CN112236427A - Benzoxazole compounds and uses thereof - Google Patents
Benzoxazole compounds and uses thereof Download PDFInfo
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- CN112236427A CN112236427A CN201980038344.2A CN201980038344A CN112236427A CN 112236427 A CN112236427 A CN 112236427A CN 201980038344 A CN201980038344 A CN 201980038344A CN 112236427 A CN112236427 A CN 112236427A
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- Prior art keywords
- compound
- alternaria
- blight
- rust
- spot
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- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
Abstract
Disclosed is a compound having excellent control efficacy against plant diseases. The compound represented by the formula (A) has excellent controlling efficacy against plant diseases.
Description
Technical Field
The present application claims priority and its benefits to japanese patent application No. 2018-153852, filed on 8/20/2018, and is incorporated by reference in its entirety.
The present invention relates to benzoxazole compounds and uses thereof.
Background
Conventionally, various compounds have been developed and put into practical use for controlling plant diseases (see non-patent document 1).
Patent document 1 describes a compound represented by formula (B) (hereinafter referred to as compound B) as an insecticide. Patent document 2 describes a compound represented by formula (C) (hereinafter referred to as compound C) as an insecticide.
[ solution 1]
[ solution 2]
Documents of the prior art
Patent document
Patent document 1: U.S. patent application publication No. 2016/0368915 specification
Patent document 2: U.S. patent application publication No. 2015/0313234 specification
Non-patent document
Non-patent document 1: the Pesticide Manual-17th edition (BCPC journal) ISBN 978-1-901396-88-1
Disclosure of Invention
Problems to be solved by the invention
The present invention addresses the problem of providing a compound having excellent control efficacy against plant diseases.
Means for solving the problems
The present invention is as follows.
[ 1] A compound (hereinafter referred to as Compound A) represented by the formula (A):
[ solution 3]
A composition comprising the compound described in [ 1] and an inactive carrier.
A method for controlling a plant disease, which comprises treating a plant or soil with an effective amount of the compound according to [ 1 ].
Effects of the invention
According to the present invention, plant diseases can be controlled.
Detailed Description
The compositions of the present invention contain compound a and an inactive carrier. The composition of the present invention is usually prepared by mixing the compound a with a non-active carrier such as a solid carrier or a liquid carrier, and adding a surfactant and other formulation auxiliaries as needed to prepare a formulation such as an emulsion, an oil, a powder, a granule, a wettable powder (japanese: water and a tablet), a granule-type wettable powder (japanese: powdery chalk, a tablet flux), a flowable agent (japanese: フロアブル agent), a dry flowable agent (japanese: ド ラ イ フロアブル agent), or a microcapsule.
The composition of the present invention usually contains 0.0001 to 95% by weight of compound A.
Examples of the solid carrier used in the preparation of the preparation include fine powders and granules of clay (kaolin, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, etc., nylon resins such as nylon-6, nylon-11, nylon-66, etc., polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, etc.).
Examples of the liquid carrier 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 (soybean oil, cottonseed oil, etc.).
Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, and polyethylene glycol fatty acid esters, and anionic surfactants such as alkylsulfonates, alkylbenzenesulfonates, and alkylsulfates.
Examples of other pharmaceutical adjuvants include a sticking agent, a dispersing agent, a coloring agent, and a stabilizer, and specific examples thereof include casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, and the like), lignin derivatives, bentonite (japanese text: ベントナイト), synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, and the like), isopropyl acid phosphate, 2, 6-di-t-butyl-4-methylphenol, and BHA (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol).
Compound a has efficacy against phytopathogens. Examples of the plant diseases derived from plant pathogenic bacteria include the following. The brackets indicate the scientific name of the pathogenic bacteria causing the disease.
