium irregulare, Pythium ultimum), gray mold (Botrytis cinerea), Sclerotinia rot (Sclerotinia sclerotiorum).
Japanese radish disease: Alternaria leaf spot (Alternaria brassicicola).
Lawn diseases: dollar spot (Sclerotinia homeocarpa), and brown spot and large spot (Rhizoctonia solani).
Banana disease: sigatoka (Mycosphaerella fijiensis, Mycosphaerella musicola).
Sunflower disease: shaggy mold (Plasmopara halstedii).
Seed diseases or diseases in the early stages of crop plants caused by bacteria, for example, Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor , of the genus Corticium, of the genus Phoma, of the genus Rhizoctonia and of the genus Diplodia.
Viral diseases of culture plants mediated by viruses, for example, of the genus Polymixa or of the genus Olpidium.
Examples of plants to which the composition of the present invention can be applied include the following plants:
Cultures; corn, rice, wheat, barley, rye, oats, sorghum, cotton, soy,
13/40 peanuts, wheat, beets, rapeseed, sunflower, sugar cane, tobacco, etc; Vegetables; soianaceous vegetables (eggplant, tomato, pepper, pepper, potato, etc.), cucurbitaceous vegetables (pumpkin, cucumber, zucchini, watermelon, melon, pumpkin, etc.), cruciferous vegetables (Japanese radish, white turnip, spicy horseradish, kohlrabi , Chinese cabbage, cabbage, leaf mustard, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, crown daisy, artichoke, lettuce, etc.), lily vegetables (green onion, onion, garlic, and asparagus) , amiaceous vegetables (carrot, parsley, celery, turnip, etc.), kenopodiaceous vegetables (spinach, Swiss chard, etc.), llamaaceous vegetables (Perilla frutescens, mint, basil, etc.), strawberry, sweet potato, Dioscorea japonica , colocasia, etc., flowers, foliage, lawns, fruits, orchard fruits (apple, pear, Japanese pear, Chinese quince, quince, etc.), fleshy stone fruits (peach, plum, nectarine, Prunus mume, cherry, apricot, prune, etc.), citrus fruits (Citrus unshiu, orange, lemon, rime, grape, etc.), nuts (chestnuts, walnuts, hazelnuts almonds, pistachios, cashews, macadamia nuts, etc.), soft fruits (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, olive, Japanese plum, banana, coffee, palm, coconuts, etc., trees other than fruit trees, tea, mulberry, flowering plant, roadside trees (fraxino, birch, dogwood, Eucalyptus, Ginkgo biloba, lilac, maple, Quercus, poplar, Judas tree, Liquidambar formosana, maple, zelkova, Japanese arborvitae, fir wood, hemlock, juniper, Pinus, Picea, and Taxus cuspidate), etc.
The aforementioned plants may include plants that have been made resistant by genetic recombination techniques.
Of the above diseases, the diseases that occur in wheat, for which a particularly high control effectiveness is expected.
Of the plant diseases that occur in these crop plants, examples of wheat diseases for which a particularly effective
Elevated 14/40 is expected to include powdery mold (Erysiphe graminis), Fusarium plant pest (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita), mold pink snow (Micronectriella nivale), Typhula pest of snow-like plants (Typhula sp.), loose rust (Ustilago tritici), weevil (Tilletia caries), ocellus (Pseudocercosporella herpotrichoides), leaf blister (Mycosphaerella graminicola), glume bubble (Stc nodorum), and yellow spot (Pyrenophora tritici-repentis).
Examples of the composition of the present invention include the following compositions:
a composition containing the pyridazine compound (1) and dimoxystrobin; a composition containing the pyridazine compound (1) and azoxystrobin; a composition containing the pyridazine compound (1) and fluoxastrobin; a composition containing the pyridazine compound (1) and pyraclostrobin; a composition containing the pyridazine compound (1) and cresoxime-methyl; a composition containing the pyridazine compound (1) and picoxystrobin; a composition containing the pyridazine compound (1) and trifloxystrobin; a composition containing the pyridazine compound (1) and N-methyl-a-methoxyimino-2 - [(2,5-dimethyl-phenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (2) and dimoxystrobin; a composition containing the pyridazine compound (2) and azoxystrobin; a composition containing the pyridazine compound (2) and fluoxastrobin; a composition containing the pyridazine compound (2) and pyraclostrobin; a composition containing the pyridazine compound (2) and cresoxime-methyl; a composition containing the pyridazine compound (2) and picoxystrobin; a composition containing the pyridazine compound (2) and trifloxystrobin; a composition containing the pyridazine compound (2) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (3) and dimoxystrobin; a composition containing the pyridazine compound (3) and azoxystrobin; a composition containing the pyridazine compound (3) and fluoxastrobin; a composition containing the pyridazine compound (3) and pyraclostrobin;
15/40 a composition containing the pyridazine compound (3) and cresoxime-methyl; a composition containing the pyridazine compound (3) and picoxystrobin; a composition containing the pyridazine compound (3) and trifloxystrobin; a composition containing the pyridazine compound (3) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (4) and dimoxystrobin; a composition containing the pyridazine compound (4) and azoxystrobin; a composition containing the pyridazine compound (4) and fluoxastrobin; a composition containing the pyridazine compound (4) and pyraclostrobin; a composition containing the pyridazine compound (4) and cresoxime-methyl; a composition containing the pyridazine compound (4) and picoxystrobin; a composition containing the pyridazine compound (4) and trifloxystrobin; a composition containing the pyridazine compound (4) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (5) and dimoxystrobin;
a composition containing the pyridazine compound (5) and azoxystrobin;
a composition containing the pyridazine compound (5) and fluoxastrobin;
a composition containing the pyridazine compound (5) and pyraclostrobin;
a composition containing the pyridazine compound (5) and cresoxime-methyl; a composition containing the pyridazine compound (5) and picoxystrobin;
a composition containing the pyridazine compound (5) and trifloxystrobin;
a composition containing the pyridazine compound (5) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (6) and dimoxystrobin;
a composition containing the pyridazine compound (6) and azoxystrobin;
a composition containing the pyridazine compound (6) and fluoxastrobin;
a composition containing the pyridazine compound (6) and pyraclostrobin;
a composition containing the pyridazine compound (6) and cresoxime-methyl; a composition containing the pyridazine compound (6) and picoxystrobin;
a composition containing the pyridazine compound (6) and trifloxystrobin;
a composition containing the pyridazine compound (6) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
16/40 a composition containing the pyridazine compound (7) and dimoxystrobin; a composition containing the pyridazine compound (7) and azoxystrobin; a composition containing the pyridazine compound (7) and fluoxastrobin;
a composition containing the pyridazine compound (7) and pyraclostrobin;
a composition containing the pyridazine compound (7) and cresoxime-methyl; a composition containing the pyridazine compound (7) and picoxystrobin;
a composition containing the pyridazine compound (7), and trifloxystrobin;
a composition containing the pyridazine compound (7) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (8) and dimoxystrobin; a composition containing the pyridazine compound (8) and azoxystrobin; a composition containing the pyridazine compound (8) and fluoxastrobin;
a composition containing the pyridazine compound (8) and pyraclostrobin;
a composition containing the pyridazine compound (8) and cresoxime-methyl; a composition containing the pyridazine compound (8) and picoxystrobin;
a composition containing the pyridazine compound (8), and trifloxystrobin;
a composition containing the pyridazine compound (8) and N-methyl-a-methoxyminino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (1) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (1) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (1) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (1) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine (1) compound and pyraclostrobin in a weight ratio that satisfies the pyridazine (1) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (1) / creso17 / 40 xima-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (1) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (1) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine (1) / N-methyl compound -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (2) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (2) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (2) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine (2) compound and pyraclostrobin in a weight ratio that satisfies the pyridazine (2) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (2) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (2) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (2) / trifloxystrobin = 0.1 / 1 to 10/1;
18/40 a composition containing the pyridazine compound (2) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine compound (2) / N-methyl-a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (3) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (3) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (3) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine (3) compound and pyraclostrobin in a weight ratio that satisfies the pyridazine (3) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (3) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (3) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (3) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine (3) / N-methyl compound -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (4) / dimoxystrobin = 0.1 / 1 to 10/1;
19/40 a composition containing the pyridazine compound (4) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (4) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (4) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and pyraclostrobin in a weight ratio that satisfies the pyridazine (4) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (4) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (4) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (4) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine compound (4) / N-methyl -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (5) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (5) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (5) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and pyraclostrobin in
