CA1067907A - Herbicidal 1,4-diphenyl-3-pyrazolin-5-ones - Google Patents
Herbicidal 1,4-diphenyl-3-pyrazolin-5-onesInfo
- Publication number
- CA1067907A CA1067907A CA264,490A CA264490A CA1067907A CA 1067907 A CA1067907 A CA 1067907A CA 264490 A CA264490 A CA 264490A CA 1067907 A CA1067907 A CA 1067907A
- Authority
- CA
- Canada
- Prior art keywords
- pyrazolin
- alpha
- tolyl
- trifluoro
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- XNWYPYFQYFUUTE-UHFFFAOYSA-N 2,4-diphenyl-1h-pyrazol-3-one Chemical class O=C1C(C=2C=CC=CC=2)=CNN1C1=CC=CC=C1 XNWYPYFQYFUUTE-UHFFFAOYSA-N 0.000 title abstract 2
- 230000002363 herbicidal effect Effects 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 241000196324 Embryophyta Species 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 8
- -1 chloro, fluoro, bromo, methyl Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- KBRQEEHDWOQDES-UHFFFAOYSA-N 2,4-bis(3-chlorophenyl)-1-ethylpyrazol-3-one Chemical compound O=C1N(C=2C=C(Cl)C=CC=2)N(CC)C=C1C1=CC=CC(Cl)=C1 KBRQEEHDWOQDES-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 abstract description 18
- 239000004009 herbicide Substances 0.000 abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 238000012360 testing method Methods 0.000 description 22
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
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- 238000010992 reflux Methods 0.000 description 14
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 9
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 5
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- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 description 4
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- DHUVVGKLKWHBSO-UHFFFAOYSA-N 2-(3-chlorophenyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC(Cl)=C1 DHUVVGKLKWHBSO-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- CRRIAWUJYMLJOE-UHFFFAOYSA-N (3-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(Cl)=C1 CRRIAWUJYMLJOE-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
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- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- 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 2
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- FEKUXLUOKFSMRO-UHFFFAOYSA-N (4-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(F)C=C1 FEKUXLUOKFSMRO-UHFFFAOYSA-N 0.000 description 1
- DIYDSENGHGGDSE-UHFFFAOYSA-N 1-ethyl-4-(3-methylphenyl)-2-phenylpyrazol-3-one Chemical compound O=C1N(C=2C=CC=CC=2)N(CC)C=C1C1=CC=CC(C)=C1 DIYDSENGHGGDSE-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
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- LSRUOHOVDCISNX-UHFFFAOYSA-N 2,4-bis(3-chlorophenyl)-1h-pyrazol-3-one Chemical compound ClC1=CC=CC(C=2C(N(C=3C=C(Cl)C=CC=3)NC=2)=O)=C1 LSRUOHOVDCISNX-UHFFFAOYSA-N 0.000 description 1
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- 238000004452 microanalysis Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63974475A | 1975-12-11 | 1975-12-11 | |
| US05/724,502 US4075003A (en) | 1975-12-11 | 1976-09-20 | Novel herbicidal method utilizing 1,4-diphenyl-3-pyrazolin-5-ones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067907A true CA1067907A (en) | 1979-12-11 |
Family