Rice blast (Magnaporthe grisea), flax leaf spot (Cochliobolus miyabenus), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), and yellowing atrophy (Phytophthora grandis (Sclerophora)); powdery mildew of wheat (Blumeria graminis (Blumeria graminis) gibberellic disease (Fusarium graminearum), Fusarium avenaceum (Fusarium avenaceum), Fusarium culmorum (Fusarium culmorum), Microdochium nivale (Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red snow rot (Microdochium nivale), Microdochium macrosporum (Microdochium majus)), snow rot (Tilletia nivea), snow smus (Tilleta), black rot (Tylophora nivea), wheat head smut (Tilletia smus), wheat head smut (Ubberella tritici), wheat head smut (Tilletia nivea), wheat head smut (Ubberella reticulata), wheat head smut (Ubberella triticale), wheat head smut (Ubberella) of wheat head smut (Ubberella) and wheat head smut (Ubberella) of wheat, Glume blight (wheat glume blight), yellow spot (brown spot trichotheci-repenis), seedling blight (Rhizoctonia solani) caused by Rhizoctonia, and seedling blight (Gaeumannomyces graminis); powdery mildew of barley (Blumeria graminis) gibberellic disease (Fusarium graminearum), Fusarium avenaceum (Fusarium avenaceum), Fusarium culmorum (Fusarium culmorum), Microdochium nivale (Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia horneri), yellow rust (barley Puccinia horneri), loose black smut (Ustilago nuda), leaf blotch (rhynchophorus secalis), net blotch (barley net blotch (Pyrenophora teres)), spot disease (Cochliobolus citricola (Cochliobolus sativus)), leaf blotch (Pyrenophora graminea), alternaria leaf spot (Japanese: ラムラリアリーフスポット disease) (Ramularia collo-cygni), seedling blight (Rhizoctonia solani) caused by Rhizoctonia solani; rust of corn (maize rust (Puccinia sorghi)), southern rust (Puccinia polyspora), northern leaf spot (septoria turcica)), tropical rust (maize husk rust (phytopella zeae)), sesame leaf blight (Cochliobolus heterospirospora (Cochliobolus heterosporus)), anthracnose (Colletotrichum graminearum), gray spot (Cercospora zeae-maydis), brown spot (maize hypocrea (Kabatiella zeae)), ascosphaera leaf spot (maize hypocrella zeae), sclerotinia leaf spot (maize cryptophyma graminearum (phaeophyceae)), Fusarium graminearum (Fusarium graminearum), maize husk (Stenocarpella maculatum), maize stalk (Stenocarpella maculata), Fusarium graminearum (Fusarium graminearum), Fusarium graminearum (Fusarium graminearum); anthracnose of cotton (Colletotrichum gossypii)), white mold (septoria gossypii (Ramularia areola)), black spot (Alternaria macrospora (Alternaria macrocarpa), Alternaria gossypii (Alternaria gossypii), rhizoctonia solani (Thielaviopsis) caused by bacteria of the genus rhizoctonia (Thielaviopsis) (moniliforme radicicola)); rust of coffee (camelina rust (Hemileia vastatrix)), leaf spot (Cercospora coffeicola)); sclerotinia sclerotiorum (Sclerotinia sclerotiorum), Alternaria alternata (Alternaria brassica), and root rot disease (Phoma brassicae); rust disease of sugarcane (Puccinia melanothecella, Puccinia cruentesis (Puccinia kuehn)); rust disease of sunflower (sunflower rust (Puccinia helionthi)), dew spot (Plasmopara halstedii); citrus black spot disease (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum), Penicillium italicum (Penicillium italicum), blight (Phytophthora parasitica), Phytophthora citri (Phytophthora citri) and citrus brown rot (Phytophthora citri); apple blossom blight (sclerotinia mali), apple rot (apple Cladosporium), powdery mildew (Podosphaera leucotricha), Alternaria leaf spot (Alternaria alternata apple pathotype), scab (Venturia nigra), anthracnose (Glomella circinelloidis), Alternaria leaf spot (Diplocarpus mali), ring spot (botrytis cinerea), phytophthora blight (Phytophthora rosea), apple scab (Phanerochaeta), apple scab (Phanerochaete purpurea), ring spot (Phanerochaete chrysosporium), phytophthora blight (Phytophthora infestans), pear scab (Phanerium nipponensis), apple scab (Phanerium roseum), pear scab (Pseudoperonospora japonica), apple scab (Monilinia fructicola), apple scab (Solanum fructicola), apple scab (Monilinia fructicola), apple scab (Gray), apple scab (apple scab), apple scab (Gray), apple scab (apple scab), apple scab (Gray) and apple scab) of pear scab (Gray), apple scab (leaf spot (Gray, apple scab) of pear, apple scab (Gray, apple scab) and apple scab (leaf spot (Gray, apple scab) of the fungus (Gray, apple scab) of pear, apple scab, phoma rot disease (phoma sp.); anthracnose of grapes (Elsinoe ampelina), late blight (Glomeella cingulata), powdery mildew (Uncinula necator), rust (Puccinia ampelinalis), black rot (Staphylococcus coccinellii), and dew fungus (Plasmopara viticola); anthracnose of persimmon (Gloeosporium kaki), defoliation (Cercospora kaki), and coccobacillus kaki (mycosphaera nawae); anthracnose of cucurbits (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy stem blight (dimymella bryoniae), brown spot (corynebacterium crenatum), Fusarium oxysporum (Fusarium oxysporum), blight (Pseudoperonospora cubensis), Phytophthora blight (Phytophthora sp.) and seedling blight (Pythium sp.); tomato ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), coal mold (Pseudocercospora furigena), blight (Phytophthora infestans), powdery mildew (levulinella taurica), tomato ring rot (Alternaria solani); brown spot of eggplant (Phomopsis fulva (Phomopsis vexans)), powdery mildew of Compositae (Erysiphe cichororaceae); black spot disease (Alternaria japonica), white spot disease (Cercosporella brassiccus), clubroot disease (Plasmodiophora brassicae), and blight (Peronospora parastica) of cruciferous vegetables; rust disease of welsh onion (Puccinia allii)); soybean purpura (Cercospora kikuchi), anthracnose (Elsinoe glycine), anthracnose (trichoderma reesei), rust (Phakopsora pachyrhizi), brown ring rot (corynebacterium crenatum), anthracnose (hypochondrium japonicum), anthracnose (colcotrichum lucidum), leaf rot (Rhizoctonia solani), brown rot (Septoria), Septoria fulvidrosa (Septoria), blight (Cercospora fulvorum), soybean Cercospora (Cercospora), Fusarium solani (Cercospora solani), soybean powdery mildew (Fusarium solani), sclerotiorhii (sclerotiorum japonicum), soybean powdery mildew (Fusarium solani), sclerotiorhium (sclerotiorum), soybean powdery mildew (sclerotium niponicium japonicum), soybean powdery mildew (Fusarium solani); sclerotinia sclerotiorum (Sclerotinia sclerotiorum), rust (puccinia striiformis (u.rolomyces apendiculus)), keratoderma (phaeoeiseria fusca (phaseolitoria griseola)), anthracnose (Colletotrichum phaseolorum linoides (Colletotrichum linoides)); alternaria alternata (Cercospora personata), Cercospora brown spot (Cercospora arachidicola), sclerotinia sclerotiorum (sclerotinia rolfsii)) of peanuts; powdery mildew of peas (Erysiphe pisi); potato blight (Alternaria solani), blight (Phytophthora infestans), red rot (phomophora erythraea), powdery scab (Spongospora subsquens f.sp.suberanea), Verticillium wilt (Verticillium albo-atrum), Verticillium dahliae (Verticillium dahliae), and Verticillium nigrum (Verticillium nigrum)); powdery mildew of strawberries (Sphaerotheca gracilis (Sphaerotheca humuli)); tea tree netcake disease (Exobasidium reticulatum), alternaria blankii (Elsinoe leucospila), alternaria alternate (Pestalotiopsis sp.), anthracnose (Colletotrichum theae-sinensis)); alternaria longissima (Alternaria longissima), anthracnose (Colletotrichum tabacum), mycosis exposure (Peronospora tabacum), and Phytophthora blight (Phytophthora nicotianae); brown spot of sugar beet (Cercospora betanae)), leaf rot (dermataceae), root rot (dermataceae), black root (sapling rot (Aphanomyces cochlioides), rust (rust of sugar beet (Uromyces betae)); scab of rose (Diplocarpon rosa), powdery mildew (sphacelotheca rosea); brown spot of chrysanthemum (Septoria chrysosporium-indicii), white rust (horiba horizontalis (Puccinia horiana)); white spot blight of onion (Botrytis cinerea ), Botrytis squamosa, Botrytis cinerea), Botrytis cinerea, sclerotinia rot of small bacteria (Botrytis cinerea); sclerotinia sclerotiorum (Sclerotinia sclerotiorum) of various crops; alternaria brassicae (Alternaria brassicola); alternaria leaf spot (sclerotium homoeocarpa) of turfgrass, brown spot and megaspot (Rhizoctonia solani) of turfgrass; and leaf spot of banana (Mycosphaerella filensis, Mycosphaerella xanthophylla, Mycosphaerella musicola).