20/40 a weight ratio that satisfies the pyridazine compound (5) / pyraclostrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (5) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (5) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (5) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine compound (5) / N-methyl -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (6) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (6) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (6) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine (6) and pyraclostrobin compound in a weight ratio that satisfies the pyridazine (6) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (6) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (6) / picoxystrobi21 / 40 na = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (6) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine (6) / N-methyl compound -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (7) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (7) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (7) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and pyraclostrobin in a weight ratio that satisfies the pyridazine compound (7) / pyraclostrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (7) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (7) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (7) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine compound (7) / N-methyl -a-methoxyimino-2 - [(2,522 / 40 dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (8) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (8) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine (8) and pyraclostrobin compound in a weight ratio that satisfies the pyridazine (8) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (8) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (8) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (8) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (8) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (8) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (8) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (8) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine (8) / N-methyl compound -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
The plant disease control method of the present invention (hereinafter referred to as the control method of the present invention) is accomplished by applying effective amounts of the pyridazine compound and the Qol compound to a plant or soil for the cultivation of a plant. Examples of such a plant include the stem and leaves of a plant, the seeds of a plant and the bulbs of a plant. Note that the bulb here means a bulb, grain, rhizome, stem tuber, root tuber and rhizophore.
In the control method of the invention, the pyridazine compound and the Qol compound can be applied simultaneously or separately to a plant or to the soil for the cultivation of a plant; however, they are generally applied in the form of the composition of the present invention, in
23/40 consideration of convenience.
In the control method of the invention, as a method for applying the pyridazine compound and the Qol compound, for example, application to the stem and leaves, application to the soil, application to the root and application to the seeds are mentioned.
As the application to the stem and leaves, for example, a method of applying the composition of the present invention to a surface of the plant that is cultivated, by spraying on the stem and leaves and spraying on the trunk, is mentioned.
Like application to the root, for example, a method of saturating an entire plant or the root in a drug solution containing the pyridazine compound and the Qol compound, and a method of binding a solid preparation containing the compound of pyridazine, the Qol compound and a solid vehicle, at the root of a plant, are mentioned.
As the application to the soil, for example, spraying, mixing and irrigating a drug solution to the soil, are mentioned.
As the application of seeds, for example, the application of the composition of the present invention to the seeds or bulbs of the plant to be protected from plant diseases, is mentioned. Specific examples of these include a mist spray application in which a suspension of the composition of the present invention is converted to mist and sprayed to a seed surface or bulb surface, a coating application in which a wetting powder, emulsion or spray agent. flow of the composition of the present invention is spread on the seeds or bulb by adding a small amount of water or directly, saturation application in which the seeds are soaked in a solution of the composition of the present invention for a predetermined time, a coating application film and granule coating application.
In the control method of the invention, the application amounts of the pyridazine compound and the Qol compound vary depending, for example, on the type of plant to be treated, type and frequency of occurrence
24/40 of the plant disease to be controlled, type of preparation, application time, application method, application site and weather conditions. For example, if the above compounds are applied to the stem and leaves of the plant or to the soil for growing a plant, the application amounts, that is, the total amount of the pyridazine compound and the Qol compound, are generally 1 at 500 g, preferably from 2 to 200 g and more preferably from 10 to 100 g per 1000 m2. Furthermore, if applied to the seeds, the application amounts of the pyridazine compound and the Qol compound, that is, the total amount of the pyridazine compound and the Qol compound, is generally 0.001 to 10 g and preferably 0, 01 to 1 g per kg of seeds.
The above emulsion, wetting powder, flowable agent and others are generally diluted with water and then sprayed for treatment. In this case, the concentrations of the pyridazine compound and the Qol compound, that is, the total concentration of the pyridazine compound and the Qol compound, is generally 0.0005 to 2% by weight and preferably 0.005 to 1% by weight. Weight. The above powder, granules, and more are generally applied directly without being diluted.
Examples
The present invention will be further specifically described by way of Preparation Examples and Experimental Examples below; however, the present invention is not limited to the following Examples. Note that, in the following Examples, the parts represent parts by weight unless otherwise specified.
First, the Reference Production Examples of the pyridazine compound to be used in the composition of the present invention will be further described more specifically; however, the present invention is not limited to these Examples.
Reference Production Example 1
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-CH ₃
ΌΗ
CH ₃ (1)
To a mixture of 2-bromopropiophenone (2.13 g), 2.6difluorophenylacetic acid (1.81 g) and acetonitrile (25 ml), triethylamine (1.52 g) was added by dripping in a water bath, stirred in room temperature for 4 hours and then left to stand overnight. At the mixture, 4.57 g of 1,8-diazabicyclo [5.4.0] -7-undecene (hereinafter referred to as DBU) were added by dripping under ice-cooling. The mixture was stirred at room temperature for one hour. Thereafter, to the obtained mixture, air was blown while stirring at room temperature for 5 hours. To the reaction mixture, ice and 1 mol / L hydrochloric acid were added. The mixture was extracted with ethyl acetate. The organic layer was sequentially washed with an aqueous saturated sodium bicarbonate solution and a saturated saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 3 (2,6-difluorophenyl) -5-hydroxy-5 -methyl-4-phenyl-2 (5H) -furanone (2.83 g).
1H-NMR (CDCI3, TMS) δ (ppm): 1.78 (3H, s), 4.07 (1H, br s), 6.77 - 6.85 (1H, br m), 6.96 - 7.08 (1H, m), 7.29 - 7.38 (4H, m), 7.53 - 7.55 (2H, m)
To a mixture of 3- (2,6-difluorophenyl) -5-hydroxy-5-methyl-4-phenyl2 (5H) -furanone (2.83 g) and 1-butanol (15 ml), hydrazine monohydrate (0.60 g) was added by dripping and then stirred in a heated bath of 110 ° C for 2.5 hours. Subsequently, the reaction mixture was cooled to 0 ° C. The resulting solid substance was collected by filtration. The collected solid substance was washed with a solvent mixture of hexane and
26/40 t-butyl methyl ether (1: 1) and dried under reduced pressure to obtain 4- (2,6difluorophenyl) -6-methyl-5-phenyl-2H-pyridazin-3-one (1.70 g) .
1H-NMR (DMSO-d6, TMS) δ (ppm): 2.02 (3H, s), 6.92 - 6.98 (2H, m), 7.11 7.12 (2H, m), 7 , 27 - 7.36 (4H, m), 13.2 (1H, br s)
4- (2,6-Difluorophenyl) -6-methyl-5-phenyl-2H-pyridazin-3-one (1.54 g) and phosphorus oxychloride (10 ml) were mixed and stirred in a 110 ° heated bath C for 1.5 hours. The reaction mixture was allowed to cool to room temperature and then concentrated under reduced pressure. To the residue, ethyl acetate and ice water were added. Thereafter the mixture was separated and the organic layer was sequentially washed with a saturated aqueous sodium bicarbonate solution and a saturated saline solution and dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue (1.55 g) was washed with a mixture of hexane and ethyl acetate solution (10: 1), and subsequently with methyl butyl ether to obtain the pyridazine compound (1) (0.85 g) .
1H-NMR (CDCI3, TMS) δ (ppm): 2.55 (3H, s), 6.79 - 6.83 (2H, m), 7.07 - 7.09 (2H, m), 7, 23 - 7.30 (4H, m)
Reference Production Example 2
(2) (3)
4- (2,6-Difluorophenyl) -6-methyl-5-phenyl-2H-pyridazin-3-one (2.09 g) and phosphorus oxybromide (8.0 g) are mixed and stirred in a heated bath of 85 ° C for 1.5 hours and subsequently in a heated bath of 95 ° C for one hour. The reaction mixture is allowed to cool to room temperature, suspended in ethyl acetate (approximately 20 ml) and poured onto ice (approximately 100 g). After the solution obtained is neutralized with aqueous calcium bicarbonate solution, the residue is extracted with ethyl acetate and separated. The organic layer is washed with a saline solution, dried over anhydrous magnesium sulfate and
27/40 concentrated under reduced pressure. The residue obtained is subjected to column chromatography on silica gel to obtain the pyridazine compound (2).
The pyridazine compound (2) (0.72 g), copper cyanide (0.22 g) and N, N-dimethylacetamide (6 ml) are mixed and stirred under reflux for 3 hours. The reaction mixture is allowed to cool to room temperature, added to ethyl acetate and water (about 50 ml each) and filtered with cerite. The filtrate is separated and the organic layer is washed with a saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained is subjected to column chromatography on silica gel to obtain the pyridazine compound (3). Reference Production Example 3
The pyridazine compound (1) (1.90 g), iron (III) acetylacetonate (0.42 g), tetrahydrofuran (60 ml) and N-methylpyrrolidone (6 ml) are mixed. To this, methylmagnesium bromide (3.0 mol / L of diethyl ether solution) (6 ml) is added while stirring under cooling with ice. To the reaction mixture, a 1 mol / L aqueous hydrochloric acid solution (30 ml) is added by dripping and water is added. After that, the reaction mixture is extracted with ethyl acetate. The organic layer is sequentially washed with an aqueous solution of calcium bicarbonate and a saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained is subjected to column chromatography on silica gel to obtain the pyridazine compound (4).
Reference Production Example 4
(6) (7)
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6-Methyl-5-phenyl-4- (2,4,6-trifluorophenyl) -2H-pyridazin-3-one (2.21 g) and phosphorus oxybromide (8.0 g) are mixed and stirred in a bath heated at 85 ° C for 1.5 hours and subsequently in a heated bath of 95 ° C for one hour. The reaction mixture is allowed to cool to room temperature, suspended in ethyl acetate (around 20 ml) and poured into ice (around 100 g). After the obtained solution is neutralized with aqueous solution of calcium bicarbonate, the residue is extracted with ethyl acetate and separated. The organic layer is washed with a saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained is subjected to column ermatography on silica gel to obtain the pyridazine compound (6) ·
The pyridazine compound (6) (0.76 g), copper cyanide (0.22 g) and N, N-dimethylacetamide (6 ml) are mixed and stirred under reflux for 3 hours. The reaction mixture is allowed to cool to room temperature, added to ethyl acetate and water (around 50 ml each) and filtered with cerite. The filtrate is separated and the organic layer is washed with a saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained is subjected to column chromatography on silica gel to obtain the pyridazine compound (7). Reference Production Example 5

