JPWO2018038192A1 - 3−ピリジルオキシフェニルジヒドロウラシル化合物及びその用途 - Google Patents
3−ピリジルオキシフェニルジヒドロウラシル化合物及びその用途 Download PDFInfo
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- 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
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 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
- 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
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-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
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical compound C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 244000000003 plant pathogen Species 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 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
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
本発明は3−ピリジルオキシフェニルジヒドロウラシル化合物及びその用途に関する。
液体担体としては、例えば、水、アルコール類(メタノール、エタノール等)、ケトン類(アセトン、メチルエチルケトン等)、芳香族炭化水素類(トルエン、キシレン、エチルベンゼン、メチルナフタレン等)、脂肪族炭化水素類(ヘキサン、シクロヘキサン、灯油等)、エステル類(酢酸エチル、酢酸ブチル等)、ニトリル類(アセトニトリル、イソブチルニトリル等)、エーテル類(ジイソプロピルエーテル等)、アミド類(ジメチルホルムアミド、ジメチルアセトアミド等)、及びスルホキシド類(ジメチルスルホキシド等)が挙げられる。
本発明の防除方法における本発明化合物の処理量は、処理する植物の種類、防除対象である植物病害の種類や発生頻度、製剤形態、処理時期、処理方法、処理場所、気象条件等によっても異なるが、植物の茎葉に処理する場合又は植物を栽培する土壌に処理する場合は、本発明化合物は、1000m2あたり、通常1〜500gである。
乳剤、水和剤、フロアブル剤等は通常水で希釈して散布することにより処理する。この場合、本発明化合物の濃度は、通常0.0005〜2重量%である。粉剤、粒剤等は通常希釈することなくそのまま処理する。
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);キュウリの灰色疫病(Phytophthora capsici)、苗立枯病(Pythium ultimum)および斑点細菌病(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。
1H−NMR (CDCl3, 23℃) δ(ppm): 7.90−7.89 (1H, m), 7.33−7.24 (2H, m), 7.18 (0.4H,br), 7.09 (0.6H,br), 7.01−6.88 (2H,m), 5.75 (0.4H,br), 4.99−4.84 (2H, m), 4.16 (2H, q, J = 7.0 Hz), 3.19−3.00 (2H, m), 2.42 (0.6H, br), 1.27 (3H, q, J = 7.0 Hz).
ESI−MS(posi):522[M+H]+
なお、試験例1〜4における無処理区とは、本発明化合物を含有するジメチルスルホキシド希釈液の代わりにジメチルスルホキシドを分注する以外は各々の試験例に記載されたのと同じ条件で行った試験区を表す。
本発明化合物4.5mgをジメチルスルホキシド100μLで希釈した。希釈液1μLをタイタープレート(96ウェル)に分注したのち、キュウリ灰色疫病菌(Phytophthora capsici)の遊走子を含むジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを3日間、27℃で培養してキュウリ灰色疫病菌を増殖させたのち、タイタープレートの各ウェルの600nmの吸光度を測定し、キュウリ灰色疫病菌の生育度とした。その生育度をもとに、「式1」を用いて効力を算出したところ、本発明化合物の効力は90%以上であった。
「式1」
効力=100×(X−Y)/X
X:無処理区の菌の生育度
Y:処理区の菌の生育度
本発明化合物4.5mgをジメチルスルホキシド100μLで希釈した。希釈液1μLをタイタープレート(96ウェル)に分注したのち、苗立枯病菌(Pythium ultimum)の菌糸懸濁液を含むツァペック培地を150μL分注した。このプレートを5日間、23℃で培養して苗立枯病菌を増殖させたのち、タイタープレートの各ウェルの600nmの吸光度を測定し、苗立枯病菌の生育度とした。その生育度をもとに、「式1」を用い効力を算出したところ、本発明化合物の効力は90%以上であった。
本発明化合物1.12mgをジメチルスルホキシド100μLで希釈した。希釈液1μLをタイタープレート(96ウェル)に分注したのち、苗立枯病菌(Pythium ultimum)の菌糸懸濁液を含むツァペック培地を150μL分注した。このプレートを5日間、23℃で培養して苗立枯病菌を増殖させたのち、タイタープレートの各ウェルの600nmの吸光度を測定し、苗立枯病菌の生育度とした。その生育度をもとに、「式1」を用い効力を算出したところ、本発明化合物の効力は90%以上であった。
本発明化合物4.5mgをジメチルスルホキシド100μLで希釈した。希釈液1μLをタイタープレート(96ウェル)に分注したのち、あらかじめオオムギ雲形病菌(Rhynchosporium secalis)の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを7日間、18℃で培養してオオムギ雲形病菌を増殖させたのち、タイタープレートの各ウェルの600nmの吸光度を測定し、オオムギ雲形病菌の生育度とした。その生育度をもとに、「式1」を用いて効力を算出したところ、本発明化合物の効力は90%以上であった。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH10500116A (ja) * | 1994-05-18 | 1998-01-06 | バイエル・アクチエンゲゼルシヤフト | 置換されたジアザシクロヘキサンジ(チ)オン |
JP2001316375A (ja) * | 1999-11-01 | 2001-11-13 | Sumitomo Chem Co Ltd | 6−ヒドロキシ−5,6−ジヒドロウラシル化合物 |
JP2002155061A (ja) * | 2000-02-04 | 2002-05-28 | Sumitomo Chem Co Ltd | ウラシル化合物及びその用途 |
WO2002098227A1 (en) * | 2001-05-31 | 2002-12-12 | Sumitomo Chemical Company, Limited | Plant growth regulators for cotton hervest |
WO2002098228A1 (fr) * | 2001-05-31 | 2002-12-12 | Sumitomo Chemical Company, Limited | Agent dessicatif pour tiges et feuilles |
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DE60041110D1 (de) * | 1999-11-01 | 2009-01-29 | Sumitomo Chemical Co | 6-Hydroxy-5,6-dihydrouracile als Herbizide |
JP2016165426A (ja) | 2015-03-10 | 2016-09-15 | 三晃合成工業株式会社 | 液体吸引具 |
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JPH10500116A (ja) * | 1994-05-18 | 1998-01-06 | バイエル・アクチエンゲゼルシヤフト | 置換されたジアザシクロヘキサンジ(チ)オン |
JP2001316375A (ja) * | 1999-11-01 | 2001-11-13 | Sumitomo Chem Co Ltd | 6−ヒドロキシ−5,6−ジヒドロウラシル化合物 |
JP2002155061A (ja) * | 2000-02-04 | 2002-05-28 | Sumitomo Chem Co Ltd | ウラシル化合物及びその用途 |
WO2002098227A1 (en) * | 2001-05-31 | 2002-12-12 | Sumitomo Chemical Company, Limited | Plant growth regulators for cotton hervest |
WO2002098228A1 (fr) * | 2001-05-31 | 2002-12-12 | Sumitomo Chemical Company, Limited | Agent dessicatif pour tiges et feuilles |
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AR109409A1 (es) | 2018-11-28 |
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WO2018038192A1 (ja) | 2018-03-01 |
CN109641872B (zh) | 2021-01-19 |
CN109641872A (zh) | 2019-04-16 |
DE112017004257T5 (de) | 2019-05-16 |
US20190183123A1 (en) | 2019-06-20 |
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