Seed diseases or diseases in the early growth stage of various crops are caused by a bacterium belonging to the genera Aspergillus (Aspergillus), Penicillium (Penicillium), Fusarium (Fusarium), Gibberella (Gibberella), trichoderma (Tricoderma), Rhizopus (Thielaviopsis), Rhizopus (Rhizopus), Mucor (Mucor), coriolus (coricium), Phoma, Rhizoctonia (Rhizoctonia), and Diplodia (Diplodia). Viral diseases of various crops are mediated by the genera polymyxa (Polymixa) and oleaster (Olpidium).
Seedling blight of rice (Burkholderia plantarii)); spotted bacterial disease of cucumber (Pseudomonas syringae cucumber pathovar syringae pv. lachrymans)); eggplant bacterial wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citri)); soft rot of Chinese cabbage (Erwinia carotovora), and the like.
The method for controlling a plant disease of the present invention includes, for example, treatments of plant bodies such as stem and leaf spreading and seed disinfection; soil treatment, etc. for the cultivation site of the plant.
For the treatment of Compound A, at a rate of every 1000m2Usually 1 to 10000 g. When the compound a is formulated into a preparation such as an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the concentration of the active ingredient is 0.01 to 10000ppm and then applied, and granules, powders, etc. are usually applied directly.
The composition of the present invention can be used as a control agent for plant diseases in agricultural fields such as upland fields, paddy fields, lawns, fruit tree gardens and the like.
Examples
The present invention will be described in further detail below with reference to production examples, test examples, and the like, but the present invention is not limited to these examples.
First, an example of production of compound a is given.
Step 1 of
A1L autoclave was charged with 84.0g of 6-chloro-3- (ethylsulfonyl) -N- [ 2-hydroxy-5- (trifluoromethanesulfonyl) phenyl ] pyridine-2-carboxamide, 183.6g of N-methyl-2-pyrrolidone, and 325g of 28% aqueous ammonia, which were produced by the method described in U.S. Pat. No. 2017/0158682, under a nitrogen atmosphere, sealed, and reacted at 75 to 80 ℃ for 8 hours. The obtained mixture was transferred to a 1L round bottom flask, and stirred at 50 ℃ under reduced pressure to remove dissolved gases. After cooling to room temperature, 339g of 1N hydrochloric acid was added. The obtained solid was filtered, and the filtrate was washed with water and toluene in this order and dried under reduced pressure to obtain 70.38g of intermediate A represented by the following formula.
[ solution 4]
An intermediate A:1H-NMR(DMSO-d6)δ(ppm):12.20(1H，br s)，10.05(1H，s)，8.79(1H，d)，7.84(1H，d)，7.78(1H，dd)，7.29(2H，s)，7.27(1H，d)，6.65(1H，d)，3.47(2H，q)，1.15(3H，t).
step 2
A mixture of 9.71g of intermediate A, 12.22g of p-toluenesulfonic acid monohydrate, and 100g of chlorobenzene was stirred under reflux for 98 hours while removing the produced water from the system using a Dean-Stark apparatus under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to 24.42g of a 20% aqueous potassium carbonate solution, and subjected to liquid separation. The resulting organic layer was washed with 10% aqueous potassium carbonate solution and water in this order, and concentrated under reduced pressure. The residue was brought to 80 ℃ and 14.57g of heptane was added dropwise to precipitate crystals. After cooling the mixture containing the obtained crystals to 5 ℃, filtration was performed. The resulting crystals were washed with 19.4g of 50% chlorobenzene/heptane and dried under reduced pressure to obtain 6.94g of compound A.