The pyridazine compound (5) (2.01 g), iron (III) acetylacetonate (0.42 g), tetrahydrofuran (60 ml) and N-methylpyrrolidone (6 ml) are mixed. To this, methylmagnesium bromide (3.0 mol / L diethyl ether solution) (6 ml) is added while stirring under cooling with ice. To the reaction mixture, an aqueous hydrochloric acid solution (30 ml) is added by dripping and water is added. The reaction mixture is then extracted
29/40 with ethyl acetate. The organic layer is sequentially washed with an aqueous solution of calcium bicarbonate and a saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained is subjected to column chromatography on silica gel to obtain the pyridazine compound (8).
Preparation Example 1
Each of the pyridazine compounds from (1) to (8) (2.5 parts), dimoxystrobin (1.25 part), polyoxyethylene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76, 25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 2
Each of the pyridazine compounds from (1) to (8) (2.5 parts), azoxystrobin (1.25 part), polyoxyethylene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76, 25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 3
Each of the pyridazine compounds from (1) to (8) (2.5 parts), phyoxastrobin (1.25 part), polyoxyethylene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76, 25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 4
Each of the pyridazine compounds of (1) to (8) (2.5 parts), pyraclostrobin (1.25 part), polyoxyethylene phenyl ether (14 parts), calcium dodecyl benzene sulfonate (6 parts) and xylene (76, 25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 5
Each of the pyridazine compounds from (1) to (8) (2.5 parts), cresoxime-methyl (1.25 part), polyoxyethylene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene ( 76.25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 6
Each of the pyridazine compounds from (1) to (8) (2.5 parts),
30/40 picoxystrobin (1.25 part), polyoxyethylene styrene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76.25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 7
Each of the pyridazine compounds from (1) to (8) (2.5 parts), trifloxystrobin (1.25 part), phenyl polyoxyethylene ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76, 25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 8
Each of the pyridazine compounds from (1) to (8) (2.5 parts), N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide (1.25 part) , polyoxyethylene styrene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76.25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 9
Each of the pyridazine compounds from (1) to (8) (2 parts), dimoxystrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
Preparation Example 10
Each of the pyridazine compounds from (1) to (8) (2 parts), azoxystrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
Preparation Example 11
Each of the pyridazine compounds from (1) to (8) (2 parts), fluoxastrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
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Preparation Example 12
Each of the pyridazine compounds from (1) to (8) (2 parts), pyraclostrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
Preparation Example 13
Each of the pyridazine compounds from (1) to (8) (2 parts), cresoxime-methyl (8 parts), a mixture of white carbon and ammonium sulfate salt of polyoxyethylene alkyl ether (in a weight ratio of 1 : 1) (35 parts) and water (55 parts) are mixed and finely ground by a wet grinding method. In this way, the preparations are obtained.
Preparation Example 14
Each of the pyridazine compounds from (1) to (8) (2 parts), picoxystrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
Preparation Example 15
Each of the pyridazine compounds from (1) to (8) (2 parts), trifloxystrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
Preparation Example 16
Each of the pyridazine compounds from (1) to (8) (2 parts), N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide (8 parts), a mixture of white carbon and ammonium sulfate salt of polyoxyethylene alkyl ether (in a 1: 1 weight ratio) (35 parts) and water (55 parts) are mixed and finely ground by a wet grinding method. In this way, the preparations are obtained.
Preparation Example 17
32/40
Each of the pyridazine compounds from (1) to (8) (5 parts), dimoxystrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 18
Each of the pyridazine compounds from (1) to (8) (5 parts), azoxystrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 19
Each of the pyridazine compounds from (1) to (8) (5 parts), fiuoxastrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 20
Each of the pyridazine compounds from (1) to (8) (5 parts), pyraclostrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts) ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and sili33 / 40 magnesium aluminum cate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred . In this way, the preparations are obtained.
Preparation Example 21
Each of the pyridazine compounds from (1) to (8) (5 parts), cresoxime-methyl (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol ( 2 parts) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 22
Each of the pyridazine compounds from (1) to (8) (5 parts), picoxystrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 23
Each of the pyridazine compounds from (1) to (8) (5 parts), trifloxystrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained. Preparation Example 24
Each of the pyridazine compounds from (1) to (8) (5 parts), N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide (10 parts),
34/40 sorbitan trioleate (1.5 parts) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 25
Each of the pyridazine compounds from (1) to (8) (1 part), dimoxystrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 26
Each of the pyridazine compounds from (1) to (8) (1 part), azoxystrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 27
Each of the pyridazine compounds from (1) to (8) (1 part), fluoxastrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 28
Each of the pyridazine compounds from (1) to (8) (1 part), pyraclostrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. THE
35/40 mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 29
Each of the pyridazine compounds from (1) to (8) (1 part), cresoxime methyl (4 parts), synthesized silicon oxide containing water (1 part), calcium iigninosulfonate (2 parts), bentonite (30 parts ) and kaolin clay (62 parts) are crushed and well mixed. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 30
Each of the pyridazine compounds from (1) to (8) (1 part), picoxystrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium iignosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 31
Each of the pyridazine compounds from (1) to (8) (1 part), trifloxystrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium iignosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 32
Each of the pyridazine compounds from (1) to (8) (1 part), Nmethyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide (4 parts), synthesized silicon oxide containing water (1 part), calcium iignosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained. Preparation Example 33
Each of the pyridazine compounds from (1) to (8) (12.5 par36 / 40 tes), cresoxime-methyl (37.5 parts), calcium ligninosulfonate (3 parts), sodium lauryl sulfate (2 parts) and synthesized silicon oxide containing water (45 parts) are crushed and mixed well. In this way, the preparations are obtained.
Preparation Example 34
Each of the pyridazine compounds from (1) to (8) (3 parts), azoxystrobin (2 parts), kaolin clay (85 parts) and talc (10 parts) are crushed and mixed well. In this way, the preparations are obtained.
In the following, the experimental examples will be described.
Experimental Example 1
A plastic pot was loaded with soil. In the soil, wheat seeds (cultivar; Apogee) were sown and cultivated for 14 days in a greenhouse. A test compound was dissolved in a CEC cocktail (cidohexanone: Sorpol (trademark), 2680X (manufactured by TOHO Chemical Industry Co., Ltd.) = 5: 1 (volume ratio)) to make a preparation. After that, the preparation was diluted with water to a predetermined concentration. The diluted solution was sprayed onto the stem and leaves in such a way that the diluted solution was sufficiently bound to the surfaces of the wheat leaves. After spraying, the plant was dried with air. Two days later, an aqueous suspension (about 1,000,000 / ml) containing conidia spores from the wheat leaf spot (Mycosphaerella graminicola) was sprayed to inoculate the spores. After completion of inoculation, the plant was allowed to swell first in a high humidity location at 18 oC for 3 days and then the plant was removed from the site in high humidity and transferred to an 18 oC thermostatic chamber for 14 days. In this way, the wheat was grown (this is referred to as a treatment zone). After that, the damaged area of the wheat leaf spot was checked.
On the other hand, wheat was grown in the same way as in the treatment zone, except that a diluted solution of a test compound was not sprayed on the stem and leaves (this is referred to as a non-treatment zone). The damaged area of the wheat leaf spot was evaluated in the same way as in the treatment zone.
37/40
From the injured areas of the treatment zone and the non-treatment zone, the effectiveness of the treatment zone was obtained according to the following expression (1). The results are shown in [Table 1] through [Table 8].
Effectiveness (%) = (1 - Injured area of the treatment zone) x 100
Injured area of the non-treatment zone
Expression (1) [Table 1]
The pyridazine compound (1) [pm] Azoxystrobin[PPm] Efficiency (%) 3.1 3.1 100
[Table 2]
The pyridazine compound (5) [PPm] Azoxystrobin[Ppm] Efficiency (%) 3.1 3.1 100
[Table 3]
The pyridazine compound (1) [PPm] N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide[PPm] Efficiency(%) 3.1 13 100
[Table 4]
The pyridazine compound (5) [PPm] N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide[pm] Efficiency(%) 3.1 13 100
[Table 5]
The pyridazine compound (1) [PPm] Pyraclostrobin[pm] Efficiency (%) 3.1 3.1 100
[Table 6]
The pyridazine compound (5) [pm] Pyraclostrobin[PPm] Efficiency (%) 3.1 3.1 100
38/40 [Table 7]
The pyridazine compound (1) [PPm] Picoxystrobin[PPm] Efficiency (%) 3.1 3.1 100
[Table 8]
The pyridazine compound (5) [PPm] Picoxystrobin[pm] Efficiency (%) 3.1 3.1 100
Experimental Example 2
Through the use of a rotary seed processor (sowing, manufactured by Hans-UIrich Hege GmbH), a solution of cyclohexanone (100 pl) containing a predetermined weight of a test compound was greased on the wheat seeds (cultivar; Shirogane) ( 10 g) naturally infected with pink snow mold spores (Microdochium nivale).
One day after treatment, a plastic pot was loaded with soil and the seeds treated with the test compound were sown in the soil and grown in a glass greenhouse for 20 days (this is referred to as a treatment zone). After that, the seedlings obtained from individual seeds by germination were observed in relation to the onset of pink snow mold and a disease incidence rate was obtained according to the following expression (2).
On the other hand, wheat seeds not treated with the aforementioned cover treatment were grown in the same way as in the treatment zone (this is referred to as a non-treatment zone). A disease incidence rate was obtained in the same way as in the treatment zone.
As a result, the incidence rate of seedlings obtained from germinated wheat seeds and treated with the composition of the present invention was lower than that of seedlings in the non-treatment zone.
From the incidence rates of the treatment zone and the non-treatment zone, the effectiveness in the treatment zone was obtained according to the following expression (1). The results are shown in [Table 9] through [Table 12].
Incidence rate (%) = (1 - Number of initial seedlings) x 100
Total number of seedlings
Expression (2)
Effectiveness (%) = (1 - Treatment zone incidence rate) x 100
Incidence rate of the non-treatment zone Expression (3) [Table 9]
The pyridazine compound (1)[g / 100 kg of seeds] N-methyl-a-methoxy-imino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide [g / 100 kg of seeds] Efficiency(%) 5 5 100
[Table 10]
The pyridazine compound (5)[g / 100 kg of seeds] N-methyl-a-methoxy-imino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide [g / 100 kg of seeds] Efficiency(%) 5 5 100
[Table 11]
The pyridazine compound (1)[g / 100 kg of seeds] Azoxystrobin [g / 100 kg of seeds] Efficiency (%) 5 1 100
[Table 12]
The pyridazine compound (5)[g / 100 kg of seeds] Azoxystrobin [g / 100 kg of seeds] Efficiency (%) 5 1 100
Experimental Example 3
Through the use of a rotary seed processor (seed15, manufactured by Hans-UIrich Hege GmbH), a solution of cyclohexanone (100 μΙ) containing a predetermined weight of a test compound was greased on the wheat seeds (cultivar; Shirogane) (10 g) Naturally 40/40 infected with pink snow mold spores (Microdochium nivale).
One day after treatment, a plastic pot was loaded with soil and the seeds treated with the test compound were sown in the soil and grown in a glass greenhouse for 20 days (this is referred to as a treatment zone). After that, the seedlings obtained from individual seeds by germination were observed in relation to the onset of pink snow mold and a disease incidence rate was obtained according to the following expression (2).
On the other hand, wheat seeds not treated with the aforementioned cover treatment were grown in the same way as in the treatment zone (this is referred to as a non-treatment zone). A disease incidence rate was obtained in the same way as in the treatment zone.
As a result, the incidence rate of seedlings obtained from germinated wheat seeds and treated with the composition of the present invention was lower than that of seedlings in the non-treatment zone.
Incidence rate (%) = (1 - Number of initial seedlings) x 100
Total number of seedlings
Expression (2)
1/2