ID=27093389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA264,490A Expired CA1067907A (en) | 1975-12-11 | 1976-10-29 | Herbicidal 1,4-diphenyl-3-pyrazolin-5-ones |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS6033112B2 (cs) |
| AR (1) | AR218861A1 (cs) |
| AT (1) | AT354434B (cs) |
| AU (1) | AU507882B2 (cs) |
| BG (1) | BG27547A3 (cs) |
| CA (1) | CA1067907A (cs) |
| CH (1) | CH622784A5 (cs) |
| CS (1) | CS186746B2 (cs) |
| DD (1) | DD129326A5 (cs) |
| DE (1) | DE2651008A1 (cs) |
| DK (1) | DK550876A (cs) |
| ES (1) | ES454061A1 (cs) |
| FR (1) | FR2334674A1 (cs) |
| GB (1) | GB1570623A (cs) |
| GR (1) | GR63123B (cs) |
| IE (1) | IE43807B1 (cs) |
| IL (1) | IL50792A (cs) |
| IT (1) | IT1123686B (cs) |
| MX (1) | MX3832E (cs) |
| NL (1) | NL7613810A (cs) |
| NZ (1) | NZ182530A (cs) |
| PH (1) | PH13076A (cs) |
| PL (1) | PL106071B1 (cs) |
| PT (1) | PT65890B (cs) |
| RO (1) | RO72400B (cs) |
| SE (1) | SE430413B (cs) |
| SU (1) | SU643083A3 (cs) |
| ZA (1) | ZA766561B (cs) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8252817B2 (en) | 2005-04-28 | 2012-08-28 | Bayer Intellectual Property Gmbh | Dipyridyl-dihydropyrazolones and their use |
| US8524699B2 (en) | 2006-10-26 | 2013-09-03 | Bayer Intellectual Property Gmbh | Substituted dihydropyrazolones and use thereof as HIF-prolyl-4-hydroxylase inhibitors |
| US8609698B2 (en) | 2006-10-26 | 2013-12-17 | Bayer Intellectual Property Gmbh | Substituted dipyridyl-dihydropyrazolones and use thereof |
| US8653074B2 (en) | 2010-11-18 | 2014-02-18 | Bayer Intellectual Property Gmbh | Substituted sodium 1H-pyrazol-5-olate |
| US8987261B2 (en) | 2006-10-26 | 2015-03-24 | Bayer Intellectual Property Gmbh | Substituted dihydropyrazolones for treating cardiovascular and hematological diseases |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK529378A (da) * | 1978-01-09 | 1979-07-10 | Shell Int Research | Anilidderivater |
| NZ213630A (en) * | 1984-10-19 | 1990-02-26 | Ici Plc | Acrylic acid derivatives and fungicidal compositions |
| DE3527157A1 (de) | 1985-07-30 | 1987-02-12 | Bayer Ag | 1-heteroaryl-4-aryl-pyrazol-derivate |
| DE102008020113A1 (de) | 2008-04-23 | 2009-10-29 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dihydropyrazolone und ihre Verwendung |
| DE102007044032A1 (de) | 2007-09-14 | 2009-03-19 | Bayer Healthcare Ag | Substituierte heterocyclische Verbindungen und ihre Verwendung |
| DE102007048447A1 (de) | 2007-10-10 | 2009-04-16 | Bayer Healthcare Ag | Substituierte Dihydropyrazolthione und ihre Verwendung |
-
1976
- 1976-10-25 GR GR52014A patent/GR63123B/el unknown
- 1976-10-28 IL IL50792A patent/IL50792A/xx unknown
- 1976-10-29 CA CA264,490A patent/CA1067907A/en not_active Expired
- 1976-11-01 IE IE2429/76A patent/IE43807B1/en unknown
- 1976-11-02 ZA ZA00766561A patent/ZA766561B/xx unknown
- 1976-11-04 NZ NZ182530A patent/NZ182530A/xx unknown
- 1976-11-05 PH PH19097A patent/PH13076A/en unknown
- 1976-11-08 DE DE19762651008 patent/DE2651008A1/de not_active Withdrawn
- 1976-11-25 SE SE7613239A patent/SE430413B/xx unknown
- 1976-11-25 PT PT65890A patent/PT65890B/pt unknown
- 1976-11-26 AR AR265630A patent/AR218861A1/es active
- 1976-12-02 ES ES454061A patent/ES454061A1/es not_active Expired
- 1976-12-02 CH CH1520676A patent/CH622784A5/de not_active IP Right Cessation
- 1976-12-04 RO RO88642A patent/RO72400B/ro unknown
- 1976-12-06 GB GB50713/76A patent/GB1570623A/en not_active Expired