Preparation of Compound A1The H-NMR data are shown below.
1H-NMR(CDCl3)δ(ppm):8.76(1H，d)，8.36(1H，d)，8.30(1H，dd)，7.99(1H，d)，7.54(2H，s)，6.82(1H，d)，3.63(2H，q)，1.23(3H，t).
Then, test examples are given.
Test example 1
Soil was filled in a plastic pot, tomatoes (variety: Patio (Japanese text: パティオ)) were sown therein, and the pots were cultivated in a greenhouse for 19 days. A mixture (weight ratio 1: 1) of ammonium polyoxyethylene alkylether sulfate and wet silica 35 parts, compound a 20 parts, and water 45 parts were thoroughly mixed. The resulting mixture was diluted with water to prepare a diluted solution containing 125ppm of compound a. The diluted solution is spread on the leaf surface of the tomato in a sufficient adhesion manner. After the spread, the plants were air-dried, and 1 day later, an aqueous suspension containing spores of Alternaria solani (Alternaria solani) in which the 129 th amino acid residue of cytochrome b was replaced from phenylalanine to leucine was spray-inoculated. Thereafter, the tomatoes were left under the condition of 15 ℃ for more than moisture for 6 days, and the areas of the lesions were investigated. As a result, the lesion area of the tomatoes treated with compound a was 10% or less of the lesion area of the untreated tomatoes. The term "untreated" means that the diluent is not dispersed.
Comparative test example 1
The test was carried out in accordance with test example 1 using compound B in place of compound A. As a result, the lesion area of the tomatoes treated with compound B was 75% or more of the lesion area of the untreated tomatoes.
Comparative test example 2
The test was carried out in accordance with test example 1 using compound C in place of compound A. As a result, the lesion area of the tomatoes treated with compound C was 75% or more of the lesion area of the untreated tomatoes.
Industrial applicability
Compound a exhibits an excellent control effect on plant diseases.
Claims (3)
1. A compound represented by formula (a):
2. a composition comprising a compound of claim 1 and an inactive carrier.
3. A method for controlling a plant disease, which comprises treating a plant or soil with an effective amount of the compound according to claim 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018-153852 | 2018-08-20 | ||
| JP2018153852 | 2018-08-20 | ||
| PCT/JP2019/032234 WO2020040075A1 (en) | 2018-08-20 | 2019-08-19 | Benzoxazole compound and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112236427A true CN112236427A (en) | 2021-01-15 |
| CN112236427B CN112236427B (en) | 2023-10-03 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201980038344.2A Active CN112236427B (en) | 2018-08-20 | 2019-08-19 | Benzoxazole compounds and uses thereof |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP7254084B2 (en) |
| KR (1) | KR20210046593A (en) |
| CN (1) | CN112236427B (en) |
| TW (1) | TWI800674B (en) |
| WO (1) | WO2020040075A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112673006A (en) * | 2018-09-13 | 2021-04-16 | 住友化学株式会社 | Bipyridine compound and use thereof |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0710840A (en) * | 1993-06-23 | 1995-01-13 | Mitsubishi Chem Corp | Sulfide derivative, bactericidal agent using the same as effective component and intermediate therefor |
| US20100249077A1 (en) * | 2007-12-05 | 2010-09-30 | Basf Se | Pyridylmethyl-Sulfonamide Compounds |
| EP2345328A1 (en) * | 2008-09-19 | 2011-07-20 | Sumitomo Chemical Company, Limited | Composition for agricultural use |