权利要求:
Claims (5)
[1]
1. Plant disease control composition, characterized by the fact that it comprises a pyridazine compound represented by formula (I):
5 where
R ¹ represents a chlorine atom, and R ² represents a hydrogen atom, and a Qol compound selected from Group (A).
A group):
10 a group consisting of dimoxystrobin, azoxystrobin, fluoxastrobin, pyraclostrobin, famoxadone, cresoxymethyl, picoxystrobin, trifloxystrobin, N-methyl-a-methoxy-imino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide and phenamidone.
2. Plant disease control composition according to
15 with claim 1, characterized in that a weight ratio of the pyridazine compound and the Qol compound satisfies the pyridazine compound / Qol compound = 0.1 / 1 to 10/1.
3. Method for the control of plant diseases, characterized by the fact that it comprises a step of applying effective amounts of a pyridazine compound represented by formula (I):
on what
R ¹ represents a chlorine atom, and R ² represents a hydrogen atom, and a Qol compound selected from Group (A) in a plant or soil for the growth of a plant,
Petition 870180052670, dc 19/06/2018, p. 4/9
2/2
A group):
a group consisting of dimoxystrobin, azoxystrobin, fiuoxastrobin, pyraclostrobin, famoxadone, crespoxyl, picoxystrobin, trifloxystrobin, N-methyl-a-methoxy-imino-2 - [(2,55 dimethylphenoxy) methyl] phenylacetamide and phenamidone.
4. Plant disease control method according to claim 3, characterized in that a weight ratio of the pyridazine compound and the Qol compound satisfies the pyridazine compound / the Qol compound = 0.1 / 1 to 10/1.
10 5. Method for controlling plant diseases according to claim 3 or 4, characterized by the fact that the plant or soil for growing a plant is wheat or soil for growing wheat.
Petition 870180052670, of 19/06/2018, p. 5/9
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Descriptive Report of the Invention Patent for COMPOSITION AND METHOD OF CONTROL OF PLANT DISEASES UNDERSTANDING A PYRIDAZINE COMPOUND.
TECHNICAL FIELD
The present invention relates to a plant disease control composition and its use.
PREVIOUS TECHNIQUE
Conventionally, many compounds to control plant diseases have been developed and put to practical use (see, for example, Patent Literature 1, Patent Literature 2).
LIST OF QUOTES
PATENT LITERATURE
Patent literature 1: International Publication No. WO 2005/121104.
Patent literature 2: International Publication No. WO 2006/001175.
SUMMARY OF THE INVENTION TECHNICAL PROBLEM
An object of the present invention is to provide a composition having excellent efficacy in the control of plant diseases.
SOLUTION TO THE PROBLEM
The present invention mainly provides a plant disease control composition containing a pyridazine compound represented by the following formula (I) and at least one Qol compound selected from the group (A) below. The composition has an excellent effectiveness in the control of plant diseases.
More specifically, the present invention is as follows.
[1] A plant disease control composition, containing a pyridazine compound represented by formula (I):
03/13/2018, p. 16/23
2/40
Η * where
R1 represents a chlorine atom, a bromine atom, a cyano group or a methyl group, and
R2 represents a hydrogen atom or a fluorine atom, and at least one Qol compound selected from Group (A).
A group):
A group consisting of dimoxystrobin, azoxystrobin, fluoxastrobin, pyraclostrobin, famoxadone, cresoxymethyl, picoxystrobin, trifloxystrobin, N-methyl-a-methoxy-imino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide and phenamidone.
[2]
[2] The plant disease control composition according to [1], wherein the weight ratio of the pyridazine compound and the Qol compound satisfies the pyridazine compound / Qol compound = 0.1 / 1 a 10/1.
[3]
[3] A method for the control of plant diseases, including the step of applying effective amounts of a pyridazine compound represented by formula (I):
on what
R1 represents a chlorine atom, a bromine atom, a cyano group or a methyl group, and
R2 represents a hydrogen atom or a fluorine atom, and at least one Qol compound selected from Group (A) in a plant or soil for the growth of a plant.
A group):
A group consisting of dimoxystrobin, azoxystrobin, fluoxastrobin, pyraclostrobin, famoxadone, cresoxymethyl, picoxystrobin, trifloxystrobin, N-methyl-a-methoxy-imino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide and phenamidone.
[4]
[4] The plant disease control method according to [3], where
3/40 the weight ratio of the pyridazine compound and the Qol compound satisfies the pyridazine compound / Qol compound = 0.1 / 1 to 10/1.
[5]
[5] The method for controlling plant diseases according to [3] or [4], where the plant or soil for growing a plant is wheat or soil for growing wheat.
ADVANTAGE EFFECTS OF THE INVENTION
Plant diseases can be controlled by the present invention.
DESCRIPTION OF MODALITIES
The plant disease control composition of the present invention (hereinafter referred to as the composition of the present invention) contains a pyridazine compound represented by formula (I):
on what
R1 represents a chlorine atom, a bromine atom, a cyano group or a methyl group, and
R2 represents a hydrogen atom or a fluorine atom (hereinafter referred to as the pyridazine compound), and at least one Qol compound (hereinafter referred to as the Qol compound) selected from Group (A).
A group):
A group consisting of dimoxystrobin, azoxystrobin, fluoxastrobin, pyraclostrobin, famoxadone, cresoxymethyl, picoxystrobin, trifloxystrobin, N-methyl-a-methoxy-imino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide and phenamidone.
Examples of the pyridazine compound to be used in the composition of the present invention include the following pyridazine compounds: a pyridazine compound represented by formula (I) wherein R1 is a chlorine atom or a methyl group;
4/40 a pyridazine compound represented by formula (I) wherein R1 is a chlorine atom;
a pyridazine compound represented by formula (I) wherein R1 is a methyl group;
a pyridazine compound represented by formula (I) wherein R1 is a cyano group;
a pyridazine compound represented by formula (I) in which
R2 is a hydrogen atom;
a pyridazine compound represented by formula (I) in which
R2 is a fluorine atom;
a pyridazine compound represented by formula (I) in which R1 is a chlorine atom or a methyl group and R2 is a hydrogen atom; and a pyridazine compound represented by formula (I) in which R1 is a chlorine atom or a methyl group and R2 is a fluorine atom.
Specific examples of the pyridazine compound include the following compounds:
a pyridazine compound represented by formula (I) where R1 is a chlorine atom and R2 is a hydrogen atom (hereinafter referred to as the pyridazine compound (1));
a pyridazine compound represented by formula (I) wherein R1 is a bromine atom and R2 is a hydrogen atom (hereinafter referred to as the pyridazine compound (2));
a pyridazine compound represented by formula (I) where R1 is a group and cyano and R2 is a hydrogen atom (hereinafter referred to as the pyridazine compound (3));
a pyridazine compound represented by formula (I) where R1 is a methyl group and R2 is a hydrogen atom (hereinafter referred to as the pyridazine compound (4));
a pyridazine compound represented by formula (I) wherein R1 is a chlorine atom and R2 is a fluorine atom (hereinafter referred to as the pyridazine compound (5));
a pyridazine compound represented by formula (I) where R1 is a
5/40 bromine atom and R2 is a fluorine atom (hereinafter referred to as the pyridazine compound (6));
a pyridazine compound represented by formula (I) wherein R1 is a cyano group and R2 is a fluorine atom (hereinafter referred to as the pyridazine compound (7)); and a pyridazine compound represented by formula (I) where R1 is a methyl group and R2 is a fluorine atom (hereinafter referred to as the pyridazine compound (8)).
Of the pyridazine compounds, the pyridazine compound represented by formula (I) wherein R1 is a chlorine atom or a bromine atom can be produced by a method described, for example, in International Publication No. WO 2005/121104.
Of the pyridazine compounds, the pyridazine compound represented by formula (I) in which R1 is a methyl group can be produced by a method described, for example, in International Publication No. WO 2006/001175.
Of the pyridazine compounds, a compound (I-2) represented by the formula (I) in which R1 is a cyano group can be produced by reacting, for example, a compound (1-1) represented by the formula (I) in that R1 is a bromine atom among copper cyanide pyridazine compounds.
The reaction is usually carried out in the presence of a solvent. As the solvent to be used in the reaction, for example, a polar aprotic solvent such as Ν, Ν-dimethylacetamide is mentioned.
The amount of copper cyanide to be used in the reaction is usually 1 to 1.5 mol with respect to 1 mol of the compound (1-1) through the
6/40 reason.
The reaction temperature of the reaction generally falls within the range of 120 to 180 oC and the reaction time generally falls within the range of 1 to 24 hours.
After completion of the reaction, for example, the reaction mixture is mixed with water and an organic solvent and filtered. After the filtrate is separated, the obtained organic layer is further washed with water, dried and concentrated. Through these operations, the compound (I-2) can be isolated. The isolated compound (I-2) can be further purified by chromatography, recrystallization, and others.
Of the pyridazine compounds, a pyridazine compound (I-4) represented by the formula (I) in which R1 is a methyl group can be produced by reacting a pyridazine compound (I-3) in which R1 is an atom chlorine between pyridazine compounds with a Grignard reagent represented by formula (II):
CH3-MgX (II) where X represents a bromine atom or a chlorine atom in the presence of an iron catalyst.
The reaction is usually carried out in the presence of a solvent. As the solvent to be used in the reaction, for example, tetrahydrofuran, diethyl ether and N-methylpyrrolidone and a mixture of these are mentioned. In the case where the reaction solvent is a mixture of tetrahydrofuran and N-methylpyrrolidone, the mixing ratio (volume ratio) from tetrahydrofuran to N-methylpyrrolidone generally falls within the range of 30: 1 to 3: 1.
As the iron catalyst to be used in the reaction, for example 7/40 pio, iron (III) acetylacetonate and iron (III) chloride are mentioned. The amount of iron catalyst to be used is generally 0.01 to 0.3 mol with respect to 1 mol of the compound (I-3) through the ratio.
The reaction temperature of the reaction generally falls within the range of -20 oC to 30 oC and the reaction time generally falls within the range of 0.1 to 6 hours.
After completion of the reaction, for example, the reaction mixture is mixed with hydrochloric acid and extracted with an organic solvent. The obtained organic layer is washed with water, dried and concentrated. Through these operations, the compound (I-4) can be isolated. The isolated compound (I4) can be further purified by chromatography, recrystallization, and others.
The Qol compounds are each known and described, for example, in “THE PESTICIDE MANUAL - 14th EDITION (published by BCPC) ISBN 1901396142” and International Publication No. WO 95/27693. These compounds are formed from commercially available preparations or synthesized by known methods.
In the composition of the present invention, the weight ratio of the pyridazine compound and the Qol compound generally satisfies the pyridazine compound / Qol compound = 0.01 / 1 to 500/1 and preferably 0.1 / 1 to 10/1.
The composition of the present invention can be a mixture of the pyridazine compound and the Qol compound as is; however, the composition of the present invention is generally formulated into a preparation by mixing the pyridazine compound, the Qol compound and an inactive vehicle, optionally adding a surfactant and other preparation aids and preparing an oily solution. , an emulsion, a flowable agent, a wetting powder, a granular wetting powder, a powder, a granule, and others. Such a preparation can be used as an agent for the control of plant diseases, directly or as a mixture with other inactive components.
In the composition of the present invention, the pyridazine compound and the Qol compound are generally contained in a total amount
8/40 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 a solid carrier that is used in the formulation in a preparation include fine powders or grains formed from minerals such as kaolin clay, atapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth and calcite; naturally occurring organic substances such as a corn cob powder and a nutshell flour; synthetic organic substances such as urea; salts such as calcium carbonate and ammonium sulfate; and synthetic inorganic substances such as synthesized silicon oxide containing water. Examples of a liquid carrier include aromatic hydrocarbons such as xylene, alkylbenzene and methylnaphthalene; alcohols such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol monoethyl ether; ketones such as acetone, cyclohexanone and isophorone; vegetable oils such as soybean oil and cottonseed oil; aliphatic hydrocarbons of petroleum, esters, dimethyl sulfoxide, acetonitrile and water.
Examples of a surfactant include anionic surfactants such as an alkyl sulfate, an alkylaryl sulfonate, a dialkyl sulfosuccinate, a polyoxyethylene alkylaryl ether phosphate, a lignin sulfonate and a polycondensate formaldehyde naphthalene sulfonate; nonionic surfactants such as polyoxyethylene alkylaryl ether, a polyoxyethylene alkyl polyoxypropylene block copolymer and a sorbitan fatty acid ester; and cationic surfactants such as an alkyl trimethyl ammonium salt.
Examples of other preparation adjuvants include water-soluble polymers such as polyvinyl alcohol and polyvinyl pyrrolidone; polysaccharides such as arabic gum, alginic acid and a salt thereof, CMC (carboxymethylcellulose) and xanthan gum; inorganic substances such as magnesium aluminum silicate and alumina solution; antiseptic, coloring and stabilizing agents such as PAP (isopropyl acid phosphate) and BHT.
The composition of the present invention can also be prepared by formulating the pyridazine compound and the Qol sepa9 / 40 compound radically in preparations using the aforementioned method, and after that, mixing the preparations or, if necessary, diluting and mixing the dilutions.
The composition of the present invention can be used to protect plants against plant diseases.
Examples of the plant diseases from which plants are effectively controlled by the composition of the present invention include the following.
Rice diseases: explosion (Magnaporthe grisea), leaf spot Helminthosporium (Cochliobolus miyabeanus), plant pest (Rhizoctonia solani) and bakanae disease (Gibberella fujikuroi).
Wheat diseases: powdery mold (Erysiphe graminis), pest of Fusarium plants (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita), mold like pink snow ( Micronectriella nivale), pest of plants such as snow Typhula (Typhula sp.), Loose rust (Ustilago tritici), wheat fungus (Tilletia caries), ocellus (Pseudocercosporella herpotrichoides), leaf blister (Mycosphaerella graminicola), gloom bubble (Stagonospor ), and yellowish brown spot (Pyrenophora tritici-repentis).
