KR102497895B1 - 아졸 유도체, 아졸 유도체의 제조 방법, 및 농원예용 약제 및 공업용 재료 보호제 - Google Patents
아졸 유도체, 아졸 유도체의 제조 방법, 및 농원예용 약제 및 공업용 재료 보호제 Download PDFInfo
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- KR102497895B1 KR102497895B1 KR1020227030308A KR20227030308A KR102497895B1 KR 102497895 B1 KR102497895 B1 KR 102497895B1 KR 1020227030308 A KR1020227030308 A KR 1020227030308A KR 20227030308 A KR20227030308 A KR 20227030308A KR 102497895 B1 KR102497895 B1 KR 102497895B1
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- compound
- azole derivative
- methyl
- added
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- 150000007980 azole derivatives Chemical class 0.000 title claims description 101
- 239000012770 industrial material Substances 0.000 title claims description 14
- 239000003223 protective agent Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title description 52
- 229940079593 drug Drugs 0.000 title description 13
- 239000003814 drug Substances 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 176
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 11
- -1 alkali metal salt Chemical class 0.000 claims description 151
- 239000004480 active ingredient Substances 0.000 claims description 34
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
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- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
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- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 235000011181 potassium carbonates Nutrition 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
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- 240000005979 Hordeum vulgare Species 0.000 description 10
- 235000007340 Hordeum vulgare Nutrition 0.000 description 10
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000000969 carrier Substances 0.000 description 10
- 150000002576 ketones Chemical class 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 6
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Classifications
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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
- A01N43/48—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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| JP2020039353 | 2020-03-06 | ||
| JPJP-P-2020-039353 | 2020-03-06 | ||
| PCT/JP2021/008690 WO2021177442A1 (ja) | 2020-03-06 | 2021-03-05 | アゾール誘導体、アゾール誘導体の製造方法、ならびに農園芸用薬剤および工業用材料保護剤 |
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| KR20220129652A KR20220129652A (ko) | 2022-09-23 |
| KR102497895B1 true KR102497895B1 (ko) | 2023-02-08 |
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| WO2023033180A1 (ja) * | 2021-09-06 | 2023-03-09 | 株式会社クレハ | アゾール誘導体のｒ－エナンチオマー、農園芸用薬剤および工業用材料保護剤 |
| CN114262250A (zh) * | 2021-12-24 | 2022-04-01 | 乐威医药（江苏）股份有限公司 | 芳香环苄基邻位双烷基的合成方法 |
| CN119504731A (zh) * | 2024-11-14 | 2025-02-25 | 广东省科学院测试分析研究所(中国广州分析测试中心) | 一类含1,3,4-噁二唑酰腙结构的柚皮素衍生物及其制备方法 |
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| US4413003A (en) * | 1977-07-29 | 1983-11-01 | Rohm And Haas Company | β-Hydroxyarylethylimidazoles |
| DE3608144A1 (de) * | 1986-03-12 | 1987-09-24 | Hoechst Ag | Aryl-azolylmethyl-benzocycloalken-derivate, verfahren zu ihrer herstellung und ihre verwendung |
| GB8705174D0 (en) * | 1987-03-05 | 1987-04-08 | Ici Plc | Heterocyclic compounds |
| JP4161331B2 (ja) * | 1997-09-02 | 2008-10-08 | 株式会社クレハ | アゾリルメチルビシクロヘキサノール誘導体、その製造方法及び、農薬並びに、医薬としての利用 |
| US20030166476A1 (en) | 2002-01-31 | 2003-09-04 | Winemiller Mark D. | Lubricating oil compositions with improved friction properties |
| JP2012501294A (ja) * | 2008-08-26 | 2012-01-19 | 株式会社クレハ | ５−ベンジル−４−アゾリルメチル−４−スピロ［２．４］ヘプタノール誘導体、その製造方法、農園芸用薬剤および工業用材料保護剤 |
| UA108867C2 (uk) * | 2009-12-08 | 2015-06-25 | Похідні азолу, спосіб їх одержання (варіанти), проміжні продукти, засіб для сільського господарства і садівництва | |
| KR101464420B1 (ko) * | 2009-12-08 | 2014-11-21 | 가부시끼가이샤 구레하 | 아졸 유도체 및 그의 제조 방법, 상기 유도체의 중간체 화합물 및 그의 제조 방법, 및 상기 유도체를 함유하는 농원예용 약제 및 공업용 재료 보호제 |
| CA2838586C (en) * | 2011-06-07 | 2016-10-11 | Kureha Corporation | Azole derivative, method for producing same, intermediate compound, and agricultural or horticultural chemical agent and industrial material protecting agent |
| DK2731935T3 (en) * | 2011-07-13 | 2016-06-06 | Basf Agro Bv | FUNGICIDE SUBSTITUTED 2- [2-HALOGENALKYL-4- (PHENOXY) -PHENYL] -1- [1,2,4] TRIAZOL-1-YLETHANOL COMPOUNDS |
| PT3712135T (pt) | 2017-11-13 | 2023-07-07 | Kureha Corp | Derivado de azol, composto intermediário, método de produção de derivado de azol, agente para utilização agrícola e hortícola e agente de proteção de materiais para utilização industrial |
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| WO2021177442A1 (ja) | 2021-09-10 |
| CA3170548A1 (en) | 2021-09-10 |
| CN115052863A (zh) | 2022-09-13 |
| BR112022017644A2 (pt) | 2022-10-18 |
| AU2021230953B2 (en) | 2022-10-06 |
| CR20220440A (es) | 2022-12-06 |
| MX2022010857A (es) | 2023-03-14 |
| EP4116292A1 (en) | 2023-01-11 |
| PH12022552096A1 (en) | 2023-11-29 |
| JPWO2021177442A1 (https=) | 2021-09-10 |
| AU2021230953A1 (en) | 2022-09-22 |
| IL295773B2 (en) | 2023-04-01 |
| IL295773A (en) | 2022-10-01 |
| US20230192630A1 (en) | 2023-06-22 |
| KR20220129652A (ko) | 2022-09-23 |
| NZ792521A (en) | 2023-01-27 |
| ECSP22077395A (es) | 2022-11-30 |
| BR112022017644B1 (pt) | 2023-05-02 |
| IL295773B (en) | 2022-12-01 |
| JP7150213B2 (ja) | 2022-10-07 |
| CN115052863B (zh) | 2023-04-28 |
| CL2022002418A1 (es) | 2023-04-14 |
| CO2022013071A2 (es) | 2022-09-20 |
| AR121486A1 (es) | 2022-06-08 |
| UA127256C2 (uk) | 2023-06-21 |
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