| WO2015068773A1 (en) * | 2013-11-08 | 2015-05-14 | 石原産業株式会社 | Nitrogen-containing saturated heterocyclic compound |
| US20150313234A1 (en) * | 2012-12-27 | 2015-11-05 | Sumitomo Chemical Company, Limited | Fused heterocyclic compound and use thereof for pest control |
| CN105358555A (en) * | 2013-07-01 | 2016-02-24 | 住友化学株式会社 | Fused heterocyclic compound and pest control use thereof |
| JPWO2014065411A1 (en) * | 2012-10-26 | 2016-09-08 | 株式会社エス・ディー・エス バイオテック | Sulfonamide derivatives as pest control agents for agriculture and horticulture |
| CN108349970A (en) * | 2015-11-05 | 2018-07-31 | 住友化学株式会社 | Condensed heterocyclic compouds |
| CN108401430A (en) * | 2015-12-16 | 2018-08-14 | 住友化学株式会社 | 2- (3- b sulfonyl pyridine -2- bases) -5- (trifyl) benzo * azoles crystal |
-
2019
- 2019-08-16 TW TW108129264A patent/TWI800674B/en active
- 2019-08-19 JP JP2020538370A patent/JP7254084B2/en active Active
- 2019-08-19 CN CN201980038344.2A patent/CN112236427B/en active Active
- 2019-08-19 KR KR1020207037698A patent/KR20210046593A/en unknown
- 2019-08-19 WO PCT/JP2019/032234 patent/WO2020040075A1/en active Application Filing
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0710840A (en) * | 1993-06-23 | 1995-01-13 | Mitsubishi Chem Corp | Sulfide derivative, bactericidal agent using the same as effective component and intermediate therefor |
| US20100249077A1 (en) * | 2007-12-05 | 2010-09-30 | Basf Se | Pyridylmethyl-Sulfonamide Compounds |
| EP2345328A1 (en) * | 2008-09-19 | 2011-07-20 | Sumitomo Chemical Company, Limited | Composition for agricultural use |
| JPWO2014065411A1 (en) * | 2012-10-26 | 2016-09-08 | 株式会社エス・ディー・エス バイオテック | Sulfonamide derivatives as pest control agents for agriculture and horticulture |
| US20150313234A1 (en) * | 2012-12-27 | 2015-11-05 | Sumitomo Chemical Company, Limited | Fused heterocyclic compound and use thereof for pest control |
| CN105358555A (en) * | 2013-07-01 | 2016-02-24 | 住友化学株式会社 | Fused heterocyclic compound and pest control use thereof |
| WO2015068773A1 (en) * | 2013-11-08 | 2015-05-14 | 石原産業株式会社 | Nitrogen-containing saturated heterocyclic compound |
| CN108349970A (en) * | 2015-11-05 | 2018-07-31 | 住友化学株式会社 | Condensed heterocyclic compouds |
| CN108401430A (en) * | 2015-12-16 | 2018-08-14 | 住友化学株式会社 | 2- (3- b sulfonyl pyridine -2- bases) -5- (trifyl) benzo * azoles crystal |
Non-Patent Citations (4)
| Title |
|---|
| JONATHAN J. POWELL，ET AL.: ""The Fusarium crown rot pathogen Fusarium pseudograminearum triggers a suite of transcriptional and metabolic changes in bread wheat (Triticum aestivum L.)"", 《ANNALS OF BOTANY》, vol. 119, pages 853 - 867 * |
| 冯志君 等: ""2-芳基苯并噁唑的合成和生物活性"", 《皖南医学院学报》, vol. 31, no. 3, pages 180 - 182 * |
| 张翼翾: ""2-多氟苯基苯并曝唑衍生物的合成和杀螨活性"", 《世界农药》, vol. 25, no. 4, pages 12 - 17 * |
| 钟滨 等: ""2-取代苯并噁唑衍生物的合成及生物活性"", 《应用化学》, vol. 20, no. 7, pages 684 - 686 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112673006A (en) * | 2018-09-13 | 2021-04-16 | 住友化学株式会社 | Bipyridine compound and use thereof |
| CN112673006B (en) * | 2018-09-13 | 2024-05-03 | 住友化学株式会社 | Bipyridine compound and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP7254084B2 (en) | 2023-04-07 |
| JPWO2020040075A1 (en) | 2021-09-02 |
| TW202017920A (en) | 2020-05-16 |
| WO2020040075A1 (en) | 2020-02-27 |
| CN112236427B (en) | 2023-10-03 |
| KR20210046593A (en) | 2021-04-28 |
| TWI800674B (en) | 2023-05-01 |
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