Barley diseases: powdery mold (Erysiphe graminis), pest of Fusarium plants (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. hordei), loose rust (Ustilago nuda ), yellowing of the leaves (Rhynchosporium secalis), liquid bubble (Pyrenophora teres), spot bubble (Cochliobolus sativus), leaf stripe (Pyrenophora gramínea), and Rhizoctonia rot (Rhizoctonia solani).
Corn diseases: rust (Ustilago maydis), brown spot (Cochliobolus heterostrophus), copper spot (Gloeocercospora sorghi), southern rust (Puccinia polysora), gray leaf spot (Cercospora zeae-maydis), and Rhizoctonia sol (Rhizoctonia sol) ).
Citrus diseases: melanosis (Diaporthe citri), crust (Elsinoe fawcetti), penicillium rot (Penicillium digitatum, P. italicum), and podri10 / 40 brown (Phytophthora parasitica, Phytophthora citrophthora).
Apple diseases: flower pest (Monilinia mali), cancer (Waltz ceratosperma), powdery mold (Podosphaera leucotricha), leaf spot Alternaria (Alternaria alternata apple patotype), crust (Venturia inaequalis), bitter rot (Colletotrichum acutatum) and crown rot (Phytophtora cactorum).
Pear diseases: crust (Venturia nashicola, V. pirina), black spot (Alternaria alternata Japanese pear pattern), rust (Gymnosporangium haraeanum), and phytophora fruit rot (Phytophthora cactorum).
Peach diseases: brown rot (Monilinia fructicola), crust (Cladosporium carpophilum), and Phomopsis rot (Phomopsis sp.).
Grape diseases: anthracnose (Elsinoe ampelina), ripe rot (Glomerella cingulata), powdery mold (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), and downy mold (Plasmopara viticola).
Japanese persimmon diseases: anthracnose (Gloeosporium kaki) and cercosporiosis (Cercospora kaki, Mycosphaerella nawae).
Gourd diseases: anthracnose (Colletotrichum lagenarium), powdery mold (Sphaerotheca fuliginea), gummy stem plague (Mycosphaerella melonis), Fusarium wilt (Fusarium oxysporum), shaggy mold (Pseudoperonospora cubensis), Phytophora (Phytophthophora) (Phytophthophora) (Phytophthophora). Pythium sp.).
Tomato diseases: early plant pest (Alternaria solani), leaf mold (Cladosporium fulvum) and late plant pest (Phytophthora infestans).
Eggplant diseases: brown spot (Phomopsis vexans) and powdery mold (Erysiphe cichoracearum).
Cruciferous vegetable diseases: Alternaria leaf spot (Alternaria japonica), white spot (Cercosporella brassicae), cruciferous hernia (Plasmodiophora brassicae), and downy mold (Peronospora parasitica).
11/40
Welsh onion diseases: rust (Puccinia allii), and shaggy mold (Peronospora destructor).
Soy diseases: purple seed spot (Cercospora kikuchii), Sphaceloma horse mackerel (Elsinoe glycines), pod pest and stem (Diaporthe phaseolorum var .oyae), Septoriosis brown spot (Septoria glycines), cercosporiosis (Cercospora sojina), (Phakopsora pachyrhizi), brown rot (Phytophthora soye), Rhizoctonia decay (Rhizoctonia solani) Corynespora target spot (Corynespora casiicola), and Sclerotinia rot (Sclerotinia sclerotiorum).
Common bean diseases: anthracnose (Colletotrichum lindemthianum).
Peanut diseases: cercosporiosis (Cercospora personata), brown cercosporiosis (Cercospora arachidicola) and southern pest (Sclerotium rolfsii).
Orchard pea diseases: powdery mold (Erysiphe pisi).
Potato diseases: black spot (Alternaria solani), late plant pest (Phytophthora infestans), pink rot (Phytophthora erythroseptica), and powdery crust (Spongospora underground f. Sp. Underground).
Strawberry diseases: powdery mold (Sphaerotheca humuli), and anthracnose (Glomerella cingulata).
Tea diseases: liquid bubble plague (Exobasidium reticulatum), white crust (Elsinoe leucospila), gray rust (Pestalotiopsis sp.) And anthracnose (Colletotrichum theae-sinensis).
Tobacco diseases: brown spot (Alternaria longipes), powdery mold (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mold (Peronospora tabacina), and black stalk (Phytophthora nicotianae).
Rape diseases: Sclerotinia rot (Sclerotinia sclerotiorum) and Rhizoctonia decay (Rhizoctonia solani).
Cotton diseases: Rhizoctonia decay (Rhizoctonia
12/40 solani).
Sugar beet diseases: Cercospora cercosporiosis (Cercospora beticola), leaf pest (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), and Aphanomyces root rot (Aphanomyces cochlioides).
Diseases of the rose: black spot (Diplocarpon rosae), powdery mold (Sphaerotheca pannosa), and fuzzy mold (Peronospora sparsa).
Chrysanthemum and plant diseases Asteraceae: downy mold (Bremia lactucae), leaf pest (Septoria chrysanthemi-indici), and white rust (Puccinia horiana).
Diseases of various groups: diseases caused by Pythium spp. (Pythium aphanidermatum, Pythium debarianum, Pythium graminicola, Pythium irregulare, Pythium ultimum), gray mold (Botrytis cinerea), Sclerotinia rot (Sclerotinia sclerotiorum).
Japanese radish disease: Alternaria leaf spot (Alternaria brassicicola).
Lawn diseases: dollar spot (Sclerotinia homeocarpa), and brown spot and large spot (Rhizoctonia solani).
Banana disease: sigatoka (Mycosphaerella fijiensis, Mycosphaerella musicola).
Sunflower disease: shaggy mold (Plasmopara halstedii).
Seed diseases or diseases in the early stages of crop plants caused by bacteria, for example, Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor , of the genus Corticium, of the genus Phoma, of the genus Rhizoctonia and of the genus Diplodia.
Viral diseases of culture plants mediated by viruses, for example, of the genus Polymixa or of the genus Olpidium.
Examples of plants to which the composition of the present invention can be applied include the following plants:
Cultures; corn, rice, wheat, barley, rye, oats, sorghum, cotton, soy,
13/40 peanuts, wheat, beets, rapeseed, sunflower, sugar cane, tobacco, etc; Vegetables; soianaceous vegetables (eggplant, tomato, pepper, pepper, potato, etc.), cucurbitaceous vegetables (pumpkin, cucumber, zucchini, watermelon, melon, pumpkin, etc.), cruciferous vegetables (Japanese radish, white turnip, spicy horseradish, kohlrabi , Chinese cabbage, cabbage, leaf mustard, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, crown daisy, artichoke, lettuce, etc.), lily vegetables (green onion, onion, garlic, and asparagus) , amiaceous vegetables (carrot, parsley, celery, turnip, etc.), kenopodiaceous vegetables (spinach, Swiss chard, etc.), llamaaceous vegetables (Perilla frutescens, mint, basil, etc.), strawberry, sweet potato, Dioscorea japonica , colocasia, etc., flowers, foliage, lawns, fruits, orchard fruits (apple, pear, Japanese pear, Chinese quince, quince, etc.), fleshy stone fruits (peach, plum, nectarine, Prunus mume, cherry, apricot, prune, etc.), citrus fruits (Citrus unshiu, orange, lemon, rime, grape, etc.), nuts (chestnuts, walnuts, hazelnuts almonds, pistachios, cashews, macadamia nuts, etc.), soft fruits (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, olive, Japanese plum, banana, coffee, palm, coconuts, etc., trees other than fruit trees, tea, mulberry, flowering plant, roadside trees (fraxino, birch, dogwood, Eucalyptus, Ginkgo biloba, lilac, maple, Quercus, poplar, Judas tree, Liquidambar formosana, maple, zelkova, Japanese arborvitae, fir wood, hemlock, juniper, Pinus, Picea, and Taxus cuspidate), etc.
The aforementioned plants may include plants that have been made resistant by genetic recombination techniques.
Of the above diseases, the diseases that occur in wheat, for which a particularly high control effectiveness is expected.
Of the plant diseases that occur in these crop plants, examples of wheat diseases for which a particularly effective
Elevated 14/40 is expected to include powdery mold (Erysiphe graminis), Fusarium plant pest (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita), mold pink snow (Micronectrielia nivale), Typhula pest of snow-like plants (Typhula sp.), loose rust (Ustilago tritici), weevil (Tilletia caries), ocellus (Pseudocercosporella herpotrichoides), leaf blister (Mycosphaerella graminicola), glume bubble (Stc nodorum), and yellow spot (Pyrenophora tritici-repentis).
Examples of the composition of the present invention include the following compositions:
a composition containing the pyridazine compound (1) and dimoxystrobin; a composition containing the pyridazine compound (1) and azoxystrobin; a composition containing the pyridazine compound (1) and fluoxastrobin; a composition containing the pyridazine compound (1) and pyraclostrobin; a composition containing the pyridazine compound (1) and cresoxime-methyl; a composition containing the pyridazine compound (1) and picoxystrobin; a composition containing the pyridazine compound (1) and trifloxystrobin; a composition containing the pyridazine compound (1) and N-methyl-a-methoxyimino-2 - [(2,5-dimethyl-phenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (2) and dimoxystrobin; a composition containing the pyridazine compound (2) and azoxystrobin; a composition containing the pyridazine compound (2) and fluoxastrobin; a composition containing the pyridazine compound (2) and pyraclostrobin; a composition containing the pyridazine compound (2) and cresoxime-methyl; a composition containing the pyridazine compound (2) and picoxystrobin; a composition containing the pyridazine compound (2) and trifloxystrobin; a composition containing the pyridazine compound (2) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (3) and dimoxystrobin; a composition containing the pyridazine compound (3) and azoxystrobin; a composition containing the pyridazine compound (3) and fluoxastrobin; a composition containing the pyridazine compound (3) and pyraclostrobin;
15/40 a composition containing the pyridazine compound (3) and cresoxime-methyl; a composition containing the pyridazine compound (3) and picoxystrobin; a composition containing the pyridazine compound (3) and trifloxystrobin; a composition containing the pyridazine compound (3) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (4) and dimoxystrobin; a composition containing the pyridazine compound (4) and azoxystrobin; a composition containing the pyridazine compound (4) and fluoxastrobin; a composition containing the pyridazine compound (4) and pyraclostrobin; a composition containing the pyridazine compound (4) and cresoxime-methyl; a composition containing the pyridazine compound (4) and picoxystrobin; a composition containing the pyridazine compound (4) and trifloxystrobin; a composition containing the pyridazine compound (4) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (5) and dimoxystrobin;
a composition containing the pyridazine compound (5) and azoxystrobin;
a composition containing the pyridazine compound (5) and fluoxastrobin;
a composition containing the pyridazine compound (5) and pyraclostrobin;
a composition containing the pyridazine compound (5) and cresoxime-methyl; a composition containing the pyridazine compound (5) and picoxystrobin;
a composition containing the pyridazine compound (5) and trifloxystrobin;
a composition containing the pyridazine compound (5) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (6) and dimoxystrobin;
a composition containing the pyridazine compound (6) and azoxystrobin;
a composition containing the pyridazine compound (6) and fluoxastrobin;
a composition containing the pyridazine compound (6) and pyraclostrobin;
a composition containing the pyridazine compound (6) and cresoxime-methyl; a composition containing the pyridazine compound (6) and picoxystrobin;
a composition containing the pyridazine compound (6) and trifloxystrobin;
a composition containing the pyridazine compound (6) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
16/40 a composition containing the pyridazine compound (7) and dimoxystrobin; a composition containing the pyridazine compound (7) and azoxystrobin; a composition containing the pyridazine compound (7) and fluoxastrobin;
a composition containing the pyridazine compound (7) and pyraclostrobin;
a composition containing the pyridazine compound (7) and cresoxime-methyl; a composition containing the pyridazine compound (7) and picoxystrobin;
a composition containing the pyridazine compound (7), and trifloxystrobin;
a composition containing the pyridazine compound (7) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (8) and dimoxystrobin; a composition containing the pyridazine compound (8) and azoxystrobin; a composition containing the pyridazine compound (8) and fluoxastrobin;
a composition containing the pyridazine compound (8) and pyraclostrobin;
a composition containing the pyridazine compound (8) and cresoxime-methyl; a composition containing the pyridazine compound (8) and picoxystrobin;
a composition containing the pyridazine compound (8), and trifloxystrobin;
a composition containing the pyridazine compound (8) and N-methyl-a-methoxyminino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide;
a composition containing the pyridazine compound (1) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (1) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (1) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (1) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine (1) compound and pyraclostrobin in a weight ratio that satisfies the pyridazine (1) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (1) / creso17 / 40 xima-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (1) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (1) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (1) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine (1) / N-methyl compound -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (2) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (2) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (2) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine (2) compound and pyraclostrobin in a weight ratio that satisfies the pyridazine (2) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (2) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (2) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (2) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (2) / trifloxystrobin = 0.1 / 1 to 10/1;
18/40 a composition containing the pyridazine compound (2) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine compound (2) / N-methyl-a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (3) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (3) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (3) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine (3) compound and pyraclostrobin in a weight ratio that satisfies the pyridazine (3) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (3) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (3) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (3) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (3) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine (3) / N-methyl compound -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (4) / dimoxystrobin = 0.1 / 1 to 10/1;