- 1976-12-06 MX MX765189U patent/MX3832E/es unknown
- 1976-12-06 FR FR7636699A patent/FR2334674A1/fr active Granted
- 1976-12-07 CS CS7600007973A patent/CS186746B2/cs unknown
- 1976-12-08 DD DD7600196193A patent/DD129326A5/xx unknown
- 1976-12-08 DK DK550876A patent/DK550876A/da not_active Application Discontinuation
- 1976-12-09 BG BG034872A patent/BG27547A3/xx unknown
- 1976-12-09 AT AT911876A patent/AT354434B/de not_active IP Right Cessation
- 1976-12-09 AU AU20436/76A patent/AU507882B2/en not_active Expired
- 1976-12-10 PL PL1976194292A patent/PL106071B1/pl unknown
- 1976-12-10 IT IT30299/76A patent/IT1123686B/it active
- 1976-12-10 SU SU762427094A patent/SU643083A3/ru active
- 1976-12-11 JP JP51149321A patent/JPS6033112B2/ja not_active Expired
- 1976-12-13 NL NL7613810A patent/NL7613810A/xx not_active Application Discontinuation
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8252817B2 (en) | 2005-04-28 | 2012-08-28 | Bayer Intellectual Property Gmbh | Dipyridyl-dihydropyrazolones and their use |
| US9085572B2 (en) | 2005-04-28 | 2015-07-21 | Bayer Intellectual Property Gmbh | 4-(pyridin-3-yl)-2(pyridin-2yl)-1,2-dihydro-3H-pyrazol-3-one derivatives as specific HIF-pyrolyl-4-hydroxylase inhibitors for treating cardiovascular and haematological diseases |
| US8524699B2 (en) | 2006-10-26 | 2013-09-03 | Bayer Intellectual Property Gmbh | Substituted dihydropyrazolones and use thereof as HIF-prolyl-4-hydroxylase inhibitors |
| US8609698B2 (en) | 2006-10-26 | 2013-12-17 | Bayer Intellectual Property Gmbh | Substituted dipyridyl-dihydropyrazolones and use thereof |
| US8987261B2 (en) | 2006-10-26 | 2015-03-24 | Bayer Intellectual Property Gmbh | Substituted dihydropyrazolones for treating cardiovascular and hematological diseases |
| US8653074B2 (en) | 2010-11-18 | 2014-02-18 | Bayer Intellectual Property Gmbh | Substituted sodium 1H-pyrazol-5-olate |
| US9533972B2 (en) | 2010-11-18 | 2017-01-03 | Bayer Intellectual Property Gmbh | Substituted sodium-1H-pyrazole-5-olate |
Also Published As
| Publication number | Publication date |
|---|---|
| AT354434B (de) | 1979-01-10 |
| IE43807B1 (en) | 1981-06-03 |
| FR2334674A1 (fr) | 1977-07-08 |
| NL7613810A (nl) | 1977-06-14 |
| CH622784A5 (en) | 1981-04-30 |
| AR218861A1 (es) | 1980-07-15 |
| SU643083A3 (ru) | 1979-01-15 |
| JPS5273868A (en) | 1977-06-21 |
| PT65890A (en) | 1976-12-01 |
| JPS6033112B2 (ja) | 1985-08-01 |
| DK550876A (da) | 1977-06-12 |
| ES454061A1 (es) | 1978-03-01 |
| PL106071B1 (pl) | 1979-11-30 |
| GB1570623A (en) | 1980-07-02 |
| DE2651008A1 (de) | 1977-06-23 |
| SE7613239L (sv) | 1977-06-12 |
| AU507882B2 (en) | 1980-02-28 |
| PT65890B (en) | 1978-05-18 |
| PH13076A (en) | 1979-11-23 |
| IL50792A0 (en) | 1976-12-31 |
| FR2334674B1 (cs) | 1980-11-07 |
| RO72400A (ro) | 1983-04-29 |
| BG27547A3 (en) | 1979-11-12 |
| MX3832E (es) | 1981-08-04 |
| NZ182530A (en) | 1978-06-20 |
| IE43807L (en) | 1977-06-11 |
| IL50792A (en) | 1979-05-31 |
| ATA911876A (de) | 1979-06-15 |
| GR63123B (en) | 1979-09-11 |
| CS186746B2 (en) | 1978-12-29 |
| ZA766561B (en) | 1978-06-28 |
| RO72400B (ro) | 1983-04-30 |
| AU2043676A (en) | 1978-06-15 |
| DD129326A5 (de) | 1978-01-11 |
| IT1123686B (it) | 1986-04-30 |
| SE430413B (sv) | 1983-11-14 |
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