WO2020040077A1 - Composé de benzoxazole et son utilisation - Google Patents
Composé de benzoxazole et son utilisation Download PDFInfo
- Publication number
- WO2020040077A1 WO2020040077A1 PCT/JP2019/032239 JP2019032239W WO2020040077A1 WO 2020040077 A1 WO2020040077 A1 WO 2020040077A1 JP 2019032239 W JP2019032239 W JP 2019032239W WO 2020040077 A1 WO2020040077 A1 WO 2020040077A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- spot
- compound
- rust
- disease
- rot
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G13/00—Protecting plants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Definitions
- Patent Literature 1 discloses that a compound represented by the formula (B) (Hereinafter, referred to as compound B).
- An object of the present invention is to provide a compound having an excellent controlling effect on plant diseases.
- the present invention is as follows. [1] Formula (A) (Hereinafter, referred to as compound A). [2] A composition comprising the compound according to [1] and an inert carrier. [3] A method for controlling plant diseases by treating a plant or soil with an effective amount of the compound according to [1].
- plant diseases can be controlled.
- the composition of the present invention contains Compound A and an inert carrier.
- the composition of the present invention is generally a mixture of compound A and a solid carrier, an inert carrier such as a liquid carrier, and, if necessary, a surfactant and other formulation auxiliaries. It is formulated into powders, granules, wettable powders, wettable granules, flowables, dry flowables, microcapsules and the like.
- the composition of the present invention generally contains 0.0001 to 95% by weight of Compound A.
- solid carriers used in the formulation include clays (kaolin clay, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur, Activated carbon, calcium carbonate, etc., fine powders and granular materials such as fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, salt ammonium, etc.) and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, etc.) Polyester resins, nylon resins such as nylon-6, nylon-11 and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).
- clays kaolin clay, diatomaceous earth, bentonite, acid clay, etc.
- dry silica wet silica, talc
- liquid carrier examples include water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (toluene, xylene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), Esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, etc.), ethers (diisopropyl ether, diethylene glycol dimethyl ether, etc.), amides (N, N-dimethylformamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), and Vegetable oils (soy oil, cottonseed oil, and the like).
- alcohols methanol, ethanol, etc.
- ketones acetone, methyl ethyl ketone, etc.
- aromatic hydrocarbons toluene, xylene, etc.
- surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate and alkyl sulfate. Surfactants.
- adjuvants for preparations include fixing agents, dispersants, coloring agents and stabilizers, specifically, casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymer (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid, etc.), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4-methoxyphenol) And 3-tert-butyl-4-methoxyphenol).
- fixing agents include fixing agents, dispersants, coloring agents and stabilizers, specifically, casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymer (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid, etc
- Compound A is effective against plant pathogenic bacteria.
- plant diseases derived from plant pathogens include the following.
- the name in parentheses indicates the scientific name of the pathogen causing the disease.
- Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), harmless seedling (Gibberella fujikuroi), yellow dwarf (Sclerophthora macrospora); wheat powdery mildew (Blumeria) graminis), Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), Yellow rust (Puccinia striiformis), Black rust (Puccinia graminis), Red rust (Puccinia recondita), Red snow rot (Microdochium) , Microdochium majus), snow rot sclerotium scab (Typhula incarnata, Typhula ishikariensis), naked smut (Ustilago tritici), scab (Tilletia caries,
- Powdery mildew of strawberry (Sphaerotheca humuli); Net rot of tea (Exobasidium reticulatum), white scab (Elsinoe leucospila), ring spot (Pestalotiopsis sp.), Anthracnose (Colletotrichum theae-sinensis); Scab (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophthora nicotianae); sugar beet brown spot (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black rot (Aphanomyces cochlioides), rust (Uromyces betae); rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); chrysanthem
- Rhizoctonia solani and sigatoka disease of bananas (Mycosphaerella fijiensis, Mycosphaerella musicola). Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, and Diplodia spp. Disease. Viral diseases of various crops mediated by the genus Polymixa or the genus Olpidium. Seedling blight disease of rice (Burkholderia plantarii); spot bacterial disease of cucumber (Pseudomonas syringae pv. Lachrymans); bacterial wilt of eggplant (Ralstonia solanacearum); carotovora) etc.
- the method for controlling plant diseases of the present invention includes, for example, treatment of plants such as foliage application and seed disinfection; and treatment of plant cultivation areas such as soil treatment.
- the treatment amount of Compound A is usually 1 to 10000 g per 1000 m 2 .
- Compound A When Compound A is formulated into an emulsion, wettable powder, flowable or the like, it is usually diluted with water so that the active ingredient concentration becomes 0.01 to 10000 ppm, and granules, powders and the like are used. Usually, it is applied as it is.
- composition of the present invention can be used as an agent for controlling plant diseases in agricultural lands such as fields, paddy fields, lawns, and orchards.
- Step 1 A mixture of 69.7 g of 2-amino-4- (trifluoromethanesulfonyl) phenol, 37.3 g of N, N-diisopropylethylamine and 191 g of tetrahydrofuran prepared by the method described in US Pat. No. 8,426,443 was added with nitrogen. Under an atmosphere, a mixture of 42.2 g of pyridine-2-carbonyl chloride and 206 g of toluene was added dropwise at 40 ° C., and the mixture was stirred at 40 ° C. for 3 hours. 88.8 g of an 8% aqueous sodium hydroxide solution was added to the obtained mixture, and the mixture was cooled to 5 ° C.
- Test example 1 After dispensing 1 ⁇ L of a dimethyl sulfoxide solution containing a predetermined concentration of compound A into wells of a titer plate (96 wells), 150 ⁇ L of a complete medium containing a spore suspension of Botrytis cinerea was dispensed. Was adjusted to have a final concentration of 100 ppm, which was treated. A non-treated section was prepared in another well. After the plate was cultured at 18 ° C. for 3 days to grow the fungus, the absorbance at 600 nm of each well of the titer plate was measured to determine the growth of the fungus. Based on the degree of growth, the efficacy was calculated using "Equation 1".
- Comparative test example 1 The test was performed according to Test Example 1 using Compound B instead of Compound A. As a result, the efficacy was 0%.
- Compound A exhibits an excellent control effect on plant diseases.
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2020538371A JP7250023B2 (ja) | 2018-08-20 | 2019-08-19 | ベンゾオキサゾール化合物及びその用途 |
CN201980042115.8A CN112313227B (zh) | 2018-08-20 | 2019-08-19 | 苯并噁唑化合物及其用途 |
KR1020217001147A KR102684363B1 (ko) | 2018-08-20 | 2019-08-19 | 벤조옥사졸 화합물 및 그 용도 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018-153853 | 2018-08-20 | ||
JP2018153853 | 2018-08-20 |
Publications (1)
Publication Number | Publication Date |
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WO2020040077A1 true WO2020040077A1 (fr) | 2020-02-27 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2019/032239 WO2020040077A1 (fr) | 2018-08-20 | 2019-08-19 | Composé de benzoxazole et son utilisation |
Country Status (4)
Country | Link |
---|---|
JP (1) | JP7250023B2 (fr) |
KR (1) | KR102684363B1 (fr) |
CN (1) | CN112313227B (fr) |
WO (1) | WO2020040077A1 (fr) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010032874A1 (fr) * | 2008-09-19 | 2010-03-25 | 住友化学株式会社 | Composition utilisée en milieu agricole |
JP2016506360A (ja) * | 2012-12-27 | 2016-03-03 | 住友化学株式会社 | 縮合オキサゾール化合物及びその有害生物防除用途 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
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BR112012007237A2 (pt) * | 2009-09-30 | 2019-09-24 | Sumitomo Chemical Co | composição e método para controlar pragas artrópodes |
WO2014065411A1 (fr) * | 2012-10-26 | 2014-05-01 | 株式会社エス・ディー・エス バイオテック | Dérivé de sulfonamide utilisé comme agent de lutte contre les organismes nuisibles dans le domaine agricole/horticole |
CN104206385B (zh) * | 2013-06-04 | 2017-02-08 | 沈阳中化农药化工研发有限公司 | 胺类化合物作为杀菌剂的应用 |
CN106536516B (zh) * | 2014-06-09 | 2019-09-03 | 住友化学株式会社 | 用于制备吡啶化合物的方法 |
CN105348298B (zh) * | 2014-07-04 | 2019-03-19 | 沈阳中化农药化工研发有限公司 | 取代芳基吡啶类化合物及其用途 |
-
2019
- 2019-08-19 WO PCT/JP2019/032239 patent/WO2020040077A1/fr active Application Filing
- 2019-08-19 JP JP2020538371A patent/JP7250023B2/ja active Active
- 2019-08-19 CN CN201980042115.8A patent/CN112313227B/zh active Active
- 2019-08-19 KR KR1020217001147A patent/KR102684363B1/ko active IP Right Grant
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010032874A1 (fr) * | 2008-09-19 | 2010-03-25 | 住友化学株式会社 | Composition utilisée en milieu agricole |
JP2016506360A (ja) * | 2012-12-27 | 2016-03-03 | 住友化学株式会社 | 縮合オキサゾール化合物及びその有害生物防除用途 |
Non-Patent Citations (2)
Title |
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PARVEEN S, S. ET AL.: "Synthesis, vibrational spectroscopic investigations, molecular docking, antibacterial and antimicrobial studies of 5-ethylsulphonyl-2-(p-aminophenyl)benzoxazole", JOURNAL OF MOLECULAR STRUCTURE, vol. 1115, 2016, pages 94 - 104, XP029491280, ISSN: 0022-2860, DOI: 10.1016/j.molstruc.2016.02.057 * |
TEMIZ-ARPACI, 0. ET AL.: "Synthesis and biological activity of some new benzoxazoles", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 43, no. 7, 2008, pages 1423 - 1431, XP022795986, ISSN: 0223-5234, DOI: 10.1016/j.ejmech.2007.09.023 * |
Also Published As
Publication number | Publication date |
---|---|
JPWO2020040077A1 (ja) | 2021-09-24 |
KR102684363B1 (ko) | 2024-07-11 |
KR20210046651A (ko) | 2021-04-28 |
CN112313227B (zh) | 2023-09-08 |
JP7250023B2 (ja) | 2023-03-31 |
CN112313227A (zh) | 2021-02-02 |
TW202017921A (zh) | 2020-05-16 |
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