19/40 a composition containing the pyridazine compound (4) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (4) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (4) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and pyraclostrobin in a weight ratio that satisfies the pyridazine (4) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (4) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (4) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (4) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (4) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine compound (4) / N-methyl -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (5) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (5) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (5) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and pyraclostrobin in
20/40 a weight ratio that satisfies the pyridazine compound (5) / pyraclostrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (5) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (5) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (5) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (5) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine compound (5) / N-methyl -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (6) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (6) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (6) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine (6) and pyraclostrobin compound in a weight ratio that satisfies the pyridazine (6) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (6) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (6) / picoxystrobi21 / 40 na = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (6) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (6) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine (6) / N-methyl compound -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and dimoxystrobin in a weight ratio that satisfies the pyridazine compound (7) / dimoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and azoxystrobin in a weight ratio that satisfies the pyridazine compound (7) / azoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (7) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and pyraclostrobin in a weight ratio that satisfies the pyridazine compound (7) / pyraclostrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (7) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (7) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (7) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (7) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine compound (7) / N-methyl -a-methoxyimino-2 - [(2,522 / 40 dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (8) and fluoxastrobin in a weight ratio that satisfies the pyridazine compound (8) / fluoxastrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine (8) and pyraclostrobin compound in a weight ratio that satisfies the pyridazine (8) / pyraclostrobin compound = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (8) and cresoxime-methyl in a weight ratio that satisfies the pyridazine compound (8) / cresoxime-methyl = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (8) and picoxystrobin in a weight ratio that satisfies the pyridazine compound (8) / picoxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (8) and trifloxystrobin in a weight ratio that satisfies the pyridazine compound (8) / trifloxystrobin = 0.1 / 1 to 10/1;
a composition containing the pyridazine compound (8) and N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide in a weight ratio that satisfies the pyridazine (8) / N-methyl compound -a-methoxyimino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide = 0.1 / 1 to 10/1;
The plant disease control method of the present invention (hereinafter referred to as the control method of the present invention) is accomplished by applying effective amounts of the pyridazine compound and the Qol compound to a plant or soil for the cultivation of a plant. Examples of such a plant include the stem and leaves of a plant, the seeds of a plant and the bulbs of a plant. Note that the bulb here means a bulb, grain, rhizome, stem tuber, root tuber and rhizophore.
In the control method of the invention, the pyridazine compound and the Qol compound can be applied simultaneously or separately to a plant or to the soil for the cultivation of a plant; however, they are generally applied in the form of the composition of the present invention, in
23/40 consideration of convenience.
In the control method of the invention, as a method for applying the pyridazine compound and the Qol compound, for example, application to the stem and leaves, application to the soil, application to the root and application to the seeds are mentioned.
As the application to the stem and leaves, for example, a method of applying the composition of the present invention to a surface of the plant that is cultivated, by spraying on the stem and leaves and spraying on the trunk, is mentioned.
Like application to the root, for example, a method of saturating an entire plant or the root in a drug solution containing the pyridazine compound and the Qol compound, and a method of binding a solid preparation containing the compound of pyridazine, the Qol compound and a solid vehicle, at the root of a plant, are mentioned.
As the application to the soil, for example, spraying, mixing and irrigating a drug solution to the soil, are mentioned.
As the application of seeds, for example, the application of the composition of the present invention to the seeds or bulbs of the plant to be protected from plant diseases, is mentioned. Specific examples of these include a mist spray application in which a suspension of the composition of the present invention is converted to mist and sprayed to a seed surface or bulb surface, a coating application in which a wetting powder, emulsion or spray agent. flow of the composition of the present invention is spread on the seeds or bulb by adding a small amount of water or directly, saturation application in which the seeds are soaked in a solution of the composition of the present invention for a predetermined time, a coating application film and granule coating application.
In the control method of the invention, the application amounts of the pyridazine compound and the Qol compound vary depending, for example, on the type of plant to be treated, type and frequency of occurrence
24/40 of the plant disease to be controlled, type of preparation, application time, application method, application site and weather conditions. For example, if the above compounds are applied to the stem and leaves of the plant or to the soil for growing a plant, the application amounts, that is, the total amount of the pyridazine compound and the Qol compound, are generally 1 at 500 g, preferably from 2 to 200 g and more preferably from 10 to 100 g per 1000 m2. Furthermore, if applied to the seeds, the application amounts of the pyridazine compound and the Qol compound, that is, the total amount of the pyridazine compound and the Qol compound, is generally 0.001 to 10 g and preferably 0, 01 to 1 g per kg of seeds.
The above emulsion, wetting powder, flowable agent and others are generally diluted with water and then sprayed for treatment. In this case, the concentrations of the pyridazine compound and the Qol compound, that is, the total concentration of the pyridazine compound and the Qol compound, is generally 0.0005 to 2% by weight and preferably 0.005 to 1% by weight. Weight. The above powder, granules, and more are generally applied directly without being diluted.
Examples
The present invention will be further specifically described by way of Preparation Examples and Experimental Examples below; however, the present invention is not limited to the following Examples. Note that, in the following Examples, the parts represent parts by weight unless otherwise specified.
First, the Reference Production Examples of the pyridazine compound to be used in the composition of the present invention will be further described more specifically; however, the present invention is not limited to these Examples.
Reference Production Example 1
25/40
-CH ₃
ΌΗ
CH ₃ (1)
To a mixture of 2-bromopropiophenone (2.13 g), 2.6difluorophenylacetic acid (1.81 g) and acetonitrile (25 ml), triethylamine (1.52 g) was added by dripping in a water bath, stirred in room temperature for 4 hours and then left to stand overnight. At the mixture, 4.57 g of 1,8-diazabicyclo [5.4.0] -7-undecene (hereinafter referred to as DBU) were added by dripping under ice-cooling. The mixture was stirred at room temperature for one hour. Thereafter, to the obtained mixture, air was blown while stirring at room temperature for 5 hours. To the reaction mixture, ice and 1 mol / L hydrochloric acid
10 were added. The mixture was extracted with ethyl acetate. The organic layer was sequentially washed with an aqueous saturated sodium bicarbonate solution and a saturated saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 3 (2,6-difluorophenyl) -5-hydroxy-5 -methyl-4-phenyl-2 (5H) -furanone (2.83 g).
15 1H-NMR (CDCI3, TMS) δ (ppm): 1.78 (3H, s), 4.07 (1H, br s), 6.77 - 6.85 (1H, br m), 6.96 - 7.08 (1H, m), 7.29 - 7.38 (4H, m), 7.53 - 7.55 (2H, m)
To a mixture of 3- (2,6-difluorophenyl) -5-hydroxy-5-methyl-4-phenyl2 (5H) -furanone (2.83 g) and 1-butanol (15 ml), hydrazine monohydrate (0.60 g) was added by dripping and then stirred in a heated bath
20 at 110 ° C for 2.5 hours. Subsequently, the reaction mixture was cooled to 0 ° C. The resulting solid substance was collected by filtration. The collected solid substance was washed with a solvent mixture of hexane and
26/40 t-butyl methyl ether (1: 1) and dried under reduced pressure to obtain 4- (2,6difluorophenyl) -6-methyl-5-phenyl-2H-pyridazin-3-one (1.70 g) .
1H-NMR (DMSO-d6, TMS) δ (ppm): 2.02 (3H, s), 6.92 - 6.98 (2H, m), 7.11 7.12 (2H, m), 7 , 27 - 7.36 (4H, m), 13.2 (1H, br s)
4- (2,6-Difluorophenyl) -6-methyl-5-phenyl-2H-pyridazin-3-one (1.54 g) and phosphorus oxychloride (10 ml) were mixed and stirred in a 110 ° heated bath C for 1.5 hours. The reaction mixture was allowed to cool to room temperature and then concentrated under reduced pressure. To the residue, ethyl acetate and ice water were added. Thereafter the mixture was separated and the organic layer was sequentially washed with a saturated aqueous sodium bicarbonate solution and a saturated saline solution and dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue (1.55 g) was washed with a mixture of hexane and ethyl acetate solution (10: 1), and subsequently with methyl butyl ether to obtain the pyridazine compound (1) (0.85 g) .
1H-NMR (CDCI3, TMS) δ (ppm): 2.55 (3H, s), 6.79 - 6.83 (2H, m), 7.07 - 7.09 (2H, m), 7, 23 - 7.30 (4H, m)
Reference Production Example 2 (2) (3)
4- (2,6-Difluorophenyl) -6-methyl-5-phenyl-2H-pyridazin-3-one (2.09 g) and phosphorus oxybromide (8.0 g) are mixed and stirred in a heated bath of 85 ° C for 1.5 hours and subsequently in a heated bath of 95 ° C for one hour. The reaction mixture is allowed to cool to room temperature, suspended in ethyl acetate (approximately 20 ml) and poured onto ice (approximately 100 g). After the solution obtained is neutralized with aqueous calcium bicarbonate solution, the residue is extracted with ethyl acetate and separated. The organic layer is washed with a saline solution, dried over anhydrous magnesium sulfate and
27/40 concentrated under reduced pressure. The residue obtained is subjected to column chromatography on silica gel to obtain the pyridazine compound (2).
The pyridazine compound (2) (0.72 g), copper cyanide (0.22 g) and Ν, Ν-dimethylacetamide (6 ml) are mixed and stirred under reflux
5 for 3 hours. The reaction mixture is allowed to cool to room temperature, added to ethyl acetate and water (about 50 ml each) and filtered with cerite. The filtrate is separated and the organic layer is washed with a saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained is subjected to column chromatography on silica gel to obtain the pyridazine compound (3). Reference Production Example 3
The pyridazine compound (1) (1.90 g), iron (III) acetylacetonate (0.42 g), tetrahydrofuran (60 ml) and N-methylpyrrolidone (6 ml) are mixed. To this, methylmagnesium bromide (3.0 mol / L of diethyl ether solution)
15 (6 ml) is added while stirring under ice cooling. To the reaction mixture, a 1 mol / L aqueous hydrochloric acid solution (30 ml) is added by dripping and water is added. After that, the reaction mixture is extracted with ethyl acetate. The organic layer is sequentially washed with an aqueous solution of calcium bicarbonate and a saline solution,
20 dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained is subjected to column chromatography on silica gel to obtain the pyridazine compound (4).
Reference Production Example 4 (6) (7)
28/40
6-Methyl-5-phenyl-4- (2,4,6-trifluorophenyl) -2H-pyridazin-3-one (2.21 g) and phosphorus oxybromide (8.0 g) are mixed and stirred in a bath heated at 85 ° C for 1.5 hours and subsequently in a heated bath of 95 ° C for one hour. The reaction mixture is allowed to cool to room temperature, suspended in ethyl acetate (around 20 ml) and poured into ice (around 100 g). After the obtained solution is neutralized with aqueous solution of calcium bicarbonate, the residue is extracted with ethyl acetate and separated. The organic layer is washed with a saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained is subjected to column chromatography on silica gel to obtain the pyridazine compound (6) ·
The pyridazine compound (6) (0.76 g), copper cyanide (0.22 g) and N, N-dimethylacetamide (6 ml) are mixed and stirred under reflux for 3 hours. The reaction mixture is allowed to cool to room temperature, added to ethyl acetate and water (around 50 ml each) and filtered with cerite. The filtrate is separated and the organic layer is washed with a saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained is subjected to column chromatography on silica gel to obtain the pyridazine compound (7). Reference Production Example 5
The pyridazine compound (5) (2.01 g), iron (III) acetylacetonate (0.42 g), tetrahydrofuran (60 ml) and N-methylpyrrolidone (6 ml) are mixed. To this, methylmagnesium bromide (3.0 mol / L diethyl ether solution) (6 ml) is added while stirring under cooling with ice. To the reaction mixture, an aqueous hydrochloric acid solution (30 ml) is added by dripping and water is added. The reaction mixture is then extracted
29/40 with ethyl acetate. The organic layer is sequentially washed with an aqueous solution of calcium bicarbonate and a saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained is subjected to column chromatography on silica gel to obtain the pyridazine compound (8).
Preparation Example 1
Each of the pyridazine compounds from (1) to (8) (2.5 parts), dimoxystrobin (1.25 part), polyoxyethylene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76, 25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 2
Each of the pyridazine compounds from (1) to (8) (2.5 parts), azoxystrobin (1.25 part), polyoxyethylene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76, 25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 3
Each of the pyridazine compounds from (1) to (8) (2.5 parts), fluoxastrobin (1.25 part), polyoxyethylene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76, 25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 4
