KR20000067879A - 치환된 피라졸릴피라졸 유도체, 그 제조방법 및 그의 제초 효과 - Google Patents
치환된 피라졸릴피라졸 유도체, 그 제조방법 및 그의 제초 효과 Download PDFInfo
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- KR20000067879A KR20000067879A KR1019997000315A KR19997000315A KR20000067879A KR 20000067879 A KR20000067879 A KR 20000067879A KR 1019997000315 A KR1019997000315 A KR 1019997000315A KR 19997000315 A KR19997000315 A KR 19997000315A KR 20000067879 A KR20000067879 A KR 20000067879A
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- South Korea
- Prior art keywords
- alkyl
- hydrogen
- substituted
- formula
- halogen
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 12
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 10
- KFSUCTRGHQKXSV-UHFFFAOYSA-N 5-(1h-pyrazol-5-yl)-1h-pyrazole Chemical class N1N=CC=C1C1=CC=NN1 KFSUCTRGHQKXSV-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical group 0.000 claims description 13
- 241000196324 Embryophyta Species 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
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- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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- 239000003814 drug Substances 0.000 abstract 1
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- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 239000006028 limestone Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19630555.1 | 1996-07-18 | ||
| DE19630555A DE19630555A1 (de) | 1996-07-18 | 1996-07-18 | Substituierte Pyrazolyl-pyrazolderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20000067879A true KR20000067879A (ko) | 2000-11-25 |
Family
ID=7801171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019997000315A KR20000067879A (ko) | 1996-07-18 | 1997-07-07 | 치환된 피라졸릴피라졸 유도체, 그 제조방법 및 그의 제초 효과 |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0915873A1 (zh) |
| JP (1) | JP2000515142A (zh) |
| KR (1) | KR20000067879A (zh) |
| CN (1) | CN1225635A (zh) |
| AU (1) | AU4009497A (zh) |
| BR (1) | BR9710494A (zh) |
| CA (1) | CA2261125A1 (zh) |
| DE (1) | DE19630555A1 (zh) |
| ID (1) | ID17533A (zh) |
| PL (1) | PL331287A1 (zh) |
| TR (1) | TR199900065T2 (zh) |
| TW (1) | TW355124B (zh) |
| WO (1) | WO1998003506A1 (zh) |
| ZA (1) | ZA976329B (zh) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR097245A1 (es) * | 2013-08-09 | 2016-03-02 | Kyoyu Agri Co Ltd | Derivado de pirazolilpirazol sustituido y su empleo como herbicida |
| JP6128555B2 (ja) * | 2013-08-13 | 2017-05-17 | 協友アグリ株式会社 | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 |
| JP6097655B2 (ja) * | 2013-08-13 | 2017-03-15 | 協友アグリ株式会社 | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 |
| JP6128556B2 (ja) | 2013-08-13 | 2017-05-17 | 協友アグリ株式会社 | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 |
| AR103467A1 (es) * | 2015-01-23 | 2017-05-10 | Kyoyu Agri Co Ltd | Derivado de pirazolilpirazol sustituido y su empleo como herbicida |
| AR103472A1 (es) * | 2015-01-23 | 2017-05-10 | Kyoyu Agri Co Ltd | Derivado de pirazolilpirazol sustituido y su empleo como herbicida |
| AR103473A1 (es) * | 2015-01-23 | 2017-05-10 | Kyoyu Agri Co Ltd | Derivado de pirazolilpirazol sustituido y su empleo como herbicida |
| AR103469A1 (es) * | 2015-01-23 | 2017-05-10 | Kyoyu Agri Co Ltd | Derivado de pirazolilpirazol sustituido y su empleo como herbicida |
| AR103468A1 (es) * | 2015-01-23 | 2017-05-10 | Kyoyu Agri Co Ltd | Derivado de pirazolilpirazol sustituido y su empleo como herbicida |
| AR103470A1 (es) * | 2015-01-23 | 2017-05-10 | Kyoyu Agri Co Ltd | Derivado de pirazolilpirazol sustituido y su empleo como herbicida |
| CN107540670B (zh) * | 2016-06-23 | 2021-08-13 | 湖北相和精密化学有限公司 | 一种1-(3-氯吡唑并[1，5a]-4，5，6，7-四氢吡啶-2-基)-5-甲胺吡唑-4-甲腈的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL116507A (en) * | 1991-11-13 | 1997-08-14 | Schering Ag | Pyrazole derivatives |
| PL174304B1 (pl) * | 1992-10-12 | 1998-07-31 | Schering Ag | Podstawione pochodne pirazolu |
| DE4435373A1 (de) * | 1994-09-22 | 1996-03-28 | Hoechst Schering Agrevo Gmbh | Substituierte Pyrazolyl-pyrazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider Wirkung |
| DE19532347A1 (de) * | 1995-09-04 | 1997-03-06 | Bayer Ag | 4-Thiocarbamoyl-1-(3-pyrazolyl)-pyrazole |
-
1996
- 1996-07-18 DE DE19630555A patent/DE19630555A1/de not_active Withdrawn
-
1997
- 1997-07-07 EP EP97937465A patent/EP0915873A1/de not_active Withdrawn
- 1997-07-07 CN CN97196518A patent/CN1225635A/zh active Pending
- 1997-07-07 PL PL97331287A patent/PL331287A1/xx unknown
- 1997-07-07 KR KR1019997000315A patent/KR20000067879A/ko not_active Application Discontinuation
- 1997-07-07 TR TR1999/00065T patent/TR199900065T2/xx unknown
- 1997-07-07 WO PCT/EP1997/003570 patent/WO1998003506A1/de not_active Application Discontinuation
- 1997-07-07 JP JP10506487A patent/JP2000515142A/ja active Pending
- 1997-07-07 AU AU40094/97A patent/AU4009497A/en not_active Abandoned
- 1997-07-07 BR BR9710494A patent/BR9710494A/pt not_active Application Discontinuation
- 1997-07-07 CA CA002261125A patent/CA2261125A1/en not_active Abandoned
- 1997-07-10 ID IDP972404A patent/ID17533A/id unknown
- 1997-07-16 TW TW086110082A patent/TW355124B/zh active
- 1997-07-17 ZA ZA9706329A patent/ZA976329B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TR199900065T2 (xx) | 1999-04-21 |
| PL331287A1 (en) | 1999-07-05 |
| JP2000515142A (ja) | 2000-11-14 |
| EP0915873A1 (de) | 1999-05-19 |
| ZA976329B (en) | 1998-01-19 |
| CA2261125A1 (en) | 1998-01-29 |
| WO1998003506A1 (de) | 1998-01-29 |
| ID17533A (id) | 1998-01-08 |
| DE19630555A1 (de) | 1998-01-22 |
| CN1225635A (zh) | 1999-08-11 |
| TW355124B (en) | 1999-04-01 |
| BR9710494A (pt) | 1999-08-17 |
| AU4009497A (en) | 1998-02-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |