JPWO2020054790A1 - ビピリジン化合物及びその用途 - Google Patents
ビピリジン化合物及びその用途 Download PDFInfo
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- JPWO2020054790A1 JPWO2020054790A1 JP2020546065A JP2020546065A JPWO2020054790A1 JP WO2020054790 A1 JPWO2020054790 A1 JP WO2020054790A1 JP 2020546065 A JP2020546065 A JP 2020546065A JP 2020546065 A JP2020546065 A JP 2020546065A JP WO2020054790 A1 JPWO2020054790 A1 JP WO2020054790A1
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- 229940077388 benzenesulfonate Drugs 0.000 description 1
- CURLHBZYTFVCRG-UHFFFAOYSA-N butan-2-yl n-(3-chlorophenyl)carbamate Chemical compound CCC(C)OC(=O)NC1=CC=CC(Cl)=C1 CURLHBZYTFVCRG-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 208000032625 disorder of ear Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002333 glycines Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920005671 poly(vinyl chloride-propylene) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
本発明はビピリジン化合物及びその用途に関する。
本発明の組成物は、化合物Aを通常0.0001〜95重量%含有する。
Aspergillus属、Penicillium属、Fusarium属、Gibberella属、Tricoderma属、Thielaviopsis属、Rhizopus属、Mucor属、Corticium属、Phoma属、Rhizoctonia属、及びDiplodia属菌等によって引き起こされる、各種作物の種子病害又は生育初期の病害。Polymixa属又はOlpidium属等によって媒介される各種作物のウイルス病。
イネの苗立枯細菌病(Burkholderia plantarii);キュウリの斑点細菌病(Pseudomonas syringae pv. lachrymans);ナスの青枯病(Ralstonia solanacearum)、カンキツのかいよう病(Xanthomonas citiri);ハクサイの軟腐病(Erwinia carotovora)等。
窒素雰囲気下で、100mLオートクレーブに米国特許第9850209号明細書に記載の方法で製造した6−クロロ−3−(エタンスルホニル)ピリジン−2−カルボン酸8.58g、メタノール25.3g、炭酸水素カリウム6.98g、及び5%Pd/炭素0.22gを加え、密閉した後、水素雰囲気下で45時間反応させた。得られた混合物をろ過し、ろ物をメタノール及び水で順次洗浄した。得られた水洗浄液に35%塩酸を加えて中和した。得られた固体をろ過し、水で洗浄し、乾燥して、下式で示される中間体Aを0.32g得た。
塩化チオニル1.39g、キシレン49.72g、及びN,N−ジメチルホルムアミド0.04gの混合物に、60℃で3.79gの中間体A及びキシレン5.52gの混合物を加え、60℃で5.5時間撹拌した。得られた混合物に塩化チオニル2.84gを加え、60℃で7時間撹拌した。得られた混合物を室温にした後、減圧下で濃縮した。得られた残さを、米国特許第8426443号明細書に記載の方法で製造した2−アミノ−4−(トリフルオロメタンスルホニル)フェノール4.20g及びテトラヒドロフラン12.54gの混合物に加え、次にテトラヒドロフラン35.10g及びキシレン34.11gを順次加え、60℃で2時間撹拌した。得られた混合物に水24.94g、テトラヒドロフラン19.36g、及び27%水酸化ナトリウム水溶液1.88gの混合物を60℃で加えて、pHを5.3に調整した。得られた混合物を5℃に冷却し、得られた結晶をろ過した。ろ物を水、キシレン、及び50%キシレン/テトラヒドロフラン溶液で順次洗浄し、乾燥して、下式で示される中間体Bを6.35g得た。
3.08gの中間体B、キシレン335g、及びp−トルエンスルホン酸一水和物33.71gの混合物を、還流下で、ディーンスターク装置を用いて生成した水を系外に除去しながら69時間撹拌した。得られた混合物を100℃に冷却した後、室温の20%炭酸カリウム水溶液92.5gに加え、80℃で撹拌した。析出した固体をろ過し、ろ物を水及びキシレンで順次洗浄し、乾燥した。得られた固体を室温でN,N−ジメチルホルムアミド1000gに溶解させた後、水100gを滴下した。得られた固体をろ過し、ろ物をN,N−ジメチルホルムアミド及び水で順次洗浄し、乾燥して、化合物Aを0.83g得た。
化合物Aの1H-NMRデータを以下に示す。
1H-NMR (N,N−ジメチルホルムアミド-d7) δ(ppm): 9.11 (2H, d), 8.95 (2H, d), 8.93 (2H, d), 8.55 (2H, d), 8.46 (2H, dd), 4.04 (4H, q), 1.40 (6H, m).
プラスチックポットに土壌を詰め、そこにトマト(品種:パティオ)を播種し、温室内で19日間栽培した。ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩と湿式シリカとの混合物(重量比1:1)35重量部、化合物A20重量部、及び水45重量部を十分に混合した。得られた混合物を水で希釈して、化合物Aを125ppm含有する希釈液を調製した。この希釈液を、上記トマトの葉面に充分付着するように散布した。散布後トマトを風乾し、1日後にトマト輪紋病菌(チトクロームbの129番目のアミノ酸残基がフェニルアラニンからロイシンに置換したAlternaria solani)胞子を含む水懸濁液を噴霧接種した。その後、トマトを15℃多湿下に6日間置き、病斑面積を調査した。その結果、化合物Aを処理したトマトにおける病斑面積は、無処理のトマトにおける病斑面積の0%であった。なお、無処理とは、上記希釈液を散布しなかったことを意味する。
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