Each of the pyridazine compounds of (1) to (8) (2.5 parts), pyraclostrobin (1.25 part), polyoxyethylene phenyl ether (14 parts), calcium dodecyl benzene sulfonate (6 parts) and xylene (76, 25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 5
Each of the pyridazine compounds from (1) to (8) (2.5 parts), cresoxime-methyl (1.25 part), polyoxyethylene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene ( 76.25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 6
Each of the pyridazine compounds from (1) to (8) (2.5 parts),
30/40 picoxystrobin (1.25 part), polyoxyethylene styrene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76.25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 7
Each of the pyridazine compounds from (1) to (8) (2.5 parts), trifloxystrobin (1.25 part), phenyl polyoxyethylene ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76, 25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 8
Each of the pyridazine compounds from (1) to (8) (2.5 parts), N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide (1.25 part) , polyoxyethylene styrene phenyl ether (14 parts), calcium dodecylbenzenesulfonate (6 parts) and xylene (76.25 parts) are well mixed. In this way, the preparations are obtained.
Preparation Example 9
Each of the pyridazine compounds from (1) to (8) (2 parts), dimoxystrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
Preparation Example 10
Each of the pyridazine compounds from (1) to (8) (2 parts), azoxystrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
Preparation Example 11
Each of the pyridazine compounds from (1) to (8) (2 parts), fluoxastrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
31/40
Preparation Example 12
Each of the pyridazine compounds from (1) to (8) (2 parts), pyraclostrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
Preparation Example 13
Each of the pyridazine compounds from (1) to (8) (2 parts), cresoxime-methyl (8 parts), a mixture of white carbon and ammonium sulfate salt of polyoxyethylene alkyl ether (in a weight ratio of 1 : 1) (35 parts) and water (55 parts) are mixed and finely ground by a wet grinding method. In this way, the preparations are obtained.
Preparation Example 14
Each of the pyridazine compounds from (1) to (8) (2 parts), picoxystrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
Preparation Example 15
Each of the pyridazine compounds from (1) to (8) (2 parts), trifloxystrobin (8 parts), a mixture of white carbon and polyoxyethylene alkyl ether ammonium sulfate salt (in a 1: 1 weight ratio ) (35 parts) and water (55 parts) are mixed and finely ground using a wet grinding method. In this way, the preparations are obtained.
Preparation Example 16
Each of the pyridazine compounds from (1) to (8) (2 parts), N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide (8 parts), a mixture of white carbon and ammonium sulfate salt of polyoxyethylene alkyl ether (in a 1: 1 weight ratio) (35 parts) and water (55 parts) are mixed and finely ground by a wet grinding method. In this way, the preparations are obtained.
Preparation Example 17
32/40
Each of the pyridazine compounds from (1) to (8) (5 parts), dimoxystrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 18
Each of the pyridazine compounds from (1) to (8) (5 parts), azoxystrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 19
Each of the pyridazine compounds from (1) to (8) (5 parts), fiuoxastrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 20
Each of the pyridazine compounds from (1) to (8) (5 parts), pyraclostrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts) ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and sili33 / 40 magnesium aluminum cate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred . In this way, the preparations are obtained.
Preparation Example 21
Each of the pyridazine compounds from (1) to (8) (5 parts), cresoxime-methyl (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol ( 2 parts) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 22
Each of the pyridazine compounds from (1) to (8) (5 parts), picoxystrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 23
Each of the pyridazine compounds from (1) to (8) (5 parts), trifloxystrobin (10 parts), sorbitan trioleate (1.5 part) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts ) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained. Preparation Example 24
Each of the pyridazine compounds from (1) to (8) (5 parts), N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide (10 parts),
34/40 sorbitan trioleate (1.5 parts) and an aqueous solution (28.5 parts) containing polyvinyl alcohol (2 parts) are mixed and finely ground by a wet grinding method. To the obtained ground product, an aqueous solution (45 parts) containing xanthan gum (0.05 part) and magnesium aluminum silicate (0.1 part) is added, and further propylene glycol (10 parts) is added and stirred. In this way, the preparations are obtained.
Preparation Example 25
Each of the pyridazine compounds from (1) to (8) (1 part), dimoxystrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 26
Each of the pyridazine compounds from (1) to (8) (1 part), azoxystrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 27
Each of the pyridazine compounds from (1) to (8) (1 part), fluoxastrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 28
Each of the pyridazine compounds from (1) to (8) (1 part), pyraclostrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. THE
35/40 mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 29
Each of the pyridazine compounds from (1) to (8) (1 part), cresoxymethyl (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts ) and kaolin clay (62 parts) are crushed and well mixed. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 30
Each of the pyridazine compounds from (1) to (8) (1 part), picoxystrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 31
Each of the pyridazine compounds from (1) to (8) (1 part), trifloxystrobin (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained.
Preparation Example 32
Each of the pyridazine compounds from (1) to (8) (1 part), Nmethyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide (4 parts), synthesized silicon oxide containing water (1 part), calcium ligninosulfonate (2 parts), bentonite (30 parts) and kaolin clay (62 parts) are crushed and mixed well. To this, water is added. The mixture is sufficiently kneaded, granulated and dried. In this way, the preparations are obtained. Preparation Example 33
Each of the pyridazine compounds from (1) to (8) (12.5 par36 / 40 tes), cresoxime-methyl (37.5 parts), calcium ligninosulfonate (3 parts), sodium lauryl sulfate (2 parts) and synthesized silicon oxide containing water (45 parts) are crushed and mixed well. In this way, the preparations are obtained.
Preparation Example 34
Each of the pyridazine compounds from (1) to (8) (3 parts), azoxystrobin (2 parts), kaolin clay (85 parts) and talc (10 parts) are crushed and mixed well. In this way, the preparations are obtained.
In the following, the experimental examples will be described.
Experimental Example 1
A plastic pot was loaded with soil. In the soil, wheat seeds (cultivar; Apogee) were sown and cultivated for 14 days in a greenhouse. A test compound was dissolved in a CEC cocktail (cidohexanone: Sorpol (trademark), 2680X (manufactured by TOHO Chemical Industry Co., Ltd.) = 5: 1 (volume ratio)) to make a preparation. After that, the preparation was diluted with water to a predetermined concentration. The diluted solution was sprayed onto the stem and leaves in such a way that the diluted solution was sufficiently bound to the surfaces of the wheat leaves. After spraying, the plant was dried with air. Two days later, an aqueous suspension (about 1,000,000 / ml) containing conidia spores from the wheat leaf spot (Mycosphaerella graminicola) was sprayed to inoculate the spores. After completion of inoculation, the plant was allowed to swell first in a high humidity location at 18 oC for 3 days and then the plant was removed from the site in high humidity and transferred to an 18 oC thermostatic chamber for 14 days. In this way, the wheat was grown (this is referred to as a treatment zone). After that, the damaged area of the wheat leaf spot was checked.
On the other hand, wheat was grown in the same way as in the treatment zone, except that a diluted solution of a test compound was not sprayed on the stem and leaves (this is referred to as a non-treatment zone). The damaged area of the wheat leaf spot was evaluated in the same way as in the treatment zone.
37/40
From the injured areas of the treatment zone and the non-treatment zone, the effectiveness of the treatment zone was obtained according to the following expression (1). The results are shown in [Table 1] through [Table 8].
5 Effectiveness (%) = (1 - Injured area of the treatment zone) x 100
Injured area of the non-treatment zone
Expression (1) [Table 1]
The pyridazine compound (1) [ppm] Azoxystrobin[PPm] Efficiency (%) 3.1 3.1 100
[Table 2]
The pyridazine compound (5) [PPm] Azoxystrobin[Ppm] Efficiency (%) 3.1 3.1 100
10 [Table 3]
The pyridazine compound (1) [PPm] N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide[PPm] Efficiency(%) 3.1 13 100
[Table 4]
The pyridazine compound (5) [PPm] N-methyl-a-methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide[ppm] Efficiency(%) 3.1 13 100
[Table 5]
The pyridazine compound (1) [PPm] Pyraclostrobin[ppm] Efficiency (%) 3.1 3.1 100
[Table 6]
The pyridazine compound (5) [ppm] Pyraclostrobin[PPm] Efficiency (%) 3.1 3.1 100
38/40 [Table 7]
The pyridazine compound (1) [PPm] Picoxystrobin[PPm] Efficiency (%) 3.1 3.1 100
[Table 8]
The pyridazine compound (5) [PPm] Picoxystrobin[ppm] Efficiency (%) 3.1 3.1 100
Experimental Example 2
Through the use of a rotary seed processor (sowing, manufactured by Hans-UIrich Hege GmbH), a solution of cyclohexanone (100 pl) containing a predetermined weight of a test compound was greased on the wheat seeds (cultivar; Shirogane) ( 10 g) naturally infected with pink snow mold spores (Microdochium nivale).
One day after treatment, a plastic pot was loaded with soil and the seeds treated with the test compound were sown in the soil and grown in a glass greenhouse for 20 days (this is referred to as a treatment zone). After that, the seedlings obtained from individual seeds by germination were observed in relation to the onset of pink snow mold and a disease incidence rate was obtained according to the following expression (2).
On the other hand, wheat seeds not treated with the aforementioned cover treatment were grown in the same way as in the treatment zone (this is referred to as a non-treatment zone). A disease incidence rate was obtained in the same way as in the treatment zone.
As a result, the incidence rate of seedlings obtained from germinated wheat seeds and treated with the composition of the present invention was lower than that of seedlings in the non-treatment zone.
From the incidence rates of the treatment zone and the non-treatment zone, the effectiveness in the treatment zone was obtained according to the following expression (1). The results are shown in [Table 9] through [Table 12].
Incidence rate (%) = (1 - Number of initial seedlings) x 100
Total number of seedlings
5 Expression (2)
Effectiveness (%) = (1 - Treatment zone incidence rate) x 100
Incidence rate of the non-treatment zone Expression (3) [Table 9]
The pyridazine compound (1)[g / 100 kg of seeds] N-methyl-a-methoxy-imino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide [g / 100 kg of seeds] Efficiency(%) 5 5 100
10 [Table 10]
The pyridazine compound (5)[g / 100 kg of seeds] N-methyl-a-methoxy-imino-2 - [(2,5dimethylphenoxy) methyl] phenylacetamide [g / 100 kg of seeds] Efficiency(%) 5 5 100
[Table 11]
The pyridazine compound (1)[g / 100 kg of seeds] Azoxystrobin [g / 100 kg of seeds] Efficiency (%) 5 1 100
[Table 12]
The pyridazine compound (5)[g / 100 kg of seeds] Azoxystrobin [g / 100 kg of seeds] Efficiency (%) 5 1 100
Experimental Example 3
Through the use of a rotary seed processor (seed15, manufactured by Hans-UIrich Hege GmbH), a solution of cyclohexanone (100 pl) containing a predetermined weight of a test compound was greased on the wheat seeds (cultivar; Shirogane) (10 g) Naturally 40/40 infected with pink snow mold spores (Microdochium nivale).
One day after treatment, a plastic pot was loaded with soil and the seeds treated with the test compound were sown in the soil and grown in a glass greenhouse for 20 days (this is referred to as a treatment zone). After that, the seedlings obtained from individual seeds by germination were observed in relation to the onset of pink snow mold and a disease incidence rate was obtained according to the following expression (2).
On the other hand, wheat seeds not treated with the aforementioned cover treatment were grown in the same way as in the treatment zone (this is referred to as a non-treatment zone). A disease incidence rate was obtained in the same way as in the treatment zone.
As a result, the incidence rate of seedlings obtained from
15 from germinating wheat seeds and treated with the composition of the present invention was less than that of the seedlings in the non-treatment zone.
Incidence rate (%) = (1 - Number of initial seedlings) x 100
Total number of seedlings
Expression (2)
1/2
1. Plant disease control composition, characterized by the fact that it comprises a pyridazine compound represented by formula (I):
5 where
R ¹ represents a chlorine atom, and R ² represents a hydrogen atom, and a Qol compound selected from Group (A).
A group):
10 a group consisting of dimoxystrobin, azoxystrobin, fiuoxastrobin, pyraclostrobin, famoxadone, cresoxime-methyl, picoxystrobin, trifloxystrobin, N-methyl-a-methoxy-imino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide and phenylacetamide and phenylacetamide.
2. Plant disease control composition according to
15 with claim 1, characterized in that a weight ratio of the pyridazine compound and the Qol compound satisfies the pyridazine compound / Qol compound = 0.1 / 1 to 10/1.
3. Method for the control of plant diseases, characterized by the fact that it comprises a step of applying effective amounts of a pyridazine compound represented by formula (I):
on what
R ¹ represents a chlorine atom, and R ² represents a hydrogen atom, and a Qol compound selected from Group (A) in a plant or soil for the growth of a plant,
Petition 870180052670, dc 19/06/2018, p. 4/9
2/2
A group):
a group consisting of dimoxystrobin, azoxystrobin, fiuoxastrobin, pyraclostrobin, famoxadone, crespoxyl, picoxystrobin, trifloxystrobin, N-methyl-a-methoxy-imino-2 - [(2,55 dimethylphenoxy) methyl] phenylacetamide and phenamidone.
4. Plant disease control method according to claim 3, characterized in that a weight ratio of the pyridazine compound and the Qol compound satisfies the pyridazine compound / the Qol compound = 0.1 / 1 to 10/1.
10 5. Method for controlling plant diseases according to claim 3 or 4, characterized by the fact that the plant or soil for growing a plant is wheat or soil for growing wheat.
Petition 870180052670, of 19/06/2018, p. 5/9

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CN103068238A|2013-04-24|

---

JP2012056941A|2012-03-22|

---

US20130137683A1|2013-05-30|

---

CA2807627A1|2012-02-16|

---

JP5857512B2|2016-02-10|

---

EP2604116A1|2013-06-19|

---

EP2604116A4|2014-07-02|

引用文献:

---

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

---

DK0754672T3|1994-04-06|2000-11-13|Shionogi & Co|Gamma-Substituted Phenylacetic Acid Derivative, Method of Preparation thereof and Agricultural Fungicide Containing Same|

---

ES2324883T3|2004-06-09|2009-08-18|Sumitomo Chemical Company, Limited|PIRIDAZINE COMPOSITE AND ITS USE.|

---

WO2006001175A1|2004-06-28|2006-01-05|Sumitomo Chemical Company, Limited|Pyridazine compound and use thereof|

---

CN101262764A|2005-07-14|2008-09-10|巴斯夫欧洲公司|Fungicide mixtures based on 1-methyl-pyrazol-4-yl carboxylic acid anilides|

---

MX2009004282A|2006-10-25|2009-05-05|Syngenta Participations Ag|Novel pyridazine derivatives.|

---

EP1916240A1|2006-10-25|2008-04-30|Syngeta Participations AG|Pyridazine derivatives|

---

EP2011396A1|2007-07-03|2009-01-07|Bayer CropScience AG|Active compound combinations|JP2013142065A|2012-01-10|2013-07-22|Sumitomo Chemical Co Ltd|Plant disease control composition and application of the same|

---

JP2013142063A|2012-01-10|2013-07-22|Sumitomo Chemical Co Ltd|Plant disease control composition and application of the same|

---

JP2013142064A|2012-01-10|2013-07-22|Sumitomo Chemical Co Ltd|Plant disease control composition and application of the same|

---

JP2013142066A|2012-01-10|2013-07-22|Sumitomo Chemical Co Ltd|Plant disease control composition and application of the same|

---

JP2013142067A|2012-01-10|2013-07-22|Sumitomo Chemical Co Ltd|Plant disease control composition and application of the same|

---

JP2013142062A|2012-01-10|2013-07-22|Sumitomo Chemical Co Ltd|Plant disease control composition and application of the same|

---

JP2014019680A|2012-07-20|2014-02-03|Sumitomo Chemical Co Ltd|Composition for controlling plant disease and application therefor|

---

EP2980079B1|2013-03-26|2017-10-25|Sumitomo Chemical Company, Limited|Method of manufacturing pyridazinone compound|

---

EP3004065B1|2013-05-24|2017-10-18|Sumitomo Chemical Company, Limited|Method for producing pyridazine compound|

---

BR112016001354B1|2013-07-22|2021-03-09|Sumitomo Chemical Company, Limited|composition and method for the control of plant disease|

---

BR112018001745A2|2015-08-11|2018-09-11|Sumitomo Chemical Co|plant disease control composition and plant disease control method|

---

BR112018007572A2|2015-10-14|2018-10-23|Syngenta Participations Ag|fungicidal compositions|

---

FR3048331B1|2016-03-04|2018-05-04|Sumitomo Chemical Company, Limited|LIQUID PESTICIDE CONTAINING PYRIDAZINE COMPOUND AND METHOD OF CONTROLLING PLANT DISEASE USING THE SAME|

---

BR112018070785A2|2016-04-12|2019-02-05|Syngenta Participations Ag|microbiocidal oxadiazole derivatives|

---

GB201609574D0|2016-06-01|2016-07-13|Syngenta Participations Ag|Fungicidal compositions|

---

EP3464251B1|2016-06-03|2021-03-03|Syngenta Participations AG|Microbiocidal oxadiazole derivatives|

---

AR108745A1|2016-06-21|2018-09-19|Syngenta Participations Ag|MICROBIOCIDES OXADIAZOL DERIVATIVES|

---

EP3487843A1|2016-07-22|2019-05-29|Syngenta Participations AG|Microbiocidal oxadiazole derivatives|

---

EP3487855A1|2016-07-22|2019-05-29|Syngenta Participations AG|Microbiocidal oxadiazole derivatives|

---

BR112019000942A2|2016-07-22|2019-04-30|Syngenta Participations Ag|microbiocidal oxadiazole derivatives|

---

WO2018029242A1|2016-08-11|2018-02-15|Syngenta Participations Ag|Microbiocidal oxadiazole derivatives|

---

BR112019005656A2|2016-09-23|2019-06-04|Syngenta Participations Ag|oxadiazole microbiocidal derivatives|

---

WO2018055133A1|2016-09-23|2018-03-29|Syngenta Participations Ag|Microbiocidal tetrazolone derivatives|

---

WO2018065414A1|2016-10-06|2018-04-12|Syngenta Participations Ag|Microbiocidal oxadiazole derivatives|

---

UY37623A|2017-03-03|2018-09-28|Syngenta Participations Ag|DERIVATIVES OF OXADIAZOL THIOPHEN FUNGICIDES|

---

EP3592738A1|2017-03-10|2020-01-15|Syngenta Participations AG|Microbiocidal oxadiazole derivatives|

---

WO2018177880A1|2017-03-31|2018-10-04|Syngenta Participations Ag|Fungicidal compositions|

---

KR20190134674A|2017-03-31|2019-12-04|신젠타 파티서페이션즈 아게|Fungicidal composition|

---

CN110506040A|2017-04-03|2019-11-26|先正达参股股份有限公司|Kill the oxadiazole derivatives of microorganism|

---

BR112019020756A2|2017-04-05|2020-04-28|Syngenta Participations Ag|OXADIAZOL DERIVATIVES MICROBICIDES|

---

BR112019021019A2|2017-04-05|2020-05-05|Syngenta Participations Ag|microbiocidal oxadiazole derivatives|

---

WO2018184986A1|2017-04-05|2018-10-11|Syngenta Participations Ag|Microbiocidal oxadiazole derivatives|

---

WO2018184985A1|2017-04-05|2018-10-11|Syngenta Participations Ag|Microbiocidal oxadiazole derivatives|

---

BR112019020819A2|2017-04-05|2020-04-28|Syngenta Participations Ag|microbicidal oxadiazole derivatives|

---

BR112019020735A2|2017-04-05|2020-05-12|Syngenta Participations Ag|OXADIAZOL DERIVATIVES MICROBICIDES|

---

WO2018185211A1|2017-04-06|2018-10-11|Syngenta Participations Ag|Microbiocidal oxadiazole derivatives|

---

CN110709395A|2017-06-02|2020-01-17|先正达参股股份有限公司|Microbicidal oxadiazole derivatives|

---

BR112019024993A2|2017-06-02|2020-06-16|Syngenta Participations Ag|FUNGICIDED COMPOSITIONS|

---

EP3638032A1|2017-06-14|2020-04-22|Syngenta Participations AG|Fungicidal compositions|

---

BR112019027900A2|2017-06-28|2020-07-21|Syngenta Participations Ag|fungicidal compositions|

---

WO2019011929A1|2017-07-11|2019-01-17|Syngenta Participations Ag|Microbiocidal oxadiazole derivatives|

---

WO2019011923A1|2017-07-11|2019-01-17|Syngenta Participations Ag|Microbiocidal oxadiazole derivatives|

---

BR112020000457A2|2017-07-11|2020-07-21|Syngenta Participations Ag|microbiocidal oxadiazole derivatives|

---

WO2019011928A1|2017-07-11|2019-01-17|Syngenta Participations Ag|Microbiocidal oxadiazole derivatives|

---

WO2019012001A1|2017-07-12|2019-01-17|Syngenta Participations Ag|Microbiocidal oxadiazole derivatives|

---

WO2019012011A1|2017-07-12|2019-01-17|Syngenta Participations Ag|Microbiocidal oxadiazole derivatives|

---

BR112020000463A2|2017-07-13|2020-07-21|Syngenta Participations Ag|microbiocidal oxadiazole derivatives|

---

WO2019053010A1|2017-09-13|2019-03-21|Syngenta Participations Ag|Microbiocidal quinoline carboxamide derivatives|

---

BR112020004933A2|2017-09-13|2020-09-15|Syngenta Participations Ag|microbiocidal derivatives of quinolinecarboxamide|

---

CN111094247A|2017-09-13|2020-05-01|先正达参股股份有限公司|Microbicidal quinolinecarboxamide derivatives|

---

CN111050558A|2017-09-13|2020-04-21|先正达参股股份有限公司|Microbicidal quinolinecarboxamide derivatives|

---

BR112020004692A2|2017-09-13|2020-09-15|Syngenta Participations Ag|microbiocidal derivatives of quinolinecarboxamide|

---

US11129386B2|2017-09-13|2021-09-28|Syngenta Participations Ag|Microbiocidal quinoline carboxamide derivatives|

---

JP2020533389A|2017-09-13|2020-11-19|シンジェンタ パーティシペーションズ アーゲー|Microbial quinolinecarboxamide derivative|

---

UY37912A|2017-10-05|2019-05-31|Syngenta Participations Ag|PICOLINAMIDE DERIVATIVES FUNGICIDES THAT CONTAIN HETEROARILO OR HETEROARILOXI TERMINAL GROUPS|

---

UY37913A|2017-10-05|2019-05-31|Syngenta Participations Ag|PICOLINAMIDE DERIVATIVES FUNGICIDES THAT CARRY A QUATERNARY TERMINAL GROUP|

---

EP3710429A1|2017-11-15|2020-09-23|Syngenta Participations AG|Microbiocidal picolinamide derivatives|

---

BR112020009984A2|2017-11-20|2020-11-03|Syngenta Participations Ag|microbicidal oxadiazole derivatives|

---

EA202091322A1|2017-11-29|2020-10-09|Зингента Партисипейшнс Аг|MICROBIOCIDE THIAZOLIC DERIVATIVES|

---

BR112020011990A2|2017-12-19|2020-11-17|Syngenta Participations Ag|microbiocidal picolinamide derivatives|

---

BR112020021645A2|2018-04-26|2021-01-26|Syngenta Participations Ag|microbicidal oxadiazole derivatives|

---

WO2020002331A1|2018-06-29|2020-01-02|Syngenta Crop Protection Ag|Microbiocidal oxadiazole derivatives|

---

EP3818058A1|2018-07-02|2021-05-12|Syngenta Crop Protection AG|3--5--1,2,4-oxadiazole derivatives as agrochemical fungicides|

---

WO2020016180A1|2018-07-16|2020-01-23|Syngenta Crop Protection Ag|Microbiocidal oxadiazole derivatives|

---

WO2020058207A1|2018-09-19|2020-03-26|Syngenta Crop Protection Ag|Microbiocidal quinoline carboxamide derivatives|

---

JP2022502390A|2018-09-26|2022-01-11|シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト|Sterilizing and mold-killing composition|

---

WO2020070132A1|2018-10-06|2020-04-09|Syngenta Participations Ag|Microbiocidal quinoline dihydro-oxazine derivatives|

---

CN112789278A|2018-10-06|2021-05-11|先正达参股股份有限公司|Microbicidal quinoline dihydro-oxazine derivatives|

---

TW202035404A|2018-10-24|2020-10-01|瑞士商先正達農作物保護公司|Pesticidally active heterocyclic derivatives with sulfoximine containing substituents|

---

WO2020141135A1|2018-12-31|2020-07-09|Syngenta Crop Protection Ag|Pesticidally active heterocyclic derivatives with sulfur containing substituents|

---

US20220061324A1|2018-12-31|2022-03-03|Syngenta Crop Protection Ag|Pesticidally active heterocyclic derivatives with sulfur containing substituents|

---

CN110024793A|2019-05-14|2019-07-19|东莞东阳光科研发有限公司|A kind of composition containing Pyridachlometyl and thicyofen|

法律状态:
2017-12-26| B15K| Others concerning applications: alteration of classification|Free format text: AS CLASSIFICACOES ANTERIORES ERAM: A01N 43/58 , A01C 1/06 , A01G 7/06 , A01N 39/02 , A01N 43/54 , A01P 3/00 Ipc: A01N 43/58 (1980.01), A01N 39/02 (1980.01), A01N 4 Ipc: A01N 43/58 (1980.01), A01N 39/02 (1980.01), A01N 4 |

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2017-12-26| B07A| Application suspended after technical examination (opinion) [chapter 7.1 patent gazette]|

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2018-04-03| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

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2018-08-28| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2018-10-16| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 09/08/2011, OBSERVADAS AS CONDICOES LEGAIS. |

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2021-06-15| B21F| Lapse acc. art. 78, item iv - on non-payment of the annual fees in time|Free format text: REFERENTE A 10A ANUIDADE. |

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2021-10-05| B24J| Lapse because of non-payment of annual fees (definitively: art 78 iv lpi, resolution 113/2013 art. 12)|Free format text: EM VIRTUDE DA EXTINCAO PUBLICADA NA RPI 2632 DE 15-06-2021 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDA A EXTINCAO DA PATENTE E SEUS CERTIFICADOS, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013. |

优先权:

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申请号 | 申请日 | 专利标题

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JP2010179299|2010-08-10|

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PCT/JP2011/068196|WO2012020774A1|2010-08-10|2011-08-09|Plant disease control composition and application for same|

---